Doing what everyone else wants has its perks.

I graduated from high school right around my 15th birthday. I never liked school and I got nothing but mediocre grades until I skipped from 5th grade into high school. Impressive (to whom?). Then I continued getting mediocre grades until I graduated. It was all very disappointing (to whom?), and I was rejected from LSU when I applied. I wrote a letter to the Dean of Admissions to convince him to let me in anyway, and he did. I kicked ass in college. I was always on the Dean’s list, and I was in the honors program, writing a thesis about international logistics chains in Mexico. Very impressive! (to whom?)

When you do well in school, your parents give you pizza. Everyone nods approvingly when you tell them you’re a Junior at Yale studying “whatever”. Did you ever notice that people in college always say “I’m in grad school,” instead of “I’m learning about botany”? Unless it’s something impressive, then they say “I’m in grad school for physics.” Wow, neat.

So it was all very disappointing (to whom?) when I dropped out of college as a senior. But I made up for it by quickly landing a job at Acme Corp writing software. I had never intended to write software for a living even though everyone assumed I would since that’s what I spent a lot of my time doing as a teen. I was a Senior Application Developer on the “Appdev Team” which was the prestigious team, as opposed to the “Proddev Team.” Neat.

When you start your career as a banker for Goldman or engineer for Lockeed, your grandparents are happy. They gloat to their friends, “Our little Timmy is all grown up! He graduated from Generic U., and now he’s a neurosurgeon!” Did you ever notice how when people talk about what they want to be when they grow up, they say “I want to be a firefighter!” instead of “I want to rescue people.” “I want to be a blogger!” instead of “I want to write.”

It turned out that I was really good at climbing the ladder and getting increasingly high profile and lucrative jobs. When I was 23, I was the head of development at a $28 million dollar software company. The CEO hired me to help him either sell the business or go public.

And it feels kind of good once you’re there. If you ignore the long hours and cloying sense that something isn’t quite right, it’s fun to have stuff. You know you can pay your mortgage, and that feels good. It feels even better if it’s a big mortgage—the bigger the better—because having money to spend means you’re winning.

You can tell how much you’re winning by how much money you spend. It feels good to pay your mortgage, then buy a surround sound system that you pay someone else to install. That way you can casually tell your friends “Oh yeah, the guy I hired to put in my surround sound he was great, I can give you his number if you want.” You’ve come a long way from telling your 5th grade buddy that your 12-speed bike is better than his 10-speed.

All the officers and top sales guys at the company drove Porches, one of them had the most suped-up Ford GT in the world (featured in car magazines, and banned from racing). I drove a car that cost me more per month than all my current bills combined cost me now. It was part of the culture, it’s just what you did there.

Smoke and Mirrors

But that’s the smoke and mirrors of it all. At some point all these facts come together.

You did well in school as a signal to your parents that they could approve of you. When you stopped caring about what your parents thought, you went to grad school because being a grad student signals to your peers that you’re smart and going places.

Who gives a shit what you studied (unless that was part of the signal), or what you plan to do with it, that’s not the point. It’s not for you, it’s a signal to other people that you’re the type of person who does the right things.

Also not for you: hiring a guy who put in your surround sound that you either never use, or constantly use in lieu of meaningful human contact. It was a signal to your peers that you’re the type of person who can afford to have workers install frivolous things on your behalf, because you have money, which means you win.

All this feels great, in an empty sort of way. Our society reinforces every part of this system, all the way down the line, from telling us what a successful life should look like, to programming us to respond to our friends and family in ways that reinforce the status quo. Parents are happy you’re getting good grades, so they can tell their friends about how great you’re doing, so their friends know what great parents they are. Everyone has skin in the game, so no one can just stop playing.

Unless they do.

Letting Go

I used to stress about my car. Keeping it clean, and being paranoid about it getting scratched or damaged. My 4 year old son was riding in the back seat. I stopped at a stop light, and glanced back. My heart jumped into my throat, demanding to exit my body so it could strangle the little shit who was shoving a rusty nail he had found through the fine leather upholstery over and over.

Then it all came into view for me. This car didn’t matter. It wasn’t even for me, it was for my buddies at the company to know that I was one of them. I sold the car, and bought a Cadillac DeVille for $3,200 in cash, less than one month payment for the expensive one.

The car is great and fine. I still drive it today. I drove it from Florida to Austin.

And then I told the president of the heath company that he was full of shit in the middle of a big meeting, which I knew would get me fired. When I was fired, I got a job that suited me better, making plenty of money and working from home.

I’ll spare you the play by play, the point is that every time I threw something away that I had or did for other people, I felt better.

Grasping On

There’s a tipping point in that process though, and since you’re reading this, you’re probably at it, and maybe have been at it for a long time. It’s the point where you’ve let go of the impressive school and big shot title, where you’re ready to live “authentically.” So you’ve dropped everything to follow your path and then… nothing.

What do you do now? There’s no map, there are no mentors. All the signs along this road say “Wrong Way. Go Back.”

You’ve been going through the motions for other people for so long that you don’t know who you are or what you want. Worse, you don’t have the tools to figure it out. You’re just lost.

You have a choice about how to deal with this.

  • I think the ideal way is also the hard way. You’ll cut ties, drop everything, and spend a year doing nothing and everything. You backpack through India, or you ride the rails in your own country. You’re a vagabond, floating in space, totally disengaged with the daily grind of our society. At some point you’ll become reacquainted with yourself and something will grab your heart. And you’ll be free to pursue whatever it is because you have nothing tying you down.
  • The more realistic but less effective (and less scary) approach is to ween off the things that you do for others, and slowly replace them with fulfilling activities. The important part here is that you drop each thing, and you don’t fill the void with anything for at least a little while. Create a vacuum in your mind and life for the meaningful stuff to fill in. It can’t fit if your life is already filled with nonsense and distractions. You’ll know when something grabs your heart, and if nothing comes to fill that void, just keeping making the void bigger as you drop more nonsense, and eventually you’ll have enough to space to fit your heart’s desire.