Below is an email I sent to all Benefitfocus associates

The best thing about our country is the freedom we enjoy. Where else can you get into a car (that you own) and drive for 1,000 miles without asking any permission, being searched or even feeling like someone will notice? Not sure why I think about that so much, but I do. I am always in amazement at the distance we can go with essentially no interference. Perhaps because I have traveled to a bunch of countries that do not allow you that latitude. Or perhaps because I feel the most personal value in being able to roam.

As a kid I always wanted to own an airplane when I grew up. My dad had a plane when I was a kid. As a matter of fact, he got his private pilot license the month after I was born and took me up when I was 3 months old. As early as I have memory, I have images of looking out of the window of a small plane down on the houses and farms. Seeing a swimming pool was like, the coolest thing. Today when I fly, I still press my head against the window and stare down at the patches of land. As far as I can see there is freedom. A plane does that for you. It doesn’t cancel gravity or the pull of the earth, but in a rather clever turn of physics, it counters it with something called lift. If you have lift equal to or greater than the weight of gravity, you can come off of the ground. And when that lift gets you up over 1,000 feet or so you can really get a sense of what freedom is all about.

This morning when I departed from CHS and on my way to Boston, we flew right up the coast and over NYC. I am visiting a customer today, discussing business, doing my job, listening and all of that. I’m not sure there is another place on earth that would allow me to travel so freely for either business or pleasure. We all know the hassles of modern airport security, but in context of how far you can go and how fast, can you see through those hassles for a bit and into the amazing room we have to roam?

There are so many issues with our country and so many people pointing them out all day long. I suppose I could lament those broken things like the rest. But for me I tend to dream about the bigger and more positive things. I am even “too optimistic” as someone recently labeled me. I suppose when I am gone if people want to sum up my life as too optimistic, then that will be just fine with me. While I am here I think I’ll just take a moment to look out the window of this plane and marvel at this magical land I was fortunate enough to be born in. For a guy who has a heart for dreaming and two wide eyes that love to see the open horizon, I’m thinking this country is a pretty darn good spot. I still cry every time I hear the national anthem when they sing, “...the land of the free...”.

Next time you get on a plane or hop in your auto, maybe you’ll join me in being too optimistic. Maybe, just maybe, you’ll drive past that exit that takes you home and take your freedom for a spin. It’s right there under your seat. Fill up with some gasoline and go for a ride. A bunch of people gave their lives so we could see this amazing place. Get out there and check it out.

Shawn From 36,000 feet