NewRetirement Podcast: Work and Jobs Over 50 — Steve Chen Interviews Kerry Hannon & Philippe Violette

Hosted by Steve Chen, founder of NewRetirement, the NewRetirement Podcast offers interviews about the wise use of both money and time in retirement.

Explore ideas and great insight so that you can achieve a secure and meaningful future.Episode 2 is an interview covering two perspectives about work, working less and jobs over 50:

  • Kerry Hannon is the AARP jobs expert and author of “Great Jobs for Everyone 50+”
  • Philippe Violette is an entrepreneur and ‘productivity hacker’ who has experience cutting his costs and increasing his free time by moving to the Dominican Republic and Buenos Aires.

retirement income planning

Listen and explore how to transform your perspective about what work really means.

Should you work for income? Happiness? Or both? How can shifting your ideas about what you get out of work change what you do?

Can you find a different job that makes you happier? And, on the other hand, can you change how you live your life so that you actually need less money and can work less?


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Full Transcript of Steve Chen’s Interview with Kerry Hannon & Philippe Violette

Steve: So welcome to the second podcast for NewRetirement. Today, we’re going to be talking about work and jobs over 50 and lifestyle design, which aligns with the two main themes of our podcast: making the most of your money and time.

So today we’ve got two guests for our second podcast, including one in studio. We’ve got Kerry Hannon, a recognized expert on work and jobs over 50.

She’s an author, columnist, speaker, and has testified in front of the Senate. I believe you also work for the AARP. Right, Kerry?

Kerry: Yes, I’m a columnist and I’m their jobs expert.

Steve: We also have Philippe Violette, a small business owner who has been on his own for a while with a couple of twists.

He ran his own business virtually from the Dominican Republic and Buenos Aires for a few years. He’s also a personal productivity hacker and a student of Tim Ferris.

Philippe: Thanks for inviting me.

Work Perspective and Lifestyle


Steve: I just want to jump right in here with a couple quick questions. Kerry, can you share your story of what your job is today and kind of how you got to this point of being an expert around this topic?

Kerry: Well sure. Well first of all, Steve, thank you so much for inviting me to be on the podcast today. It is such an important topic working and the whole idea of working at older ages than any generation before us.

My story is this: I started my career as a business writer and I worked for Forbes Magazine, and I would travel around profiling companies and so forth.

And then I worked for Money Magazine and US News and World Report, and was a columnist for USA Today, doing a column about retirement and taxes.

And then I decided, you know, all along I was writing books. I had done a book on a retirement guide for women, a book called Suddenly Single for Divorcees and Widows, and a book on estate planning.

I had started sort of putting together this idea. I love to write books. And to date I’ve actually written a dozen books now. That was really fun.

And so what happened is I got to the point in my life where I was miserable in my job.

One day I said – as we do at certain stages in our life – I asked my father, I said, He asked me how I was.

We were walking along a beach one day and I said I’m terrible. And, he said, “Well, you know, what’s wrong?” And I said I just really hate my job. And he said, “Quit.”

So I went back a couple days later and I quit.

And just at that time, I had an opportunity to write a book with a girlfriend of mine who’s a fabulous photographer, a coffee table book on Navajo weaving.

And I went out to the reservation and spent some time profiling weavers. It was really fascinating because two of them didn’t even speak English.

One woman I profiled was in her 80s and lived about 45 minutes down a dirt road from a paved road.

And she lived in this hogan, which was very small, and she raised eight children with no running water and no electricity.

And I asked her questions through a translator, and she said, “You ask questions nobody thinks about.” And I was like what?

And I had all my east coast sensibilities about me and I looked around where Mary lived, and I’m telling you, Steve, it was tremendously beautiful.

And I learned how … It just hit me, the importance of loving what you do and how you work.

Mary wove these monumental rugs that were so beautiful, and it struck me that that is what we should be doing with our lives.

And I started on this course of, of sort of, introspection about what work, how it intersects with our lives and meaning.

It’s been a weaving road like most of our careers are. But the core of it is I just love, telling people stories.

