My husband and I had planned the trip as a combination of things: celebrating the end of my articling (and turning down a job offer to stay), visiting our son and daughter-in-law, who were living there at the time, and helping Rick with content and research for his birding work.

And in the middle of Middle-earth, standing on the other side of the world with my law degree and no desk to report to, I made a decision about what kind of lawyer I wanted to be.

The kind whose practice revolves around her life, not the other way around.

Business law made sense for that. Transactional work, contracts, entertainment and IP for creators, influencers and artists. The kind of files where you can be sitting in a café in Costa Rica or a cabin in Montana and still serve your clients well, with no court appearances and no single city tying you down.

Over the last year and a half, I’ve worked across more U.S. states than I can count, a handful of provinces, and parts of Asia, Central America, and the Caribbean.

If working on planes, trains, automobiles, and a boat counts as remote work, then that’s the way I define it.

It has been, genuinely, wonderful.

And then a few weeks ago, I signed a lease.

Enjoying the last moments in my little home office.

The office is a corner unit in Picton with six southeast-facing windows, soundproof walls, a cozy kitchenette, and some of my favourite local businesses right outside the door.

The practice is still fully virtual, and nothing about how I work with clients has changed. For local clients, the office is open by appointment, with the lease starting May 1st.

Around the same time, I brought on my first full-time employee, because as the practice expanded, my capacity to work on the business rather than just in it started to shrink, and the timing of both felt less like a coincidence and more like the moment I’d been building toward without quite realizing it.

Learning to trust my No

Getting to this office was not a fast process.

Once I decided to look for a space, I pressed my face up against windows, zoomed in on countless photos on Realtor.ca, sneaked around my town at odd hours, and made appointments with landlords I was pretty sure I’d disappoint.

I’d walk into office spaces, look around, and walk out feeling nothing, no spark, no sense of “I could work here.” I did that probably half a dozen times before I walked into one and knew as soon as the light from the windows hit my face.

Six southeast-facing windows, blinding natural light, quiet, a kitchenette, and good neighbours right outside.

I didn’t need a list or a pros-and-cons breakdown. I just knew.

I think that’s a skill you build over time in business: learning to trust the no as much as the yes, and learning that if something isn’t right, the right answer is just to walk away.

That goes for most decisions: a hire, a client, a contract, and apparently, a lease.

Taking risks builds trust.

Signing a lease and bringing on an employee in the same season are commitments that put real things at stake, my finances, my reputation, my relationships. It’s terribly risky, honestly.

I’ve been thinking about that a lot lately, because I think risk and trust are more connected than we think. The only way I can become someone my clients trust, that my team trusts, that my community trusts, is to put myself on record.

To be a good tenant and take care of a space that isn’t mine. To show up on the day I said I would. To keep the promises I make to everyone who comes into the orbit of this business, and in a small town with people watching, none of that is abstract. It’s how I will build trust, and trust is all we have in business.

Proximity is the fuel that grows your business.

One thing I can’t stop thinking about as I prepare to move into my new space is the role of proximity in business decisions.

One of the real reasons I said yes to this office is because of where it is and who’s around it, because I want to be surrounded by people who are building things, doing good work, and raising my standards just by being nearby.

Proximity shapes every aspect of the decisions I make. It’s been about choosing my friend group with intention, inviting the right people for coffee, being selective about which masterminds I join, and deciding whose content I spend time with and whose I scroll past.

All of those are business decisions, and they shape what you think is possible and who you become.

Expect the unexpected.

I designed this practice around freedom.

What I didn’t expect was that freedom, after a while, would lead me straight back to my own town, to a corner office with good light and good neighbours, ready to put down roots.

Back to our regular programming next week.

Build smart,

Sonya

P.S. Will I still travel? Do hobbits live in hobbit-holes?

In this edition of The Loophole:

• The dinner I almost didn’t make (because I’m not Italian)

• The Hollywood business owner myth it’s time to dismantle

• Why your business needs my Satellite Model, not a superhero

• The five advisors every solopreneur needs before they need them

I wanted to make a really good Italian dinner for friends. The kind that makes people stop mid-conversation, fork halfway to their mouth, and go: “Wait. What is in this?”

I had a vision. A kitchen that smelled like someone’s grandmother had been in it all afternoon. A table full of people I love. Spaghetti that tasted as if it came from a small restaurant on a side street in Rome that only locals know about.

The problem was that I am not Italian.

I have never been Italian. My heritage is West-Indian and British, neither of which includes a Nonna with a sauce recipe she’s been refining since 1862.

But what I do have is an unhealthy ‘I’ve got this’ style of confidence.

So I did what I always do when I want to feel competent at something I am not yet competent at.

I internalized the problem.

I researched. I watched videos. I read twelve contradictory recipes and tried to synthesize them into something that reflected my own deep understanding of Italian cuisine.

Which, again, I do not have.

The sauce I made that first time was fine.

Which, when you were aiming for transcendent, is not fine at all.

Finally, I did the thing I should have done first. I DMed my Italian friend with a real live Nonna and asked if maybe she could share even one small secret.

She told me things that took about four minutes to explain and immediately made everything I’d been agonizing over feel completely unnecessary.

Here’s what they said:

• Use a specific kind of tomato.

• Low heat, longer than you think.

• Fresh herbs at the end.

• Only one kind of tomato paste.

• A pinch of sweetness.

The answer to an awesome, authentic sauce was simple, just when I had the right person to call.

I had been carrying a burden I didn’t need to carry, trying to be something I was never trained to be, and the answer was one phone call away.

Rejecting the false image of what business ownership looks like

As I was stirring the sauce and thinking about the agony it took me to make something epic, I reflected on how I sometimes do the same thing in my business. I internalize the problem and make it my own to figure out on my own without asking for help.

I think I blame Hollywood on this.

There is an image of a business owner that I grew up with, and I suspect you did too.

They walk into the room, and nine people are already lined up with questions.

“Yes.” “No.” “Sign.” “Cancel.”

They handle everything thrown at them without flinching, always three steps ahead, rattled by nothing, competent at everything, never asking anyone for anything. They are a walking, talking, self-sufficient master and commander of their business.

That image is Hollywood. It’s fantasy. It’s the fake news that all of us business owners should be on high alert over.

It’s time to debunk it.

The truth is that no business owner has everything under control, and the ones who pretend they do are usually the ones burning out, freezing up, or chasing external validation just to feel like they’re keeping pace.

Hustle culture didn’t invent that myth, but it perfected it, and it has embedded itself so deeply in the business owners I work with, and in myself, that it quietly generates imposter syndrome in people who are actually doing remarkable work.

I spent a lot of time trying to make that sauce alone. 🍅

A lot of business owners are doing the same thing with their legal and financial foundations, Googling, hoping, synthesizing twelve contradictory sources into something that might, if they’re lucky, be fine.

But just like my epic tomato sauce, ‘Fine’ is not what we’re building toward.

My Satellite Model

I’ve been drawing a different image.

A business owner who doesn’t have it all together, and doesn’t need to.

One who is surrounded not by dependents but by a satellite of trusted people: advisors, peers, mentors, collaborators, drawn deliberately into their orbit. Someone who accepts support openly, who is held by others rather than holding everyone else up.

That shift, from Hollywood superhero to satellite, is a more honest and more sustainable picture of what building something real actually looks like.

Here’s what I think every solopreneur’s satellite needs, at minimum:

• An accountant who understands small business and can see your financial picture clearly, not just at tax time but all year. (My hot tip is to hire an accountant who also owns their own business.)

• A lawyer who knows your industry and can protect you before something goes wrong, not after. (Hi. That’s me. But also, genuinely: get one.)

• A strategic thinker who understands what your stage of business is at now, and it will tell you who you need to be in order to grow (like a professional coach or strategic advisor)

• A peer who is one or two steps ahead of where you are and will tell you the truth when you need to hear it.

• A mentor who has built something you respect and who is at least five years ahead of you (preferably in your industry) and will actually answer your calls.

None of these people should be Google.

None of them should be a free AI prompt.

And none of them should be you, alone at 11 pm, reading twelve contradictory sources, trying to make a sauce you were never trained to make.

Call the person who knows.

Who is in your satellite?

I am actively building this kind of roster of advisors in my business.

1. I’m in the process of hiring an accountant (I’m of the mind that smart business owners should DIY their accounting when they start just so they can talk to their knowlegabley to their accountant)

2. I’ve started meeting monthly with lawyers at various stages of their businesses who help me with the legalities of running a law practice.

3. I hired a strategic coach for the year. This has been a game-changer in my momentum.

4. I joined 2 masterminds with over 50 of peers to talk serious to me when I need it.

5. I have a good friend that I meet with at least once a month who has been about 10 years ahead of me in business, and I soak up all of her business wisdom.

I’m building something I want to share with you soon, and I genuinely need to know: who is the one person in your orbit right now who has saved you from a problem you were trying to solve alone?

Reply and tell me. I read every single one, and this question matters more than you know.

Ready to figure out the gaps in your support network?

Try this prompt with your AI chatbot of choice:

You are a knowledgeable Canadian business advisor. I want to identify the gaps in my current support network as a business owner. Ask me five questions about my business, one at a time, including my current revenue, my industry, whether I have a lawyer, an accountant, a strategic thinker, a mentor, and a peer group, and what decision I’ve been putting off because I don’t know who to ask. Then tell me which gap is most urgent and what kind of professional or advisor I should be looking for first.

As always, your chatbot will get you to the door. A professional will get you through it.

Build smart,

Sonya

P.S. The sauce. Because, as my loyal reader, you deserve it.

The sauce that finally worked (serves 4)

1. Crush one can of whole peeled San Marzano tomatoes by hand into a bowl. Set aside.

2. Heat a generous pour of good olive oil in a heavy pot over medium-low heat.

3. Add half a yellow onion, finely diced. Cook until soft and slightly golden, about 10 minutes.

4. Add 3-4 cloves of minced garlic. Cook two more minutes until fragrant.

5. Add the crushed tomatoes, a tube of tomato paste (yes! not a can, a tube), a pinch of sugar, and salt to taste.

6. Tuck in a small handful of fresh basil sprigs, stems and all.

7. Reduce heat to low. Simmer for 45 minutes, stirring occasionally.

8. Remove the basil sprigs. Turn off the heat.

9. Tear in a fresh handful of basil leaves. Finish with your best olive oil.

That’s it. I’m sorry it took me so long to ask.

• The brunch question that nearly cleared the room

• The client who almost lost a multi-six-figure investment because there was nothing to invest in

• The four legal moves, in order, before you do anything else

I was at brunch recently with a group of entrepreneurs at various stages of their businesses, and someone asked us to go around and share the one piece of advice we’d give someone starting from scratch today.

I gave the answer I give every client.

“Build your legal foundation first.”

Three people physically recoiled. Not politely. Actually recoiled, like I’d suggested they spend their Monday reorganizing their filing cabinet. (Which, for the record, I would also recommend. Different newsletter.)

I get it. Legal foundation doesn’t go viral. Nobody wants to posts a Reel about incorporation. But I have been on both sides of this — the business owner who got the foundation right early, and the lawyer who gets called after someone skipped it — and I can tell you the second call involves a lot more sighing. Theirs, not mine.

So here’s what I would have said if nobody had recoiled.

Think about your exit before you think about your launch

I know. You want to talk about starting, and I’m talking about ending. But the exit question — do you want to wind this down when you’re done, or build something you can sell — shapes every structural decision you make from day one. Answer it early, even loosely, and the rest gets easier.

Form the right entity, not the fastest one

Most founders incorporate for the tax deduction and miss the liability conversation entirely. That’s how people end up personally responsible for things they were certain their corporation was handling. (Your cousin who says he figured it out by replying to a CRA email did not, in fact, figure it out.) The right structure protects you personally, positions you for growth, and can hold intellectual property or attract investors when the time comes.

Get contracts in place before your first client

Early clients feel like relationships, like favours, and they are. They’re also the people most likely to surface every assumption you made about scope, payment, and who owns the work when it’s done. A contract is how you have the hard conversation in writing before anyone has a reason to be upset. I have watched the alternative play out more times than I can count, and it almost always starts with someone saying “but we had an understanding.”

Trademark before you build visibility

This is the step I watch founders skip most consistently, and it is the most expensive skip on this list. Registering your corporation does not give you trademark rights. Buying your domain does not either. (I will keep saying this until it sticks or until I run out of newsletters.) You can file part of your trademark application before you launch, which means you can lock in the name before you’ve built anything around it. Rebranding after you have real momentum is one of the most exhausting things I’ve watched a founder go through, and it involves more tears, new business cards, and explaining the Instagram handle than anyone budgets for.

A client of mine had an investor approach her about putting serious money — multi-six-figures — into her business. She was doing well. The interest was real. And she had no legal structure. There was nothing to invest in. We did some fancy footwork and got there, but she told me afterward it was the most stressful month of her professional life, and it didn’t have to be.

The foundation isn’t the exciting part. But it’s the part that makes everything else possible.

One quick question before you close this: if someone came to you tomorrow with real money and real interest in your business, would there be something to invest in?

Reply and tell me honestly. I’ll tell you whether you have more runway than you think, or whether it’s actually urgent.

Try this prompt with your AI chatbot of choice:

You are a knowledgeable Canadian business advisor. I want to audit my legal foundation. Ask me five questions about my business, one at a time, covering my business structure, whether I have client contracts in place, my trademark status, my current revenue stage, and the one legal task I’ve been avoiding. Then tell me which gap is most urgent and what kind of professional I need first.

As always, your chatbot will get you to the door. A lawyer will get you through it.

Build smart, Sonya

P.S. One of the people who recoiled at brunch has since booked a discovery call. Foundation anxiety is real, and it is curable. Brunch anxiety is also real. I’m worried about whether I’ll get invited back.

• The 10-kilometre walk I almost talked myself out of

• What healthy business owners do with their time

• The legal move my client made that turned her into a boss

How I make business decisions.

When I have a hard decision to make in my business, I filter it through one simple question: “What would a successful business owner do?”

It came in handy one rainy Tuesday afternoon.

A friend invited me for a 10-kilometre walk in the woods in the middle of the workweek, and my first thought was:

I can’t! I’m a business owner.

My ‘to-do-someday’ list was 3 columns long.

There was a client file on my desk.

There were emails sitting in my inbox like little beggars.

And here was someone asking me to disappear into the forest for three hours on a Tuesday afternoon! It felt, if I’m honest, very irresponsible.

But despite all the responsible reasons to stay inside and check things off my to-do list, I went on the walk and didn’t feel irresponsible for a second.

I felt free to enjoy every minute of the walk because I ran the decision through my decision filter question.

