Why I Work On Vacation and On Weekends and Feel More Balanced Because Of It

– Posted in: career management, time management

work on vacationIn a few days, I’m leaving for a two-week trip to the Philippines, and I plan to work on vacation. I’ll be with my spouse and oldest kid so it’s a family vacation, but January is one of my busiest months of the year, so it will be a working vacation. (Also, since I’m obsessing on international real estate, it will be a business trip for that additional reason, but geographic diversification, investing in hard assets, and starting a very different business are topics for a whole other blog series!). For this blog, I wanted to cover why I proactively choose to work most vacations and most weekends, and how it helps me attain more work/life balance, not less.

I take more vacation and more “weekends”

Last week, I took an unexpected four-day road trip, and I didn’t think twice about leaving because I knew I could still get things done as I needed to. Several times a month I spend hours at weekday movie screenings, which don’t upend my schedule because I move work into a Saturday or Sunday or outside normal business hours if needed. When I have seven days and 52 weeks to work with, I don’t have to jealously guard any one particular time. I actually do more fun stuff because I fit the work around it.

I keep tasks and issues from piling up so feel less time anxiety

When I still worked in a traditional office and didn’t have complete autonomy over my schedule, I felt anxious before and after vacations and weekends because there was the rush to finish before time away and the avalanche to catch up on after you return. For some people, the push makes them more productive, but for me, I just felt unnecessary anxiety. Now that I don’t have to squeeze in every task into a particular time, I feel more time freedom, even if it means giving up some of the supposed off-limit days.

I follow my natural rhythms which allow me to do more with less effort

Some people are more productive if they work long stretches and then rest for stretches. I do better with a more regulated, almost drip-like strategy. I write better when I do an hour or two every day, rather than one full day of writing. The same is true when I’m doing research, analysis, business development, balancing the books, even exercise. It took some experimentation to find the ideal lengths of time and how to pace longer-term projects (and I still need to experiment and refine as life and market conditions change) but a little bit each day is my sweet spot, so long stretches of time off hurt more than help me.


There’s certainly a place for extended breaks – unplugging from email, keeping a clear schedule and keeping yourself open to spontaneity. In addition, if you’re prone to working 24/7, I would experiment with longer breaks and true, no-work vacations in order to confirm that your work pace is indeed sustainable and optimal for you, and not just a bad habit or obsession. I tried the no-work weekends and no-work vacations, and I still do these from time to time, but after 10 years of working on my own schedule, I have found that working weekends and vacations actually works out better for me. Experiment both ways, and let me know what you find!

Of course, if you’ve taken a well-defined break these past holiday weeks and are sluggishly trying to get back on your regular work schedule, my latest Forbes post has six strategies for how to focus on work when you don’t want to.


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