I worked in corporate America for five years. After 60 months working for The Man, I realized a blunt, brutal truth that cannot be denied:
The only way I could make more money was if my boss allowed me to.
And most of the times, my boss hated me or was so dysfunctional no one could rise through the ranks.
This lesson has several blunt caveats, too.
First: You’ll never make more money than your boss. Their ceiling is your ceiling. If your boss isn’t rich, you certainly won’t be getting rich at the company, either.
Next: Effort usually doesn’t scale. As best-selling marketer Seth Godin put it: “The eager-beaver employee expends extra effort to make a mark but soon learns that it doesn’t scale.” Twice the effort usually doesn’t mean double the money.
Finally: This is how most people’s careers look like. Most people work traditional jobs, and make about the same as everyone else, give or take a few tens of thousands of dollars a year.
How depressing, I thought glumly.
Making money is important to me. When I was 16, I saw my father’s million-dollar construction business go completely bankrupt virtually overnight during the recession — we lost the cars, the house, the business, my dad had to leave the country to find work, and my mom, three siblings and I had to cram into my grandpa’s tiny 3 bedroom home as we finished high school.
I never wanted to feel that way again. I began studying money, and learning how rich people actually earned their money.
I found there are basically two ways to get really wealthy: through your boss, or through entrepreneurship.
Option One: Make Your Boss Give You More Money.
“If you work hard for eight hours a day, you might get promoted to manager where you can work hard for ten hours a day.” -Old proverb
When I was 23, I was offered my first job out of college working 40 hours a week at $10/hour. At the time, I thought that was a ton of money. And at the time, it was.
A few months into the job, I summoned the courage and asked for a raise. They gave it to me — $12/hour now! Holy smokes! I’m going out to a nice steak dinner!
A few months later, I asked for another raise.
And they gave it to me!
At 23, I was making $16/hour. It was more money than I thought possible for an English major to make.
Things were fine, for a while. But then they abruptly fired me, and I was out of work for eight months.
It took a long time to start making that much money again, but when I got a telemarketing job for $20/hour, I began to realize an uncomfortable truth: the more money I made, the more pressure and stress my boss was going to put on me. My sales manager was only making a measly few more dollars than me, but he was losing hair with the amount of stress his boss was putting on him.
I began to realize an even more uncomfortable truth:
There are some jobs where you simply can’t get wealthy. There are really only two ways to get wealthy: if your boss allows it, or becoming an entrepreneur.
I saw “lifers” in corporate America — these people had worked hard enough for long enough, and now enjoyed a low six-figure income where they could buy a nice house in the suburbs and take four weeks of vacation a year instead of the usual two.
It struck me that that life was never something I wanted. The term “golden handcuffs” came to mind. Sure, you’re making some nice money — but is it enough to have the life you really want? If it is, great. But for me, freedom of my time was the most important value; who cared if I made a lot of money if I had to spent 60 hours/week at the office?
A key moment for me in my career was when I finally got a cushy office job after a solid year of networking and interviewing. My first couple days on the job, as I was getting to know my new coworkers, I started telling them my real dream: to travel the world with my wife.
And they scoffed. They straight-up laughed at me.
Are you crazy? they asked. You can’t get the time off to travel. Maybe if you work here for five more years.
These were true lifers, people who had decided this was their path, and they’d stick to it as long as possible.
Honestly, I respect their choice. There are lots of great jobs out there that pay good money and give you the security of benefits and a good job.
But after they laughed at me, I knew I had to quit. I knew I couldn’t work for years, decades, hoping my boss would give me an annual 3% raise and an extra week of vacation for Christmas.
So my wife and I sold everything we had, packed our bags, and moved overseas. We started in South Korea, teaching English to elementary students.
While I was there, I knew that if I didn’t learn how to become an entrepreneur, I’d have to come back and work my terrible jobs again where people would laugh at me when I told them my dreams.
So I busted my ass. Our day job teaching the kids was exhausting, but I still woke up at 5:00am most days to write and learn how to build a business. I worked nights, weekends, lunch breaks, and any spare moment I could get. I knew I had to become an entrepreneur if I wanted to achieve my goals.
Option Two: Become an Entrepreneur
This is the path that has made the most sense to me. If you’re reading this, I know you’re someone who’s thought about it, too.
When my wife and I came back from South Korea, I had managed to scrape together the foundation of a business. My first year, I made about $20,000. My second year, I made about $60,000, and I’ve been making more each year.
Entrepreneurship deals in every industry imaginable, but the common denominator is you. Can you survive the entrepreneurship roller coaster?
After reading countless autobiographies and studying the world’s most successful entrepreneurs, I began to realize they all had the same base traits:
- A desire for control and freedom that outweighed their desire for safety and security
You have to learn a lot to become an entrepreneur, which is where most would-be entrepreneurs quit. There’s so much to learn — sales, customer retention, product creation, good business practices, etc.
I’m a writer, but I was constantly surprised at how many non-writing skills I had to learn: Webinars, sales pages, email marketing, social media, networking, website coding. Now, I can afford to pay someone else to do all this for me (thank God), but for a while, it’s probably just you. If you’re not willing to learn, you probably won’t succeed.
The best part about entrepreneurship (besides the freedom and control and the impact you can make) is that effort scales. If you work twice as hard, you can get twice the money. Actually, you could get five to ten times the money.
There’s not really a ceiling for how much you can make — but there’s not really a floor, either. Your income doesn’t come from a boss or a company with an accounting department that sends you a check every two weeks; you get paid if you work.
Fortunately, you can start automating your business to start running on its own. For instance, once you create a product, you can keep selling it for years without doing much maintenance on it. For me, I’ve written books, created online courses, and self-led trainings that people buy every week, putting money in my bank account while I sleep and go to Disneyland with my wife and newborn daughter.
You can make a lot of money this way, and I’m already making way more than my old boss at my corporate job was, even though I’m 15 years younger. Best of all, I have far more free time, and work far less hours.
Of course, there are lots of ways to make a lot of money. Investing, stocks, real estate, horse racing.
But in a broader sense: you make money through customers or through your boss.
For me, I decided to put in a lot of work for a while — making products, building an audience, creating a business — so that later, I could relax and watch the money come in.
“Live like no one else now, so later you can live like no one else.” -Dave Ramsey
Entrepreneurship isn’t for everyone, but if you can survive through the ups and downs, you can build huge wealth really quickly — with lots more spare time than working for a boss.
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Entrepreneurship is scary but the rewards is worth it. I came here after reading your medium article and have already learnt a few things on how to structure my own business. Thanks for this enlightening piece.