It is weird to me that I have become the “older guy” in the room in most of my meetings. For most of my career, I have punched above my weight or age and have been promoted into the room with the “white hair” guys. My skill, ownership, and “get it done” work have always been rewarded. For years, I took pride in being that young guy.

Because of this trait, my rolodex—the  stormtroopers I have worked with—consists mainly of people older than me. In the second half of my career, I have typically brought good people with me when I go to a new company. Most of my value is knowing how to build a team, and I have used the main core building blocks a few times across different organizations.

Lately, my rolodex is shrinking—a lot. The people I relied upon are retiring. There is a specific kind of professional loneliness that comes with being the one who “stayed behind” to turn out the lights, especially when you’ve spent your career being the young, high-energy leader in the room.

In the end, there are only a handful of people that I have worked with for more than 10 years. Understandably, I am quite close to these people, as we have helped each other over the years and have really appreciated working together. We succeeded together.

I go to a few retirement parties each year. They always pull on a heartstring for me for one main reason: many people in their late 50s or 60s have worked at one or two places for the last 20 years or more. They have many people who are important to them to help celebrate this important retirement day.

I won’t have the 20-year gold watch ceremony. My career has been nomadic—a series of tactical strikes and rapid builds.  I realize my stability wasn’t found in a building; it was found in the few people who kept answering the call to join my next crew. 

At these parties, I end up wishing I had a more stable end to my career. So, the handful of people I have worked with longer than 10 years have become quite important to me. It is selfish, but it is tough to see them go.

The person I have worked with the longest, over four different companies, retired today. I worked with Carey for 17 of the last 20 years.  He was Chewbacca to my Han.  We don’t work together on my latest mission , although I told him he just had to ask. I knew he would not be joining me on this current mission, as his wife was having health issues.

We always worked very well together.

getting it done – old school way

Carey is the last one in my 10-year rolodex to retire—the one I spent the most time with and the one I am closest to.

Carey’s retirement isn’t just a friend leaving the workforce; it’s the final chapter of a specific era of my life. The book is closing, and the sequels will need a different cast.

I have had a bunch of people retire from my last Death Star in the last 2 years.  In the end, my core job at that Death Star, over the last four years I was there, was to make sure they had enough work to get to retirement. I moved people aggressively into different groups or spots where they could call their retirement days themselves. My former team has likely shrunk to a third of what it was when I started. Many of these people have retired or have announced their retirement this year. They have made it. I feel good about how I helped them. I am proud that this is my legacy at the old Death Star.

But Carey is different for me. He was my rock—the guy I depended upon to get stuff done without me even asking. We trusted each other, and we worked extremely well together. Work was his thing. He loved work, and I never really pictured him retiring. A few years ago, he moved across the country while still working for me. It means we see each other maybe once a year.

Carey is 63. We all get older. We all have life circumstances that are more important than work. I am happy for him, but I miss working with him daily. We still keep in touch, but there are no more battles to fight together. It is a sign that my time to do the same is not long off. I am happy for all the people I have helped get to retirement, but I am sad at the same time. It makes work for me less fun and is another sign that my time is soon.

So, congratulations, Carey, on your retirement. Soon I will join you, and then hopefully we can spend more time together reliving the good old days.

Thanks for all you have done for me over the last 20 years.  

And remember Carey. You promised me one last race one day.