The Weight of Trying

A friend and I just discussed what makes great entrepreneurs successful. We tried to dig into the not-so-obvious bits. Of course, there is a required baseline of intelligence, subject matter expertise, business acumen, leadership, and more. All of those things are helpful. But all of those feel like they're necessary but not sufficient.

It seems to me that perhaps the most important component is emotional. Interestingly, many people have talked about this, but they talk about it as something like resilience or emotional management. And while it's true that being resilient is important, it's missing something. The ability to manage heavy emotions is essential, but even the strongest person can't shoulder heavy burdens forever. The most successful people are those that somehow set up their expectations in such a way that most things don't feel heavy to begin with.

Let's use Elon Musk as an example. He's not somebody that I particularly like (or at least I don't love his public persona), but he is an extreme and obvious example of entrepreneurial success. There are, undoubtedly, myriad factors that make up Elon's success. People often talk about his vision. They talk about how much he cares about the projects that he's working on and his incredible work ethic. All of that is likely true. But one of his most underdiscussed skills is his ability to shitpost.

Elon Musk somehow aims his ambition (and maybe his opinion of himself) so high that he can look at a cripplingly large problem and think "it's not that deep." While I don't know this for sure, I imagine him shitposting his way through business the way he does on X. That is to say, with incredibly little regard for the repercussions of getting it wrong. That's not to say he doesn't want to be right, only that he is unbothered by the prospect of being wrong. In this way, he seems able to press onward and make incredible progress on things most are too afraid to start.

This is, of course, still a form of emotional management. But it's not reactive emotional management. It's like management of emotional starting conditions. It's the ability to treat everything lightly from the get-go. Some of us feel like we have to have an incredible passion for a problem set and a correct solution in mind for it to be worth speaking about, working on, or getting outside investment in. But the best entrepreneurs simply assume that their ideas, good or bad, are worth trying. And they go raise the funds to try them. And if they don't work, they try the next one.

Of course, you need to take some of this with a grain of salt. I'm not suggesting that nothing has stakes, but I am suggesting that if you feel like the stakes are so high that you never play, what's the point? The people that play are the people that believe the stakes are low enough to make playing affordable and the payoff high enough to make playing worthwhile. A common failure mode is bringing our own emotional baggage into the price of entry, thus raising the stakes for ourselves for no real or objective reason, making it unsustainable to play more than a round or two.

I have founded, cofounded, or meaningfully participated in, more than a few companies throughout my career. Every one of those experiences has ground me down and burnt me out. I have regularly asked myself: Why do some of my colleagues seem less affected by this than I am? I have felt ashamed of burning out and wondered what they have that I don't. My conclusion? I place outsized emotional weight on my output and the venture's outcome. This reddit post sharing that some people use "hard work" to mean "work done over a significant duration of time" and not "work that causes actual pain and distress" is relevant. My brain certainly falls into the latter category. (Yes, the post makes this about autism vs neurotypicals but this is a problem seen in all types of humans.)

To put it simply, my relationship to work, productivity, and output was wrong from the start. Something about my inner state was adding to the load, layering a heavy emotional component on top of the work that doesn't improve outcomes, and in fact, likely makes them worse.

Failure is inevitable. Bad ideas are inevitable. Losing money is inevitable. Great entrepreneurs don't avoid these things. Great entrepreneurs just don't treat any of these things like the end of the world. They're the equivalent of swinging and missing in a baseball game. It's a bummer, but that one swing doesn't define that game, much less the player's season or career.

This is a rather unpolished take. What I'm describing is abstract and difficult to capture, but at its core it's about taking big swings without giving each swing so much emotional weight. Treating each swing like it's your only chance is like putting weights on the bat. It makes you worse at this current swing while also wearing you down so you can't take as many swings. I don't know how to put the weight down, but I'm figuring it out.