On What Success Looks Like

I used to think there was a specialty/industry/profession (aka “IT”) that I was meant to be doing. I just had to find IT (“I’m a doctor! I’m a consultant! or I’m a businesswoman!”), work hard, and all the other pieces would fall into place.

I’d have a big title at a big company with a big salary doing a thing that everyone would be impressed with and maybe, even a little jealous of.

I started imagining myself in power suits before I ever put a suit on and realized how uncomfortable they were.

I remember thinking, “I should be CEO of a Fortune 500” without understanding what a CEO did or what the Fortune 500 was.

I pictured myself on the covers of magazines and being interviewed about some awesome thing I just did b/c I was fucking amazing at whatever IT was.

Luckily, I found my first IT at age 10. I knew I wanted to work in sports after going to my first Knicks game and decided soon after that I was going to be Commissioner of the NBA. I didn’t waver much from that for the next dozen years and everything work-related I did from there on out was driven by that goal. (And maybe… a penthouse in Manhattan and a house in the mountains with 2–3 perfect kids and a yellow lab named Bailey.)

When I got to the NBA at 22, I thought I’d made it… the dream was coming together, I was on the ladder I needed to climb and I just had to put one foot in front of the other. So simple.

But jobs and corporations are messy and political and bureaucratic and 2 years into it, I had to admit to myself.. I don’t think I want to be Commissioner of the NBA anymore.

I got IT wrong, the future seemed uncertain, I beat myself up for not making the right decision, I thought I was a failure, etc, etc.

But after a few months off, a cross country roadtrip, many late nights bartending and lots of alone time reading in Central Park, I pulled it together enough to revisit the drawing board and try to figure IT out again. I thought, I got it wrong for the last 12 years of my life, but now I was more mature, more experienced and less naive than my 10–22 year old self so, this time I’d get it right and I wouldn’t have to go through this shit again.

Next IT — Head of Marketing for ESPN! A few years later… same shit.

Next IT — I’m gonna work in food and start my own bar/restaurant! Yes, again… same shit.

I was great at (or delusional in) overshooting and jumping to the end result I thought I wanted to achieve, but was terrible at getting super clear on the WHY.

In my defense, I thought I had sorted the WHY. But it was the lazy version, which netted answers like ” b/c I love basketball!” or “b/c I want to focus on the consumer,” or “b/c I get to create/attend these incredible events that most people only dream of,” or “b/c I’m obsessed with restaurants!”

Problem is, not going deep and getting super clear on the WHY usually made me feel like I had to start from scratch each time I lost interest. Sometimes it took a few months to realize that and other times it took a few years, but eventually the lazy WHY couldn’t hold up b/c it wasn’t solid enough to support the path I chose.

After a bunch of different jobs at a bunch of different companies in a variety of industries, revisiting the drawing board many times over, starting my own business and taking multiple breaks to “find myself”… it’s now clear that finding an IT isn’t enough. Seems so obvious now, but it took a few turns for that to sink in.

That’s not to say I didn’t learn a ton with each choice I made and I really don’t regret any of the decisions made, but the process of choosing a path, committing to it all in, starting to see the cracks, reconciling conflicting feelings between what I felt deep down with what I thought my goals were, finally admitting that I had to make a(nother) major life change, then actually going through with it, was fucking brutal.

So, instead, here’s what I do now. What sustainably sets me up for fulfillment in the long run is understanding:

  1. What I want to accomplish in life long-term
  2. What I value in work, in relationships and in my home/community
  3. What my day to day environment and interactions entail

Answering these gives me a set of north stars regardless of what job I have, what circumstances I’m in, how much money I make, or who I’m surrounded by and they are entirely dictated by my own WHYs for being.

I may not have them all right now and they may evolve later on, but at this moment they are the fundamental hopes, dreams and desires for what I want my life to look like. Together, they add up to my definition of success and what a good life looks like and I use them as the filters through which I make the big decisions.

The exercise seems simple, but the process isn’t always easy b/c it requires digging a few levels deep into your WHYs and that can be uncomfortable. As a rule of thumb, 3–5 follow up WHY?s after the first answer you come up with is a good measure to get into the real shit.

After that, staying focused on what you come up with isn’t always easy or popular. Our parents, friends, society, schools, the media are all responsible for creating and propagating set definitions of success and what we should be doing with our lives. We’ve all been influenced by it in some way, big or small.

It’s definitely messed with my head many times over and it still does sometimes. But each time that happens — a friend says something that challenges my choices or something triggers a doubt in my head on whether I’m doing the right thing — I have to remind myself what my own success definition is. And I have to do it emphatically and confidently… 100% conviction

What I’m fighting against aren’t just my own doubts in the moment, but the entrenched societal norms that have been working their way through my brain since I was born. Those norms had evangelists in the form of my mom, relatives, guidance counselors, professors, bosses and over time they even convinced some of my friends, significant others and coworkers to join the cause.

It’s incredibly easy for others to tell me all the things I shouldn’t be doing b/c they don’t have to live with the choices. In addition, the more criticism I’ve gotten, the more I see that it’s less about me and more about them and their uncomfortable feelings that are triggered… whether it scares them, makes them jealous, threatens their beliefs, makes them question their choices, etc. All that makes it easier to ignore the noise, remember that we’re all trying to figure our shit out and no one knows any better than anyone else. And certainly not when it comes to how other people should be living their lives and what success should look like.

So, do you know what your success definition is? If you take a stab using the framework above, let me know if I can help.

Much love,

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