The author and adventure sailor on thinking big, changing your life course, and managing the transition into retirement.
Our guest on the podcast today is author and retirement coach, Larry Jacobson. Larry is the author of a book called Your Ideal Retirement Workbook, A Step-by-Step Guide to Retiring With Purpose and Fulfillment, which coaches its readers on the steps to take to find purpose and identity in retirement. He embarked on a career as a retirement coach after stepping away from corporate life, and he sold his business in order to sail around the world.
Your Ideal Retirement Workbook: A Step-by-Step Guide to Retiring With Purpose and Fulfillment
YourIdealRetirementWorkbook.com
Retirement Coaches Association
Transitions, by William Bridges
(Please stay tuned for important disclosure information at the conclusion of this episode.)
Christine Benz: Hi and welcome to The Long View. I’m Christine Benz, director of personal finance and retirement planning for Morningstar.
Amy Arnott: And I’m Amy Arnott, portfolio strategist for Morningstar.
Benz: Our guest on the podcast today is author and retirement coach, Larry Jacobson. Larry is the author of a book called Your Ideal Retirement Workbook, A Step-by-Step Guide to Retiring With Purpose and Fulfillment, which coaches its readers on the steps to take to find purpose and identity in retirement. He embarked on a career as a retirement coach after stepping away from corporate life, and he sold his business in order to sail around the world.
Larry, welcome to The Long View.
Larry Jacobson: Wonderful to be here.
Benz: It’s great to have you here. So, we do want to talk about your book, which has been recommended to us as a very useful resource for retirement planning. But before that, I want to get into your background a little bit and talk about your career before you pivoted into becoming an author and a retirement coach, which you are today.
Jacobson: Right. Well, the two really don’t have anything to do with each other. But I was in the incentive travel industry, which is basically rewarding people at a company, the top salespeople, with an award that is a unique travel experience. So, like we would take 500 people from ABC Company on a trip to Switzerland and charter the Orient Express or something. And that was the ones who had achieved a certain level of sales. And in the 1980s and ‘90s, that was a multi, multi-billion-dollar industry. And I worked for a company for five years doing that. And then I left that company, started my own company and ran that company for the next 15 years. And we became kind of the darling of the industry. It was world-class incentives. And I ended up as CEO. And then in 1998, I sold the company and decided that that was enough and stayed on for three more years. And then I bought a boat and left.
Benz: So, I want to talk about that boat and the trip you took because one of your life goals was to sail around the world. And you eventually did that, even though there were naysayers in your orbit, it sounds like. So, what were you hoping to gain from that experience and did it deliver? It sounds like it did, based on what I read in the book.
Jacobson: Well, when I was 13 years old, I taught myself to sail. And a tiny little boat that was made out of Styrofoam down in Southern California. And after that, I thought, wow, this is great. And Robin Lee Graham, who had sailed around the world, started when he was 16. And I thought, well, if he can do it, why can’t I do it? So, I announced to my family and friends that I was going to sail around the world and got a few giggles. And then I just got more and more into sailing. And I had discovered that was my passion, and that was really lucky on my part, because a lot of people don’t know what their passion is.
Then life kind of got in the way. And I spent the next 33 years hanging on to that dream. And then I was able to make it happen by selling the company. And although actually when I sold the company, I earned enough money, just enough money to think that I could retire and take off and go sailing. But I did. And I think what I was looking for was not only to satisfy my dream of sailing around the world, which I told myself I was going to do. And it is kind of the ultimate in sailing, the Everest of sailing, if you will. And I was looking for happiness. And I was looking for love and adventure. And it did feel incredible to achieve that. It was a great, great feeling of self-esteem and boosted my confidence and that I achieved something so big and so grand, because it’s a very small club of those who have sailed around the world. But it didn’t quite come to the absolute fruition that I wanted it to, in the sense that it satisfied myself, but the delivery of what I was really looking for, which was self-actualization—like from Maslow’s hierarchy of needs—that didn’t happen until I got home and that I realized that it wasn’t really just about me. And the self-actualization came from helping other people.
