6 Steps to Finding Your Second Act in Retirement
What makes lists so appealing to us? Don’t miss today’s episode of the podcast where the boys give “next-step” advice and discuss the ability we have to create the best retirement process possible by following a few simple steps.
The Teaching Transformations Podcast. Join Tim Desmond Ryan Wooley as they help teachers in their late forties or fifties to design a post-academic life.
Seize the Day!
Welcome to Teaching Transformations: Designing Your Post-Career Life with Tim Desmond and Ryan Wooley.
You’re a music guy.
A little bit.
Who are your top three guitarists of all time.
That’s an easy question. Jimi Hendrix, Stevie Ray Vaughan, Eddie Van Halen.
Did you think I was going there?
That’s about what I would expect. Stevie Ray Vaughan’s an interesting choice.
Yeah. Those three are based on the fact that they changed the way guitar was played in my opinion and Stevie Ray specifically with that Texas Blues sound where it sounds as though there’s two guitarists when there’s only one. Obviously Hendrix was a pioneer there, but I think Stevie Ray, especially with that three piece with Double Trouble, like, you listen to some of those live recordings and you swear there’s two guitars there. How about you?
Good choices. I’ve never been a Hendrix guy, though. I mean, I appreciate what he brought, but Van Halen is definitely like number one for me. I play a lot of acoustic stuff, and I have an appreciation, probably a bigger appreciation in some ways, for acoustic music than rock in many ways. Andy McKee, have you ever heard of him?
I don’t know if I have.
He is amazing. He does songs that are so complex, and he’ll do covers. He did a cover of Tears for Fears’ Everybody Wants to Rule the World, and he does that by himself on acoustic guitar, but he does the baseline, the melody, like everything is just coming through what he’s playing on guitar, and he doesn’t sing, so he’s pretty incredible. Leo Kottke would be up there. I don’t know if you know him.
Yeah, I know him.
Yeah. I wanted to start by asking you your top three of something because I feel like we’re surrounded by lists, and I realized, I don’t know if you’re like me, but I totally get sucked into these all the time like when I’m surfing. Do you get pulled into lists of things?
Oh, yeah. We all do. I don’t think there’s anything necessarily underhanded or evil about that, it’s just how we’re wired. As creatures, we need to categorize and organize things, so if you put them in a list or you stick some numbers on them, we’re much more likely to pay attention, so it’s nothing new. It’s nothing devious, but yeah I’m much more likely to click on a listicle than I am an article.
You call it a listicle?
I’ve never heard that term.
It’s a content marketing term.
It seems like it’s everywhere, and I don’t mind it. I don’t think there’s anything bad about it, either, but it’s funny. When you really pay attention, it seems like the vast majority of pages out there revolve around a central list of something.
Well, it also ignites engagement because anytime you rank things, unless it’s completely 100% objective, which is rarely the case, it grounds for an argument. Any time Rolling Stone comes out with this like 100 Greatest of whatever, there’s people fighting about it.
That’s a good point. I found this article about the top four reasons people like lists on The Good Badger. It says number one, for improved organization. You already mentioned that. Number two, we’re stupid. It’s a way of, I guess, simplifying the world for the sake of argument which is basically what you were just saying and to build a common reality. This reminds me, when I worked at the university, there was a committee on committees.
The one that’s not on here, though, is one of my favorite lists of all time–David Letterman’s Top 10. Do you remember those?
Yeah. Maybe that the origin of the list movement. Would you say?
In mass media, it might be. There were a lot of great things about Letterman, about the Late Show back in the day, but I never missed the top 10 list, like that was what I was looking forward to, so yeah, maybe there’s something to that.
So, going back to your point about rankings and about inviting conversation, it invites argument, right? It invites people to take a stand on something. What do you think about something like college rankings?
That example in particular is probably a sensitive spot for the two of us given the age of our kids, but I feel like there are certain things like college rankings that are, I don’t want to call them political, but there’s a whole lot more factors that are involved in that, and I feel like there’s currency being exchanged in situations like that. Not necessarily money, but currency, and a lot of influence that affects those, you know, like the US News and World Report rankings. I don’t put much stock on those. I think something similar is like “the 50 laziest cities in the country”, those kind of lists. They’re not even worth arguing about. Now, if you’re talking about like the 10 sunniest cities, that’s got some pretty hard scientific data behind it. I feel like there’s a lot more variables under the surface.
