Podcast: Joe Casey — Retirement Wisdom

Episode 31 of the Boldin podcast is an interview with Joe Casey — founder of Retirement Wisdom. We discuss shaping your life after retirement, and what reflection needs to be put in to be successful.

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Full Transcript of Steve Chen’s Interview with Joe Casey

Steve: Welcome to the Boldin Podcast. Today we’re going to be talking with Joe Casey, a retirement and life coach and former Merrill Lynch HR executive, and also founder of Retirement Wisdom. We’ve met through the magic of Twitter and have been sharing some notes over the past couple years. Okay, so with that, I’m just going to dive right in. Joe, I just want to kind of get your perspective on, why did you get started with this work? And why do you think that the non-financial aspect of retirement planning is so important?
Joe: Sure. So my path to this type of work came through my HR background. And I decided after my corporate career that I wanted to become an executive coach. And that’s my main focus, I have a practice that’s 10 years old, and spend a lot of time there today, mostly in financial services, but also some high tech and healthcare. And about halfway through, five years in, I started to get a lot of requests from clients about, could you help me figure out what to do next? Number one, I was coaching a person who I was hired to groom to be the successor to the CEO. About two months into it he said, “I have to be honest with you, I don’t want to be him, I want to retire at 55,” which was in three years, “and I want to do something different, but I’m not sure exactly what.”
Joe: He was pretty vague. “Can you help me figure that out?” And so began to work on that. And that started to come up more and more, a lot with women in their 40s saying, “I don’t want to do this forever. How can I get involved in not-for-profit boards?” And so I began looking for a tool, found one, an assessment tool that could help the clients, and really found that type of work rewarding. So I do both executive coaching and retirement coaching. But on the financial side, I’ll give you a couple of answers there. One, I think it’s really important because retirement’s changed so much. Back in the day, it was a pretty short period of time. Now it’s 20 to 40 years, if someone retires early. That’s a big expanse of time that requires some planning.
Joe: You could certainly wing it, but if you think about the discipline it takes to save and invest for an early retirement today, that’s probably not the best approach. And one way I think of it is that people have gotten the message that you have to plan for retirement financially, but tend to put off the, what do I do with my life in retirement? Because after all, how hard could it be? But if I can take you back to thinking about when you were in the sixth grade, sounds like a strange thing. And it’s May or June and you start the process of counting down to the last day of school, and that bell goes off and everyone runs out. And it’s a great time because everyone’s thinking about, I don’t have to go to school anymore. Summer’s here, get to do whatever I want.
Joe: A lot of people use that same sixth grade approach to retirement. I can’t wait to not work, but they don’t give enough thought in planning to, what am I going to do with that big expanse of 20, 30 or 40 years? So we help people work through that. We work with people from diverse backgrounds. The answer is different for everyone, which is a little bit of a surprise, but it helps to invest some time in planning just as you would on the financial side.
Steve: Yeah, that’s great to hear your perspective Joe. One of the things I quote all the time is something you shared with me, which is, for the average kind of knowledge worker or executive, they retire and then they kind of kick around for two and a half years and then they come back and they’re either a small business, they’re consulting, or they’re nonprofit, and they’re kind of back in the mix. And actually with that, are they back in the mix part-time or full-time? What do you see?
Joe: Well there’s a couple of things going on and we’ll talk about the examples of clients later, but we see a mix. Most people are working part-time, they’re doing something related. There’s a group that goes off and does something different, but most people turn their skills into something that can be pointed in a different direction. Sometimes moving out of the corporate realm, going into not-for-profit, more mission-driven work. Sometimes really hanging up a shingle and doing their same type of work for a different group of people, or they may move.
Joe: What’s also interesting is that there’s research now that shows that about 20 to 25% of retirees in both the US and UK are un-retiring within the first five years. And it’s surprisingly not because of money, it’s because really if they want the challenge, they’re a little bored and they miss a lot of the non-financial benefits that we get from work and we tend to take for granted, things like structure, purpose and challenge.
Steve: Right. Yeah. I mean, I could see that this idea of kind of mini-retirements or sabbaticals becoming a much more popular idea, especially as people live longer and healthier lives. Joe back to your… I really like this design your life idea. I did see that book. I’m going to have to go… I think I skimmed it, I need to kind of revisit that because I think that’s such an important… It’s almost like it’s becoming an option for more and more people. I mean when I look at society, you know we all used to have to kind of… You know, we were born, got educated, worked, passed away, didn’t have really time to think about it.
