How to Fail as an Entrepreneur


Leo Babauta of

Leo Babauta

Just follow the advice offered by Leo Babauta in his recent post on, “The Not Knowing Path of Being an Entrepreneur.

I’m a fan of Leo’s. I read zenhabits regularly, and I have bought his excellent book,The Power of Less, which I’ve read twice. For the most part, I find Leo’s Buddhist worldview to be wise and useful (maybe that’s a little unBuddhist of me). But this piece on entrepreneurialism misses the mark, precisely because he superimposes his Buddhist vision on entrepreneurship, a phenomenon which he might not fully understand or accept.

For example, if you are planning to start your own business, you need to be prepared to control outcomes – to be willing to move heaven and earth to control outcomes. Entrepreneurs are, above all, people who seek to control outcomes. Entrepreneurs have a vision for their business’s success. They have goals to get to that vision. They try to make every day as productive as they can, and they try to achieve certain performance targets.

Leo says all of that is useless, an illusion because people can’t know how things will turn out. Leo says the pursuit of the illusion produces anxiety which impedes success. According to Leo, not knowing how things will turn out is OK, and you should relax into that uncertainty, liberating yourself to discover what the future brings. Because, even if the worst case scenario happens and the business fails, Leo “[Honestly thinks you’d be fine with that.]”

Wrong, my friend. Believe me; you’d be pretty darned far from “fine with that.”

If you want to be a CEOwner, you’d better commit yourself to controlling outcomes. Get ready to live with anxiety. Plan in detail, so that you are able to improvise when the plans blow up. Be ready to work very long hours indeed, with a ruthless dedication to productivity. Hit your targets if you can, and if you can’t, figure out a way to hit them next month.

To create a business out of nothing. To enable its survival through the inevitable obstacles you’ll face. To grow it in the face of uncertainty and competitive pressure. To nurture it to a level of sustainability. All of that requires “drive.” You can’t glide to success.

Honestly, if you’re planning to invest your nest egg into this new business, how philosophical will you be about the possibility of failure?

And if you’re trying to convince investors to put money into your new venture, how reassured do you think they’ll be with a “Not Knowing” business plan?

I mean, really, it’s pretty absurd.

Successful entrepreneurs – people who build businesses that have significant value apart from themselves, businesses that go public or get bought by other companies – are OBSESSIVE. Their anxiety is fuel. Their intensity is what convinces their customers to buy from them. Winning is everything. Failure is unacceptable. This might be a stereotype, but it’s a stereotype based on reality. In my experience, entrepreneurs only become philosophical through success, and even then, when they can afford to fail, they hate to fail.

If your idea of becoming a CEOwner is gearing down, having more time to yourself, enduring less pressure in your life, and enjoying some mellow journey of self-discovery, then don’t bet the nest egg. Organize your new venture as a kind of hobby, whose economic success is secondary and immaterial to your own financial well-being. In other words, don’t even pretend to be an entrepreneur. Then you’ll have the luxury of giving Leo’s approach a try. But be sure to let me know how that works out for you. And good luck.

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6 Responses to “How to Fail as an Entrepreneur”

  1. Brad Forsythe March 25, 2013 at 5:09 PM #

    Great points, Rick. Many entrepreneurs must sign personal guarantees in order to get the capital needed to fuel their businesses – pledging their personal assets (homes, savings, cars…everything of commercial value) to the bank if the business fails. I wonder if Leo might have a lower tolerance for business failure with a personal guarantee hanging over his head.

    • Rick Barlow March 25, 2013 at 6:29 PM #

      You are right, of course, Brad. Been there. Done that. But banks might be even more reluctant than investors to put money in the hands of a guy with a “Not Knowing” business approach.

  2. Heather Stone May 26, 2013 at 12:33 PM #

    Hi Rick,
    Thanks for the insight. I enjoyed reading your post via the BizSugar community. One observation I’d make about Leo’s points here. I agree it’s probably a bit extreme to suggest that failure is OK. However, I can understand that entrepreneurs may sometimes be unable to see or to understand the best outcome of their business models. We’ve all heard the stories of entrepreneurs who go into a business only to discover its the wrong one. They realize the product they’re trying to market would be better as a service. They realize the target market they’re aiming at is all wrong. Somebody totally different likes their product. It can be inconvenient when a business doesn’t translate smoothly from plan to reality, but the best entrepreneurs can adapt. Thanks again for sharing!

    • Rick Barlow May 26, 2013 at 1:00 PM #

      Thanks, Heather. I would be surprised if most start-ups didn’t experience some “inconvenience.” The ability to adapt is probably the most essential characteristic of a successful entrepreneur.

  3. Teepu May 26, 2013 at 6:48 PM #

    I honestly think Leo is right. I guess, I’m not the type of guy to stress myself out too much. Failure is never inevitable in business. There are a pool of entrepreneurs out there who work so hard everyday and their businesses ending up as failures. Entrepreneurs need to let go of one thing they can never have, control. Once you learn to let go, you’ll see things more clearly and become a better entrepreneur. Just my two cents. Thanks for sharing in Bizsugar!

    • Rick Barlow May 26, 2013 at 10:18 PM #

      We are, as they say, all the victims of our own experience. Thanks for your two cents.

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