I agree. My son gave his eighth grade chapel talk speech, that the speech that all eighth graders have to do, on college rankings, and he was arguing against them. I think both he and I really internalized his arguments, but for the most part, they really are innocuous, they do invite sort of conversation, and they do help to clarify thinking. I do think it’s helpful. I’m going to read this quote from the article that I mentioned, The Top 4 Reasons People like Lists. It says, “If I’ve got a proven money making method, which book are you going to buy: How to Become Wealthy with Rigorous Research, Long Hours, High Financial Risk, and Patience or Six Simple Steps to Earning Seven Figures?”
Yeah. I would even take it a step further and say How to Become Wealthy in Seven Steps with Rigorous Research, Long Hours, High Financial Risk, and Patience, and it would still outsell. You have people who want the recipe, they want this to tell them exactly what to do even if it’s hard sometimes. So, there’s no question about it–there’s some psychology involved there.
Yep. Well, in today’s episode, I want us to talk about an article that I read, and I’m going to share a little bit about it, but it’s one of these list articles because of this project. Because you and I are talking a lot about second act and stuff like that, I’m doing a little bit more reading and poking around, and I liked this article. It’s in… Kiplinger? How do I say that?
I don’t know. I don’t think I’ve ever said it out loud.
Yeah. There are some things I just never say. I see it all the time, but I probably should have looked that up before. It’s called Six Steps to Finding Your Second act in Retirement by Mary Kane, and it was published almost a year ago, May 22 of 2020. Before we get into her list, I just want to pull out a couple of stats that I think are interesting that she refers to. She points out that more Americans are working well into their “retirement years.” Labor force participation rates for men ages 65 to 69 reached 39% this year, up from 28% in 1995. That’s a big jump. Rates for older women climbed to 30% from 17% in the same period. What do you make of that?
Well, there’s a couple different ways you can look at it. I mean, pessimistically, you can say, people haven’t saved for retirement and that means they have to work longer to sustain their lifestyle, but I think that’s an oversimplified explanation. I think there’s a lot of play here. Another possibility is that people are just redefining what retirement means. I don’t know how labor force participation rates are determined, but if you happen to be a fully “retired person” and you’d like to work 20 hours a week at the local bookstore because you just love books, you’re in the labor force, but you have to be there. Is that necessarily a bad thing? It would be hard to parse that out. I think we would need some more data to come to any kind of conclusion, but to me, it just says the nature of retirement, and what it means is just not what it was in 1995.
Yeah. Either way, it means you’re not sitting around watching TV.
Correct, which is probably what our parents or early Boomer definition retirement was, like you stop working, you no longer get a paycheck, and you just at home or you’re traveling, but you’re not working.
Alright. Here’s another one that’s interesting. 26% of all new businesses were started by adults ages 55 to 64 in 2017, up from 15% in 1996. 26% of all new businesses started by people between 55 and 64. That sort of supports your argument that it’s not so much about just having a job because you need one. If you’re starting a business, not only does it take energy, but it requires a level of risk that you probably wouldn’t take unless you could be taking that.
Right. I don’t have the exact source, but I know that in the circles that I run in, there’s a lot of talk about Gen X really driving entrepreneurship right now, like statistically speaking, it’s people in their 50s that are more likely to start a business than any other age group, and I think that shatters a lot of preconceived notions about what it means to be an entrepreneur. It’s not just the Silicon Valley Tech Bros in their 20s who were creating these startups, it’s Gen Xers that are really driving it, and four years later, I’ll bet that percentage is even higher. Also, the other thing I’d like to underscore here is that the definition of business has changed. In the early 1990s or in our parents generation, starting a business meant some sort of brick and mortar operation. It was a whether you ran it out of an office, whether it was retail or a service industry. A small business meant you had an actual physical business, and since the advent of the internet, thanks again, Gen X, that doesn’t have to be the case. If you’re an Amazon reseller and you have an Amazon page where you resell certain products, you never touch inventory, you know, you leave the filament to Amazon. That’s technically a small business, and if it makes you $200 a month, it’s still a small business, so I’m not surprised by those statistics. I think they’re going to go up, especially post pandemic when people have realized that that single employer, that single source of a paycheck is not as secure as they thought it was. I think more and more people are going to be creating, whatever you want to call it, side hustles, additional revenue streams, second jobs, whatever. It’s only going to go up from here.
