I was required to complete my homework immediately. Then piano practice, yardwork, or other household obligations. Same with eating…unpleasant vegetables had to be consumed first—only then could I eat rice, meat, fish.
Leisure time was ridden with guilt. Don’t you know successful people read, instead of playing video games? Don’t you know that you’ll get fat if you stuff yourself with candy after finishing your fruit?
So I learned conscientiousness. And within this strict system, I found shortcuts.
Turns out when the teacher drones on and on about stuff I already read in the textbook homework reading, instead of paying full attention, I could complete my homework during class. I could preset my locker to the first two numbers, so the third could be rapidly input and off I went for the afternoon.
With my homework done, and a bit of reading too, I could focus many more hours on video games. I was ahead of the pack; I was good at learning. It was easy and enjoyable.
I became impatient when I wasn’t learning. When the teacher wasn’t challenging the class.
As school became disappointing, room opened up for sports, extracurriculars, hanging out with friends. Opportunities arose to do interesting work, and my resume expanded. I was admitted to exclusive, prestigious colleges.
The typical trajectory for this student profile is to continue hyper-productive excellence, over time translating academic skills into professional ones. One can imagine a few archetypal journeys: the founder, the doctor / lawyer / trader / consultant, the professor. Maybe there’s a mid-life crisis at some point. A meaningful shift in life orientation. Some social impact, or political activism and influence.
To me, the best route would be entrepreneurial—my own boss. With years of “success” in zero-sum academic accolade-laden environments, I had full confidence I could do whatever I put my mind to.
But I was missing a critical ingredient, which became more and more apparent throughout college and then for some time afterwards. At first, I thought it was an idea, a field of interest. But now, five and a half years later, I recognize the problem was precisely specified by Gian-Carlo Rota (lesson three): it was a how as opposed to a what.
I had forgotten what hard work was. I had become sensitive to challenge. I had put myself on a status pedestal, where stepping down would be deeply, subconsciously threatening. Even if it meant I could then step up to an even higher one.
I grew bad habits. Beneath the surface, my attitudes became rigid. I retreated into myself and let my ego stew. I was trapped in an isolation vortex, unanchored and uncertain how to focus my time. I lost the ability to show up and get things done, well—especially when I didn’t like what I was doing.
I was both depressed and in denial. I didn’t listen to other people. I did whatever was top of mind, shiny and distracting. I spent more time creating bizarre, convoluted stories of how everything fit together than actually spending the time and effort to fit things together. Fulfillment and meaning and ambition became hollow words.
Eventually, finally, I started to confront and recognize these problems of motivation, purpose, identity. I decided it was time to get a challenging job, establish realistic personal goals, and chug. Build a foundation. Start somewhere, anywhere. Embrace the things I have known all along. Be pragmatic yet joyful each day. Slowly change myself and my attitude in order to (one day) change the world, instead of trying and failing to leap ahead.
I was lucky to have a strong resume and network and other gifts from my past self to rely upon. I was lucky to find Seth Godin and Steve Pressfield and other resources. I don’t think there are any shortcuts to fulfillment and meaning and the good life, so it’s unbelievably fortunate that I am where I am.
With my prolonged existential crisis (multi-year, physically crippling anxiety), I emerged humble, shaken. Yet strangely confident that I wouldn’t let such a discontinuity affect me so badly ever again.
Ultimately, this is life. The roller coaster journey to find fulfillment and meaning, to increase the value of each moment. To improve. To serve. To contribute. To work. To reflect. To give thanks. And to endure.
I’ve never lost confidence I can do whatever I want. But I’ve gained a lot more pragmatism in how those things can be achieved. It takes time. And we only have so much of that.
Cycling through good and bad has brought me better balance. Getting lost in the complexities of deriving meaning has shown me to stick with simplicity. I’m grateful for my life, and so unable to desire retroactive changes, to hold weighty regrets.
I’ve been very lucky, but also part of the journey has been self-fulfilling optimism.
I hope when you encounter rough patches, when you get lost, that you can find the strength to hold out and push forward. To try and try again. It’s hard work, but ultimately that is itself fulfilling and meaningful.
You can do it. You’ll see. You can and will.