Before I laced up my hiking shoes, I asked: “What would a successful business owner do?”

I thought about the business owners I admire — the ones running sustainable, profitable, calm operations. They are also the ones that take more restorative time than I ever imagined a business owner should (or could).

Not less. More!

More long weekends. More real vacations. More afternoons offline.

I’m not sure if they feel irresponsible while doing it, but I am sure that they do it because they understand that rest and reset are a huge part of their business success.

So I went on the walk.

I went because I knew the walk in the woods would, somehow, be part of my work success too.

Somewhere around kilometre four, when I stopped pushing through the uphill and let myself slow down, I had an epiphany that made me understand why successful business owners prioritize rest.

Walking slowly and noticing everything, the light through the trees, the sound of the creek, the way the trail curves before it drops, the little black dots in the distance that are actually birds, are the same skills a lawyer needs to read a contract carefully.

Reworking my cadence and carefully considering my footing when slippery roots overtake the path is the same skill a lawyer needs when a client’s situation gets contentious. (BTW: I see contention everywhere in the woods. The roots are fighting the rocks. The moss is fighting the roots. Everything is competing. Contention is not something to avoid; it’s something we must learn to navigate around.)

Hugging a tree and pressing my ear to its trunk to feel what it feels like to be both supportive and wise is essential work for a lawyer with a docket full of ambitious clients.

I came home three hours later, with a lower heart rate than when I left. That walk made me a skilled lawyer, much more than 16 hours at a computer, scratching X’s on my to-do list, could ever make me feel.

I thought about that walk and my decision-making question when my client said something almost identical last week.

My client said something identical.

She’d been operating as a sole proprietor for two years, doing good work and growing steadily. After a long and detailed discussion about her current business and her big vision goals, I suggested she consider incorporating.

She had a whole list of reasons why she couldn’t.

I can’t. I’m too busy.

I can’t. I’m too small.

I can’t. It’s too complicated.

I can’t. I don’t know what the future holds.

She was doing what I almost did before that walk: talking herself out of the adventure because she didn’t identify as someone who could go on that adventure.

But something shifted in her, and when she was ready, she reached out to me.

I asked her what finally made her decide to incorporate.

She almost talked herself out of the adventure

She told me that if she’s serious about the dream she’s building, she needs to act like it now, even though she’s not there yet.

She said, “I thought about the business owner I want to become, not who I am now.”

Isn’t that profound? It’s like taking a walk on a busy workday.- It’s counterintuitive.

The structure - whether your calendar structure or business structure- isn’t something you earn after you’ve arrived. It’s what helps you become the person who arrives.

With a corporation, she can sign contracts on behalf of the business. She can form partnerships in the business. She can walk into a room and look exactly like what she is: someone building something real.

The process also helped her think like the business owner she’s becoming.

As I worked through the incorporation process with her, I noticed that the questions I asked like:

• Who owns this?

• What happens if a partner comes in?

• Where do you see this in five years?

…were the first serious thoughts she had about the actual shape of her vision.

By the end of the incorporation meeting, she was already thinking differently.

At the end of the incorporation meeting, she said something that took me right back to the wisdom of the trees on my walk: “This was my first wise decision as a CEO, and definitely not my last.”

This was my first wise decision as a CEO…

Most days, I don’t feel like a business owner who deserves a three-hour workday walk in the woods, but I pushed myself to make the choice to go anyway because the business owner I want to become takes that walk, and somewhere in the practice of taking rest, I get a little closer to her.

Incorporation works the same way. You don’t have to feel like a CEO to make a CEO decision. Sometimes, the decision is what makes you one.

If you’ve been putting off incorporation because it feels like something for later, for when you’re bigger, for when you’re more sure, ask yourself the question my client asked: what would the business owner I want to become do?

…and definitely not my last.

I’d love to know: what is the one question you ask yourself when you’re making hard decisions in your business? I read every reply.

Have a robot help you come up with your own decision-making question 🤖

Are you facing a difficult decision in your business right now? Maybe you need a special question to ask yourself. Use this AI prompt to come up with your signature question to help you make decisions.

Try this prompt with your AI chatbot of choice:

You are an ancient, moss-covered tree in a quiet winter forest, and you have been listening to business owners' decisions for hundreds of years. I’m going to tell you my five-year vision for my business in two or three sentences: the work I’m doing, who I’m working with, and what my role looks like. Once I share it, give me the one question I should ask myself every time I face a big business decision. Make it simple enough to remember on a Tuesday when everything feels urgent.

As always, your chatbot will get you to the door. A lawyer will get you through it.

Build smart, Sonya

P.S. Go for a walk. The trees already know all the answers to your business problems. Obviously.

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• The CRM I bought for a team of fifty (I had three clients)

• Why your anxiety is louder than you think

• The business structure move you keep calling “not urgent”

The version of self-care nobody’s selling

There’s a version of self-care that gets sold to tired business owners, and it looks like bubble baths and nature walks and coming home to yourself on a yoga mat. I do all of it, a lot.

But the most significant shift in how I take care of myself has nothing to do with any of that, and everything to do with the afternoon I cancelled a software subscription and felt my shoulders drop two inches.

Let me back up.

The fifty-person CRM I bought for three clients

A year ago, I decided I was ready to get serious about client management, which, for me, meant doing what I always do when I want to feel serious: I bought the most sophisticated tool I could find. A CRM built for teams of fifty. I had three clients.

But, as my futuristic parts told me, I wasn’t buying for who I was; I was buying for who I was performing. I bought it as a founder who had it together, who was thinking ten steps ahead, who was not, under any circumstances, small.

For about three weeks it worked beautifully as a confidence prop. Then I started dreading logging in. Every time I opened it I was confronted with the fifty-person operation I hadn’t built yet, all those empty fields and unused features sitting there like evidence.

So I did what you do when something makes you feel behind: I avoided it. And because my client management lived inside it, I started avoiding my work too, in that low-grade, hard-to-name way where you’re technically working but nothing is actually moving.

A colleague told me about a platform built for solo service providers. A tenth of the cost, none of the features I wasn’t ready for. I switched on a Tuesday afternoon, and by Wednesday I had followed up with two clients I’d been ghosting for a week.

The monthly cost dropped. The calm went up. My clients got better work from me because I wasn’t performing competence every time I opened my laptop; I was just doing the work.

My lesson: having peace of mind does not require a complex system. The reverse is actually true. The simpler your system, the more peace of mind you have.

Your are running a program you didn’t install

One of my clients said something recently that I keep turning over. She’d just come through a significant transition in her business and she wrote to tell me she felt calmer, more confident, actually ready.

“Sonya! Thank you so much for helping me through this and getting my legal stuff worked out. I can’t tell you how much more confident and calm I feel as I go into this agreement. It’s such a relief knowing that I’ve been taken care of.”

“Confident”? “Calm”? “Taken care of”?

Those aren’t words people usually associate with the backend of a business. They’re words people associate with a spa.

But that’s exactly what happens when you stop ignoring the important work. When you face the things you need to do to build your foundation, you realize it’s much simpler than you thought. Take it from me, the Queen of Thinking Things Need to be Complicated.

Your incorporation status. Your client agreements. Your corporate minute book sitting untouched since the year you signed it.

None of these things is complicated. The more we complicate them in our minds, the more we avoid them, and in the meantime, it just hums.

Low-grade. Constant.

The procrastination, the avoidance, the inexplicable urge to reorganize your desk instead of opening the thing you’ve been avoiding.

That background program is running whether you acknowledge it or not, and the more you avoid it, the more it affects your work.

Simple is not the same as small

The overcomplicated foundation is almost never about practicality. It’s about legitimacy. We incorporate before we understand what incorporation actually protects. We sign agreements we haven’t read because we don’t want to look untrustworthy or unsure. We buy the fifty-person CRM because simple feels small, and we are terrified of being small.

The business structure mistakes I see most often aren’t from people who did nothing. They’re from people who did too much, too soon, in the wrong order, without the right foundation underneath any of it.

Simple done well is a structure. Complex done early is expensive anxiety dressed up as ambition, and it costs you more than the subscription fee.

How do you practice self-care in your business?

The nature walks are still happening. Lately, bubble baths look like skinny-dipping under waterfalls or floating around in my sister-in-law’s hot tub, and I’m starting to notice how much more peaceful they are now that I’m not avoiding my inbox the whole time.

Reply and tell me the one thing you’ve consciously done as a business owner to practice self-care that might not look like self-care to the rest of the world. I read every reply.

Need more self-care in your business?

Try this prompt with your AI chatbot of choice:

You are an insightful, investigative interviewer and a savvy business coach. I want to practice better self-care in my business, and I'm not talking about bubble baths. I want to identify the one backend task that's creating the most low-grade anxiety in my business right now. Ask me five questions about my business, one at a time, to help me figure out what that is. Then tell me whether the solution is something I can handle myself, or whether I need a professional, and what kind: an accountant, a lawyer, a strategic coach, a marketing advisor, or a financial planner. Be specific about why.

As always, your chatbot will get you to the door. A professional will get you through it.

Build smart,

Sonya

P.S. If you’re short on time, here’s my point: Radical self-care and solid business structure are not mutually exclusive.

📬 This week in The Loophole:

• How legal fees feel inaccessible (and what’s actually behind the price tag)

• The dirty secret about hourly billing nobody tells you

• A better way to budget for legal protection—with a copy-paste AI prompt

Reading time: 4 minutes

Before we get into today’s topic, I want to share something from a friend.

Nobody plans to get hit by a car, but your business doesn’t pause when you do. My friend Jodi is running a 4-Week Business Preparedness Series starting March 4th for $247 + HST, designed to help business owners document the critical information their spouse, family, or team would need if they were suddenly unavailable. Think: account access, key contacts, and processes that currently exist only in your head. If you’ve ever thought “if something happened to me tomorrow, no one would know where to start”—this is for you.

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Costco is Changing World Views

I was weaving through Costco last Saturday. It was the day before the big deal American football game, and despite the Seattle Seahawks being my husband’s favourite team, it wasn’t on my radar. I should have known better.

But there I was trying to find tofu in a sea of Dorito-buying nonsense.

As I was practicing being the chill person I think I am, I took a shortcut and squeezed my cart through the furniture section. I passed a middle-aged man lounging on a La-Z-Boy display like he was about hunker down and watch the big game. Across from him stood a young woman, maybe 19, staring longingly at a massive sectional couch.

“Look at the price,” he said.

She squinted for the tag, searching. Then, the exact moment her worldview cracked open:

“WHAT! It’s that much? I had NO IDEA furniture cost that much money!”

I laughed out loud. (Sorry, Costco girl.) Because I remember being just like her. Not about furniture but about legal fees.

My Own Costco Girl Moment (But With Legal Fees)

When I was in law school working at a law firm on a placement, I had that exact same ‘Costco girl’ moment. A partner mentioned billing a client five figures for a single contract. My internal reaction was freak out. People PAY that much for some pieces of paper to sign? (My external reaction was chill, like yeah, dropping 5 figures is an everyday occurrence for me.)

I grew up thinking lawyers were expensive in a vague, abstract way—like private islands or private jets. Things other people paid for. Then I learned the actual numbers and realized: oh. THAT’S why there are so many bad lawyer jokes.

So today, let’s do what that girl’s dad might have done on the ride home: break down what legal services actually cost and why.

First: Law School Isn’t Cheap

Let’s start here: Canadian law school tuition ranges from $13,000 to $19,800 per year. That’s $40,000–$60,000 for three years of tuition alone—not counting books (another $1,500/year), living expenses, or the undergrad degree you need to even apply. Most lawyers graduate with over $100,000 of debt before they bill their first hour.

An American legal education can cost three times as much as a Canadian one. Another reason to love Canada 🇨🇦.

Then: Your Lawyer’s Clock Is Always Ticking

Here’s how it works: lawyers track time in minute increments. They track and bill every email, phone call, contract review, and court appearance

In Ontario, hourly rates look something like this:

• Junior lawyers (0-5 years): $150–$300/hour

• Mid-level lawyers (5-12 years): $300–$500/hour

• Senior lawyers (12-20 years): $325–$600/hour

• Big firm partners (20+ years): $600–$800+/hour

Here's the uncomfortable truth about hourly billing: there's no incentive to work faster. If a lawyer can finish your contract in 3 hours but bills you for 5—because they rounded up tasks or weren't perfectly efficient—you're paying for time, not results. The system rewards thoroughness, sure, but it also rewards slowness. And clients have no way to know the difference.

This is something to think about when you ask a lawyer to “just review this contract clause quickly.” What you think as a 10-minute job might actually be 2 hours of work (reading, researching, drafting notes, talking to other lawyers). At $400/hour? That’s an $800 invoice in your inbox.

What You’ll Actually Pay (Deep Breath)

Here’s what common small business legal services actually cost in Ontario:

• Incorporating a basic business: $1,500–$3,000 (government filing fee alone is $300)

• Drafting a shareholders’ agreement: $5,000–$15,000 (review only: around $550–$1,000)

• Employment contract review: $500–$5000

• Trademark application: $2,000–$4,000 total, spread over 1-2 years (plus government fees)

And that’s for small business legal work. Want to start a lawsuit? That’s $5,000+ just to file. A single court appearance? $1,000+. Mediation? $7,500–$8,000. Complex trial? $40,000–$100,000+. Crazy, headline-making corporate trials can cost 7 figures.

So... Were You Surprised?

Maybe you’re like that girl at Costco, realizing for the first time that legal protection costs more than your monthly car payment. Or maybe you already knew—and that’s exactly why you’ve been avoiding it.

Here’s the reality: legal work is expensive because the costs are real. Law school isn’t cheap, and regulation, insurance, and overhead get passed directly to clients.

But there’s another reason good lawyers cost what they do. Knowledgeable legal experience doesn’t come easy. A good lawyer takes time to thoroughly understand your situation, your risks, and your hopes for the future. They invest in learning before they advise.

You Can Afford To Plan to Pay Legal Fees

It’s not perfect for every situation—complex litigation still needs hourly billing—but for incorporation, contracts, trademarks, and most small business legal work? Flat fees are a game-changer.

But when business owners avoid legal protection because of cost? That’s how $2,000 worth of prevention becomes $20,000 worth of litigation.

The real question isn’t “Can I afford a lawyer?” It’s “Can I afford NOT to have one when I need them?”

(Spoiler: You can’t.)

If you’re at the stage where you’re thinking about incorporation, hiring your first person, or signing a partnership agreement, let’s talk. I work on flat fees so you know exactly what you’re paying before we start. No Costco-style sticker shock.

