Try This Instead of Making Resolutions or Looking Back at 2023

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Last night I was doom-scrolling Medium, trying to find an article that was interesting, timely, and not about making resolutions for 2024. I already believe in systems, not goals, and my life is pretty great right now, a realization that came after a lot of self-improvement and a little spiralling mid 2023. No resolutions for me. 

My son asked me yesterday how I would rate last year. I gave it a solid 8 out of 10. I asked him for his rating and he said 7/10. “Only a 7?” I asked. “You told me you had two of the best weeks of your life, on that cruise with your cousin in the teen club, and that week at summer camp!”

He responded, “Yeah, but that’s only two weeks. And there was that boring week in Europe when all we did was go to restaurants.” He then added, “I think I might be a hard marker. I don’t know what would make for a 10.”

Amazing how teenagers and adults view things differently. I loved that family time in Europe — but when I think about my childhood, how many of my happiest memories involved my parents? Not in the top ten, that’s for sure.

This morning, starting 2024, I called my sister and asked her the same question my son asked. She gave last year an 8 out of 10, adding things were going pretty well, but there are always challenges. Then she told me about this exercise her business coach had her do, that involved looking back at her whole life, not just the past year.

Here’s the gist of it. Divide your life into segments, I chose decades, of which I have six. Then think about each segment and what your biggest challenges or failures were at that time. This might trigger some negative self-talk or remind you that you’ve had a difficult life, but it’s worth it.

Next, take the failures of each segment, and think about what you learned, and how that improved future segments. 

Boom.

For me, even as I was listening to her I was doing this mentally with some of my biggest failures, and realizing how powerfully positive my life became afterwards, specifically in response to the pain caused by failure. It was a lovely way to start 2024!

Here’s my version. 

0–10: Painfully Shy and Bullied

That bullying led to me being a loner at school. It made me comfortable being an outsider and holding unpopular opinions. 

Later in life, it allowed me to ignore criticism and follow paths that led to great success, both socially and economically. If nobody lets you follow them, you have to become a leader. For a long time, it was just me leading myself. Turns out, that was ok.

11–20: No High School Prom

I started to make friends, but the one girl I asked to my Prom turned me down, and I was too embarrassed to ask anyone else. I also got rejected by my number one choice university, MIT. 

Neither of these killed me, and later in life, I became audaciously ambitious with my goals, not fearing rejection. This included meeting my current wife, who is so far out of my league that I’m still a little astonished, 17 years later, that we’re together. 

21–30: Unhappily Married

I was engaged at 24, married at 25, and divorced at 30. Plenty of blame to share, but suffice it to say that we fought too much, communicated too little, and had very different expectations of life. 

Later, this allowed me to recognize a good relationship when I had one, and to work hard to preserve it. I also got my daughter Nikhita, who is one of my best friends and staunchest supporters, despite my not being there for her a lot in the early years. 

31–40: Bankrupt and BiPolar 

I started a company, lost $500k, and had to declare both corporate and personal bankruptcy. In the aftermath, I thought I was depressed, but it turns out I was bipolar, which seemed much worse to me, making even my positive periods feel like a disease. 

And yet, looking back, the recovery from bankruptcy was one of the best periods of my life. I became more humble. I learned to manage cash. The climb back up was exhilarating. And after the diagnosis, I got on Lamotrigine, a drug that transformed my life, smoothing out the highs and lows.

41–50: Fired and Looking for Revenge

I was fired from the company I co-founded and sued my former business partner. I learned a lot about employment law that helped me in future endeavors, but mostly I learned to let go. I won when I stopped caring and got on with my life. 

Oh yeah, and a year later I bought back the whole company. 

51 -58: Losing Money and Sleep

Ok, ignore for a moment that to lose a lot of money I had to first make a lot of money. This exercise is about failures. 

I lost a total of $20 million in two short years, on a combination of bad businesses, owning restaurants and retail during COVID, and a meltdown in psychedelic stocks. It still hurts, it was only two years ago. But I learned a ton about investing and even more importantly, about not basing my self-worth on my net worth. 

After some initial angst and self-recrimination, my attitude has improved, a lot. And because of risk-management lessons learned from my bankruptcy, the risks I took weren’t fatal. 

And there you have it. Taking just the headlines, I could cry woe is me all day long. But my life is awesome, and it isn’t despite those obstacles, it’s because of those obstacles. 

Change the story you tell yourself about your childhood, your failures, and your pain. You’re awesome, and that’s how you got here.

1. How I lost $5m of that $20m in one go. 

2. More lessons on how not to spend money.