Nancy Collamer Nancy Collamer
Podcast 23

023: How To Plan Your Second-Act Career with Nancy Collamer

Nancy Collamer is a coach, consultant, speaker, and author. She writes about the changing nature of work and retirement for PBS’, contributes to, and is the author of Second-Act Careers: 50+ Ways to Profit from Your Passions During Semi-Retirement.

There are now more opportunities than ever for people who are leaving full-time jobs but are not wanting to fully exit the workforce. Nancy, who herself is in her second-act career after working full-time in human resources, has conducted hundreds of interviews with not-quite-retirees, and compiled a hugely valuable career guide for anyone looking to take on fulfilling, profitable, and flexible work during what she calls the “encore stage” of their careers.

Today, Nancy joins the podcast to talk about the changing trends in retirement, why we’re now seeing more entrepreneurs than ever over the age of 65, the common threads among the working retirees she’s met, and the tools she uses to help them find fulfillment at any age.

Get a Free Autographed Copy of Nancy’s Book!
Would you like a free autographed copy of Nancy’s book Second-Act Careers: 50+ Ways to Profit from Your Passions During Semi-Retirement sent directly to your doorstep? It’s simple… All you need to do is click here to subscribe and review the podcast on iTunes. Then just take a screenshot of your review and send it to [email protected].

In this podcast interview, you’ll learn:
Why more and more people are finding ways to work on a flexible basis in their retirement years after their full-time jobs come to an end.
How Nancy’s second act career took shape as she created multiple streams of expert income.
Why consulting comes up so often among people who do flexible work – and how to find your first project and build your portfolio.
The reason retirees need reason, purpose, routine, and community – and how work or volunteering helps to fulfill this.
The key questions Nancy asks to help retirees find their motivation and purpose.
Why we’re so much better at talking about what we don’t want rather than what we do want – and how this helps us find out what we truly enjoy.
The reasons post-retirement work (or volunteer work) can be unfulfilling – and why it’s okay if your role, or what you’re excited about, changes over time.

Inspiring Quotes
“Work gives us a daily routine and people sometimes underestimate the value of that. It provides us the community, it gives us purpose, and it also feeds our sense of status and self-love.” – Nancy Collamer

“Retirement is a point in time where you’re finally freed up to do what you want to do. You’re freed up to share your gifts with the world in a way that really speaks to you. And quite frankly, it’s an opportunity to just have fun.” – Nancy Collamer

Interview Resources
My Lifestyle Career
Next Avenue
Second-Act Careers: 50+ Ways to Profit from Your Passions During Semi-Retirement
Million Dollar Consulting

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Read Full Transcript


Casey: Welcome to Retire With Purpose Podcast. This your host Casey Weade and today we got a special guest. Nancy Collamer is joining us. Welcome to the podcast, Nancy.

Nancy: Thanks so much. Glad to be here.

Casey: I’m really excited to have a conversation with you about your latest book in focus titled: Second-Act Careers: 50+ Ways to Profit from Your Passions During Semi-Retirement which I really enjoyed reading and we’ve got a lot of families that we work with that are a listening right now that are thinking about this second stage of their life and what that might be like. And I’ve got more and more families I work with that are starting new careers and starting new businesses starting in consulting or getting coaching or writing the book that they always wanted to write and sometimes they get a little confused on where to start. I think this book was a great resource on getting started. But as we read the title, I think there's going to be some that listen and go, "Semi-retirement? That sounds kind of like a strange topic. Isn’t that a bit of an oxymoron?” What is semi-retirement?

Nancy: Yeah. Well, and the first sentence of the book I’d say that working during retirement is by definition an oxymoron. But the truth of the matter is, is that increasingly, we are going to see more and more people who are leaving their full-time careers and then they go on to do something else on a flexible basis during retirement.

Casey: Well, you had said one of the statistics in your quote I think you said the share of new 55 to 64-year-old entrepreneurs has increased from 14% in 1996 to over 20% in 2011.

Nancy: Yeah. And what survey show, Casey, is that nearly three-quarters of people say that they plan on working in some way during the so-called retirement years and there are several reasons for this. First, people are living longer, they’re living longer, healthier lives. So, what used to be a 15 or maybe 20-year time period has suddenly expanded to 30 years, in some cases even a 40-year retirement. Actually, just earlier today I was reading a cover story of Money Magazine and it’s about 100-year-old retirees. And so, a lot of people are now faced with what I call the 40/30 dilemma. What do I mean by that? Well, for the first 40 years or so, we put all of this time and energy and attention into our careers and then suddenly, you have 30 years where people go, “Ah, that’s when I'm going to relax.” Well, that simply doesn’t work for people. It's not financially possible for most folks these days but also that’s a heck of a lot of hours to fill and people are looking for ways to fill those hours in a way that is going to be meaningful and engaging and energizing for them.

And so, you add all that up, it’s not surprising that we’re seeing more and more people who say I’d love to continue to work. I don't want to necessarily work on a full-time basis. Been there, done that, but I'd like to figure out something that I can do on a flexible basis that really is going to be meaningful and hopefully will generate some type of income as well.

Casey: Well, there's so many different options and avenues that you can take and I know you've got different outlets where you have interviewed maybe hundreds. I don’t know how many different retirees or pre-retirees would you say you’ve interviewed throughout your writing and your career here?

