At some point, your day starts sounding like this:
"Hey, can I spend $15 a month for this tool?"
"Uh, boss... what do I say in this situation?"
"What did we decide on ____?"
Check the minutes.
Another ping. Another approval. Another escalation that shouldn’t have needed one.
You expected to own the big stuff. Strategic hires. Partnerships. Major directional calls.
Instead, your brain is fielding decisions that shouldn’t even be occupying it.
Founders should own the meaningful swings. If you’re fielding the trivial ones too, though, something's broken upstream.
That's not scale.
It’s leakage.
The Expediency Trap
Let’s be fair.
Most founders don’t cling to control because they crave it. They do it because it’s faster.
"It's easier if I just handle it."
And it is.
In the short term.
If your company feels like a house of cards (held together by glue and duct tape), you’re going to plug holes. Every day. All day.
You’re not trying to dominate the system (you really aren't). You’re just trying to keep the ship afloat.
But expediency, repeated often enough, becomes conditioning. This is what we call "learned helplessness," and it's a major killer (read: management burnout producer) in the workplace.
Hard truth? This doesn't appear because your people are incapable. It's because... they've been trained to escalate.
Learned helplessness doesn’t start with one catastrophic leadership mistake. It forms through accumulation.
The override. The rescue. The silent correction.
The “I’ll just fix it" moments that add up day after day.
Heck, even the praise for escalating instead of owning (you know you've done it).
Over time, the pattern becomes clear: When in doubt, route upward. Then? Doubt becomes "when it's time to think, route upward." Great.. Just...great.
Point is? You don’t hire incapable people. You train capable people to wait for your input.
And eventually, the questions get smaller... more granular... less weighty and more mundane:
“Can I spend $15?”
“What should I say?”
“Didn’t we decide this already?”
Now you’re not just leading. You’re repeating. Repeating instead of replicating.
Congratulations, Champ.
Now watch it, because this is where most founders misdiagnose the issue:
They think the problem is overload. It’s not — it’s distribution.
You hired humans because diverse, distributed cognition improves decisions. Different experiences. Different tensions. Different perspectives forcing gaps into the open.
That’s the whole point.
If every meaningful decision still routes through one brain, you’ve collapsed the system into a single cognitive style. You can justify it by saying you're "shaping the culture to align with your vision," but in reality:
Decision quality flattens.
Throughput caps.
Initiative erodes.
Morale quietly sags.
Nothing puts someone in a box faster than knowing the boss will ultimately take responsibility anyway (hey, remind me to talk with you someday about that "box experience" and what it does to folks, okay?)
Ultimately, hard truth: that’s not mentorship. It’s containment.
The best-run organizations feel different. You can sense it almost immediately (sometimes as soon as you walk on the premises or join the virtual meeting).
There’s no panic when a problem surfaces. No frantic escalation. No frozen silence waiting for direction.
There’s a palpable undercurrent of:
"I trust you to solve this."
Not hands-off.
Not abandonment.
And (believe it or not), it's not chaos, either.
There exists trust with bounds: Clear decision rights. Defined financial thresholds.
“You’re good up to this level. Above that, we talk.”
"You handle this type of engagement — you've proven yourself strong in those areas."
That culture doesn’t emerge accidentally. It’s built. And it’s maintained.
I know what you're thinking:
"I don't ever avoid work!"
Exactly. That's... kind of the point.
You see, here’s the uncomfortable truth: Many founders know how to run the machine.
They know how the pieces fit.
They know where the revenue comes from.
They know how to fix almost anything.
They’re good at it. Sometimes even great.
But running the machine is not the same as building the organism.
Culture requires People Work (this is where most of you are going to shut down on me, but hang tight). Here's what's needed:
Understanding what motivates, discourages, and challenges each team member.
Coaching judgment instead of supplying answers.
Reinforcing autonomy without lowering standards.
A solid founder either becomes the Compass (the person who shapes this intentionally) or you hire someone capable of building that trust DNA and replicating it across managers.
Not talking HR here. Not compliance.
A culture-builder.
Because if no one is shaping how autonomy's developed, expediency will shape it for you. And you'll be the one leading the charge right in the direction that led to this place from the start.
Now ask yourself: What would happen if you stepped away for 30 days?
Really.
Would meaningful decisions stall?
Or would trivial ones finally stop routing upward?
If your ship only floats when you run from station to station, you didn’t build a crew.
You built dependency.
And dependency is not leverage. It’s structural fragility.
The upside here is simple: This is fixable.
You don’t have an intelligence problem.
You don’t have a hiring problem.
You don’t have a motivation problem.
You have a conditioning problem.
And conditioning can be reversed.
It starts with boundaries, defining what requires you (and what explicitly does not):
Clear decision rights.
Clear spending thresholds.
Clear ownership lines.
Then comes mentorship. Not answers, but judgment coaching.
When someone asks, “What should I do?”
The answer becomes, “What do you think?”
And then you let them own it.
Yes, mistakes will happen. That’s part of building a crew. I'm convinced that the best organizations aren’t the ones where nothing breaks (where's the challenge in that?) Instead, they’re the ones where autonomy increases over time.. where trust becomes palpable.
This is also where the founder’s presence sharpens the system instead of simply holding it together.
You don’t need to disappear. You simply need to stop being the default route.
That’s how you move from running a machine…
…to leading something bigger than yourself.