Steve: Now we’re getting more and more productive. There’s more and more ability for us to be thoughtful about our lives. What’s happening though is a lot of our time is getting consumed by distractions with these mobile devices and, you know, Twitter, Facebook, all these things, online games, they’re competing for a lot of people’s time. And a huge amount of energy is going to that because people aren’t being thoughtful or intentional about it. But there is this opportunity, it’s like, okay, if I do have the ability and 10 years of really good human capital to put to work, how am I going to use that time? You know? Or 20 years, what am I going to do, right? Let’s think about it and really kind of create a plan for it. And would love to-
Joe: Sure. Just to clarify, when I talked about the three to five years, it’s directional. It’s really evolution, not necessarily step-by-step type of things. And just to do their work justice, I should clarify that. What they’re doing is they took the principles of design thinking, and they both came out of Silicon Valley. One was involved in the design of the mouse at Apple, and one was involved in the design of the trackpad. One ran EA Sports. So they’ve got an interesting background. But they took that, the principles of design thing, and applied it to, “how can we use that to design the rest of your life?” And so it’s very good in terms of the next chapter, not the 20-year plan and not the 40-year plan, but what directionally are some things I want to pursue looking at from different angles?
Joe: And I think it is evolutionary. One of the key lines that they use that stuck with me is they described the process as a way of iterating your future. So you start down a path based on the insights and thoughts and reflections that you have, but you got to be open to the experience. You to to be open to different possibilities. And I think that’s the real genius in it. But you’re going to reality test things. You’re going to experiment and you’re going to really see, and you’re going to be better educated about the ideas and direction to come up with. But the iterate your future is, I think, a great way to think about it.
Steve: Definitely the idea of forcing yourself to be patient and thoughtful sounds super important because we spend so much of our lives kind of zipping from one thing to another.
Joe: Absolutely. And I want to be clear, it really depends on the person. That’s my biggest take away the five years I’ve been involved with the retirement coaching and 10 years with executive coaching, is it really depends on the person and where they’re at. But I do agree that there is a lot of reflection involved throughout this. And one thing I could bring to the table on this that may be useful is there’s also the life course that really comes in here because a lot of retirement involves the aging process, and isn’t often talked about. But there’s three books I’ve read in the last few years, but they all came up with the same main message. First one was Richard Rohr, who is a controversial Catholic priest in New Mexico, wrote a book called Falling Upward, and it’s about the spiritual side of the second half of life.
Joe: Wayne Dyer, who wrote a book called The Shift. And then more recently this year, David Brooks, New York Times commentator who wrote a book called, The Second Mountain. But the main theme is that the things that motivates us in the first half of life are centered around achievement, around doing acquisition, ego, those types of things. But as you get into the second half of life it’s more about contribution, less about self, more about others. And as Dyer put it, it’s moving from success to significance.
Joe: So we see that, I see that in my personal coaching work where that’s never up front as much, but is certainly something that emerges throughout the process and it does involve more reflection than action. I think ultimately though, most of the people I work with want to do something else. It takes some time to define it because it’s not going quick. We usually work with people for about six months, sometimes a year. So it’s not happening in rapid succession, but there’s this exploration process, there’s this experimentation process, but it starts with the reflection. A reflection of where they are in their life and what’s most important to them.
Steve: Yeah. Joe, I think you raise an interesting point here that this process is mostly one-on-one. It’s like you’re coaching people one-on-one versus, you know, there’s not an institution or a place where the community kind of gathers. So there’s schools, there’s companies, right? We have that early in our lives. And then afterwards you kind of have to make your own, right? Create your own community and place to meet up, or find other people.
Joe: Yes, you definitely have to find your own way because retirement is changing so much. And I think a lot of great points that we raised. There are some communities and group organizations sprouting up. I know you, I think you’ve done some stuff with Jeff Tidwell, what’s Next For Me. And I think that’s a good example where he’s doing things, bringing together people in certain communities to discuss these issues.
Joe: But institutionally it’s a challenge. Certainly, a lot of companies are trying to figure out what to do with it. They tend to be late, but it’s certainly a growing part of their workforce, the older segment. And so I think there’s an effort underway among the smarter companies to look at, how do we really leverage the talents and experiences of more mature workers? And in some industries the demand curve is changing a little bit, so that becomes more appealing to them, or being demanded. So a lot going on there. But a lot of the institutions that provided some of this support previously are less influential than they used to be. So there is a gap. There’s definitely a gap there. But it does, whether it’s individual or groups having a process, having ability to reflect, provide, get insights, but then translate them ultimately into some action that’s right for that person, I think is the best how to describe it.
Steve: Joe, have you seen any really successful groups or companies that have instituted programs that have been doing this in a successful way?
Joe: Not yet, because most are just getting into it. We have some companies that we talk with and work with on helping to provide workshops for their employees. These are companies that have invested in recent years in financial wellness education to get people better prepared retirement. Our workshop works on the life side, so to help them prepare for life after retirement, begin planning now if you’re five years out. If you’re three years out you can start to think about this for a different time horizon. So there is some interest in that because companies are now saying, okay we’re preparing people better financially, but there’s this whole other side that may take it to the next level.
