How To Have the “Best Years of Your Life” (Again)

Last night I watched a fun + inspiring (if unextraordinary) film called Being Awesome, about two high school students who reconnect after their high school reunion and form a mutual pledge to overcome their decade (or decade plus) of failure.

The movie dwelled a lot on the challenges of high school and the regret many adults feel in the aftermath. For some people (including the character Teddy in this movie, high school seems like “the best years of your life.”

This view bothers me a lot, because 1) it’s really depressing to think that you peaked in high school, 2) it’s untrue to think that life after high school isn’t or couldn’t be better, and 3) high school is for most people a terrible experience and a terrible institution. Still, there must be *some* reason people look back on those 4 years (for most people, the years between 15 and 19) as the best (or some of the best) years of their lives.

An Amazon commenter on the movie left a review which jogged this thought for me:

As someone about to hit their 20 year high school reunion, it perfectly brought back the emotions you still feel about the most transformative years of your life.

“The most transformative years of your life.” That’s pretty spot on, actually. What if the thing that makes us so fond of our (often painful) high school experiences is the fact that we were changing so much?

I have a working theory along those lines.

In high school, you were awkward, you were raw, you were unformed. You were still figuring out how you worked, how society worked, how work worked, how love worked, how friendships worked, etc. Precisely because of that, every experience was dear and novel enough to remember. And precisely because of your ignorance and unformed-ness, you were full of potential*, and the future was a broad road laid out in front of you. You also completed this process alongside other people who were experiencing the same metamorphosis – you had a rare camaraderie which becomes less common with age.

As you got older and left high school and college, you settled into your routines and into your chosen track, becoming more solid and more molded. You mastered most of the things you (and other young people) struggled with in your teen years. That’s perfectly normal and healthy, but it can also go too far in the direction of comfort.

Many people (like the protagonists in Being Awesome) keep their lives so small and unchallenging and comfortable that mastery becomes meaningless. Lloyd works as a teacher in the same high school. Teddy works at a bar. Yes, they may have mastered those parts of adult life, but they have hardly ventured out of the things with which they were comfortable in high school.

You’re probably in better shape than Teddy and Lloyd, but you have probably also ceased to change and evolve at a pace beyond your comfort zone. This, I think, is why you won’t be looking back at the years of your current life as “the best years of your life.” This is why you still might be looking fondly back at high school instead.

It’s the rate of  rapid change and development and self-discovery that makes the teen years the best and most memorable/important years of many peoples’ lives. It’s the feeling of potential. It’s the feeling of camaraderie. It’s perfectly possible to replicate and even top these elements of your “best years” at any time in life.

I’ve written before about the value of new experiences. Some people actually think that they can lengthen your perception of time. They can certainly do a lot to restore the disorientation and novelty and development that happened for you in high school. In fact, while you may be more experienced now, you (now that you’re an adult with a job) probably have better access to new experiences than ever:

  • Go travel to a new country where you’re a bumbling idiot who doesn’t speak the language or know the customs.
  • Go try to acquire a new skill, like jiu-jitsu or boating or dancing, where you’re likely to make embarrassing mistakes.
  • Go move to a new city, build a new friend group, and start a new job. Your experience of rebuilding from scratch will be quite memorable.

You may have to plunge your life into the same baptism of controlled chaos* you had when you entered your teen/high school years. That’s easy enough. Camaraderie I haven’t figured out yet, but perhaps you can do what Teddy and Lloyd did and mutually pledge with some of your old buddies that *these* will be the most awesome years of your life.

Warning: this is as yet untested advice, outside of some of my own reflections and experiences (my life immediately after high school – moving to a new city and starting a new job – I will probably remember best) . But it does seem to explain why certain experiences (including but not limited to high school and college) are so memorable for us. Give it a shot on a micro scale sometime.

* Intellectual credit: Psychologist Jordan Peterson lectures pretty frequently about the relationship of known/unknown, order/chaos, and potential/actual. I would be remiss to not give him some credit here.

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James Walpole is a writer, startup marketer, intellectual explorer, and perpetual apprentice. He opted out of college to join the Praxis startup apprenticeship program and currently manages marketing and communications at bitcoin payment technology company BitPay. He writes daily at