Until the final months of his failed 2013 campaign for reelection as mayor of Rochester, N.Y., Thomas Richards enjoyed a charmed career. He repeatedly leveraged legal jobs into executive posts—from litigation partner to managing partner of what is now Nixon Peabody; from general counsel to CEO of the local energy utility, which cut him loose with a $10 million golden parachute after a merger; and from Rochester city corporation counsel to mayor, a position that he won in a special election when his predecessor became New York’s lieutenant governor.

Then, in his bid last fall for a full term as mayor, the 70-year-old Richards stumbled. After a half-hearted campaign, he lost the Democratic primary; days later, his 37-year-old son Matthew, a father of two, succumbed to cancer. When supporters mounted a third-party campaign to retain him, Richards seemed ambivalent, producing political chaos that cut against his reputation for steady, businesslike leadership. His real struggle broke into view at one contentious press conference, where he snapped, “Do I want to be mayor? I want to be a grandfather more.”

Shortly before Richards left office at the end of December, he spoke with American Lawyer contributing editor Mark Obbie about juggling law and management, walking away from a job and redefining his own work-life balance.

The American Lawyer: Young lawyers don’t usually dream of managing a law firm, a legal department, a company or a city.

Thomas Richards: No, and I didn’t either. I thought I would be a lawyer my whole life. It agreed with me. Wanting to do something else really occurred to me while I was at the firm and after I got involved in the management of it.

One of the reasons I left the law firm is that I found myself getting a little stale. When I was the managing partner, I remember a couple times saying to myself, “You know, you’re not listening to these people anymore. Maybe it’s time for you to do something different.”

I went to [Rochester Gas and Electric Corporation] when I was 50. … I used to kid about it—I had this midlife crisis, but I only had to move two blocks. I intended when I went there, if I was given the opportunity, to become involved in the management of the company. That was my intention. So that worked out.

When [then-Mayor Robert] Duffy recruited me to come back and be the corporation counsel for the city, I hadn’t practiced law in 10 years, probably. One of the happy parts of that is that I realized I still liked it. That’s why I wound up staying longer than I thought I would.

TAL: Once you became mayor, you were back in a CEO role, but also in politics.

TR: I came into it without any political background. I wasn’t even registered in a party. You know, there are some disadvantages to being my age and [in] my circumstances, but I think you bring to it a certain experience and also a certain detachment that I think is useful.

TAL: What do you mean by “detachment”?

TR: I don’t mean to say that I’m not ambitious or I didn’t want to do it. I did. But one of the things that happens to politicians—and I see it in them now that I’m around them all the time—is that you just have to have this job. You just can’t imagine yourself doing any- thing else. And when that happens, you get compromised.

TAL: So you had some freedom.

TR: I did. Yeah, I did.

TAL: How big a factor was your son’s illness while you were running for reelection?

It was a significant factor. He had been sick for a long time. But I thought he would live for some months [more], and it didn’t happen. I think if that crisis had occurred earlier, I probably would not have run at all.

You have to believe what you say, right? Remember [how] I said one of the advantages I think I have is that I don’t have to do this? You know, I don’t think I’m defined by [the job of mayor].

He has a young family. And since he was sick for so long, they were very dependent on us. And that was part of what made it even more difficult. There was a tragedy in that family, that’s for sure.

But we are in a position to help. And that’s good.

TAL: You were criticized for not sending strong enough signals about whether you were still running after the primary.

TR: Looking back on that, I don’t know that I ever would have been able to satisfy people. I just decided, somewhere along the line, I’m done explaining myself. And it’ll be what it’ll be. Time heals those kinds of things. At least I’m comfortable with where I am and what I need to do.

TAL: Being a full-time grandfather?

TR: I’m going to spend a lot of time with this family for a while, to make sure that everything is OK there. But eventually I’ll do something else. … When our kids were born, my wife stopped working for quite a while. That meant that I could do what I did professionally. Now I’m at the point where I actually can and should assume more responsibility in that regard. There’s an irony to that, isn’t there? It just flips it on its head. But some things are meant to be.

TAL: Ever get wistful about working with clients again? Billing by the hour?

TR: Not billing by the hour. I’m not wistful about that. But one of the things that’s given me all these chances to do different things has been the fact that I was a lawyer. Some people do the same thing their whole lives and love it. But I don’t think being a lawyer needs to confine you.