3 Pieces Of Advice I’d Give My 18-Year-Old Self If I Could

Once upon a time…

At 3:45pm Friday afternoon, the corner of Fermor and St Mary’s was a busy place. The intersection is dominated by Glenlawn Collegiate, a brown brick complex that happens to be my alma mater. It’s one of the division’s two high schools, virtually unchanged in the eleven years since I graduated except for the addition of red LEDs on the sign outside.

I happened to be passing by right at that time for no particular reason.

The teenagers in the giddy mob at the bus stop looked a lot younger than I remember being in high school. At the time I figured seventeen was about a year away from being a proper adult, but these kids were definitely children. Loud and aimless. Maybe we were too.

The number fourteen and the number fifty-five rolled in one behind the other, brakes whining, and most of the mob funneled in. When the light changed, both buses pulled away, and that’s when I spotted him.

His identity didn’t register for a moment, but his hurried, self-conscious gait appeared so shockingly familiar to me that I froze. He was wearing grey, baggy cargo pants with ragged bottoms and a drab green t-shirt that was too big for him. His hair was a half-messed mop of gel-hardened spikes.

He was walking towards me, looking over at the departing buses, and we almost collided. When he caught my bewildered stare, I realized who he was.

It was me. At eighteen.

He was stunned too, but clearly knew who I was. Suddenly I felt a lot older than my twenty-nine years. Knowing him, I knew I would have to take the initiative here. I recovered, and smiled. He didn’t.

“You missed the fourteen.”

“Yeah I know.”

“We’ve got twenty minutes or so till the next one. We should talk,” I said, hopeful.

“Sure.”

***

Imagine if you had a golden opportunity to talk to your eighteen year-old self.

Really picture this younger you. Think back to who you were in high school — what you wore, who you were friends with, who you thought you were, what place you felt you had in the world. The more details you can summon, the better. You are sitting across from this young person at a diner, and they’re all ears. For twenty minutes.

What would you say? What advice would you give? And knowing how this person thinks, how would you say it?

(If you aren’t yet twenty, then imagine talking to your thirteen-year-old self. If you are thirteen or younger and you’re reading this blog, then you definitely don’t need any help from me.)

If I only had time to drill him with a few important points, here’s what I’d try to get across to my younger self:

1. Spend your time and money on things that make your life better, rather than things that make you feel good.

“It’s Friday. What are you going to do when you get home?”
“Play Civilization 2 on the computer.”
“Where will that get you in life?”
“If I’m lucky I can eradicate the Aztecs by suppertime.”

I grew up in a fairly comfortable environment. Not a lot of crisis, but regular ups and downs certainly. Like anyone else, I sought things that made me feel good and avoided things that didn’t make me feel good.

When it came to things like work or challenge, I dropped them categorically in the “things that don’t make me feel good” column. Anything in that column was to be avoided when it could be avoided, and endured when it had to be endured.

Not that I’m blaming society for my troubles as a young adult, but nobody ever seemed to have a very good explanation for why I actually might want to work hard and challenge myself. Not “have to”, or “need to,” but “want.” The reason was always, “It’s just something you should do,” or “You’ll be glad you did when you’re my age.”

Whenever I found myself working hard, or butting up against something that was difficult for me, I found it quite unpleasant, so why would I ever do those things when I could avoid them?

And man could I avoid them! I grew to be a very cunning bullshitter and effort-avoider. Work, planning and challenge took on the roles of necessary evils in life, rather than the voluntary paths to fantastic, glittering prizes I later learned them to be.

Even in my mid-twenties, once I learned how to avoid the worst of the woes that a gratification-based existence could create, I still was primarily concerned with feeling good as often as possible. This meant senseless overeating, avoiding any truly strenuous form of exercise, excessive drinking, video games, buying stuff I don’t need, and otherwise indulging myself while staying well within my comfort zone.

I never went into serious consumer debt, but I certainly squandered all my disposable income on various ways to feel good, none of which left anything useful in my life, or put me in a better position to take on the rest of it.

