The Myth of the Always-On Founder
Or minute of mistaking chaos for leadership
I used to believe that real founders never step away.
That presence was everything. That leadership meant being reachable at all times, answering every Slack ping, jumping on every call, staying up late to fix the unfixable.
I wasn’t alone in this belief. In fact, most early-stage founders I meet are still trapped in it.
It’s a seductive narrative:
You’re the backbone. The hero. The one who holds it all together.
And if you rest — the whole thing collapses.
Back then, I didn’t just accept this story — I lived by it.
So when I first read Zappos: From Zero to Billion many years ago, one moment stopped me cold.
At the height of their financial crisis, when everything was falling apart,founder Tony Hsieh left.
He went into the mountains. Literally.
Not to escape. But to breathe.
At the time, I couldn’t comprehend it.
How could he do that? How could he abandon his people, his company, his responsibility?
To me, that was weakness. A betrayal of leadership. Something I swore I would never do.
I thought a real founder should stand on the front line.
Fight for every dollar. Solve every problem. Be the last one to leave.
And then life handed me the same test.
The Day Everything Froze
It happened the day before payroll. Our company accounts were suddenly frozen by the bank.
No warning. No explanations. Just locked out.
Incoming payments? Blocked.
Salary transfers? Impossible.
Vendors, taxes, everything in limbo.
I panicked. I was pacing. Calling everyone.
I downed enough calming pills to sedate a horse.
My brain was fogged with adrenaline, desperation, and a brutal soundtrack of self-blame.
And the worst part? I wasn’t solving anything.
Because if you’ve ever dealt with banks or lawyers in a real crisis, you know: nothing moves quickly.
No one drops everything to help you. Especially not on your schedule. I couldn’t speed anything up.
But I could, and did, wear myself down trying.
Then something strange happened.
In the middle of the panic, I remembered Tony.
And for the first time… I understood.
The Mountain Shift
The next morning, I got in the car and drove out of the city.
Not to escape. But to stop spiraling. To clear the fog in my head. To remember how to think.
No laptop. No calls. Just a notepad, silence, and the mountain air.
And when I came back two days later, something had shifted.
I wasn’t calmer because the crisis was over.
I was calmer because I finally saw it for what it was:
A logistical problem. Not an existential one.
And in that clarity, everything became solvable.
We opened new accounts. Hired the right lawyers. Told the team the truth, openly, calmly.
They didn’t panic. They rallied.
We told clients what happened.
They understood. Some even helped.
We found interim solutions, patched gaps, redesigned our payment workflows.
And by the end of that month, we were not just stable, we were stronger.
More resilient. More diversified.
No longer dependent on one financial partner.
No longer winging it behind the scenes.
All of that was possible because I had stepped away, just long enough to regain clarity.
Urgency is a System Design Problem
That experience taught me something I had missed for years:
Most crises in business do not require immediate founder intervention.
But most founders never realize this — because they build systems that rely entirely on their presence.
And so, every notification becomes a trap.
Every absence becomes dangerous.
Every weekend becomes a risk.
I used to think being “always on” was a virtue.
Now I know it’s a warning sign.
If your business collapses the moment you step away, that’s not a leadership badge.
It’s a structural flaw.
A business built on synchronous urgency, unclear roles, and founder heroics will eventually burn out its creator.
It’s not noble. It’s unsustainable.
Maturity Looks Like Asynchronous Calm
Today, I judge the health of a business not by its speed, but by its stillness.
Can the founder unplug for 48 hours and return to a system that still works?
Can decisions be made without them?
Are there documented escalation paths, not just verbal dependencies?
Does every role have clarity around scope, ownership, and authority?
These aren’t “nice-to-haves.” They’re survival infrastructure.
True maturity in a business shows up when the founder disappears and the machine keeps humming.
Because if you can’t unplug, you’re not in control. You’re just busy. And “busy” is not a strategy, it’s an addiction.
The lesson I almost missed
The greatest gift you can give your business is not your constant availability.
It’s your clarity. Your calm. Your ability to make decisions from a centered place, not a reactive one.
You can’t do that if you’re drowning in notifications. Or chasing shadows in Slack. Or panicking at every minor disruption.
It took a full-blown financial lockdown for me to learn that.
I hope you don’t have to wait for the same.
Because real leadership isn’t presence.
It’s architecture.
Disclaimer.
Every business has its nuances, and every founder has their unique context and resources. Whether or not my advice applies depends on your situation, experience, and needs. But one thing is universal—use your brain.
Think about how to apply the advice in your context before acting.
Your way.
How to Use the Eisenhower Matrix to Regain Control
When your entire week feels like an emergency, it’s not a productivity issue, it’s a decision filter problem.
The Eisenhower Matrix is a simple but powerful tool to reset how you process work and avoid getting trapped in reactive chaos.
Here's how to apply it as a founder:
Step 1 — Capture Everything
Dump all current tasks, ideas, open loops, and requests into one list.
Include team asks, emails, meetings, ops, client issues. Everything.
Step 2 — Categorize Using the Matrix
Use this 2x2 structure:
Step 3 — Protect the “Not Urgent but Important” Zone
This is the zone where your best thinking happens:
- System design
- Strategic pivots
- Product evolution
- Team development
- Deep financial review
Most founders spend zero time here, and then wonder why the business feels stuck.
Block time weekly for this quadrant. No excuses.
Step 4 — Build Delegation Pathways
For the “Delegate” category:
- Create SOPs
- Assign clear EORs (Expected Outcomes per Role)
- Build dashboards to track progress asynchronously
- Use Loom videos to hand off recurring tasks once
Your goal is to never see the same low-value task twice.
Step 5 — Review Weekly
This isn’t a one-time exercise.
Every week, spend 15 minutes sorting your work through this lens.
You’ll be shocked how many “emergencies” evaporate when filtered properly.
Get my Free Weekly Review Ritual Template
Bonus:
If everything feels urgent, it’s not your team. It’s your filters.
Fix them, and you fix your time.
And if your business truly can’t function without your constant input?
You don’t need better time management. You need a system redesign.
That’s exactly what I help founders build inside the Ops-On-Demand™ Sprint.
Not just relief — structure. When you’re ready, I’m here.
And one more thing.
Every founder has their own way of getting through hard days.
Her journal reminds me (and maybe you) that it’s okay to struggle — and still move forward.
- Eugene
Join the “most offbeat” Businessletter on entrepreneurship.
Hi, I’m Eugene.
Over the past 20+ years, I’ve grown an international agency from one-person freelance to a multimillion-dollar business. I’ve led teams, scaled systems, burned out, rebuilt, and learned (the hard way) what it really takes to run a business that doesn’t consume your life.
I help them make sense of complexity, design simple systems, and create the kind of business they actually want to run.
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