Dear Amber,

It is my hope, while you’re still just 19 years old, that you take these words to heart.

I don’t want you to marry a guy that has a job.

You see, there are some things I’ve never told you about me.  Nearly thirty years ago (yeah, back in the 1900’s), I was a middle school kid with ambition.  I bought one of the band kids’ fundraising candy boxes, filled it with my own candy that I bought from IGA, and sold it for a month for some pretty nice mid-eighties profit.

After that, I discovered baseball cards.  I bought and sold them during study hall and had more money than most of my classmates.

As high school neared an end, my parents told me I had to get a job.  In fact, their exact words were “Don’t come home until you have a job.”  As children of the WWII generation, they were taught that the best life path is to have a job, a 401k and a padded savings account.  Stability and security – that’s what they said I needed.

For seventeen years I kept that boring, yet high paying job because I felt secure, I could pay my bills and feed you and your brothers.  In the late nineties I started a ‘side gig’ to make some extra money, fixing computers and building websites (yeah, way back then).  Those old voices of fun and profit kept trying to get out, but each time I rationalized them away.

In 2008 I discovered a book called “The Four Hour Workweek” that changed my life.  And because of that book, it became my objective to quit my job – something I finally did in 2010.  Why? Because the entrepreneur in me just had to get out, and it’s the best decision I ever made.

But enough about me – we’re talking about your future husband here.

So what do I hope you’ll do? I hope that you don’t get tangled up with a guy with a job. Guys that go to work are drones – boring and lifeless.  They have no future, other than working their asses (and their hair) off for 40+ years to then enjoy their time with you.  What fun is that?

Guys with jobs and steady paychecks also dictate your financial future – there is a set income and a set lifestyle that you’ll never get beyond.  Sure, a 3% raise here and there and someday you’ll be able to afford a decent home, but in the overall scope of your overall finances, you’ll be stuck in a rut that will have you craving small wins from scratch-off lottery tickets and slot machines.  Trust me, there’s no future in either of those.

Instead, for me, find yourself an entrepreneur.

You need someone that, like in the Fleetwood Mac song, will go their own way.  Think about it – anyone crazy enough to buck the system and make their own future is going to be way more fun to grow old with.

Find a guy that sees potential in odd things.  Find a guy that always wonders if there’s a better way.  Find a guy that, like you, enjoys taking risks.  Calculated risks, that is.

Yeah, there will be ups and downs. Probably more drastic ups and downs than a guy with a steady paycheck, but I think you’ll be a happier (and perhaps richer) person when you look back over your life.

This is my hope for you as I get older.  Don’t settle for mediocre.

I love you,
Dad