Some people have all the luck.

You know the type. Swanning about with nary a care, never seeming to break a sweat. And yet the opportunities that the rest of us could only dream of just fall into their laps. As if by magic. Never a misstep, never an embarrassment, never a very public failure. A charmed life.

I call them Jerry Seinfelds.

I can’t help but look at them like the beleaguered, long-suffering Elaine and think “One of these days, something terrible is going to happen to you. It HAS to.”

And I can just imagine the casual confidence in the response. The swift, arrogant dismissal:

“No, I’m gonna be just fine.”

But the thing about luck is – sooner or later – it runs out. 

For all of us.

We don’t really live in sitcom worlds where everything works out for the sake of the status quo. And not even Jerry Seinfeld is “Jerry Seinfeld” in real life.

All of us make mistakes. We all learn harsh lessons. We all fuck up. 

Even the Jerry Seinfelds of the world.

And it’s not out of ill-will or jealousy that I say this. As painful as failure can be in the moment, I think it’s a wonderful thing. A vital thing.

I’d argue that trying something new, messing it up royally, looking back, working out what went wrong and why, and then – and this is the crucial part – dusting ourselves off and trying again, is the best possible way to learn something. Sure, you’ll feel like an idiot for a while. Maybe others will see you messing up and you’ll be mortified. It will sting. But that doesn’t matter: learning the hard way is, in many things, the only way to learn.

Because listen here, Jerry: you learn nothing from getting it right the first time by pure chance.

Lucked your way into doing the thing? Great. But suddenly need to recreate it, or teach someone else, or do the same thing again but slightly different? Better cross your fingers. Because if you just got lucky the first time, then you don’t really know how to do it at all. 

Maybe I’m underestimating your rub of the green. 

Maybe you will be able to recreate it. 

But even if you do make it work, you won’t know why it works. You won’t have the siren going off in your head saying “hang on, have I double checked X and Y?” Failure breeds caution. Once bitten, twice shy, and all that. Keep riding your luck and it will desert you, eventually. No one is that lucky all the time.

So next time you encounter a Jerry Seinfeld type, consider this: maybe they just messed up so hard and so often early on in life that they’ve already learned all the lessons they needed to make it look so effortless now.

You don’t need luck. You just need to pay attention while you mess up.

Don’t be afraid of failing. It’s the best way to learn something new. You need to fail at something in order to get good at it.

Just don’t rub it in our faces when you join the Jerry Seinfelds of this world.


Everybody makes mistakes (and that’s great).

  1. I Learned the Hard Way – Sharon Jones & The Dap-Kings
  2. Giving Up – Durand Jones & The Indications
  3.  Slow Education – Silver Jews
  4. Had To Hear – Real Estate
  5. Falling and Laughing – Orange Juice
  6. Heard You Want to Beat Me Up – The Strange Boys
  7. Mistake – Vivian Girls
  8. Freudian Slips – Big Trouble
  9. Do No Wrong – Des Demonas
  10. This Mess We’re In – PJ Harvey, Thom Yorke
  11. You Can Fall – Broadcast
  12. Something’s Gone Wrong Again – Buzzcocks
  13. Slow Learner – Viagra Boys
  14. History Repeats – Brittany Howard
  15. Right – David Bowie
  16. The Planner’s Dream Goes Wrong (Demo) – The Jam
  17. Break My Stride – Matthew Wilder
  18. I Get Along Without You Very Well (Except Sometimes) – Chet Baker
  19. Time – Angelo De Augustine
  20. Some Days You Just Can’t Win – Ultimate Spinach
  21. Just Can’t Win – Lee Fields & The Expressions
  22. You Made Us Change – Ephemerals
  23. I Have Learned To Do Without You – Mavis Staples
  24. I Learned It all the Hard Way (live) – Howard Tate

For more thoughts on failure, try my post on Sufjan Stevens’ Illinois.