-Robin Williams
Before starting Ender, we almost had an additional founding team member. Let’s call him Lovechaser. Lovechaser had deep operational experience from his previous startups and approached problems by breaking them down into concrete, solvable steps. Every problem was solvable, or so he thought.
Besides looking for his next business endeavor, he was also looking for his soulmate—the woman he would marry and spend the rest of his life with. Lovechaser had a list of traits and searched the country for his partner using dating apps, matchmakers, and referrals. He did screening calls with prospects and then flew to meet the women he talked to, batching prospects by city.
Lovechaser didn't join us because he prioritized searching for his soulmate over his professional life. I recently caught up with Lovechaser and asked if he had found his partner. He didn’t, and after following years of his rigorous process, he gave up.
Hefty Decision
I think about this chart a lot. I very much enjoy my alone time. Your partner is the most important life decision you make. Personal and professional, as the renowned investor Paul Tudor Jones says:
…one of my No. 1 rules as an investor is as soon as my manager, if I find out that manager is going through divorce, redeem immediately. Because the emotional distraction that comes from divorce is so overwhelming. The idea that you could think straight for 60 seconds and be able to make a rational decision is impossible, particularly when their kids are involved.
That’s the emotional destruction divorce puts on someone. So, to be sure, should we be methodical Lovechaser style?
Lists
A list of dealbreakers is better than a list of wants. The opposite of your dealbreakers derives a list of needs. It’s illuminating to understand your needs.
I like to think my list of needs helps. Maybe it does. I hope it does. However, each time I’m in a relationship with someone, and it doesn’t work out– I discover an unknown unknown need and add it to the list.
In reality, there are multiple matches for everyone, resulting in differing degrees of happiness and fulfillment over different timespans. That reality isn’t helpful, though. We need selection criteria.
My dad always tells me, “Everyone is crazy. Find someone who is crazy in a way you can deal with.”
Personality and Character
I used to screen purely on personality. Do we vibe? Can we talk for hours on end? Personality is important, but that led me into traps. People who keep my interest often lack the character traits I value.
Younger me viewed character traits I didn’t like as fundamental flaws. That was naive. Character traits I don’t value in a life partner can be fun in a friend or for someone who wishes to live a life with alternative goals to mine.
I recently watched a show where there are humanoids and humans. Humans and humanoids are essentially the same in every way. There’s a humanoid boy who is an extraordinarily gifted pianist, but he had emotional outbursts where he’d push and yell at other kids. The humanoid boy’s parents alter his programming so he no longer has emotional outbursts. It works, and he becomes friendly with his peers; however, a side effect is that he can no longer create inspiring music.
The outbursts were a feature, not a bug, of the humanoid boy’s personality.
There’s something about emotional extremes that can lead to greatness in art. Whether these extremes lead to greatness in relationships is… debatable.
Learnings
Whenever you find an intractable problem, it’s because you misstated the question. You haven’t given the right question. You assumed something in your question that was fundamentally wrong.
You can’t fake character. Who someone is at their core rarely changes. You can’t fake chemistry or fake deeply caring for someone.
You can’t force love. It’s not checking boxes Lovechaser style. You can’t rationalize love. We need to play the game. The only way to lose is to stop playing. And the only way to win is to keep playing. As Phil Collins says, you can’t hurry love.