5 Times This Lawyer Took Shortcuts in 2025 (Number 4 Cost Me Thousands)

My 2025 year-in-review, complete with bad contracts, worse bookkeeping, and one spectacular wipeout

In this issue of the loophole:

• 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.