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Who to Marry, Work With, & Befriend

Linda Vasquez: I know he made you a promise, but circumstances have changed.

Francis Underwood: The nature of promises, Linda, is that they remain immune to changing circumstances.

— House of Cards, Season 1: Chapter 1 (2013)
package in front of a closed door

We wrote Why You Should Plan a Heist four years ago, in 2018.

Friends and family have told me it has influenced who they let into their life. Since they found it useful and it has come up multiple times lately, I wanted to revisit it and focus only on that part.

The idea is to use a heist as a metaphor for high-stakes, emotional, situations.

You are planning a heist and you need the door to the building to explode at 10:00am next Monday.

There is a single question that ultimately matters in picking the person for this position: Is the door going to blow up at 10:00am next Monday?

If, for any reason, the door does not explode at 10:00am, you are dead or in prison. There is no such thing as a good excuse.

This question will filter out more than 99% of all people you will ever meet because what it is really asking is:

  • Can I trust this person to raise our kids?
  • Can this person get the deal closed by the deadline?
  • Will this person cheat on me?
  • Would I start a company with this person?
  • Am I going to be proud of this person or embarrassed?
  • If I make a non-refundable deposit for the trip, will everyone in the group chat send me their share?

In other words: Is this person reliable?

Two traits are absolutely necessary.

The person must be:

  1. Capable
  2. Trustworthy

You can usually find one or the other, but as the stakes get higher, it is harder to find someone with both.

Low stakes: I am traveling alone at the airport and I ask someone to watch my bag while I use the restroom. Everyone I have ever asked to do that has been both capable and trustworthy.

High stakes: At work, people help me write 40-page memos for loan requests. There are a lot of numbers and information. If any of the information or numbers are wrong, it damages my reputation and credibility. It can directly impact my income. It is significantly harder to pass this test.

This is why employers say it is hard to find good people. (Spoiler: Good people are EXPENSIVE.)

First, you need someone who knows how to do it. Someone may be ride-or-die loyal, but you can only put your life in their hands if they have the qualities you are looking for.

You need someone who knows how to get things done. You want your spouse to have certain qualities. You want your friends to have your back.

This is why a popular CEO said the number one quality he looked for in a wife was resourcefulness: “I wanted a wife who could get me out of a third-world prison.”

You are looking for someone who understands this, and has the flexibility to adapt to problems because something is guaranteed to go wrong.

If I get cancer, I want someone who opens up WebMD, not Raya.

If a friend owes you money, do you have to remind them twice, or do they Venmo you before you ever have to say something?

Trustworthiness is hard. Some people are trustworthy in some situations, and not others. Some people are trustworthy, to a point. That is why the heist framework is useful. It tests the depth and strength of the relationship.

It is one of the ultimate compliments and it can be applied to everyone from the barista to the Chairman of the Federal Reserve. Is the order going to be right? Are you going to change interest rates the right amount at the right time?

Most people in your life will be on a continuum of capability and trustworthiness. Your friend at work may not tell anyone the secret you told him, but is he going to be groggy or hungover the day of the heist?

Obviously, asking the question of myself is equally useful. Can people rely on me to blow the door up at 10:00am?

In any relationship (romantic, platonic, employment), I want the person to know that the door is going to blow up at 10:00am. This means I am increasingly careful with my commitments in setting expectations and increasingly transparent with my capabilities. Here is what I can do. Here is what I can’t do.

Two interesting interpretations of all this: Nothing is a heist, or everything is a heist.

You can say, “Okay, obviously this is an over-the-top example to avoid letting losers into you life. In reality, if I text them I’d be there at 10:00, and I get there at 10:10, who cares?”

Or, you can say, “Everything is a heist. Almost everything you do creates an expectation with someone else. Are you and the people in your life living up to the expectations you implicitly and explicitly set with each other?”

See also:

Thanks to James Bunch, Suzanna V. Wood, Sanam Makhani, and Garrett Gravesen for reading drafts of this.

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