1. Entrepreneurship is hard because it requires someone with a strong command of reason, who is at the same time thoroughly unreasonable

You have to be smart to be an entrepreneur, obviously. Modern businesses are complex, and you have to be able to reason effectively if you’re even going to understand how they function. But having a strong intellect is only half the equation. You also have to be able to let go of reason when needed. You have to see that reason is only one way of looking at things, and not a very popular one honestly.

If you decide to start a business, a lot of people will tell you (explicitly or otherwise) to “be reasonable.” To not take such an unnecessary risk, to not go so far outside the norm. It’s a fair piece of advice. But starting a business is inherently not reasonable. It’s never the “common sense” thing to do. It’s not reasonable to think you can create an entire organization from nothing and change the direction of an industry. No “reasonable” person would think that they can get lots of other people to believe in their vision, and invest their time and resources in making it real.

Entrepreneurship doesn’t naturally follow from a logical deductive process. If it did, someone would have already followed that process and started that business. You have to use reason as one of many tools, without letting it use you.

2. Entrepreneurship is hard because it requires an abundance mindset toward the environment, and at the same time, a scarcity mindset toward the business

Successfully starting a business requires an abundance mindset toward the external world. You have to believe, at some level, that opportunities for success are plentiful, or at least available for those who work hard. You have to look at the market and see fruits waiting to be picked. Otherwise it simply wouldn’t be worth the risk.

But at the same time, you have to have a scrappy, survivor-like mentality toward the business itself. You can’t treat your money, time, or mental bandwidth as “abundant” if you’re going to ration and spend them carefully. You have to jealously guard every resource you have at your disposal, because every one represents a little bit of precious runway.

The challenge is knowing when a situation calls for an abundance mentality, and when it requires a scarcity mindset. It’s easy to get stuck in one mode, and not realize when the situation changes and a different approach is needed. Neither mode is inherently better. Each one is a tool that you wield when it’s most effective.

3. Entrepreneurship is hard because it requires extreme vigilance of what competitors are doing, without being too influenced by them

You have to pay some attention to your competitors. If only because their decisions and actions yield useful information about what’s happening in the market. But you can’t be too focused on what competitors are doing, because then all your actions will be only re-actions. Too little, too late.

You need to have a kind of peripheral vision toward your competitors. Like explorers through a shared terrain, who you can borrow from and draft off of, remembering that ultimately you are not looking for exactly the same thing. You need to keep your competitiveness in reserve for when it’s useful, without letting it take on a vindictive life of its own.

4. Entrepreneurship is hard because you have no idea what you’re doing, but at the same time know exactly what you’re doing

Entrepreneurship is fundamentally open-ended. You are always working on some kind of frontier: the frontier of ideas, of what’s “normal,” of what customers are willing to accept. Which means that it can never be fully planned in advance. You need plans, of course. You also need to be fully committed to them if they’re going to teach you anything.

But at the back of your mind, in a private place you may not always show to the people you work with, you have to have some doubts. Like a “doubt room” in the basement of your house, you should occasionally spend some time there and let those doubts have their say. Because if you don’t, they’ll grow and fester and eventually explode as a full-blown crisis of faith.

Holding both total confidence and deep doubt in your mind at once requires something quite similar to self-delusion. There has to be some separation between them if you’re going to stay sane, but it should be more like a foldable partition that you reserve for parties, when you let it all hang out a little.

5. Entrepreneurship is hard because it requires a willingness to go far out of balance, without completely losing control

I don’t know of any way to build a business while staying perfectly in balance at all times. Habits and routines are great, but when that one opportunity you’ve been waiting months for comes knocking, you drop everything and you run with it. And on the long path to building a profitable business, such opportunities will appear almost weekly.

You have to build the capability of going out of balance when needed. To lean in to the turn like a motorcycle racer. This sometimes requires postponing or “stretching” everything from your bodily needs to your relationships to your personal finances to your goals. Not that you have to blindingly sacrifice these things at all times, but they have to be at least a little fluid.

But just as importantly, you have to know how to bring these things back into balance once the opportunity (or crisis) is over. To recover, to heal, to build those reserves back up to a state of readiness. Otherwise when the next one hits, you won’t have any slack in your system. You’ll be brittle and frail.

6. Entrepreneurship is hard because it requires being rigid where others are flexible, and flexible where others are rigid

Most people are naturally rigid in some areas, and flexible in others. They might be open-minded when it comes to their choice of food, but rigid when it comes to their religion. Mostly these come as defaults, as part of their upbringing and belief system.

