I’m Not An Entrepreneur (And You Might Not Be Either)

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Photo by Alex Kotliarskyi on Unsplash

I value a lot of things over money. I always have.

When I was four years old, I traded the contents of my piggy bank for a pile of gimp (you remember? the plastic string crap). If that’s not the tell-tale sign of a failed negotiation, I’m not sure what is. My parents were pissed.

Luckily, I’ve become a lot more savvy and entrepreneurial since I was four years old. I see opportunities for upside and am significantly more capable to capitalizing on them. It’s safe to say, I’m no longer trading in all my cash for the raw materials of a plastic bracelet.

But that doesn’t change the fact that this story tells you an important part of who I am.

In late 2017, I ignored this fact and decided I no longer wanted to work at a corporate job. I was unfulfilled and exhausted. So for the next 18 months, I took a detour down a long side-street called Entrepreneurship Blvd.

Like most people in my generation, I thought going out “on my own” would solve all of my biggest problems. And the truth is: it did solve a number of them, but it also created a bunch of new problems.

In this process, I realized our collective view of entrepreneurship is convoluted at best, delusional at worst. Most people, like myself, are focused on the ends, not the means.

The cultural conversation shows we shouldn’t blame people like me for thinking this way. The benefits of working for a large conglomerate are evaporating. Companies are treating their employees as replaceable, under-employing and underpaying them. Pensions are a relic of the past and, since 2008, 401Ks don’t even seem reliable.

The labor economy is evolving. There is growing distrust in big business. Our lives are filled with incessant distraction, what psychologist Meg Jay has deemed “the opiate of the masses.”

Plus, the money-making potential in the digital world — from drop-shipping scooters to building apps — seems endless. And Mark Zuckerberg’s story made every kid with a computer thing they can be worth a billion dollars by 23.

On the back of that, our culture has sold this dream — of traveling the world, taking meetings, closing deals by the pool, and throwing cash. Without having to answer to anyone.

When I set out on my own, it was for a few reasons. First, I wanted to in the most idealistic and cliché way possible — “have an impact.” Second, I was tired of someone demanding that I show up at the same place every day at the same time and do precisely the same thing over and over.

Soon after making the leap, I found myself in a client services role, where I was just answering requests all the time. I was trading time for money in a gig fashion, not really building something that I could scale or build any equity in over the long-term.

Still, I worked everyday just like those Instagram entrepreneurs. And when I wasn’t working, I was crippled by guilt.

I was failing. Not because I wasn’t competent enough, not because I wasn’t pushing hard enough, but because I was doing something counter to the very fabric of my being.

When I was honest with myself, I knew I missed working with a team, managing people. And I’d swung the pendulum too far in the opposite direction.

That’s when I realized, I wasn’t an entrepreneur.

Or more accurately, I didn’t want to be one.

I’ve never heard anyone admit that out loud. It’s an uncool thing to say, especially considering how sexy entrepreneurship is today. How much we respect the characters in Silicon Valley and Hollywood.

But I think it’s an important part of the cultural discourse that’s missing.

And I guess that’s the reason for this article.

To share the things I’ve learned on the path to realizing I don’t want to be an entrepreneur in hopes that it might help you come to a similar realization if you’re in need of it:

The goal isn’t to be an entrepreneur, but rather to optimize for long-term happiness.

Whatever you choose to do with your life, try and choose what’s going to make you happy over the long-term— not just on the surface, but at a very deep level. And think critically about what this might look like for you.

Maybe it’s building a business or working in a business. Maybe it’s freelance writing, starting a non-profit, or opening your own farm in northern New Hampshire. Maybe it’s driving Uber, becoming a doctor, getting into politics.

Just work at being happy. Because when you’re happy, you’re a better and more effective parent, spouse, sibling, human. You can have way more impact on the world at-large if you’re in a good state of mind.

The problem is that most of us don’t really know what will make us happy over the long-term. In fact, that’s the entire punchline of Daniel Gilbert’s book, Stumbling on Happiness (or at least what I got out of it).

We don’t know what will make us happy in the future because we can’t comprehend the first, second, and third order consequences of our decisions past, present, or future.

So, when making big life decisions about where you want to live, who you want to marry, what you want to do, it’s important to ask yourself why. Over and over again until you get a real answer.

For me, entrepreneurship was the only path I could see to time and location freedom. It’s what I felt I needed. That said, I don’t think that’s a good reason to do something.

The cold, hard truth of the matter is:

You can’t build a life based solely on what you don’t want.

You have to have a conception of what you do want. And if you don’t know? Then you need to experiment, play around, try out a bunch of different things.

Choosing to be an entrepreneur because you don’t want a boss doesn’t make any sense. Choosing to be an entrepreneur because you’ve identified a problem worth solving, a passion worth investing in — okay, now we’re getting somewhere.

When it comes to anything in life, but especially happiness, plan to keep optimizing as you go.

