How to Handle Tough Decisions

Welcome to this week’s edition of In Position!

Let’s begin with a hand puzzle:

$5/$10 NLHE 9-max.

The cutoff opens to $30. Others fold, you call in the big blind with A♦️T♥️.

Flop: Q♥️6♦️5♦️ ($65) You check, CO bets $35, you call. Turn: A♥️ ($135)

You check, CO bets $100, you call. River: 9♦️ ($335) You check, CO bets $250. You…?

Think about it carefully, and then keep reading to find out my answer.

Tough Decisions

An interesting discussion came up during a recent session in my coaching program, Beyond the Game. One of our members presented the group with a very complex, difficult life decision he needed to make soon.

We all agreed that his position wasn’t enviable: Either choice could be one he might end up regretting.

We discussed it for a long time. Many people weighed in.

Both options were advocated for, and there wasn’t a clear consensus. Then, one of our captains suggested applying poker wisdom to the situation: Why not just flip a coin?

Before sharing more about this, I want to discuss how it reminded me of a key concept in poker – a concept that applies to many other areas of life and business.

It Doesn’t Matter

When most people post a hand history and ask for advice on poker forums or a community chat, it’s usually a rare, big river spot like our hand above. And that makes sense! The bigger the pot and the tougher the decision, the more likely it is to stand out to you after your session.

But sending select hands to coaches, or sharing them with a study group, is rarely the best way to improve. If you think the hand is close enough to ask about, the options are probably similar in expected value.

If a decision feels like a 53-47 spot, it won’t impact your bottom line all that much – especially when it’s one of those hard, agonizing river spots that isn’t going to repeat itself very often.

Think about it this way: If you're a chef, sure, perfecting a soufflé is cool. But how often are you making one? What really impacts your success — and your bottom line — is mastering the everyday stuff: chopping, seasoning, cooking meats just right.

If you review a session that you’ve played, there are usually one or two exciting soufflés in there. For most people, these tend to garner a disproportionate amount of study time.

What you should instead focus on are the hundreds of spots that feel more mundane: The things a master chef repeats tens of thousands of times over their career.

What to Focus On

Some examples of the types of decisions to focus on and the questions to ask yourself:

$5/$10 NLHE. UTG opens to $30. Others fold, you call in the big blind.

Flop: 7♠️5♠️4♦️($65)

Do you lead with any hands? What hands are your best check-raising candidates?

or:

You open to $30 from the button, SB folds, and the big blind calls.

Flop: K♦️8♣️5♣️ ($65)
BB checks.

Do you c-bet with all your hands? With most? What sizing do you use? Do you want to split into multiple bet-sizes on flop? And if so, which hands types prefer to bet which size?

or:

The button opens to $30. You 3-bet to $115 from the small blind. BB folds and the button calls.

Flop: Q♠️J♥️6♠️ ($240)

What does your flop plan look like? How do you balance a betting range with your check-call, check-raise, and check-fold ranges?

And so on.

These are situations that you come across day in and day out. It’s easy to overlook them because a c-bet decision in an 6.5BB pot feels so unexciting – you probably don’t even care much whether you win or lose that pot. Yet the better decisions you make in the early streets, the less likely you are to end up in that difficult river spot in the first place!

Give Us a Shot Clock!

An interesting phenomenon I’ve observed in poker players is that, despite being able to make complex decisions in seconds, some of us can agonize over untimed decisions away from the table.

I think it’s our ability to see and consider so many factors, and our desire to optimize.

The other day, I walked outside with a trash bag in one hand and the recycling in the other. In the five seconds before I approached the bins, I thought:

If I open the recycling bin and it’s full, I’ll have to put the recycling in the trash can.

If I open the trash can and it’s full, I can’t put the trash in the recycling bin.

If I open the trash first, and it’s not full, then I open the recycling bin and it’s full, I’ll have to open the trash can again to put the recycling there.

Three opens.

So I should open the recycling bin first because then I’ll only be opening each bin once, no matter which, if any, is full.

Now, this decision didn’t matter, and I knew it, but this is just how I’m programmed to think now – and many other weirdo poker players are the same!

When given unlimited time and an actually important decision, we notice so many things that might be worth considering!

Real World Flips

It took years to train myself not to fall victim to this (as often) in my businesses. Like in gambling, the more +EV bets you can make, the better. Spending countless hours to make sure you’ve thought of everything means costing yourself the opportunity to make many more +EV bets.

Generally, I don’t advocate making huge decisions by flipping a coin, and our BTG captain from the opening story wasn’t exactly suggesting that either.

Simply acknowledging that the decision was close enough to leave to fate in situations like these may help ease some of the perceived gravity of the decision. And, as he suggested, our hero might find clarity through the exercise.

When you flip a coin for a meaningful situation, you may notice yourself very clearly rooting for an outcome.

And there you have it: Your answer.

Good luck winning those flips!

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The Art of Storytelling