Arnott: Yeah, I wanted to talk about that, because you write in the book that you realized that there was still more that you wanted to achieve, even though you had hit that really big goal of sailing around the world. So maybe you can talk about that, how you found direction and your next steps after that and made this pivot into the kind of work you do today.
Jacobson: I was lucky, again. I think that luck plays a little bit of a part here. When I got home from the sailing trip, it took six years. And when I got home, I was lost. I thought, oh my gosh, I don’t even know where I am here. I thought the world had changed so much. Well, it turns out the world hadn’t changed, but I had changed in the way I looked at things. Before I left, I was kind of a high-flying executive and was flying first class and driving an Audi. And when I got home, I just didn’t care about any of those things, because I had traveled the world and seen the happiest people in the world were the ones who had very, very little. And so, I decided, well, I’ve got to do something. So, I sat down to write my memoir, and I wrote the book The Boy Behind the Gate. And that was the story of the six-year sailing journey. And it won six literary awards and was very successful, still is successful, actually.
And then after that, I got on the speaking circuit, and I was invited to do two TED talks, so I did those. And I really decided I liked public speaking, so I continued doing that. And then that went on for a few years, and then I was lost again. It was like a square peg trying to fit in a round hole. And I was lucky because an old friend of mine called me. He was a CEO of a big company in San Francisco. And he said, “Hey, Larry, can you come in and help me out with something?” And I said, “Sure.” So I go into his office, and I said, “OK, what do you need help with, personnel or finance or what?” And he says, “No, I don’t need any of that help. I’m the CEO. I know how to run the company.” And I said, “Oh, OK, well, what do you need?” He says, “I want to know how you did it. I want to know how you got out, because I don’t see how to do it. I don’t understand how I can go from being CEO to doing something else.” And he wanted to paint. He wanted to be an artist. So, I thought, well, OK, I hadn’t really thought about it that much. I gave him a couple of ideas. And about a week later, I got a call from a friend of his who is a CEO. And the same thing happened. I went into his office, and I thought, well, maybe I’m on to something here.
And then I started researching retirements and realized that there still are 10,000 people a day retiring in the United States alone. And that’s from the boomer generation. That’s going to go on for another, I think, eight years or something like that. And all of these people, maybe wondering, well, what are they going to do? And so, I thought, well, I’ve got to figure this out. So, I took a year, a full year, and I stopped everything, and I reverse-engineered all that I went through in the process of going from CEO to sailing bum—the thoughts and the actions and everything. And then I came up with this course, Sail Into Retirement, which is an online interactive video course. And it’s all about the processes that I went through to go from one identity to another. And that’s the basis of the book as well. And, so I became one of the first nonfinancial retirement coaches in the country. I helped found the Retirement Coaches Association. And the rest is history, I guess.
Benz: Well, definitely. And I want to delve into sailing as a metaphor for this retirement journey, because in your book, you come back to sailing in various sailing terms. Why do you think that there is that connection when people set off on this journey? Why do you think that the sailing metaphor carries over so well?
Jacobson: Well, again, good luck on my part. It just happened. There are so many metaphors. If you don’t know where you’re going, you could end up anywhere. If you don’t adjust your sails to the changing wind, you’re going to end up where the wind blows you, not where you want to go. To get anywhere, you have to know where you’re going, what your course is, and you have to stick to the course. The sailboats stall when there’s no wind. They become becalms. There’s just so many things about staying on course, keeping your course. And just as an example, if you’re sailing from the West Coast of the United States or Mexico, say, across the Pacific Ocean to the Marquesas Islands, that’s 2,750 miles. And if you’re off by one degree, just one compass degree, you’ll miss your destination by 48 miles. So, the metaphors are just so easy to—it’s like, well change course if you don’t like what you’re doing. And when you drop your anchor, if you don’t like where you’re anchored, pick the anchor up and move to another place. So, I think it just makes it easier for people to understand.