Nancy: I’d joke that that's a hazard of my trade is I meet somebody on the supermarket line and we get to chatting, “So, tell me how did you start doing that?” So, honestly, it has been hundreds both formally and informally. And, you know, I think I am so fortunate that I’ve had that opportunity to do that because I look at this time period as a period where there's going to be tremendous opportunity for people to really do something that they didn't have the chance to do when they were working full time and the primary concern was paying the mortgage and paying for the college bills. People oftentimes are freed up during this time period to really do something that they would like to do and they just didn't have a chance to do before.

Casey: Well, with all the different options and all the different individuals, so hundreds of individuals that you've interviewed and met over the years that are retired, how did you narrow it down to 50 different individuals or 50 different ways? Because there's hundreds. How did you select these ways to profit during retirement?

Nancy: Yeah. So, at the beginning of the book, I talked about some of the criteria that I used in making my selections and it was a couple of things. One was I want to focus on things that weren’t going to require a tremendous investment of time or money to start over again in a new field. So, for example, I don't include any brick-and-mortar businesses because typically that requires a significant financial investment. I also really focused on things that people could feasibly do on a flexible basis and when I say flexible, that really runs the gamut from working on a part-time basis to doing seasonal work, project work. These days we’re hearing a lot more about the gig economy and we can talk about that later, but there's a lot of opportunities there.

So, I focused on things that were doable on a flexible basis and I also steered away from anything that was going to require a significant level of physical fitness. And so, I got to tell you, I know plenty of 60-year-olds who are running marathons and doing triathlons and are in great shape, but that said, most people don't want to do something that is going to require them to be on their feet all day or lugging heavy boxes all day. So, I steered away from those types of opportunity.

Casey: Well, Nancy, I understand that you are living at your second act career, and I wonder, would you liken it to one of these 50 different ways that you outlined during your book? Or really, what did your process look like and what’s your second act career? Could other individuals do what Nancy is doing right now?

Nancy: Yeah and I think lots of people are in different ways. So, actually, the first chapter of the book when I actually get into the 50 possibilities is about multiple streams of expert income and that’s exactly what I'm doing. I do coaching, speaking, writing, I have a digital presence. I sell digital products and my revenue is being generated from a variety of those sources and increasingly, I’m seeing more and more people, particularly people who are in professional level jobs who are finding ways to create what I call again multiple streams of expert income. Certainly, when people talk about what people are going to do in retirement, I mean, what's the most popular response? People will say, “Oh, I’m going to be a consultant.” That is certainly one of the ways that people do it and it’s a very, very popular option. Just last week I was in a meeting with a group of retired United Way executives and several of them were consulting to nonprofits on how to run their organizations more effectively.

And so, you see people coming out of professional roles who consult as independent. Sometimes they get paid. I was talking with the woman the other day who was actually the CEO of a big financial firm. She now has been asked to serve on two different for-profit boards and so that's a way of being a consultant or an advisor but she's doing it in the role as a board of director. So, I think this whole arena of finding ways to share your expertise again on a flexible basis is something that's really attractive to a lot of people.

Casey: Well, it sounds like a lot of work, and I wonder what you didn't just get to where you're at today overnight. Yeah. I think sometimes we hear, "Well, we’re blogging, we’re writing, we’re writing for Forbes, we’re writing books or on podcasts,” and doing all these great things and sometimes that sounds a bit overwhelming to some but I imagine your journey didn't look like an instant success. It was maybe kind of something you eased into. What did that transition look like? Was it blood, sweat, and tears?

Nancy: Well, you raised a great point and I think that it’s a really important point to highlight to folks that first of all, it doesn't happen overnight but when I started out, it’s sort of an interesting story. I was in corporate HR and then from there after I had my first daughter who is now 30 and will be getting married in the spring, I really wanted to be able to spend more time at home and this was the dark ages of flexibility. So, when I talk with my employer about the possibility of going part-time, I mean, it was just like, “No way.” So, I decided to stay home. I stayed home for about a year and then I thought, "Well, I really need to figure out what I want to do next.” And so, I thought about the parts and pieces of my job that I had enjoyed while I was working in corporate HR and realized that even though I had not been trained in career coaching that that was the piece that I really enjoyed the most. So, went back to school, got a Masters in career development, and so that was income stream that I really concentrated on for the first 15 years or so of my practice was doing coaching with people.

But the more I coached, the more I realized that I was starting to build up a body of knowledge. Actually, at the time I concentrated on coaching women who wanted to work on a flexible basis, specifically moms. And so, I really began to get a lot of information and insights into how can you work on a flexible basis and that was at the point that the Internet was starting to take hold. So, I started writing online, and I started writing for a site that was called Moms Online. It doesn't even exist anymore but at the time it was AOL’s main parenting site and the truth of the matter is I wrote for them for two years for no pay and it was a heck of a lot of work but I always sensed that if I could just develop that presence online that something would happen. Well, in my case, what happened was eventually Moms Online was acquired by a group called Oxygen Media. One of the partners might be quite familiar to our listeners. Her name is Oprah Winfrey and so that suddenly opened up the door for me to do more writing for some of the Oxygen sites and of course for that, I got paid. And then from there because I have the presence that led to the book and then the book led to writing for Next Avenue and Forbes and so it's been a 20-plus-year journey to get there. So, it doesn't happen overnight, but it happens piece-by-piece and step-by-step as most people's careers do.

