Anyone can hold the helm when the sea is calm. — Publilius Syrus

This quote reminds me of my younger days — I loved water skiing and wasn’t half bad. My siblings and I had our own slalom ski, which was bright blue with rainbow graphics. You should know that getting up on a slalom ski while being pulled by what was primarily a pleasure boat wasn’t easy — so once I got up, I knew I had to make the most of the opportunity.

So each time there was a decision: Would I:

1. Play it safe, stay inside the boat wake, ski longer, and enjoy the view?
2. Push my limits, jump the wake in the air and risk a fall?

Most of the time I opted for number two. As my arms were going to tire anyway, I figured I may as well go down in a spectacular fall.

To be sure, my falls looked far less graceful than I hoped, but I felt accomplished if I ended with a wipeout. Far better to go down in a blaze of (imagined) glory than to just let go of the rope and drift into the lake.

Three Business Lessons I Learned From Skiing

1. If you don’t push the envelope, you don’t expand it.
   [Tweet “If you don’t push the envelope, you don’t expand it.”]
   Every time I jumped the wake, I felt a little more confident and jumped a little higher than the last. By August I was always better than I had been in May. Are you stuck doing the same things and never trying anything new? Learn a new skill or go to a conference session you think is over your head. If it doesn’t work out, you’ve wasted a bit of time, but lost virtually nothing.
2. Falling can hurt. I pulled a muscle or two in my (sort of) heroic efforts, but while my body was unhappy, my psyche felt amazing. Waking up the next morning with a bruise or a sore hamstring reminded me that I had tried something new and stretched my abilities. Even if your experiment doesn’t work, you now know that it doesn’t work. We learn more from failure than success, so take note of the lesson in the fall.
3. It’s much more fun. The more we master a skill, the more we enjoy it. We begin to think more creatively about it, push ourselves, and consider new possibilities. I remember thinking, “I wonder if I could hold on with one hand … ” The answer was, yes, I could hold on with one hand. And it felt so, so cool. We’re all better at what we enjoy, what challenges and stimulates us.

There are times when it’s appropriate to play it safe, and times when it’s right to risk it and go big. Only you can decide which is right for any given circumstance.

But resist the urge to play it safe most of the time. Have fun. Learn more. Stretch your limits. Yes, it’s scary, but it will be less scary next time. Do it. And be sure you look as cool as I (thought I) did when you fall.