Choosing what stays
When I announced my retirement from The Hartford at the end of 2023, I thought I had a pretty good sense of what the next chapter would look like. Once my retirement officially began, it didn’t take long for new opportunities to arrive. Almost immediately, the University of Connecticut School of Law asked if I would teach Principles of Insurance as an adjunct professor. It felt like a natural way to stay engaged, share what I’d learned over the course of my career, and explore something I’d never done before. I was excited to say yes.
By early summer, I was immersed in preparing for the fall semester. I enjoyed developing the course and working with the students, but I quickly realized teaching required much more preparation and structure than I had anticipated. Once the semester began, it also committed me to a regular schedule, something I hadn’t fully appreciated when I accepted the opportunity.
When the semester ended, I decided not to teach again, at least for now. I don’t regret saying yes. In fact, I’m glad I did. Retirement has given me the opportunity to experiment, learn what fits, and adjust accordingly. Maybe I’ll come back to teaching someday, but right now it isn’t the right fit.
The experience reinforced one of the biggest lessons of this season: sometimes the value comes from trying something new, learning from it, and giving yourself permission to make a different choice.
A portfolio with purpose
I didn’t walk away from everything when I retired. I carried forward a few community boards, including one
quasi-governmental organization focused on development work for the City of Hartford. I’m also serving on the board of a private, for-profit insurance consulting company and working with my former CEO on a long-term community initiative to develop a 20-year vision for Hartford by bringing together public- and private-sector leaders to think about the city’s future.
Professionally, I added consulting work with Bain & Company, advising clients on insurance, government affairs, and in-house law department issues. It lets me continue working on complex problems, stay current on what’s happening in the legal profession, and collaborate with younger professionals. I’m also part of another consulting group that serves as a confidential sounding board for general counsel as they navigate difficult or sensitive issues. Those one-on-one conversations have been especially rewarding.
Taken together, it has become a portfolio of interesting work that continues to evolve—not dramatically, but intentionally. Every time something new comes along, I ask myself a simple question: If I say yes to this, what am I willing to give up?” That question has become one of my best filters.
Protecting space
One of the things I value most about retirement is flexibility. Shortly after I retired, my wife and I spent five weeks in Paris to decompress. We’ve taken long weekends to visit our daughter in Annapolis and sons in Boston and New York City. Sometimes we simply decide to do something because we can. I don’t want to lose that freedom.
As I’ve considered new opportunities, I’ve developed a few personal criteria. First, I don’t want anything that locks me into a rigid routine or requires me to be in one place every week. Second, it has to be something I’m genuinely interested in. I’ve spent decades working on issues that mattered to me, and I want to continue that. Lastly, I have to believe in the mission.
Today, I find myself weighing opportunities across several dimensions: the work itself, the organization’s mission, whether I can meaningfully contribute, my own well-being, and whether it preserves the flexibility I’ve worked hard to create.
My MyNextSeason Advisor helped me think about retirement in manageable pieces instead of feeling like I had to design the rest of my life before I walked out the door. His advice was simple: you don’t have to plan the whole thing at the beginning. Give yourself permission to explore, be discerning, and see what feels right. That perspective stayed with me. It’s much easier to add something later than it is to extract yourself from a commitment that no longer fits. Protecting that flexibility has become just as important as pursuing the next opportunity.
When the title goes away
Like many executives, I worried about relevance. Before I retired, I knew that if I reached out to a Chief Legal Officer or another industry leader, chances were good we’d connect. Part of that came with the role I held, and I understood that would naturally change once I stepped away.
What has been encouraging is discovering how many of those relationships have continued—not because of a title, but because we had built genuine connections over many years. People still reach out for ideas, introductions, or simply another perspective on an issue they’re facing. That has been a meaningful reminder that while my role has changed, my experience and relationships still have value.
In fact, I probably network more today than I did while I was working. Three days a week, I usually have several coffee meetings. I keep a running list of people to reconnect with, especially when I’m in New York, and I make an effort to stay in touch. Those relationships continue to enrich my life personally while also opening doors to meaningful opportunities. Retirement has reminded me that while roles change, strong relationships—and the experiences behind them—have a way of lasting well beyond a title.
Making room for what comes next
I’d be lying if I said I never questioned whether I retired at the right time. Like most people, I worried about money. After decades of accumulating, shifting to spending feels unfamiliar. There were nights I lay awake wondering whether I should have worked another year or two. Then I remind myself why I made the decision.
I needed to make room for the next generation of leaders. My team deserved the opportunity to step into new roles, and if I had stayed, many of the experiences I’ve enjoyed over the past year simply wouldn’t have happened. Visiting my kids for a long weekend, having the flexibility to travel for weeks at a time, taking on work because I wanted to rather than because I had to—those experiences have confirmed that this was the right decision for me.
Sometimes I’ve thought, why don’t I just walk away from everything and play golf every day? But the answer quickly surfaces: that’s not who I am. I still enjoy solving problems and contributing to a larger organization or community. I still believe I have something to contribute, and I still value the relationships I’ve built over the years. The difference is now I get to choose how I contribute.
Slow down first
If there’s one piece of advice I’d offer, it is to give yourself permission to slow down before you speed back up. Take three to six months to decompress. Think about what energizes you and what you don’t want to carry forward and be very protective of your time.
Trust that if you’re staying connected and putting out feelers, opportunities will come. You don’t have to chase every one of them, and you don’t have to get every decision right the first time. Sometimes you need to try something to discover it isn’t for you. That doesn’t mean it was the wrong decision; it simply means you’ve learned something about what you want your retirement to be.
One practice my wife and I have adopted is sitting down together a couple of times each year to ask ourselves, “What are our priorities right now? What do we want this season to look like?” We talk about what we want to do together, what we want to pursue individually, and how we’re spending our time. Time has a way of filling itself. Being intentional about how you spend it—both together and separately—may be one of the greatest freedoms
retirement has to offer.