The Highlights
The hardest part of ownership? Loneliness
You’re the last line of defense, and it wears you down
You can’t vent to your team, spouse, or 9-5 friends
That pressure builds up and silently until you burn out
It doesn’t show up on the P&L, but it chips away at everything
You don’t need therapy, you need connection
Tangible Takeaways at the end for practical ways to fight the isolation and grow through it
Inside the Isolation
I still remember Friday nights at my restaurant…The place was packed. 300+ covers, music thumping, servers moving like a choreographed machine. From the outside, it looked like success. But I wasn’t out front shaking hands or sipping a whiskey to celebrate. I was in the back, flat on the the floor, trying to figure out why the dishpit sink wasn’t draining, just when one of our staff turned the corner and yelled out - “Wi-Fi is down! The point of sale can’t take payments!”
Queue the sinking feeling of loneliness.
Nobody tells you how solitary the journey of ownership is much of the time. It’s not just the physical exhaustion - it’s the mental weight. When things go sideways, there’s no boss to escalate to, no HR safety net…just yourself to rely on.
Your name on the lease, and people depending on the paycheck you sign. You’re the last line of defense and the first to skip a bite so everyone else can eat.
The kicker?:
There aren’t many venues for you to talk about it. You can’t vent to your staff because it rattles morale. Forget dumping it on your spouse because it stresses them out and affects your sanctuary at home. Your 9–5 friends? They probably don’t get it.
So you bottle it up.
Smile through it.
And keep going.
The world sees growth, revenue, headcount - but no one sees the internal cost. That weight doesn’t show up on the Balance Sheet, but it chips away at your clarity, at your resolve, and ultimately at your joy until one day, you wake up feeling like a deflated balloon. Or worse, you start to resent the business you built from nothing.
That’s the unfortunate reality for most founders I work with. They don’t need more strategies or systems. They need someone who gets the pressure. The pride. The weird mix of freedom and fear. That’s why I left the kitchen and started working with founders.
To be the advisor I never had.
Someone who knows what it’s like to be stuck fixing a sink at 9pm on a Friday, while everyone else thinks you’re raking in the cash and “living the dream.”
Ever Feel this way..? Here’s how I beat it:
Tangible Takeaways
You’re not alone in feeling alone. But doing nothing is what leads to burnout. Here’s how to fight back without needing to “go to therapy” or take a sabbatical:
1. Build a peer circle, fast.
Start simple. One text to another founder:
“Hey. Can we do a monthly check-in? Just business owner to business owner.”
This kind of peer accountability is worth more than any mastermind or course
2. Schedule “CEO Time” weekly.
Block 1–2 hours per week. No team, no tasks. Just you, deeply thinking, journaling, planning. This gives your brain space to catch up emotionally, not just tactically.
3. Talk to someone outside your business.
An advisor, mentor, or ex-owner. Someone who understands the stakes without being emotionally entangled in them. Even 30 minutes can release pressure.
4. Stop pretending you’re bulletproof.
Your team doesn’t need the full breakdown, but a little transparency builds trust.
Try: “Hey, it’s been a tough week. Appreciate everyone staying sharp! We’re in this together.”
5. Track your stress, not just your KPIs.
Every week, ask:
Am I energized or drained?
What’s one thing I can hand off?
Who can I talk to this week who “gets it”?
You don’t need a hundred solutions. Just one or two better habits.
If this hit home, and you’re thinking about an exit in the next 3–5 years. DMs are open.
I share real, trench-level stories from the deal table every week.
Follow @exit_expert on X if you want to prep smarter, not just hustle harder.