I’m fascinated about work and this whole aspect of, since I’m a baby boomer, taking a look at what the longevity means to me and to those around me.

How we can keep work a part of our lives.

Work After Retirement

Steve: You know, I appreciate hearing that, that backstory, and I’ve been talking to more of our users and also potential advisors and investors, for our business about kind of this topic.

I mean we started with kind of the financial side of this and, you know, we help people think about, you know, how much do they need to save, and, and how should they kind of deploy their money and, and how should they claim social security and stuff like that.

But, you know, where I really see people lighting up is, you know when they’re thinking about kind of what’s next and how are they gonna use their time.

And obviously work is a huge part of this. And I think kind of there’s two, different themes that I see.

So one is there’s people that have plenty of money and they’re really thinking about, okay you know, if I have plenty of money, how would I kind of ideally spend my time?

What’s my dream job and so forth? And, or service work or whatnot.

And there’s also people that are a little bit driven more by fear and they’re kind of thinking, you know, you know, I need to make some amount of income.

What’s a more secure job? You know, what’s a job that … But try to balance that with like things that they, they would like doing.

You know, so I think, I’d love to get your opinion.

So now that we have 75 million baby boomers that are kind of roughly between ages 53 and 71, you know, can you give us your perspective on kind of what you’re seeing out there in terms of trends and what kinds of jobs they’re finding?

And are people satisfied and things like that?

Kerry: Yeah, Steve. You know there’s two things just as you mentioned that’s so, so absolutely true. There’s really two sort of sides to this.

When I speak to audiences around the country, I have to tell you of workers over 50 who are looking for jobs, and I, I come there, speaking to kind of give them hope and say hey, you know, this is what you need to do.

Ageism is alive and well in the workplace. But I’m telling you, when I look out there, I see the palpable fear in their eyes that they are going to outlive their money, and they very well might.

I mean there’s a real crisis with people, you know, the aging population that really have not saved adequately for retirement.

And so what’s become, you know … And then I see this, the other section and some of the folks you just mentioned who, yes, they have planned for retirement.

They have saved. But, but you know, they want to continue working in retirement, kind of as a safety net so that it helps them push back dipping into retirement accounts.

They can perhaps continue to contribute to retirement accounts.

They can push back social security so that in essence you get a little bump each year, you know, 8% more annually until you reach your full, you know, age 70 when you have to start taking it.

But, but it also, it’s a safety net financially and it also is a way to stay engaged, to say …

You know, studies have shown it keeps us mentally engaged. Use it or lose it.

Physically, it keeps you, um, more, you know, you’re healthier, you’re moving, you’re relevant, you have a reason to get up in the morning.

So there’s really great reasons.

So the primary thing that I’m seeing out there in the big picture is that what’s different today is that when people plan for their retirement they often, you know, considered, you know, they had their savings, you know, their personal savings.

They had their retirement savings and they had social security.

But now there’s a fourth pillar, and that pillar is work has become a pillar of a retirement plan.

And people I really see are starting to think, you know, and I advise them to at 60 think about what you might want to do at 65, and it might not be …

You know, it might be contract work or part-time work, seasonal work. Just something to stay engaged and involved.

But it takes planning. You don’t just retire and shift to something new.

It really is a process, and I try to encourage people to start thinking of it because really with the longevity that, Steve you mentioned at the beginning, um, you know a 60-year-old person could easily have 15 more years of really tremendous kind of work experience and giving back.

It sort of shifts the equation of what’s possible and what you might want to do, and whether you might even want to go back to school again to add more skills, so you head off in a new direction.

Searching for Jobs Over 50

Steve: Yeah. Yeah, I, I totally agree with what you’re saying. Yeah, I wanted to share a, a quick story. We are, we were gonna have another guest here but he actually came down with the flu. A friend of mine, Mike Himmelfarb.

But he recently decided to leave his SVP job at Nielsen and start his own consulting firm because he wanted, you know, to balance kind of work and life better.

