I’ve always found it hard to resist the opportunity for adventure.
If you’d asked me five years ago what the biggest challenge of my life would be, I might have said becoming a dad, sailing across the ocean, or walking barefoot through the jungle.
And I would have been dead wrong.
It turns out, the toughest adventure I’ve been on so far was starting my own business.
After all, before starting Bluffworks, I:
- Sailed across the Atlantic.
- Walked barefoot for weeks alone in the jungle of Irian Jaya.
- Narrowly dodged getting nabbed by some nasty guys in Eastern Turkey.
- Hopped a freight train down the Columbia River Gorge.
- Married a girl who had a dog that bit me.
- Ran naked in front of Nike Town wearing only a pair of Nikes.
- Convinced Barbara Corcoran to launch my Kickstarter project.
- Worked so hard, I kept a sleeping bag under my desk.
- Let spell check miss-correct "warehouse" into "whorehouse" in client-facing documentation.
- Messed up a software configuration that caused a whole team of programmers to chase their tails for a day.
- Cried at work.
- Fathered a son whose energy eclipses mine.
- Wrote software overseas for $4 an hour.
- Stomped grapes all night for a ride out of wine country.
- Went on business trips where I shared a bed with my boss.
- Went on business trips where I shared a bed with bed bugs.
- Sat in first class without a ticket.
- Shoveled piles of cookies on the Oreo production line.
- Bought a black market video camera that turned out to be wet newspaper.
- Had my camera stolen right out of my pocket in Morocco.
- Dated a woman twice my age.
- Convinced my father-in-law I'm not a bad guy.
- Cheated on an exam to become nationally ranked in Latin.
- Knocked-out a bully with one punch.
- Learned to survive speaking only Vietnamese.
- Crashed a car driving the wrong way down a one way street.
- Went head to head in corporate politics and lost.
ENTREPRENEURSHIP is the toughest, most ass-kicking thing I've ever done.
After all the things I’ve done, how could I be so rocked by the journey of starting my own business?
I was puzzling this while deep in one of those “why is this so hard?” moments.
The answer? Because it is hard.
Because when you've wagered so much, the pressure can be unbelievable. In other high risk pursuits, I always have an out. (Boat sinks, get in the raft.) If there are outs after entrepreneurial failure, they are harder for me to see, so the wager seems much greater.
Because other risky things I’ve done have played to my strengths. In starting your own business, you are responsible for every function, including the ones you’re bad at, with limited resources and lots on the line. I have to excel at my strengths and my weaknesses.
Because the task is limitless. Most things you finish, you conquer, you succeed. With a business, once you succeed at one thing, you take on the next challenge, and keep going. The result is constant learning and mistakes, followed by re-group and re-attack.
Why is this hard? Because it’s real.
P.S. I’d love to know: What’s the hardest, realest adventure you’ve ever had? Share your real in the comments below, and let’s start a conversation.