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The biggest risk
10 years ago, I called my boss to tell him I’m quitting to become self-employed.
One of the scariest calls I’ve made in my entire life.
It was my first reliable job with future promise.
I’d walked away from crappy jobs in the past with no safety net and always figured things out. But in this case, rather than finding another job (easy), I was going out on my own (complete uncertainty).
And as I would come to find…
Definitely not easy.
But totally worth it.
At the time, I owned three power tools and instead of a truck I was driving around my sisters old Ford Focus hatchback, but I was a carpenter, I had skills, and I was starting my own business.
I remember taking the extra cash from my first side gig to buy two big, important tools off craigslist and trying to cram them in the back of my tiny car with the previous owner saying, “You don’t have to take them both at once, you can pick the other one up tomorrow!”
I can’t remember if i got them both in, but I was excited.
Until I wasn’t.
I’d tried and failed to start businesses before, but this one was different.
Deep down, I knew I wanted to build something online around my interests, but since I had no idea where to start, I chose the “sure thing” (a construction business). But for some reason it always felt like wearing a ill-fitting suit to prom. It just didn’t feel right, and everyone could tell.
I’d overcome lots of physical and mental health challenges in my days.
Preferred to spend my time reading, learning, and writing.
And I was obsessed with time in nature, technology, holistic health, and understanding what motivates people to change.
The construction thing always paid well, but it was never what I was truly passionate about.
So after the initial excitement of starting and marketing a new business wore off, the reality of my disinterest set in. Unfortunately, I was $80,000 in debt before I realized that if I’m going to take a big risk and work that hard on something, it might as well be something I’m truly passionate about.
And that’s when I finally decided to take my chances at teaching online.
It wasn’t long before I made my first digital dollar.
But it did take years to hone in, find my niche, and make it truly sustainable. My only wish is that I started sooner.
If I could go back in time and teach my younger self one lesson, it would be this:
The “sure thing” is the thing you’ll stick to when things get hard.
For me, that turned out to be marketing… the thread that quietly connected all the things I was truly obsessed with.
Exploring, writing, building online, and helping people turn meaningful ideas into something real so the world looks a little bit more like the kind of place I want to live in.
But what about you?
What’s the idea you keep circling in your head?
The thing you read about late at night?
The work you’d gladly spend hours on if no one was watching?
Who do you admire?
What problems do you naturally notice?
What do people already come to you for, even if you’ve never charged for it?
Because that’s the signal. Work isn’t supposed to feel like resistance. It’s supposed to feel engaging, meaningful, and alive. And even when it’s hard, it’s the right kind of hard.
And inside the Client Discovery Lab, we’ll uncover precisely where your interests, experience, and energy actually intersect with real market demand, so you’re not guessing at next steps for years (the way I was).
If that sounds like a conversation worth having, you can join the waitlist here and I’ll reach out in a few days with more details:
Plus, all who apply get something useful even if they don’t end up joining the cohort.
More soon,
Kevin Hood