He was traveling all the time and he decided he wanted to have more time with his family, kind of more schedule control.

One thing he shared with me was that, he’s seeing kind of a, you know, an emerging kind of gig economy out there for talented senior folks.

You know, larger companies, they don’t necessarily want to sign up to pay someone 55 or 60 on an ongoing, long-term basis of big, fat salary.

But they, they do want the talent and so they’re definitely up for kind of a more, you know, contract, gig-based approach.

And, and I think, you know, there’s gonna be a need in the economy. I mean, you know, there’s definitely stories that if the boomers start retiring and leaving the workforce at a faster clip, it’s gonna create a talent shortage.

I mean I see this in certain, job sectors out there right now. I mean, if you go out there and kind of look at a lot of people that might be kind of doing more trade jobs, you know, electricians, stuff like that.

Very often you see the talented guys, the plumbers, they’re older, and there aren’t that many necessarily kind of younger guys that are being kind of apprenticed and trained up.

So we may have a problem where we lose some of these skills. Machinists and stuff like that.

You know, one other quick thought for you is that, you know, on the planning side I think one thing that can be liberating is, I agree that, you know, work is a, a huge part of any plan, and, and should be factored in.

I don’t think people should expect, or most people should expect, “Hey, I’m just gonna be done at 65. I’m not gonna work and I’ll be fine.”

You know, I think the risks are, you know, really high with, you know, that, that you could potentially run out of money. So I think you’ll see people working longer.

But I think if people take the perspective of, “Hey, you know what? Maybe I was making $70,000 a year. If I only need to make 30, you know, and I can do that many different ways, you know, and I’ll, and I’ll improve my security a lot.”

I think a lot of people find that pretty liberating and they’re like, “Oh, okay wait. You know, I was making 70 but I only need to make 30 now. Here’s all these different things that I could do. You know, I could teach part-time, I could, you know, I could, I could work here or there.”

And so kind of changes their perspective.

Kerry: Steve, I absolutely loved what you said about the skilled trade jobs because if anybody wants to shift into doing that, and actually in seeing this as, you know, people are retiring or thinking about retiring.

You know, they’ve always loved to do handy work around the house, or they’ve always enjoyed doing that sort of job.

There really are opportunities if you can get skilled up a little bit in it to look for work in plumbing and, you know, all kinds of different things along those lines, because electrician even, which is a much more difficult thing.

But I know a guy here in Washington, DC where I’m based too, you know when he retired from his job at the FBI, he, he loved to tinker.

I mean that was the thing he would take things apart and, you know, put them back together as a kid and that sort of thing.

And today, he works repairing wheelchairs and gurneys at a local hospital. And he, and it’s part-time, and he loves it. You know? (laughs) It’s just really, really fun.

So I mean you need to open your mind to think about what are some of the kind of things that, you know, if my ego’s not in the way that I might really enjoy doing, and there is opportunity.

We can talk a little bit about one segment of jobs I call, you know, jobs to ride the age wave, which are ones that we can that people in their 50s and 60s might do to cater to the aging population in their 70s and their 80s.

Work and Life Balance

Steve: Since you mentioned kind of, kind of the lifestyle thing earlier, and we talked a little bit about kind of work and life balance, I wanted to bring Philippe in here.

So you know, he’s done something interesting. So he kind of went off and, you know, he worked for a larger company and then decided to go out on his own, create his own business.

And then he took that business and he operated it out of, two different countries. So the Dominican Republic and also out of Buenos Aires in Argentina.

So I just wanted to kind of have him come in and give us a little background about why he made that decision and, and kind of how that worked out.

Philippe: Well, Steve, thanks for inviting me.

Well I think what your listeners will be most interested in is the story of, you know, what motivated me to do it, and, a lot of it comes from the fear that Kerry was talking about earlier.

In 2009, I was in Newport Beach and I was running a financing company with a business partner, and I had a very high cost of living. I was working long hours and my partner and I decided to split.

He bought me out and I started a company doing a similar thing on a smaller scale.