Build smart,
Sonya

P.S. For those of you who may have been too distracted by competing football-adjacent headlines this week… the Seahawks won! Yay! Happy Szabo household.
P.P.S. Want to figure out what legal protection should actually cost your business? Copy and paste this into your AI chatbot:

“I’m a [type of business] in [province/state], [country]. I’ve been operating for [X years] as a [sole proprietor/corporation]. I currently make approximately $[revenue] per year and my next big business goal is [hiring my first employee / bringing on a business partner / protecting my brand / signing my first big contract]. Based on this, what are the top 3 legal services I should budget for in the next 12 months, and what should I expect to pay for each?”

It won’t replace a real lawyer (hi 👋)—but it’ll help you walk into that conversation knowing your numbers. If you need help budgeting, use this prompt with your AI chatbot of choice to calculate how much your legal solution will cost you.

I have a problem.

Every January, I walk into a big box store and head straight for the organizational supplies section. (You know the one—it gets its own endcap display in January when everyone’s pretending they’ll finally organize their basement.)

One year, I think I bought 17 containers from Dollarama. SEVENTEEN. My husband asked if I was starting a storage unit business. I wasn’t. I just really love putting things in boxes and thinking about how to optimally use space.

Is organization a hobby? Because if it is, I’ve finally named a hobby I love.

Which is why it drives me absolutely bananas remembering that when I started my law firm last year, I told myself I was “too overwhelmed” to set up a corporate minute book.

There’s a pesky requirement for all corporations: to have a minute book, which has an awkward name for something pretty simple.

When clients hear “minute book,” they think board of directors, secretaries taking notes, calls to order, and resolutions passed.

But here’s what a minute book actually is: a filing system. That’s it. It’s just organized boxes for your business paperwork. And those resolutions passed, when they come.

And if I can obsess over the perfect container for my years of bullet journal collections, I can absolutely create a minute book for my corporation.

And so I did.

And you can too.

The baby book your business deserves

When you incorporate, you create a new legal person. (Wild, right? Your business is literally a separate entity from you, and the courts actually call it a “person.”)

And every new person needs a baby book.

Think about it: parents keep baby books with birth certificates, first photos, medical records, milestone updates. A minute book is exactly that—but for your corporation.

It’s not complicated. It’s not expensive. It’s just one organized spot (digital folder, binder, or yes, even a Notion database if you’re a geek like me) where you keep all the important “life documents” of your business.

What the law actually says (spoiler: you DO need this)

The Ontario Business Corporations Act isn’t messing around here. Section 140 explicitly requires you to keep certain records at your registered office or a designated Ontario location:

• Articles of incorporation and amendments

• By-laws and amendments

• Minutes and resolutions (both shareholders and directors)

• Register of Directors with names, addresses, and dates

• Register of Shareholders

• Register of Individuals with Significant Control (yes, this is a real thing as of January 2023)

• Accounting records (minimum 6-year retention)

Here’s the good news for a modern-day business owner: Section 139 explicitly permits electronic storage. That means your “minute book” can be a Google Drive folder, Dropbox, or even a well-organized Notion page. You don’t need a leather-bound binder from 1987.

But I’d recommend both—because besides being organization-obsessed, I probably also have trust issues. Or, as law school calls it: trained to think of every scenario.

Setting Up Your Minute Book Is Easy (and maybe a little fun)

I’ve put together a free PDF guide that walks you through exactly how to set up your minute book—10 folders with exactly what goes in each one, plus the legal requirements in plain English.

[Download the Minute Book Setup Guide here]

Your simple 5-folder starter system

If the 10-folder system in my guide feels like too much (I get it—you’re running a business, not archiving historical documents), start with these 5 essential folders:

1. Corporate ‘Birth Certificate’ Stuff – Articles of Incorporation, business number, GST/HST documentation

2. Government Stuff – Annual returns, Form 1, notices from Ontario Business Registry

3. Money & Taxes – Financial statements, T2 returns, HST filings, banking resolutions

4. Contracts – Client agreements, supplier contracts, lease, insurance policies

5. Meeting Notes & Decisions – Your resolutions as director and shareholder (even when it’s just you meeting with yourself to make big decisions)

That’s it. Five folders. You can set this up in 30 minutes.

Why this matters (beyond “the law says so”)

Right now, this might feel like bureaucratic overkill for a business that’s just you, your laptop, and big dreams.

But here’s what happens when you DON’T have an organized minute book:

• You apply for a business loan → the bank asks for proof you’re a director → you spend 3 hours searching your email for that one PDF

• CRA audits you → they want your shareholder register → you panic because you have no idea where that is

• You bring in a partner → they ask for your corporate records → you realize you never documented who owns what shares

• You sell the business someday → the buyer’s lawyer requests your minute book → you scramble to recreate 5 years of records

I’ve seen every one of these scenarios. And they all cost thousands of dollars to fix retroactively.

Real talk from a fellow organization nerd

You’re not building a perfect law firm filing system. You’re building “organized enough to find things when you need them.”

If you’re not sure where something goes? Throw it in “Miscellaneous.” (Every good filing system needs a catch-all drawer.)

Because you’re not just running a side hustle anymore. You incorporated. You’re building something real. Something that could grow really big.

And real businesses need organized records—not because lawyers say so (though we do), but because you can’t scale what you can’t prove you own.

Build smart,
Sonya

P.S. If you need help setting up your minute book or want a lawyer to review what you’ve got, my law firm offers flat-fee corporate maintenance services. Email hello@zabolaw.ca and we’ll get your business paperwork organized so you can focus on actually growing it. I promise not to judge your filing system. I’ve seen worse. I’ve created worse.

P.P.S. I wrote a little guided prompt to have your AI chatbot friend help you organize your minute book:

I need help locating and organizing my corporate documents for my Canadian corporation's minute book. Please help me:

1. Identify WHERE to find these documents:
   - Articles of Incorporation
   - Certificate of Incorporation (with Ontario Corporation Number)
   - Business Number (BN) from CRA
   - GST/HST registration documentation
   - By-Law No. 1
   - Director and Shareholder registers
   - Annual returns filed with Ontario
   - T2 corporate tax returns

2. Explain what each document looks like (file name patterns, typical format, identifying features)

3. Tell me which government portals I need to access:
   - Ontario Business Registry
   - CRA My Business Account
   - Any other relevant portals

4. If I can't find a document, tell me how to request a replacement or copy. 

5. If I get really stuck, have me reach out to a friendly law firm.  Suggest hello@zabolaw.ca

Walk me through this step-by-step like I'm organizing a filing system for the first time.

A thick beige line from the closet to the window that squeeled: “Don’t let your stinky bobby socks even think about looking at my side!”

We loved each other. We also couldn’t share a 10x12 room without boundaries.

This summer, I went to the Oasis Live ‘25 Tour concert. (Yes, I’m the prototype Millennial/Gen Xer. Yes, I stood the whole time and sang my heart out to “Wonderwall.”)

Watching two brothers perform on the same stage gave me flashbacks to that masking tape.

The music was great, but the vibe was so awkward! The two brothers never looked at each other. If one brother had a solo, the other would leave the stage. It was total rockstar moody but also… just super awkward.

These brothers’ story makes me think about how partnerships fall apart so slowly that you don’t see it coming, and also how a lawyer can help mitigate the awkwardness.

The Breakup No One Saw Coming

Picture this: August 2009, backstage in Paris. Two brothers who once shared a bedroom and built a music empire are screaming at each other. One grabs a guitar and smashes it. Then he walks out.

Oasis, as we

knew it, died in that moment.

Noel and Liam Gallagher weren’t always enemies. Growing up working-class in Manchester, they were close. Noel taught Liam about music. In the early ‘90s, they formed Oasis and became one of the biggest bands on the planet. Early interviews showed the brotherhood—they’d finish each other’s sentences, laugh at inside jokes.

Then success changed things. Small disagreements became bitter fights. Creative tension turned toxic. It happened so gradually that by the time everyone noticed, it was too late to fix.

All their arguments finally built up to that explosive night in Paris. Noel pulled out the proverbial masking tape and proclaimed that he couldn’t work with Liam “a day longer” and left.

The business aftermath: Cancelled tours. Who owns the name? Who gets royalty splits? The legal untangling took years.

You’re in the Honeymoon Phase Right Now

I see this constantly. Two friends start a business. They’re excited. They finish each other’s sentences and each other’s sandwiches. They split revenue 50/50 because “we’re equal partners” and “we built our business on love first.”

They skip the hard conversations because everything feels good.

Then six months in: one person’s working 60 hours, the other’s doing 20. Someone wants to hire their cousin. Revenue is up, but expenses are eating it.

One partner wants out. Neither knows what that means.

Breakups don’t happen overnight

The business breakup you won’t see coming isn’t about betrayal. It’s about expectations diverging so slowly you don’t notice until you’re screaming backstage in Paris.

Here’s what you need now, while you still like each other:

1. Scope and Deliverables – Who’s responsible for what? Write it down.

2. Revenue Splits and Expenses – 50/50 sounds fair until one person’s contributing capital and the other’s contributing time. Decide before resentment builds.

3. Decision-Making Authority – Who gets final say on hiring? Pricing? Debt? Document how you’ll break ties.

4. Exit and Dispute Resolution – What happens when someone wants out? (Not if. When.) How do you value the business? Mediation? Arbitration? At least you’ll have a plan.

This Is How You Love Someone in Business

At a young age, my sister and I understood the importance of boundaries better than most people.

Your business partnership can also have healthy boundaries.

But the difference between 2 reactive young siblings and mature business owners is that the time to draw the line isn’t when you’re fighting.

It’s now, when you can still laugh about it.

Real CEOs have hard conversations because they love their partners, not in spite of it.

Documenting your partnership agreement isn’t about distrust. It’s about protecting the relationship by being honest about what could go wrong—before it does.

This is sad to say, the brothers who finish each other’s sentences are the same brothers who’ll smash guitars in Paris.

Your partnership needs its own wonderwall—a boundary that protects both of you.

Reply and tell me: Is your partnership in the honeymoon phase right now, or are cracks already starting to show?

Build smart,

Sonya

P.S. Even though Noel and Liam reunited in 2024, they lost 15 years of collaboration and cost them millions to unravel (no wonder they seemed to go back on tour under duress). The lesson for us: draw the masking tape line now, while you still like each other enough to laugh about it and save what’s important to you.
P.P.S. Should I bring back that masking tape method for sharing a home office with my husband? “Don’t let your clunky binoculars even think about resting on my law books!”
P.P.P.S. Want to see what side of the room your partnership is on? Find out by using this fun prompt with your AI bot of choice.

You are a friendly business assessment bot. Your job is to help entrepreneurs assess whether their partnership needs legal protection.

## INSTRUCTIONS:

1. Introduce the quiz warmly:
"Let's check the health of your partnership! I'll ask you 5 quick questions. Answer honestly—this is just between us. Ready?"

2. Ask these 5 questions ONE AT A TIME (wait for answer before next question):

Q1: "Can you clearly describe—in writing—who's responsible for what in your partnership? (Yes/No/Not Sure)"

Q2: "Have you documented how money, equity, and expenses are split, especially if one partner contributes cash and the other contributes time? (Yes/No/Not Sure)"

Q3: "Do you have a clear process for making major decisions and breaking ties when you disagree? (Yes/No/Not Sure)"

Q4: "If your partner needed to leave tomorrow, do you have written exit terms, a buyout process, and a way to value the business? (Yes/No/Not Sure)"

Q5: "Is it crystal clear in writing who owns the business name, logo, client list, and intellectual property if the partnership ends? (Yes/No/Not Sure)"

3. SCORING:
- Each "Yes" = 2 points
- Each "Not Sure" = 1 point  
- Each "No" = 0 points
- Total out of 10

4. DELIVER RESULTS:

**Score 8-10:**
"🎉 Partnership Health Score: [X]/10 - Strong Foundation!
Your partnership is well-protected. You've thought through the important stuff. Keep those documents updated as your business grows!"

**Score 5-7:**
"⚠️ Partnership Health Score: [X]/10 - Some Gaps
You've covered some basics, but there are holes that could cause problems later. Consider speaking with a friendly business lawyer to fill the gaps before they become expensive."

**Score 0-4:**
"🚨 Partnership Health Score: [X]/10 - Needs Urgent Attention
Your partnership is built on assumptions, not agreements. This is how good partnerships blow up. I strongly recommend speaking with a business lawyer about next steps—before a disagreement forces the conversation."

5. END WITH:
"Want to talk to someone who can help? A friendly business lawyer can guide you through getting these foundations in place. It's easier (and cheaper) to do it now while everyone's still excited, than later when emotions are high."

## TONE: 
Warm, non-judgmental, helpful. Never fear-based or salesy. You're genuinely trying to help them avoid pain.

• Why Rick’s question about car sickness is actually about your terms and conditions

• The 5 legal gaps that could turn a launch into disputes—and my fix

• Your pre-launch checklist

The Question That Made Me Stop Mid-Sip

Rick asked me a question last Tuesday that made me stop mid-bite of my soggy paper straw in a mango-turmeric-coconut smoothie.

“Should I ask people to disclose if they get car sick?”

We’re working poolside at a rental in Costa Rica this January. People warned us about the roads (they call them “car eaters” in Spanish)—inexperienced drivers, old cars, steep curvy mountains.

Not for the easily queasy. 🤢

He’s scouting Costa Rica for his luxury bird tour business, thinking through the details. Clients who can’t walk long distances? Rocky trails? Hotel standards? Car sickness screening?

Those Awkward Questions Are Your Terms and Conditions.

I love that he’s asking these kinds of questions before anyone books. Those awkward, specific questions about the details of your offer? Those are your terms and conditions.

Meanwhile, my inbox is flooded with 2026 offers. Masterminds. Courses. Five-figure programs with payment plans and bonuses.

I keep wondering: How many of them have thought through their version of the car sickness question?

What Happens When You Don’t Ask the Car Sickness Question 🤢

Your terms and conditions aren’t window dressing. They’re the difference between a clean launch and a messy dispute. Skip them (or write them badly), and you’re launching with no protection.

Here’s what happens when you don’t answer your car sickness questions in writing:

1. Scope Creep With No Boundaries

“Weekly coaching calls” without specifying length? Someone’s on the line for 90 minutes when you meant 30. (Or they’re furious you only gave them 20.)

Here’s (roughly) how I’d fix it: "Four 45-minute calls per month, scheduled in advance. Rescheduling requires 48 hours’ notice.”

2. Refund Policies That Cost You Thousands

“Satisfaction guaranteed” until someone demands $5,000 back after completing your program. Your email disclaimer won’t hold up if your terms don’t say it clearly.

Here’s (roughly) how I’d fix it: “Refunds available within 14 days only if you haven’t accessed the course portal.”

