Comparing Myself To Millionaires And Billionaires, 5 Unforgettable Life Lessons I Learned Before Turning 29

I’ve never hung out with people my own age.

From the moment I logged into my first MMORPG, the World of Warcraft, as a video-game addicted 14 year old, I’ve spent more time with people twice, sometimes three times my age than I have my own peers.

All throughout high school, I didn’t have a group of friends I sat with at the lunch table, or followed home on a Friday afternoon to call up girls and steal beers out of Dad’s garage refrigerator. All my friends were online, in the World of Warcraft, many of whom were in their late twenties and early thirties. My guild leader and one of my first “mentors” was a lawyer. Our tank worked for the CIA. Our lead Warlock was in and out of chemotherapy, trying to beat cancer. Our lead Druid was a stay-at-home mom (whose husband was also in our guild). Our lead Rogue was a software engineer. The list goes on and on.

At the time, I didn’t think much of it. I was obsessed with the game, and I found myself endlessly entertained by listening-in on conversations in our guild Ventrilo channel (the old-school gaming version of Skype) talk about things like politics and the stock market and how to deal with a crying two-year-old. To be honest, I learned more about life from these overhead conversations on the internet than I did in my high school classes—and at a very young age, made me feel very comfortable being the youngest person in the room.

This past weekend, I turned 29 years old.

For the past decade or so, ever since I got into online competitive gaming as a teenager, I’ve made it a point to spend time around people much older, much smarter, and much more successful than myself.

When I was 17 years old, I did this by spending every waking hour playing World Of Warcraft with the highest rated gamers in North America—and sure enough, all those hours eventually led to my becoming one of the highest rated gamers in North America too.

When I was 20 years old, and I decided I wanted to become a bodybuilder, I spent three hours per day, seven days per week, lifting at the Xsport Fitness with the biggest guys in the gym. These were older guys, all in their late 20s early 30s, and some even in their 40s and 50s. They saw me show up the same time they did, and eventually invited me to lift with them. I didn’t have a group of friends in college. I can count the number of parties I went to on one hand. Instead, my social life was lifting weights with professional powerlifters and bodybuilders twice, three times my age.

When I was 23 years old, I started working as an entry-level copywriter at an advertising agency downtown Chicago. There, I found myself in a position to be mentored by the creative director—a very successful serial entrepreneur a decade ahead of me. I sacrificed everything in order to learn from him. I took on any and every additional project I could get my hands on. I stayed late. I would tag along to meetings with him on the weekends, just to be “in the room” and listen. While the rest of my peers spent their early 20s reliving their glory days with college friends at bars, I spent my early 20s following my mentor around, already understanding the immense value I could gain by spending as much time with him as possible.

And when I was 26 years old, I took the leap to start my first company, Digital Press, working exclusively with some of the world’s most accomplished business leaders: founders of heavily funded startups, executives of Fortune 500 companies, award-winning speakers, NYT best-selling authors, Grammy-winning musicians, Olympians, Silicon Valley investors, and more. By the pure nature of our business, it became common for me to spend 10 hours per day talking to people ten or twenty years older than me worth millions, tens of millions, even billions of dollars. And as I moved through my late twenties—27, 28—I started to forget entirely what it meant to spend time with people my own age.

But wasn’t until I turned 29 this past weekend that I realized how devoted to this sort of “be the dumbest person in the room” learning process I’ve been.

I don’t have a big group of friends I see every weekend.

Half the time, I forget I’m in my 20s at all.

I’ve gotten so used to comparing myself to people older than me, more successful than me, that I often compare myself to where these incredible people are today—opposed to where they were when they were my age. And on the one hand, this approach has paid dividends for my own personal development. I can attest to the power and value of being “the youngest person in the room.” But on the other hand, it can sometimes be misleading to compare yourself to someone a decade ahead. You tell yourself you should be further along. You get frustrated when you feel like things aren’t happening fast enough. And some days, you misjudge altogether whether you’re actually “on the path,” unsure of whether or not you’re moving at hyper speed or moving at all.

In an attempt to better understand my own journey, and do some good ol’ fashioned reflecting as I skirt into my 30th lap around the sun, here are 5 life lessons I’ve learned from those much further along—all before I turned the age of 29.

1. Knowledge is more valuable than money. Skill is more valuable than circumstance.

The professional world is engineered to reward linear steps up the ladder.

We applaud the promotion, the pay raise, the clearly identifiable “marker” that proves progress—whether or not progress has actually been made. If you want proof, listen close to how many people say, “I was going to quit my job, but they gave me another promotion so I decided to stay.” Here, progress has very little to do with any true leap forward in terms of ability, but rather a willingness to simply show up and breathe.

When I look at all of the different types of people I’ve been fortunate to learn from, none of them saw the world through this lens. None of them allowed someone else to define for them their value, or their next step up the ladder. In fact, many of them ignored the ladder entirely, built their own, painted their name on the side and then stood at the top. And the reason they were able to do so was because they understood the true value of “value.” Money isn’t “value.” The title of CEO isn’t “value.” Value is what capital or circumstance can amplify—and if you are talented, if you possess deep expertise and skill refined over years, then remove the money and remove the fancy title and you are still “you.”

Masters of their craft, true leaders of their industry, care far more about skill than circumstance.

And as a result, circumstance always follows.

2. If you want to make $X, determine the result a person or company needs to drive at that value.

One of the most insightful things I’ve ever picked up from my list of formal and informal mentors was this: “It’s easy to make however much money you want to make in life. All you have to do is figure out who would pay that much, for what, and then deliver it.”

It took me a long time to understand what that actually meant.

Let’s say you want to make $100,000. A lot of people will hold that number in their head and say to themselves, “That’s a lot of money. I don’t know how I’ll ever make that much money.”