Casey: So, do you find 20 years into this that it's kind of changing for you? Did it go from a lot of work until to are you working less? Are you actually going to truly have full retirement at some stage or do you see the semi-retirement thing continuing for forever?

Nancy: I love what I do and so I see myself doing a lot of what I'm doing right now for the next 10, 15, 20 years. It's all very possible for me to do this because a lot of what I do is I work from home so I could very easily be 75 or even 80 and doing what I'm doing. So, I'm not quite sure how it will all roll out and that’s another thing I’ve learned along this journey is that when you put yourself out there and you talk with people, opportunities happen and you call it serendipity, call it fate, but it's really when people start putting themselves out there, sharing their gifts with the world, you just never know where it might lead particularly in today's economy.

Casey: Well, and one of the things I’d say what you did is you didn’t just throw away your previous career and started a whole new industry or starting a whole new career path, whatever that might be. You took items from your previous experience from your career and pull those things out and created a business out of the parts and aspects of your previous career that you really enjoyed but, in your book, you say, "Don't dismiss, don't completely dismiss your previous profession or industry,” but you'd also mentioned that that's exactly what you wanted to do at some point.

Nancy: Oh, yeah. Absolutely. I think I called that Don’t Throw Out the Baby with The Bathwater and the fact of the matter is I left my corporate job and as I said, I was sort of disgusted with the whole corporate thing at that point and annoyed that they weren't going to let me work part-time. And so, initially, I was like, “Ah, I’m done with this.” But when I calmed down and took a step back and really thought about, “Okay. Maybe I didn't enjoy the corporate politics and I didn't enjoy some of the demands of having to go into an office every day.” But what were the parts that I enjoyed? And I realized that there were a lot of things that I really actually did like about the job and that's one of the things I really encouraged my clients to do. Recently, I met with a gentleman who had worked on Wall Street for pretty much his whole career and when he came to see me, one of the things he just kept saying over and over again is, “I am so done with the sales quotas,” and he just kept bringing that up. And finally, I said to him, "You know, I hear you loud and clear but let's talk about some of the things that you really enjoyed about what you do.”

And again, in his case, once he had time to just decompress and take a breath, what he realized was he actually really enjoyed a lot about the financial world. In his spare time, he read financial magazines and always made it a point to read the Wall Street Journal every day not just because it was good for his career but because he found it interesting and he has got on, he's now teaching economics at a local college and really enjoying that and he's also sitting on the board of two different nonprofits and helping them with their finances. So, he took the pieces that were most appealing and meaningful to him and he is now building on those to really have a very satisfying second act.

Casey: Sure. And you had mentioned consulting as typically one of the things we see over and over again. That seems like we work with a lot of engineers more than anybody else. It seems like they just love getting in the consulting field, but you'd also mentioned that you started as a coach. What's the difference? What do you think the differences between a coach and a consultant? Are those the same thing or how would one define whether they should go down one path or the other?

Nancy: Yeah. Well, I think that's probably a bigger issue that we can address here but just very briefly, a consultant oftentimes is pulled in because people really want to get your expert advice and opinions on a particular problem that they’re dealing with. So, going back to the example of the group at United Way that I met with last week, several of them are working with other nonprofits who need assistance with how do we market ourselves better or what do we need to do in terms of our volunteer recruitment? So, they’re looking for very concrete strategies and information. A coach does get involved with some of that but a coach really starts with the basic premise that the client already has the answers and that it’s the coach’s job by asking the right questions to get the client to look within themselves so that they can pull that information out. There’s some crossover, but it is a different approach.

Casey: What would you recommend for someone as a good first step if they want to get into the consulting world?

Nancy: Yeah. So, I think if you want to get into the consulting world, a great place to start is by talking with people who you know from your professional world and see if there's a project that somebody might be interested in having you do for them because that's a great way of just testing it out, seeing what it's like to be on the other side of the desk and also to begin to build up your portfolio and your reputation. So, absolutely start with your network of contacts. I think another great way to find consulting assignments and entrepreneuring jobs, in general, is to think about attending a conference that is associated with your industry or your line of work. I have been amazed over the years at how successful some of my clients have been when they've gone to tradeshows or industry association meetings. The number of contacts that they are able to generate in just one day or two days is really pretty remarkable and it’s also a great way to meet people in the industry to hear about what some of the current issues are that people are working on and to meet other vendors who you might be able to pair up with. So, I would certainly start there.

And then, of course, I mean if you take a look at Amazon there are multiple books out there, hundreds of them about getting started as a consultant and so that's a great way to learn about some of the nuts and bolts of getting going. And then finally, I would also recommend both the Small Business Administration and SCORE which SCORE stands for the Service Corps of Retired Executives. Both of those are great free resources and the Small Business Administration, if you just go to, you can see they have all sorts of webinars and training programs and classes on lots of different topics and that can be a great way too to get started.

Casey: That you had mentioned some books that there's a lot of them out there. How do you sift through and find the right one? Do you have any that come to the top of your mind? Is there a really great book on consulting?

Nancy: Yeah. The author he's written several of them on consulting. I like Alan Weiss's books and he has several. He has Million Dollar Consulting and several others and so I would recommend his books. It’s a good starting point.