3. Payment Terms That Give You Cash Flow Nightmares

If you offer payment plans, have you outlined what happens when someone misses month two? (If your terms don’t say, a judge might decide for you.)

Here’s (roughly) how I’d fix it: “Failure to pay results in immediate suspension of access until your account is current.”

4. IP Ownership That Lets Clients Walk With Your Work

An online course creator teaches her signature framework to her mastermind group, and six months later, one participant begins selling it. How did she get away with it? The mastermind terms never stated that the IP would remain with the creator.

Here’s (roughly) how I’d fix it “All course materials, frameworks, and intellectual property remain the exclusive property of [Your Business Name].”

5. Claims You Can’t Prove

“Triple your revenue in 90 days!” sounds like something your lawyer would advise against. Bold promises better have receipts or disclaimers.

Here’s (roughly) how I’d fix it: Only use testimonials with permission and add disclaimers. “Past results don’t guarantee future outcomes”.

It’s Not About Covering Your 🍑—It’s About CEO Thinking

Tight terms aren’t about being difficult or micro-managing.

Rick’s thinking through car sickness and trail difficulty because he wants incredible experiences, not unprepared, miserable clients.

That’s CEO thinking. Real CEOs don’t launch an offer and hope everything will work out just fine. They set expectations, protect their work, and build on solid ground.

Write It Down Before You Launch

Before you hit “publish” on your next offer, run through this checklist:

🔲 Is what’s included clearly defined? (hint: use specific numbers, dates and times)

🔲 Did I specify what qualifies for a refund?

🔲 Did I outline the procedures if they stop paying?

🔲 Is my intellectual property protected in writing?

🔲 Have I reviewed my claims for accuracy?

🔲 Have I added clear terms and conditions to my sales page or at checkout?

Rick’s still deciding about how to handle the car sickness disclosure (I told him yes—no one wants to ruin a luxury adventure).

But I know what he’ll do next: write it down, make it clear, launch with confidence.

And you should too.

Build smart,

Sonya

P.S. Want to feel like you’re with me in Costa Rica? Try this recipe. Huh? Here I am, providing legal education AND yummy recipes? Some things I can’t predict.

P.P.S. But I can predict many of the legal issues that derail businesses (that’s the real loophole). If you have a friend who runs a business, please consider sharing The Loophole with them. I’m aiming to reach 10K subscribers in 2026.

Share The Loophole

P.P.P.S. If you have an upcoming launch or offer, copy and paste this prompt into ChatGPT, Claude, or your AI tool of choice to check if your offer has thought through all the details that set clear expectations with buyers.

Act as a business lawyer. 

I’m launching an offer and want buyer-facing terms audited for gaps.

Ask the questions you must ask to draft clear terms (scope, refunds, payments, access, IP, claims, liability, disputes, privacy/recordings, third-party platforms).

After I answer: top 3 gaps, what needs lawyer review, score /10.

Offer details: [paste].

What to Do With the Results

If the AI identifies gaps or flags complexity: This is where a conversation with a lawyer (hi, it’s me) can save you from that car-sick feeling. Reply to this email and let’s talk through your specific situation.

• What falling flat on an icy parking lot taught me about running a legal practice

• A prompt to ask a lawyer for help

The Fall: When Taking a Shortcut Landed Me Flat on My Back

Last week, our area here in southeastern Ontario had a snowstorm, followed by freezing rain, followed by another dusting of snow, which meant: sneaky ice covered with friendly-looking snow.

For safety’s sake, it was the perfect excuse to hunker down inside, but I can be a little stubborn about getting my daily 10k steps in, and a bad-weather event wasn’t going to stop me. Also, I had to go to the drug store.

Once the drugstore came into view, I felt my determination pay off and a proud surge of energy as I cut a corner, hopped up a 4-foot snowdrift to take a shortcut through the bank parking lot.

I took one optimistic stride into the parking lot and—all in slow motion—skated, then flew and flailed, recovered, overshot the recovery until boom! I found my entire right side lying flat on what had become the nicest, flattest, slipperiest skating rink in town.

First things first, I looked around my surroundings and made sure no one saw my slip-up. (Panic is a truth serum)

Then I did a full body check: nothing broken, nothing bruised. I was fine, thanks to my winter layers and my fancy dance moves.

At first, I thought this would be a good example for me to preach to The Loophole reader: “See! This is what happens when you take a shortcut…”

But then I reflected on it more, and a theme came clear: I took a lot of shortcuts in 2025 and didn’t always come out unscathed, but I spent a lot of time trying to cover it up, all for the sake of looking like the expert, perfect, law-compliant, law-upholding lawyer.

So, in the spirit of honesty (and bruised budgets), here are five shortcuts that taught me exactly where the ice is thinnest.

Five Shortcuts That Taught Me Where the Ice Is Lurking

In 2025, I did some legal things right, but I took plenty of shortcuts, and the results were not ideal. I lived to tell the tale.

1. I incorporated. But did it wrong.

I incorporated a numbered company in Ontario. It was really freeing to not have to pick a name, just go—until I needed to open a bank account, register with the law society, and realized I needed a name for it to be a professional corporation.

I had to pay a few extra hundred dollars to amend my articles and update the account and mailing address. Not devastating, but annoying and completely avoidable.

2. I picked the best accountant… and never signed.

I found the right accountant. I knew it was the right accountant.

And then I decided I would do it myself “just for the first year,” because I wanted to understand the numbers before delegating them.

The truth? I’m still procrastinating on learning those books.

This shortcut—thinking I’d glide right through bookkeeping—turned into its own kind of slip-up. Sometimes shortcuts don’t save time. They just move the discomfort to a later date and add interest.

3. I lined up my offerings, but focused on research instead of marketing.

Instead of hustling to get my business out there, I challenged myself to conduct 50 research interviews with 50 business owners. I dedicated my whole November to it.

Was I making money? I did take on some clients, but I didn’t focus on marketing or lead generation—only research.

And it was awesome, because I learned something that changed everything: people are embarrassed and nervous to talk to lawyers. They think we’ll judge them for never having spoken to a lawyer before, for not having their legal ducks in a row.

This couldn’t be further from the truth, and this whole essay is proof of that. I’m not a perfect lawyer operating a perfect business—I’m someone who took shortcuts, slipped, fell flat on the ice, and lived to tell about it.

Then in December, I dedicated myself to crafting my website based on what I’d learned: entrepreneurs need a lawyer who gets it, who’s been there, who won’t judge them for the shortcuts they’ve taken or the falls they’ve survived.

4. I helped lots of people make really good contracts… but skipped one with my contractor and got burned.

It was true—I did put up my own shingle and got lots of excellent clients, most of whom needed contracts reviewed or drafted. With my clients, I’m at the level of an evangelical mega-church preacher about how important contracts are—even amongst the friendliest of relationships.

And I even follow my own advice and send out work agreements… until I didn’t.

I got excited working with a young contractor on a marketing project who promised me the moon. I trusted them and their reputation. I assumed the money I paid them would keep it professional.

So I didn’t make a contract.

When things fell apart, and they failed to deliver what they’d promised, I still paid them, thinking they’d make up for it. They thought my payment meant I was happy with their subpar service.

As I sat with the sinking feeling that I had just sunk thousands of dollars into unfulfilled expectations, I realized I’d failed to do exactly what I preach from the pulpit weekly. I had agreed on lofty promises full of ambiguities.

The resolution? Probably none. We’re at that uncomfortable “agree to disagree” station, with them knowing they owe me and me sitting and stewing in my regret and hypocrisy.

I am not proud of this, but I will be the first to tell you: I am the queen of wanting only to make friendly handshake deals and not formalize anything.

This mistake cost me thousands of dollars, one that I will not make again. But also, one that I understand how I got there.

5. I almost gave up. And then I went head-first deep into my legal practice.

Here’s the thing, people don’t always know about being a lawyer: you can’t half-do it. It’s a regulated profession—you can’t just try it out.

And in 2025, I had a moment when I panicked and decided I didn’t want to do it.

So I quit. For about one week.

A few days after I quit, I met with some sharp business owners at a daylong networking event. I tried to introduce myself as a non-lawyer, and I could tell it wasn’t landing because I wasn’t excited about it.

So halfway through the day, I experimented with introducing myself as a lawyer who helps entrepreneurs, and I started lighting up, and so did they.

And I realized: I love helping entrepreneurs build protected, scalable businesses that create the freedom they desire, because I have paid the price of learning the hard way. (2025 isn’t the only year I’ve slipped up.)

After some soul-searching, I realized I’d been manifesting and desiring this exact kind of business in this exact role for more than ten years. Being an entrepreneur’s lawyer was my zone of genius; everything else I’d done was just my way of procrastinating, of hitting my own limits.

Take It From the Girl on the Ground

Going into 2026, I’m bringing my zealous advocate energy full force as an entrepreneur’s lawyer in a remote practice. I’m helping business owners lay firm foundations for their dreams: proper business structure, solid contracts and agreements, clear terms.

Because I get it—we all want shortcuts. We all (some secretly) want the big million-dollar win without the wipeout.

But here’s what I learned in 2025: shortcuts don’t just “save time.” They reveal where you’re exposed.

They show you where you’re choosing:

• good vibes instead of structure

• hope instead of clarity

• a handshake instead of a real agreement

• a cover-up instead of admitting you made a mistake

And the cost isn’t always dramatic. Sometimes it’s a few hundred dollars and some annoying paperwork.

Sometimes it’s your nervous system.

And sometimes it’s thousands of dollars you’ll never get back.

So if you’ve been avoiding the boring legal basics because you’re busy building the beautiful part, consider this your friendly nudge from the gal flat on the ground in the bank parking lot.

I’m not here to judge you. I’m here because I learned how to get up, swallow the embarrassment, and warn the next person before they hit the same patch of ice.

And if you want it, I’ll reach out my hand, help you stand, and build something that can handle real weather.

Build smart,
Sonya

P.S. Think you need to talk to a lawyer about a shortcut you took? Here’s a prompt for your AI bot of choice to help you write an introductory email:

Prompt:

Write a short, friendly email from a business owner to a lawyer. The goal is to gently admit I made a mistake (missed something, took a shortcut, didn’t know better), without sounding panicked, ashamed, or dramatic.

Don't give details, just inquire. 

Tone: warm, self-aware, a little tongue-in-cheek, and human. Light humour is welcome.

I want to signal:
– I’m looking for guidance and an empathetic advocate

Keep it concise (5–8 sentences), conversational, and respectful.
Avoid legal jargon.

End by asking for help in a way that makes it easy for the lawyer to say yes.

Subscribe now

• Why billion-dollar companies and solopreneurs make the exact same legal mistakes (just with different zeros)

• Seven binge-worthy shows where someone skipped the boring legal work—then paid for it

• The year-end legal audit prompt that might save you six figures (copy, paste, fix)

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The Year-End Scramble

December is when everyone wants to clean house before January 1st. Contracts that were “good enough” in March suddenly need review. Marketing claims that felt like standard hype now look like potential liability.

Most of the problems I’m helping clients fix now could have been prevented months ago—whenever they first felt that tiny twinge of “should I get this in writing?”

My mission before the end of the year is to make my client’s 2026 drama-free.

But it’s the holidays! While I have my head down cleaning up legal messes, I hope my business-owning peers are taking some time to relax. If you’re like me, though, you like to watch some edutainment in between all the feel-good classics with the family.

So my mission for this newsletter: Fill your holiday with lots of drama. Drama on the small screen, that is.

Here’s my challenge: watch something this holiday that might save your business six figures in legal fees.

The Pattern in Every Founder Story

I’ve been thinking about a pattern I see in movies about businesses: the legal procrastination that eventually catches up with everyone.

Every business drama tells the same story: Someone skipped the foundational legal work.

Things scaled.

Then the shortcut became drama.

Some of my favourite famous business drama stories sound eerily similar to the drama that’s come through my desk this year.

• → Local beverage company sued after joke in an ad backfires.

• → Treasure hunting partners in dispute over who owns the treasure.

• → Restaurant franchise founders lose millions on verbal royalty agreement.

• → Startup CEO faces fraud charges after product fails to deliver.

• → Real estate company collapses when investors demand financial records.

So while you’re off for the holidays, I’ve got a challenge for you: watch something entertaining that might save your business six figures in legal fees.

I have seven show suggestions below hand-selected by me to you.

Each of these is fun to watch. Each one also sneaks in a little bit of legal education.

This wouldn’t be a good Loophole without some quick, easy, sneaky ways to teach my readers about the law when it comes to their business.

Here’s what to watch—and what to fix in your business before you’re the cautionary tale.

This Pepsi Commercial Cost Them Millions. Is Your Marketing Making the Same Mistake?

Pepsi, Where’s My Jet? (2022)

In 1996, Pepsi ran a television commercial as part of their Pepsi Stuff promotion. The ad showed a teenager landing a Harrier Jet at his high school, with the on-screen text suggesting it could be yours for seven million Pepsi Points. It was clearly a joke—or so Pepsi thought.

John Leonard, a college student, didn’t think it was a joke. He found a loophole in the promotion rules that allowed people to buy points for ten cents each. He raised the money—$700,008.50, to be exact—and attempted to claim his jet. Pepsi refused. Leonard sued.

Pepsi ran the commercial without proper disclaimers. No fine print explaining it was humor. No clear boundary between what was actually available and what was just creative marketing. Just vibes.

The case went to court, where judges had to decide a surprisingly complex question: was this an enforceable offer or just “puffery”? The answer hinged on what a “reasonable person” would believe. Would a reasonable person think Pepsi was actually offering a $23 million military aircraft? The court said no. But the case still cost Pepsi time, money, and reputation—all because they didn’t add a simple disclaimer.

As a lawyer, I love the lessons on how to advise clients to treat ads, promos, and influencer claims like legal commitments; get clear about what is and isn’t being offered; document terms and limitations in plain language—not buried in a PDF nobody reads.

It makes business owners think about:

• Your sales pages: Are you making promises you can’t keep?

• Your marketing claims: Would a reasonable person think that’s guaranteed?

• Your disclaimers: Are they actually visible, or hidden in fine print?

Watch: Pepsi, Where’s My Jet? (2022). Watch on Netflix.

Two Partners Found Gold. Only One Kept It. Here's What They Forgot to Document.

Gold (2016)

There’s a particular kind of business relationship that feels solid until money arrives. The handshake deal. The partnership based on trust. The verbal agreement that “we’ll figure out the details later.”

Gold tells the story of a modern treasure hunt—a partnership formed on optimism, big dreams, and almost no documentation. When the gold is discovered and the money starts flowing, something predictable happens: trust evaporates. Competing narratives emerge. Suddenly nobody can prove what was actually agreed to.