Arnott: Right. Before we get into some of the specific advice that comes out in the book, I want to talk about this problem of people not planning the nonfinancial aspects of their retirement. It seems like there’s so many resources available for thinking about the math of whether your money will last and how to invest your money in retirement, much less on some of these nonfinancial matters and how you get purpose and identity in retirement. Can you talk us through why we tend to neglect the nonfinancial aspects of retirement or why people often do and focus just on the numbers and the finances?
Jacobson: Sure. Just look at advertising. Any billboards or television, it’s all advertisements about saving your money for retirement and having enough money for retirement. And do you have enough? It never asks, what are you going to do with your time all day? And it never asks, how will you find purpose or fulfillment? And so, we never really thought about it. We never really, we didn’t think we needed a plan because no one ever told us we needed a plan. Therefore, we didn’t know how to write one. We didn’t even know what a plan would look like.
And part of that also is that we’re entering into a phase of life that is new. The boomer generation is the first generation to have the luxury of additional years that we get to do something else. We get to do over. My parents and a lot of people’s parents, they worked hard and then they retired, golfed for a year and then died. And we work hard and then we can retire and then we’ve got 20 more years left. That’s an awful long time to golf and to hope that golf will provide that purpose and fulfillment.
And I know there’s some people out there going, what, golf, more than golf? You’re really nuts, Larry. But our lives are scripted from birth basically in the United States. We go from elementary school to junior high school to high school. Then from there we go to either college or the military or an academy or an apprenticeship. And then we go into our work life. And when that’s over, when our work life is over—it’s like on Broadway, I always say that if it’s not on the page, it’s not on the stage. So, when you turn the page in your life’s script for what happens when you retire, there’s nothing there. It’s blank. And so, we get to write our own script. I have clients who are CEOs and VPs, and they have written multiple business plans, but they’ve never taken the time to write their own plan for what they’re going to do. And a lot of that also I think is because people get so entrenched in their careers that that’s what they know. Like my CEO friends, it’s like, how do I just let go of all of this? And you can tell when someone is not let go of their career, their identity. If they’re retired and you ask them, tell me something about yourself. And they might say, well, I’m a retired teacher or I’m a retired cop or I’m a retired lawyer or whatever. Well, that means they’re still hanging on to their old career. They haven’t moved on to the next one yet.
Benz: Well, I wonder in some cases, is that the right answer that if someone has a career that they really enjoy, should they try to hang on to it a bit longer or do something that’s kind of adjacent to that so that they can really maintain that sense of identity that’s important to them?
Jacobson: If they like it, absolutely.
Benz: Yeah.
Jacobson: Absolutely. A lot of my clients are lawyers, and this is not against lawyers. I love lawyers. I have two brothers who are lawyers, but they are the toughest clients because they want to do something else. But it’s all they know. They’ve been working 12-hour-days, seven days a week for their entire life, and they don’t know what else to do. So, they’re continuing in their career because they don’t know what else they might want to do or should do. But if they’re loving it, great. But if they’re not quite loving it, I tell people to use your skills, use that experience and that wisdom to come up with something else. In other words, if you’re a lawyer for defending corporations, maybe this time you want to defend the little guy. Or maybe you want to do some pro bono work for a needy group or something and to use those same skills and passions and wisdom for a different cause.
Benz: Right. One of the things I liked about the book is that it has a lot of exercises. Many of them are kind of in the form of questions to take yourself through, things to ask yourself. So, when you are working with clients about envisioning their retirements, what are some of the key questions that they should be asking themselves as they think about the nonfinancial aspects of their retirement?