If I could have back all of the thousands of hours I spent playing video games alone, I could have learned several languages, built several businesses, saved a fortune, become a killer guitar player, and built the body of a Roman demigod.

It was a rainy afternoon in 2008 when I realized, “Holy crap! I’m boring!” I had never really built anything in my life. I made no determined attempt to get better at anything, to increase my earning power, to develop skills and relationships, I just spent my time and money on whatever promised to keep me feeling all right. In old-adage-speak, I was eternally buying fish, instead of learning to catch my own.

This is one of the most important things I ever learned, not that anyone ever flat-out said it to me. If only my 29-year old self showed up after school one day, bought me a milkshake, and slapped some sense into me, I’d be light years farther down the road.

At eighteen, young David doesn’t know what’s in store for him. He is still unaware of a smarter way to live, and is about to experience five or six years of fruitless pleasure-chasing and ailing self-esteem. In terms of new skills, assets and capabilities he will have little to show for it by age 25, just some real hard life lessons.

So, teenage David: Always try to get a decent return on investment for your time. Use your time and money to build assets and leverage in your life, not just to get to the next bit of time.

***

2) Every single day, get better at meeting people and developing relationships

“Why don’t you go out and meet some people tonight, instead of fighting the Aztecs on the computer?”

“I don’t like meeting people I don’t know.”

“Well you never know them when you just meet them. How will you make more friends?”

“I have friends.”

“But there are so many people out there who can teach you things and open doors from you.”

“Leave me alone, ok.” He appeared to grow impatient, and looked over at the door.

I waited till his eyes caught mine again. “Be careful what you wish for.”

These days I often describe myself as a “recovering introvert.” Comfort was the north on my personal compass, and talking to people I didn’t know was due south.

I was very much dependent on my existing friends to fulfill my social needs. I rarely took the initiative and made the plans. That I left to everyone else — because it entailed zero risk on my part.

Sticking to behavior with zero risk is a real tragedy, because it means there is no discomfort, and no discomfort means new ground is seldom broken. With that habit, social skills develop extremely slowly, because there is no need to learn anything you don’t already know how to do.

Teenage David, please don’t only do what’s comfortable! That’s a perfect recipe for mediocrity. The older you get, the greater will be the gulf between what you could be and what you are, and the more sorry you’ll be.

When it comes to meeting people, it’s easy to avoid it because they’re only strangers then. You can always write off a stranger as irrelevant to your life, as you know it right now. But you don’t realize that that stranger could have been your best friend, your mentor, your key to a fantastic opportunity, or even your wife. Everyone you know now was a stranger once.

A new person in your life can open a new chapter. They can lead to new lines of work, new passions, new insight about the world and a broader, more colorful identity for you.

Most of my life, I resented people with connections. I hated that I had to resort to cold calling to find a job lead, while other people could just drop a friend an email. Of course, I didn’t see that this doesn’t happen by accident.

I always waited for others to take the lead in social situations. I would always defer to somebody with more skills or more guts, and soon I began to identify myself as a second, a subordinate, a beta personality. Clawing your way back from a subordinate social role is a hell of a battle, and the later you start the tougher the climb. Don’t let yourself slip that far.

Again, teenage David doesn’t know what’s in store for him once he leaves high school. His high school friends will move, marry off and become otherwise irrelevant. He’ll always have some friends, but he’ll depend on them for a sense of identity and for social fulfillment. It will be ten years of sheepishness and dependence before he realizes what’s happened and makes a point of becoming socially independent.

So, teenage David: Be a figure in a lot of other people’s lives, and keep bringing new people into your life. Meet people every day. Initiate conversations. Don’t shrink away.

***

3. Don’t work for anyone else

“What are you studying in school?”
“Uh, computer science.”
“Why do you like computer science?”
“Well I don’t, but there are lots of jobs in that field right now.”

