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Dancing with Retirement

October 1, 2014
by Tim Tolan
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Tim Tolan

Last month my wife went to the St Augustine Amphitheatre to see Crosby, Stills and Nash on a warm summer night here in northern Florida. It’s great to see them still playing gigs—and like a fine wine they keep getting better. The concert was awesome and also surreal in so many other ways.

The first thing I observed as we walked into the venue was the crowd.  Multiple generations were present, but I couldn’t help notice that the largest demographic were those soon to be or already retired. I wanted to put myself into the younger demographic, but have to admit that, like everyone, I am definitely getting older. I don’t run from it. While I consider myself in the prime of my career, I have definitely reached an age where I contemplate retirement now more than ever.  Many candidates I talk to also bring up the subject and I always stop to listen, occasionally giving my own advice if I’m asked.

Like many of you, I’ve spent my entire career in healthcare and healthcare technology, and my network of colleagues and business contacts are the people that I converse with on a daily basis. It’s the space that I know well. Many of us know lots of people who we see at conferences year after year, read about in press releases or work with on a regular basis. That all changes the minute you retire, or at least it changes for most of us.

I have lots of friends who have retired and I always enjoy talking with them to learn how they are doing and how they are keeping themselves busy. I realize there are lots of ways that we can choose to retire and I don’t pontificate that one path is any better that another. What I do recognize is that you need to think about how to keep yourself busy, active and healthy once you retire. Your daily routine will be much different than the way you spend your time today.

Chris, a dear friend of mine, and I were talking a few months back about retirement. He retired a few years ago but still remains very active today.
He’s built his retirement around his life and the things he likes to do. For him its spending time with his lovely wife Marsha, sailing on their boat to the Caribbean during the cold winter months, playing golf, serving on the Architectural Committee of his neighborhood, enjoying his kids and grandkids, spending time with his aging mother, traveling around the world, working with start-ups and doing some consulting with me! He always keeps his hands in multiple projects that are interesting to him. He continues to learn new things that interest him and he gets to choose what he wants to do and when he wants to do it. He’s figured it out.

He told me about a party he and Marsha attended a few years ago. During happy hour he found himself talking to a few people he’d just met. Pretty soon the conversation turned to “So, what do you do for a living?” The minute he mentioned he was retired the conversation was redirected to others in the group who still had a work-related identity. Little did they know that Chris was a very successful investment banker who bought and sold over a hundreds companies in the healthcare revenue cycle market. His firm was the leader in that space for decades.

We tend create our own identity with the rest of the world based on what we do every day. Once we retire we lose that identity unless we reinvent ourselves and find other ways to keep learning and growing. That’s the reason I have elected to keep doing the things that I enjoy as long as I am having fun. True retirement would allow me to take a page from the playbook of my friend Chris. I too, want to do the things that I enjoy whenever I choose to do so. It’s that simple.

Retirement is what you make it, but requires a lot of thought and consideration to make sure you are happy and content with whatever you do.
My advice: Love life and enjoy doing what you want to do whenever you want to! It’s that simple. ◆

Tim Tolan is senior partner of Sanford-Rose Associates-Healthcare IT Practice. He can be reached at or (904) 875-4787. His blog can be found at