Steve: So are you seeing then that people are starting to think about this three to five years in advance, then go to retire, and then they have like a six month engagement or something when they are really thinking about it deeply as they make that transition? I mean, what is this life cycle of transition, the transition life cycle look like?
Joe: Sure. So I’ll give you two data points on that, one from our client experience, and then just from some of the research that’s been done. So most of the people we’re working with are about one to two years out. We’ve had a couple come with the three- to five-year range, but that’s less common. When they’re one year up, there’s still a lot you can do. But you’re kind of going a little bit at double time because it’s right in front of them. One thing that is going on though is you’ve seen the surveys where many more people want to work longer. The Transamerica survey and the Employee Benefit industry survey have it about 70%. but there’s a gap because only about 30%, well less than 30%, actually report that they do work longer past 65. And a lot of that stems from the fact that people aren’t doing the preparation of what it takes to be relevant, to be able … and the skill, keep the skills sharp, and relevant enough to be able to work longer.
Joe: So for example, when we have had people work with us three to five years in advance and they want to keep working, not everyone does, they then can begin to put in place a series of steps to get them closer to be better positioned with their network, better positioned with different opportunities to be able to work on a consulting basis, work on a part-time basis. So it gives them extra time to do that. If they don’t want to work, it still provides that benefit to be able to think through, well, what is what’s next? What are some of the things? What are the takeaways from looking at my life to date, and looking ahead forward to what those next chapters might be, could be, and what are some of the challenges I’ll be facing? Because there’s a division side, which is very compelling. There’s the challenger side which you really have to get into a little bit too.
Steve: Yeah, I think it’s hard to say, oh, here’s what I’ll be doing 20 years from now. I mean, who knows, right? The world’s changing so fast anyway, your life changes. But being, like, actually taking the time to say, okay, I’m going to pause. Like what you’re doing. Like I’m going to force myself to think about this for a little while, not rush into things. I see so many people in my social network that are like, they’re onto the next thing, you know?
Steve: I got to make a quick decision. I have to take this job. You know? I was in a executive kind of mastermind group and this guy had a high-level thing, he left, and he was like, I just feel this super-strong compulsion. Like I don’t have to do this, but I feel like I have to work and get back to it, you know, so quickly. And I was telling him, I was like, I think there’s a lot of value in just trying to think about it for a second and really think about how you’re spending your time, versus, pick something. Because you’re going to have a very narrow set of choices if you limit your time to a very short timeframe.
Joe: Yeah, that’s interesting you said it, because there’s an academic who you may know on Twitter, Martin Hyde, and there’s a group that just did a study, came out last week, The Center for Aging Better, in the UK. And they studied workshops that are done there. And all the participants were in the healthcare industry. They talked about why these things were effective. And one of the biggest reasons was that the participants reported that they found it so valuable to have dedicated time to finally focus on and think about these things, because they’re in the back of our head sometimes. We have short conversations or we mean to focus on it, but just having dedicated time to think about it and what the deep introspection, deep reflection of that can really create the important insights. But just having dedicated focused time, like anything we’ve done in life and careers, it goes a long way.
Steve: Right. And just another side story, we had an advisory board meeting last week, and it’s just super useful as a business. And you think of the business as a, you know, there are parallels to being an individual. But like stepping back, okay, what are we doing? What’s most important? What’s going to, you know… Where should we really focus our time and energy? Because there’s a million things going on, there’s a million options you could pursue. But the preparation and then conducting that meeting, and then the postmortem or thinking about our conclusions was super helpful. And building that into your own life at regular intervals I think would be, it doesn’t have to be at retirement, it could be, you know, hey, 25 and 30 and whatever it is. You know? What do I want the next three to five years to look like?
Steve: Joseph, I’d love to get just a couple… I don’t know if you have any highlights and lowlights of like, hey, here’s been some huge success stories. Or hey, here’s some big things that have tripped people up.
Joe: Sure, I’ll share three of them. I have to be obviously concerned about confidentiality, so they’ll be a little more vague than I’d like to be, but that’s an important part of what I do. And ironically they fall into categories that many of our clients’ stories do cluster into. So I talked about the portfolio life one before, that’s probably the most common. People coming up with a variety of things that they would like to do. I like to call it either portfolio life, or there’s a better way to say it which is, a little bit of this and a little bit of that. We’ve also had several people choose to go back to school after demanding careers, and they’re often in their 50s. I had one person, early sixties who was a business owner. He actually went and create a business right out of high school.
