Don’t Be So Hard on Yourself

One way to characterize life is as a series of good advice not taken. Maybe it’s your friends telling you to quit that job that you hate yet still choose to stay. Maybe it’s that 4am drinking habit you complain about when you’re hungover the next day. Maybe it’s when in high school your mom told you to study for the SATs and you chose to put it off until the month before.

There’s plenty of reasons why we chose not to follow good advice. One could be sheer laziness and inertia. It could be an ego problem, where taking the advice is admitting to yourself there is a problem to address despite the signs being all too obvious. For some people, it could be that you have two conflicting voices in your head telling you opposite “good” advice that while both can be simultaneously true, you know the real answer lies somewhere in the middle. Okay – the last one is more of a “me” issue, but the point is, even the best advice in the world doesn’t necessarily come easy to swallow.

In my unhealthy pursuit of endless optimization of my life and goals, I often think back towards former versions of my self – high school Jerry, college Jerry, etc. – and wonder how differently my life could have turned out if I had known even a small fraction of the knowledge I do today. Where if I previously understood the importance of discipline, could I have gotten better than a 3.5 GPA in high school and maybe even made it to an Ivy league school? Where maybe if I valued my intellectual curiosity more in college, could I have taken more academic classes vs missing 9/10 lectures to go drinking with friends. My life journey has been littered with many of these “what ifs” and other forms of destructive curiosity that despite my best intentions, still leaves a persistent phantom pain that I feel even today.

During these curiosity episodes, I like to remind myself of a thought experiment involving reading the same book (or other content) twice. For the same exact 50,000-word text – if you read the book once in high school, and again now, you can get two profoundly different takeaways. And despite being the same exact words, based on the point of your life you are at, your understanding of the book as it relates to you can be wildly different.

A simple example of this is when I first watched “500 Days of Summer” as an angsty high school teen. I remember loving the story and resonating with Tom’s feelings of heartbreak. But now when I rewatch the same movie, I start to pick up all the red flags along the way and now empathize with Summer’s point of view. Even if today’s Jerry were to have a conversation with high school Jerry on all the things he has learned, like a stubborn younger sibling, high school Jerry would be unlikely to listen or even begin to understand. But it’s fine, because even though I’m not the person I was back then, he was still who I needed to be in order to become the person I am today.

This destructive curiosity, or even rephrased as having a chip on my shoulder, has served me well for several years, to push me beyond the limits of what I thought was possible. Even 2.5 years ago right before I moved to NYC, the immediate possibility of living in the Big Apple never even crossed my mind. Though on the flip side, constantly living a “directional” life and always seeking to vaguely “do more” versus being satisfied with things the way they are leads to dangers of both burn out and the loss of your own sense of identity.

As much as this blog is one I want others to read, this post (like many others) is also very much a topic I struggle with and I’m writing for myself as a daily reminder. That you can only do as much as you can. That you can only know as much as you know. That if something doesn’t work out, it’s not because of you, and wrong question becomes “what could I have done differently”. Maybe it didn’t work out because it was the wrong opportunity for you as a person at this point in your life. And although it might not seem this way right now, maybe things actually worked out for the better.

One gratitude exercise* that has helped me begin to overcome these thought patterns is visualizing your past self and accepting them for who they are despite all their flaws and shortcomings. Despite “knowing less,” it was them for exactly who they were that allowed you to be the incredible person you are today. They didn’t need to know more than they did. They didn’t need to do anything differently or “more”. Things just worked themselves out.

Even for the part of me that’s so hard on myself for so much of my life, I still deeply appreciate that part and all the pain it has created along the way because if it hadn’t, I wouldn’t be the person I am today. But today is the day to stop treating myself this way. All it takes to begin is a small step in the right direction.

* Exercise courtesy of Nick Hong. Can read about it in a much more well-written form here

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