Surround Yourself with Big Challenges

I go back and forth between Flatland (i.e. Connecticut) and the only "Gold Level" mountain biking destination in the world (Park City, Utah).

In Park City, we are surrounded by 400 miles of biking and hiking trails, and that's just right in town. Go over Guardsman Pass and you can access the trails surrounding Brighton, Solitude, Alta, and Snowbird ski areas.

So in Park City, I mountain bike. A lot. 

In Flatland, I almost never bike. It's boring. My wife and daughter go spinning, but that's inside, on a bike that doesn't move. I can't do it.

Here, it's easy to construct a ride that's just a bit harder, or more interesting, or - let's be honest, sometimes I need this - gentler than the beast you did yesterday.

Here's what I've learned: when I surround myself with challenges, I tackle them with relish. But when I have to invent a challenge, I don't do it.

To broaden this a bit into career terms, I see many people whose career challenges are as elusive as my Flatland rides. Perhaps you want to get "to the next level" but you are not, say, engaged in a three-month race to launch a new product. 

You're not really taking on a challenge; you are just thinking about it.

Let's get specific. Think about a sales person whose seemingly arbitrary annual quota is handed down from top management. Some years it's easy to exceed this quota, other years it is flat out impossible. So what challenge keeps her fresh and always reaching?

In most cases, the answer is: none.

Many years ago, I moved from a job at Ogilvy & Mather to one as a partner in a then tiny marketing consultancy. But it was led by Bob Dorf, one of the biggest-thinking guys I've ever met. Bob constantly wanted to double something, anything. He pushed me to hire faster, to sell more, to do two or even three jobs at once, and to ask our team to do the same.

Sitting in a client meeting with Bob, I'd be thinking we should ask the client for $50,000, and then Bob would ask for half a million - and get it!

Guess what? In three years, we grew from 10 to 150 employees.

Although at the time I often resisted his nonstop "full speed ahead" mindset, I've come to realize the wisdom of thinking like Bob: collect big, bold challenges like other people take multivitamins. Nothing less than one a day will do.

So whether you surround yourself with mountains or take a job working for a guy named Bob, you will benefit immensely by surrounding yourself with challenges. In the process, you will dig deeper, work harder, and achieve more than you think possible.

You'll spend less time thinking about your next step, and more time sweating and striving and succeeding.

P.S. You'll have a lot more fun, too.

Bruce Kasanoff writes for entrepreneurs, investors, and innovators. Learn more at Kasanoff.com.