I have been known to be a chronic bite-off-more-than-I-can-chewer. What can I say? I like doing things, I like helping people, and, because of that, I have difficulty saying no. (It’s a work in progress.)
But much to my dismay, weeks only have seven days and days only have 24 hours no matter how much needs to get done! This has often led me to bring work (job, side gig, and writing) with me on my weekends away or even my vacations and longer breaks.
After many years of overworking myself in this manner, I don’t condone that kind of behavior in myself anymore. I developed this series of questions to ask myself as I’m packing to stop if I might be getting in my own way of actually enjoying the break I intended to take all along.
- Do you have time blocked in your trip to work?
- Do you have a space available to work in? (And a follow-up: Does it have Wi-Fi if you’ll need it?)
- Do you have bag space to bring what you need?
- Do you work well (at all, or on this particular type of work) in a space that’s not your normal desk?
- And, last but certainly not least, does the work actually need to get done over this time period, or can it wait?
If I’ve planned an exciting sightseeing weekend where the itinerary is set from sunup to sundown, I’m not actually going to have an hour to sit and write! I’m going to be tired and want to relax and decompress in the evening. And let’s be honest, there is not a quiet space to concentrate when you’re at the Airbnb for the family reunion.
Let’s talk about the elephant in the listicle: number 5. When I get overwhelmed by my to-do list, my gut reaction is to try and get as many things done as possible. Because then I’ll finally feel better when it’s all cleared, right? But the to-do list is never really all cleared. At work, that’s called job security. At home, that’s just called being an adult. I’ve learned my breaks—day trips, weekends away, vacations—are an important part of maintaining my energy and joie de vivre so I can continue knocking things off my to-do list like a badass.
So, here I am visiting St. Louis-area National Park sites in order to get cancellation stamps in my NPS passport book, a treasured collection of mine.

I brought my computer because I made sure that there was time in our Saturday itinerary to get a couple of things done that I just hadn’t gotten to on Friday, but that needed to be done before Sunday. Then I put my computer away and enjoyed time with my husband and our friends. I never used to be able to do that! I hope these questions will help you get to do the same.
How do you decide when to work on a weekend or time away, and when to leave the laptop behind?


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