Casey: Okay. Well, let’s dive into really some of the specifics of all these individual people you've met with and really start just generally what are some of the commonalities you saw between the people you met with? I mean, I think a lot of folks say, “Well, I would only start that second career if I needed the money.” Are they starting these businesses and these next careers because they need the money or are they doing it for another reason?

Nancy: Yeah. It’s both. And again, when you start to think about the fact that if you leave your full-time job at 60, that’s going to be a lot of years to fill, a lot and a lot of time, and I know that initially, people think, “Ah, I'm just so done with work. All I want to do is take the trips and be on the golf course and, boy, I’m going to be a happy camper,” but survey after survey shows that over time, that just doesn't hold up. People need to have a meaning and a purpose and again, it doesn't necessarily have to be paid work. A lot of people find great satisfaction from doing volunteering, but you need to have something, and the important thing to remember here is that work for as much as we complain about jobs, work really provides our lives with a lot of benefits. I mean, first and foremost is the issue of compensation and I think you need to take a hard look at that. If you are going to need to generate money during retirement, you need to be honest with yourself about that. And not only money but benefits. I think the whole issue of healthcare and getting healthcare during the time period before after you leave your job and before you're eligible for Medicare is a huge, huge issue for folks and that's not a small matter, but you need to take a look at that,

So, compensation is one thing but in addition to compensation, work gives us a daily routine and people sometimes underestimate the value of that. They say, “Oh, it’s going to be great to have just this open calendar and I don't have to be anywhere on any particular day.” Again, it's good for about six to nine months and then it can get to be very challenging. So, it's routine. It provides us the community, it gives us purpose, and it also feeds our sense of status and self-love, and that's really important as well. And so, certainly when I work with people, we take a look at all of those factors, and I have people really think about, "Okay. Now that you’re leaving your job, what is going to be most important for you to replace in whatever you do next? How important is the compensation? How important is this loss of identity?” I was talking with the gentleman the other day who was a doctor and for him this issue, money is not the issue for him, but loss of identity is a big, big issue. He said to me, "You know, right now when I go to a cocktail party and I said to people, ‘Hi. I’m Dr. Stevens,’ well automatically, people give me a certain level of respect.” He said, “I'm not quite sure who I'm going to be once I give this up.” And so, it can be a process for people to find the right combination of activities to help feed some of these motivators that work satisfy.

Casey: Kind of becomes this recreation of identity and it sounds like as you go through this coaching process with the people you work with, it’s not about just asking questions, asking the right questions to get the engine started. So, what are some of the most powerful questions that you asked during these coaching programs that you walk people through?

Nancy: Yeah. Well, we start out whenever I work with someone, we sort of take a walk through their life history. I always emphasize to people this is not therapy but that said, we do start with childhood and because oftentimes what we enjoy most when we are children and our natural gifts as children, the kid who loves putting on the shows for the neighborhood or the kid who just absolutely loves being on the sports field, people forget about that over time because they become responsible adults and it all gets buried under that, they shoots up your life, and then suddenly they’re freed up and I’ll say to them, “So, what did you want to be as a kid?” and it's really interesting because sometimes people say, "Well, you know, as a little boy I always wanted to be a firefighter but of course that’s ridiculous. I’m not going to do that now. I can’t go back to that.” And then I said to him, “All right. Well, let’s just play with that for a moment. Let's talk about what was it about being a fireman that was so exciting? Was it being outdoors? Was it being the hero who is able to go into the building? Was it helping people?” And one of the things I’ll always I’ll just keep at it. It’s sort of like peeling away an onion and it's important to get to the heart of that dream.

If you wanted to be a firefighter, what was it? Because, sure, maybe you're not going to become a firefighter at age 65 but if part of what was driving that dream was that you love both being outdoors and helping people, there are a lot of things that you might be able to do that would be good outlets for those two motivators. So, we start with childhood. We’ll talk a little bit about that and then we go through work. And when we start talking about work, well, actually we also talked about obviously the educational years and a question I love to ask people is, "So, if you could go back to college now, what courses would you take or what would you choose to major in?” And people often stop and really, you know, that stops a lot of people dead in their tracks and they go, “Well, you know what I really always wanted to do is I wanted to be a literature major but my father told me no. I can't possibly earn any money doing that.” And so, I’ll say to them, “Okay. So, what was it about being a literature major?” “Well, I love to read.” “Okay. So, let's play with that for a little while.”

So, this question of if you could go back to school, what would you major in? And also, in many ways, it's a practical question because these days you can go back to school. You may not go back to school for a degree but you can take online courses, you can take workshops. I mean, there are classes and training programs for every field imaginable. I often joke that in doing the research for this book, I came across a three-day dog walking certification program. You may wonder what could they possibly teach in three days? But the fact of the matter is, is that if you're going to be a dog walker, you do need to know about things like marketing and insurance and how do you go about getting clients and all of those types of things.

