Personal Risk Management Planning at the Next Level

Skiing with my old friend, Steve, always turns into a few days of regurgitating the iconic Clint Eastwood line: “Do you feel lucky?” This trip to Vail would be no different.


Steve made his fortune managing money on Wall Street and ultimately decided a life pursuing the best beaches and ski areas the world has to offer would be much more fun. I am always happy to get his phone call with the invitation to the next great destination, although I always check to make sure my insurance policies are updated before going.

Standing at the top of Vail, I soak in the view across the snow-capped Rocky Mountains, my adrenaline rushing in anticipation of that question from Steve. “Let’s head over to Highline,” he says, followed by, “Do you feel lucky this time?”

“No luck needed,” I reply. “I do recall you paid the tab last night at the Red Lion because you felt the need to eat some snow yesterday on this same trail. Same bet as yesterday?” I ask.

“You’re on!” he replies with a toothy grin.

We work our way across the mountain top and arrive at the crest of Highline. This is a double diamond (extremely difficult) trail that runs under the Highline Express Lift on the Front Side of Vail. Looking down from the top, the terrain seems to roll out and fall from underneath us. The moguls look like miniature mountains, littering the trail all the way to the bottom. The snow is plentiful and the bumps on Highline ...

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