Is Failure Actually Needed to Succeed?

From 1990-1995, when i first was writing, I wrote about 50 stories and 4-5 novels.

WITH EVERY STORY, I would send to 50+ literary journals. I got rejected by every single on on every single story. 2500 rejections in five years.

WITH EVERY NOVEL, I would send to every publisher and agent. 100% rejection. About 1,000 rejections.

It wasn't until I was writing almost every day for 12 years that I finally got published and paid for it. And I think I wasn't a good writer for the first 15 years of writing every day.

I now know what was making me fail, but I didn't have the talent to see that in 1990. Or 1995. Or 2005.

I always say my first business was Reset, a company that made websites and was a success. Although I made many many mistakes at it. But I actually had two or three companies I started beforehand that were failures. And I've had many failures (and a few successes since). It's painful to fail. Why did I choose a life like that?

I started trading in 1998 but professionally trading in 2001 (meaning: other people's money as well as my own).

But I lost horribly in 2001. To the point that I became broke. So painful. Went from millions to zero and had to start from scratch.

It wasn't until 2004 that I felt decent at trading. Maybe 2003. But that's years of failed trades. I knew a lot about stocks and investing for the long-term but I only got personal satisfaction from daytrading. A situation with very asymmetrical returns.

It wasn't until 2010 that I finally felt like I was a good investor and daytrader. My track record since then has been incredible but is still filled with tons of frustrations and failures. Why did I choose to try and making a living in such a painful area.

I've played a lot of poker. One year, 1998-1999, I played for 365 nights from 8pm to 4am every night. I even got a house in Atlantic City to play every weekend there. Often for 36 straight hours each weekend.

When you win in poker, it feels great. When you lose, it's the worst feeling of all. Why not collect stamps?

I was a losing player for the first six months.

But it's a skill that stuck. Despite the increase in poker theory in the past 20 years, I played a tournament a few weeks ago and came in 3rd out of 100. First tournament in 23 years for me.

Nevertheless, some nights I'd stumble home from poker and just feel like dying inside because of the losses I took, particularly as I was getting better

I worked so hard at this for six years. Six years, 4-6 nights a week, sometimes two shows a night. And all day watching comedy videos, interviewing comedians, reading about comedians, and writing material.

So many failures, particularly in the beginning.

Imagine literally standing up in front of a room filled with 100 strangers and trying to make them laugh and all you hear is...silence. Or even booing. This didn't happen a lot (the booing part) but the silence part happened quite a bit, particularly in the first few YEARS. YEARS! Ugh. Why put yourself through that?

Why did I do it? So much pain.

And yet, the nights when people were rolling on the ground laughing were incredible.

Still, is that better than trimming bonsai trees and the satisfaction that can result from that?

I ended up traveling all over the world doing comedy with some of the best performers ever. But even in the last year of me doing comedy I had at least one experience that was incredibly painful.

I've played tournament chess since I was 17. I hit 2200 rating (which is the Master title) in 1997. I was alwasy good. When I first started I was already good.

But...when you play, you pour everything into a game. Particularly a slow tournament game. And when I lost even one game I'd be so upset I'd drop out of the tournament and skip school. I was so angry at myself.

I stopped playing for 25 years. I had hit the master title and it was too painful.

Now, this past year, I've started again. WHAT A DRAG IT IS!

On the one hand I've had my greatest successes. I've beaten the highest rated players I've ever beaten and it's happened since I got back into it.

But on the other hand, maybe its true that I can't make a full comeback because of my age. Just had my worst tournament EVER! Ever!

Why do I put myself in these positions? Why not a regular hobby? Would save time, money, and emotional pain?

I don't ride horses. But when I was a kid, I spent one summer riding horses. I really enjoyed it and I felt like I had improved a lot.

At the end of the summer, the camp offered a prize to the most improved horseback rider. I thought I would get it. I didn't. I remember this kid named Michael got it.

The counselor came up to me afterwards and said, "Listen, I know you thought you would get it but I have to tell you why I gave it to Michael."

Michael had fallen off a horse once and immediately got back on it. "But I never fell off a horse," I said.

"I know," he said, "which is why it was tough to decide. But getting back on the horse right after falling off it, is the hardest skill to have in horseback riding. So I had to give it to Michael."

And that was that.