Highs and Lows of Entrepreneurship

“It’s one of those days again. The days that hit hard. The days you question everything. When nothing, everything, and the entire range of possibilities in between all seem completely plausible.” - Every startup founder, every now and then

Whether you succeed or fail at building a successful business, you are sure to experience such highs and lows from time to time. I think that’s what entrepreneurship is ultimately about. You have to learn to surf through the highs and lows without drowning.

Perhaps the highs and lows are both necessary. The highs give you the optimism that keeps you going, and the lows provide the caution necessary to avoid becoming delusional and doing crazy things. Cautious optimism is probably the key to long-term success (if success can be defined as your business not dying).

It doesn’t matter what stage a company is at, no founder is really “happy". Because the founder, by necessity, is living in an imagined future. Founders are a delusional bunch that extend the current trajectory of something (technology, markets, culture, science, etc.) and make it their purpose to chase the possibilities they see and bring them to life, often against all odds (most startups fail after all). And it’s this hunting for remote possibilities that is the source of all their excitement and all their sorrow. Because it is always a possibility, never a certainty. Always seemingly within reach, yet just outside their grasp. This is the thrill they seek, predicting the future with very real skin in the game.

As a founder, you quickly realize that the task at hand is so big it’s going to take everything you’ve got, and some more: hundreds or thousands of people and millions, possibly billions of dollars. To think yourself capable of something like that, without ever having done anything of the sort before has to be a form of madness. That successful founders are often eccentric is not surprising.

On one hand, you see the possibility, and you’re willing to give everything to make it happen. On the other hand, however, when you dive into it, you also see the risks: things that you never knew/thought about, or wishfully believed don’t exist, or didn’t realize you’d have to do, or didn’t expect the world will make happen. Once you take these risks into consideration, the “possibility” you felt so excited about seems more impossible than possible, or at the very least, one hell of a long shot. That’s when the fear hits and you sink into the lows.

One might think it’s external financial losses that hit entrepreneurs the hardest, but I don’t think that’s true. Financial losses are arbitrary and irrelevant as long as the dream is still alive, and you can still keep going. It’s the death of the dream, either because you realize the possibility is not going to come to life, or that you don’t have the time, resources, or ability to bring it to life, that you’re truly at your lowest.

The latter is far more severe than the former. When something is a certain impossibility, you can accept it and move on: the market changed, regulations changed, it’s against the laws of physics, or some new information has come to light which changes everything. What can you do about that? Nothing. It’s time to go get some rest and chase another possibility to entertain yourself for a few more years.

But the realization that what you’re chasing isn’t impossible, but you don’t have what it takes to bring it to life hits you hardest and takes a toll, mentally, physically, emotionally, psychologically, and in all the other possible ways. Because it’s reality telling you: “You’re not good enough to do this,” which, when taken personally, translates to “I’m not enough,” period.

It’s untrue, it’s unfair, but it feels just as real as the ground beneath your feet. True or not, it has the power to destroy you. And that’s possibly the real hurdle to overcome. To see it as it is, to not take it personally, and not let it crush your spirit, to accept it as yet another fact of nature, and to simply & matter-of-factly do what needs to be done: level up.

It shouldn’t be a surprise that you’re not good enough for the job. In fact, it’s the most likely outcome. As a founder, you put things out into the world hoping they will take off, and repeatedly get kicked in the face by reality. So you slowly learn to see everything objectively, except yourself. Seeing your insufficiency exposed is the hardest pill to swallow. But you have to swallow it, what else can you do?

The final step in becoming an entrepreneur is to step outside your bodymind, and take a good look at yourself: the system building the system, objectively. See all your flaws and shortcomings and tendencies and fears and apprehensions. The purpose is not to necessarily “fix” them all. You can’t get rid of them all, and some of them are desirable, or even necessary for success, for they make you who you are. But being aware of the truth, and accepting your reality as it is is a precondition for progress.

God, grant me the serenity to accept the things I cannot change, the courage to change the things I can, and the wisdom to know the difference.