Want to be an entrepreneur? First, ask yourself these five questions

Brooke Allen
4 min readJul 7, 2015


I’m fairly entrepreneurial, having started a few businesses that have made me well off enough that I can now pursue my personal mission, which is to be of meaningful help to my people without expectation of financial reward.

Who are “my people?”

Over-educated Westerners.

My people know a lot about a lot, but often little about themselves. For nearly a decade I’ve been studying what it takes to be of good character, what constitutes a robust personal philosophy, and how to have a meaningful life. I’ve come up with 54 questions that you can ask yourself and I’ve put them all on Q54Club.org. Here are five that are particularly important if you think you want to be an entrepreneur (and even if you don’t).

1. Who am I?

Many people who say they want to be entrepreneurs really just want to be self-employed because they chafe at having a boss. This is a bad reason. Start your own business and everyone will become your boss. If you’re lucky then prospects, customers, employees, investors, regulators, vendors, lawyers, banks, and markets will all tell you what to do. And if you are unlucky they will just let you fail.

These wannabe entrepreneurs have a choice about what they become and I suggest they carefully consider their alternatives because they will be in competition with the people I call “true entrepreneurs” who have no choice.

Does the world have a problem you cannot stand to see go unfixed? Do you have ridiculous vision that you cannot get out of your head? Are you obsessed with a vision nobody sees or an idea nobody gets? Congratulations, you are either crazy or an entrepreneur, and the only difference I’ve found between the two is success. So you have no choice other than to get the thing in your head out into the world or people will think you are nuts. Of course they will think you are crazy anyway — until you succeed — at which time they will say they want to be just like you, and they will start reading everything they can find on “how to be an entrepreneur.”

2. Who is important?

A Nobel Laureate in physics once told me that if you want to be really good at, say, physics, then you have to go to bed thinking about physics and wake up thinking about physics and you cannot be thinking about your family. The problems and people you think about the most are likely to benefit the most from your thinking. And your products, processes, employees, customers, and investors all need high priority. Some people you care about might just have to forgive you for not thinking about them as much as they wish you did.

3. What do I need to know?

I took a class on entrepreneurship near the end of my MBA. The professor started by saying that school is a great place to be if you cannot think of anything else to do, and it is hard to attract great students because they are doing better things than attending his class. Had it been my first class, I could have saved a lot of time and money because most of what I learned in business school was either a definition, self-evident, or false.

You need to know just enough to get started. Everything else you can learn just-in-time on a need-to-know basis. Getting a firm grip on everything before you start will only overwhelm you, so don’t do it.

4) What do I want to do?

A venture capitalist told me he will not invest in anyone until he gets a straight and verifiable answer to, “What (not who) do you love?” My father told me, “It is easier to make money doing what makes you happy than to buy happiness with the money you are paid for doing what makes you miserable.” If there is something you will do only if rewarded then do something else. The best results come from love of the work, not love of the results. Grokking this does not make you an entrepreneur, but not grokking it makes you not one.

5. Why do I exist?

Purpose trumps profession. If you must become an entrepreneur to fulfill your life’s purpose then so be it. But if being an entrepreneur would be a distraction from your purpose then be something else instead.

It all comes down to who you are because personality trumps profession too. I know a student who was considering studying engineering. I asked an experienced engineer if he would mind if the student shadowed him, and he asked, “Is the kid an engineer?” I said he wasn’t yet because he had never had an engineering course.

The man replied, “I didn’t ask that. Engineer is a personality type. When he got a toy did he take it apart or did he play with it?”

“He played with it.”

“Then he is not an engineer, so why would he waste his time?”

Of course, he is right. And if “engineer” is a personality type, then “entrepreneur” is a disorder. Too many people are unhappy and uninspired doctors, lawyers, and engineers because they invested too much in becoming those things before discovering it isn’t who they are. You can get stuck doing those other things for a lifetime, but the good news is that if you try to be an entrepreneur and you aren’t then you won’t be at it for long.

You can find Brooke at brookeallen.net.

Originally published at qz.com on November 4, 2013.



Brooke Allen

I come up with ideas and try to express them with words, code, and deeds.