I Found the Secret to My Happiness!

My first job out of college was in sales. I made $33,000 in six months selling ads at Careerbuilder.com. I was making excellent money for my first year out of college. I had a new car, girlfriend, cool apartment, new clothes, and lot’s of friends. I hated it.

Mostly, I hated waking up at 5:30 in the morning so I could get to work by 7am. I hated the one hour commute to work and the hour and a half commute home in Chicago traffic.

I was one of the top sales people in the company, only to be constantly ridiculed and pressured by my bosses. I hated pointless corporate sweatshirts and tote bags that I’d never wear use. I hated the “business casual” clothes. I hated wearing socks.

Mostly, I hated the stress of working 12 hour days, just so I could make other people wealthy. Why couldn’t I invest those same 12 hour days into me?

So I quit…

Six months after getting my first job out of college and I was done with corporate life.

The day after I quit, I started calling businesses in the phone book (it was 2003) to ask if I could build them a website. I dabbled in web design in college, so I knew a thing or two; and that was more than my potential customers. Wouldn’t ya know, the first person I called said yes!

Over the next year I made about $15,000. It was only about 20% of what I was making at CareerBuilder. But I was 10 times happier. It was so wonderful.

That wonderful feeling should have been a hint as to what really made me happy. But I think the wrong message was sinking in, so I started to grow.

Within 5 years, I went from building a few websites in my apartment to having a full service digital marketing agency on Michigan Avenue. I had 30 employees and was working with some of the biggest brands in the world, including CareerBuilder.

Then, oh shit…

I wasn’t happy again. I was working 12 hours a day, making a ton of money, and I was the boss. Why wasn’t I freaking happy?

I was imprisoned again in Corporate America. Sure, I may have built the jail cell, but I was also somehow an inmate. I couldn’t escape. My employees and customers needed me every minute of the day. I was the business. The business was me.

The Secret to My Happiness

By 2014 I had money, a successful digital marketing agency, and a gorgeous girlfriend. But I wasn’t free. I couldn’t wake up when I wanted to wake up. I couldn’t work on what I wanted to work on. I couldn’t go on vacation, and I couldn’t not show up for work, ever. My agency’s success depended on me running the operation. I was the captain, the coach, and the most valuable player.

Thankfully, my agency was doing very well. I put the word out that I wanted to sell my business and I immediately had a buyer. By the end of 2014 I was out. My agency was successfully acquired and I was totally free. Free to do what I want and when I want to do it.


There’s no substitute for hard work. I still worked my butt off, but I made sure my freedom was #1. I started a new software company with zero overhead, except a part-time software developer, who later became a partner.

I worked from different coffee shops around Chicago, the rooftop of my building, outside on restaurant patios, the beaches of Florida, and wherever the hell else I wanted. After all, I was free.

Within two years, my software company sold for well-over seven figures. The reason I’m telling you this is because once you have a nest egg like that it dawns on you. Money doesn’t make you a happier person. Being free to do what you love makes you a happier person.

I stopped listening to society, friends, and family. They mean well, but most of them are hopelessly immersed in their own world, from which there is no sign of escape. And the more people who are immersed with them, the better they feel.

Right now, I’m writing this article from Barista Parlor, a coffeeshop somewhere on the east side of Nashville. My wife and I are spending a month in an AirBnB while we work from coffee shops. And I’m able to do this because I’m free to do what I want to do, how I want to do it, and when I want to do it.

Freedom is the secret to my happiness.