So, in any case, we go from education and we talked about work. And again, with work, even if they’re really just fed up with their jobs, we’ll talk about what were the elements of your job that you really enjoy the most. And I think it’s really important to focus not only on what were your official responsibilities but what were the unofficial responsibilities? One of my all-time favorite questions is who were you the go-to person for? Were you the go-to person for the tech problems? Were you the guy in the office who everyone came to when they were having a technology problem? Were you the person who everyone came to, to organize a company picnic? Who are you the go-to person for? Because again that speaks to your natural gifts and talents. So, I could go on and on with the questions but the important thing here is to really go through these different parts of your life and think about three key questions. What did I love to do? What did I do well? And what do I find most meaningful? Because it's really the intersection of those three, that’s where you find the sweet spot.

Casey: So, you go through this process with people, you’ve probably built this list of questions that you can like to walk individuals through and then over time, I would presume that you’ve had to eliminate some of these questions that well, that really wasn't as impactful as I thought it was going to be or that didn't get the answer I was hoping and that didn't get us to where we wanted to be. What are some questions that you found just weren't helpful?

Nancy: It really varies from person to person and I think what I've learned over time is not that the individual questions aren't helpful. It’s that there are certain personalities who are going to react differently to different questions. So, I have to go in there prepared with a wide variety of questions and when I see that just total dumbfounded look on someone's face or I can tell they’re trying very hard not to roll their eyes at me, it tells me that this is a question that doesn't speak to them. Although, I will tell you that sometimes that dumbfounded look just means that they’re like, “Wow,” and then they will come back to me the next session and will say, "You know what, I wasn’t able to answer that question while we were sitting here but it really bothered me. And I thought about it.” And so, sometimes the hardest questions can be the ones that really hold the key to what’s next.

Casey: I bet. Like me, when you ask somebody what their purposes is in retirement or what their passion, that might be the question that you get your eyes rolled on every once in a while. And why is that? Why do you think this idea of purpose or passion is it’s difficult to approach in the first place and some find it very intimidating?

Nancy: Yeah. Absolutely. That's why I think one of my all-time favorite blog posts I have this up on My Lifestyle Career, my blog, is I wrote a post about this very subject and what I said is some people are born with just a very clear passion from the time that they're very little. I have a daughter like that. Literally, from the time she was two-and-a-half years old, she would walk into a restaurant, look at the curtains and say, “Ooh, I like the curtains or I like colors of the napkins.” P.S. She now works in the design industry. I always say she was one of my easiest clients but that’s not the norm. Most people have a variety of interests and so getting back to the blog post, what I did in this particular post was I said, "Don't think of passion as being one factor. Think of it instead as being an acronym.” And so, here's the acronym using the letters of passion. P stands for people who are the people that you enjoyed being around and working with. A stands for activities. What are the types of activities that you enjoy doing? On a weekend, what would you choose to do? At work what are your favorite activities? The two Ss stand for skills and strengths. What are the things that you are just naturally good at or that you can enjoy the skills and strengths that you enjoyed developing? I stands for interests.

So, those are the first five. If you can think about those five things and you’re going to have lists for all of those then the O, the N, and the S is the opportunities and needs of the marketplace and if you can match what you're good at, with the opportunities and needs of the marketplace, that's where you’re going to find real good possibilities. Also, what I always stress to people is people recognize that passion, even though you might point something that you really enjoy, passion, being really excited about something often develops over time and it's something that people you work at doing something and over time because you become more competent and competent doing that activity, you slowly develop a passion for it. We all love, love the idea of the passion that happens in an instant. In reality, it really happens that way.

Casey: Well, and you talk a lot of these questions and things you should ask yourselves such as what are your skills or what did you enjoy? What was your passion? What did you enjoy doing when you’re a child? But you also said in your book that it's equally as important to ask yourself what you don't enjoy or what you don't want to do.

Nancy: Yeah. And I think one of the beauties of developing a second act career is by the time you are a little over 50, you’ve had a lot of life experience and over the years, you discover things about your strength but also about things that you don't do so well. And I love Marcus Buckingham has a definition of a weakness as something that just makes you feel weak, that drains your strength. And I love that because it’s not that you're not good at it. It's just doing it really saps your energy. And so, the fact of the matter is people if I say to someone, "So, tell me about the work environments you really can't stand?” Boy, people can rattle that up really quickly or if I say, “Tell me about the people who really bug you.” Again, they can tell you that without even blinking an eye and if I say, "Tell me about some of those things that you’re really terrible at doing.” Yes, speaking for myself, I am zero mechanical ability, and my husband rolls his eyes at me all the time. I’m trying to screw the top off a jar and he’s just like, “Oh my God, you’re doing it the wrong direction.” And I readily admit that. I know that that about myself.

So, most of us have a lot of easier time saying what we don’t want and what we do want. And when I talk with people about this, one of the things I sometimes bring out is I love to claim credit for this term but I actually put it in the Wall Street Journal where they talk about what's on your chuck-it list. We all hear about the bucket list, but instead, what's on your chuck-it list? What are the things that you're just at a point in life where you say, “I don’t want to do it anymore?” And it can be everything from I just don't want to have to travel anymore to I don't want to have to deal with office politics to, you know, I'm just tired of like my clients and I'm tired of dealing with sales quotas. So, we tend to talk about bucket list but I think it's equally important to talk about those chuck-it list.

Casey: Well, maybe for some it's really taking the career that you’ve had or whatever you’ve been doing for the last 10, 20 years, and focusing on this chuck-it list. I really like that and just kind of chiseling away at that career that you had and say, “Well, I didn't like this, I didn’t like that, I didn't like that,” and rather than asking that question of what did you really enjoy, let's start with what didn't you like since those are sometimes easier questions to ask to isolate those things that are left over which are the things you actually enjoyed about your career.