But as you can imagine, it was a very uncertain time. The housing market was collapsing, there was a recession.

I had a young family. I had three kids four and under, and so that fear was a big motivating factor and decided to, the fancy term would be leverage currency differences. But I think the actual words were to sit on a beach and nanny up.

So I ran my company from the Dominican Republic and from Buenos Aires.

What I learned is you can live incredibly cheaply and lavishly when you get outside the US, if you’re able to do that.

And I, I think with technology now it’s, it’s very easy to do it. It was kind of terrifying back in ’09, but now I’ll, I’ll travel and I don’t even have to think twice about it.

So I was able to cut my hours in half in addition to it. And so besides living on a beach, I think there were a lot of unexpected perks that I found.

And one that might be of interest to the listeners is that there’s something called foreign earned income exclusion.

Essentially what that means that if you were living outside of the US for 300 days or more a year for a fair amount of your income, you don’t need to pay any taxes on it.

And if you have a wife or a spouse or someone else you can make an officer of your company, you can double that.

Steve: Wow. Good tax tip. (laughing)

Philippe: And you can put that money in savings and retirement, which is something that, you know, we did.

Steve: I mean we’re definitely seeing people really explore retiring overseas.

It’s kind of interesting to think about like combining that with making some incremental income. You know, either alongside or as a way to bridge to social security when, when they’re older.

Were there any big drawbacks for, for going overseas? Or was it, was it good?

Philippe: There really weren’t that many drawbacks. You know, the, the fact that it’s more difficult to visit family.

We were able to find some pretty great schools, even in small towns in, you know, the north coast of the Dominican Republic.

So a lot of things that we were terrified about, that I was really worried about running a business, didn’t end up coming to fruition at all.

Steve: You know, as you’ve done this, have you kind of made any decisions to kind of keep kind of work and, life kind of in balance?

You know, as you, as you run your business? Or do you feel like you’re pushing harder on one or the other?

Philippe: No, for sure. That’s something I struggle with all the time though is keeping that balance and that the work-life balance and the quality of life.

It’s easier to do, I think, when you’re sitting on the beach. But when you’re back here, now I’m back in the States full-time, I’m in California. I’m in Northern California with you.

Steve: Yep.

Philippe: And, you know, it’s expensive and you’re trying to keep up with the Joneses. Trying to keep the definition of success and keep that idea of what that is.

Is it that flexibility and is it that lifestyle design, or is it making the money and keep that in balance?

Steve: Right.

Philippe: So you’ve got to make the money but I’ve come to value a lot more the flexibility that goes with it.

Keeping Your Skills Sharp

Steve: Any final ideas that you want to, or thoughts you want to throw in here before we wrap it up?

Philippe: I’ve got a funny little personal story I’ll throw in, which Steve may or may not know, but it kind of gets into what Kerry was saying about getting out there and keeping your, your skills sharp.

I was in my 20s and I came actually out of the corporate world and got into the dot-com world.

Steve actually hired me and I took a big pay cut and, it seemed like a big step down into telemarketing.

And I thought I’d come in very easily and make a big splash, and it was a lot harder than I thought at first.

But a friend of mine suggested I just go to the library and check out a bunch of sales books. And I did. And I read three, and two of them were great.

And it made a huge difference, and pretty soon it made an enormous impact on my sales and actually made an impact on the company.

So, something as simple as Kerry said about going to Toastmasters or, you know, something you’re a little worried about, there’s a lot of resources to try something new.

Steve: Right. That’s a great idea. A library. Awesome.

Philippe: Simple.

Steve: Yeah. You know, we’ll wrap it up here but you know I want to say thanks to Kerry and to Philippe for being a guest here on the second podcast.

Thanks to Davorin for being our sound engineer, and anyone listening, thanks for listening. Hopefully, you found this useful.

You know, our goal at New Retirement is to help anyone plan and manage their retirement so that they can make the most of their money and time.

We offer a powerful retirement planning tool and educational content that you can access at

So, thanks again and hopefully we’ll see you on the next podcast.

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