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This is Dan Morrell, host of Skydeck.

At the HBS reunions in 2019, the Skydeck team set up shop on Spangler Lawn and asked alumni to share their secrets to a successful retirement.

John Teeling, DBA 1979, who has started a number of Irish whiskey distilleries, hadn’t intended to sit and offer his advice, but his companion had other ideas.

Teeling: The reason you have me here is because my wife was listening to the request to come on and she says I’m not allowed to retire until I’m 94. You shouldn’t ask me about retirement, because I’ve done absolutely no planning for it other than financial. And I’d hope to be able to work as long as I’m enjoying it, which I think could be a few years yet.

Morrell: In this episode of Skydeck, you’ll hear from some happy retirees about what makes for a successful exit from the working world—and a few more like Teeling, who chafe at the very notion. And while this episode of Skydeck was notably recorded in pre-pandemic times, we think the advice offered here remains relevant.

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My name is Wally Eamer or Wallace Eamer to be more formal. Section B, year of 1979. I would urge people not to think of retirement as a term at all. Now you are at a stage of life where you have freedom to choose how you will engage your time and energy, your purpose. You have the financial independence to choose the purpose that is useful to the world, in your view, and that is important to you personally. For heaven's sakes, take advantage of that freedom and use it well. So you don't retire from something. You go to something of deep personal and social significance and do your best, do your best.

Jeff Singer, MBA 1984. The best advice for successful retirement is knowing when you're ready, you have to be in an equilibrium, you have to be able to say, OK, I've accomplished in my career whatever I want to, I need to. My advice to myself was I wanted to make sure that I wrote the last chapter—that I would move to retirement on my own terms. It's a big adjustment. You have to get used to going from being in the center of everything going on to having an empty email box. No one's looking for you in the morning anymore. And that's a big adjustment. But the flip side is you have total freedom to decide how you want to use your time and and just focus on that.

Jennifer Wilson-Buttigieg, OPM Class 33. Retirement—nowhere near it. And if you really love what you do and you have a passion with a capital p, there's no need to retire. My mom, our founder, our chairman, our CEO, never had a college education, built this business from nothing. My sister and I as co-presidents, it's our honor to bring it through the next generation. She wants to die at her desk. And looking at our clients today, looking at people today, they want to explore the world. And I'm in the business of hospitality and travel. And the one nonrenewable asset is time. So why retire if you love what you're doing and you can actually make a difference and an impact? I look forward to doing this for at least another 30 years.

I'm Chuck Berman and I'm the Class of 1979. I wouldn't retire. My mind would waste away, I find that I'm probably now in the fourth or fifth company that I've started. We're six years into it and we're looking at partnering with someone to create another new company. I think about the new company, it'll take me out another 10 years till I'm 75.

I think leadership has an awful lot to do with passing on fears, and experience, and mistakes and other things that will help other people deal with their own fears and anxieties and hopefully avoid some of the mistakes that I've made and will continue to make.

It doesn't feel like work. I get up every day and I get beat up every day, too, because things go wrong all the time, and they’re always worse than you think they are and take longer to fix and cost more. But the goal of what I do is like building community. I've been a real estate developer since the early 1980s and it's always about what can we do more? And in this next phase, we're gonna be trying to focus much more on rebuilding harder-to-serve urban neighborhoods in a broader way than just housing.

And I get excited thinking about it. And I wake up at night fearful that we won't succeed because it's so important to get this to happen.

Richard Linowes, DBA 1984. Newly retired. I'm stepping into another position. I've been a faculty member for 33 years after a career on Wall Street. And now I'm taking over a brand new university that’s just been established. Find your core mission. Find the thing that you're passionate about and throw yourself into it and learn how to build a business around it. Learn how to actualize it, whatever your chosen path is.

And I guess I realized that when I saw some people doing unethical things on Wall Street, I decided I wanted to fix it. And I became a professor and actually went through a human potential course at the same time, which got people to really focus on that. And I realized there's so much more we can do beyond the wonderful education we get here. There's so much more into tapping into who you are, your heart.

Rebecca Katz, AMP 193. I work for an investment firm, we talk to people about retirement all the time. I think what makes the path through retirement easier is if you've spent your life living below your means. And so many of us don't do that. And we buy big mortgages and buy more than we need, and really the easiest thing to do is pay yourself first and live below your means and you'll get there more quickly. I also think it's really important for a lot of us, especially Harvard graduates, work is probably all-encompassing and the prospect of stopping work and pivoting into something different is a little bit frightening. And so I think it's really important to start in your earlier life. I'm in my mid-40s and building relationships and other community activities and things that will fill that hole.

So I'm Jonson Cox, I was in an AMP program, 157, in 1999. I never expected to cease being a full-time chief exec when I was about 53 or 54. But I did. And then I sort of found my way into a plural career, chairing things that weren't full-time. And I chaired a restructuring of Britain's coal industry, which is one of the oldest industries in Britain. So doing that was fantastic. And then talking of doing unexpected things that I never imagined in my life I would do—I became chair of what we call an independent regulator. Our utilities industries is privatized, water in particular. And I chair the organization that regulates water monopolies. They’re big companies. Many of them privately owned now by pension funds, infrastructure funds. And our job is to hold them to account. And that's a lot more than things about quality. It's about how do you get a monopoly to behave in a manner that treats its customers with respect, that drives efficiency and innovation as it would if it was competing for its business and for its life.

If you'd asked me would I want to do that the answer would have been no. I ran a mile. I refused to apply. I said, no, I don't want to do this. It's wonderful. You get to lead really bright young people, way brighter than me, who've got many degrees and yet perhaps can benefit from a bit of experience from people who run businesses. And I just think it's wonderful.

And there's this wonderful thing that when you're plural, as we call it, with a number of things—no one has a sole call on your time. When I was a chief exec, the business had the call on my time 24 hours a day. No one has that all on me anymore. And that’s wonderful.

Skydeck is produced by the External Relations department at Harvard Business School and edited by Craig McDonald. It is available at iTunes and wherever you get your favorite podcasts. For more information or to find archived episodes, visit alumni.hbs.edu/skydeck.

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