Jacobson: Well, in the book, I don’t know if you noticed it, but there’s a part called the passion quiz. And I think it’s 29 or 30 questions that it asks you, starting with what makes you leap out of bed in the morning without a cup of coffee? Or what did you dream of doing when you were a kid? What do you like to do? When was the last time you had fun? When was the last time you stayed up late at night because you just couldn’t put down whatever it was that you were doing? And these are all questions that are—when we’re in our careers, we’re thinking, I don’t have time for that. I don’t have time to think about that I wanted to be a fireman, and now I’m 65 years old, how can I be a fireman? Well, maybe you can’t, but maybe you can volunteer to work with the forestry department or something. So, a lot of these questions are very simple. And in the passion quiz, you might have noticed that I asked the same question, but in a couple of different ways, different wording. And the idea is to then go back through your answers and to see if there are any consistencies. Do you mention the same word twice?
Arnott: So, you mentioned this idea of maybe reconnecting with some things that we love to do as a child. Can you give an example of that? Have you had any clients who have done that who have reconnected with some passion that they had when they were young?
Jacobson: Well, I had one client who always wanted to be a pilot. But then he came to me when he was 68 years old—that was a little bit old to be a pilot. And so, he took up remote control flying of airplanes. And that satisfied that itch. Not that he gets to fly for real, but he was still very happy about doing that. So that’s just like one example. There’s one client who was an attorney and he was a big-shot attorney. And his name not only was on his office door, not only on the letterhead, his name was on the building. So, it was time for him to retire. He would call his office every day and say, “OK, do you need me for anything? You need me to call any of our old clients or what do you need?” And they would always tell him, “No, we’re fine. We don’t need you.” And he was just heartbroken. And he just didn’t know what he was going to do. So, we got him into doing pro bono work for a needy group. And he was very happy about doing that.
Benz: How do you disentangle the status that comes along with some of these professions and the actual sense of purpose and identity? Because I think sometimes, we can mix those things up in our mind, right? The things that really put us on our pedestal in our community may not really be the things that are giving us a sense of purpose.
Jacobson: Well, I use as an example of this when I was in the travel industry, we were doing a lot of business, a lot of group business. So, if I would go to a Hilton hotel or a Hyatt or one of these, I had a status card that allowed me to have lots of privileges. And after I had left the industry and I came back from sailing, I was checking into a hotel once and they said, “Oh, sorry, your room’s not ready.” And I said, “Do you know who I used to be?” It’s just that you have to just let it go. I was no longer the VIP in the hotel industry, and there was nothing I could do about that. I committed career suicide. It had been my choice. I was a regular customer and you kind of get through that, and then I was driving a Honda instead of an Audi and it was fine. It’s just a matter of letting go, I think.
Benz: I noticed in the book, you frequently told readers to not get too hemmed in when they’re kind of thinking about their vision for retirement. Don’t get too hemmed in by logic or logistics that you want them to think expansively as they start out on this process. Why is that, to not think about, well, can I afford this, can my health support this, whatever? Why should you not include those thoughts?
Jacobson: It’s a really good question. It’s because logistics just get in the way of dreams. So, if I had let logistics get in the way of my dream of sailing around the world, I never would have left for a variety of reasons. One is I did not have the knowledge to leave to go sailing around the world. But I thought, well, I’ll just learn along the way. And I took that risk. And logistics, you think, OK, what I’d like to do is I think I would like to move to Italy for a year and write a novel while living in Tuscany. Oh, wait a minute. Who would watch the dog? And so, the dog is going to prevent you from achieving your dream. So those are just a couple of little examples of where logistics, which is the left brain, get in the way. And they say, oh, wait, you can’t do that because … It’s kind of all through our lives, we’ve been told to get our ducks in order. And I’m telling people to just let the ducks sit wherever they want. And that’s OK. And for people who have been working their whole lives, it’s a big change. It’s a big switch to do that. But the logistics will get in the way. You’re headed out for a family picnic one day and you come out to the driveway and there’s a flat tire on your car. What do you do? Well, fix the darn tire and go anyway, even if you’re a little bit late. But some people might say, oh, we can’t go. So, it’s a matter of just not letting those things get in the way. And they really can bog us down a lot. As I said, I never would have left the dock, I think, if I had to let logistics get in the way.