Nancy: That’s right. And also, I think the other thing you can do with that approach is when someone says, "Well, I'm tired of dealing with jerks. I just had this horrible boss. I don't want to deal with someone like that anymore.” So, I'll say to them, “Okay, so what does that mean about the type of people that you would like to work with?” And then they’ll think about it and they’ll say, “Well, you know, I realized I really want to work in a workplace where there's really much more of a collegial environment where people are much more supportive.” That’s really helpful information. So, sometimes what you don't want really can shed light on the opposite of what you do want.

Casey: Well, I imagine most of your coaching work is for individuals that are stepping into retirement and trying to figure out what those transition is going to look like, but I bet every once in a while you’ve met somebody that didn't ask themselves the right question, didn't ask themselves what they didn't like, and what they don't want and then ended up getting into something they weren’t real happy with and now you have to go back and fix that. You have to go back in and rearrange the puzzle and start to ask the right questions. Have you met with individuals that thought, "Well, this path is going to be very fulfilling and very easy," and all of a sudden becomes blood, sweat, and tears and it’s just not what they thought it was going to be?

Nancy: Yeah. And surprisingly enough, sometimes the people that I see are people who actually they retire and they think that what they'll do is they will volunteer that that's going to be the work part of their lives going forward and what they find is that finding meaningful volunteer assignments can actually be surprisingly challenging for a lot of people. They end up working at a soup kitchen. Nothing wrong with that but just isn't right for them. It doesn't fill those motivators that we were talking about before about things like having a predictable routine and social status and community. And so, they find it oddly like they’re at sorts doing that. And so, yeah, it happens. So, then I always say to people too it’s a process. This is a long period of time there we’re talking about. So, what works for you for the first couple of years or doesn't work for you the first couple of years, you always have time to adjust. This is not a one-time decision. Generally, when I work with people, I say let's focus on the next three years. What's going to work for you during that time period?

And also, another thing that I recommend to people which people are oftentimes surprised by is I say to people if it's at all possible, take a break after leaving your full-time job. Take six months, nine months a year. Go travel. Go do nothing. Go clean out the closets. I think it’s important to get that space from just take the time to create the space to decompress, to re-energize, and to just declutter your mind and I think then you're much more receptive to new possibilities.

Casey: That’s kind of like getting out of college and not going straight and getting your masters or your doctorate. My grandfather had his masters who’s in education for 60 years and I said, "Grandpa, should I go ahead and get my masters?” He said, "Go take a break, get into your career and make sure that's really what you want to do and it's going to create value before you just dive right in.” And I think we got all these little life transitions we go through whether it’s getting out of college or stepping into retirement and that sometimes we just need a little buffer and a little break to make sure that we can step through that and we can really have our ideal life. And that was something you brought up in your book was this concept of an ideal life and envisioning this ideal life we’re going to have in retirement. And one of the things that I want to exercise as we utilize and some the college level retirement class courses that we do with the families we work with is we walk them through a day in retirement, which is well, what time are you going to wake up? What's afternoon look like? Where are you going to eat? What are you going to do at dinner? What are you going to get out? Are you going to play golf? What's that day look like? And I never really thought about saying that as an ideal day. Not just a day, but an ideal day. And I think that's impactful. Did you pick that word ideal for a reason?

Nancy: Yeah. Well, I think is – yeah, I did and because it is important to focus on what are the ideal elements that you're looking for. And again, it may change over time, but I think it's important to think about what would really energize you, what's going to make for a meaningful day. And also, just to think about the things like when are your energy levels, what's the ebb and flow of your energy levels over the course of the day? I know for me personally, I do most of my writing in the morning because that's when I'm fresh. Late in the afternoon is when that I really need to take a little bit of a break. That’s when I’ll do more of the mindless, paying bills, that type of thing. And then sometimes I’ll get a second wind in the evening, but I think it's a great exercise for people to go through regardless of whether you plan on working or not to just think about how do you want to structure that day and then also sometimes, I’ll have clients take a look at it over a years’ time, not to have them plan every day of the year but just say over the course of a year, what are some things that you'd like to add into this? How important is it for you to take that three-week trip to go visit the grandchildren?

Or one of the activities that I heard about that I’ll be writing about in my next Next Avenue post that I heard about at the United Way meeting was a gentleman talked about at Thanksgiving each year he’s very interested in passing on to his grandchildren the idea of giving back. And so, he has each grandchild, they’re a little bit older, pick a cause or an organization that they would like him to contribute some money towards. At Thanksgiving, each grandchild makes a little presentation as to why this cause is important to them. And I thought that was so great. So, that was just an example of a meaningful activity that he plans on doing once a year. So, yeah, I think it's important to shoot for the ideal. You may not give it every day but at least you’ll be in far better shape on that average basis.

Casey: Well, I really like the idea of kind of combining those two ideas. Well, first, before we get to ideal, let’s just isolate what you think a day is going to look like in retirement and then look at that sheet, maybe take a worksheet, go 7 to 8, 8 to 9, 9 to 10 and then take out another sheet of paper and say, "Well, this is what I think I'm going to do but this is what I really like to do. This is what I think would be ideal.” I really like that idea and along those idea lines, you brought up the idea of having an idea party. So, what the heck is an idea party and have you actually seen someone utilize an idea party successfully in their own lives?