Joe: So he never went to college, always bothered him. He was usually successful, and he sold the business. And before he sold the business he came to to us and said, I’m really actually afraid of this because I’ve put everything I have of myself into this business and it’s really who I am. What he ended up doing was to go back to school. We’ve had several people do, as I mentioned, not for career shift or any type of professional preparation, but just out of sheer interest. And I think one of the things that struck me about what he said is, I feel like I learned that I had some unfinished business just from a personal learning standpoint. So I thought that was an interesting one where he just, you know, he had the financial side nailed. He had done all the planning, he had a very successful sale and exit. But it was really about, now what am I going to do with my time? What am I going to invest in? And it surprised him, it wasn’t what he came to the table with, it came through that process of reflection and discovery.
Joe: Another example, and we’ve had a few people do this, and that’s the, going from a high powered corporate career to not for profit work. And this comes with both highlights and lowlights embedded. So I had one person who came out of, you know, very highly educated, MBA from a Tufts school, et cetera. Really in his mid-50s decided that he wanted to make a shift toward doing something with more meaning. Didn’t really know what that was exactly, but he ended up going back to, or make a big shift to work at a more mission-driven organization, something that was really personally important to him and his family. And he took a role there that allowed him to use his financial expertise in a way that really helped that organization quite a bit. The transition though is the low light and that meaning, when someone’s used to running something or working in a high paced environment like all of us have, all of a sudden you’re in the nonprofit world, which is going to operate at different speed. And you’re not going to be running anything for quite some time.
Joe: So that was an adjustment period, it was a little bumpy for him. But this is the person who I think is, and the others who have done this, that when you talk to them, they’re really happy with the choice they made. Definitely trade-offs, definitely a hard transition, but really good thing. And then I had the opposite one, and this isn’t as common, a matter of fact this is an outlier. And I call that one, I’d like one more go at it, but on my own terms. We had a senior person who, this was more of a forced, the decision was made for them. They had a restructuring of their company and had to move along. And he all of a sudden found this freedom, which he did the same introspection process in terms of, what does this mean for me from a life standpoint, even from a spiritual standpoint? And what do I really want to do?
Joe: And he was looking at a lot of opportunities. He looked at the nonprofit mission-driven one. He came back with an idea that he was very excited about. At one point I could buy this really cool cafe I saw in Seattle, that he had started to have discussions about. But he concluded after about a year of saying, you know what, I really want one more run at it. And he was young enough to do it, but he ended up going back and really doing a turnaround with a private equity company. Because he had decided that even though he thought he wanted to do something totally radically different and totally, you know, use his freedom. He wanted one more shot, one more shot at the merry-go-round.
Joe: But that’s not more common. That’s not common. The more common ones are looking to do something different and something more meaningful.
Steve: Well, and that could change too. They might try the nonprofit for three to five years and then be like, you know what, time to start my new company.
Joe: Absolutely. And we’re not trying to solve for 20 years, we’re trying to solve for the what’s next focus and that what I think people are finding most useful.
Steve: Okay. Awesome. Well Joe, thanks for sharing that. That was super helpful. All right, well look, I think with that, you know, we can wrap this up. Joe, you know, we heard your list of books, we’ll summarize it on the transcript and put links out and to your site. And I will say that for our business, we’re focused on kind of the financial side of it. But really where I see people light up is, what the heck am I going to do with my life? You know? Especially if they’ve got the money side relatively tied down it’s a lot easier. They do have to kind of, we start with money because it’s hard to think about other things if you’re hungry or whatever, if you have a core, a lower-level need.
Steve: But yeah, I feel like this is going to become a huge topic for so many people as more and more of the boomers, you know, and Gen Xers kind of reach this phase where they’re like, okay, looking forward, what’s next for my life?
Joe: And there are so many possibilities, but so many layers to this, and different people are different places. But so many possibilities and so many layers to go through.
Steve: Okay. So with that, I’ll wrap it up. So Joe, thanks for being on our show. Thanks, Davorin Robison for being our sound engineer. Anyone listening, thanks for listening, hopefully you found it useful. Our goal at Boldin is to help anyone plan and manage their retirements so they can make the most of their money and time. And if you’ve made it this far, one, please check out Retirement Wisdom, that’s Joe site. And obviously our site and our tools.
Steve: You can join our private Facebook group as well, where people ask questions, sometimes questions for this podcast come up and people share comments and feedback. And by the way, we’re starting to see more questions about kind of the life side of this, and that are that are coming out, which is great to see. And then also seeing a lot of support from one community member to the other. And then finally, we’re trying to build the audience for this podcast, so if you could leave us a review on iTunes or Stitcher or anywhere that’s appreciated. We read them all and use that as feedback into our show. So that’s it. So thanks again and I hope everyone has a great day.