Time For What’s Next

On December 31, 2024 I will be retiring from the investment business after 42 years. I made the decision over a year ago and am now making that decision public. I will be selling my business to Blaire Greenwood and Allison Lane of Greenwood Financial Group, people who happen to be two of my dearest friends in this world. I’ve known them both since they were annoying toddlers. Now they are annoying grownups who I love dearly. Knowing that they will be the ones taking care of my clients in the future has made the decision to retire much easier to make.

So, why now? Lots of reasons, really. First of all, it’s very hard to do anything for 42 years, but even harder to stop doing it. It becomes ingrained into who you are. But my line of work is the sort that you can’t do just a little of. You have to be all in, all the time. The business is fast moving, constantly changing—an ever evolving and chaotic enterprise. The regulatory regime that has risen up around the business has become oppressive, keeping up with the mountains of compliance edicts have become a full time endeavor in and of itself. There isn’t a place for part-timers. At the end of the day, I would just rather be at the lake in Maine.

2023 wasn’t my best health year. Had a scare or two that required several tests and medications, and also caused me to ask myself some questions like, “why the heck are you still working?!” My cardiologist informed me that the way that the human body handles stress at age 66 is far different than the way it handles that same stress at 36. He suggested politely that maybe my body was trying to tell me something. I have listened.

It’s ironic that I have made a living helping other people prepare for retirement but now that it’s my turn I feel apprehension. It’s not the money part that brings anxiety. It’s more like how do you replace a 42 year career? The answer is that you don’t. You transition to something less consuming, less burdensome, more relaxing. You find ways to embrace your new freedom. I’m confident that I will, mostly because I’m absolutely sure that this is the right decision for me. That doesn’t mean it will be easy. It also doesn’t mean that it isn’t a little scary.

Here’s the part about retirement that I don’t like. First of all, I hate the word. To retire from something is to withdraw, to quit, to disengage. All of those words sound like surrender to me, like giving up. That’s not me, it’s not who I am. But, there it is, staring you in the face. You spend four decades building something with your bare hands, making something valuable out of nothing, then you realize you can’t do it anymore. You turn over the duties and responsibilities to others, younger people with more energy, more drive. There’s no other way to spin it…you’re quitting. But quitting isn’t always bad, right? I mean, after the first bowl you quit eating ice cream. No matter how much you might want a second bowl, you quit because eating a second bowl would make you a pig and you would regret it the next morning when you step on the scale.

The worst part about this notion of “retirement” is the idea that naturally flows from it…that your best days are behind you. Suppose retirement really means that you have already done the best work of your life? That there are no more dragons to slay? If I ever get to the point where I believe that there is nothing great left for me to accomplish, I’m going to be in trouble. The task on the morning of January 1st, 2025 will be to find it.

I will not miss the constant, never ending, relentless pressure of the equity markets. I will not miss the sometimes crushing burden of responsibility that comes with being a trusted advisor to nearly 300 people. But, I will miss the people I work with, their friendship, the feeling of camaraderie, being part of the shared struggle.  I will miss my clients, many of whom I consider like friends and family. But, it is time. Time for what’s next.