Nancy: Yeah. So, basically, an idea party and again, I’d love to claim credit but that actually comes from a woman named Barbara Sher who’s written a number of really excellent books about finding your path in life. And the idea party is basically that you pull together a group of friends and it’s a brainstorming party where you say, "Hey, you know, I'm thinking about I’d love to do something with animals. I like to give back. I’d like to do something with animals,” and then people just start sharing ideas. And it’s the power of brainstorming and it can be incredibly impactful for people to do this. In fact, doing this can really expand your possibilities. It can open up some new doors that you might not have thought about before but the other thing that happens is you get together seven or eight people in a room, you will be amazed at who knows who and who might happen to know of someone who has an organization that is looking for somebody on a part-time basis. You just never know. And again, it gets back to what I talked about before that when you get out there and you start trying things and you just put yourself out there and talk with people and start taking steps, that’s when serendipity happens.

Casey: How do you go about organizing one of this idea of parties? And who do you invite and how do you invite them?

Nancy: Yeah. So, I think it can be don't drive yourself crazy. Pick a date, 7:00 to 9:00 on a weekday night, send out an email to eight people. My only suggestion with who you pick is you really want to avoid the Debbie Downers. We all know people like that who no matter what you say they’re always coming up with the reasons why something won’t work out. And quite frankly, it can be really helpful to invite people who bring different perspectives who come from different industries because they can open up possibilities for you that you really might not have considered before.

Casey: Would it be helpful to combine this idea party with another one of the tools as you mentioned in your book called The Rejuvenation Journal?

Nancy: Yeah. I think there's a lot of different ways that people go through this process of self-reflection and introspection. Some people they enjoy taking assessments that can help them really hone-in on what are my skills and strengths. Other people that just doesn't work for them and they're much better off journaling every day and really just spending some time writing down their thoughts 20 minutes a day about ideas that they have, what speaks to them, what type of skills or strengths they may have used the prior day. That works for some people. It doesn't work for other people. So, I think the key here is to try a couple of different things and over time you'll begin to see what works for you.

Casey: And have you utilized these ideas so that in time do you do rejuvenation journal or have you?

Nancy: I certainly journal from time to time. I have to admit I'm not great at doing it on a daily basis but sometimes when I’m stuck, what I will do is I’ll just jot down some notes. For me, it works doing it on the computer. Other people really enjoy just having that handwritten journal that they can write in, and, yeah, it can be effective. There are other times when quite frankly it hasn’t worked for me but like my clients, I like to try different things at different times.

Casey: Well, and I have to ask this question because I know anybody that picks up your book is going, “What is this all about, getting paid to travel?” I’ve got so many families that I work with that love to travel and heck, as we’re doing the retirement planning, we got this little line item that is the travel budget. It might be $1,000 a year. It might be $10,000 a year. But we’ve got a line item that's actually a cash outflow. You make this sound like we can have travel be a cash inflow or at least do it free. How could we possibly travel for free and go to the places we want to go and just have a great time? Actually, I added a couple that I work with for a number of years. After reading your book, I had brought up some of these ideas that you had and he's a physician and so some these ideas really worked well in his plan and now they’re really starting to pursue that as he's stepping away from another job right now.

Nancy: Yeah. So, in the intro to that chapter, I say, "It's okay if you flip to this chapter first. I get it.” So, let’s start off with the bad news, which is that in most cases, this is not going to generate a lot of income from most folks but what it can do is it can seriously reduce your travel costs and in some cases totally eliminate your travel costs, and in some cases, you can actually earn some money as well. So, in that chapter, I put forth a couple of different ideas so I’ll share a couple of them with you. The first is and actually, I have a friend of mine locally who right now is in Italy. She started a travel service to Italy, where she has organized food tours. She does a Prosecco tour of Italy. She's doing one right now where she takes people to different places in Italy and they do cooking classes along the way. So, she earns a little from doing this, but it allows her to go to Italy to travel or to spend time with people she really enjoys. And so, it's great fun. My husband and I recently went on something called a cheese journey.

Casey: Now I’m curious.

Nancy: Yeah. So, believe it or not, so my husband is a - he loves artisanal cheeses and for his 60th birthday and I was racking my brains trying to think what I can possibly get him, and as luck would have it, I went to our local cheese shop and lo and behold there was a postcard an old fashion marketing method, advertising and I came home and I looked it up and I said, “Oh my god, this is perfect.” It was a ten-day trip for people who are cheese fans and so we went to Switzerland and France and we spent 10 days traveling. And what was interesting about that trip was not only of course that we got to stay in beautiful places and eat lots of our cheese but that the other people in the group there were about 12 or 14 people in the group were all working in the cheese industry in different capacities. We were actually, us and another couple, we were the only two couples who are not actively working in the industry. But the woman who started it was a woman who had owned a cheese shop. She eventually got out of that business, but she still wanted to stay in that world so she now does these cheese journeys and you could look them up, So, that's an example of and people do this for wine lovers and chocolate lovers. I’ve, since I’ve been paying attention toe space, discovered all sorts of possibilities.

