Why We Need To Fail More

Much of the research that I read and write about is geared towards achieving more success.

We work on time management and productivity so that we can accomplish more. We study investing and personal finance so that we can be more successful with our money.

There is a major focus on success in our culture and not much attention paid to failure.

But maybe that’s wrong.

Maybe we should be failing more.

Failing Your Way to Billions of Dollars

Tim Ferriss interviewed legendary investor Ray Dalio on a recent episode of his podcast. When asked about his failures, Dalio went on in great detail. When asked to recall a big win, he stumbled and searched for a minute before coming up with one.

Dalio is worth $17 billion. He’s probably had some big wins.

He went on at length about the benefits of making mistakes, and noted that you learn far more from failure than you do from success.

In fact, he has implemented a system for his company in which employees highlight their own mistakes and analyze them for lessons learned. 

This system seems to be faring quite well, as his company now manages $150 billion.

Learning From Failure

Failure helps us learn.

In one way, failure helps us learn what doesn’t work. This is valuable, but can be a very roundabout way to get anything done.

More importantly, failure helps us learn about ourselves. What aren’t we good at? What are our weaknesses? Where are our blind spots?

Figuring these out allows us to adjust and correct for them. This, in turn, allows for greater success.

The Failure Resume

Pete McPherson, on his Do You Even Blog podcast, recently gave his failure resume.

For almost an hour, Pete listed off the various online ventures he had launched that had not gone anywhere.

Then, like Ray Dalio, he highlighted the reason for each failure. Pete was able to identify where he went wrong, what his weak spots were, and what his likes and dislikes were in entrepreneurship and online ventures.

Pete has taken the lessons he has learned from a series of failures and used them to create a whole new venture that brings value to a lot of other people, myself included.

My failure resume would be very short and unimpressive.

This sounds like bragging, but I promise you it is not.


A lack of failure is a meta-failure larger than any individual failure.

Let me explain.

Failure is, at its essence, a sign that you attempted something that you couldn’t achieve.

Sometimes you just barely miss. Sometimes you don’t come close. Sometimes you fail due to something outside of your control. But every time you fail, by definition, you were unable to succeed in that scenario.

It also means you were trying to push the envelope. You were testing yourself beyond your current skill level. You had big dreams that you couldn’t quite reach.

The simplistic view of a lack of failure focuses on the first part. You never failed! You’ve been good at everything you attempted! Amazing!

But what about the second part? A lack of failure shows that you aren’t pushing the envelope. You aren’t challenging yourself beyond your skill level.

Your dreams are too small. You are not reaching your full potential.

Are You Missing Enough?

In the 2012 presidential election, Nate Silver and the stat nerds over at FiveThirtyEight correctly predicted the winner in all 50 states and the District of Columbia. People were amazed.

Silver later said that it was a sign that their predictions were too conservative.

Silver’s point was that they had predicted a number of states to be very close. For example, FiveThirtyEight gave Obama a 50.3% chance of winning the state of Florida. This is pretty much a coin toss. 

If Silver’s numbers were accurate, he shouldn’t have correctly predicted every single one of those coin tosses. One or two should’ve gone the other way just based on sheer odds.

He should have failed more.

In a similar example, I remember Silver discussing going to the airport. (I don’t recall when this was and I can’t find it online, so I am paraphrasing from memory here.)

He said that if you never miss a flight, you’re wasting far too much time at the airport.

Basically, you need to leave much earlier to have a 100% chance of catching your flight than you do to have a 95% chance of catching a flight. This gap is enough time that it is worth it to miss 1/20 of your flights to save that time up front.

You’re harming yourself by not taking enough risk.

(I should note that I don’t necessarily agree with this premise, as time waiting at the gate can be used for reading, writing, or other productive work and doesn’t need to be considered wasted time. That said, the underlying reasoning still stands)

Do You Fail Enough

I’ve never missed a flight. 

My list of failures is minimal.

I need to change that.

How about you?

10 thoughts on “Why We Need To Fail More”

    1. A lot of my self-improvement over the last few years has been based around thinking through what flaws I would not want to pass on to a child. I would definitely want my kid to be less risk averse than me, as I feel it has held me back and I wouldn’t want the same fate for my child.

      Thanks, Emily.
      Matt recently posted…How to Earn More MoneyMy Profile

  1. Thanks for the mention Matt, though it did remind me something else I heard on the Tim Ferriss podcast (the one with Marc Andreesson):

    (when talking about the popularity of “fail quick,” and “pivot,” etc) Marc said “back in my day we just called in a fuck-up.”

    Just a funny thought 🙂

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