The Pain Portfolio: Investing in Challenges for a Fulfilling Life

Most people’s idea of success is wrong. Success is not measured by the things we have gained, but the sacrifices we have made.

In the 1990s, a study called Adult Literacy in America was conducted. They proved that finding a literate audience for a political argument was difficult. Majority of Americans over 15 lacked basic skills to evaluate ideas and form judgments. 

According to the U.S. Education Department, 90 million Americans, that’s 27% of the population, could not write a letter, navigate a bus schedule, or do basic addition or subtraction. 30 million, or 9% of the US population, was judged to be so incompetent they couldn’t even respond to the question.

Over 30 years later, do you think this number is smaller or bigger today?

One of the downfalls in modern education is learned helplessness. You’re taught as a young kid that someone always has the right answer. Most people apply this to everyday circumstances decades after they’ve left school.

They believe they are incapable of learning a new skill, adopting a new mindset, or improving on an area of weakness. They’re not incapable, they just don’t want to go through the pain of being a beginner again. Only when the pain of disgust becomes more than their pain of change do they attempt to do something about it (which is rare to happen).

This is your competition...

Why seeking pain is important.

There’s now a lot of data on a part of our brain called the anterior midcingulate cortex. This area of your brain grows whenever you do something that you don’t want to do.

Neuroscientists believe it’s the seat of willpower. It’s the part of your brain that is responsible for the will to live. Andrew Huberman said this part of the brain will grow only when you continue to face and conquer challenges. It will only grow with pain. 

The research found that this area was bigger in athletes and smaller in obese people. But when someone who’s obese diets, it grows bigger.

When you do anything you don’t want to do, it grows. You need pain in your activities. Overcoming the resistance you have towards certain activities will increase this part of your brain.

An interesting fact came out of the studies they conducted on individuals:

For people that live a very long time, this area keeps its size.

Your pain portfolio is more important than your resume.

The interesting things about life come from your portfolio of pain. The challenges you overcame are more important than your accomplishments.

You have no problem paying into your investment portfolio, but hate when you have to suffer in order to invest in your pain portfolio. Investments feel like a fee while the challenge you face feels closer to a fine. You pay for things where the price tags may not be immediately obvious.

Pain looks different if you start to view them as a fee instead of a fine. The challenges become ingrained in your personal hero’s journey. The hardest things you’ve overcome are what you’re the most proud of. They’re what people can relate to.

Most people shy away from pain because they fail to understand the role that the end of history illusion plays in their life. We believe we’re already the person we’re meant to become and that the next 10 years will result in minimal change, least of all change that requires suffering.

All personal progress is a by-product of having a large pain portfolio.

Your stories, parables, and life lessons are the collection of these painful moments. Naval Ravikant says “your real resume is just a catalog of all your suffering.” This catalog is the true testament to who you are.

Painful events tell you more than the achievements – as Mike Tyson said “everyone has a plan till they get punched in the face.” The hard stuff gives you meaning.

Instead of avoiding pain, look at it as moments of truth, or periods of wisdom, you’re developing for a better future.

How to know where to invest in your pain portfolio 

Procrastination is the result of our present bias taking over. We value the short-term more than the future. Combine this with the end of history illusion and it’s a recipe for inaction.

As time progresses, regret from procrastination accumulates because your future self has greater struggles. We’re constantly pawning them off challenges to ourselves in the future. Delaying the investment we need to make into our pain portfolios.

You must keep these future regrets front of mind and discount the future value of progress back to today. In 10 years, will you regret this action (or not doing it)?

Regret discounting helps you put your present efforts into perspective and overcome your present bias. 

Before he started Amazon, Jeff Bezos had a prestigious well paying job. Everyone told him he was crazy for wanting to leave it to sell books on the internet (something most VC investors didn’t even know much about at the time). To Bezos, the decision was a no brainer. There was only one way he would minimize the amount of regret he had in the future. Try to start a company. This later became his regret minimization framework.

With regret discounting you’re trying to weigh if your actions today will have a net positive or negative for your future self. You have to choose if it’s better to spend the time on an activity today or at another time in the future.

Most people will constantly borrow from their future self. Each time a loan is taken out (with interest) from your pain portfolio that eventually you’ll have to pay back. 

You wonder why so many people are never fulfilled with their current situation. They avoid the pain needed to get them to the next level.

  1. The study on literacy, Adult Literacy in America, referenced:
  2. Andrew Huberman on the anterior midcingulate cortex growing with pain:
  3. JORGENSON, E. (2022) in Almanack of naval ravikant: A guide to wealth and happiness. S.l.: HARPERBUSINESS, p. 89.
  4. Housel, M. (2023) in The Psychology of Money: Timeless lessons on wealth, greed, and happiness. Petersfield, UK: Harriman House Publishing, pp. 151–162.
  5. Jeff Bezo's regret minimzation framework:
  6. Weinberg, G. (2019) in Super thinking. Penguin USA, p. 87.

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