What would you do, if you were certain to fail?

Why the allure of success is holding us back

In order to be an entrepreneur, you have to be a little bit diluted.

That’s because the odds of starting a business, and then staying in business for just five years, is little better than random. Meaning the fate of your entire company is effectively a coin toss. And yet, despite the odds, each year millions of aspiring founders will toss that coin.

An orientation towards success—and belief that hard work will improve your odds—is essential for becoming an entrepreneur. Which implies two things: the first is that entrepreneurs are driven by outcomes. The second is that they believe an achievement of that desired outcome will result in a desired life.

It’s a bit like how all high school students believe that admission to an Ivy League school will solve all their problems—when the sad reality is it’s just the beginning. For a student, their orientation towards success has them taking extracurriculars that they don’t actually care about, learning languages they’ll never use, and forgoing their youth in an attempt to grow-up as fast as possible.

We do much the same as business owners, founders, and entrepreneurs. Our orientation towards success has us evaluating business ideas based on their likelihood of profitability. We visualize what the future will look like when we win, and work backwards from there. Setting up goals and milestones all along the way.

An orientation towards success uses achievement as a north star, and that’s a problem.

The mirage of starting a business

As far as I can tell, there are really only three reasons someone would ever want to start a business: First, to do what you want, and how you want to do it. Second, to create your own schedule, with complete control over when and where you work. Third, is to uncap your earning potential.

But every experienced entrepreneur I’ve talked to, has stressed how fickle these objectives are.

Your investors will tell you exactly what to do and how to do it. Your customers will tell you when and where you should be working. And although this is anecdotal, I don’t know a single responsible startup founder who pays themselves more than 5-figures per year.

So it seems like entrepreneurship is mostly a losing game. Not only are your odds of survival extremely low, but the very notion of success is little more than a mirage.

So how do you win a losing game?

Two years ago, before creating Startup Social, I moved to San Francisco with no friends or connections. I was dropped in the middle of the tech bubble, yet I had never worked in tech. I felt very much like an outsider.

Today things are quite different. Now I regularly have lunch with people who charge $300-400/hour for their time: business coaches, CTOs, designers, board members, startup advisors, you name it. I’ve never been charged to speak with these folks, and many of them I can now call friends.

How did that happen?

When I created Startup Social, I began by asking myself “How do you win a losing game?” Or, more concretely, “How do I design a business that can still succeed despite the terrible odds stacked against me?” After sitting with this question for a few days, I landed on what I believed to be the only logical answer— just assume that I’m going to fail. 

The purpose of Startup Social is to build relationships among emerging technical professionals in San Francisco. So people—who are incomprehensibly out of my league—reach out to me regularly, wanting to be a part of that. In this way, my business acts as a magnet. It attracts exactly the types of people I want to spend my time with, to me.

So the success of my business has now shifted from growth, email sign ups, and generating more revenue, to attracting the most interesting people I can find. Which means that when we go out of business, I will still have gained something immensely valuable.

This is the result of something I call—Orienting towards failure. 

How to choose your business ideas

Let’s say you have two great business ideas you’re considering.

Each one has qualities you find attractive, and each has unique downsides as well. With an orientation towards success, you might take both ideas and put them down on paper. You’d analyze the upside potential of each and try to quantify the likelihood of achieving that outcome. You’d then bring your ideas to a trusted advisor and get their opinion on which idea is more likely to succeed.

This is neat, logical, and a classic orientation towards success.

But with a orientation towards failure, we might instead ask ourselves—Which idea would I pick if I knew I was certain to fail?

With the knowledge that—regardless of whatever you choose, you’re going to fail—you become liberated. You’re free to start contemplating more interesting questions, like:

  • Will I have fun performing this work?

  • Will I attract interesting people to my cause?

  • Will I enjoy spending time with my target customer?

  • Will I cultivate a skill that I’ve always wanted to have?

  • Will I learn something that I can bring to my next project?

  • Will I foster relationships that will last beyond this business?

  • Will I build a reputation that will follow me to my next endeavor?

An orientation towards failure radically shifts how we look at building a business. Everything moves from the odds of making money, to our likelihood of creating an engaging experience for ourselves and those around us.

With the acceptance of failure, we’re now free to focus on the things that actually matter most. Ironically, this shift in priorities and time horizons, will almost certainly increase our odds of monetary success as well.

For me, an orientation towards failure focuses my attention to surrounding myself with brilliant people, and doing work that I find enriching. But more than anything, orienting towards failure means that the experience, in and of itself, is enough.


PS. If you’ve made it all the way down here and don’t feel that you’ve just wasted five minutes, consider hitting the Like button on this essay.

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