An entrepreneur’s secret to happiness, in 5 steps

In July, I set off for an eight day holiday, per the recommendation of a friend and mentor. It didn’t matter where I went, so long as there was a place to melt in a lounge chair, and lots of water (I’ve lived near the ocean for nearly my entire life, and it has become a prerequisite to my relaxation), or so I thought.


I chose Jamaica, and as you can see, it was gorgeous. What will surprise you, however, is that it was what I learned and the events that would follow when I returned to city life, where the treadmill is perpetually dialed at 14 (out of 14), forcing one to jump on in full sprint, would relieve me from burnout, not the sun, the lounge chair, and the horizon’s endless blue water. That’s right, relaxation wasn’t the answer.

While in Jamaica, I set my iPod and sunscreen on the lounge chair next to me (all lounge chairs in the entirety of Jamaica are arranged in couples, since singles rarely travel there, apparently… traveling alone, the subject of another story), and I read like crazy. I read about sustainable design, the application of economic theory to aspects of weird human behavior, and of course… the state of happiness. This book on happiness, however, didn’t claim to be a run of the mill self-help guide to finding happiness. It was written by a brainiac Harvard psychology professor (Daniel Gilbert) about the limitations of the mind, and its perceptions of the state of happiness. As such, there was little to take away from the book aside from a faint sense of hopelessness and frustration about the lack of control we have on our emotional states… except one thing. One big thing that applies directly to entrepreneurship.

In the book, Gilbert mentions a study of how people recall past experiences, mainly taking chances. Interestingly, yet not necessarily surprisingly, the study concluded that people almost always felt regret for not taking chances in their lives, yet those who took many chances almost never regretted taking them, regardless of outcome. I found this simply fact pretty inspiring, and clearly it is appealing to all of us, who have invested in taking risks, in hopes of making a real difference in the world in which we live.

So what?

When I returned to San Francisco, I immediately spread myself as thin as possible. I explored three other business ideas, consulted for free (which led to some fantastic, paying projects), and started exploring the idea of creating a professional network in San Francisco for entrepreneurs interested in creating worldchanging businesses. I was destined to fail in at least one of these ventures, and reveled in the possibility of failure.

So, when you are about to curl in a ball and scream in frustration over what appears to be a complete lack of control over your success and state of happiness, follow these steps:

5 Steps to Happiness Through Entrepreneurship

1. Follow your passions.

What would you do with your life if you were to win the lottery? Would you become a writer? Then stop trying to convince yourself that you’ll be happy taking the safe path by going to law school. Got it? Now, read step 2.

2. Aim to fail.

Okay, your goal isn’t quite to fail, but be open to the possibility, and get ready to pull one of those ninja moves, jumping straight to your feet from a flat-on-your-back position. If you are going to fail several times, and you may, don’t waste a minute on your back, and savor the experience. It is all part of the game.

3. Fail smart.

Like learning how to fall the “right way,” when snowboarding (if this applies to you, try falling on your fists, as if you are punching the ground, not on your open hands, which puts your wrists at risk of injury), learning the right way to fail in one’s personal and professional experiences takes more than guesswork. Be sure to take the necessary time to learn from mistakes, to ensure that the next time around, you’re chances of success will be much improved. We can all learn volumes from our failures, so don’t waste time chasing your tail after you’ve discovered that it is attached to your ass.

4. Don’t even think of doing it alone.

With the addition of each partner, especially those of diverse experiences and skills, your probability of success is greatly increased (according to Startups that Work). Even more importantly, a great team makes for a great ride and lasting, worthwhile friendships.

5. Start now.

The hardest part is getting started. So, stop talking about your big ideas and start letting them speak for themselves. Wouldn’t you rather create Facebook than be one of the morons who are suing someone else for “stealing their idea?” Ideas are cheap.

Good luck! More on my success stories to come… I can’t wait to hear yours.

4 Responses to “An entrepreneur’s secret to happiness, in 5 steps”

  1. Samir Mehta Says:

    Excellent post. The example in 1 sounds a bit too familiar to me though… :-)

  2. Rod Says:

    Nice, awesome post. I agree on all accounts.

    Failing smart and starting now are terribly difficult states of mind to get yourself into but once you’re there things start coming together naturally.

  3. Cathi Says:

    Great insight. Have you thought about contributing your ideas to the Entrepreneneurs Foundation or World Business Academy, etc. Having both a Masters in Nonprofit and an MBA, yet without financail resources has limited my impact. Any ideas???

  4. A Says:

    Thanks for the advice. Next step: start my own letterpress and screen printing shop.

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