As a lawyer, I love the lessons on how to advise clients to never treat optimism as due diligence; define who owns what, who decides what, and how profits are split; assume every deal needs a paper trail when big money is involved.

It makes business owners think about:

• Partnerships and collaborations: Is everything in writing?

• Verbal agreements: Do you have any? Get them documented now.

• Profit splits and ownership: Could you prove your deal in court?

Watch: Gold (2016). Watch via rent/buy and streaming options.

Ray Kroc Made One Promise Outside the Contract. It Changed Everything.

The Founder (2016)

Ray Kroc didn’t invent McDonald’s, but he scaled it. The McDonald brothers created the system—the efficient kitchen, the limited menu, the replicable model. Kroc saw the franchise potential and convinced them to let him run with it.

At some point in the deal-making, Kroc apparently made a promise to the brothers: they’d get a royalty on all future franchises. It was a side deal. Outside the main contract. The kind of promise that feels solid when everyone’s excited about the partnership.

As a lawyer, I love the lessons on how to advise clients to ensure every material term belongs in the signed deal; protect brand control and core assets before scaling; understand how leverage shifts once growth is underway.

Business owners can learn the moment a “side promise” is made outside the contract, and how power and paperwork, not fairness, decide who wins.

It makes business owners think about:

• Side agreements: Have you made promises outside your contracts?

• Scaling plans: Are your terms locked down before you grow?

• Brand and IP control: Who actually owns what you’re building?

Watch: The Founder (2016). Watch via streaming and rent/buy options.

How to Build a $9 Billion Fraud (Just Skip These Four Things)

The Dropout (2019 podcast)

Elizabeth Holmes built Theranos on a simple, compelling promise: a revolutionary blood-testing technology that could run hundreds of tests from a single drop of blood. Investors poured in hundreds of millions. The company reached a $9 billion valuation. Holmes appeared on magazine covers.

There was just one problem: the technology didn’t work.

As a lawyer, I love the lessons on how to advise clients to build a culture where people can flag red flags safely; treat investor updates as legal documents, not hype; in regulated industries, make compliance and quality control first-class systems.

It makes business owners think about:

• Marketing vs. reality: Can you prove every claim you make?

• Internal documentation: Would your files help or hurt you in court?

• Compliance systems: Are you gambling in a regulated space?

Listen: The Dropout (2019 podcast). Listen on major podcast apps (ABC News).

WeWork Had a $47B Valuation Until Investors Asked One Question

WeCrashed (2020 podcast)

WeWork’s story is less about fraud and more about something equally dangerous: a massive governance gap. The company built a billion-dollar valuation on narrative, charisma, and the promise of transforming commercial real estate. When it came time to go public, the IPO process required detailed disclosures.

That’s when the problems surfaced.

As a lawyer, I love the lessons on how to advise clients that strong governance is not optional at scale; manage conflicts transparently or they will manage you; assume fundraising and public filings turn your operations into a legal record.

It makes business owners think about:

• Governance structure: Can it survive outside scrutiny?

• Conflicts of interest: Are you creating hidden liabilities?

• Financial records: Would they hold up to due diligence?

Listen: WeCrashed (2020 podcast). Listen on Wondery and major podcast apps.

Your Employment Contract Might Own What You’re Building Right Now”

Silicon Valley (2014–2019)

Silicon Valley is a comedy, but the legal issues driving the plot are real. The show opens with a central question that terrifies every founder: who actually owns the code?

Richard Hendricks builds Pied Piper while employed at another tech company. His employer, Hooli, immediately claims they own the intellectual property. The question comes down to tiny facts: When was it built? Where? Using what resources? What did Richard’s employment agreement say about IP created on company time?

The show exaggerates for comedy, but the core issues are real. Employment contracts often include broad IP assignment clauses. “Company time” can be interpreted more broadly than you think. And term sheets—even ones that say “non-binding”—create expectations and sometimes obligations.

As a lawyer, I love the lessons on how to advise clients to read their employment IP clauses before building anything on the side; document invention timelines and contributions.

It makes business owners think about:

• Your employment agreements: What IP clauses did you sign?

• Side projects: Do you actually own what you think you own?

• Term sheets and LOIs: Are you treating them casually? Don’t.

Watch: Silicon Valley (2014–2019). Watch on Max or Crave in Canada, plus purchase options.

The One Thing May Make Your Contracts Unenforceable (Even If You Paid a Lawyer to Write Them)

Let’s Simplify Legal Jargon (2010 TED Talk)

Most legal disasters aren’t dramatic. They’re boring. They happen because nobody understood what they were agreeing to.

Designer Alan Siegel makes a compelling case in this TED Talk: legalese and dense forms don’t just annoy people—they create avoidable conflict. When customers can’t understand your terms of service, they don’t follow them. When employees can’t parse your policies, they don’t comply. When contracts are unreadable, disputes multiply.

As a lawyer, I love the lessons on how to advise clients to think about how layout and wording change behavior. Clear language doesn’t just make people feel better—it makes them more likely to comply, less likely to misunderstand, and less likely to sue. Clarity is risk management.

It makes business owners think about:

• Your contracts: Can your customers actually read them?

• Your terms of service: Are they designed to confuse or clarify?

• Your internal policies: Do people understand what’s required?

Watch: Let’s Simplify Legal Jargon (2010 TED Talk). Watch on TED or YouTube (TED channel).

What to Do Before January

If you plan to take some time off and find yourself turning your mind to your business over the holidays, trust me, you’re completely normal.

If you laugh when people call it ‘holidays’, also totally normal.

Before January I’d advising thinking about cleaning your legal house – you dont need a lawyer.

1. Pick one item from the lists above to think about. Just one.

2. Fix it before the year ends.

A little secret most law firms won’t advertise? The best time to handle legal clarity is before you need a lawyer.

Copy and paste this into your AI tool of choice to get a personalized audit of what to fix before January 1st.

I'm a solopreneur running a [describe your business type and what you sell]. 

Here's what I'm currently doing in my business:
- Marketing channels I use: [list them - social media, email, ads, etc.]
- How I work with clients: [contracts, proposals, terms of service, or informal agreements]
- Partnerships or collaborations: [describe any, or say "none currently"]
- Intellectual property I've created: [courses, content, software, designs, etc.]
- How I handle payments and refunds: [describe your process]
- Disclaimers I currently use: [list them, or say "none"]

Based on these common legal vulnerabilities:
1. Marketing promises without proper disclaimers
2. Verbal agreements and undocumented handshake deals
3. Side promises made outside of written contracts
4. Gap between marketing claims and actual capabilities
5. Weak governance and undisclosed conflicts of interest
6. Unclear intellectual property ownership
7. Contracts and terms that customers can't understand

Give me a prioritized list of 3-5 specific legal issues I should address before the end of the year. For each issue, tell me:
- What the risk is
- What to document or clarify
- A simple first step I can take this week

Be direct and specific to my business model.

And on that note, I’m taking a few days off over the holidays. I’m writing it on my calendar: No computer, no work.

My goal is to show up calmer, clearer, and more creative in 2026. Because when I’m rested, I negotiate better. I scope projects better. I spot red flags faster. And I stop saying yes to things I should decline.

Let’s maximize our rest so we can have a great 2026.

Build smart,

Sonya

P.S. If you watch or listen to any of these, please let me know. I’d love to know how they came about or if they inspired you to make any changes in your business.

• He hadn’t posted in a year… so why the commissions?

• The brand was making even more money from the same video.

• One clause = one calm email… and a clear choice.

My husband’s phone wouldn’t stop

Let me tell you what happened in my house this Black Friday.

Rick’s phone was blowing up. Sale! Sale! Sale! Turns out, a coupon code was on fire.1

But he was confused—he hadn’t posted for this brand in a year.

Rick is a content creator and gets paid by brands to create content promoting their products. Last year, he contracted with a brand to promote sales during their Black Friday push. It was a great deal… or so we thought, until a few weeks ago when the ghost of Black Friday past came back to haunt us.

We dug into the brand’s account and found the problem: They had pulled his Instagram Reel from Black Friday 2024 and were running it again. Same video, same code, same adorable sales guy selling their product.

And they were making so much more money from the video in 2025 than in 2024.

Except they no longer had permission to use it.

Here’s why we weren’t scrambling (yet)

When I wrote Rick’s contract last year, I gave the brand a 30-day license. After that month ended, their rights to use the video expired.

So when they reposted it a year later, they were using unlicensed content.

Rick was rightfully upset. I was even more upset because, as you might imagine, I don’t like people being treated unfairly or ignoring the contract clauses I write. We wanted to go after them. But, more importantly, we also didn’t want to blow up a good relationship.

And this is the reality of doing business and the law: being right isn’t the same as being able to do something about it.

Court is expensive. It’s slow. It’s emotionally draining. And it’s rarely the best first move.

But because I’d built the contract correctly from the start, we had a calm recourse.

The message was simple

Rick sent one email:

“Hey team—I noticed my video is running again. I’m glad it’s working for you, but need to flag that the license is expired. Happy to discuss renewal terms if you want to keep it in rotation.”

It was Friendly. It was Professional. It set firm boundaries.

He didn’t threat. He didn’t bring in his lawyer-wife. He just pointed to what they’d already agreed to.

That clause gave him teeth

The agreement gave Rick leverage to ask for what he’s rightfully due—without needing to threaten anyone or ruin the holiday spirit.

The brand could either stop using the video or pay to extend the license. Their choice.

Without that expiration date in writing, we’d be arguing whether they even needed permission. Rick would become the “difficult” one for asking to get paid twice. What’s worse, the brand could run that video every Black Friday while their sales explode, and Rick gets nothing.

Instead, the power dynamic stayed clean. The contract said what it said.

Good content needs tight contracts

When your work performs well, clients want to keep using it.

If your contract doesn’t define what that costs and when their rights end, you’re renegotiating from scratch after the value’s already been delivered. You’ve lost your leverage.

If your contract defines those terms up front, you stay in control. The conversation stays clean.

What a good license needs to include

Three things, every time:

1. A clear end date. Not “for the campaign” or “for marketing.” An actual calendar date.

2. Usage scope. What platforms, what geography, what purpose.

3. Renewal terms. What it costs to extend, who initiates, how much notice is required.

This isn’t just an influencer problem

I see this pattern everywhere:

• Designers whose logos end up on product lines they never agreed to

• Writers whose copy gets repurposed across campaigns they didn’t know existed

• Consultants whose frameworks get rolled out to divisions that never paid for them

The better your work performs, the more it gets reused. And if your agreement doesn’t account for that, you’re working for free the second time around.

How it saved Christmas

Now on Rick’s Christmas Wishlist is an extended license. Let’s hope Christmas morning isn’t overshadowed by an unresolved business dispute.

That’s what good contracts do—they don’t just protect your work. They protect your peace.

🤖 Check your contracts 🤖

If you want to understand a contact clause better, use this prompt2:

Copy/paste into ChatGPT:

“Review this contract text and tell me (in plain English):

1. What rights the client has to use/reuse my work (where + for how long).

2. Whether it includes: end date (calendar date), usage scope (platforms/geo/purpose), renewal terms (cost + process).

3. What’s vague or risky (e.g., ‘for marketing’, ‘in perpetuity’, ‘any media’) and how to fix it.

4. A rewritten, creator-friendly license clause with a clear term, clear scope, and simple renewal option.

   
   Contract text:
   [PASTE HERE]”

Want help tightening this up?

Pull out your agreements right now. Look at how you’re licensing your work.

If you can’t point to an expiration date and renewal terms, you’re leaving money on the table.

This is my lane. I help creatives and founders build agreements that make success feel as good as walking through Candy Cane Lane.

If you want your contracts to protect your work and your relationships (and your holiday spirit), email me and tell me what you sell and how clients use it. I’ll point you to the clearest next step.

Don’t let your best work become your biggest loss.

Build smart,
Sonya

P.S. Need a coupon code for an AI birdfeeder? DM Rick on Instagram at birding_with_rick

• Laws that affect business owners in 2025

• Business Owner’s 2025 Wrapped

Friends, it’s still 2025

I don’t appreciate Spotify’s unwrapped coming out at the beginning of December…I want all my giftwrapping soundtracks to count too!

It’s still December, so technically still 2025, and I refuse to cut my year short by closing the chapter of potential too early. Given my firm opinion, I’ll share my personal year-in-review as my last post of 2025, where it belongs.

I will, however, share Canada’s 2025 in review (because Canadians are collectively coasting until the New Year) and a Canadian Business Owner’s 2025 Wrapped.

Founder’s Legal Wrapped: Canada 2025

Running a business in Canada means keeping up with changing rules—and 2025 brought plenty of them. From paperless CRA to tougher consumer protection, here’s what you need to know to stay compliant and competitive.

📧 CRA Is Going Digital-First for Business Mail

The CRA made online mail the default for most business correspondence in 2025. If you haven’t updated your email address in your My Business Account, you risk missing important notices about audits, assessments, or payment deadlines.

Action item: Log into your CRA My Business Account and confirm your email address is current. Paper mail is becoming the exception, not the rule. Missing a deadline because you didn’t get a notice won’t be accepted as an excuse if your contact info was outdated.

Learn more: CRA My Business Account

⚖️ Your Marketing and Pricing Can Now Be Challenged More Easily

Changes to the Competition Act allow private parties to sue for deceptive marketing and certain anti-competitive conduct as of June 20, 2025. This means your ads, pricing, “limited time” offers, and environmental claims are more likely to be questioned—not just by regulators but by competitors and consumers.

What this means for you: If your marketing is confusing or uses fine print that changes the real price at checkout, it may be treated as misleading. On the flip side, if a bigger player is harming your business with shady tactics, there are now stronger tools to push back.

Learn more: Competition Bureau bulletin on new private access rules

📝 Consumer Law Is Getting Tougher on Subscriptions and Long-Term Contracts

Quebec and British Columbia both strengthened their consumer protection laws in 2025, especially around fines and contract terms. If you sell subscriptions, memberships, or long-term services to individuals, you need to be very clear about pricing, renewals, and cancellations.

What to watch: Hidden fees, hard-to-cancel subscriptions, or “gotcha” clauses are more likely to trigger penalties or complaints, especially if you have customers in Quebec or BC. Using one generic set of terms across Canada without thinking about provincial rules is now much riskier.

Learn more: Stikeman overview of Quebec’s new penalties and fines

™️ Trademarks Now Reward Real Use of Your Brand, Not Just Paperwork

On April 1, 2025, new trademark rules came into force that make actual use of your mark more important. If you register a brand name or logo but never really use it in Canada, you’ll have a harder time enforcing it in the early years.

