Three Lessons From My 20s

Penned October 2020

This essay is a little overdue time-wise. I also want to be clear that I didn’t write this for you, my dear audience of 20. I wrote this for myself, to clear some cobwebs in my own mind. 

Let me get all the conventional lessons out of the way:

Exercise. Eat less but say yes to vegetables. Personal finance, good. Toxic work environments and friendships, bad. Love others, even when loving yourself is hard. No one really knows. 

Now for the Me-specific things.

My Biggest Regret
I wish I could take back the hundreds – thousands if I’m honest – of hours I spent worrying about something instead of just taking action. 

Tell me if you have ever done this before: it’s Friday night, and though your mind is exhausted from the work week, you are brimming with a never ending list of perfect activities for your perfect weekend. You feel excited, you have a tranquility that doesn’t come any other time of the week, and you finally feel a relief from the pressure of choice. 

You give yourself a pass on Friday night though, and you let the Netflix recommendation engine take over. You blink, and it’s Sunday at 5pm. You did nothing, out of fear of needing to choose. You never did manage to leave the couch except to meet your DoorDasher at the front entrance of your apartment building – which you do in shame since you had to walk past the gym to get there. 

In the last precious hours of the weekend, you rush to throw in a load of laundry, you take the dog for a walk because that is totally the same as 3 Beachbody workouts, and you manage to batch cook something, usually something with eggs since you always have that in stock. 

I think I lived this way by default in my 20s. The knowledge of death kept me paralyzed because I was terrified of making a wrong choice. But I regretted it all the same in the end. 

A Skill I Had to Learn
I am excellent at short-term planning, the art of the daily checklist and weekly priorities. And I was always eminently good at long-range planning. You know, the 5, 10, 30-year life goals. On a quarterly basis, I would publish a new Life Plan to my Evernote and Joe’s inbox. 

I experimented with many different frameworks – god, so many frameworks. One version worked backwards from success metrics by the age of 60 and traced those metrics back to exacting activities. For example, and this is from my actual 2014 Life Plan v3 – 60-year-old success metric of “Understand everything humans know about the workings of the universe” is broken down to an immediate 6-month goal of “Accumulate a detailed knowledge of the last 200 years of human history.” So realistic all around. 

To be fair, long-range personal planning isn’t bad. Life Plans aid with discernment and encourage focus. Some elements of my Life Plans have materialized, albeit not on the timeline I expected or in the manner I anticipated. But alone, Life Plans are inadequate. What I had to learn was medium-term planning, the 1 to 12-month range. Whereas long-range plans encourage focus, the medium-term plans force focus. I used to think that working backwards from a nebulous goal was enough, like this one from my 2019 Life Plan, “See the wonders of the world.” But it needed to be coupled with a medium-term goal like “Join a sailing club. Start taking ASA classes. Become a skipper.” 

I had an aversion to medium-term planning because I would have to make a choice, and that choice would close off paths. This goes back to the aforementioned worrying. If I never forced myself to figure out how I would manage to see all the wonders of the world, then I could not only become a skipper, but also a pilot, or a professional anthropologist, or a documentary filmmaker, or abandon everything and build a house from scratch on the Big Island and explore the wonders of my backyard garden. 

But in 2019, I made a choice to focus on just one thing – sailing. And in 9 months, we finished all our ASA certifications, learned to sail on both a monohull and catamaran, and skippered a 200-mile journey up and down the San Diego coast.

Looking back, I am almost as proud of the fact that I fully explored my other desires. Until I truly asked myself if I really wanted to start over as a documentary filmmaker, in my mind that life path had equal weight as everything else. But the minute I examined the desire more, it fell away like a whim. Because I really do not want to become a documentary filmmaker and all that would entail. Instead, I am drawn to the power of stories, and what I really desire is to become a better writer. Which led to me launching and starting to self-publish essays such as this one. Though, I really do want to become a badass pilot – and I will in a few years.

Some Things Take a Long Time to Heal – And That is Okay
I was fortunate in some aspects of my childhood. But not at all in others. It took me years of being with a loving partner to fully trust him, to believe it was real. I got there on this one. But I still struggle with loving myself, and I accept now that I will need to continue working on this well into my 30s. I know I am being vague on this. I am not yet ready to write more about this yet but will someday. 

It is hard to know how to close this out, except to say: I wish I could take these words, hold 20-year-old me gently in my palm, and whisper them to her every night while she sleeps. But it’s never too late, and I feel a little clearer and more ready for the next 1-12 months.