A Whole Different World

Years ago, in what now feels like a whole other life, I worked for several startups as a computer programmer and project manager.

Back then, I thought it was great.

I was fresh out of college, and I earned a lot of money relative to my expenses at the time.

I traveled frequently and spent an entire summer in Austin, TX working at a large company where the 40+ managers had all bought matching Porsches (and moved to a larger office so they had a parking deck to put them in). That office was insane, too - pool tables, ping pong, foosball, and dozens of vending machines that didn't require any money.

Later, I worked at another firm where I could travel back and forth between offices in several cities. I had a large staff, an expense account, and all the trimmings that come with it.

In between, I worked with other startups, sometimes as an employee and other times as a contractor.

In every case, life was great.

Until it wasn't.

Scouring the web today, I can see that of those companies, only one is still in business.

The rest folded due to poor management and terrible decisions.

I remember a time at one company where we watched the top manager remodel his [already luxurious] office during the same month he announced layoffs.

The reason?

Budget constraints.

When the last company I ever worked for folded, I knew I needed to get myself a position where my income and - more importantly - my future were not dependent on some old codger who needed a fancy leather couch even though his company didn't have enough money for payroll.

It's been a wild ride since then, akin to a massive roller coaster with giant ups and downs, sharp turns, and more than one upside-down loop.

Many times, I didn't think I'd make it.

Hell, I'm still not always sure I will make it.

But as I sit this morning overlooking this beautiful pond as the sun rises and the world comes to life, I wouldn't trade it for anything.

Running your own gig comes with a lot of risk, uncertainty, and sometimes a buttload of anxiety.

It's a whole different world.

But one in which, once you get "over the hump," comes with an unmatched level of freedom.

My good friends Carl and Elizabeth Hamilton recently found themselves in the same place I was 20 years ago and made the same decision as I did back then.

Their company, CSC Construction, is now handling our renovation work at House Partners.

I'm excited to have reliable contractors who show up on time and get the work done.

But I'm even more excited to watch their journey.

Stepping away from the security of a regular paycheck is terrifying. So much so that for a long time after I reached the point of earning enough money to cover my living expenses and start saving, I had a voice in my head telling me to "get a real job."

Dozens of times, I nearly bailed.

I'm glad I didn't.

Carl and Liz are having those same conversations, I'm sure.

"Can we do this?"

"Is this the right thing?"

"Will we make it?"

I remember those days well.

And like watching the sun rise over the pond in this beautiful park, I wouldn't trade them for anything.

Because it's absolutely worth it.