About two years ago, I was on a call with a founder from Kansas. Small accounting agency, 8-10 people. We'd connected on LinkedIn somehow and started talking shop.
The conversation was good. We were trading war stories, comparing notes on what works and what doesn't. Then he asked: "So... why aren't you in the Maldives?"
I laughed. "What?"
"I mean, you exited your agency, right? Built systems, delegated everything. Isn't that the whole point? To finally relax?"
He was genuinely confused.
And honestly? I get it.
Because that's what everyone sells. That's the dream, right?
Build systems. Delegate. Automate. And then... freedom. Beaches. Passive income. The 4-hour workweek. That's what I heard at a management conference back in 2015. That's what the gurus promised. That's what I believed for way too long.
But here's what actually happened when I left operations:
I'm still working 60+ hours a week. Just different. Learning, growing, developing new skills, and routing the paths I have never been. Probably one can call this joy, not work.
When I was running the agency, my days looked like this:
Morning coordination with department heads. Every question about hiring, sales, marketing, delivery — all of it landed on my desk.
Mediating conflicts between team members. Talking down unhappy clients when someone on the team screwed up. Writing processes, building automations, distributing responsibilities.
That's operations. Repetitive functions that keep the company running.
And yeah, we eventually built a leadership team that handled all of that. People I'd watched grow from juniors into real leaders — our CTO, our PM, our sales lead, HR. It didn't happen overnight. We built those systems together, especially after that conference in 2015 when I finally got serious about structure.
So yes, I exited operations. And no, I'm not on a beach.
I told that founder from Kansas: "I just don't want to be in the Maldives."
What I do now is completely different from what I did then. But it's not less work — it's different work.
I'm writing. Building a new business from scratch. Having deep conversations with founders — not as clients like in the agency days, but as partners, as fellow operators. Hearing things people normally hide. Learning patterns I never saw when I was buried in delivery.
And yeah, I travel. On my own schedule, at my own pace. But that's not the goal. That's just... life. The work I do now is focused on creating something new. It's strategic, not operational. It requires thinking, not just executing.
And honestly? It's more interesting for me than anything I did while running the agency. Because it's something new.
Here's what nobody tells you:
Operations gives you something psychologically valuable. People come to you for answers. You're needed. Important. The wise leader who knows everything. You feel the weight of the wheel in your hands. You're driving this thing.
And that feeling? That hit of importance?
It's addictive.
I remember when we had to turn down interesting projects because I couldn't clone myself. When we started missing deadlines because I was the bottleneck. When clients got frustrated because everything had to wait for my approval.
I knew I needed to step back. I knew it. But part of me loved being that important. There was one project — an email campaign that needed to work perfectly across every browser and email client. This was 2012, before modern email tools. It was a nightmare. And I sat there, late at night, solving it myself. Because I could. Because I was the one who knew how.
I felt important. Needed. Irreplaceable.
Never mind that my team could've figured it out if I'd just let them. Never mind that I was teaching them to depend on me instead of learning to solve things themselves.
That addiction to being needed nearly destroyed everything. The 2008 crisis hit us hard in 2012. Projects dried up. My business partner couldn't deliver sales. And I... I lived at the office, trying to save everyone's jobs. I didn't save most of them. Just one — he became our CTO later.
But I kept playing hero anyway. Kept staying late. Kept being the person everyone needed.
My health suffered. My marriage suffered. My ability to actually think strategically — completely gone. Because you can't see opportunities when you're drowning in urgency.
So why leave operations at all?
If you get a dopamine hit from being important, if you love the feeling of solving problems, if coming home exhausted but proud feels good — why change?
Here's what I tell founders I work with now:
I don't push them to leave operations if they're not ready. Because if you love the cage, you won't even see the bars. But I do ask them to look at the cost.
No financial cushion. Don't know your break-even. Involved in every client discussion. No one who could step in if you got sick or had a family emergency.
And I'm not talking about vacation. I'm talking about life happening.
Your business — and everyone who depends on it — sitting on a foundation that collapses the moment you can't show up. That's what being stuck in operations actually means.
For me, it led to debt. Heart issues. Frozen bank accounts. Divorce.
But I don't insist. Because logic doesn't beat dopamine.
You either hit a wall hard enough to wake up — or you don't.
Make two lists.
List 1: Moments in your work that give you real satisfaction. Times you felt energized, important, needed.
List 2: Things that drain you. Tasks you hate. Repetitive problems that make you want to scream.
Now compare them.
I bet you'll find something interesting: the things that energize you and the things that exhaust you are often the exact same activities.
Leading the team meeting where everyone looks to you for answers? Energizing.
Leading the same meeting for the 47th time, answering the same questions? Exhausting.
Those are your dopamine hooks. The places where you're getting a psychological reward for staying stuck.
And recognizing them is the first step to actually getting free.
So here's my question:
Have you caught yourself getting a hit of importance from being the person who knows everything, manages everything, fixes everything?
Hit reply and tell me. No judgment — I've been exactly there.
P.S. That founder from Kansas? We're still in touch. Last I heard, he's working on building his leadership team. Not because he wants to go to the Maldives. But because he's tired of being the emergency contact for every small fire. Progress looks different for everyone.



