Wealth, Power, and Character

In your life and career, you will have multiple opportunities to make high leverage relationship decisions.

Whom will you choose as your boss?

With whom will you partner to start a company?

Whom will you marry?

For many of us, the number of times we will make these decisions in a lifetime can be counted on our own two hands. Strategically choosing a superstar boss to build your career behind can make or break your career. I have had one superstar boss in the past who put my career in a different orbit. My current boss is a rock star.

Picking the well-matched business partner can make or break a startup. Choosing the right spouse has an enormous impact on your life.

In these high leverage decisions, I urge you to consider the other person’s character. I define someone’s character as the set of values they attempt to live by (their personal “code”) and the level of integrity they have between their intentions and their actions (e.g., do they actually follow their own “code”).

Until you understand someone’s character, you do not really know them.

If you don’t really know them, it’s difficult to make a well-informed decision about whether or not to develop a potential multi-decade relationship with them.

It’s my firm belief that character gets revealed under extreme situations.

When someone obtains an incredible level of wealth, power, and material success, their true character gets revealed. A person who has more power than they ever imagined, are they still kind and respectful to you (because that’s in their character)?

Or do they conveniently forget about you because you’re not “important” enough to them anymore?

When someone loses everything, their true character gets revealed as well.

It’s easy to “do the right thing” when everything is going well. But it’s far harder under the opposite circumstances. When the starving man refuses to steal food even though he knows nobody will catch him, that says something about his character.

When you understand someone’s character, you are much better able to predict and rely on their behavior under a much wider set of circumstances. It’s one thing to pick a business partner because he believes in hard work when things are going well. You might choose differently if you discover that same work ethic disappears in the face of discouraging circumstances.

In practice, it’s challenging to see people across a wide range of circumstances. In most cases, you will never have perfect information about the other person. This isn’t a problem in and of itself… IF you realize that you lack this knowledge.

What’s dangerous is when you lack information about the other person, and you simply assume favorable attributes because life would be so much simpler if that were the case.

It is more prudent to structure what you have at stake to be proportional to how well you know the other person. Always safer to pick a business partner you’ve worked with for over 10 years than it is someone you met at a business function last week. It’s less risky to go “all in” and follow your previous boss to a new company if you’ve worked with him for a long time and have seen him operate under a wide range of circumstances).

It is wiser to marry someone after you’ve dated for many years and seen how they behave across the ups and downs of life, than to marry someone after the first date.

You will benefit associating with people whose character you respect and admire — a person whose values you find compatible with yours.

When you don’t make time to get to know someone’s character or you choose to ignore their character, there are nearly always negative consequences to these choices.

Choose wisely. I urge you to watch the character of Omar Little from the series “The Wire“. His ideals and concept of code is inspiring.