Have you ever had fun failing at something?

It’s a weird question, the more you think about it.

Our entire modern world is built around the idea of being successful. We all want to be seen as popular, productive, and somewhat perfect.

Yet, the reality is very far from that. Most of our lives, we are dealing with small and large failures in some way or another. We forget someone’s birthday; we are late paying a bill, we get passed over for a promotion, or rejected on a date. 

Failures – big and small – are part of life. But for some reason, we avoid talking about them. We’d rather not present ourselves in a non-favorable way. 

This is why you rarely hear about divorces, layoffs, bankruptcies or other types of lifestyle indiscretions on social media. When you meet most people and ask how they are, they will say ‘good’.

It’s not that failures don’t happen – it’s more that we hide them, and don’t admit to them, even to ourselves.

But what if, instead of avoiding or hiding failure, we reframed it as fun?

Why Do We Fear Failure?

In my opinion, the biggest reason that most people don’t take more risks is a fear of failure.

It’s not the actual failure, but the fear of failure that stops us. 

There are genetic and sociological reasons why failure is less valued than success. But in the vast majority of cases, the actual risk of negative consequences is much less than we imagine.

For some reason, we believe that a failure will cause us to be ostracized or make us less valued by other people. The more times we fail, the logic seems to go, the less we are loved.

But is that true?

Do you actually love or value people less who you see fail in some respect in their lives?
Do you think less of someone for attempting something than if they never try?

Most people are so consumed with their own image and results that they pay little attention and give little time to judging the failures of others.

The more you think about it, the less ‘scary’ failure seems. Worst case, you lose time, money, or some sort of status in the eyes of others.

But you can always start over, you can always try again. You can always learn something valuable from failure and use it to your advantage next time.

The Flipside of Failure

Once you have been through a few failures in your life, you realize that what you worried about is rarely as terrible in reality.

Yes, we all fail, but over time, we rise again. 

Not only do we rise, but we can also use the valuable lessons to climb higher than before.

The flipside of failure – if we choose to keep trying – is that we gain something that success could have never delivered.

Once we see the value of failures, it can even become exciting to anticipate that another valuable lesson is on the way. 

At that moment, the shift begins; we suddenly see that failure has a ‘fun’ aspect to it.

When Failure Becomes Fun

When I was 35, I met someone who taught me about the ‘fun’ aspect of failure.

I had recently divorced and was looking to meet new friends. I decided to join a Meetup group for men looking to hang out with other men. 

One of the men I met at the Meetup was a guy called Dillon. He was a few years younger than me, and very different in the way he approached life.

By age 35, I had grown serious and obsessed with becoming a success in life, whereas my new friend Dillon was more interested in experiencing whatever life had to offer.

One night, our Meetup group was at a bar, and Dillon said to me, “Hey, want to have some fun? Follow me…”

I followed him as he walked up to a group of women and said, “Ladies, I know you don’t want to talk to me, but it would be ungentlemanly of me not to say how lovely you all look. Goodbye!” 

He turned around and walked all the way across the room to another group of ladies. With a smirk on his face, he said, “Excuse me, I seem to have lost my phone number… could I have all of yours?”

The women laughed at him. A few rolled their eyes.  But Dillon wasn’t phased by the reaction. He just walked back to his seat at the bar with a big smile on his face.

As a newly single man, I was dumbfounded by what I had just witnessed.

I said, “Dillon, that was a complete failure.”

Dillon laughed, took a swig of his beer, and said, “Dude, when you make failure fun, you don’t need success.”

In that moment, I thought that Dillon was clinically insane. 

But by the end of that night, I saw his genius. Within an hour, Dillon was surrounded by the single women from that bar, all laughing and giggling with him.

Dillon had fun failing, and the women knew that was unique. Hence, they wanted to be around him, instead of talking to the legion of men trying to impress them.

Failing for the Fun

After that experience with Dillon, I started to see that maybe there was another side to the failures that I had experienced in life.

Of course, I was disappointed that certain things in my life hadn’t worked out as I had hoped, but they also enriched my life.

Divorce taught me that not every relationship works out despite a lot of effort.
Career dissatisfaction taught me that chasing money above interest causes emptiness.
Losing money in investments taught me that emotions are not a good judge of actual value.

Inside these lessons was another level of value.

These failures gave me funny stories to tell to my friends, and even more, they gave me a sense of self-respect that I went for it. 

Yes, I screwed up.
Yes, I looked like an idiot. 

But what mattered more was the fact that I was still going, and I was older, wiser, and had a sense of humor about the foundering, misfiring, and collapses that were part of my life story.

“Holy shit, what a ride!”

There is a famous quote that goes “Life’s journey is not to arrive at the grave safely, in a well-preserved body, but rather to skid in sideways, totally worn out, shouting ‘Holy shit, what a ride!”

I’ve heard this quote attributed to Hunter S. Thompson, as well as an anonymous 95-year-old grandma. While the former is more likely, the latter is funnier.

But the point is the same: no matter who said it, life is more enjoyable when seen as a fun and funny adventure full of failures and successes, with no scorecard.

What I have learned is that when you learn to have an attitude of fun in any endeavour, it matters less whether it becomes a failure or a success.

The Fun is in You

As we grow into adults, there is a tendency to grow more serious and humorless. 

We tend to see life as duty, with a side serving of enjoyment when there is enough leftover time or resources.

But maybe the key to changing ourselves is not in the actions, but in the attitude. 

The ability to laugh at, to be excited by, and to embrace the failures that are an inevitable part of the journey might be the key to a more enriching life.

Worst case, even if the fun of failure never leads to anything, at least you had some fun along the way.

In the best case, a more lighthearted approach to challenges and upsets helps you see the valuable lessons that are hidden inside.

Either way, life is more interesting and enriching if you choose to see the fun in your failures.

As I asked in the beginning, have you ever had fun failing at something?

If not, perhaps it’s time to give it a try.