Making decisions is tough. From the wardrobe to the boardroom, we all struggle when it comes to choosing the right path ahead. Ever wonder why Mark Zuckerberg wears the same color clothes? To avoid unnecessary decisions.

Just think about it: how much time is wasted each day deciding what to wear, what to eat, or how to word that four-line email to a colleague? And the worst part is, once we’ve made that decision, we often regret it. “Do these clothes match?” “Did I come off too aggressively?” The reality is that making decisions is tough, and living with them is even tougher.

But as is the case with any skill in life, some of us are better than others at making decisions, or at least, living with them once they’ve been made. Thankfully, we can all improve our decision-making ability, and leverage this ability for long-term success.

To learn what it takes to hone this skill, IVY hosted Al Pittampalli, an author and business consultant who has worked with a number of high-profile companies, for a special Ideas Night. He offered us his insights on making decisions, navigating choice, and living with the consequences through two powerful examples: poker and apartment hunting. Below is an edited transcript of that conversation.

How do you make the right decisions?

“Decisions we will make — no matter how much we want to get them right — I’m sorry to break it to you,  but we’re going to get them wrong. The decision-maker’s creed says nothing about guaranteeing the rightness of your decision, right? No matter how many people you talk to, no matter how much you want accuracy, there will always be a flaw.

When did you realize that there is always a flaw?

“My friend Blake, who’s a professional poker player, taught me this lesson. (Recalls) I’m playing with him, I don’t have a lot of chips left, I have this amazing hand, and I decide to go all in; I lose the hand. I am beating myself up, I am frustrated and angry with myself, and said, ‘what a stupid move.’ Blake interrupts me and says, ‘That’s not a stupid move. That was the right move. You played the odds. That was a good decision.’

In poker, you can do everything right and still not end up with the right outcome. But that doesn’t mean you should change what you’re doing. That just means you need to play another hand. You see, amateur poker players play for this hand only, but the expert poker players play the long game. They know that they can never guarantee winning a hand, but over a course of a hundred hands, if they increase the probability of winning each hand, they will end up winning in the long term. That’s the best metaphor I know for how to approach decision-making.”

“You see, amateur poker players play for this hand only, but the expert poker players play the long game…that’s the best metaphor I know for how to approach decision making.”

When making decisions, how much do you consider trade-offs?

“The thing about trade-offs is you can’t have both. When you get more of one thing, you get less of the other, but when we don’t recognize this (and we often don’t), there’s lots of pain, and there’s lots of frustration. Who here has a great deal on a New York City apartment? It’s a trick question, don’t raise your hands. You’ll embarrass yourself. There is no such thing as a good deal in New York City. It’s such a competitive marketplace that nothing is either undervalued or overvalued. It’s just valued the way it’s supposed to be, right? So you see a place over here, it’s got beautiful location, but it’s got terrible size.”

What do you say to people who think they have “great deals”?

“I love how all my friends tell me that they have a great deal. My hobby is to kind of go and rain on their parade; go to their place and show them how it’s really a trade-off. One of my friends actually almost convinced me that he had a good deal in New York City. ‘You’ve got to see my place, it’s beautiful, it’s an amazing location.’ So, I went there and he was right. It was in a great location, he wasn’t paying a lot of rent. I expected to see a really small matchbox place, and lo and behold it wasn’t. I’m going through the rooms and thinking, ‘wow this place is amazingly big.’ It was beautiful, and it had nice fixtures. So I was like, ‘man maybe I’m wrong about this.’ That is, until I went into the kitchen and do a double take because he’s got a shower in the middle of it.

There’s one thing that we can learn from my imbecilic, shower-loving friend, which is that, there is a way to deal with trade-offs. You can’t beat the trade-off, but what you can do is identify what you’re willing to sacrifice because if you know what you’re willing to sacrifice, you can get more of what you want.”

Inquiring minds want to know…What advice would you give to people who are apartment hunting right now?

“My advice is to look for 5th-floor walk-ups. If you are able and don’t mind climbing five floors, you’re going to get a much better size, location, or something else. Find what you can live with. That’s the way you can deal with the trade-off.”

“Find what you can live with. That’s the way you can deal with the trade-off.”

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