But as an entrepreneur, you have to decide where you’re going to be rigid and where you’re going to be flexible. You have to approach your market with a set of beliefs that in some way violate or contradict or undermine the existing beliefs in your market. This naturally means that you insist, you take a firm stand, on areas that incumbent companies may let slide. Maybe you’re in payroll processing and customer service isn’t taken very seriously – it’s “flexible.” Taking a strong stand on that might ruffle all kinds of feathers.

But you also have to sometimes be flexible where others are rigid. Maybe you’re in legal services and you realize that educational pedigree is no longer as important as it used to be, and you relax your hiring standards. This also might encounter resistance as you threaten people’s pride! To take these stances you have to have a center and the center must hold. There has to be an immoveable place of conviction at the center of your being, that is not swayed by the opinions of others.

7. Entrepreneurship is hard because you have to not believe in tradeoffs, yet be constantly making them

Entrepreneurs have a skeptical eye toward supposed “tradeoffs”: statements that follow the format “To have more of X, you have to have less of Y.” That’s because every tradeoff is based on a long series of assumptions. And if just one of those assumptions changes, the tradeoff can collapse like a house of cards.

The auto manufacturing industry for decades was based on the assumption that it took many hours to change the “dies” of a machine in the factory (such as changing a drilling tool to a shaping tool). The entire industry was built around that assumption: from the way workers’ shifts were scheduled, to the way factory floors were laid out, to the lower pricing for larger batches of products. Instead of optimizing around this constraint, Toyota attacked it: they systematically lowered the time needed to change machine dies until it was less than 10 minutes. In doing so, they revolutionized the industry.

You can’t take tradeoffs too seriously, yet as an entrepreneur you also have to constantly make them. You have to pick your battles – perhaps you’re reinventing data science visualization, but that means you might need to conform to conventional accounting practices in the meantime. The energy required to destroy an assumption is in limited supply…for now.

8. Entrepreneurship is hard because it requires caring deeply what others think about your product, while not caring at all what they think about you

There is a certain egolessness demanded of entrepreneurs. You simply can’t afford to make it about you all the time. You’re not that important. If you insist on being offended all the time, you are inserting yourself into the feedback loop between your users and your product. You are distorting the flow of learning to serve your own purposes.

And yet, at the same time, you can’t completely discount and write off what everyone says. You have to be obsessed, in fact, with what they say about your product. To hook your reward centers deep into their experience of the product, so that you feel their pain as your pain and their joy as your joy. It’s an extreme form of empathy I think, directed and focused like a laser on the intersection between what they need and what you can provide.

9. Entrepreneurship is hard because it requires you to be highly ambitious, yet not preoccupied with the inevitable failures it brings

You obviously have to be highly ambitious to be an entrepreneur. You have to have a vision big enough to justify its terrible cost.

But the more ambitious you are, the bigger the chasm you’re going to have to cross. The bigger your vision, the more time you’re going to have to spend in not-that-vision. This is totally obvious and yet paradoxical: the more you want to be right, the more you’re going to have to get used to being wrong. The more successful you want to be, the more you’re going to have to get used to being unsuccessful. To get good at error-correction, you need to become intimately familiar with error.

All this means that you’re going to have a lot of failures. You must learn how to reframe those failures as valuable lessons, which sometimes feels like bending an iron rod into an origami flower. But it can be done, because the meaning of those failures is completely up to you. The failures are real, but what they are telling you is not real, it’s made up.

10. Entrepreneurship is hard because you have to always do what you say you’re going to do, and also consistently say you’ll do impossible things

The edifice of entrepreneurship rests on a foundation of integrity. You absolutely have to be the very embodiment of your word, because at the end of the day that is all you have. Your word has to be so powerful that it has its own agency: you said it, and thus it will happen. Your word can bend reality to its will, and to build the business you envision, it must.

But simultaneously, you have to constantly be promising impossible things. That your business will grow by a certain percentage, that the market will expand by so many points, that such and such contract will be signed. These events are not within the realm of what you can achieve by yourself. To be interesting, the reach of your promises has to exceed their grasp.

And this brings us back to the first paradox. Human agency does not quite exist within the domain of reason. It defies the cold logic of causality. It uses logic to explain and to argue, but if you get to the very source of it, there’s no fundamental reason that anything it wants should happen.

Except for one: because you said so.


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