Thread: More of the wrong thing is less
(or, how I stepped off the hamster wheel)

I’m going to share a personal story with hope that it inspires at least one person to re-examine their definition of success

Through hard work and an unfair share of luck, I’ve done some cool “bucket list” things in my career:

Raised VC from the worlds’ top firms
Helped build 100’s of millions in revenue from nothing
Rang the bell at the NYSE
Met & did deals with billionaires & business icons

These are things I dreamed about when I was young and I treasure some of the memories. But when they finally happened I felt surprisingly unfulfilled. I was scoring lots of points but didn’t feel like I was winning.

Then a few years ago during a board meeting I had a moment of clarity. I looked around the table at 10 people, all absurdly successful by financial measures. There wasn’t a single person I wanted to emulate. Most were unhealthy and several had told me that they were unhappy.

Within months I walked away from from a 7-figure salary, moved my family to Boulder, & haven’t looked back. Don’t get me wrong, I’m a capitalist & like money as much as anyone. But for me it's not the thing, and *more of the wrong thing is less*.

Too many of us build our career without being deliberate about what we’re building *toward*. There’s a famous Yogi Berra quote, “When you come to a fork in the road, take it.” I used to recite this quote a lot - when opportunity knocks, I answer! But...

...over the years I've realized that opportunity can become a trap. Here’s why: Smart, driven people (I’m talking to you Enneagram 3’s and 8’s) will find a way to succeed in just about any situation. This can be both a blessing and a curse. The blessing is obvious, but...

...the curse comes when you point your talent & energy in the wrong direction and it quickly compounds into a monster that you never intended to create. This “achievement trap” doesn’t get talked about but it’s real.

In my case after 20 years of pursuing a misguided definition of success, I hit a wall. I couldn’t spend another day chasing more of the wrong thing. I thrive on ideas, creation, & human connection - money and status aren’t my “why”.

The good news is we can hit always hit CTRL-ALT-DEL. If you build the life you once wanted, then realize you were wrong, you can reboot, scary as it may seem. This means you will have less, but less of the *wrong thing*, which makes space for the right things.

Paradoxically having less tends to result in a feeling of abundance, whereas having more - especially of the wrong things - results in a feeling of scarcity (a.k.a. “The Rat Race”).

We know many of these things to be true at an intellectual level, but rarely do we take action. With less, we make room for life’s most important things, which aren’t really things at all. And in yet another paradox, this tends to result in more success in all its forms.

Ultimate wealth is control over your time. If you don’t believe that, then ask yourself this: Would you trade places with Warren Buffet if it meant being his age (90)?

For me wealth means allocating my time like this:

Time commuting to work: Zero
Time in meetings/offices: As little as possible
Time creating (alone & w/others): LOTS
Time helping others: LOTS
Time with family: Always present & available
Time rock climbing: LOTS

When I started my career this would have been considered impossible, even laughable. After all, it’s a violation of the American Workaholic Ethos, where long hours in the office is a badge of honor regardless of results.

Fast forward 20 years and one pandemic and the world is beginning to embrace a new way of working. But - and this is the entire point of this thread - it only happens if you’re deliberate. You have to stop chasing more of the wrong thing, even if it looks like success.

I recognize that even having these choices is a huge privilege that most don’t have. That said, most people have more control over their lives than they’re willing to admit. We like to point to external constraints when the truth is that most of our limitations come from within.

If you’ve read this far then you’re by definition the type of person can define and achieve your own version of wealth. May 2021 be the year that journey begins...

(Thanks to @sweatystartup for keeping it real and inspiring me to post this.)