Colorado and the Importance of Traveling With Friends

When I originally started to write this post, it was going to be about the amazing adventures I’ve had over the years on my annual snowboarding trip with a group of close friends.  The amazing powder at Beaver Creek’s Glades.  The time we road Park City during the Sundance Film Festival.  And of course when we found a karaoke machine tucked away in a closet in our AirBnb and we were up until 4am singing horrible pop songs to a stuffed bear (that story will be for another time). 

But every version I started to write all came back to one common theme, the importance of traveling with friends. 

I travel.  A lot. Sometimes it’s for work, other times for pleasure and sometimes it’s just to get away for a few days, either way, I seem to always be on the road.  But year over year, there’s one trip that I always look forward to just a little more than all the all the others and that’s my annual snowboarding trip with “the guys.” 

Eleven years ago Mark, Seth and I decided to plan a snowboarding trip to Colorado.  Little did we know at the time that this trip, despite everything else we had going on in our lives, would be the catalyst to keeping our friendship alive and strong over all these years.

As we’ve grown older and as responsibilities, expectations from our bosses, wives, kids and really just life in general has taken a higher priority in our already overflowing digital calendars,  we’ve found that taking the time to put all of that aside and to be with each other has become increasingly important.

I recently did a search of what people regret most of life and death and the top result was for a book written by Bonnie Ware, a palliative care nurse, called “The Five Regrets of Dying”.  In the book she talks about her experience caring for those on their literal deathbeds and she writes about the things that they regretted the most about their lives.  Although somewhat morbid and most definitely sad, we all have the opportunity to look at our life and not make the same mistakes that many have before us.

To save you from reading the entire book (although you should), here’s the list as she lays it out:

  • I wish I'd had the courage to live a life true to myself, not the life others expected of me. "This was the most common regret of all.
  • I wish I hadn't worked so hard.
  • I wish I'd had the courage to express my feelings.
  • I wish I had stayed in touch with my friends.
  • I wish that I had let myself be happier.

You see, it’s so easy to get caught up in the grind of life. The endless emails.  The oh so popular “hustle” that seems to be increasingly popular these days.  But to really be intentional about how you’re spending your time. To think about what you’ll be thinking about on your deathbed and if you’re living the life that you want is a hard thing to do. 

When it comes down to it, we all have what it takes to look at the lessons and regrets of those that have made the mistakes in the past and not repeat them for ourselves.  Those that have looked back on their lives and  wished they’d done things differently.  We each have the power within us to make those changes now. To not wait until tomorrow, or the next day, or until it is us on our respective deathbeds wishing that we’d taken the time to allow ourselves to be happier.  To say “yes” to that adventure.  To reach out to that friend.  To put work aside, if only for a few days, and do what makes us truly happy.

When I think back on these snowboarding trips, over time I’m sure I’ll forget about all of the small details about whether we had good snow or bad, how much I spent on a lift ticket, what mountain we road on what year, but what I will remember is that for all of those years I made the decision and was intentional about taking time away from everything else and spend that time with those that I truly care about. 

And that is what I will remember and why each and every year, no matter what, I will make sure that I take the time to travel with friends.


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