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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.



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.



What would you tell your eighteen year-old self if you had the chance?

Update: Looking for more life lessons? This post has been featured with over 40 others on Abubakar Jamil’s Life Lessons Series.

Photos by foundphotoslj and John Steven Fernandez

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Vaibhav Mule October 19, 2013 at 12:17 am

Dear David,
I really love those three things which you have shared.
I’m going to be 18 in few months and I will be taking care of things which you have told,

Vaibhav Mule

Louis October 24, 2013 at 8:26 pm

I want to speak with 50 year old David ASAP.
Great articles and I’m glad you’re still writing them.

Aurora Jean October 25, 2013 at 8:16 am

Hey David,
I just stumbled upon this site for the first time today, but I just wanted to let you know that even though you posted this article maybe three years ago, it’s still having a positive impact. As a 20-year-old myself, I thoroughly enjoyed reading this. Perusing through your other articles, I am both inspired and in agreement with much of what you say. Thank you for taking your time to write your thoughts down and share them with the world. It really is making a difference.

Asbel October 27, 2013 at 11:53 pm

Thank you for this. It was definitely worth the read. This spoke to me, spooked me too… I am studying computer science and feeling pretty overwhelmed with how competitive it is…

Megan November 12, 2013 at 11:53 pm

David, based on this article, I really think you’d be interested in this business opportunity I have going for me. I’m only 20, but I know for a fact I’m going somewhere, especially since every point you hit was relatable to what I believe now. I stumbled upon your article from a friend that posted it, and it could be a game changer for you. Email me if you’re interested in checking this opportunity out.

Scott December 5, 2013 at 11:21 am

This is brilliant. I’ve often imagined having a similar discussion with my 18-year-old self. Thank you.

Jeff December 31, 2013 at 7:26 pm

This was a little painful to read. I’m years and years down the road and still haven’t mastered everything here.

My problem was knowing EXACTLY what I wanted out of life and being confronted with almost an entire world going in EXACTLY the opposite direction. I’ve made a very few friends who had other friends, so I have a decent number of people in my life, but even my friends tell me I need to Compromise A Little (which generally means “do what *I* want and you’ll get a morsel or two”).

But if I could give advice to my 18-year-old self, it might run like this (besides what you’ve already written):

“1. Join someone else’s cover band; don’t try to start one from the ground up with your friends. That’ll get you into the community of musicians (and who knows where that might lead?), and it’ll give you the performing chops you’ll need when you want to make your own music. Just make sure you’re good enough to get into someone else’s band. And then you’ll have a bit of money to spend on going to clubs instead of not going to clubs because your job doesn’t pay well enough.

“2. Have a space for your own music. It doesn’t HAVE to be all selling out and playing crap music for peanuts or all basement tapes made for no one while burning the midnight oil. Just *plan* a bit.

“3. No one out there in the adult world knows that you were massive fun to pick on in school. People *generally* aren’t gonna be jerks on *that* level, so you can stop being afraid of everybody.

“4. Do what you can with what you have. If that means using your banks of keyboards to make original music instead of your dream prog-rock glam-metal power trio that comes across like Cirque du Soleil playing Bartok, then do that. (Understand, that’s a dream I’ll never abandon.)

“5. Major in music. You might as well, because the major you go for as a *compromise* isn’t really going to do you any good besides just having A B.S. Degree.

“What it comes down to is: If you can still be the person you want to be, TAKE THE BIRD IN THE HAND. It might set you up for later. I know you think you don’t have the time because you’re seeing 20-year-olds getting their big break while you’re still 18 and nowhere, but DON’T WORRY ABOUT IT. There’s no sense worrying. Most of all, DON’T THINK YOU’RE A FAILURE JUST BECAUSE YOU DON’T HAVE A RECORD CONTRACT. Don’t even think you’re a failure because you can’t make a living doing what you love, which is nearly impossible anyway if what you love is music. Just be the person you aspire to be and do your best work.”

Of course, wanting to be a musician at all kinda throws a spanner in the works to begin with, so I don’t know how this applies to others.

Jennifer January 6, 2014 at 3:02 pm

I wonder if it would be worth it to write down the questions/thoughts your current self would ask/tell your future self?

April March 28, 2014 at 3:09 am

Wow. Just that one thought of my 18 yr old self and I could just feel the despair rolling in like the tide. I was absolutely broken, I thought beyond repair. I’m just going to tell my 51 yr old self the same thing I would tell my 18 yr old self. I am worth it. Thanks :)

Natalie BoJingles April 4, 2014 at 11:06 pm

I don’t know how I got to this page.
Random searching and late-night delirium; avoiding university coursework. Avoiding any hardwork and effort really.

I’ve been so inspired by your post, I’ve just wrote a 2 page manifesto to myself about why I am at university and what I need to do to get my arse back in gear.
I’m 25. Got myself back into studying at 24, after a few years working shit jobs and smoking pot. I do love the instant gratification.
But the long-term hardwork for gratification is what its about. I want to work for myself, I have ideas and experience now to actually make it work, if I invest energy and don’t give in to the easy laziness and fear.
(I want to be part of a community centre teaching music, hulahooping, yoga, meditation, gardening, sustainable energies, ecological principals etc)

Thank you for reminding me.

I hope you’ve had wonderful adventures on your travels and are suitably inspired to work hard for yourself.

Good luck!!
(with love and gratitude also)

mithi April 22, 2014 at 4:34 am

I can totally relate to this post. When I compare my 18 year old self with my present 25 year old self, both seem to be very different individuals. I was very confused because I looked at the way most of the of the world functioned as a benchmark and could not fit in. I love the way I have turned wiser and thats the best thing about growing up. Things start to fall in place if you give enough thought to them, learn from mistakes and take responsibility for what happens to you. The only thing I would tell my 18 year old self is: “be the way you are because you are on the right track.”

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