Need Help Deciding? Bet On It!

5000 feet above the runaway, my plane throttled up into the pitch-black sky. Our final destination had been changed to San Francisco Airport, where we had just departed. At four in the morning, I stumbled into an airport hotel room, exhausted after spending the weekend with my friends in Vegas.

One year later, we were off to Sin City again, but this time, I wasn’t taking any chances. I switched airlines and booked a direct flight instead of a layover.

“No way I was getting delayed for a second time.”

I was wrong.

On the day of our departure, we were graced with the rare occurrence of rain, which set off a chain of flight delays and cancellations. I watched one by one as my friends waved goodbye and hopped on their plane. If they could make it home, I hoped that I could too. It was then I discovered that my flight was delayed another 2 hours. I wouldn’t be leaving until midnight.

“Oh no, it was happening again. Why me?”

Thinking In Bets: A Quick Summary

Four days prior, I opened a book on the flight to Vegas titled Thinking In Bets.

To make better decisions, we need to understand 1) the different outcomes possible and 2) which factors contribute to each outcome. With that, we should be able to make the best decision with the best odds hopefully to achieve the ideal outcome.

I tried to apply this idea as I gambled in Vegas but unfortunately struck out. However, the true test revealed itself on the last day. Now back to the airport.

Should I Stay Or Should I Go?

After learning my flight was delayed for 3 hours, I was ready to call it quits for the night. I knew the outcome. I’d hop on the plane, returning to the airport a few hours later. If I had left now, I could get some rest before flying out the next day.

As I walked towards the exit, a question popped into my mind.

Honestly, I wasn’t sure. I didn’t know enough about the situation. It was time to figure out the facts.

One hour later, I had some new information on hand. Below is a summary of my previous experiences plus insights from a gate agent.

• One year ago, my flight could not land due to midnight fog, forcing the plane to turn around.

• Tonight, several flights were canceled, including all three to San Francisco and one to Los Angeles.

• Almost all of the departing flights in Vegas were delayed due to bad weather.

• However, planes left shortly after they arrived.

• My flight was the last flight to San Luis Obispo that night.

• The fog situation in San Luis Obispo was subject to change, but all prior flights had landed successfully.

• If my flight could not land, it was unsure where the plane would be re-routed.

• The next flight out of Vegas was the following evening at 8 pm.

With this information, my decision was clear. In my situation, what would you do?

So Did Kalen Make It Home?

At 1 am, I locked the door behind me as I let out a long sigh. I kicked off my shoes, took a hot shower, and rolled myself into bed. As I drifted off to sleep, only one thought was on my mind, “I finally made it… I’m home”.

When the flight got delayed, my mind made a quick estimate of the potential outcomes.

• Flight leaving on time (0%)

• Flight being delayed (100%)

• Flight making a round trip in the air (100%)

It’s clear that some errors were made above, but why? Was it because of raw emotions or false assumptions?

The fundamental flaw in my thinking was trying to make a decision based on the past as opposed to the future. I was betting on the certainty of what had happened instead of the possibility of what could happen.

Based on the information above, let’s instead calculate the odds as bets on the future.

• Flight leaving at a delayed time (65%)

• Flight being delayed further (25%)

• Flight being cancelled (7%)

• Flight making a round trip in the air (3%)

• Flying out the next day (???)

If I had left the airport, I would have eliminated the most likely outcome of going home just to roll the dice again the following day.

I was terrified of being wrong again. Thankfully, everything worked out as I hoped, but what if it didn’t?

Would I have been devastated?

Definitely.

Would I have blamed myself for making the wrong decision?

Not at all.

The Decisions That Really Matter

So, here are two lessons from my two trips to Vegas.

When the odds are stacked against you, double down on the things you can control.

“The world was out to get me.”

It wasn’t fair to be delayed multiple times, but that was out of my control.

At that moment, all I could bet on was me. My curiosity to discover all the facts. My courage to stick around despite the bad situation. And finally, my empathy towards others, who had no control of the situation.

Instead of folding immediately, you can choose to play the best hand with the cards you were dealt.

The game of life isn’t defined by perfect outcomes, but instead from potential possibilities.

Life is so much more than the black-and-white outcomes of success and failure. Most decisions often have low stakes and can be fixed. Instead of spending time on every little decision, we should ask ourselves about the ones that truly matter.

As we wrap up, I’ll leave you with this question.

“What’s your game?”

The game of financial freedom? Personal happiness? Lifelong learning?

That’s the decision that matters most.

So, take a look at the life you live. Are you playing the game of life that your past and present selves would be proud of? Or maybe there’s another path with more favorable odds and opportunities?

The right answer? You decide.

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As part of our community, we would love to hear what thinking in bets means to you. When was the last time you’ve bet on odds? What happened? Feel free to share your story in the comments.

Discover Thinking In Bets in Life

• Learn firsthand about the Thinking In Bets mindset from professional poker player and author Annie Duke

• Another key to decision-making is understanding the return on investment for each outcome. Check out my previous article, Investing In The Ultimate Opportunity — Life

• What are the odds of being struck by lightning? Or becoming a millionaire? This article from Stacker has all of the answers and more!

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