Why You Should Take At Least One Vacation Per Season

Simien Mountains National Park, Ethiopia. Photo Credit: Me

Tired of looking at your friends’ summer vacation pics yet? Annoying, right? And how will you feel when those same people post pics from their week-long “Foliage Roadtrip” in Vermont in a few months? And then again this winter when they post even more from their annual ski trip to Vail.

Must be nice to be a trust-funder, right? Um…maybe.

Or maybe they are able to travel so much expressly because they travel. Maybe their investment in themselves in the form of time-off makes them that much more effective during their time-on.

I have taken an average one vacation per season for the last 14 years, including a 15 month motorcycle tour of South America, a two month surf trip to Brazil, and a two month residence in Spain. And before you roll your eyes and say “he must be a trust-funder or tech millionaire” or that I simply must have extremely low ambitions, allow me to tell you a little about myself:

  • I have paid my own way since I was 14. I bought my first car, put myself through college, and have taken no monetary gifts from my parents as an adult aside from a $1,000 graduation gift.
  • I live off the cash-flows of businesses I started and my executive coaching — not from any windfall from a tech exit.
  • I’ve attended two Ivy League schools.
  • I have coached dozens of tech CEOs, corporate executives, and international heads of state.
  • I have humble, but comfortable apartments in the two most expensive cities in the world.
  • And on average I take a 5–21 day vacation once per season.

I say all that not to brag, but simply to let you know I’m neither a silver-spoon type nor a slouch. I simply hustle and have built a life I love living.

And you can too.

But wait? Isn’t the American work ethic supposed to be work 50 weeks, vacation for 2, and check your email morning, noon, nights, and weekends?

F*** that.

That mind-set is a societal sickness promulgated by 1) your small-minded boss, and 2) a certain “crushing it” or “’killing it” segment of tech opinion leaders who believe that working long hours of extremely high productivity is the only way to get ahead.

Yes, hard work is required for success. But so is hard play.

This is no mystery to Reed Hastings, CEO of Netflix, who was one of the first CEOs of a major firm to institute an “unlimited vacation” policy.

According to Hastings, he encourages his employees to take 6 weeks of vacation (just like he does) for business reasons. “You often do your best thinking when you’re off hiking in some mountain or something. You get a different perspective on things,” says Hastings.

But don’t just believe one CEO. According to researchers at Project Time-Off, (an NGO apparently funded by the travel industry, so take it with a grain of salt), in spite of the fact that people who take time off are more likely to be promoted, a majority of Americans don’t take the vacation time that’s allotted to them, let alone ask for more.

The sad result of not taking time off is less engagement, less joy, less creativity, and less overall productivity.

Breaking the routine and monotony of the day-to-day gives you space to think differently. It also increases the perceived length and pace of your life (be sure to follow me for a coming Medium article on this topic).

Think about the people you most admire — the artists, musicians, and business leaders. Do they live monochrome lives reporting to the same office day in and day out? Are they slaves to the corporate work-a-day schedule?

Or do they travel, get inspired by different people and cultures, and embrace that it is only through breaking our routines that we begin to look at problems and our situations with fresh eyes or a different perspective?

That was rhetorical.

The reason I suggested taking time off once a season is that different seasons inspire us in different ways.

  • Summer is about letting go, partying, and relaxing.
  • Autumn is about reflection and investment in oneself.
  • Winter is about giving, gratitude and renewal.
  • Spring is about rebirth and growth.

Each season has its own feeling and message. If you only ever take vacations in the summer, you’re missing 75% of the year’s opportunities to be inspired and opened.


Still not ready to commit to taking more time off? Do you perhaps fit one of these non-vacation-taking-type profiles below?

