How to Succeed at Failing

I don’t know what you’re relationship with failure has been. But for me, it has always been a brutal, unforgiving mistress.

I was plagued with an older sibling who is instantly great at everything she does. If she became interested in something I wanted to do, I immediately gave it up so I didn’t have to compete.

Pathetic, I know.

She never had to try in school –  things just stuck in her memory. She could blow off class, and with the briefest read-through of the information before a test, she was still guaranteed an A.

Me? I had to put in a lot more effort. I couldn’t concentrate. I got bored. My interest in the subject dictated my grade. My feelings about the teacher were an even stronger indication of my success. I had an attitude problem.   

I couldn’t deal with authority – I still can’t. I can only follow the rules that make sense to me. I see broken systems everywhere!  

Don’t get me wrong, I was no hell raiser. Most of my teachers probably won’t remember me, unless my particular brand of apathy got under their skin. I usually just faded into the background and kept my self-pity and frustration to myself…unless I got pushed too far.

At that time in my life, failing at something would mean months of beating myself up, constantly reliving the event in my mind, and an indignant refusal to try again.

It wasn’t until I got a job that involved teaching adults how to use technology, that I realized how pathetic I had been. These grown-ass adults were wasting their time with hissy fits about how they couldn’t do it. The would lament that they were too old to learn, and that everything was too complicated.

They would give this little device so much power over their lives and their dignity. Getting one minor thing wrong and they would let their egos kill any chance of getting better – even though there wasn’t much on the line. I mean, all they wanted to do was check email and play a few games.

Instead of accepting that getting things wrong would be part of the process and dedicating themselves to improvement, they gave up almost instantly.

And as someone who already has an attitude problem, this PISSED. ME. OFF. Why spend your money to waste your time and get NOTHING out of it?I wanted to snatch their devices and let them know that they could have them back when they learned to act their ages!

But, I breathed through it.

And in the end, at least I got something out of it. I saw so much of myself in their attitudes. It got me thinking about my own reactions when things don’t go my way. I’ve improved a lot since I was a kid, but I’m still looking for ways to get better.

Anyway, I thought I’d share a few ways I’ve learned to squeeze every ounce of positivity that I can out of failure, instead of giving into it.

1. Learn to Dissect

Walk through everything that lead you to the point of failure. What got you there? What did you do? What didn’t you do?

Sometimes it’s hard to force yourself to think about a situation that ended badly. But, if you sit with your failure, I promise that you will find something of value in it.

You might learn something crucial about yourself that you could work to change. Maybe you have the tendency to self sabotage, maybe you overlook important details, or maybe you’re lacking some leadership ability.

Get self-reflective!

People tend not to be the best at evaluating themselves, especially if they aren’t practiced at it.  So, reflecting works even better if there is someone else to consult.

When I went back to school for marketing, one of my professors made me interview people close to me to figure out the details of how I was failing at a self acknowledged flaw: listening.

The people in my life are BRUTALLY honest. No one had an issue telling me how much I sucked at listening. It was so hard not to get defensive, but it did help me weed out my issues, and determine a plan for improvement.

I may have been failing, but unlike those tech trainees, I went out of my way to take the assignment seriously, and to get everything I could out of it.

I didn’t just improve my listening skills; I also learned humility and a process for self-improvement. There is a wealth of knowledge waiting at the bottom of failure if you’re willing to dive in.

2. Monetize Your Cautionary Tale

Most people will try to sell you on their knowledge of where to go.


Knowing where not to go is arguably more important. Wins can get you so far, but certain failures can destroy a business, so knowing how to avoid them is invaluable.

Once you’ve failed enough in a certain area, and you’ve taken the time to dissect those failures from every angle. You’ve gained a massive advantage over the people who haven’t bothered to learn what led them astray.

These people are doomed to keep making the same mistakes, because they don’t know they’re mistakes yet.

You could use this edge to start a consulting business. You could use this edge to create a webinar that people would pay for. You could use this edge to create content that peaks the interest of hiring parties. You could use this edge to get leverage at your current job.

Whatever you learn in your failure, don’t keep it to yourself. Just think how much people would pay not to have to learn things the hard way!

This is literally the entire premise of a business I’ve recommended on this blog before: Freelance to Win. A business, I might add, that brings in over $250, 000 a year.

Danny essentially positions his course as: I made the mistakes and learned the hard way, here’s the info so you can be an awesome freelancer right away.

Most people want to avoid failure at all costs. Embrace it, and you can’t lose.

3. The Social Advantage

Everyone has failed at something, and once you get comfortable with your failures, I’ve learned that sharing them openly is a great way to bond with people and provide entertainment.

For one thing, it shows that you have humility. How intimidating – and more importantly – how boring is it to spend time with a person who only talks about how great they are and all they’ve accomplished?

Being able to not only laugh at yourself, but actively invite others to join is a strength that not many people have.

For another thing, whether the other person admits it or not, they can 100% identify with your struggles. And usually, the other person will reciprocate with their own story anyway.

Trust me, it builds relationships much faster than talking about the weather!

So I share!

I do it in the posts on my blog. I do it to break the ice with new friends. I do it to fill awkward silences. I wear my failures as a badge of honor, because hey, at least I tried.


That’s all I’ve got today. Do you do any of this already? Do you think you’ll try? Let me know in the comments!  

And as always, let me know if you’ve got any ideas you think I should try!

– Jenn

Title photo credit: Craig Whitehead

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