I think I’m going to start a video rental business.
You know what you should do? You should start in Portland because I hear they only have one rental place in that whole town.
Remember the VHS rentals?
Oh, man, do I? Yeah. Gosh, I mean, that was sort of a mainstay for my wife and I. We were living in New Jersey in the 90s, renting a house in Morristown, and there was an independently owned VHS rental place that we could walk to, so Friday night, that’s what we did. We went out to dinner and got some drinks, grabbed two or three VHS cassettes, and walked home and watched them.
Yep. Did you make sure to rewind before you turned them back?
Well, if you want to be kind, you have to rewind. How many of those stickers did you see in your lifetime?
Alright, so I want to look at this list. I think it’s interesting, and like I said, I read a ton of these kinds of things in, but I like this list, and I want to get your take on it. I’m going to read each of these six items, and then I want to take some or all of them one at a time. We’re talking about, let’s say six steps to finding your second act and retirement. Step one, begin early. Step two, fix your finances. Step three, build a bridge. Step four, do a midtermship. Step five, tackle the internal work. Step six, take it slow. Before we get into the specifics, what do you think of that list?
I think it’s very generalized, but it’s solid. It really is sort of an umbrella, high altitude overview. It works. This is a bit of a tangent, but it’s related, and I know this from being a certified content marketer. In the content marketing world, the idea is that you provide very valuable content to people, you give them the what, and you sell them the how. So, this is all about the what, and that’s totally fine. There’s nothing wrong with that. If you’re looking at this list and you’re like, yes, that’s exactly what I need to do, spot on, I totally agree, the how is where, you know, the devils in the details there.
Yeah. You might write an article like this, a list that is very general that pulls people in, and ultimately, they’ll need more specific information which is what they’ll get by forming a relationship with you, right? Is that kinda how it works?
Yeah, and there’s a few nuanced options here. If you’re an affiliate marketer, what you could do is, let’s say, fix your finances. That’s a good example. Alright, so what you might do in this article is you might link out to a financial service associate where you get an affiliate commission, so if someone clicks through and hires that person, that person kicks you back. Again, this is all aboveboard, there’s nothing scammy about this. This is how affiliate marketing works. It doesn’t cost you, the customer, anything, so that’s one way you could do it or you could have some type of financial tune up video course that you have for sale. You could sell them a product or service yourself, or you could sell them an affiliate related one, but yeah, that’s basically how it would work.
So, I recognize “begin early” is very general, all of these are, but can we try to color these in a little bit more? For you, begin early means quit your job at 46 or 47.
No safety net, throw it all away. No. When they say early, I think they mentioned early sixties in the article, and I was like, I’d be thinking about a little sooner than that. I think that’s what we’re trying to do here, right? I mean, we’re trying to say like, okay, as you’re starting your fiftiess, you have a very nice, comfortable onramp, you have a lot of time at the same time. We know at this age, the time goes by very quickly, so you don’t want to squander it. I would not wait until I was sixty before I started thinking about this, but begin early just means start thinking about the things you enjoy, the things you might want to do. Earning money is, there’s a lot of studies that say that there’s a lot of intrinsic value for humans in that way being compensated, so it has to be more than just, well, I really like to lay on the beach, so that’s what I’m going to do. There needs to be some sort of purpose behind it, and purpose is usually driven through compensation. I would say if you’re in our demographic, this is the time not to quit your job, but it’s the time to start thinking about, what are the skill sets that you have that you can apply? What are the industries that interests you? What are the hobbies that you have that you would like to get paid for? That’s what I think begin early means. What do you think? Am I kind of on there?
That’s really what we’ve been talking about through a lot of our episodes and what Mary Kane recommended was at least five years before your retirement, and again, that’s gonna vary with all of our situations, but that’s not a bad target. That gives you something to shoot for if you have no sense of when to start.
