The Boss You’re Becoming When You Incorporate
One question to ask to decide to know when it's time to incorporate
In this edition of The Loophole:
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.