Last month, I went out to dinner with some friends. One friend announced to the group that, after working for a large telecommunications company for more than 25 years, he was being offered an opportunity to retire early with some very nice incentives. He further informed us that he had intended to retire within the next year. So, the offer was not going to change his planned retirement date in any significant manner.

Nevertheless, he seemed paralyzed about whether to take the deal, fearing he was not as ready to retire as he had thought. Wanting to offer helpful insights, I probed deeper, asking him questions involving three key areas:

  • Status: I asked, “Is your identity tied very closely to being an upper-level manager at your well-known, prestigious company?” He said, “No.” He wouldn’t have any problem meeting new people identifying as a retired executive. His ego was a modest one. He was not going to be particularly concerned about what others thought about him now that his relevance in corporate America would be over. Not a biggie.
  • Engagement: I then asked, “On a scale of 1-10, how much enthusiasm and passion do you have for his job right now?” His response? “Somewhere around a 5.” Not much fire in the belly, but I suppose it could have been worse.
  • Vision: Finally, I asked, “What do you think you will do when you’re no longer employed?” “Initially, I’d do more woodworking,” he said. He very much enjoys it. In the past, he has been involved in some serious projects. It would be nice to devote more time to this long-time hobby he said.

All three answers led me to confidently say, “You’ll do just fine in retirement. Take the money and run. Quite frankly, you’d be a fool to walk away from such a generous offer.”

Where Do You Stand on These 3 Areas?

If any of the following statements sound like you, be prepared for a very rough ride if you’re close to retirement.

  • “You mean the only relevance I will have to the legal profession is the occasional pro bono case that I may do. Who’s going to be impressed with that?”
  • “I just love doing deals/I still love the fight. I still get a high when the deal gets done and I see the smile on my client’s face.”
  • “I don’t remember the last time I took a vacation, and billing 50 hours a week hasn’t given me much time to even think about what I will do. Practicing law is the only thing I know. I suppose I will figure it out once I have all that time on my hands.”

Take a Lesson From My Friend

Bottom line: Retirement works well for those who, during retirement are content with their new identity and are enthusiastic about doing something besides practicing law. Do yourself a favor and take a lesson from my friend. Start dreaming about what you can do in retirement now. Because if you don’t, you better worry—you won’t be happy.