I would be more conservative with it. I would say probably ten years out, but yeah, at a minimum, I would say five.
Right. See, this is doing what we said, it’s inviting us to take a position on this. I agree, actually. Five would probably be on the light side, and ten is probably better, I think. We joked about you making that leap when you did, but we’ve also established, you know, you really started this process pretty much ten years before you made the leap,.
Pretty near, yeah.
It takes a while, and we know it’s going to, and that’s assuming you didn’t wander around for five years figuring out what you wanted to do. You started building yourself as an independent author, and it still took that time, so if you build in some sort of self discovery time that might be required and maybe making some false starts, I would say you’d really need even more than that.
Yeah. You can’t start too early. There’s no harm. Whereas if you start too late, then you’re gonna have problems. Even if you’re in your thirties, you can be thinking about the next chapter the same way you think about your retirement fund allocation, like you think about that periodically in your twenties and thirties. Why wouldn’t you think about what you’re going to do with your time in that same window?
Yeah. The second point bugs me a little bit, I have to say. Just the way it’s put–“fix your finances,” like it’s something that you can just, oh, sorry, I didn’t realize I needed to fix my finances.
Oh, they’re broken? Oh, really? I didn’t know that, thanks.
This one’s a tricky one. I know so many educators in both K12. and higher ed, and they vary widely in terms of their financial picture. Not that I really know it in detail, but I kind of have a sense just from comments that I hear people make, and that’s going to be true, but it’s also just not simple. We all have a lot on on us, you know, we have a lot of responsibilities, we have have to provide homes for ourselves and our families and college education to kids if if we have them, all those kinds of things. It’s one of those things that I know is very real but I think is way easier to say than to do. It’s way easier to say, oh, just pay off your debt, get that taken care of. Okay. How do you react to that one?
If it fills you with dread or if you’re in a state of denial, and you’re finally like yeah, my finances are not in good shape, I would say now is the time to get some professional help. There’s a lot of different programs out there. I’m not a big fan of Dave Ramsey, but his snowball method seems to work for a lot of people in getting out of debt. Whether it’s something that you know, a program you do on your own, or you hire someone, or even if you get a debt consolidation service and you take your high interest debts and combine them into something manageable, it’s not an overnight fix. If you’re tens of thousands of dollars in debt, that’s not going to change in two months, but my takeaway from this is that you should be doing something right. Even if that something is, I’m going to start by curtailing my spending, or I’m going to start by getting tighter with my budget, I’m going to start by cutting up the credit cards, like everyone can start somewhere, and I think that’s the key is just to get off the blocks to start it and be patient because it’s going to take some time. A lot of people, and I don’t know numbers either, but just in conversations I’ve had with some people, they’ve said, I don’t have a retirement account, I’ll just whatever. I wouldn’t want to be in that situation. Again, you’re not going to fix that overnight, but it’s got to be on your radar. You’ve got to be taking it seriously.
Yeah. Well, we talked in a previous conversation about… this is not most educators’ favorite topic to think about in our experience. We don’t like thinking or talking about money. I’m going to pull a little trick here. I’m going to do a nested list inside of a list conversation.
Wow. Okay, the top three nested lists lists.
This goes back to you can’t really do a search without coming up to a whole bunch of lists. When I was considering, like, what is the financial picture of Gen Xers like us and in general, and I got to this five interesting facts about Generation X. One, they have the most debt. Two, they’re stressed about being sandwiched in the middle meaning taking care of their parents and taking care of their kids. I do think that as a generation, we spend a lot more on our children than previous generations did.
Yeah, college alone.
But we provide more, in my experience. They are more pessimistic about their financial future or financial picture. 401K’s are the vehicle of choice, and they desire balance and flexibility. There is research behind that. We do have the most debt, and I do think there’s something to that we feel like we need to spend more in both directions. Does that come from like a sense of responsibility? I don’t know what that is.
Yeah, I think it does, and I think we’ve talked about this in a previous episode about being bookended by generations that still need our custodial help, so that’s just the reality of the situation for most of us.
So bottom line: fix your finances.
Yeah, just do it.