As we’ve established, happiness is illusive. We really don’t know what it takes to be happy; that’s why it’s important not to be so stagnant in your thinking. Be open to changing course, taking new paths.

I thought I’d be insanely happy working for myself. And while I was happier, I wasn’t happy. I was still missing really important degrees of purpose, mission, connection, and passion in my life.

Imagine if I kept investing in that losing strategy for another 18 months. Where would I be?

A friend of mine recently shared with me that he likes to think about being happy as two-step process:

(a) Know what makes you happy.

(b) Be mindful about it.

In other words, make a list of all the things in life that will make you happy (we’ll call this your “Happiness List”). These could be simple things — like long hugs, giggling, and playing with your kids. They could also be big things — like saving someone’s life, writing books, or donating large sums of money.

Every day, your job is simply to notice whether you’re doing enough of the things that make you happy.

Further, to pay attention to when a BIG decision you’re making is mutually exclusive with something on your Happiness List. For example, if working out in the morning is crucial for your overall well-being, you probably shouldn’t choose a job where you have to be at the office at 5:30am.

Your Happiness List will change over time. It’ll ebb and flow; the key is to just stay aware and keep moving in the direction towards what matters to you most.

When you’re choosing a career, focus on the means and the process, not just the ends.

Most people like the idea of entrepreneurship. You make your own hours, work from wherever you want, and (theoretically) call all the shots. It sounds like a dream never to have to answer to someone else, wear a suit, or show up at an office everyday.

There is something so freeing about the idea of firing your boss and going out on your own. But the thing is, when you’re in that mindset, you’re only focused on the benefits of entrepreneurship, not the difficulties that accompany it.

And you have to really ask yourself — with a full view on everything entrepreneurship entails — is this the game I want to play?

Because that’s what it is. It’s a game, with ups and downs, that you as the solo-operator and leader have to ride day-in and day-out.

That’s great if you’re up for it, if you get fired up off that kind of thing. But if you’re not, you may run straight back into a job you hate when you realize that you miss being part of an office community, having a consistent paycheck, and being told what to do.

That could have all been solved for if you thought more critically about what it was that you really wanted out of all of this and made a move closer to that.

In all decisions, prioritize growth and love over comfort.

Often the issue with working at a particular firm is just that you feel stagnated and disconnected. You don’t need to up and change everything, go out on your own, but instead you just need to rediscover what it feels like to learn and grow consistently, to connect over a deeper mission with people you like.

The thesis in Angela Duckworth’s globally-acclaimed book, Grit, is that a mix of passion and persistence — cultivated over time — is the key to realizing our wildest dreams and most audacious goals.

Whenever we are becoming more competent in a particular skillset or building stronger relationships with the people around us, there is the feeling of progress.

And that above nearly everything else is the pathway to higher levels of passion and happiness.

The ideas of who we should be are what f*ck us up most.

Whether it’s our parents in our ear, or the incessant chatter on our Instagram feeds, there’s a million different forces that influence who we think we should be, what we think we should do.

It’s easier to sit down at Thanksgiving dinner and tell your family that you’re applying to medical school than it is to mention that you’re planning to backpack through Europe for the next six months.

It’s easier to sit down at Friendsgiving and tell your friends all the crazy stories about the side business you’re starting than it is to talk about how much you love working at your 9 to 5.

What if — instead of listening to the opinions of others— you slowed down to the speed of knowledge and listened to what you really value?

It’s simple, isn’t it? Life would a hell of a lot better.

So, do yourself a BIG favor and stop measuring yourself against other people.

What will make you happy is not the same thing that will make your brother happy, your parents happy, your friends happy, your idols happy.

Just because someone else loves writing screenplays, slinging CDs, building businesses — doesn’t mean you will. Just because the picket fence and cul de sac made your parents happy — doesn’t mean it will make you happy.

There’s that famous Albert Einstein quote that comes to mind:

“Everybody is a genius. But if you judge a fish by its ability to climb a tree, it will live its whole life believing that it is stupid.”

If you put yourself in a situation that’s counter to who you are and what you are naturally interested in, you’re going to be miserable. That’s what makes entrepreneurship so compelling; it feels like it’s a pathway to aligning with your strengths.

The truth is — you might be a lot happier working as a COO at an established company in the city. Or as a journalist, a dog groomer, a lawyer in the suburbs. You might be a lot happier if you didn’t think you had to be an entrepreneur to earn some street cred.

No one has the right to judge you just because you choose to work for a company, choose to have a boss. Nor do they have the right to judge you for choosing the opposite.

At the end of the day, you’re trying to do the best you can with whatever skills, resources, and knowledge you have. And that’s what matters.

Find solace in knowing the world would be a better place if you just played to their strengths, invested in the collective good, did what made you happy.

Failure of imagination is the thing you are really fighting against.

