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You did it. Congrats! All your hard work and lucky stars and ancestors' sacrifices have led you to this day: your stock is about to be liquid. And you are about to be rich.
I use the word "rich" quite loosely. It means different things to different people. I knew folks who felt that way with a few hundred thousand, and folks who <i>only</i> felt that way with 100 million. It always comes down to expectations. If you ended up with way more than you expected at this point in your life, hopefully you are feeling delighted.
You have probably already heard the research studies about money and happiness, but here's a quick primer: In 1978, psychologists studied Illinois lottery winners and found that within about a year they were no happier than their neighbors living ordinary lives down the street. Worse, they took measurably <i>less</i> pleasure in everyday things: ham and eggs, pleasant conversations, "wow you look nice today" compliments. Four decades later, economists ran a bigger and better version in Sweden, following more than 2,500 winners for years. The Swedish winners did get a lasting lift in life <i>satisfaction</i> (aka they generally felt better about their financial circumstances, which makes sense). But their day-to-day happiness and mental health barely moved.
What does this tell us? Money buys relief and comfort. But it does not buy joy. That part is still your job.
I was in your shoes once, pre-IPO at the hot company of my generation. We had a hackathon the night before we rang the bell. Some of us felt like life was about to change. Others of us felt it was just another ordinary day — a nice milestone, sure, but with so many already crossed on the path to hypergrowth, what's yet another?
In the years since, I have watched friends and colleagues mature into their new fortunes the way one does into a new pair of jeans. At first you're excited because your ass is gonna look great, but then you realize it feels kinda stiff and awkward. After enough time, though, you sink into it. It becomes another detail in the shaping of your life.
Some of my former colleagues slipped away from tech like aquarium fish flushed into the vast blue ocean, off to find their true homes. It wasn't always who I expected--for example, wildly talented engineers would decide they didn't care to ship impact anymore. I saw folks become chefs, hoteliers, artists, therapists, writers, teachers, parents. This group always fascinated me, because it felt like I was watching some kind of Cinderella transformation. Who would you bloom into, if you had that gift of freedom?
Others pursued the leisured lifestyles of the upper crust: weekly jaunts to exotic places in search of Michelin stars (gotta catch them all!), a sleek new home with tasteful furniture (goodbye, old IKEA!), experts to assist them with said tasteful furniture selection or how to get into the hottest clubs, VIP upgrades to Disneyland and Coachella, five-hundred-dollar hoodies from Japan.
Still others continued on the same track, remaining in tech. Some became founders or VCs, and some continued their march at the same company or at a younger imitation, riding the highs and lows for years and years and years, still chasing the thrill of the climb.
Watching all of this, and living much of it myself, here are the biggest things I wish someone had told me then:
## 1. Money changes your life, but you get to control how much it changes your identity.
I saw this play out in all three groups: among the fish, the leisure class, and the lifers alike. I know people for whom the money simply let them check off life goals like paying off their parents' home or having enough for retirement. They upgraded the car and maybe the house. And then, largely, they stopped. They didn't change how they carried themselves day to day. They didn't change who they hung out with. They didn't take up the game of <i>more</i>. What I noticed about these people is that they could still connect with almost anyone.
On the other hand, the more that access to whatever money can buy becomes part of who you are, the more you become a character to others. You are now that person who eats at fancy restaurants all the time. The one who brings in a full zoo and carnival and running choo-choo train for their 3-year-old's birthday party. Who shows up with rare watches and cars and vintage ports. You may not mean for it to, you may have done absolutely nothing undeserved beyond enjoying what you love, but you become cloaked by all the shiny things your money can buy. And for the people who don't have what you have, this sparkling cloak can be <i>so</i> distracting that they can no longer really <i>see</i> you. You become harder to connect with.
The money will change your life. Whether it changes your <i>self</i> is still up to you.
## 2. Decide what game you're playing
There is a game, and that game is called <i>more</i>. Once the money lands, a question will be waiting for you that many people neglect to think deeply about: am I still playing?
One founder told me, after he already had a nine-figure net worth, that past a certain point the money is just for scorekeeping. It mattered to him because he made it matter: that number was a measure of what he was able to accomplish and how well he ranked against the competition. If you like that game, go for it. If you <i>know</i> it's a game, by all means, play.
The people I worry about are the ones who didn't like the game but kept playing because everyone around them was playing it. I saw this most in the group that stayed, still marching or sprinting on because it was all they knew, running up a score because they were afraid to stop and ask: <i>What would happen if I stopped? Who would I be if not a player who wins?</i>
You'd still be you, and that's quite enough. And I suspect there may be something even more majestic on the other side.
## 3. The life of leisure does not equate to a life of joy.