Alright, so back to the main list. Number three, build a bridge. Back to your point, I know some of this is perfunctory, as a general guide, I think this is the side hustle, right? You got to start doing something even if it’s exploratory. So, talk about how that played out for you.
I think educators in particular are very susceptible to falling into a pattern of resistance through eternal learning. I’m just gonna read another book, I’m going to take another course, I’m going to study this. The rationale, the justification is like, I’m just being prepared. But in reality, you’re just delaying the inevitable, or you’re falling in into resistance. So in number one, when we say begin early and start thinking about it, like, yes, that’s absolutely the beginning of the process, that’s when you’re doing your research, you’re talking to people, you’re reading books, but at some point, you got to start doing something. Again, this is where educators kind of come up short. Doing something means you’re going to have to take a risk, you’re going to have to try something, and the first idea might not work or the third idea might not work, but building a bridge, starting a side hustle, getting that first client or that first customer, that’s going to tell you so much more about what you want to do. I mean, we’re hopefully modeling that example, like you and I have had this conversation publicly and privately. I would have loved to have gone off in a room somewhere for six months and built this wonderful course for Gen X teachers about what to do in retirement, but I know better now, and I know that we have to build the audience. First, we have to start small.We have to ask the audience what they want and start building that, so I think building a bridge is that same concept. It’s, get started on something so that you can test and start to iterate. If all you have is a collection of ideas in your head, they might work brilliantly for you. That doesn’t mean they’re going to work in the real world.
Yeah, and I tend to be a contemplator, so I need to constantly be reminded or to remind myself that I need to take action. That’s something that I’ve long, admired in you is you really are good at that, at taking action. You don’t always know where it’s headed or what the outcome is going to be, but if you take action, you’ll find your way there, and that’s critical. A lot of us, we’ve been in careers for a long time, and we have our routines. We grade papers, we make dinner in the evenings, whatever it is, but somehow, someway, you’ve got to find a way to start to at least experiment, poke at stuff, if not making deliberate steps to build or to establish relationships with others. The next one’s a little interesting. It says, do a midterm ship. I’ve never heard that term before.
No, me neither.
It kind of suggests that there are organizations out there that invite internships from people who are post career or late career. What do you make of that?
I was a little less clear on this one than some of the others. I worry a little bit that a midterm ship is feeding into that resistance of not taking the risk yourself. You’re wrapping yourself with the protection of some other agency or organization as opposed to doing something your own. However, I will say this. If you become a midtern or you work for one of these companies in the early stages of your begin early stage, that might help you to figure out what you want to do, but at a certain point, I would not rely on the midtermship because then you’re just replacing one employer with another essentially.
Maybe it would be a good way to explore something like if you’ve been in medicine but you’re thinking about doing financial planning, maybe that’s how you find out if you really would like it as much as you think you might. Maybe it’s more of a self discovery.
Yeah. In that circumstance, it works. Well, you just have to be very cautious that you’re not going down the same path but with a different organization.
I agree. The next one is one that I want to circle back to at some point. I kind of want a full episode on this one. It’s tackle the internal work. What’s your take on that? What is that?
I don’t know, this one’s a bit fuzzy. I’d like to hear your interpretation first.
I think it’s all about discovery or rediscovery. There probably are different ways of thinking about this. I’m sure there are probably a lot of people who say to themselves, well, I’m fifty or whatever, I’m not discovering myself, I know who I am. That’s what’s been happening to me as I’ve gotten older and wiser, and I respect that, like I’m not questioning that. I think to a certain extent, we all feel that way, but I do think life stage changes present an opportunity to rethink and rediscover, so maybe it’s because you suddenly have time that you didn’t have before, and that made all the difference. Maybe there are things that you really would have liked to be doing or would have been doing but there literally just wasn’t space in your day for them, and suddenly, you’re an empty nester and you have time and space for that. That’s a different reality. Maybe in the past twenty-some years, you’ve changed since the last time you had that space, so that’s the way I read it. That’s why for me, I feel like this might be the number one item for if I were making my own list,
That’s interesting. I’m gonna look forward to a full episode on going deep on this one because I had a slightly different interpretation of the internal work. I almost heard it like, get your shit together. Tackling the internal work would be like your relationships, your health, your physical well-being. I think that element gets missed a lot when we talk about retirement because I found that if I don’t have a solid, healthy foundation, nothing else matters. If I’m in some type of chronic pain or discomfort, I can’t do anything. I think that becomes increasingly important the older we get, so for me, too, part of tackling the internal work is like, I know people don’t want to hear this, but are you eating the right stuff? Are you getting enough sleep? Are you exercising? These are just sort of common pillars. We all know it. Whether or not we do it is another thing, but I don’t think that can be minimized. That’s an important part of the internal work is like, if you’re not exercising on a regular basis, you’re gonna struggle with stamina, and it’s gonna get worse the older you get. I don’t know, maybe that’s a different angle or a different perspective, but that was kind of my take on it.