Just because you’ve never liked a job doesn’t mean the only option is to go build something for yourself. That’s the easiest way out, but might not be the most effective.

It’s not “either/or.” It’s “yes and.”

You can be more creative, entrepreneurial, strategic, forward-thinking and work for someone else. You can have a lot of time and location freedom and work for a company.

The key is knowing what you really want, what’s important to you, and designing a life around that. Instead of trying to chase down the perks.

At all costs — I urge you to try and expand your imagination, dream bigger.

The Employee or Entrepreneur Dilemma is a false dichotomy. To believe you can only have freedom if you work for yourself, to believe you can only do something meaningful outside a company is false.

You could become a “linchpin” as Seth Godin calls it. This is the employee in a business that make sh*t happen. Linchpins are creative, strategic, forward-thinking.

You could take frequent sabbaticals from your office job to go off the grid and hike some of the world’s tallest mountains. You could be a corporate lawyer at Apple and a highly-decorated obstacle racer (cough, Amelia Boone). You could quit your job and commit to doing an Ironman in Antarctica (cough, Project Iceman).

Whether you’re an employee at a billion dollar business, an entrepreneur, a stay-at-home parent, or an athlete, the key in life is to think for yourself, think on your own two feet.

Create the world that you want to live in. Fight the inertia of an organizational bureaucracy, fight the pull towards complacency, and design your own non-traditional metrics of success.

There are infinite ways to be happy in this world, to make an impact. The best you can do is continue to think bigger, entertain more options, and continue to move in the direction that makes you feel most alive.

And remember: there is more than one archetype in every industry.

Every once in awhile, you meet a really happy lawyer. It kind of strikes you as odd, right? Lawyers are known for being these uptight, miserable rule followers. The industry has a reputation of rampant depression and alcoholism. So when you find someone that seems genuinely happy as an attorney, it can be off-putting (in the best of ways).

And that’s because this person has chosen a career path, a company, a mission that actually makes sense based on their skills, interests, and talents. They are intellectually stimulated, doing things they like doing.

This goes for every industry in the world. We have an idea of what it means to say “I’m a ____ and I work at ____.”

Even with entrepreneurs. We essentially put them in two camps: (1) the fast-talking GaryVee’s of the world, and (2) the f*ck-you-flip-flop-wearin’ Mark Zuckerbergs.

This kind of thinking lacks creativity; it makes us unable to consider the multitude of options of what we could be. Try to find people in your life that exhibit the opposite of stereotypes, that are wildly creative in their thinking about how to design their lives. Entrepreneurial accountants. Disciplined artists.

Usually, the reason these people are so freaking happy, is because they are just being themselves.

Whatever you choose to do, don’t hold yourself in contempt.

We all have different hopes, dreams, and aspirations. There’s nothing wrong if what you want in life is counter to what the people around you want. In fact, I salute you if you have the audacity to live it out.

Just own who you are and what you’re about.

Be viciously self-aware about what is needed in order for you to be happy over the long-term. Be unapologetic about what it takes.

Be adaptable and ready to change course when your strategies aren’t working.

Because, at the end of the day, if you can put your head on your pillow, happy with how the day turned out, you’ve won at life.

THE PUNCHLINE: Your desire to be an entrepreneur is probably just a means to some other end.

Think thoughtfully about the world you want to live in, what matters to you, and what role you want to play.

Instead of focusing on becoming an entrepreneur, build skills and relationships. Do amazing things. Think outside the box. Don’t be so caught up in needing the title of “entrepreneur” that you miss out on the valuable experiences that the rest of life has to offer.

Because here’s my confession. I wrote this entire article knowing that I will probably start a company at some point. I will continue building out plenty of passion projects. I plan to write many books.

I’m not just passively submitting to a life that was predefined, a track that was pre-laid. I’m not stuck in a mindset where I believe some big business is going to come in and save me.

I’ve just realized I like living in more of an artist/manager role. I love writing. I love coaching and working with people. I love thinking big about how to make things better. And I love optimizing processes.

And I’m still that little girl who would trade her entire piggy bank for some gimp if it made her friend happy. What a blessing and what a curse.

Better yet, today, I’m living the dream. I’m the first employee at a small talent management and business development company in Los Angeles; it’s lean and mean.

I work with people I love (not just like) and am working on projects that I think will have a resounding positive impact on the world over the long-term. I’m not the #1 in this ecosystem, not even #2, #3, or #4. I’d say I’m probably somewhere in the top ten.

And that’s more than fine with me.

Because I realized, I didn’t need to be #1. I just wanted to do something impactful with people I believed in.

And somehow, life intervened to show me the middle path.

Where I didn’t have to be miserable at a job or be a free-floating solo-entrepreneur.

I could be both.

I could be neither.

But more than anything else, I could be happy.

Thinking deeply about how to make myself and the world a little better | email: kate@onedayent.com

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