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You Absolutely Positively Should Not Start a Business

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It’s hard. It takes a ton of sacrifice. You’ll probably get fat, broke, depressed, burnt out, divorced, or all of the above. You should absolutely positively not start a business… unless you can do the following:

1. Envision yourself doing nothing other than being a founder

When I was considering starting my first business in 2008, I was told that if I could see myself being happy doing anything else, I should do that instead. Having disregarded that advice for a seat on the five-year startup rollercoaster, I can’t say I disagree with that wisdom. If you want to get rich, there are easier ways to make a buck. If you want to be challenged, you can do it in healthier ways. If you want a flexible job, go be a freelancer. It takes a unique person to be happy being a founder.

But for those people who are truly built for it, entrepreneurship can be the most gratifying and rewarding experience imaginable.

2. Live with the tradeoffs

I often tell my friends that the best parts about founding a company are also the worst parts.

The Good: You get to work on something you’re passionate about. Every day you wake up feeling energized to kick some ass.
The Bad:  When you’re passionate about something, it’s easy to get obsessed. And when your livelihood is an obsession, the other pieces of your life pie tend to get eaten up. It’s not just an issue of time; it’s also mindshare. Unless you’re very good about compartmentalizing (harder than it sounds), you’ll find yourself constantly thinking about your startup. Which means you may be “present” with your friends or your family, but in reality you’re not really “there.”

The Good: You work autonomously. You are a free person.  You can walk barefoot in the office. You don’t have a boss (unless you raise money, and then your VCs are kind of your boss).
The Bad: Being autonomous means you have to figure things out yourself. Not only do you have to learn how to prioritize what’s important, you have to be an expert at doing those activities. For first-time entrepreneurs, that means you’re learning the hard way: by hitting your head against a wall until something shakes loose. It’s not an efficient way to learn. And it’s frustrating not having someone to turn to. Entrepreneurship is a lonely road.

The Good: Your successes are your successes. You get credit for your work. There’s a sensible effort to reward ratio.
The Bad: Your failures are your failures. You’re the boss, the big cheese, which means the buck stops with you. If your idea goes down in flames, you can really only blame yourself. And for high-achievers, that can be devastating, depressing, and sometimes downright unlivable.

If you think long and hard and believe you can live with these tradeoffs, then you’re probably in good shape. But remember that it’s often hard to know how you’re going to feel about something until you try it.

3. Manage your own psychology

Most people don’t have to be “on” 24/7. They have some off-time where they can hide from the limelight, be weak, be vulnerable, be imperfect. But as a startup founder, you don’t have that luxury. Every second of the day, whether you like it or not, you are sending a signal and being evaluated. Which means that outwardly, you should convey confidence 24/7. If you happen to be on a rocketship, it’s easy to play this game because everything is going awesome. You’re the hot deal in town, investors are clamoring to get in, prospective hires are lined up at the door, and your employees are happy. But chances are, your situation is more difficult. You have problems. And as the founder, it’s your job to focus on problems so you can fix them.

This creates chaos in the brain. Inwardly, you are entrenched in all the things that are going wrong. You feel doubt, insecurity, and fear. But outwardly, you are expressing the things that are going right. You emote positivity, optimism, and confidence. You are reassuring your employees even though they’re worried about the exact same issues that keep you up at night. This is a maddening, complex process to manage, and may be the most difficult founder skill to master.

The best founders are experts at managing their own psychology and finding a mode of self-expression that conveys positivity while being authentic.

If you think you can hack these three conditions, then congratulations! You are bizarre, crazy, and unique enough to be a startup founder. Go start the next big idea and change the world. If this doesn’t sound like you, my advice is to keep your day job. You’ll live longer, healthier, and happier.

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