Yeah, I agree with that, though. That may also be connected to life stage. Maybe you’ve struggled to find time. I really love daily exercise. There are days, most of my days, actually, where I just don’t have space. The only way to have space is to lose sleep, which I feel like I need, or not do something that I need to do. I just don’t feel like I have that option, but it’s getting better, and I know it will continue to get better. I guess that’s the other thing is don’t miss that opportunity. If you are finding time as your life stage is changing, remember that we all need this and try to build it back in if you’ve been neglecting it. The last one is take it slow. I don’t even know if I would say mixed feelings about it, but what do you think about that? The take it slow recommendation?
It’s not what I did, but it’s what I would recommend. Take it slow kind of ties into everything else we’ve talked about as far as coming up with your ideas and building a bridge. For me, the spirit of this means that you’re not going to fix everything, like tomorrow, you’re not going to have a plan mapped out in a week. It’s gonna take some time, and that’s why we’re talking about this stuff now because we know we have the time collectively, and we have the ability to take it slow. If you wait until you’re sixty-five, you just don’t have the time to prepare. It’s a bit fuzzy for me, but I think it’s just a reminder to be patient.
Is it fair to say that our primary message with this project is to get started sooner than later?
I mean, as you wrote in the notes, it’s our Reason Dieter.
Oh, I mispronounced that. Yeah. It’s the whole point, it’s what we’re banking on with this whole thing. I mean, go meta for a second, but we hope this turns into a business idea of some sort because we think it’s that important. We think it really matters, and that’s why we’re targeting primarily educators in our age group. This is not an accident. This is the whole reason we’re here is like, start now. There’s no harm in starting now. There’s nothing you can do now that’s gonna hurt your future. Nothing.
Yeah, and it does take time. That’s one thing about our life stage that we all share is we have more risks involved. Unless we’ve started over somehow with terms of where we live or something like that, most of us have things to lose. The whole thing about Timeline, like, start, start now, take it slow. It allows the process to breathe a little bit. I think we make better decisions when we’re not on our heels which is what happens when we reach a place and suddenly have to make choices. I think we’re saying avoid all that, so I guess it’s all there. So, we just did this, should we just end? Do we even need to podcast anymore? Because I feel like we basically gave a guide?
Yeah, and you know from all your classroom experience that you only have to say things one time and people just automatically learn it.
We set it and we credited it? Cool. I didn’t know it was gonna be this easy.
Alright, in all seriousness, before we take off today, this is Episode 19. We have one more to go on, then we’re going to take a little bit of a break, and we’re going to be asking you what you want to hear. We’re probably, hopefully, maybe bringing some other people on the show, doing some interviews, but we’re gonna take a little break and kind of map that out. That’s just a reminder that that’s coming if you’re listening in real time.
Thanks for listening. Go to teachingtransformations.com and get instant access to Transformations, the free weekly email with the best personally curated resources to help those in their late 40s or 50s to design a post-career life.
Transcribed by https://otter.ai
Transformations – The free weekly email with the best personally curated resources to help teachers in their late forties or fifties to design a post-academic life. – https://teachingtransformations.com/
6 Steps to Finding Your Second Act in Retirement – https://www.kiplinger.com/slideshow/retirement/t012-s004-6-steps-to-finding-your-second-act-in-retirement/index.html
Teaching Transformations Podcast – https://teachingtransformations.com/podcast/
Intro and outro music by Penthouses. “Come to Ohio” from The Weatherman album available on most music platforms.
*Full disclosure: Some of the links are affiliate links.