Why I am no longer pursuing wealth, "impact," or "success"

We are meant to *play* and there is a much better game to play if you want to be genuinely happy

Read Time: 6 minutes

Whenever friends ask what I am doing work-wise these days, I don’t have a clear answer. I am doing lots of things, and I am doing nothing.

One thing that I can say I am doing is having fun.

But that has never felt like a satisfactory answer. I want to be able to at least explain what I am working toward.

I like advising founders/startups in the education space, sure. But is it the thing I want to do with my life. No. I’m not trying to build a consulting empire.

I like helping with “growth” because it’s a process of collaboratively developing hypotheses and running the most promising experiments to test those. But do I want to become the world’s foremost expert on “growth strategy”? No. I truly couldn’t care less about pigeonholing myself into being known as a growth strategist.

So what am I really trying to do? I ask myself this over and over.

This week’s post is inspired by the idea that you should give yourself the advice you would give a friend.

What advice would I give to a friend who doesn’t know what they are working toward? Well that’s easy for me to answer: I would tell a friend to just have fun.

Fun might sound like child’s play, but I think it’s much more profound. Hopefully this post can help begin to explain why :)

“Be like the fox who makes more tracks than necessary, some in the wrong direction.” -Wendell Berry’s Manifesto: The Mad Farmer Liberation Front

Wealth = Impact = Success = Happiness

That’s what we’ve been led to believe right?

Seemingly everywhere I go, I am sold a formula that goes something like this:

the more wealth I can generate, the greater impact I can have

the greater my impact, the more successful I will be

the more successful I am, the happier I will be

Becoming successful is the game we’re told to not just play, but to win. The conditioning is so strong that I played this game even with parents who didn’t.

For all my dad’s flaws, it was a privilege to be raised by someone who is so deeply committed to a communist philosophy that all humans are equal. I was reminded daily that no one deserves or is entitled to more, no matter how wealthy they are. Period.

I did not grow up learning how to “get ahead” in life. Instead, I learned about how the impulse to get ahead inevitably, and invariably, leaves others behind.

And even with that drilled into my head, still I tried to get ahead.

Working at a food bank after college, I saw how the Board members walked into the building once a quarter and, with one off-handed remark, would completely turn our entire organization upside down.

Of course we listened to the Board members because the Board members were successful.

They were successful, because they were wealthy. And they were wealthy because they were smart.

We food bank employees and volunteers and clients were not wealthy, so it followed that we were neither successful nor smart. Why listen to our ideas?

So we would drop everything we were currently doing to work on one of their pet projects, which would surely lead to the organization to success!

One Board member had the brilliant idea to do a direct mail fundraising campaign to all the factories in Winnipeg that no one had heard of. He once drove through an industrial area of the city and realized how much money these businesses must be making, so he suggested driving down all the backstreets to take down the name and address of every one of these businesses.

I tried playing my dad’s game of sacrifice, and that is how I ended up roping my boyfriend into driving me slowly up and down all the industrial streets in Winnipeg for a few weeks for a campaign that led to $0 in donations.

So I decided to play the success game. I was easily as “smart” as these Board members. I just needed to leverage that to build some wealth so I could start to put the formula in motion.

Wealth = Impact

Impact = Success

Success = Happiness

I applied for an MBA and went to work in tech. For the next ~dozen years, I believed in the wealth=impact=success=happiness formula.

The implicit goal was to create as much distance between myself and others as possible, in pursuit of the success that would allow me to walk into a building once a quarter, and with one off-handed remark (and very little context), change the way things are done.

I wanted to be taken seriously.

Unfortunately (!!) the recipe that turns wealth into impact into success into happiness does not hold up to scrutiny. Or lived experience.

In our quests to become more “successful,” we separate ourselves from each other, and separation makes us miserable.

I was happiest at my poorest, for example. And the greatest impact I’ve had is at an individual level.

The happiest people are playing a different game entirely.

Their recipe is simple: optimize for fun.

It’s surprisingly rare to encounter people playing this game, but it’s so memorable when I do. I think we can all immediately name the teachers and coworkers we’ve had who were having fun.

I think it’s easy to assume certain jobs are more fun than others, or certain people are just born with more of a propensity to fun, but I disagree.

Every time I go out, I can see that some flight attendants, servers, baristas, cashiers etc are having more fun than others. Why?

I believe fun is a mindset that we can choose to nurture and strengthen. Not only that, I believe it’s the foundational mindset that we should focus on cultivating (over say, one of gratitude or growth, which I think naturally follow if you focus on having fun).

We’ve lost the art of having fun in our careers. Everyone is trying to teach you how to be so 👏 damn 👏 serious 👏 about your career.

When I think back to my job at the food bank, my favourite part was chit chatting with volunteers. It was the thing that helped me get through my day. The only thing I looked forward to.

Chatting with volunteers wasn’t part of my job. In fact, I was doing it to avoid doing my job. And yet, I would take that job again just for the opportunity to have those random conversations again.

It was fun to engage with people from all walks of life, from retired teachers to refugees from South Sudan. That might not be what everyone considers “fun” (fun is very personal!), but it was my idea of fun.

I don’t think a wealthy or “successful” person (ie the Board members) would have given these volunteers (most of whom were food bank clients) the time of day.

I’m sure they’d be kind to them (to be successful I do think it helps to be kind), and I’m sure they’d abstractly care about their wellbeing (I think nearly everyone would), but to be truly successful in our society, you have to focus your time on people who can help you get “ahead.”

Why waste time talking to someone who doesn’t even have a job, let alone money to afford their basic necessities.

I am sure that this kind of closed mindset precludes fun.

I actually, somewhat randomly, have become friends with the daughter of that Board member who had the idea to do a direct mail campaign to all the factories in Winnipeg.

We both live in New York now. She followed in her dad’s footsteps and became a lawyer. She, like her dad, is very successful. She, like her dad, tries to give back by being on non-profit boards. Unfortunately, not only is she miserable, I now know her father is too.

The last text exchange we had, she told me she “hit a really significant point of unhappiness, especially as (she gets) closer to 40 and (doesn’t) have a plan.”

She went on to say she was “really questioning (her) life here these days and wondering what (she has) to show for all her years working at (the bank).”

I don’t have a plan either, and I don’t know what I have to show for all my years of work, but at least I can say I had (and continue to have) fun.

“If we were to learn one thing, it would be to free ourselves from any beliefs or baggage or dogma that gets in the way of us acting according to our true nature.” - Rick Rubin

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