Fail doing what you want to do

You can live with that

Make sure you fail doing exactly what you want to do. That, you can live with.

Can someone hand me a mic so I can drop it?

Unlike most advice swirling around in the culture, this bit caught my eye and deserves some further exploration.

Back in the dark ages (1989), David Letterman shared this sage advice with Jerry Seinfeld before he started filming a silly little show about nothing.

This goes counter to conventional wisdom that convinces us to worship at the altar of success. Which is why I loved it.

Is it true? Who cares.

Is it useful? Ah, now that’s a better question.

Let’s see.

I went deep down the Jerry Seinfeld rabbit hole over the past few weeks, and in several interviews he talks about how his show wasn’t very popular for the first three or four seasons. But he didn’t care.

He never expected it to be a massive hit. He just wanted to make a show he wished already existed. And to his surprise, it went on to be arguably the best sitcom in history.

Actually, there isn’t much to argue about.

But success was never the goal. If he failed, he was going to fail doing exactly what he wanted to do.

And I think this is applicable to any project you or I undertake.

For example, I’d rather fail at this whole writing experiment I’ve been conducting for the past two years doing it exactly as I see fit.

That, I can live with.

Early on, writing daily felt like pushing a wheelbarrow full of bricks up a steep muddy hill with gail force winds blowing in my face.

But I loved it.

Not because of any minor success I claim to have. But rather because I didn’t give a damn what the outcome would be.

I still haven’t earned a single penny from writing.

I still haven’t gone viral on the front page of Reddit.

I still haven’t attracted an audience of millions.

In other words, I’m still failing big time right?

Rubbish.

If any of the words I’ve written have been a joy to read, that’s great.

If not, that’s great too.

I’m just going to keep showing up and doing my thing.

Much like Jerry did with Seinfeld.

It’s so tempting to think that success is the ultimate goal. And failure must be avoided like the plague. But success and failure are so subjective. Nobody can agree on what they mean.

Success to me might be failure to you. And vice versa.

I’ve stumbled upon a strange realization — failure can be fun if you’re failing while staying true to the only person that matters — yourself.

As I see it, it really comes down to finding that activity you do solely for the joy of doing it. Oblivious to success or failure.

If you find yourself wanting to throw in the towel after a few failures, that’s simply not your thing.

Drop it and move on.

But if you find yourself continuing to show up, anxious to take another crack at it, and regardless of any outside criticism or praise, you’ve found your thing.

What a blessing.

It took me twenty-nine years to find out that writing was my thing.

Because that was the only activity that I didn’t mind failing at over and over and over again as long as I was doing it the way I wanted.

A helpful question to ask yourself is, “would I still be doing this if I was the last human alive?”

If not, then why are you doing it at all?

For a pat on the back from strangers? For an atta boy from your friends? For recognition from your idols?

What if those never come?

Is that going to be a sufficient reason to get you to push your wheelbarrow up the hill?

I’ll leave you with one final question to ponder — would you rather succeed wildly doing what others told you to do or fail spectacularly doing exactly what you want to do?

Choose wisely my friend.

Questions? Concerns? Complaints? Please leave a comment below.