These phrases are spouted endlessly these days but there’s one giant thing missing from the conversation: How. After all, we grew up thinking that less failure equals more success, right? And now here’s the world suddenly telling us to fail more.
Today I’m going to lay out these three ways to help accelerate your failure rate and therefore quicken your ability to suss out when you’re on the right path, when you should turn the other way, and when you should double down.
1. Go to parties (where you don’t know anyone)
Success blocks future success.
Say you get good at one thing and your brain, like my brain, wants to keep chasing that bunny. You struck oil? Pay dirt! You’re onto something good. The problem is that when you start making it and raking it, you’re also missing out on all the other options, all the other efforts, all the other potential flops that might have led you to even greater success, however you define it.
Say you get into real estate in your twenties, you sell a few condos, you feel like you’re really onto something. Great! But that also means you’re going to play the real estate game and maybe never fully realize that had you not quit ballet in your twenties, you might be on Broadway right now.
Success blocks future success.
The issue here is that when you’re good at one thing, the world conspires to keep you there. To make you stay in your lane. To make you stick to your specialty. That’s nobody’s fault. To move through this volatile, chaotic, and ambiguous and complicated world, we all need mental labels to filter and sort all the people in our lives. “You’re my real estate agent friend!”, your friends think. So when you chat with them at birthday parties, it’s about the market and interest rates and when they should sell. All those endless conversations serve to deepen your knowledge in that one area, make you more successful in this one area, and then crystallize your identity even further, making it harder and harder and harder to mentally break out, explore new ground, and try new things. Some researchers call this 'cognitive entrenchment.'
What’s the solution?
Go to parties.
Where you don’t know anyone.
Accept an invite to an event far away, hit a reading by an author you’ve never heard of, grab a ticket to a concert in a genre you never listen to, grab a cocktail at the hotel bar after your flight, attend the online meetup for an old passion you forgot you had—and, of course, go to parties.
Will it be awkward? Uncomfortable? Sometimes. Sometimes, sure. You might not meet anyone. You could have three superficial chats and connect with precisely nobody. You may leave feeling as though you just wasted your time. That’s the risk. That’s the downside. That’s the potential for failure.
But what’s the potential gain?
The potential gain is that you’ll meet interesting people in interesting places.
The potential gain is that you’ll drift into other lanes, go down new thinking paths, and you’ll slowly unfurl yourself from whatever mental sleeping bags you’re rolled up in.
And maybe your experience will provoke and prompt new ideas, new efforts, new risks, and new ventures that you’ll fail at and learn from.
2. Have a failure budget
Set aside money for failure? Am I joking?
No, I’m not! Set aside money for failure. Maybe it sounds odd. But come up with a figure that you can use just to try random stuff. Assume it will fail! But try it anyway. Maybe $20 at an oyster bar, $200 for a boxing class, or $1,000 to go to a distant music festival.
If it works for you to use an absolute number, great. That’s perfect. But if you’re not exactly a budgeter, I also have a mental model I use in my life that can be a simple way to think about this.
It involves deciding what figure game you’re in.
Call it the Number of Figures Game.
Let me explain.
When I was a kid and I started my first few websites, I was in the two-figure game. Ten dollars to buy a URL? Well, that expense was approved. But nothing else was! I knew I was in the two-figure game because I had no money.
What was my failure budget? Anything that cost two figures.
When I started 1000 Awesome Things, I moved to the three-figure game. I was a grown-up now. I had a job. I figured that if I wanted to try something, try anything, and it cost three figures or less—I would do it.
These days my podcast 3 Books is an example of me spending my failure budget. I really wanted to make a podcast that was ad free, sponsor free, commercial free, and just a piece of beautiful art. To me, anyway. So I spend around $5,000 a year making it. Flying to interview guests, production costs, recording equipment. It’s a four-figure “failure budget expense” that I love spending every year. Why? Because it’s vastly improved my learning rate, too.
Can you keep moving up? Sure. How high can you go? Well, if you’re a hip-hop star or tech billionaire, maybe you’re in the seven-figure game. The number depends on you. Your comfort level. Your risk tolerance.
My goal isn’t to tell you how many figures you should plan to spend on failures. It’s to give you a mental model you can apply in your life to accelerate your lose rate and therefore accelerate your win rate.
3. Count your losses
We always hear people say, “Count your blessings.”
But you know what we never count?
Our failures. Our losses. The times we hit the ground.
When we look at our flops, we’re really giving ourselves credit for all the learning and stamina and resilience baked into those moments when we made ourselves a little stronger.
One exercise we do in my family now is going around the dinner table playing a game called Rose, Rose, Thorn, Bud. Roses are gratitudes or highlights, thorns are flops or failures, and buds are things we’re looking forward to. Even though the research on gratitude points to writing down five things you’re grateful for as a path to a healthier mind and body, what we find is that including the ‘thorn’ in the practice actually helps us even more.
Why?
Because it helps us slowly work against the natural muscle of “less failure equals more success” and train our brains to find the lessons and learnings that come from defeat or setbacks.
Counting up our losses and taking pride in our failures is really hard.
Really, really hard. We are taught to hide failure, feel ashamed of it. And here we are talking about wearing them as badges of honor.
What are some other ways to do it?
If you keep a journal, try writing down your successes and your flops. Be honest, and count your failures as they happen. Be kind to yourself by giving yourself credit for each one.
In a corporate setting, it means leaving the gaps on your resume or your LinkedIn profile. Even accentuating them by sharing your travels while you were between jobs or the six months you took off to be with your daughter after her second miscarriage. These failures, through the lens of a wise recruiter, actually strengthen who you are.
This is really hard for most people to do.
Because people can’t tiptoe around all their past failed relationships when they get into a new one. I’m not saying they should lay them out on the first date like a display case of painted ceramics. We don’t want to confuse counting failures with plain poor judgment! What I’m saying is that once you’ve built trust in a relationship, then lay them out. Be honest and share what you learned from each one.
This is really hard for people.
Because it means leaders can't pretend their resumes are an air-tight vacuum of perfection. "Here's the cherry-picked list of places I worked at with the cherry-picked results I delivered!" Bullllllllllshit. Nobody buys that. We know you're human. Do you know you're human? If you don't, then that's a bigger issue.
We don't trust people who haven't failed, and we really don't trust people who don't even know they haven't failed or like to pretend they haven't failed.
So, yes, indeed!
Fail more!
Fail faster!
Fail better!
Avoid cognitive entrenchment by increasing your failure rate to dramatically accelerate your learning rate.
