Recently a long-lost friend contacted me out of the blue.

It was a pleasant exchange. Eleven years had gone by.

I was curious about what he had been up to, what the world had shown him. He had exciting stories.

Then we got around to me. I said I left medical administration to teach. Among other things, I raised money to build business programs. I was quite proud of my work.

However, all I got from my friend was “I always thought that you’d be a really successful businessman.”

In a way, that was a compliment.

I was already a successful businessman, but maybe he meant that I’d be at the next level. And in a way, it was a demotion.

I left a great-paying, prestigious role to teach high school and college courses. It was a conscious choice to choose legacy over money—and I don’t regret it. My students and the profession taught me a great deal about myself and humanity.

Who Are We Now?

Still, my friend kept probing me about what I could have done and the kind of money I could be making. In fact, all he talked about was money. Money and things: homes, cars, boats, travel. He wanted me to join him in a profession where that adds zero value to the world.

It was like we were having a high school level conversation, daydreaming about the so-called finer things in life. But these were immature dreams that didn’t matter much to me. I already bought a good house in a great city. I’ve already traveled to many cities I wanted to experience. I have everything I need, without all the excess.

I realized that I changed so much.

Though I’ve known it for some time, I never really talked about it to anyone. My whole life changed because my values changed. I valued education and improving society, so I became an educator. I also valued relationships with people more than my relationship with money. This was a huge change.

I used to stay up at night and read every book I could get my hands on about marketing or management. But in the past ten years, I’ve read more books about education and society. Money was and still is important to me.

Even to this day you can’t pry me away from a good business book. However, money and materialism is just one part of my portfolio life and life in general.

I don’t fault my friend for looking at my life as unsuccessful. That was his perception. He had his own ideas about how success is defined. I was just confused because in the grand scheme of things, I thought I was successful.

What Is Success?

Today, success to me is more about other people, not necessarily myself. As a result, my definition of success changed too.

I grew up.

I decided that materialistic wins come and go, but legacies are forever.

I didn’t want to be the person who died with the most toys, I wanted to be the person who died with a great legacy.

Anyone who has ever been a teacher can say that. They committed a near self-less act and tried to improve society in their own way. It doesn’t matter if they were brilliant or lousy teachers. Getting into the profession tells me that at least your heart was right.

No one gives up a lucrative profession or the potential thereof to become a teacher because of its social status and perks. Every teacher I know is over-worked and underpaid. Sixty-hour weeks are the norm and weekend work is a given.

Why do we do it?

Deep down we know that the other half of our paycheck comes in the form of student success years after they left the classroom.

But this isn’t about teachers. I feel the same way about any profession where you put people over profits, society over solipsism, knowledge over materialism. This is my redefinition of success. It’s not the best one, and it’s not noble–but it’s mine.

Two Different Life Scripts

Part of succeeding on your own terms is forgetting everything you’ve heard about success. You must forget what you read in the media about what “the good life” consists of. Ditch the generic life script so many people advise you to follow. In short, you have to stop caring how others define success.  1

I created a list of what many people strive for in life. I’m ashamed to say I was the same way. The second list is what I strive for now.

Success From Following A Generic Life Script

  • A big house that’s barely affordable, but it crushes the Joneses house.
  • A job at a famous company that has amazing perks. 2
  • A fancy title at work that (almost) commands attention.
  • Driving new cars that are expensive to repair, but look fantastic.
  • Marrying someone that needs you and vice versa.
  • Having so many friends, you forget their names.
  • Buying whatever you desire.

Success From Following My Own Life Script

  • A house that’s big enough to easily clean and maintain yourself.
  • A job, a microbusiness, and multiple streams of income.
  • No job title is important to me. “Owner” is the only title I care about.
  • Getting 200,000+ miles on a car you outright own.
  • Having five friends that have my back no matter what, and vice versa.
  • Marrying a person that doesn’t need you, but chooses to be with you.
  • Having the ability to buy things you desire, but only buying things you need.
  • Enjoying the simplest things in life.
  • Having great health and feeling good most the time.
  • Leading a tribe of remarkable people who take care of each other.
  • Waking up whenever I want and without an alarm clock.
  • Knowing your true value and sharing it with the world.
  • Understanding how you fail, learn, and grow to personally evolve.
  • Leaving a sustainable legacy in education, business, and philanthropy.

My pattern of success is easy to figure out. It’s pretty much the opposite of what most people strive for. I’m weird like that. But I’ve never been happier trying to fulfill this list. What will make you happier?

Your Turn

  • So how do you define success?
  • What are your values?
  • What legacy will you leave behind?
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Hi, I'm Peyton. I help people and businesses dramatically improve through digital marketing and story. I'm based in Portland, Oregon — a magical and mysterious city enveloped by a Douglas Fir rainforest.
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