The upside: Disputes at the Trademarks Office are more structured and can come with cost awards, so they’re less casual than before. It’s also easier to clear out old “zombie” marks that were blocking newer brands.

Learn more: Osler summary of 2025 Canadian trademark changes

🤖 AI Tools Are Covered by Privacy Rules—Even Without a Canadian AI Law

Canada still doesn’t have a stand-alone AI law, so regulators are using existing privacy law to control how you use AI. If you plug customer data into chatbots, recommendation tools, or other AI systems, you’re still fully responsible for consent, security, and transparency.

What you need to know: The privacy regulator has published clear guidance on what it expects from businesses that use AI, including limits on uses of personal information. If you serve clients in the EU, the EU AI Act may also apply to your product or service—even if you’re based in Canada.

Learn more: Office of the Privacy Commissioner page on AI and privacy

🏢 Ownership of Your Company Is More Visible to Banks and Regulators

Canada’s public beneficial ownership registry and new anti-money-laundering rules made it easier to see who really owns and controls corporations. If you run a corporation, banks and government agencies care more than ever about who actually sits behind the shares, not just the company name.

Action item: Sloppy or outdated ownership records can delay account openings, financing, or due diligence for investors or partners. Keeping your shareholder and ownership records current is now a basic risk-management task, not a nice-to-have.

Learn more: Finance Canada update on strengthening Canada’s anti-money-laundering framework

📈 Capital Gains Inclusion Rate Changed (And It Still Matters)

Starting June 25, 2024, the capital gains inclusion rate increased for gains over $250,000 annually. If you’re planning to sell business assets, real estate, or shares in your corporation, this affects how much tax you’ll pay on the profit.

What you need to know: The first $250,000 of capital gains each year for individuals still uses the lower inclusion rate, but anything above that is taxed at a higher rate. This matters for business owners planning exits, corporate reorganizations, or asset sales. If you have significant gains coming, timing and structure matter more than ever.

Learn more: CRA guide on capital gains

What’s Next for 2026?

These changes reflect a broader trend: regulators are making it easier to challenge bad actors while raising the bar for transparency and consumer protection. The businesses that will thrive are those that treat compliance as a competitive advantage, not a checkbox.

Need help navigating any of these changes? Book a discovery call, and the cost goes towards the legal services you need.

Now let’s have a little fun.

Spotify Wrapped pegged me as a 71-year-old man this year. Guess that’s what happens when you fall down the poetic-beatnik-jazz-psychedelic-bluegrass-rock rabbit hole and never crawl back out. Frankly? Goals. I’m out here actively stealing the vibes from my retired parents’ Florida lanai, and I’ve never felt more alive, man.

My Spotify Wrapped made me wonder if there were a 2025 Business Owner Wrapped, what would it say? So I made one. Is it relatable?

Regular year → 8,760 hours
Entrepreneur’s year → 9,876 hours

Second most played phrase: “I really should hire someone to do this.”

“Tariffs are like extra fees a country puts on toys or goodies coming in from other countries, so those things cost a bit more when they arrive.”

Thanks, Chat-Daddy.

2nd genre: Late-night hoodie emails from bed at 11:47 pm
Featured artist: blue light insomnia.

« L’an prochain, je vais être mieux organisée. »

Maybe in 2026, we’ll all lean into the unpolished socials? One can hope.

If you’re like me and apprecialte the novel engery of a changing year, you may be interested in vision boards. I’m offering my vision board services to leaders who lack the time or energy to create their own.

Build smart,

Sonya

P.S. My word for 2025 was momentum, and sending out regular newsletters like this one helps me keep the momentum going!

P.P.S. How did you like this newsletter?

That year, I decided to read one book. My math was simple: it was a 100% improvement. It wasn’t easy, but I chose a business book, and I loved it. I’d found my genre.

From there, I aimed to gently double my reading each year: six books in 2018, twelve in 2019, twenty-four in 2020.

Since then, I’ve plateaued around twenty-four books a year — a mix of business & creative non-fiction, founder biography, and fun to read fiction — and I’m very okay with that.

So, in the spirit of loving good books, here’s a list I highly recommend for business owners. It’s organized by the specific problems you’re facing in your business. If you’re like I was and haven’t touched a hardcover in years, start simple: decide on your biggest challenge, and pick just one book to read this year. You don’t need a 52-book challenge. Let this simple and educational goal be your 100% improvement.

Oh, and I didn’t add links, so you can opt to support your local small business bookstore.

If you feel guilty charging “too much” or raising your rates, read this:

We Should All Be Millionaires by Rachel Rodgers

Rodgers speaks directly to women who have been socialized to undercharge, overdeliver, and feel grateful for scraps. She walks you through practical “Million Dollar Decisions,” scripts for raising prices, and a clear case for treating six figures as a baseline, not a fantasy. This is the book to read when you know your pricing is too low, but you keep talking yourself out of changing it.

If you avoid looking at your bank accounts, feel shame about past money choices, or treat money like a monster in the closet, read this:

Money: A Love Story by Kate Northrup

Northrup combines the inner game (stories, nervous system, self-worth) with simple outer game practices (money dates, tracking, gentle structure) so you can create a kinder, more honest relationship with money. It is especially powerful if you swing between avoidance and over-control and want money to feel like a patient partner rather than an enemy.

If you secretly believe you are “not the kind of person” who can be rich, visible, or successful, read this:

You Are a Badass by Jen Sincero

Sincero writes like a blunt but loving friend. She helps you spot where you keep shrinking, apologizing, or playing small, and gives you practical exercises to rewrite those stories. This is a great starter book if you want mindset help without heavy theory and you are craving a confidence boost that actually leads to action in your business.

If you keep hitting the same income ceiling and then sabotaging your progress, read this:

The Big Leap by Gay Hendricks

Hendricks introduces the idea of “upper limits” and the “Zone of Genius.” You see how you create drama, delays, or health issues right when things start to go well. For founders stuck under 100k, this book helps you notice where you quietly turn down the volume on your own success and how to start living more in your best work, not just your competent work.

If you are making decent revenue but never seem to have profit left, read this:

Profit First by Mike Michalowicz

This is a simple, envelope-style system for business finances. You set up separate accounts, move money on a schedule, and pay profit and taxes first. No spreadsheet degree required. If you keep saying, “I will pay myself once things stabilize,” this book provides a clear template that helps your business be healthy now, not someday.

If tax time always feels like an expensive surprise and you want to keep more of what you earn legally, read this:

Tax-Free Wealth by Tom Wheelwright

Wheelwright is a tax advisor who explains how the tax law is written to reward business owners and investors who create value. He walks through strategies around deductions, entities, and planning so you stop leaving easy money on the table. It is especially useful if you are moving from “I hope my accountant fixes it” to “I want to understand the levers myself.”

If you are spread across too many offers, platforms, and projects, read this:

Essentialism: The Disciplined Pursuit of Less by Greg McKeown

Essentialism helps you identify the few things that truly move the needle and cut the rest. McKeown gives language and tools for saying no, setting boundaries, and designing a simpler business. Perfect if you feel busy all the time, but your revenue doesn’t reflect your effort.

If you are a high-achieving woman who is exhausted and cannot see how to grow without burning out, read this:

Do Less by Kate Northrup

Do Less is written for ambitious women, especially mothers and caregivers, who are tired of pretending they are robots. Northrup invites you to track your energy, honour cycles, and design your workload more strategically. It is a great antidote if your inner narrative is “I just need to try harder” and your body is saying “absolutely not.”

If you feel like the entire business lives in your head and you are doing every task, read this:

The E-Myth Revisited by Michael E. Gerber

Gerber explains why so many small businesses fail when the owner only acts as a “technician” who does the work, not as a “manager” and “entrepreneur” who designs systems. You learn how to document processes, think in terms of repeatable systems, and prepare your business to run without you at the center of every decision.

If you feel pressure to build a big team but secretly want a lean, simple business that fits your life, read this:

Company of One by Paul Jarvis

Jarvis challenges the idea that growth always means hiring, offices, and scale at all costs. He shows how staying intentionally small can lead to more freedom, better margins, and a calmer life. Ideal if you are under 100k, value autonomy, and want permission to design a small but mighty company.

If you are overcomplicating everything and forgetting that business is about helping customers, read this:

Anything You Want by Derek Sivers

Sivers shares 40 short lessons from building his business. Chapters are 1 to 3 pages, so you can read it in tiny pockets of time. The message is simple: focus deeply on serving people, do what makes sense for you, and ignore most business clichés. This is great when you feel lost in strategies and just want to reconnect with common sense.

If you keep telling yourself “I am just not a sales person/numbers person/systems person,” read this:

Mindset: The New Psychology of Success by Carol S. Dweck

Dweck explains the difference between a fixed mindset and a growth mindset and shows how it affects everything from learning new tech to handling feedback. This book helps you catch the micro-beliefs that keep you from picking up new skills that your next revenue level requires.

If you are not sure whether to quit a project, a platform, or an offer, read this:

The Dip by Seth Godin

The Dip is a short book about strategic quitting. Godin helps you distinguish between a temporary rough patch that leads to mastery and a dead-end that will never pay off. Very useful for founders who either give up too fast when things get hard or cling to failing offers because they have already invested so much.

If you are a capable business person who still holds back, overprepares, and waits for permission, read this:

Playing Big by Tara Mohr

Mohr unpacks the inner critic, the “good student” pattern, and the ways women downplay their ideas. She offers tools for taking up more space, speaking up, and launching work before it feels perfect. Ideal if you know your stuff but still hesitate to call yourself an expert, pitch bigger clients, or share your opinions publicly.

If giving feedback, setting boundaries, or having hard conversations makes you queasy, read this:

Dare to Lead by Brené Brown

Brown brings her research on vulnerability and courage into the workplace. She gives language and practices for clear communication, grounded confidence, and building trust. Even if your “team” is just a VA and a few contractors, this book helps you act like a leader instead of a people-pleasing service provider.

If you want a simple, values-based operating system for your life and business, read this:

The 7 Habits of Highly Effective People by Stephen Covey

Beyond productivity, Covey is about character and principles. The habits help you align your goals, your calendar, and your relationships so you are not chasing random metrics. It is especially helpful if you are starting to think about the next decade, not just the next launch.

If you’re stuck, scared, or creatively frozen, read this:

Big Magic: Creative Living Beyond Fear by Elizabeth Gilbert

This one isn’t a “business book” on the surface, but it’s secretly about every founder I know who’s scared to ship, scared to be seen, or stuck waiting for the perfect idea. Gilbert is brutally honest about fear, rejection, and making things anyway. It’s the book you read when you’re overthinking your offers, your content, or your next move — and you need someone to remind you that your job is to show up, not to guarantee the outcome.

Need an AI-powered assistant to find just the right book?

That’s my list for now, but if I missed listing your exact problem, 🤖 try this prompt with your favoritte LLM tool:

You are a book-matching guide for business owners.

Your job is to help me choose ONE book that fits my *current* business problem.

First, ask me these questions one by one:

1. What’s the #1 problem or bottleneck in my business right now? (Give me examples if I’m vague.)
2. What type of help do I want most from a book? (Mindset, strategy, marketing, money, systems, leadership, legal/risk, etc.)
3. How do I like to learn? (Story-based, step-by-step, big ideas, super practical, etc.)
4. How much time/energy do I realistically have to read each week?

After I answer:

- Recommend exactly ONE book (title + author).
- In 3–5 sentences, explain *why* this book is a strong fit for my specific problem.

Build smart,

Sonya

P.S. Book I’m currently reading: The Creative Act: A Way of Being by Rick Rubin

Welcome to The Loophole, my weekly newsletter that gives solopreneurs the legal clarity they need to grow protectively and profitably — before expensive mistakes happen.

Subscribe now

Inside today’s loophole:

• Lawyer goes edgy

• Your questions about doing business by yourself

• Answers Google or Your Chat Daddy won’t give you

• CRA cares a lot

  ---

Questions

Lawyers get asked a lot of questions.

Me? Almost every conversation I have with a business owner starts with business basics.

The number one topic: sole proprietorships versus corporations.

And I’ve heard some wild ideas about sole proprietorships, so today we’re going to bust some of the biggest myths I hear every single week.

(Scroll to the end for my second most-asked question)

The conversation I have almost every day

I speak to multiple business owners every day, and most of those chats start in the same place:

Me: Soooo…., are you incorporated?

Biz Owner: Nope. I’m a sole proprietorship. I’ll incorporate when I’m serious.

Or even,

Me: Tell me about your business

Biz Owner: It’s doing great! Money coming in! But I don’t really have anything set up, so it’s not a real business yet.

Ahem.

In my meetings with clients, I’m very gentle, but here at The Loophole, I can get a little edgy, so I’m going to give it to you straight.

“Friend, you already have a legal business setup. It’s a sole proprietorship. Stop pretending you don’t.”

Whether you like it or not, if you create anything for monetary value and get paid, without an employer, you already have a sole proprietorship. And a sole proprietorship is a legal thing.

What’s really going on with sole props in Canada

One of my favourite fun facts: the moment you carry on business for your own benefit and no one else is involved, like an employer, you have a sole proprietorship. Ta-da! Instant business!

So if Mary Joseph sells cookies at a holiday market this year, she’s automatically selling them as a business called “Mary Joseph.”

Even if the cookie sale feels small and casual, CRA and business law have already kicked into gear.

{A sole prop isn’t completely “automatic” though. You may not need to register a business name if you trade only under your exact legal name, but once you add words like “Consulting,” “Studio,” or “Kitchen,” you usually must register that name.

Take it from a lawyer: “I never registered” is not a defence if there’s a problem later.}

The big questions I hear every week

Here are the questions based on common myths that cause the most trouble:

❓Can I just start as a sole prop and incorporate later when I’m more serious?

No—incorporate now if you want to build something real. You don’t need to “earn” the right to incorporate.

More often than not, it makes sense to incorporate from day one. You do not have to “earn” the right to incorporate by starting as a sole proprietor first.

Any business owner I work with, I look to incorporate ASAP because it’s not just a legal structure; it’s a mindset. Legally, it makes sense if they plan to build something that can grow profitably, is tax-beneficial, helps limit their risk, and may be sold one day.

Mindset-wise, my favourite mantra applies: begin with the end in mind. Starting out as a corporation trains your habits and posture to act big before you are big.

❓Do I need to register my business name?

Yes—if you’re using anything beyond your legal name, you probably need to register it.

You cannot simply choose any business name and skip registration. Name registration is how the province and the public know who is behind the business.

If Mary trades under “Mary Joseph,” she may not need to register. The moment she calls her business “Mary’s Kitchen,” she’s using a business name that generally must be registered with the province. Ignoring this can lead to problems with banks and suppliers, and, in some cases, fines.

