Said Out Loud ·
Your company can't survive your holiday.
What people usually say instead: “I'm only checking in once a day.”
The short answer
CEOs and founders can take real holidays, but only when the company can make decisions without them. If you're checking in every day, the holiday hasn't started. Before you go, hand named decisions to named people, agree what they can decide alone, and try a few days away first.
Drafted with AI for Coach42 · coach review pending · 3 min read
The scene
It's the second morning of your holiday. You're on a hotel balcony at 7am with your phone, because you said you'd check in once a day. Meera has sent three questions she could answer herself, and she's waited since yesterday to send them.
Why can't you switch off on holiday?
Because the company was built to run through you. That's not a flaw in you. We think it's how young companies tend to start: you made every call because there was nobody else to make it.
Then nobody changed it. The team grew. The calls still go to you. So when you leave, the calls don't stop. They queue.
"I'm only checking in once a day" sounds like discipline. It's really a promise to the team that nothing big will be decided without you. So nothing is.
What does a daily check-in teach the team?
It teaches them to wait. Every check-in teaches the team to save decisions for you.
Meera knows the answer to two of her three questions. She sends them anyway, because the last time she made a call while you were away, you changed it when you got back. She hasn't forgotten. So she holds things until the window opens: once a day, on your balcony, before breakfast.
Your team isn't weak. They're doing the sensible thing in a company where your answer always wins in the end.
And you come home tired. You spent two weeks half there and half here, reading messages on a sunbed and answering them in your head at dinner. Your family got some of you. The company got some of you. Nobody got all of you, and that includes you.
Can the company really run without you for two weeks?
Not yet, and that's fine to admit. It can get there, but not by you trying harder to rest. It gets there when decisions have owners who aren't you.
Start with the ones that come up every week: the discount a customer wants, the hire that needs a yes, the supplier who's late again. Give each one a name. Write down the limits, like "under this amount, decide and tell me after". Then comes the hard part. When you're back, don't overrule them unless something is truly wrong.
Our post on how to make your business run without you goes deeper on handing work over. The Two Weeks Away self-test helps you see which parts of the company lean on you hardest, so you know where to start.
Why does it matter if you rest?
Because a founder who can't step away carries the whole weight alone. We call that founder load, and it builds slowly. You stop noticing it, the way you stop hearing a fridge hum.
Being always on feels like care. In part, it is. But a company that needs you every morning is fragile, and the team can feel it, even if nobody says so. The kindest thing you can do for them is become someone they don't have to wait for.
Try a long weekend first. Hand over three decisions. Leave the laptop at home. Then see what Meera does with a Friday where nobody is going to check.
The picture
The cost
One check-in a day means every decision waits up to a day for you. Over two weeks, that's fourteen mornings of Meera holding back calls she was hired to make.
Try on Monday
Pick one decision you make every week and give it to someone by name. Write down what they can decide without asking you, and tell the team it belongs to them now.
The mirror
The mirror
Answer it for an ordinary week. Your answer stays in this browser.
- Take Two Weeks Away: what breaks if you disappear for a fortnight.
- More for Founders
- The 42 Test, for the full picture of how you lead
Questions people ask
- Is it wrong to check in at all on holiday?
- No. Agree one way for real emergencies to reach you, like a phone call, and say what counts as one. That's different from reading every message each morning, which keeps you at work from somewhere nicer.
- How long should my first proper break be?
- Start with a long weekend with no laptop. See what waited for you and what didn't. Then hand over what waited, and try a full week next time.
- What if something goes wrong while I'm away?
- Something small probably will. Let the person who owns it fix it, then talk about it when you're back. If you overrule them, the team learns to wait for you next time.
Signed
Drafted with AI for Coach42 · coach review pending.
Scenes are composites; names are made up.
If any of this is hard to carry, talk to someone you trust or a professional.
Sources
No figures in this column: everything here is opinion or a made-up scene.