Wherever I Go, I Don’t Feel Like I Belong
Why every step forward still feels a step out of place.
Hi friend,
This is my career progression over the past 5 years:
corporate —> labourer —> solo entrepreneur —> buying into a larger business
Nothing fancy, right? But, I’ve noticed a pattern recently.
No matter where I am in my life, what I’ve accomplished or learned, I can’t seem to shake the feeling that I don’t belong.
Let me walk you through the imposter syndrome I’ve faced at every transition point.
Transition #1 (corporate —> labourer)
In 2023 I quit my corporate sales job (because the thought of even one more cold call made me want to jump off the side of my office building) and decided to landscape in a family friends business.
We built patios & fences, chopped down trees, cut grass, etc. All that jazz. It was textbook masculine work.
Despite that, I kept feeling like I wasn’t “manly” enough to be doing this. I felt like any time someone looked at me, they knew I was a fraud. Just some boy trying to convince himself he was a man.
On top of that, it wasn’t even my business. I was just a labourer.
But not for long.
Transition #2 (labourer —> solo entrepreneur)
Later that year. I started my own landscaping company. I wouldn’t be just an employee anymore, I would own the whole thing.
I knocked doors to get my first customers. I fulfilled work. I even hired an employee by the end of the year. I was, by definition, an entrepreneur.
But when people asked what I did I would tell them, “Oh, I just run a landscaping company”.
"Just”
That was the word that always killed me.
All of my friends, friends of friends, friends of friends of friends have super impressive, high paying careers.
Investment banking. Private equity. Corporate real estate. Lawyers.
All the careers your mom is really excited to tell her friends about. The sexy jobs.
But despite actually running a business. Turning complete strangers into recurring customers. Creating money from seemingly no where. I was embarrassed to call myself a business owner because, let’s face it, owning a company that cuts grass isn’t that impressive.
“It’s just landscaping”
And of course revenue could always be higher.
Transition #3 (solo entrepreneur —> buying into a larger business)
So, I decided to make a jump.
Earlier this year (2025), I bought into my friends property maintenance company.
It was a major jump in both operations and revenue.
Probably 6-7x what I was doing myself.
First and foremost, it’s an awesome partnership. I can see myself being business partners with him for the rest of my life. And I’m excited about work every day.
But, this also solved my status insecurity.
If the industry I work in isn’t going to impress people, maybe the money can.
I wouldn’t have to tell people I “just” own a landscaping company because we also happen to make a bunch of money (not true btw, but it seems true on the surface).
And it worked!
When people now ask me what I do, I tell them I own a landscaping company with a business partner.
No “just” in sight.
And if they’d ask about revenue, they were always impressed when I told them.
Problem solved, right?
Not really. Because there’s a new problem.
It wasn’t my business.
I mean on paper it is, but I didn’t start it.
Sure, I helped grow it significantly but it already existed before I got there, so in my mind, I did the easy part.
I used to hope that people wouldn’t ask what I did for work. Then that they wouldn’t ask about my revenue.
Now I hope people won’t ask how I got here.
It seems like no matter where I land, I feel like I don’t belong there yet.
I don’t know if that’s insecurity, ambition, or just the cost of moving faster than your self-image can keep up.
I’m still figuring it out (as you can see).
There’s an idea I’ve been sitting with lately:
Identity lags reality by 1-2 years
That feels uncomfortably true right now.
Personally, I still feel like I’m in 2023, pushing lawn mowers for someone else, trying to convincing myself I’m allowed to be here.
I don’t know if that means anything needs to change.
And if it does, I have no clue how to change it.
On repeat this week
I’ve been binging Fallout recently and the soundtrack is absolutely phenomenal.
It’s all late 50’s, early 60’s stuff.
This song has been stuck in my head all week.
I can’t stop doing the little grunts from the chorus unprompted.
Until next time, try not to take life too seriously.
Talk soon,
Devin
