How Do I Define Success?

Seriously, how do I define it?

What does success mean anyway? It’s so subjective. Some people look at the size of their bank accounts, while others look at what their progeny are able to achieve. There are lots of different ways to look at it. But if I’m being honest, I’m not asking for anyone else. I’m asking for me. I’m statistically over halfway through my life and I still can’t define what success means for me.

I’ve made more money in the past few years than I ever have in the past. It’s not obscene amounts of money; it’s enough to live comfortably. Still, it doesn’t exactly feel like I’m successful. Don’t get me wrong, I’m one of the lucky ones and I know it, especially in the pandemic world of 2020. It’s nice to have enough to buy pretty much whatever my family needs, pay off the credit cards every month, and save for a rainy day.

Where did that saying come from, by the way? What happened on some rainy day however many years ago that was so bad it spawned an idiom?

By most measures, I’m very successful. Sure, I’ll grant you that.

Not only that, but I was dealt a hand from birth that almost guaranteed I would have some amount of success:

  • I’m a man.

  • I’m white. Let’s be real, this has given me more advantages than even I can realize.

  • I’m tall. 6’ 1”. But not freakish tall where it’s all anyone asks about when meeting me.

  • I’m attractive enough.

  • I’m in decent shape without having to do crazy amounts of exercise or fad diets.

  • I still have a full head of hair in my 40s.

  • I haven’t had any major health issues. Although I do pass out easily, which is more funny than anything else.

  • I grew up in an upper-middle-class family in the suburbs with two loving parents. At least, I think we were upper-middle-class. I actually don’t know the cut-off between middle and upper-middle-class.

  • I have a younger brother that I’ve never fought with. Besides that one time when I punched him and gave him a bloody nose on accident.

Plus there are all the things I’ve been able to do that most other people never get to do. Things like record an album and tour in a major label signed band, or play in the World Series of Poker. Of course, I look at those things as failures sometimes too.

And not to mention, my incredibly supportive wife, Allison.

There’s another weird saying. Not to mention? But I literally just mentioned it! Suffice it to say, she’s amazing.

So what’s the problem, right?

Why am I so stuck on this?

Why have I been grappling with my purpose in life and how I spend my time so much?

Is this just a mid-life crisis and I need to get over myself?

Is this my version of the guy who used to come to the golf course I worked at who had a brand new sports car and a super obvious toupee? It was so sad. I felt for the guy. Man, he was a terrible golfer too. Poor guy. Maybe he was thinking of writing a book back then like I am too. Oh, man. I hope he’s doing ok now.

It doesn’t help that most advice on success can be reduced to the “draw the owl” meme. First, draw some circles for the owl’s body and head. Second, draw the rest of the fucking owl. First, find your passion and purpose in life. Second, turn it into something wildly fucking successful.

Does any of this really matter in the grand scheme of things? I mean, we’re essentially a bunch of apes that figured out how to communicate and build things. And we don’t even live all that long. We’re born, we grow up, we procreate, we grow old, and we die. When you boil it down, our basic purpose in life is to create little versions of ourselves and carry on our genes. And when we die, we’re forgotten about relatively quickly. The Earth still keeps spinning, countries are still at war, politicians are still driving people crazy, the stock market still keeps going up — or down, I don’t know, I can’t predict the future. People are still living and laughing and loving and fighting and consoling and hugging and kissing and hoping. My death, while tragic for those closest to me, will have zero impact on the stock market.

Or are these just the existential questions we all end up asking ourselves at one time or another?

Maybe you’ve been nodding along the whole time. Even if you’re not a white guy of slightly above-average height and a full head of hair at 42.

This is all part of the human condition, isn’t it?

And here I was thinking I was unique.


I wrote this very late one night earlier in the summer. I was feeling frustrated and down. I blurted this out onto the page almost exactly as you see it above. It felt cathartic. I shared it with Allison the next morning. She loved it and said I should publish it back then. I was hesitant to because it was a raw, vulnerable moment when I wasn’t my best self. Yet the more I’ve thought about it, the more I’ve come to realize we all have those moments. Those moments when our intellectual self takes a back seat and our deeper, darker emotional self comes out in a sudden burst. With stress levels at unprecedented highs, I can only imagine this is happening to people more often this year.

In my case, I’m channeling that energy onto the page and working towards a definition of success that’s not tied to a monetary outcome in the short-term.

I’m not going to be perfect. But I’m using this famous Bill Gates quote as my North Star:

“We always overestimate the change that will occur in the next two years and underestimate the change that will occur in the next ten. Don't let yourself be lulled into inaction.”

It’s too easy for me to put things off until tomorrow. Because tomorrow becomes next week, which becomes next month. The next thing I know, years have passed and I’m still frustrated and feeling stuck. Not this time.


Thanks for reading all the way to the bottom. I’m honored. In a world where attention spans are getting shorter each day, it means a lot that you’ve spent this much time with my writing.

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