Changing the world to change yourself

Most people who are trying to change the world are really trying to change themselves.

Sometimes this works. If the change you want is a sense of purpose or the adrenaline rush of winning, then trying to change the world in order to change yourself is probably adaptive. That’s because changing the world can actually do the things for you that you’re hoping it will do. 

But I don’t think this works for most people. That’s because they’re trying to change something about themselves that changing the world can’t actually change. They’re attempting a multi-decade bankshot that’s doomed to fail—but they won’t realize it until they actually achieve it.

I know because I am one of these people. 

.   .   .

Let’s start by defining some terms. 

When I say “people who are trying to change the world” I’m talking about the set of founders, investors, and startup-people who came up in the industry between 2010 and today. When I say “change the world” I mean starting large companies in order to make a big impact and put a dent in the universe. (There are, of course, infinitely many ways to change the world—you change the world just by existing—so I’m using this term in its sense as a slogan of a particular group of people, rather than in its more literal sense.)

There are at least two kinds of personal transformations that we are often looking for, but don’t get, when we set out to try to change the world: 

1. To feel respected
2. To feel loved and connected

It might seem weird to argue that building a startup can’t satisfy your desire to be respected or to be loved and connected. Empirically, building something important in the world will increase the odds significantly that both of those will happen.

But there’s a difference, in my experience, between the “being” and the “feeling” of both of those states. In other words, you can be loved and respected and not feel it, or you might feel it but find it to be imperfect or incomplete, and be driven for ever more increasing amounts of it. 

In my experience, this usually happens when your motivating desire to be loved or respected is subconscious rather than conscious. When that’s the case, both of these normal human needs turn into pathological quests that can’t be totally resolved by any future state of success or connection. But you keep trying anyway.

If you’re a person who is subconsciously driven by a desire for respect, the increasing levels of respect that you get from running a startup will only serve to fuel your desire for more respect. You’ll be terrified that the respect will go away, or that it was not deserved in the first place. Or, you’ll hyperfocus on any instances where respect wasn’t given and conclude that respect isn’t present at all. 

Same thing for people who are secretly driven by a desire for love and connection. The increasing levels of power and admiration that you attain will feel like they’re getting you closer to the love and connection that you’re looking for. But you’ll be terrified to make any decisions that might threaten the power and admiration you have, because it will take away the prospect of “love” that you’re looking for. You’ll feel increasingly isolated and cynical as people get closer to you for the sake of proximity to power rather than because they actually like you.

Usually, in both cases you don’t recognize what’s going on; you just keep doubling down. Sometimes this works very well from a purely economic perspective—billion dollar businesses have been built this way. 

But it’s usually dysfunctional, and empty-feeling. Respect addicts are constantly pushing people away who they feel have slighted them and trying to climb hierarchies without thinking much about why or whether it’s actually what they want. Love addicts are constantly afraid of becoming doormats to the people around them, and are terrified of interpersonal conflicts that might threaten the businesses they want to build.

When the startup achieves the goal and exits, they’re both left with existential distress and despair, which can only be filled by getting back on the merry-go-round. 

.   .   .

Let me talk about about my own particular brand of fucked-upness on this subject. I think I have a weird, multi-colored, entangled version of both of these pathologies. I’ve come to see that I pursued startups in order to win respect, which I thought would win me love and connection. It’s a classic revenge of the nerds story:

In middle school, the kids I was around always thought I was smart. But I also felt like no one really liked me that much. I was constantly fading into the background. When something funny happened, no one turned to catch my eye. Plans were always made to hang out that didn’t involve me—that kind of thing.

So at some point I concluded that I would stop trying to be cool in the normal sense, learn how to program, get extremely rich and famous, and all of the people who ignored me in middle school would eventually want to come and hang out with me at my mansion. 

It turns out this did win me respect. But then I lost the respect and started having panic attacks. 

.   .   .

The thing about my subconscious desire for respect is that it didn’t seem to me like I wanted respect. In fact, I consciously told myself often that I “didn’t care what anyone else thought.” 

But I also found myself driving as hard as possible to succeed at any cost so that everyone would eventually have to pay attention to me.

I first felt my sense of respect from the world increasing in college. I started building cool software products that were working, and separately got minorly internet famous. A YC company called 42Floors publicly offered me a job in a blog post that went viral and got covered in lots of news outlets.

I remember one night in particular after that happened I had this almost disembodied experience of feeling like there was now this “Dan Shipper” out there that people knew of—who they thought was awesome—but who was manifestly different from the Dan I knew myself to be.