But if you reverse-engineer how you arrive at that number, it becomes a much simpler equation to solve. Tech companies pay developers $100,000. So, without overcomplicating the issue, you could say that by learning to code at the level of an experienced software developer, that’s how you could make $100,000.

But what if you want to make $250,000? Who is willing to pay $250,000? And for what? Maybe you discover that advertising agencies routinely pay sales directors $250,000 per year to bring in five large accounts each worth $5M or more. Without overcomplicating the issue then, we could say that by learning to bring in five large accounts each worth $5M or more, that’s how you could earn $250,000 per year.

It wasn’t until I started to really apply this way of thinking to my own life that I started to realize how wise this advice really was. Making more money has very little to do with “years of experience” or where you went to college. To be honest, most real decision makers don’t care. The only thing they care about is the result you are able to drive. Which means, if you want to make more money, all you have to do is understand what result they are looking to drive, and how much they are willing to pay for you to drive that result.

If you can drive that result, then voila.

3. Not every opportunity is “life changing.” Only say “Yes” to opportunities that will move you closer to a “life-changing scenario.”

When I was 27 years old, I moved to Los Angeles.

My first few months on the west coast were a whirlwind. Again, because of the nature of my business, I found myself talking to some of the most brilliant, successful, and accomplished business leaders in the world. And coffee meeting after coffee meeting, lunch after lunch, I started to notice a trend. All of them made decisions about how and where to invest their time based on whether or not the matter in question would lead to a “life-changing result.”

For example: when you’re living in a mansion, and you have four sports cars, and you have the means to fly private and stay at the nicest hotels and resorts, what’s a life-changing scenario? If you earn $200,000 more per year, is that life changing? Not really. Another $200,000, at that level, doesn’t change your life very much—and frankly, neither does another $2,000,000. Both of those “levels up” just mean a slightly bigger house, a few more unnecessarily lavish dinners, and a few extra angel investments in exciting new companies. But another $2M doesn’t mean you can buy your competitor out of your own pocket. Another $2M doesn’t mean you can scoop up an entire neighborhood of real estate. You’re dealing with an incremental step up—when what you should be aiming for is an exponential one.

As a 27-year-old in my first 1-bedroom apartment (I’d been living in studio apartments on an air mattress since graduating college), this was a tough mentality to wrap my head around. In my mind, an extra $200,000 did seem life-changing. But that’s because $200,000 was life-changing to me, not to someone who spent $200,000 per month in living expenses.

Once that clicked, I started to apply that same logic to my own life. And that’s when I realized that no amount of me doing 1-off ghostwriting projects was going to “change my life.” An extra $1,000 wasn’t life-changing. Even an extra $10,000 wasn’t life-changing. I needed to change the target I was aiming toward, and only say “Yes” to the things that were going to truly move me to the next “life-changing” scenario.

4. Enjoy the journey. Because the things you crave to escape from will be the same things you miss once you’ve “made it.”

When I was 28 years old, I was fortunate to work on a project with a Grammy-winning musician.

I had actually spent years listening to his music. I had his first two albums downloaded onto my computer, and I remember watching some of his biggest music videos in my college dorm room. Working together felt like a massive sign of approval as to my career as a professional writer, and the level I was suddenly playing at.

I was being brought on as an advisor for the project’s communications, and to get some quality time together, he invited me out to his house. Inside, he had this sprawling studio, hand-crafted and built for other musicians to come and go, and be part of the collaboration process. It was beautiful, to say the least—and everywhere I looked, he had all the latest equipment, keyboards, guitars, racks of compressors, and so on.

As we were talking, and in an effort to better understand him as a person, I asked him how it felt to have literally every single musical option at his fingertips, all the time. And his response took me by surprise. He said, “It’s overwhelming. I think having constraints is better.”

He then proceeded to explain how he was looking to rent a modest 1-bedroom apartment in the middle of the city—somewhere he could work on his next album with just a laptop, a midi controller, and a pair of headphones.

Something about that conversation hit me like a ton of bricks.

Here was this guy who had reached the highest levels of fame in the music world, had a massive home (one of several), and a custom-built studio with every tool imaginable, and he wanted to leave it all and make his next album on his laptop in a 1-bedroom apartment. I couldn’t understand it. That is, until I came back to my 1-bedroom apartment at the end of the weekend, started writing, and realized that a bigger apartment, a nicer desk, and a better view had very little to do with the creative process itself.

5. Reaching the top of one ladder, means having access to the top of every ladder.

I used to see the world in slivers, each industry or space separated from the others.

This perspective of mine was shattered one night, when I attended my first private dinner event in Hollywood Hills. The youngest person at the table by a wide margin, I was seated beside an award-winning fashion designer, a Silicon Valley legend, a real estate mogul, a blockchain “on-paper” billionaire, and seven others of similar stature. And it wasn’t until I was introduced—”Cole is one of the most-read writers on the Internet with over 50 million views, the #1 writer on Quora, and the founder of Digital Press”—that I realized how and why I was there.

I’d reached the “top” of my ladder. Even if my ladder was little ol’ Quora.

From that moment on, I started to realize how the dinners I went to and events I attended were melting pots of people who had mastered something. It almost didn’t even matter what the “thing” was—there were Olympic fencers mingling with e-famous YouTubers, female billionaires bouncing ideas with behavioral scientists—so long as you spoke the language of ambition and mastery. Once you were “in the room,” there was no longer a gap between you and the award-winning film producer. You were both there, because you had both climbed to the top of your respective fields. And that’s what made the connection meaningful and worthwhile.

I suppose my grandmother had been trying to teach me this lesson for many years. In her words, “You can learn something from everyone.”