Playing to Win or Not to Lose?

In 2003, I started playing poker.

At the beginning, I wanted to be one of those guys playing in the big tournaments they show on ESPN, wearing my sunglasses upside-down on my visor, and throwing around money like it was nothing.

So I hired a coach to help me with that.

He came highly recommended. Good tournament record. Lots of experience.

The first time we spoke, I told him about a specific issue - as the tournament would get into the stages where players were actually winning money, it always seemed like my chips were slowly bleeding away instead of growing. Which meant that a) I was frequently winning NO money, and b) when I did win money, I wasn't even close to winning the whole tournament, where the payouts to the top few players tend to be disproportionately large.

I'd read all the books on optimal strategy and followed them to a T. Still, this issue persisted.

After we spoke about the specific issue, we agreed I'd play an online tournament with him coaching me through it. I'd tell him my hand, he'd have me play it a certain way.

And so it went. I got to the point in the tournament where I was close to winning some money, and my chips are bleeding away. "Nope, can't play that hand." "Nope, not this one either." It was EXACTLY what I'd been doing already.

Then, I thought to myself, "What the fuck is this guy doing? He's not playing to win, he's playing to not lose!"

Next thought: "Oh, shit, I'm doing that, too!"

I was eliminated from that tournament in 30th place, and the top 27 finishers got paid.

We never had another session.


It's an easy trap to fall into.

Graduate college, get a job, then a promotion. Buy a house and a nice car or two. Get married, have kids. Maybe another promotion. Then one day you're 38, you're barely sleeping, and you can see your dreams slipping away - but you just can't afford to take the chance on yourself. It's safer to stay where you're at, ride things out, and hope for a better day to come along.

Or maybe it goes like this, instead:

Start a business. Spend years of your life building it. The best years. Make it profitable. Make it prestigious. Make yourself irreplaceable. But something starts gnawing at you. It's the business. It's boring you. Draining the ever-loving life out of you. But can you risk the business you have for the one you want?

These are reasonable paths. Nothing morally wrong with them. Society will laud you for taking them.

There are a million other paths just like these.

But they all lead to the same place. And it's not somewhere you want to go.


Playing to not lose, as you might have guessed, often leads to what we experience as a losing outcome.

If it's poker, it means almost making money. In a relationship, it means the relationship stagnates, or continues in whatever its current undesirable form is. For a career, you're looking at burnout. A business, burnout or bankruptcy.

All you have to do is play to win.

Which is to say, go for what you REALLY want. Not the thing you think you're supposed to want. What you REALLY want.

It means you put time and attention on being honest with yourself about that. Getting clear on what it takes. Committing yourself to that path.

There are risks, too. 

You might lose money in the poker tournament. Get dumped. Be fired by your boss. Your company might still go under.

And you've got a fighting chance.

More importantly, you will feel ALIVE again.

Are you willing to take that chance?


A couple weeks later, I hired a new coach. I'm not exactly one to quit on something I want.

The first time I spoke with this coach, we talked about the mental game. He said we weren't going to worry too much about cards, that we were going to pay special attention to my opponents.

During hands, he'd ask me what my instinct was - how did I want to play the hand? When I started to feel more tentative, he told me something I'd never forget:

"In a tournament, there are conservators and accumulators. The conservators win some chips and do their best to never let them go. The accumulators never stop trying to win chips. Accumulators win tournaments."

What I heard was: Accumulators play to win. Conservators wait it out.

I didn't win the tournament that day. But I won one the next day. And then a few more not long after that. I never looked back.

Remember - YOU get to choose how you play the game - career, business, relationships, all of it. Choose wisely.

Love, MFH

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