How To Fail Good: Why Writing About Failure Leads To Great Success

A few months ago I was sitting down with an E3C member to help them work out some ideas surrounding blogging. They were looking at starting to blog as a companion to their work as a designer and illustrator but they were stuck on one detail; where to start.

They were having some serious problems with finding blog topics and as they know that I am somewhat prolific in the writing of blogs, quantity not quality, and never have any issues with coming up with blog ideas. We started to talk about some things they might want to blog about and they mentioned that there some things they’d done wrong but she “obviously couldn’t write about that.” My answer? Why the hell not?

Recently I was asked to speak at BlogJam, a blogging conference in Halifax. I was told that I could come up with whatever I wanted to talk about as long as it was about blogging. My topic? Failure. Why is it ok to fail? Why is it ok to write about failure? Why do I hate Tim Ferris so much? These were the blunt instruments of my talk. Here are the finer points.

I’ve not failed. I’ve just found 10,000 ways that don’t work. – Thomas Edison

I blog about a lot of things but lately I’ve taken to blogging about my children because who doesn’t like hearing about what a beautiful little snowflake my daughter is and how my son is the top of his class. I feel like I’m a pretty good dad. People ask me a lot of questions about being a dad and they seem to be relatively happy with the answers I give so why not write about it. But I don’t write about how easy bedtime is and how I make children’s clothing completely out of discarded kittens. Why? Because I think that’s dumb. That’s what everybody is blogging about. Well, maybe not the discarded kitten part. But there are 101,000,000 parents, mostly moms, who just love to talk about what a joy their beautiful bundles of joy are. That is not what Chewy and Vader is about. Chewy and Vader is failure.

My other blog is OneRedCat. It’s where I share my “musings” on businesses, startups, copywriting, web development and whatever else the hell I feel like talking about. My most popular posts of all time include titles such as Stop Falling Down The Stairs, How And Why My Last Project Crashed and Burned In A Fiery Inferno of Failure: A Love Story, I Suck At Photoshop and I’m Not Cool But At Least I’m Honest. Why would people put their stock in someone who seems to be so confident in his ability to be terrible at things? It all comes down to one simple concept of human psychology.

No one cares what you did…they care what you did next.

I spend a good portion of my day trying to sort through everything that went poorly in the last 24 hours, both as a parent and as an entrepreneur. If you are either of these professions, you’ll probably feel just about the same. This is not to suggest that there are not great successes that come out of a given day as well. When you’re told that your son is performing admirably at preschool, is kind and caring and is helping many of the new kids acclimate themselves to school, that’s a win. When that same son reaches out to you and you lovingly take his hand, only to learn that he’s had in his urine-soaked pull-ups for the last several minutes, that’s not a win. That’s failure. When a client says that they think you’ve done a great job and post kudos all over social media, that’s a win. When your entire venture comes to a halt before it ever really gets started and you never ever have a paying customer, that’s not a win, that’s failure.

Success is stumbling from failure to failure with no loss of enthusiasm. – Winston Churchill

What I’ve learned, from decades of work experience and what seems like decades of parenting is that everybody loves a good redemption story. People aren’t inspired by stories about people who had an idea and then executed it without any issue. This is my issue with people like Tim Ferris. ‘I just decided to be awesome and it all worked out.’ Thanks Tim. And that helps me do what? As someone who has been responsible for hiring and firing (you can say terminating or restructure all you want, I fire people) people, I don’t care if they’re awesome at things out of the gate and have never faced adversity. When people tell me that they can’t recall a time where they’ve struggled at work, I show them the door. I don’t want to work for and with people who don’t know what to do when things go south. I want to know how people react to not knowing an answer, blowing it with a client, doing something stupid.

When I’m writing, I don’t limit myself to the things that have gone well. While I love to write about the times I’ve knocked it out of the park, I also love to write about all the times that I’ve struck out. My post about falling down the stairs didn’t end with me falling down the stairs. My story about my business failing didn’t end with my business failing. My story about stealing my son’s my little pony so that he would go to sleep didn’t end with my son not going to sleep…ok…well…that one did actually. But most of my stories are about redemption. Repeat the mantra. No one cares what you did…they care what you did next.

As some of you may or may not know, I’m a big sports fan. Big. Sports. My favorite basketball player of all time is a man you may have heard of named Michael Jordan. At one point, they released a commercial for Jordan that had the following line.


That stuck with me, always. A lot of people think that life was probably very easy for Jordan, being that he was such an extraordinary basketball player. What many people don’t know is that he got cut from his junior high basketball team. Michael Jordan didn’t make his junior high basketball team. For those that aren’t sports fans, that would be like if Albert Einstein failed math…which he did by the way. Sensing a theme here.

Everyone struggles. At least everyone that I want to be around. People who struggle do so because they try to achieve great things. Achieving great things isn’t easy. That’s why they’re great. So the next time you’re struggling with ideas for content, think about the last time you struggled. How did you deal with that struggle? How did it feel? How did it make you better? According to Conan (barbarian, not comedian), what doesn’t kill you makes you stronger. Now, while I don’t entirely agree with that statement, I agree with the sentiment. Adversity makes you a stronger person if you choose to allow it. There are those that feel beaten and broken by failure. Failure is a teacher. I’m not suggesting you go out and fail. I’m suggesting that you try things that allow for the possibility of failure and that if/when you fail, you share that experience. It will make you and the people around you stronger. And if Tim Ferris is reading this, which he apparently can do to his semi-bionic brain and ability to think and live without sleep, congrats on all of your great success. I’ll start reading when you start failing.

Failure isn’t fatal, but failure to change might be. – John Wooden

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