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?


How Clutter Affects Your Brain (and What You Can Do About It)

How clutter affects you and what you can do about it. @ ooomf by Mikael Cho


Cleaning out your closet, emptying your inbox, putting things where they “belong.”

A few years ago, I worked at a web design agency as a product manager.

The part of the job I loved the most was working on product with our design team and clients. Unfortunately, this only made up about 10 percent of the work that I actually got to do.

The majority of the time, I was trying to control the constant flow of stuff – keeping track of meeting notes, searching for files, and trying to stay up-to-date with the latest technology news.

I was mentally exhausted.

I’d get home feeling that I hadn’t really accomplished anything.

Once I left the agency and started ooomf, I wanted to fix how I approached consumption in my life.

Over the last few years, I’ve discovered ways to reduce the noise of stuff around me so I can focus on creation and have more time for the things that matter most.

The last year has been the most productive of my life and I owe a lot of it to understanding the importance of decreasing how much I consume and coming up with ways to cut clutter.

How clutter happens

You collect things for a number of reasons – maybe you think you’ll need to use it later, it has sentimental value, or you spent good money on it so you feel you need to keep the item, even if you haven’t touched or used it in weeks, months, or years.

You might be holding on to that book you bought a year ago that you swear you’ll read or those killer pair of shoes that you’ll bring out for just the right occasion.

But the reality is, you probably made a mistake in buying those things and it literally hurts your brain to come to terms with that fact.

Researchers at Yale recently identified that two areas in your brain associated with pain, the anterior cingulate cortex and insula, light up in response to letting go of items you own and feel a connection towards:

This is the same area of the brain that lights up when you feel physical pain from a paper cut or drinking coffee that’s too hot.

Your brain views the loss of one of your valued possessions as the same as something that causes you physical pain.

And the more you’ve commited emotionally or financially to an item, the more you want to keep it around.

Why Apple wants you to touch their stuff

When it comes to physical things, merely touching an item can cause you to become more emotionally attached to it.

In this study, researchers gave participants coffee mugs to touch and examine prior to participating in an auction.

The researchers varied the amount of time the participants were able to handle the mugs to see if this would have an effect on the amount of money participants would be willing to spend on the mugs during the auction.

The results of the study showed that participants who held the mugs longer, were willing to pay over 60 percent more for the mugs than participants who hed the mugs for shorter periods.

The study concluded, the longer you touch an object, the greater the value you assign to it.

Apple is familiar with the effect of touch on your psychology and has brilliantly designed its retail stores to help you build an emotional attachment to their products.

Here’s a shot of an Apple Store:

Author Carmine Gallo is writing a book about the ins and outs of the Apple Store. Gallo explains that everything in the Apple Store is designed for you to touch and play with, to make you feel like it’s your own. Gallo states:

The main reason notebook computers screens are slightly angled is to encourage customers to adjust the screen to their ideal viewing angle…The ownership experience is more important than a sale.

When you introduce new items into your life, you immedietely associate value with these items,making it harder for you to give them up in the future.

This psychological connection to things is what leads to the accumulation of stuff.

Clutter’s impact on your brain

Whether it be your closet or office desk, excess things in your surroundings can have a negative impact on your ability to focus and process information.

That’s exactly what neuroscientists at Princeton University found when they looked at people’s task performance in an organized versus disorganized environment.

The results of the study showed that physical clutter in your surroundings competes for your attention, resulting in decreased performance and increased stress.

A team of UCLA researchers recently observed 32 Los Angeles families and found that all of the mothers’ stress hormones spiked during the time they spent dealing with their belongings.

Similar to what multitasking does to your brain, physical clutter overloads your senses, making you feel stressed, and impairs your ability to think creatively.

Clutter isn’t just physical

Files on your computer, notifications from your Twitter and Facebook accounts, and anything that goes “ping” in the night competes for your attention.

This creates a digital form of clutter that erodes your ability to focus and perform creative tasks.

Mark Hurst, author of Bit Literacy, a New York Times best seller on controlling the flow of information in the digital age, put it best when he said:

Bits are a new material.

When you have to-do items constantly floating around in your head or you hear a ping or vibrate every few minutes from your phone, your brain doesn’t get a chance to fully enter creative flow or process experiences.

When your brain has too much on its plate, it splits its power up. The result? You become awful at:

  • filtering information
  • switching quickly between tasks
  • keeping a strong working memory

The overconsumption of digital stuff has the same effect on your brain as physical clutter.

Finding your perfect storm

I like to keep things neat but when I used to clean my room to perfection, my mom would still see that same room as a disaster.

Everyone’s tolerance for clutter is different.

Researchers have even found that certain people need a bit of a mess in their surroundings to feel inspired and get work done, stating that:

A clean desk can be seen as a dormant area, an indication that no thought or work is being undertaken.

For instance, if you look at this photo of the home office of Steve Jobs, it’s not exactly the picture you’d expect of a zen-like visionary obsessed with less:

On the other hand, there’s TreeHugger founder Graham Hill, who traded in his million dollar mansion for a 420 square foot apartment that only has the bare essentials.

His kitchen consists of 12 salad bowls and utensils:

In an interview with the New York Times, Hill stated:

I like material things as much as anyone. I studied product design in school. I’m into gadgets, clothing and all kinds of things. But my experiences show that after a certain point, material objects have a tendency to crowd out the emotional needs they are meant to support.

While clutter has been shown to negatively effect your performance, it is your perception of clutter that matters, not someone else’s.

If having a notebook, pen, or a photo of your significant other on your desk, doesn’t feel like clutter to you, then it’s not.

You should seek to create spaces that make you feel at ease.

Editing the noise: 4 ways to master clutter

There are millions of sources of information and things for you to consume so it’s important to figure out a way to control these streams so you have more time to do things that matter.

Here’s 4 things that have been working for me:

1. Apply constraints

One of the principals of good design is constraints.

You can apply this same theory to create a system for mastering consumption.

For instance, set a limit for how many people you follow on Twitter, how many books you buy, or how many apps you own.

I set a limit of 200 people I follow on Twitter and I don’t buy any books until I’ve finished the current book I’m reading. I also don’t purchase or download any apps until I need them.

There will always be more information available than you can consume so set limits so you’re no longer simply trying to just get through it all but rather enjoying more of what you consume.

2. Use small storage spaces

Cutting down on your storage space can do wonders for limiting consumption. Try cutting your closet down to 10 hangers or force yourself to use a small bag when you travel.

Do you really need a walk-in closet or a rack for all your shoes? Try constraining your storage spaces and you’ll quickly identify what you really need.

3. Conduct a monthly review of your closet

Every month, review your closet looking for items you haven’t worn. If it’s summer and you have t-shirts, shorts, or shoes that you aren’t using, put them in a bag to sell on eBay or Craigslist or give them away.

Another option is to try and get rid of one item a week until you’ve cut your belongings down to the things you actually use.

4. Remove all files from your desktop daily

If you work on a computer, having a cluttered desktop every time you turn on your computer can give you a constant uneasy feeling.

At the end of each day, remove every file from your desktop. If you don’t have an immediate place to move the file, create one folder on your desktop and drop the stray files in there.

Here’s a screenshot of my desktop screen with one “Home” folder:

Clutter, whether physical or digital, is something you’ll always have to deal with but it can be controlled.

Finding ways to stear the streams of consumption in your favor will give you a sense of power and a freed mind, leaving room for you to create and experience life without constantly filling your cup to the top with someone else’s sugar.