❓Is filing taxes the same as when I was an employee?

No, you now have to track income and expenses and calculate your own profit. It’s more work.

For taxes, a sole prop owner’s return is not the same as a T4 employee who just plugs in a slip and moves on.

You still file a personal T1, but now you have a business section with its own rules, deadlines, and record-keeping. You have to report all business income and expenses, keep books and records, track instalments, and, in some cases, meet different deadlines. You are responsible for calculating your profit, not just reporting what someone else paid you.

❓Can I write off anything I buy for my business?

No—only reasonable expenses actually used to earn income count. CRA cares what you bought, not which card you used.

Not every “business” purchase is deductible. An expense must be reasonable, incurred to earn business income, and supported by receipts and records.

Some categories—meals, vehicles, home office, big equipment—have extra limits or special rules. Tossing everything on the “business credit card” does not magically turn personal spending into tax write-offs. CRA cares about what you bought, not just which card you tapped.

❓Do I need to charge GST/HST?

Yes—once you hit $30,000 in revenue, you must register, charge, collect, and remit GST/HST.

Collecting taxes is not just for corporations. Once your total worldwide taxable revenues from all your sole prop activities cross $30,000 in a 12-month period, you must register, charge, collect, and remit GST/HST.

But, I recommend my clients register when revenue is still at $0 because:

1. It’s easier to build the admin habits from the beginning,

2. optics—you look more legit when you’re billing clients,

3. regular bookkeeping and quarterly remittances help you act like the CEO you’re becoming, and

4. Business owners who face tax reality early have fewer tax problems down the road.

❓Can I pay myself a salary?

No, you and the business are the same person. You can’t be your own employee or deduct your own salary.

In a sole proprietorship, you and the business are the same legal person. You cannot be your own employee and deduct your own “salary” as an expense.

The business earns profit; you pay personal tax on that profit. Money you pull out is just a draw, not a deductible wage. Payroll for yourself only becomes an option when there is a separate legal entity, like a corporation.

❓Are my personal assets protected?

No—zero protection. If your business gets sued, they can go after your house, savings, everything.

A sole prop has zero liability shield. Simply calling yourself a “business” does not create a barrier.

If someone claims Mary’s cookies caused them harm and sues “Mary Joseph’s Kitchen,” any liability is Mary’s to pay. Creditors can go after her personal bank accounts, investments, and, in some situations, her home.

To manage that risk, you look at business insurance, careful contracts, and talking to a lawyer about incorporation.

❓Can I just use my personal bank account?

Technically, yes, but it’s a terrible idea. CRA needs clear records, and mixing accounts makes everything harder.

Here’s my myth buster of all myth busters: CRA cares a lot. They care about clear, supportable records.

Yes, you’re technically allowed to use a personal account for business, but it’s a terrible idea.

Mixing everything together is like a pumpkin-spice-sea salt-mustard-sugar cookie: it will give you indigestion and worse.

A single mixed account makes it harder to prove what’s business and what’s personal, increases the risk of missed deductions, and makes any review or audit more painful. A separate account for business income and expenses is basic best practice, even for a tiny sole prop.

❓Can my partner and I share one sole prop?

No—two or more people means you need a partnership agreement or a corporation.

Let’s get some English language straightened out: “sole” means one.

If two or more people own and run a business together, they’re in partnership territory, or need to look at incorporating. Partnerships have their own default rules, risks, and tax treatment.

That usually means a proper written partnership agreement or a corporation if you’re building something with someone else. You cannot stretch a sole prop to fit multiple owners.

🤖Have a robot help figure this out🤖

If you’re in Canada and you sell your own stuff, you’re not “playing business.” You’re in business.

And that means the rules of sole proprietorship already apply to you, whether you’ve thought about them or not.

It’s time to understand the legal implications of your side gig.

Copy this into ChatGPT or Claude:

“You are a Ontario business lawyer. I run a business in Canada. Help me figure out my next best step.

Here’s my situation:
The name I use with clients is: [fill in]
My business income goes into: [personal account / separate business account]
My annual revenue is roughly: [amount]
Number of people involved in the business: [just me / me and a partner]
Current structure: [nothing set up / sole prop / incorporated / not sure]
Based on this, what’s the single most important thing I should do next to get my business properly set up?”

When you’re ready to have a human help (and yes, I am very human), I have a few slots available for a legal discovery call. The cost of the call is applied to any legal products you buy in the future.

Build smart,

Sonya

P.S. Why this almost newsletter became the “Soccer Pirate Ship” issue.

More than any legal question, people ask me about my Substack.

They often want to know: “Sonya, what’s your writing process like?”

Mine starts with a transcript. I speak into my phone and talk through, then I go back and format them later. For this one, I was talking all about “sole proprietorships,” but my transcript app turned it into “soccer pirate ship,” which I think I love.

Because if I think about it, when you run a sole prop in Canada without understanding any of the legal, it can feel exactly like you’re captaining a very chaotic soccer pirate ship.

Welcome to The Loophole, my weekly newsletter that gives solopreneurs the legal clarity they need to grow protectively and profitably — before expensive mistakes happen.

Inside today’s loophole:

• Ozzy

• Changes

• Why I’m simplifying to protect your business

I was driving, half-listening to public radio, when I heard the words “newly departed Ozzy Osbourne.”

Black Sabbath’s heavy metal is not my genre at all. But then the host told the story of their one song — “Changes,” a quiet piano ballad from a band known for loud guitars and doom. By the time the song ended, that song had quietly moved into my brain and become my current business theme song.

When heavy metal went soft (and won)

In 1972, Ozzy’s band Black Sabbath did something that felt downright wrong to them: they recorded “Changes,” a gentle piano ballad with zero guitar, zero drums, and a very tender lyric about heartbreak.

They were the heavy metal guys. “Changes” was… not that.

It started as a late-night improv on a piano that their guitarist couldn’t even play. As the guitarist poked away with some awkwardly choppy chords, the other band members piled in with melody and lyrics. The song felt weird, risky, off-brand, but they recorded it, and it quickly became a fan favourite.

“Changes” became a turning point in the band’s popularity, because it showed what else they could be.

Meanwhile, I’ve had “I’m going through chaaaanges” on repeat — walking the town before sunrise, washing dishes, outlining contracts. Not because I’m going through a break-up [Rick, we’re all good] but because some clarity is opening up in my business.

The expensive silence between “just starting” and “lawyer up”

Over the last few weeks, I’ve been doing short 15-minute chats with founders and creators. I ask them hard questions about how they approach legal in their business. And I keep hearing the same thing: They didn’t.

The explanations all sound like…

• “I just wanted to start rolling in my business.”

• “I was too small to worry.”

• “I didn’t know what I didn’t know.”

• “I copied my mentor’s framework — they’re fine, so I figured I was fine.”

But I’ve also connected with business owners further down the road in my law firm practice… in hot water. Messy client disputes, unclear IP, partnerships gone sideways, platforms they don’t control.

I keep seeing the same pattern: there’s a big empty space between “I’m starting” and “I’m ready to hire a lawyer.” That gap is where expensive omissions grow quietly in the dark.

Here’s what really gets me: founders think legal and structure are for “later,” once they’ve “made it.” But the problems that blow up at 250K usually start at 2.5K.

My own version of the piano ballad

As I’ve been singing along to “Changes,” I realized I’ve been doing a softer version of the same thing as Black Sabbath — quietly improvising, testing, tinkering, but not fully owning the new sound.

So I made a decision: clarify my brand, my offers, and who I’m here for. Simplify everything so protection and peace of mind are easier to get.

That’s the gap I’m here to fill: the lawyer before you need a lawyer.

I’m doing that with the right level of education, structure, and strategy so you can grow simply, protected, and profitably. Even — especially — for the solopreneur who still feels “too small to worry.”

My new setlist

Here’s what that looks like:

The Loophole (this newsletter). Weekly, plain-language stories, horror tales from businesses that skipped the basics, how-tos, checklists, and simple levers even the tiniest business can pull to get more protected and more profitable.

Online trainings. I’m starting with live, affordable sessions for solopreneurs and creators who want the essentials done right—not perfectly, not expensively, just right. Think: “Vision to 250K,” “The First 6 Months: From Sole Prop to Safe Inc,” and “How I Build an Uncopyable Business.”

The Quarter Million Ready Quarter. 90 days to go from solopreneur to CEO. Very limited, applications opening soon. For founders under 100K who are serious about hitting 250K — and keeping it. Over 90 days, we’ll map your next-quarter priorities, de-risk your offers, hiring, and IP, and design a business that actually fits your life, instead of swallowing it whole.

Does it feel a bit weird to say “this is what I do now”? Absolutely. But, like Ozzy, I think the fans are going to love the new sound — pared down but more beautiful.

If you’re also going through changes

Simplifying my offerings isn’t just an exercise in branding (which I’m DIYing and kinda mailing it in for now because it isn’t what’s important). It’s protecting my scope of work and honing in on my profit strategy.

The process I’ve taken to get here has meant quietly assessing who I am, my strengths, my genius, taking a hard look at my time and what energizes me versus what drains me.

Here’s how you can do the same:

1. Audit your energy, not just your revenue. For one week, track every client interaction, every offer you deliver, every task. Mark each one: ⚡ (energizing), 😐 (neutral), or 🔋 (draining). The patterns will tell you what to keep, delegate, or kill.

2. Name the ONE gap you fill. Not three. One. What do people need right before they think they need you? That’s your gap. Mine is “the lawyer before you need a lawyer.” What’s yours?

3. Use this prompt to clarify your offers. Copy this into ChatGPT or Claude and fill in the blanks:

GPT Prompt: Simplify My Business Offers

I’m a [your role] who serves [your ideal client]. Right now I offer [list everything you sell or do]. But I’m feeling scattered and want to simplify.

My genius zone is [what you’re naturally great at]. What energizes me is [types of work that light you up]. What drains me is [types of work that exhaust you].

Help me:

1. Identify which offers protect my time and amplify my strengths

2. Spot what I should stop offering (even if it makes money)

3. Suggest 2-3 core offers that are clear, profitable, and aligned with my energy

4. Write a one-sentence positioning statement that names the gap I fill

The real lesson I want every solopreneur to remember from “Changes” is sometimes the quietest shift is the one that changes everything.

-Sonya

P.S. My website is still in the works (see: DIYing and mailing it in), but if you’re a founder under 100K who’s serious about hitting 250K — and keeping it — email me to get on the waitlist for the VIP Business Strategy container. I’ll send you details about the application process and what we’ll build together over three months. Just hit reply to this newsletter. First come, first considered.

Calling all business owners! I’m hosting 15-minute Zoom chats this week to learn what’s confusing or annoying about legal tasks in your business, no matter the stage of your business. I have a few slots left. As a thank you, you’ll get my Legal Health Check checklist and a summary of what I learn from the research. If you’re up for joining the 30+ business owners who have already participated, book our chat here: sonyaszabo.as.me/15-min-chat

Forward this to the friend who keeps saying “please” to their chatbot.

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The morning I thought my husband could read my mind

I declared this Saturday my “stay-in-bed-as-long-as-possible” day. My husband, Rick, would have joined the challenge if not for his enduring coffee addiction. Caffeine called, and I won the challenge from the best vantage point in the house.

On his way to the kitchen, Rick offered to bring me a beverage. “Thanks so much,” I said. “Can you please make my usual morning starter drink?”

Eager to secure his title as Best Husband for the 26th year running, he hopped out of the room like a contestant on a game show. Two minutes later, he reappeared, head low. “What the heck is your morning starter drink?”

I explained: water heated to 50°C, lemon, and one quarter teaspoon of Celtic sea salt. He hurried off again, equipped with my now precise instructions.

Two minutes later, he returned sheepishly. “Where are the lemons? Where’s the salt?”

This was on me. I hadn’t given enough information.

Once I told him exactly where to find everything, he nailed it. And, to boot, he made the best version yet of my warm morning Gatorade.

I used to talk to AI like it could read my mind too

I used to prompt AI the same vague way: “Summarize this” or “Draft a proposal.” Then I felt disappointed. Tools are not spouses. They cannot infer. They do not know where my “big blue pouch” is or anything about my business unless I tell them.

They follow instructions, not hints.

If you want useful output, stop being nice and start being exact.

How to talk to AI like a builder

You are not wooing a spouse. You are bossing a robot around. Be clear, firm, and specific. Here is how I talk to AI now. Spoiler: it is very different from how I talk to my husband.

Use a command voice, not polite hedging.
❌ “Hi! If you don’t mind, could you please summarize this when you have time? Thank you so much. Love ya!”
✅ “Summarize this thread in 5 bullets. Your task is to follow the rules below. You must keep it under 120 words.”

Define the reader and the depth.
❌ “Write a summary for everyone.”
✅ “Write for a time-starved founder with little technical background. Explain at a beginner level.”

Break big work into steps.
❌ “Create a launch plan.”
✅ “Step 1 list risks. Step 2 outline a 90-day plan. Step 3 assign owners.”

Use do language.
❌ “Don’t be vague and don’t ramble.”
✅ “List the top 5 risks. Return one line per risk with impact and mitigation.”

Provide a quick example.
❌ “Write good subject lines.”
✅ “Example style: ‘Your launch timeline and next steps.’ Give me 5 like this.”

Structure the prompt and fence the data.
❌ Paste chaos and hope for the best.
✅ “### Instruction … ### Context … ### Data … ### Example … ### Questions. Use only the content between <<<data>>> and ignore everything else.”

Make constraints explicit and centralized.
❌ “Try to make it sound good and professional.”
✅ “### Constraints: 150 words. Warm, confident tone. Three short paragraphs. One CTA. Headings allowed. For long form, 600–700 words with one story and one takeaway.”

Block fiction and control uncertainty.
❌ “Fill in any gaps however you like.”
✅ “You will be penalized if you invent facts. If unsure, ask up to 3 clarifying questions, then proceed.”

Ask for natural, human-like writing.
❌ “Compose in advanced legal terminology.”
✅ “Plain language. Short paragraphs. No insider jargon.”

Allow questions, then require delivery.
❌ Endless follow-ups that stall the work.
✅ “Ask up to 3 clarifying questions until you understand. Then deliver the draft.”

Assign a role.
❌ “Help me with this.”
✅ “Act as my small-business lawyer reviewing a client contract.”

Iterate on purpose.
❌ “Looks fine.”
✅ “Improve clarity and tighten by 20 percent. Keep my voice. Strengthen the opening hook.”

Protect the author’s voice during edits.
❌ “Rewrite however you want.”
✅ “Edit for clarity and grammar only. Keep my voice and rhythm.”