Benz: So, think big and then assume you’ll go in and tie up some of those loose ends.
Jacobson: Yes. Like for me, I thought, well, I’ll learn. I never navigated a boat across an ocean before. I thought, well, I better start figuring it out. After we left the coast of Mexico, I mean, I had basics, but I needed a lot more knowledge in order to go. And even now, if you said, do I have the knowledge to sail around the world? No, not really, because there’s so many surprises that come up. And so, you just have to be prepared to deal with those things.
Arnott: Right. So, even if it’s important not to get too bogged down by logistics, you do have an action guide that people can use as a framework to turn their dreams into reality. And you note that they’ll likely be calling on some of the skills that they used in their working life to achieve this task. So, it sounds like it’s sort of like project management, but for your own life and retirement vision?
Jacobson: It is. It is. It is project management. And it’s a project that we’ve never taken on because—I mean, here’s my deep belief is that while we ask ourselves these questions, like all the questions that are in the action guide, we all ask ourselves these a lot, but we’ve failed to answer them. And if we don’t answer the questions, then we don’t have a plan. We don’t have a plan to go forward. For some people, they’re encore—I call it the encore, what you’re going to do next—it just shows up, like mine showed up for coaching. It just happened into my lap. But for others, it’s a really, truly a project, and it has to be worked through to get to the end goal and then also to define the steps that are needed to take to make this project happen. So, when I decided I was going to sail around the world, I sat down and I thought, OK, what do I need to do to make this happen? Well, I’m going to need a boat, and then I’m going to need crew, and then I’m going to need enough money to go and then, on and on and on. And then you start putting those things in place. And the idea with the plan is, well, what’s the first step that you take to make your plan happen?
Benz: So, in the book, you think it’s important to conduct what’s called a SWOT analysis, S-W-O-T, so that’s strengths, weaknesses, opportunities and threats …
Jacobson: Right.
Benz: …as you’re kind of thinking about your vision for your retirement, the big things that you might want to accomplish. Why do you think that’s such an important exercise?
Jacobson: It’s really important because it points out to you what you’ve got on your side and what you don’t have on your side. So, I did this for myself before going sailing. And I realized that I was looking for strengths, weaknesses, opportunities and threats. So, my strengths were: I was good with people. I was organized. I was good at leadership. And I was a good problem-solver. But my weakness was I did not have the experience. An opportunity was, well, I can learn along the way, and I have other people I can talk to and ask about this. And the threats, well, in my case, the threats were fairly obvious. There’s about a thousand ways to die out there. But this is a tool that is used commonly in business. And businesses use it to analyze not only themselves, but their competition. And when you put those next to each other, you see, well, here’s our company and here’s their company. Gee, look at, we’ve got an opportunity here and they don’t. Or they have a bigger strength in this area than we do. And so, what I’ve done is just adapted that to personal. And I think once you know—it’s like, I’d like to build a custom house on some land that I own, but I don’t know anything about building houses and I’m not an engineer. I’m not an architect. Oh, wait a minute. I think my cousin is an architect. So that’s the opportunity. So, what it does is it allows you to look for answers where you need them.
Arnott: You also make the point that sometimes life being too good can kind of deter people from pursuing their dreams. And there was actually one thing from the book that I wrote down: “The good things in our life are what get in the way of great things.”
Jacobson: Yes.
Arnott: How common is that kind of complacency and how do you convince people that even if they’re relatively content in their life as it is, that it’s still worth trying to pursue something bigger?
