6 days ago
2
0
Posted On: October 13th 2026, 02:52 pm
Nothing says "I built this business for freedom" quite like needing three days of preparation to take five days off.
Because apparently, going on vacation now requires its own project plan.
You're trying to finish work that isn't even due yet, sending extra client updates, and checking on projects that should be perfectly fine without you for a week.
You've probably also given everyone a very detailed rundown of what to do while you're gone.
Which is lovely.
Except you know that by Wednesday, someone will have a question about a situation nobody thought to include in the rundown.
And you'll be on a beach somewhere, trying to remember exactly what was agreed with that client three weeks ago.
Very relaxing. 🌴
I think this is where a lot of founders start telling themselves they need to get better at switching off.
And to be fair, sometimes we do need better boundaries.
But there's another side to it.
If your business genuinely needs you to make ordinary decisions, clarify what happens next, or find information the team can't access, switching off becomes a lot more complicated than putting your phone on Do Not Disturb.
Because your out-of-office reply doesn't magically give everyone the information or authority they need to keep working.
Unfortunately. That would be a fantastic feature.
And I don't think being able to take a vacation means nothing should ever require your attention.
Emergencies happen. Important decisions come up.
But the team should be able to handle the normal, expected parts of running the business without needing you to prepare for every possible scenario.
Otherwise, you've built a business where taking time off is only possible if you do all the work in advance.
Which doesn't sound much like time off to me.
The interesting question isn't how much you can finish before leaving. It's what can keep moving while you're gone.
And if the answer is "not very much," that's probably worth looking into.
Preferably before your next holiday. ♡
Because apparently, going on vacation now requires its own project plan.
You're trying to finish work that isn't even due yet, sending extra client updates, and checking on projects that should be perfectly fine without you for a week.
You've probably also given everyone a very detailed rundown of what to do while you're gone.
Which is lovely.
Except you know that by Wednesday, someone will have a question about a situation nobody thought to include in the rundown.
And you'll be on a beach somewhere, trying to remember exactly what was agreed with that client three weeks ago.
Very relaxing. 🌴
I think this is where a lot of founders start telling themselves they need to get better at switching off.
And to be fair, sometimes we do need better boundaries.
But there's another side to it.
If your business genuinely needs you to make ordinary decisions, clarify what happens next, or find information the team can't access, switching off becomes a lot more complicated than putting your phone on Do Not Disturb.
Because your out-of-office reply doesn't magically give everyone the information or authority they need to keep working.
Unfortunately. That would be a fantastic feature.
And I don't think being able to take a vacation means nothing should ever require your attention.
Emergencies happen. Important decisions come up.
But the team should be able to handle the normal, expected parts of running the business without needing you to prepare for every possible scenario.
Otherwise, you've built a business where taking time off is only possible if you do all the work in advance.
Which doesn't sound much like time off to me.
The interesting question isn't how much you can finish before leaving. It's what can keep moving while you're gone.
And if the answer is "not very much," that's probably worth looking into.
Preferably before your next holiday. ♡
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