How a “Too Short” Vacation Changed My Mind About Rest

With Labor Day looming, the end of summer can start to feel like a deadline. If you didn’t take the vacation you planned or give yourself enough of a break, you may feel like you didn’t make the most of it. And that disappointment can quickly turn into guilt about why you didn’t do more for yourself.

That pressure caught up with me this year. My schedule is rarely light, but the past several months have been especially busy. I usually take August off but with my mother’s caregiver away, I went to California to help my siblings look after her. I’m always grateful for time spent with my family, but the change in plans meant a shortened stay on Martha’s Vineyard, one of my favorite annual traditions. 

A similar situation came up months earlier. Every spring, I go to Turks and Caicos to take a break from the relentless pace of everyday life and get some much-needed sun after a winter of dreary days and too many hours indoors. I usually stay for a week, but this year my packed schedule allowed only three days. I had to choose between going anyway and deciding the trip wasn’t long enough to be worthwhile. 

I said yes to the three days. I relaxed, disconnected, and came home feeling restored. Even so, I kept comparing the trip with the full week I’d wanted. Measuring the experience against that ideal kept me from appreciating that those few days had given me exactly what I needed. 

Letting a shorter vacation count

Letting the trip count meant focusing on what I gained rather than what was missing. A shorter trip may even offer an unexpected advantage. When you have an entire week off, you might open your laptop intending to check one email, only to find that one task has become several. With only a few days away, you may be more inclined to leave work alone.

Three days aren’t automatically better than seven. This was the version I could make possible this year, and it allowed me to recharge. Wanting more didn’t erase what I’d gained. I would never tell one of my students or an entrepreneur I work with that two days away don’t count because a full week isn’t possible for them. I tell them to appreciate the time they have and take it when they need it. I needed to give myself that same permission.

Looking beyond the ideal outcome

In negotiations, an ideal outcome can give you direction, but it isn’t the only result worth considering. Knowing what matters most can make room for more than one definition of success. Applying the same thinking to rest helped me see other possibilities.

When work takes me to New York for the day, I can choose to stay overnight rather than rush straight to the airport afterward. That gives me the chance to have dinner with friends, walk through Central Park, or do a little shopping in my favorite city. Going to Martha’s Vineyard each year doesn’t have to mean one extended stay, either. I can make several shorter visits throughout the summer or enjoy the island during the off-season, when it’s not as busy. 

Neither option is the extended vacation I would prefer, but each offers something I value. Being open to several getaways throughout the year means I don’t have to place all my expectations on a single week that may not fit neatly into my schedule. 

Waiting for the perfect opening assumes it will eventually arrive. I don’t know what life will look like next year or what new responsibilities may come up. If a few days away can give me something I need now, dismissing that option in favor of an uncertain future doesn’t make sense.

Honoring the promise to myself

Being flexible about what counts means reconsidering whether the rule I’ve set is necessary and taking the available option seriously. I can decide what I need and find another way to provide it rather than denying myself anything that isn’t the ideal.

I also have to hold myself accountable. If I tell myself that an extra night in New York or several smaller trips will take the place of a longer vacation, I have to follow through. I can’t promise myself those opportunities and then let work or another obligation take them away. Protecting the plans I make is part of saying yes to myself.

That’s what I tried to do this summer. I may have spent less time on Martha’s Vineyard, but once I got to California, I rewarded myself with day trips to Napa Valley and have committed to spending Labor Day weekend out of the country.

The larger myth about what makes something meaningful extends beyond vacation. You may find yourself believing that an experience or accomplishment has to look a certain way before it can count. When life changes that picture, you can focus so much on what’s missing that you stop seeing the value in what you do have.

Reimagining what counts doesn’t mean pretending that less is always enough or that every outcome is equal. It means refusing to let an unavailable ideal turn every other possibility into a failure. I can still want the ideal outcome while accepting and making the most of what’s possible.