To Succeed in Life, Learn How to Fail

No one likes to fail. We feel embarrassed, angry, frustrated, self conscious, and vulnerable. But I’ve recently begun to feel comfortable with failure and started embracing it. I want to share some of my feelings about failure.


None of us want to look incompetent. And you have every right to be worried you’re incompetent because people make these sorts generalizations all the time. Human brains are terrible at complex analysis. We use shortcuts when we don’t have the time, energy, or wherewithal to use higher brain functions. It’s an evolutionary adaptation to conserve energy.

Understanding this allows you to dismiss most critics.

The Moral High Ground

Realize the power of trying and failing as a strategy for learning. Businesses are increasingly turning to this type of strategy, pioneered by Toyota in the 1980’s. Fail sooner, rather than later, and you can course-correct before you’re too highly invested. Take solace in the comfortable position that while most folks are reading Miley Cyrus gossip on BuzzFeed, you are actively learning.

By taking a risk, you have the moral high ground. No one can fault you for trying to learn something new. If you fail, you will learn.

Provide Clarity Where There is Confusion

When you embrace something different, it requires a fair amount of effort on to reconcile why you’re deviating from the norm.

Talk the confused through your reasoning and use a narrative style if possible to increase empathy. And remain humble. Over confidence in a new idea will deter people from taking you seriously.

For instance, rent in SF is crazy. I’ve had the following conversation at least 5 times in the last month.

Stranger: “How do you like living in SF?”

Me: “I love it for the most part; only downside is the rental market.”

Stranger: “Ya it is expensive.”

Me: “I’m trying to find an unconventional way to live to reduce my exposure, like a boat. My fiance and I have talked it over and we feel like it could work.”

Stranger: “Oh ya wouldn’t that be the life!”

Me: “I grew up boating so I’m comfortable with the idea. The biggest hurdle is getting ‘liveaboard’ status in a marina.”

Stranger: “Oh, you were serious! There are waiting lists?”

Me: “Ya, municipalities have placed limits on the number of liveaboard slips and I can’t buy a boat on the hope that a slip will turn up!”

Stranger: “Interesting. Well good luck!”

Maximizing Return

Learn to view your failures in an objective fashion. Try to glean as much as possible from your mistakes. Use a 5-why’s approach to understanding just how and why you failed. Understanding why something happened or didn’t happen is a self-reinforcing process. It can lead to highly satisfying Aha! moments. Embrace this type of discovery.


The context under which I mostly talk about failure is in business. But “trying” doesn’t necessitate a physical activity. One can explore philosophical problems as well. I regularly entertain dozens of ideas, talking about them for a few days, weeks, or months, bringing them up in conversation, and generally annoying my family and friends to no-end.

Here are some ideas and ideas I’ve been playing with over the last several weeks:

  • Could we open source urban planning? Government? Law?
  • What role does government representation play in a world with instant communication?
  • How can we modernize government and make it more efficient with technology? It could be so much more lean.
  • Should I stop consulting and focus on DockLister?
  • Should I even be running DockLister?
  • As I grow increasingly cynical about our political system, do I even want to live in the United States?
  • What if I worked remote for the next 3 years, in a different city each year?
  • How can I hack real estate and find cheaper rent? Live on a boat?
  • How can I help Bitcoin succeed?
  • How many people are required to stage a protest?


I wrote this for every person who as ever failed to raise their hand in a class because they weren’t 100% sure of their answer. I was, and still am sometimes, one of these people. On some levels, this is a pep talk for myself.

Ignore everyone and raise your hand for every question. Really.

Learn how to fail gracefully and the fear disappears.