The Worst Reasons For Becoming An Entrepreneur.
They exist. Let’s talk about them.
So I never thought this would happen when I became an entrepreneur: You hear a lot of how-I-became-an-entrepreneur stories.
I know, how did I not know that would happen?
Call it naivete.
But it’s true: Most people who become entrepreneurs become them for very specific reasons. Very few people realize when they’re a kid that they want to grow up to run their own business.
Maybe Warren Buffet did. But that’s about it.
Most of these stories are heartwarming, or at least innocuous. People start businesses so they can be at home with their children. They want to have more control over their income. They want to travel.
But then there are people who become entrepreneurs for terrible reasons.
They’re usually pretty veiled. They’ll say something like, “Oh, the corporate world was tying me down” or “I thought I could do something better with my life.”
Uh huh. Just one sentence describes why you decided to take on one of the hardest ways to make money?
There’s always more to that story.
And it usually isn’t pretty.
Here’s what people may not be telling you about their grand adventure toward solo work:
They’re terrible to work with and/or unteachable.
One of the most successful entrepreneurs/worst human beings I ever knew because an entrepreneur for one reason: He was a terrible worker.
Let’s call him Jerry (for obvious reasons).
Jerry worked on and off at various companies. Every time, at some point in working there, he’d get into an argument with his boss and quit.
Cute and rebellious right? Fuck no.
This ultimately led to he and his partner upheaving their lives every few years to try out new careers. Jerry would try to keep it together, but it would eventually happen again: Screaming match with the boss, a know-it-all attitude, then leaving in a huff.
Jerry eventually became an entrepreneur. A fairly successful one, too.
But starting an entrepreneurial career because you suck at regular work isn’t a good reason to be an entrepreneur. You should be at least passable at “regular work.” Bonus points if you’re good at it.
Being an entrepreneur should call out to you like a siren song. You should want that lifestyle more than anything. It shouldn’t be your Last Chance Texaco.
Traditional work requires sacrifices they don’t like.
This is something that I think a lot of people relate to more than they think.
The fact is, working a “regular” job requires so much more side work than most people take into account:
You have to commute.
You have to make small talk.
You have to wear nice clothes some of the time (or strategically “casual” clothes).
You have to occasionally give speeches or presentations.
You often have to go to social events that suck.
You have to get approval over decisions such as taking a vacation or calling in sick.
Having a “regular” job requires more time and less control than most people realize (until it’s too late). A good chunk of people become entrepreneurs because they picture a business-owning life as relaxing 24/7.
Hell, I became an entrepreneur after working with people who didn’t understand that I was commuting three hours every day to work for them. I wanted to control my own schedule.
But here’s the secret: Having no schedule means you have to set your own schedule. And enforce it.
Let me tell you: There’s almost nothing harder about being an entrepreneur than enforcing your own schedule. You have to make yourself work. Even if it sucks. Even if the assignment sucks. Even if the client sucks. Even if you suck.
Even though I don’t have stupid small talk to deal with, I have to pitch myself regularly to people.
No office parties means I have to work harder to make sure I’m getting adequate social time (with friends and work colleagues).
No dress code means I have to work to maintain a good appearance and not let myself devolve into laziness just because I have no office.
Running your own business doesn’t mean you have no problems. It means you have different problems. Work is work is work.
They don’t think traditional work will ever change to suit them.
This is the saddest one, as far as I’m concerned.
Over and over again, I see people dropping out of the traditional workplace because they don’t see a future that includes every one of their dreams. Rather than trying to change it, they leave.
At the very beginning of my career, I was extremely lucky to work with some very lovely and successful mommy bloggers. People write off the women behind these blogs—they take pictures of their families and write about home decor for a living. Occasionally they’ll focus on creating food for a specialized diet. How hard can that be?
Extremely hard. Most of the women behind these blogs are expats from the corporate world, harnessing their skills and grit to work for themselves. Pregnancy or eating healthy food that wouldn’t make them sick just didn’t work with their traditional corporate jobs.
So they left. And they took their marketable skills with them.
I’m not surprised at all when I hear about bloggers or Etsy entrepreneurs making thousands of dollars. Chances are some corporation didn’t have what they needed to be happy working there. And frankly, they blew their chance to change. So, silently and deliberately, these brilliant people got the hell out.
For further reading on this subject, particularly those who don’t understand the awesomeness of mommy bloggers, I recommend Homeward Bound by Emily Matchar.
They’re too anxious/sick/whatever for traditional work.
This is where people may start to turn on me.
A long time ago, I asked a question in a private Facebook group: “People who work from home, do you identify as having a mental illness or a condition that makes ‘conventional’ work difficult?”
There was about a 50–50 rate between yeses and nos. But for the people who answered yes, holy shit.
There are a lot of people out there with terrible physical and mental disorders working and creating a lot of stuff out there. People with disorders like bipolar, agoraphobia, Stiff Person Syndrome, and so many hell-on-earth conditions are out there working and kicking ass. I personally have anxiety and PMDD.
This isn’t a rag on people who opt out of conventional jobs for the sake of health. This is an indictment on conventional work itself: Do they know who they’re missing out on?
By not addressing mental and physical health concerns quickly, or even allowing for alternative work styles, they are missing out on so much genius. So much drive. So much fuck-you-I’m-getting-it-done.
It’s not a terrible thing for entrepreneurs to opt out of conventional work for their own health.
But come 2028? It might be a terrible thing for conventional work.
They’d rather fail alone than succeed under orders.
This is the “high note” point that I’m going to end on.
At least half of the entrepreneurs reading this will probably agree to this reason for themselves, and gladly.
(Whatever keeps people from lighting torches.)
Entrepreneurs, by and large, like to be decisive. It’s a high. I did this, so THIS happens. I made an impact on the world!
This is the opposite of what it feels like to work a conventional job. Things have to be approved. Clout must be observed and respected. Procedure and decorum has to be followed.
Now, this is in place so people don’t just ruin a company with a single decision. It’s a good thing, in principle!
But for some of us, that just doesn’t work fast enough.
Some of us are addicted to the high of saying something and making it happen immediately. Even if it sucks. Even if it fails.
This urge isn’t glamourous. It sometimes makes you feel like a child, impatient and unable to settle down and let things happen. You feel “less than,” like you need to learn how to be a mature adult.
You get into a conventional job again.
Your little entrepreneurial experiment is over. You’re ready to settle down.
You want to make things happen.
Why aren’t they happening faster?
At the very least, why can’t you see the steps and reasons why things aren’t working faster?
And who is this person, telling you to do things? They just refused your initiative!
They want you to be innovative but also do what they say.
That’s when the inner voice inside you starts to scream: Who the hell do you think you are?
Childish? Maybe so.
But sometimes people become entrepreneurs for the same reason some people become compulsive skydivers: They just can’t help themselves.