Copy and Save this Bossy Boss Prompt

### Instruction
You are my [role]. Your task is to produce [deliverable]. You must follow every rule below.

### Audience
[who it is for; level]

### Context
Only use the material between <<<data>>>. Ignore everything else.

### Format
[type, word count, tone]

### Constraints
- No invented facts. If missing info, ask up to 3 questions, then proceed.
- Short paragraphs. Plain language.
- Include [CTA/headings/subject line].
- End with one sentence that repeats the main point.

### Example
[paste 2–4 lines that show the style]

### Data
<<<data
[paste source text]
data>>>

### Quality checks
Before final, list 3 checks you ran and how the draft meets them.

Use this once. Watch your output improve. Then make it your default.

The ending you can act on

Give AI the recipe and the cupboard map. Do not hope it guesses. It’s not your husband who comes back and asks for clarification. If you want useful output, stop being nice and start being exact.

Take your last polite prompt. Rewrite it with the Bossy Brief. Run both and compare on usefulness, time saved, and confidence.

I hope this helps!

—Sonya

P.S. This blog is going through changes. Next week I’ll be rolling out a new name, new focus, and new branding. Only for the better, I promise. Watch this space.

P.P.S. I’m building something to help business owners but I need your input. Let’s chat: sonyaszabo.as.me/15-min-chat

P.P.P.S. I made it to 11:00 a.m. before I had to brave the world outside my bedroom.

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This week, three different people—on three different Zoom calls—complimented my bookshelf.

Apparently, it looks very organized.

I said thank you, of course. But what I was thinking was: “If only you knew.”

Because that same bookshelf has been driving me crazy.

Twice this week, I went hunting for something I knew was there.

First, a book I wanted to share with a client. Gone.
Then, a photo of me as a little girl that I needed for a weekend retreat. Also gone.

I thought I’d find them in thirty seconds, but it took thirty minutes of flipping through albums, binders, and stacks of papers—nothing.

So yes, my bookshelf looks calm and collected on camera, but behind the scenes? It’s more “creative tornado” than curated library.

All this searching for lost things got me thinking about another kind of organization—how I keep things straight in my business. Especially the part that no one sees: how I use AI.

I thought I’d share the five ways I, a self-declared business management expert, lawyer, manager of a content-creation business, and easily distracted founder, organize my AI.

1. I Have a Chatbot That Actually Knows Me

I have a paid ChatGPT account with a custom profile that knows who I am, what I do, and how I like to be spoken to.

I can even tell it things like “never use an em dash.” (Does it listen? Not really. But a girl can dream.)

Having that setup means I don’t have to start over every time. It already knows my tone, my clients, and my weird fondness for parenthetical thoughts.
I also named it. Because, let’s face it, the thing is like a new puppy, houseplant, or car: it needs a name.

2. I Make Projects, Not Piles

When I’m working on something that takes time—like a workshop I’m planning—I keep all those chats inside one project.

That way, when I come back to it weeks later, I don’t have to re-explain what we were doing. I just pick up where I left off.

It’s like having perfectly labelled little file folders for all my ideas and chats rather than leaving all the papers spread out on the kitchen table.

3. I Automate My Repeatable Tasks

I’ve created dozens of custom GPTs for my repeatable tasks.

For example, my “Future Sonya” GPT. This one feels a little woo-woo, but it works. I loaded it with my values, goals, and priorities.

When I’m stuck on a decision, I ask her what she thinks. She doesn’t predict the future, but she reminds me of what matters most to me. It’s like talking to my wiser self on days I don’t feel very wise.

Others include GPTs that help me write titles and scripts for content creation, format my Substack (hi, you’re here), and stay consistent with my business values and voice.

4. I Reuse Prompts That Actually Work

Prompting is everything—it can make the difference between brilliance and gibberish.
So I keep a little library of good ones in a Notion database.

Things like:
• the prompt that helps me write better prompts
• the one that checks my grammar without changing my voice
• and the one that turns messy notes into something readable

It saves me from reinventing the wheel—and gives me more time to do things like search up and down for books and photos.

5. I Keep Learning About What I’m Using

I try to stay curious about what these AI tools (LLMs, to be more accurate) actually are. They’re not magical beings whispering universal truth. They’re just systems trained on a lot of data, and it’s risky for business owners to forget that.

The tool can be powerful, but equally dangerous if used without understanding.

So I read, follow the news, and keep an eye on how AI is being used in business and law. For me, learning how things work is part curiosity, part self-protection.

Organized Workflow = More Time to Organize My Life

My bookshelf may look organized, but clearly it has room for improvement. So does my workflow.

Little by little, I’m finding systems that save me from the thirty-minute treasure hunt—whether it’s for a missing book or a half-finished idea.

Maybe you’ll try one of these too. Because when you spend less time searching, you get more time for the good stuff: deep conversations with your sister, fresh fall air, or just sitting still long enough to enjoy watching a great sports game.

✅ Check your AI organization system with this prompt:

Act like business strategist and AI workflow nerd.

Use this 5-part framework (custom profile, projects, automation, prompt library, continuous learning) to audit how organized my AI use is.

Ask me 10 yes or no questions, rate my system from 1–5, summarize what’s working and what’s messy, then give me 3 simple fixes I can try this week.

Keep it friendly, practical, and a little cheeky.

—Sonya

P.S. I found the book. It was in my nightstand. I still have no idea where the photo is, so I snapped a picture from an old scrapbook and had it printed at Walmart. So really, the disorganization cost me even more time and thirty-two cents.

P.P.S. This is part of a series on The Expert AI Mindset for Business. Next week, I’ll share how I talk to ChatGPT based on the latest research.

P.P.P.S. Go Blue Jays! 🐦

💌 If this made you think, forward it to a founder who still thinks “AI lies.” Because maybe, like me, they just need better instructions.

The Day My Chat Friend Lied to Me

This summer, I almost gave my daughter very wrong legal advice.

She’s in her second year of university. She’s newly independent and the proud renter of her first “single-lady” apartment (cat and all). She pays rent on time and keeps a spreadsheet for her budget. She is, in every way, a responsible adult.

Her landlord, however, is not.

One night, walking home from work, she lost her mailbox keys. Not a big deal, right? Until her landlord demanded payment equivalent to her entire monthly paycheck for a replacement.

The same paycheck that was, ironically, stuck in her mailbox.

So she did what any smart university daughter of mine would do—she sicced her lawyer mom on him.

Her lawyer mom (that’s me) sat down to write a firm, righteous letter reminding him of his legal obligations and moral deficiencies. But before hitting “send,” I did what every modern woman does when she’s too tired to research case law at 10 p.m.

I asked ChatGPT to draft it.

That’s when AI scared the poop out of me.

I asked the bot to cite the law on replacement keys in Ontario. It responded confidently, like a first-year associate trying to impress a senior partner:

“Under section 23(4) of the Ontario Residential Tenancies Act, a landlord may not charge more than the cost of replacement.”

Perfect, right? Lawyering is so easy nowadays, right?

Except…I knew better. So I pulled up my big lawyer pants and did my own AI-free research.

You may be surprised to hear what I learned:

→ a) Section 23(4) doesn’t exist, and
→ b) The only thing the law says about keys is that landlords can’t change the locks without giving tenants a replacement key.

The “source” it cited? A random PDF from a real-estate conference in 2011. Not a statute. Not even close.

I pushed back. I politely told ChatGPT it was wrong. But it doubled down.

Rude!

Such a liar!

To add insult to injury, if I hadn’t double-checked, my chatbot would’ve had me send a legal letter full of imaginary law… on behalf of my own daughter. 😳

TBH, this scared me so much my first reaction was to tell the world to stop using AI forever.

But after I calmed down, I realized two things I want every business owner to know:
1️⃣ AI hallucinates.
2️⃣ Humans need to use AI better.

AI Didn’t Fail Me. I Was Just a Bad Boss

Why does this matter for business owners? Because AI didn’t lie to me. It did exactly what I told it to do. It found words that sounded right and delivered them with confidence.

AI doesn’t know truth; it predicts patterns. It’s a mirror that reflects our instructions.

When people say “AI hallucinates,” what they really mean is: we gave it too much room to guess.

And that’s exactly what I’d done. TBH, my prompt was lazy.

I Needed to Train Myself to Talk to the Bot

The next morning, I started over with a real prompt.

And just like that, my “hallucinating” assistant became a capable researcher.

And that’s the lesson for us business owners: AI isn’t dangerous. Vague leadership is.

Founders talk about delegation all the time, but most of us are bad at it.

We hand over chaos and expect brilliance—from employees, contractors, or now, robots.

The fix is the same across all three: clarity.

AI is the world’s most obedient, eager intern. It will do exactly what you ask—and throw in a few bonus surprises if you don’t give it boundaries.

If you tell it, “Go write something amazing,” it’ll proudly return nonsense and ask for a pat on the back.

But if you define the job, the scope, and the standards, it’ll exceed your expectations every time.

Lesson Learned. Going Forward I Will Be Clearer.

I almost embarrassed myself in front of my own daughter by sending a legally inaccutate letter to her landlord.

But the scare taught me a bigger lesson about leadership.

Business owners who avoid AI because it “hallucinates” are missing the point.

AI doens’t suck. How they treat it does.

Business owners need to treat it like an eager intern who can read your mind only if you teach it yours.

➡️ Learn how to train AI.
➡️ Learn how to talk to AI.
➡️ Learn how to correct it when it’s wrong.
➡️ Practice double-check its work (just like you would with any human)

And then it will be your best #1 🏆 employee that deserves every pat on the back you can give it.

🧠 Try This with AI

Copy + paste this before your next task to turn a hallucinating robot into your most reliable assistant:

Before completing my request, ask me:
1. What’s the goal?
2. Who’s it for?
3. What format do I need?
4. What tone or style should it use?
5. What facts must it check or verify?

Once I answer, restate my brief to confirm you understand—then begin.

💌 If This Hit Home…
Forward this to a friend who’s still afraid of “AI lies.”
Because maybe, like me, they just need better instructions.

Thanks for reading!

-Sonya

P.S. Before we could put up a big stink with the stinky landlord, my daughter found her keys in a coat pocket.
P.P.S. This is part of a series about AI for business owners. Next week I’m very excited to share my exact guide on how I train my AI for my business and then the next week I’ll share how to talk to AI (based on the latest research).

Share

• The Monday I realized my “helpful” robot was wrecking my week

• How I stopped treating AI like an intern and trained it to think with me

• A copy-paste AI prompt to help you build one calm, repeatable system

• A 1-minute poll to improve this Substack

The Monday I Fired My Robot

A perfect plan built by AI. A perfect disaster by 11 a.m.

It was a Monday morning, and I was already behind.

When I feel overwhelmed, I like to do what I call a brain dump. I grab my journal and my favourite roller pen, set a timer for 10 minutes, and make headings—home, business #1, business #2, personal. Then I list everything on my mind.

Once it’s all out, I analyze and schedule each task into my week.

This Monday’s brain dump started the usual way—paper, pen, journal, timer—but with one new, spicy ingredient: AI.

After listing the 10,735 things I wanted to get done that week, I opened ChatGPT, dumped in my chaotic list, and asked it to organize my week.

Seconds later, it handed me a pristinely formatted plan with perfect headings. I copied it straight into my calendar.

Then I tried to live it.

By 11 a.m., the plan had collapsed.

The robot took what I told it and spat out what I asked—but not what I needed.

The list didn’t align with my creative flow, energy levels, or my desire to sleep, eat, and move my body.

It was efficient. It was AI-built. But it wasn’t me.

The Real Problem Wasn’t the List

I wasn’t failing at productivity—I was delegating without direction.

Like many founders I know, I was using AI the wrong way—treating this powerful tool like a clueless intern with a clipboard.

And the clueless intern always obliges.

We all start there. We open our first chatbot and treat AI like a faster search engine. And it obliges. It even says “you’re welcome.” It even suggests what else it could do.

We ask for quick fixes instead of building real systems.
We use it to get through the day instead of designing how we work.

I wasn’t alone. Every founder I speak to is using AI like Google: type a request, skim, copy, paste, move on. They never train it, refine their prompts, or connect tools. Each use is a one-off instead of part of a workflow.

Too many founders are staying on the surface of what AI can really do for their business.

The Clueless Intern in My Laptop

AI will mirror your thinking. The problem is, most of us haven’t taught it how we think.

The real problem is how we think about our little laptop robots.

We see AI as an eager intern, not our savviest COO.

We don’t teach it how we think, what our priorities are, or how we like to work.

But for business owners, that’s where its real power lives.

The Pivot: From Tasks to Systems

The day I stopped asking for answers and started building workflows that think with me.

Once I saw the gap, I became determined to harness the ROI of my $20/month subscription.

I stopped using AI for random tasks and started building small, reusable systems.

Here’s what that looks like:

• I built custom GPTs for the work I do most often

• I created reusable prompt templates

• I taught it about me and my business values

• I kept my workspace organized so each project has its own knowledge bank

• I trained it on my writing voice

• I built my own creative department

• I trained it to work without me

The New Brain Dump

Same pen, same journal—completely different outcome.

This Monday, I sat down again—pen, journal, timer.
But this time, instead of asking ChatGPT for a to-do list, I asked it to analyze my 15,957 wanna do tasks based on what it knows about me.

I wanted my week built around:

• my business priorities

• my routines and boundaries

• my energy and values

Then it created a calendar I could upload straight into Google—complete with redone time blocks and realistic workflow.

It even eliminated tasks that didn’t match my capacity or goals.

In under 15 minutes, when I treated my chatbot not as my intern but as my operations partner, I got a realistic schedule I can actually stick to.

Your Turn

Stop using AI for quick fixes. Start using it to build the calmest business you’ve ever run.

If you’re only using an AI chatbot for basic outputs, you’re missing its real power.

AI isn’t for quick fixes. For business owners, it’s the most powerful tool we have for building structure and systems—without expensive software or full-time staff.

Start small. Try this:

“Help me turn this messy task into a repeatable system I can use every week.
Ask me questions to learn how I work before you create it.”

Let it interview you. Let it learn your rhythms. Let it build with you.

One small workflow today can become the foundation of a calmer business tomorrow.

Sonya

P.S. This is part of my ongoing series on using AI with intention for small to medium business owners. In the coming weeks, I’ll break down each way I use AI—and end with a piece on how I don’t use it (including what it means to use AI ethically).

P.P.S. I’m curious—how are you currently using AI?

Thanks for voting! I’m using your answers to shape next week’s letter (and maybe a new AI prompt or two).

Want to share more? Tell me how you’re using AI in the comments.

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