Oh teenage David. Look at me. I’m twenty-nine and currently hatching a plan to escape from my second career. It’s not horrible, I just don’t want to spend half my waking life helping rich land developers get richer. I never did, though I didn’t always think I could do better.

Before you sign on for a chunk of college loan debt so you can learn what others say you should, hear me out.

What is normal in our society is to sell your time (customarily, forty hours of it per week, in five eight-hour stretches) for an agreed-upon flat rate. This is what most people do and what most people will tell you to do.

This is your time on earth. We’re talking about sizable pieces of the only life you’re going to have, sold to a company that — and let’s be honest — is probably not doing for the world what you’d like to do for the world. Do you really want your role on this planet to revolve around smoothly-running data entry systems? Insurance policies? Widgets?

But most people don’t see another way. The standard way to make a living is to rent yourself out for the better part of five days a week to achieve someone else’s purpose. In the time that remains, the weekends and the fleeting hours of the evening, you can live your life, or at the very least recover from your workweek. Sounds like a regular deal with the devil.

Rent out your forty hours like that, and somebody else gets to decide:

• When that forty hours is (right through the prime daylight hours, almost always)
• How you are to be spending that time, and why
• What you are allowed to wear, do and say during that time
• When you can take a vacation
• Who you work with
• When you deserve more money
• What your purpose is, at least until 4:30
• Whether to continue to supply your income or not

Once you’re playing this game, the main strategy is to make a lot of money for your boss, and over time they will share a small fraction of it with you in the form of incremental bumps in your salary.

You may luck out, of course. Some people do find that their own purpose matches the purpose of the person they sell their days to, so there’s no conflict there. But that’s not reality for most of us.

Don’t get mixed up in this racket.

What can you do instead? Do what your would-be boss is doing. Create something of value, and find the people who value it most. A service or a product that people value, and that others aren’t delivering as well, or at all.

If you need help to produce it, you will certainly be able to find a lot of people willing to sell you their time for a flat rate. If you need a method, there are hundreds of established, tested models in the library, online (yes, online), and at the bookstore. Pick one that speaks to you and see what happens.

The idea of running my own business always sounded preposterous. I fell for one of the biggest entrepreneurial myths: that you must risk a large sum of money to start a business venture. I think I came under that impression by watching an episode of Roseanne in which a financial advisor tells her she’d never heard of anyone starting a business for less than fifty thousand dollars. I missed the part where they said they were talking about restaurants.

I’d heard most businesses fail within five years (or something) and of course I pictured myself becoming part of that majority, ending up penniless in a green shack at the corner of Baltic and Mediterranean.

No, I dismissed any entrepreneurial ambitions long before I was done high school. I knew that such an uncompetitive, unambitious soul would always have to work for someone else. That was just reality.

So I jumped on the lucrative professional field du jour, computer programming. Four years later, I’d racked up some debt, run my self-esteem into the ground, forgotten everything I’d learned about computer programming, and started again in the engineering industry.

Now it’s another six years down the road, and I’ve left my job to travel abroad. When I return, I’m devoting as much time as it will take to create a bossless income. I’d rather work twelve hours a day for myself than eight for someone else.

Without this advice, teenage David will be entering a cycle of employer dependence he may never know he’s in. He’ll go to school, rack up some debt, and get a job. He won’t exactly hate his job, but he’ll still dread the fleeting, final hours of Sunday evenings, and he’ll still think Friday is necessarily a better day than Tuesday. Over the decades he might eventually trudge his way up to high five figures, possibly even topping out at the low sixes. He will always depend on others for his income and will only be able to travel in two-week stretches for the first sixty years of his life.

So, teenage David: Don’t sell your time to someone else’s purpose. You can do better. Be poor for a while if that’s what it will take.

***

When I finished my spiel, he said “Thanks,” as if he’d understood, put his earphones in, then trotted out to catch the bus.

I suspect he went home, jumped on the computer, and proceeded to make every one of the mistakes I needed to make to be able to give him that advice.

Good for him.

LIKE THIS? READ MORE DAVID CAIN HERE.

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