  1. The “I’m Banking on a Big Payout” Martyr. Maybe you’re an early employee at a tech company, a consultant, a banker or a lawyer. Either way, you’re on a career track that requires a MASSIVE investment of time in the beginning with the hopes of a big payout somewhere down the line. Maybe you’ll have a fat exit. Maybe you’ll become an MD or Partner. Maybe. But remember that presentation you botched? That meeting you nearly fell asleep in? That friend’s wedding you skipped because you had a deadline? You really think you’re showing up for work with your best work on zero sleep?
  2. The “No One Does It Right But Me” Control Freak Boss. I know you because I was you. At 23 I was running a company and had people in their 30’s and 40’s working for me. And I was a total control freak — personally editing my staff’s writing, scripting their phone calls, and generally being all up in their business. I also didn’t take more than 5–10 days off per year — until I burned out at 26. When I finally left and they found an appropriate new CEO, the company continued to flourish. I was flabbergasted. I had thought I was irreplaceable. But as one board member said when I expressed concern over leaving, “When you take your hand out of a bucket of water, is there a hole there?” The lesson is this: when we create space for our employees to take on more responsibility and do more problem solving, they most often step up and do better than we could have done ourselves.
  3. The “If You’re Not Sleeping Under Your Desk, You’re Not Committed” Founder. I first saw this phenomenon working on political campaigns in the early 2000’s (ok, I actually lived it a few times myself), and I’ve seen it over and over in the most recent tech boom. I actually find it somewhat funny. The idea that working 20-hour, adderall-fueled days for weeks or months on end makes you more committed, more productive, or more likely of achieving success is completely bizarre to me. In fact, I’ve noticed ZERO correlation between this work ethic and success. The problem is successful entrepreneurs often tell tall tales of months of zero sleep and set the expectation for aspiring founders that they have to do the same. Look at Marc Benioff, the ultra-successful founder of SalesForce.com. In the early days of SalesForce, he was known for taking 2–3 weeks off at a time just to “think” in Hawaii. No sleeping under the desk for Marc.
  4. The “I’m Honestly Happiest When I’m Working” People Pleasing Workaholic Martyr Who Has No Social Life Outside Work. I’m extremely happy that you have “found your passion” in fashion, tech, publishing, consulting, or whatever. But I also know you’re BS-ing yourself when you say you are ultimately more happy working 80-hour weeks than having an active social life and a regular vacation schedule. The problem is most-likely that you’ve become so addicted to the feedback you get at work that you’ve not really sure who you are when you’re not working. My friend Andy Ellwood wrote an eye-opening piece on this phenomenon just this week. Check it out.
  5. The “I Only Get Two Weeks Vacation So Stop Asking” Worker Bee. Just because you work for a company that is stuck in the stone age, doesn’t mean you don’t have other options. Unlimited vacation policies are the new “free coffee” at some of the most successful companies. Not sure where you’d ever find companies that offer unlimited vacation? Here…let me Google that for you.

At the end of the day, taking more time off is a choice. It is a choice of people who are ultra-productive, ultra-creative, and ultra-connected. Whether or not you join their ranks is up to you.

Here’s what I want you to do to get started:

  1. Take all the vacation that’s allotted to you. It’s yours. Take it. Would you turn away a paycheck that was due to you? That’s effectively what you’re doing in not taking your vacation days.
  2. Ask for more vacation in your next performance review. In many companies, pay and vacation are both negotiable levers. If you make $100,000 a year, an extra week of vacation is worth about $2,000 to your employer. What’s it worth to you? If you’re up for a $10k raise, how about swapping back $2k for that extra week. I guarantee you won’t miss the money, but you’ll be EXTREMELY grateful for the time off.
  3. If #1 and #2 don’t seem doable, start looking for a new lob. Yes, it’s that f-ing important. This is your LIFE. And wasting it toiling away in the hopes of some recognition or payout in the future is a damn shame. Don’t believe me? Believe British philosopher Alan Watts. Again, there are tons of companies that offer unlimited vacation. Still not sure where to find them? Let me Google that for you.
  4. And if #1, 2, and 3 don’t work, maybe you need to work for yourself. It’s not easy, but it’s hands down the best way to go. More advice for doing that in another post coming soon…

And I do hope you figure it out. I’d love to run into you on the slopes this winter!


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Edward Sullivan is the founder and head coach at LeadWell.co — a boutique coaching and training organization that helps start-up CEOs and corporate executives navigate the challenges of leadership with authenticity. With offices in San Francisco and New York, LeadWell helps leaders and their teams optimize their performance and overcome obstacles to growth. He can be reached at edward@leadwell.co.