My secret to balancing work + play on vacation 🏝️

A Clurb Member asked: A trick for handling vacation days/holidays?

Ok I’ll admit it: vacations can stress me out. While I’m supposed to be relaxing, I catch myself thinking, ‘Shouldn’t I be working on my program?’ And when I am working, I’m thinking, ‘Shouldn’t I be spending time with my family?’

Vacations sound amazing in theory, but now that I genuinely enjoy tinkering on a computer all day, it’s tricky to balance work, family time, and actual downtime. I just got back from visiting my OG home on Guam, and I (re)learned a very essential lesson.

So before the trip, I made the decision that this is indeed a vacation where I actually want to work. By making this decision up front, I wouldn’t have any guilt around when I did work. I also decided that I wouldn’t give a hoot about people thinking or saying, “you’re on vacation, you shouldn’t be working.”
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But here’s where I messed up. I didn’t immediately communicate what I wanted. So I straddled blurred lines reading business books under the dinner table and felt a deep sense of FOMO bringing my laptop to the beach while Abbey was in the water.

Eventually, I realized all I needed to do was clearly define what I wanted to do—and commit to it. That simple shift let me be fully present during both work and play.
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The thing is, it’s hard to plan when I’m going to work and when I’m going to play when I don’t know what all the festivities are ahead of time. And this is where flexibility and acceptance come in.

Sure, I could block off specific days and times to work —but if a friend invites me to go off-roading for the afternoon, I’ll rearrange things to make it happen. Because, well, vacation 🤸🏾‍♀️
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That said, I leave room for spontaneity—while also giving myself time to recharge alone (because, my ambivert-ness can only handle so much).

As for using my journal on vacation… I don’t really. Vacations are also a time to step away from structure and try new things.

But when I get back, I'm literally craving to get back to my routines and geek out with my journal to process the trip, recap memories, refocus, and slap in my new stickers. It’s like my post-vacation ritual.
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​The truth is, handling vacations—or any unstructured time—comes down to clarity, communication, and having flexibility (which btw I also have a hot yoga story to share in the future).

These are things I’ve spent years practicing and now teach in The Well-Being Program. So if you struggle to balance work and rest, you’re gonna wanna check your inbox tomorrow when applications open again. Spots go fast, and I’d love to help you create that balance too.

But for now, think about this:

What needs to happen to plan your time with ease—even on vacation—while leaving plenty of room for joy and spontaneity?
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✌🏾TTYL!✌🏾

Simie

P.S. If you’re wondering what I was devouring under the dinner table, it was Rework by Jason Fried & David Heinemeier Hansson. It’s a no-BS guide to working smarter, not harder (although I think their other book It Doesn't Have To Be Crazy at Work slapped harder)—the irony of reading this when I was juggling vacation plans and work guilt.
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P.P.S. I'm about to start working on my next video. Anything you NEED to watch right now? Hit reply and lemme know!