Nothing like a high school reunion to put exit planning into perspective

A couple weekends ago I went to my Madison East High School class reunion. It was the first reunion I had been to in many decades, so I wasn’t sure what to expect. My recollections of high school are rather fleeting, remembering more of the overall activities and people I was involved with rather than specific occasions. In a game of “remember when,” I’d be sunk.

It was a fun evening. (The classmates who orchestrated the weekend activities did a fantastic job, so a shout out to Lisa, Steve, Tony, and Mike!) John discovered that he was married to Molly in fifth grade during recess and was gracious enough, with his current wife standing by him, to offer the spare bedroom to the new family member. Kate led the group in the school pep song, complete with reenactment of the cheer routine. Dave played in the band, providing kick-tail music for the night. We caught up on what had transpired over the years — raising kids, updates on parents that served as our surrogates, and so on.

It struck me that we were all in the same boat we were in on graduation day all those years ago. Only this time, we’re facing leaving our careers and organizations we have grown and/or contributed to for many years. We aren’t Social Security age yet, but by the next major milestone reunion we will be. We are facing important decisions about succession planning, retirement, what is important in life, and what our next chapter holds. For example:

• Grow or go? There are some peers who are starting to wind down their careers. Some by choice and others not. The rest of us are thinking about it. It’s a big decision. One classmate, Sue, and I talked about this dilemma. She is going for a new opportunity that would challenge her and demand putting more energy into her work while she watches friends start to slow it down. She still has gas in the tank and wants to grow the organization, as well as her own capabilities. But what if she ultimately does not move into that position? Will there still be gas in the tank to do something else? If we aren’t growing, we are by default “going.” Which are you doing? What’s a meaningful contribution? These are questions we all need to ask ourselves every day.
• Fond memories: I was not the only person failing the “remember when” game. We acted almost as translators, filling in gaps for one another all evening long. Not unlike co-workers, my classmates carry a ton of information around in their heads that only they know or remember. Wouldn’t it be cool if we captured the stories, adventures, and lessons from way back when? However, the difference between our classmates and our co-workers is that it’s vital that the business get that knowledge documented and shared. For your class, it’s fond memories. For your business, long-term viability and a strong valuation depend on it.
• Relationships: After the event, I caught up with a friend who attended festivities on a different night. We both spent the most time talking to people who we had gone through school with since elementary days, even if we ran in different packs in high school. The conversations where we felt able to pick up where we left off were with our elementary buddies rather than our high school-only gang. The foundation and depth of those relationships endured. As we consider retirement and/or selling our businesses, the depth of our relationships helps us navigate our uncharted waters. Being in the same room with these people reminded me that none of us needs to do it alone. We can reach out to people we know to point us in a direction, help us build our team of friends, mentors, and advisors, and talk through issues we’re facing in the process.
• What’s important: Let’s face it, high school is so, well, high school. There are the brainiac’s, jocks, cool kids (aka “socies”), greasers, etc. It’s full of social landmines for every kid in that class — even the “coolest” one. Decades later, labels largely fall away as the facades fade. Conversations are more open. We admit successes and failures, health scares, or family losses. There is honesty. This honesty recognizes we are — again — all in the same boat. Our human connection is more important than projected image because our time is limited. So let’s make it meaningful — whether in a conversation that night or how we wake up and face the next day.

I got all this from one evening at a high school reunion that I was frankly ambivalent about going to. I’m glad I did. The experience frames my own eventual exit plan, as well as provides glimpses into how others view these preparatory years.

What about you? Did you go to your last reunion, or do you have a one coming up? Try going to your next one; you might be wonderfully surprised.

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