Can You Really Make Money Doing What You Love? 5 Lessons

Posted by | August 6, 2013 | Career Advice

This post is by Matt Wilson, co-founder of Under30CEO .

Recently, author Daniel DiPiazza wrote “An Open Letter to Frustrated 20 Somethings” on It blew up. Daniel’s premise: If it were up to him, why would he make a “job” or “work” the center of his life? When someone asks him “what he does,” why should he have to respond and narrowly define himself by the skills he uses to make money?

I’d spend my life traveling, learning languages, practicing martial arts, reading, programming, eating good food and (eventually) raising smart, open-eyed children.

Touché Daniel, and I agree: there is a better way. Now let me break it down for those on a quest to “do what you love” from someone who’s been through all the ups and downs already.

How We Did It

I graduated from Bryant University having built what the Collegiate Entrepreneurs’ Organization named the best chapter in the world, four out of five years. I was leading a team of 150 smart, young, innovative, passionate people. No way I was getting a “real” job after that.

So upon graduation, I pass up job offers galore to “start my empire” from my mom’s basement outside of Poughkeepsie. Pitching VCs, writing business plans, sending money to India for web development — and still without a clue about how to actually make money from my lawnchair. I call Jared O’Toole to drink some beers on the front porch and we realize there have to be lots of other young people trying to start businesses just like us. We co-found

With no revenue in sight, it’s now the dead of winter, and Poughkeepsie is getting depressing. Then the global financial crisis hits, and we’re really screwed. My mom comes to me shortly after Christmas to tell me that we will be losing our house. The home I grew up in.

Lesson 1: At least be able to tell your mom how your business plans to make money.

Suddenly, I question those $65k+ salaries I turned down. But it’s time to hustle. I accept the first job I can find on Craigslist, a position for a driver, and show up at 6 a.m. Wheeling and dealing can’t be so bad, I think to myself. It’ll be my mobile office.

Wrong. I show up and am given the keys to a dump truck. With an 18-foot trailer. I guess it’s time to learn to drive a dump truck.

I get us to the job site, where I’m quickly informed that the crew of laborers I’m driving around aren’t going to appreciate it if I sit in the truck. Time to dig ditches 12 hours a day for the next six months.

Lesson 2: When you put your back against the wall, you make things happen.

Sure, I could have let go my entrepreneurial dreams and gotten a cushy desk job. But instead, I put myself in the most uncomfortable situation possible. Digging ditches with guys who could work me under the table, and then going home to moonlight …read more

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