Jacobson: Well, it is not necessarily bigger. Dreams don’t all have to be sailing around the world. But the number one obstacle to achieving our greatest achievements in life, I truly believe, is the good things we already have in our lives. And that is you have to have a pretty powerful motivator to motivate you to leave your comfort zone. And that’s basically what I’m talking about is leaving your comfort zone. And why would you want to do that? Well, you might have a powerful motivator. So, your dream might be to, I want to attend all of my grandkids’ soccer games every Saturday for the next year. Well, that might be difficult to do, but I’m going to make that happen by canceling everything else on Saturdays and trying to make that happen.
When I left to go sailing, I left everything behind. I left my career, which I spent 20 years building and I left my income, which went from pretty good to zero in a day, and I left my security, which—when I say security, I mean, that’s everything from having a car in your driveway to the local grocer knowing your name. I left my home, not only my physical home, but my friends and family. I didn’t know when or if I was going to see anybody ever again. And I also left my identity, who I was as a CEO and executive in the Silicon Valley. So, the motivator was big, because I really wanted to sail all the way around the world. And that’s what I was willing to risk, willing to give up. Now, are a lot of people affected by the comfort zone? Absolutely. I would say the majority of people are happy in their comfort zone. Everything is just fine. But again, it got right back to, well, do you have purpose and fulfillment?
Benz: So, I felt like a lot of the book got me thinking about doing really big things in retirement. But what about people who maybe do have somewhat more modest goals? So, you reference the idea of making every soccer game for your grandkids or something like that. Do you think that thinking big can be kind of stymieing for some people, that they think they need to climb Everest or sail around the world in order for their retirement to be a success? Can you make it a little smaller scale and still be happy?
Jacobson: Absolutely, you can make it smaller scale. Whatever your dream, whether it’s to sail around the world or open a corner coffee shop, that dream is just as valid as mine was of sailing around the world. And it’s more valid because it’s yours, it’s not the other person’s. I say, think big, because we’re always told, or we’ve been told that through our lives don’t be a daydreamer, be practical. And I want to encourage people to not think like that. If there’s a remote idea of moving to Italy to write the book in Tuscany, I want people to think that, hey, they can do that. They really can do that. And so, don’t think small. But if your dreams are to open a little corner coffee shop or to go to your grandkids’ soccer games or be their coach or something, that is a perfectly valid dream as long as something that you’re doing is giving you long-lasting purpose and fulfillment. We forget that at work, we have purpose and fulfillment. We have the idea and the feeling that we’re part of something larger than ourselves. And that’s what I want people to strive for in their retirement.
Arnott: Do you ever run into people who aren’t really sure what they want to do in retirement and is there any value in taking more of an experimental approach where you might try a few different things to see what you like?
Jacobson: Absolutely. Most people don’t know what they want to do, and that’s a big reason why clients come to me is, they’re going to say, I’m ready to retire, or usually clients come to me about a year after they’ve retired. And then they’re like, “Geez, I thought there’d be more, I thought it’d be more fun. I thought there’d be more to it. But I’m ending up just fixing the dishwasher and mowing the lawn.” And it’s easy to take up your time in retirement doing things like that. But just the idea of your transition to finding something that you want to do requires experimentation for a lot of people.
So, I subscribed to the philosophy of William Bridges, a great guy who wrote a book called Transitions. And he basically says that transitions come in three stages. And the first stage of a transition is an end. It’s the end of something. It’s not the beginning. It’s the end. So, you graduate, or you get married or divorced or a move or someone dies or something like that. That’s the end. And that’s what begins the transition. And then the middle stage is the exploration of new things and things that you maybe aren’t sure what you want to do. I think, again, I was lucky in that I knew that I wanted to go sailing, but most people don’t have that.
And then after you’ve experimented around for a lot of different things comes the last stage, which is the new beginning. And that’s when Julie Andrews comes running over the hillside singing the hills are alive and everything is beautiful, and the birds are chirping, and the grass is green and everything. But it’s important to remember though that each of these stages is not a parking lot. What I caution people about is that you get into stage two and experimentation and it’s great. It’s funny. Try tennis. You don’t like tennis. You try pickleball. You don’t like that. Then you try traveling to castles in Europe. OK, that was fun. Now let’s try something else. But we’re still looking for that purpose and fulfillment. That’s something that makes you feel part of something larger than yourself.
