What Does it Mean to “Live Your Life in Seasons”?

One of my favorite physiology concepts is the “end of history” illusion.

Say you’re 35 years old. When you plan your life 15 years from now, you likely assume you will not be too different than you today. However, you likely strongly believe that you are much different today than you were 15 years ago.

This belief that your future self will be exactly the same as you are today is the “end of history” illusion.

It’s impossible to know what we will care about in the decades to come. So how come we often plan our lives and careers like we do?

That’s why a repeating theme of Sabbatical is “living your life in seasons.” To live your life in seasons is to recognize that you are a different person at different stages in your life and each of those stages serves a different end. Sometimes it is a restful season. Other times, it is a season to work and amass wealth and knowledge. Sometimes you are focusing on family and community. Other times, yourself.

It’s the answer to the “can you have it all?” question. 

You can. Just not all at once.

Most interviewees on this site will cite some version of this as the reason they decided to drop everything to figure out what’s next. Sure, they could work 40 or 50 years straight. But what if there were more options?

Why Living in Seasons is Possible

Living in seasons has long been possible — just ask any seasonal worker. But there is a unique confluence of trends that are making it more achievable:

  • There is little reward for staying at a single company. There are no pensions to speak of and most of us have 401ks that we can port from place to place. There is often a salary bump for those switching jobs, and one of the fastest ways to grow your network is to do stints at several high-growth companies.

  • The digital transformation of most industries has created unprecedented opportunities for ambitious and talented people to earn high salaries. It’s created a power curve where the top tier of talent can be rewarded equity, land signing bonuses, and be actively recruited by several companies at once. Saving a few months salary is possible when you are one of these people.

  • However, achieving these high salaries often requires an extreme commitment that requires much of your time and energy, and in some cases requires you to sacrifice your health or personal relationships as you focus on your career.

  • We can work from anywhere. Thanks to COVID and the rise of remote work, knowledge worker jobs have been decoupled from the office. Organizations have adapted to have at least some of their team members be distributed. 

In other words, there is money, status, and benefits to working extremely hard. There is also ample opportunity to optimize around flexibility. You can earn more money than ever and you can experience more of the world than ever before. However, you can’t do it all at the same time. That’s living your life in seasons.

chart with an oscillating line

The key is knowing what season you are in and why you are in it. Be purposeful and unapologetic about what season of your life you are in. This means getting FOMO and letting people “pass you” while you are resting. Sabbaticals can be difficult when you see your peers getting promotions or accolades that, deep inside, you think you could have had.

It also means missing out on some things you would find short term fulfilling in service of some larger goal. Most entrepreneurs of massive businesses point to birthdays missed, health sacrificed, and hobbies left unexplored.

If you’ve lived your life in seasons, I’d love to feature you on Sabbatical. We’ll be covering more on how to do this, backed by interviews with those who have, in upcoming essays. Subscribe to Sabbatical to follow along.

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