Suck at Making Money? Maybe It’s Your Personality

Despite my efforts to get better, I've always sucked at making money. Now, based on personality research, I think it may be my wiring.


Key Points

  • Money-making is a skill: Anyone can get better at it, but some have natural gifts that make it come easy to them.
  • Those people’s brains are probably wired to get more pleasure from making money than others.
  • Those who enjoy it more will chase after it harder, which accelerates their skill development, so they have a natural advantage.
  • If you’re like me and don’t have this natural ability, accept it and work with what you’ve got, or consider working for someone who’s got the knack, which can pay better than trying to do so on your own.

As much as I like games and tend to be pretty good at them, there’s one I suck at despite giving it my all:

The money-making game. 

Put it this way: 

If I had put as much practice, patience, and perseverance into pretty much any other game—beach volleyball, chess, Twister, whatever—I’d perform at a kick-ass level by now. But when it comes to making money, I’m still a bum. 

So I’ve often wondered:

Why does the money-making game seem to come so easily to some people? And why not me?

Well, thanks to my research on personality, I now have a theory

Whether or not it’s true, it can improve your strategies for making money—and spending and investing it.

Consider this…

YouTube video

Financial Personality Theory

Earlier this year, I made a multi-month deep-dive into the science of personality and reemerged with this conclusion:

You have no control over your personality, so you’re best off working with it rather than fighting it. 

The most scientifically-supported personality framework is that of the Big Five “CANOE” traits

  • Conscientiousness
  • Agreeableness
  • Neuroticism
  • Openness to experience
  • Extraversion

Of those, two trains seem pertinent to money games:

Extraversion and neuroticism. 

According to scientist Daniel Nettle:

  • Extraversion is your brain’s sensitivity to positive emotion.
  • Neuroticism is your brain’s sensitivity to negative emotion.

My theory? 

  • Natural money-making ability = financial extraversion, your brain’s sensitivity to positive money flows. 
  • Natural money-spending inability = financial neuroticism, your brain’s sensitivity to negative money flows. 

One piece of evidence backing this theory:

Extraverts tend to be worse at holding onto their money, i.e., low on the financial neuroticism spectrum. 


Because they feel higher highs (though short-lived) from buying shoes they can’t afford or rounds of drinks for everyone at the bar.

In my case:

  • I’m financially introverted. I’m highly insensitive to the pleasures of making money, so I pursue it with the lusty vigor of a eunuch.
  • I’m financially neurotic. I’m super sensitive to unnecessary spending, so I tend toward unconventional engagement ring and bed purchase decisions.

What This Means

If my theory holds, the upshot is this:

Like with any other personality trait, quit fighting your financial wiring and learn to live with it—even use it to your advantage. 

For people like me who suck at the money-making game, that means to stop straining to become a money-magnet entrepreneur. I may be better off working for a financial extravert (i.e., getting a job), as they may pay me more money than I can make on my own. But I tried that

Another option?

Be happy with less. Keep being a poor entrepreneur, but lean harder on my financial neuroticism to compensate. That way, I can continue to enjoy the freedom of doing what I love.

Or maybe there’s another way to leverage your financial wiring. I’m starting to suspect I can take advantage of other parts of my personality to identify and invest in super financial extraverts so they make my chump change go cha-ching.

For more on this, watch my latest video. It’s only 6m47s long and people rave about my dance moves in it:

YouTube video

Thought Starters

  • 🙀 Feeling is for doing. (Financial) extroversion and neuroticism are examples of how your actions are motivated by emotion (study source). In what other ways might you improve decision-making by better understanding the source of emotions that drive your actions?
  • 🥤 What do you suck at? “The only way you can describe a human being truly is by describing his imperfections,” wrote storytelling legend Joseph Campbell. What imperfections can you hone in on to make your story a better one?
  • 💰 Money’s just a middleman, so skip it? The average American would pay $242k for 1 extra year of good health and values seeing a good friend regularly at $100k a year.
  • 🐜 Less ego, more savings? “One of the most powerful ways to increase your savings isn’t to raise your income. It’s to raise your humility.” – Morgan Housel
About the author

👋 I'm Chris. Everything you read on is my fault. This site is like a gym for your comfort zone, full of challenges to make your status quo sexier. Join my 'Consider This' newsletter for a fun new challenge every 10 days. Try it!

2 responses to “Suck at Making Money? Maybe It’s Your Personality”

  1. Tiffany Avatar

    Thank you for this article. I keep forgetting who I am, and coming back to it. It’s reassuring when even one person on the internet speaks the way I think and feel, and that is this article. I really appreciate it and wish you the best. Tiff from Connecticut

    1. Chris Avatar

      Thanks, Tiffany. Keep doing your thing!

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