Can entrepreneurs take vacations?
Tweet · Aug 19, 2025
Can entrepreneurs take vacations?
I went in a vacation last week and… I didn’t vacation very well…
I’m just going to come right out and say it— I didnt “shut work down” as well as I needed to.
I was on my phone far more than I wanted to. I took one call that I shouldn’t have taken. I went down rabbit holes that I didn’t need to go down. Overall, I’d give myself a C- for my ability to disconnect and be so the my family.
This sucks to say out loud because I really don’t like failing at anything. And while I don’t think this was a “failure”, I DEFINITELY have room to grow.
By the third and fourth day, I think I was in a good little groove of setting my phone down and not worrying about it, but at that point, the trip was almost over.
This next part is more for me, just as a personal checklist of what I could have done better, but I’m sharing it with the hope that it will help YOU better as well.
even though I delegated and prepped a good amount of time in advance, I didn’t do a great job at setting boundaries with my team. Everything runs through me right now as we’re building, and I didn’t put someone else in my place to assist while I was gone.
I also didn’t let my team know clearly enough that I was out of town, handle it on your own unless I really need to be involved. I THOUGHT I did, but looking back, not really… partially because I’m afraid to step out right now, but also because I thought it’d be manageable.
There will always be things that will be pulling you away from what’s most important… over the last week, I LET those things pull me away. I shouldn’t have.
I’ve created momentum with our business but it’s still in the sweaty startup/ messy middle and I’m scared of what will happen when/ if I don’t keep my foot on the gas.
That last point goes both for my business as well as my brand. Even if I was settled with the business stuff for the day, I was constantly thinking about what I should be doing next with newsletters, posts, apps I’m working on, ideas I have, or any other deep dives that come to mind…
I’m passionately curious and incredibly ambitious, but there’s a time and place. That wasn’t the time or the place.
Here’s what I would do differently and maybe this will inspire you to make adjustments with your travels as well.
clearly let my team know that I’ll be out of town and put someone in place to be my “gate keeper”… if that’s possible
Time block. Get up earlier or stay up a little later to get things done that are urgent and pending. Then shut it down outside of those windows.
It’s okay to be curious, have ideas and be super ambitious… BUT you have to turn it off sometimes. Again with the time blocking. Write down the things that pop into your head and then come back to them later… probably after your vacation.
Take my phone out of my pocket and put it somewhere else. Out of sight, out of mind.
Like I said, I really don’t like that I came up short with this, but in the process I learned a lot.
Odds are I’m still going to come up short again, but maybe I’ll be a little bit better. Or maybe it’ll be a different season and things will be more smooth sailing. Lots of variables.
The point here is that it really is possible to disconnect and enjoy a vacation. But as an entrepreneur, you have to be really intentional about it. It won’t just happen.
Let me know if any of that resonates.