On the sort of opposite ends of the spectrum, my brother and his wife just returned from a 27-month stint in the Peace Corps. They were stationed in Moldova for two years plus a three-month training program and while they were over there, now technically Peace Corps is volunteer but all their expenses were picked up while they were there, including health insurance. They did get paid a stipend at the end of their commitment and while they were there, they got to travel all over Eastern Europe and then they did a trip to Europe afterwards. So, there are ways of doing this. Again, I wouldn't plan on earning millions doing most of these ideas but it can be a great way to reduce the cost of your travel in lots of fun ways. On my blog, I talk, I have a fun article about travel bloggers. There are a growing number of boomer age travel bloggers who travel around the world, they write about their adventures, in some cases, they’ve written books, and then they get sponsorships in return for writing about certain types of travel services. So, lots of different ways that you can do it.

Casey: So many different ways, so many different things to do while you step into retirement. From my seat, I get to see hundreds, I’ve seen thousands of retirees and what they're able to accomplish and it runs a gamut. I mean, it's just as broad during your working career and the different types of ways you can make money as it is, as you step in your second act career if you will. You already shared some unusual experiences that you’ve had and I'm wondering at what is the strangest or most unusual second act career that you’ve run across?

Nancy: Well, I think that prize we go to in the book I feature Bob Alper who was a rabbi, still is a rabbi, who became a standup comedian and he had a congregation in Philadelphia and for a variety of reasons, I mean, needless to say, it was a funny interview. He’s a really entertaining guy and he said to me, “I didn’t get kicked out. I chose to leave,” but he decided initially he was sort of tired of the full-time commitment and always having his weekends, he’s spending his weekends working, and he really wanted to have his weekends for his family. And so, his initial plan was he was just going to be sort of a freelance rabbi. He would do people could hire him for live events for bar mitzvahs and weddings and that type of thing. In any case, he was literally sitting in his office about a month after he left his job and he was looking at the local Philadelphia Jewish newspaper and he saw this tiny little ad for a standup comedy open mic night. And everyone had always told him that he was very funny.

And so, he went and he did it. There was a local reporter who happened to be there, who covered it, who of course thought it was quite amusing that he is a rabbi doing this. It ended up on TV. One thing led to another. He now plays at different event spaces throughout the country and what’s really interesting though to me that his story is he said to me, "You know, I know it sounds like a strange transition, but when I see people laughing at my jokes and when I get letters from people who say, ‘My wife had cancer and the one thing that really got her through her treatments was listening to your CDs.’ I still feel like I'm doing God's work.” And I thought that was a great example of taking their strengths and just building on that. And one of the really interesting things that he ended up doing was he now does what they call the Laugh In Peace Tour where he travels to college campuses with a Muslim cleric and a Southern Baptist minister and the three of them together perform, and again he said to me, "You know, I really think I'm opening people's eyes and I'm still doing God’s work just in a very different way.”

Casey: Well, I’m going to have to look these guys up. Do you have their name off the top your head?

Nancy: His name Bob Alper.

Casey: Is that…

Nancy: A-L-P-E-R.

Casey: A-L-P-E-R. All right. Well, I’m going to have to check that out. Now, if you have time, I know we’re getting short here on time, but there is one philosophical question that I like to ask every one of our guests and have asked thousands of retirees over time and that is what does retirement mean to you?

Nancy: A second opportunity.

Casey: And as far as the second opportunity goes, that could be an opportunity for what, in your mind?

Nancy: Yeah. I mean, to me retirement is a point in time particularly for folks these days where you are finally freed up to do what you want to do, you’re freed up to share your gifts with the world in a way that really speaks to you and quite frankly, it’s an opportunity to just have fun. And that's what I love about the people who I interviewed is a lot of them I don’t mean to make it sound like they’re not working for it. A lot of them are working really hard but they’re having a great time doing it and they find a tremendous meaning in what they're doing. And so, to me, that's the best side of retirement if you can find what really makes you smile.

Casey: Well, and I love what you said about sharing your gifts with the world. As we step in retirement, I just don't believe that we were blessed with these gifts, these talents, and had all these experiences that have accumulated over the years and were just supposed to keep them contained and not share them with the world so that we can really use these gifts and talents like we were really meant to be utilizing them in the first place. So, thank you so much for sharing that with our audience. And before we go, Nancy, where could our listeners find you, communicate with you?

Nancy: Yeah. They can find me in two places. One is my personal business website which is and there are lots and lots of resources on there of people. I have a free newsletter. I won’t bombard you with emails that contact just twice a month and, in the newsletter, I have links to interesting second act stories and along with the newsletter, people can download out an e-book that I put together about 25 great questions to consider when planning your second act so I encourage people to come to the site and to do that. And the other place is you can find me at I write a column for them about working purpose, and it's also syndicated on and, of course, they can get the book on Amazon or at local bookstores.

Casey: And that's where I actually found you. It was Next Avenue. So, thank you for that, and the great articles that you put out. Thanks so much for coming on and sharing with us more about you and your philosophy and your book. I look forward to having you hopefully get together sometime and have some artisanal cheeses if we can.

Nancy: You bring the wine. We’ll bring the cheese.

Casey: Sounds good. Until next time, Nancy. Thank you.

Nancy: Thank you.