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Why Aren’t Entrepreneurs Happy? by Britt Reints


Pittsburgh is a hotbed for start-ups and self starters, and for the first time in my life I’m meeting a ton of people whose  job titles sound just as made up as mine. I’ve also been learning a lot about what makes entrepreneurs happy and unhappy.

Contrary to popular belief, working for yourself will not necessarily make you happy.

In fact, as Abe Taleb pointed out during his PIT talk earlier this month, it’s believed that entrepreneurs are more likely to be depressed than most people.

Yes, those people with uber perky twitter updates, extra exclamation points in their bios, and profile pictures of LIVING LIFE TO THE FULLEST! are extremely susceptible to depression.

How is that possible?

In my experience, many of the qualities that make someone a great entrepreneur also get in the way of happiness.

Entrepreneurs are forward thinkers. Happiness lives in the present.

People who start companies and make things wake up every day thinking about what will come next. They are fueled by forward motion. Having a project brings them joy and gives them a sense of purpose.

But… appreciating the present moment is an important part of being happy.

In the present is where you find peace, gratitude, and the sense of security that every human being requires. The future is an unknown; the present is something you can put your arms around and practice accepting.

Even forward thinkers need to spend time in the now.

I struggle with this balance. I live for the next great adventure, and I am most unhappy when I am waiting for something exciting to start. It’s easy for me to fall into the trap of, “I’ll be happy when…”

But when isn’t a guarantee. If I’m going to be happy, I have to work on being happy now – and the only way to do that is to pay attention to it

Entrepreneurs are optimists and positive thinkers. Happiness is found on the dark side.

When you’re selling yourself, as many entrepreneurs are, you have to put the very best version of yourself on display at all times. That means no kvetching on Facebook about your in-laws or moaning in meetings about your money woes.

But… if you deny yourself the right to unhappy feelings, they will permeate every aspect of your life until they can no longer be ignored.

Feelings demand to be felt. They insist on being acknowledged. They can only be stuffed or “reframed” for a limited time before they will explode all over your life in an act of rebellion.

Branding myself as a happiness advocate has definitely made it more difficult for me to feel unhappy. When I am fighting with my husband or pulling the covers up over my head instead of working, I feel like a fraud. This, “my life’s work is a lie!” mantra is a brand new tool my brain has come up with for avoiding feelings.

Everyone has unhappy feelings. Everyone. Even people who are passionate about happiness.

Entrepreneurs have to be able to say, “I’m afraid,” “I’m pissed off,” or “I’m sad and don’t know why.” And, most importantly, they have to find a safe place to express those feelings – somewhere they won’t be met with well-meaning attempts to fix or cheer up.

Entrepreneurs are doers. Happiness comes from being.

Entrepreneurs, like bitches, get shit done. They don’t just talk about quitting their jobs; they hand in resignation letters while handing out new business cards to their former co-workers. And that is something to be proud of!

But… you can’t get happiness done

Sustainable happiness is something you cultivate, experience, and feel. The kind of happiness that sustains you through the ups and downs of self employment is rooted in knowing who you are and what matters most to you.


The best measure of a person’s happiness, experts agree, is the quantity and quality of their relationships. Relationships aren’t done. Relationships grow through connection, through beingwith another person. It doesn’t happen through transactions, but with an exchange of vulnerability.

You have to slow the hell down, in other words. Give happiness time and space to develop on the inside or the outside craziness of the entrepreneurial lifestyle will eventually crush you.

Slowing down is not something I do easily. I prefer to run at full speed until I collapse in a heap or slam into a wall, either of which puts me flat on my back and completely useless. And that’s best case scenario.

Worse case scenario is falling so hard you never get back up.

Quitting is a potential “side effect” of depression. So is doing a half ass  job So is suicide. That’s a real risk that entrepreneurs are wise to remember.

 You can’t change the world if you’re dead.

I don’t believe we are meant to run from our happiness. In fact, I think perennial unhappiness is a sign that we’re off track, that we’re moving away from our purpose rather than towards it.

Entrepreneurs might be prone to depression, but you aren’t destined for it. It is possible to be happy and be a forward-thinking, self-starting, optimistic rock star who gets shit done. In fact, I suspect that’s exactly what you were made for.


“This post first appeared on In Pursuit of Happiness.”

The Best You

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