Reconnecting with Life-Long Friends

By Sean Flynn

If you find yourself sharing these or related sentiments, it’s a pretty good sign that you are reconnecting with a friend. These are the rewards for reaching out unprompted to a good friend, maybe from your hometown, school days, or early career stops. Someone who knows you has seen you at your best and your worst…and still “has your back” in a way that can be challenging to find as life goes on.  

Life has a way of coming at you fast and throwing the occasional hanging curveball. For me, it was the loss of my best friend and Best Man at my wedding to a heart attack at 49.  I can’t do justice to it here. Suffice to say, it was like losing a brother.  

I am now at the point where I smile first when I think of my friend.  And, like so many of the gifts he gave me in life…he had one more lesson to teach me…and that was the value, the importance of those friends, those bonds that we all forged as we grew into the people we are today.  

I made a commitment to reach out to those that had been athletic teammates, college roommates, and peers/mentors from early career stops.  It was a bit odd at first, finding people on Facebook, LinkedIn, or old mobile numbers.  But, it got easier as I got rolling, and it has been among the most fulfilling ways to find work/life balance that I have ever found.  

Along the way, I learned a couple of tips:

  • Be proactive.  Reach out unprompted, and know it may take a cycle or two for it to be reciprocated. Remember, you are re-entering the rhythm of the relationship.
  • Share why you are reaching out and how important the other person is to you.  Show sincere gratitude for the experiences and friendship shared.
  • Wherever possible, find a way to connect with them in person.  Phone calls and zooms are phenomenal but still not as powerful as a meal shared, a ballgame or concert attended, a quiet drink, and more. 
  • Don’t look for anything in return, just the opportunity to reconnect.  No expectations but a little bit of time and a smile. 

I can’t promise you every reconnection has the same magic.  What I can promise is the joys of this particular journey are real and limited only by your imagination and time invested.  I can also say that when people ask me what I like to do when I am not working…catching up with old friends is at the top of the list.  

So, the next time you find yourself thinking, “when was the last time I saw…” a friend from earlier days…reach out.  Tell them how much their friendship means to you, and share a laugh.  It is, to borrow a phrase, chicken soup for the soul.  😉


Throughout the “Top Priorities” section of this blog, we will provide data-backed insights for a long, active retirement.

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