Cy Young has the most losses.
Nolan Ryan has the most walks.
Todd Hanson says, “Do it for free for ten years.”
Wedding photographers say, “I just take way more pictures.”
And I just shared my story of starting endless blogs over years and years and years before I finally had one big pop. So say you’re with me. You know failures result in more successes. We know that in our heads.
But how do we do that in practice?
Well, let’s close with three key things that will help accelerate your failure rate and therefore quicken your ability to suss out whether you’re on the right path, when you should turn the other way, and where you should double down.
Here they are.
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 on to something good. But 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.
Like, 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 gonna 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 universe conspires to keep you there. Stay in your lane. Stick to your specialty. It’s nobody’s fault. To move through this volatile and 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 own knowledge in this 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 and explore new ground and try new things.
What’s the solution?
Go to parties.
Where you don’t know anyone.
Accept the far-flung invite, 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 like 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, you’ll 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.
Lose more to win more.
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 $1000 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 starting all those websites, I was in the two-figure game. $10 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. I could afford two-figure risks, two-figure experiments, two-figure flops—but it ended there. I couldn’t afford three-figure risks because I couldn’t afford three-figure failures. And four figures? No way. So that meant no graphic designers for When I Was a Kid, no loading Ghettohouses.com onto a superfast server, no buying an hour of consulting from a retired music industry expert for LabelZero.com.
No.
I was in the two-figure game.
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 if I wanted to try something, try anything, and it cost three figures or less—I would do it. I got stamps and stickers and postcards printed for my book launch campaign. I moved the site on to a superfast server. At the request of some radio stations, I got a (gasp!) landline to do interviews from home.
Some of those three-figure risks worked. Others were failures. But remember: You win some, you learn some. And do let me know if you’d like a pack of five thousand old stickers, will you?
These days my podcast 3 Books is an example of my 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.
Lose more to win more.
We always hear people say, “Count your blessings.”
The idea is that when you’re swimming in misery, it’s a good thing to remember all the things you’re grateful for to cheer yourself up. Do I believe in that? Absolutely! That’s why I wrote 1000 Awesome Things. I literally needed to write down a thousand awesome things to count my blessings and cheer myself up as I was processing the loss of my marriage and my house and the life I had known. I needed to count those blessings to help my brain move forward and see it as a step.
But you know what we never count?
Our failures. Our losses. The times we hit the ground.
Writing this book was the first time I had to revisit all those old websites that bit the dust. When I started writing this chapter, I thought, “I need to tell people about the three failed websites I started before the big one.” After I started writing, I remembered a fourth. While editing, I remembered a fifth. Then a sixth. They kept coming. There are probably others I’ve completely forgotten about because their half-life was like two weeks.
It felt good to revisit those losses.
They originally sat in a part of my brain that I wanted to delete. To not share! To keep quiet about. But the truth is 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.
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.
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.
What do I write?
“I spent time and money launching a website and nobody visited. What a disaster! But I guess I did find a great web developer I can use next time. And I own the domain so I can try something new or sell it down the road. And today I yelled at my toddler. I feel terrible when I do that. I was tired and hungry. But that’s no excuse. I have to remember I need snacks and time-outs just like he does.”
Admitting failure is hard. But you can do it. Trumpet them! Be proud of them. Because you learned from them and they were the fumbles on the path that got you here. You wouldn’t be here without there. And you can’t get there without here.
This is really hard for people.
Because it means couples 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 the 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 airtight vacuum of perfection. “Here’s the cherry-picked list of places I worked at with the cherry-picked results I delivered!” Yeah, riiiiiighhht. 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.
We need to talk about failures. Flops. The more we have, the more we grow. So put them out there. The jobs you sucked at, failed at, got fired from. The relationships you failed at. The goals you didn’t accomplish. We know they moved you forward. Share that. Share how. Not only will owning your failures humanize you, but being honest about your trip-ups and slip-ups means honoring how you got to where you are today.
Acknowledging that growth helps you recognize and appreciate it.
Do it for free for ten years.
Take more losses.
Take more pictures.
And talk about it.
Lose more to win more.