Arnott: And in thinking about those three phases, it seems like in the first stage where something is ending, I’m imagining people might get stuck at that stage, if they’re sad about the end of a career or kids leaving the house or things like that.
Jacobson: You are exactly right. They do get stuck there and that’s why I try to urge people into the second stage as quickly as possible. But I do caution people saying this is not a parking lot. You’re not staying here forever. So, choose something. Do it. If you don’t like it, that’s OK. Fear plays a big role in retirement. And one of the fears that people have is that they’ll choose the wrong thing, that they’ll go down the wrong road, that they might not like what they’ve chosen. Well, that’s OK. You can stop and you can do something else. And you do it until you find something that you do like or where you do get that feeling of purpose and fulfillment that you’re part of something larger than yourself.
Benz: I wanted to ask about older adults, so people retiring at kind of traditional retirement age, 65 or whatever. Do you coach them on really hitting their goals? Say they have big audacious goals that maybe require some physical activity. Do you urge them to really try to hit those things early because we know that health doesn’t always play out as we might hope? How does being realistic about how aging might affect our ability to do various things affect how you coach people?
Jacobson: It definitely affects it. Again, I was lucky. I left to go sailing when I was 46 and I was in good physical shape. But if you asked me if I wanted to go sailing now, I would say to you, I don’t have the strength. I couldn’t do it, I don’t think. It would be harder. It would be more taxing. I just don’t know if I could actually even do it, crawling around the boat and crawling down into the engine room and all these things. So, I definitely encourage people to start their bucket list, if you will, as early as possible. And you don’t have to wait for retirement. You can just start doing things even while you’re working, knocking things off of your list and having fun.
A lot of people come to me and ask me to help them get their boats ready in order to go sailing. And I have one friend who has been asking me for years, and I was helping him get ready. And then something physically happened to him, and he couldn’t go. So, he had to wait another year. And then when he finally did go, he realized that he wasn’t the young guy that he had thought he was. And so, he instead of sailing across the Pacific, he has sailed down to Mexico because it’s a bit easier. And so, you do have to adjust.
One of the things I always wanted to do was to kayak down—I forget the name of the river—but some river that’s on the border of Uzbekistan and somewhere up there. And that’s never going to happen. Yeah, it’s never going to happen because I no longer have the strength to do that. So, I have to face reality. You’ve got to face the music and also then adjust.
So, for example, I had one client who wanted to go on cruise ships, not just a cruise ship in the Caribbean, but he wanted to cross oceans like on the QE2 or something. His spouse got seasick just as the thought of it, just at a mention of it. And so, the compromise that they made was they went to Europe, and they did river cruises because she wouldn’t get seasick and then he still got to be on the boat. So, we do definitely have to adjust. And as hard as it is to face getting older, there’s not much we can do about it except just embrace it and veer off a little bit to do something different.
Arnott: How important is it to focus on a single passion? Is it possible or even helpful to have more than one? If your passion is skiing, but suddenly you have a knee injury, maybe you would move on to something different like pursuing a dream of writing a novel?
Jacobson: Absolutely. When I left to go sailing, I was focused on one thing, one thing only, and that my single passion was to get my boat around the world. And I think that requires that focus to get a boat around the world because it’s so challenging. It’s so difficult. But looking back, I think unless you were really into sailing and navigation and fixing boats, I must have been a pretty boring person to hang out with because that’s all I was interested in. And now that I have more passions of writing and speaking and sailing, sure, I think I’m better off for it. And I think you would be, as my friend, better off for it as well, as that I’m more interesting of a person with multiple interests. Again, I just make sure that one of those interests, whatever it is, is giving you that fulfillment that you want and not just pleasure.
And so, I might just take a moment to give an example of the difference between pleasure and fulfillment. So, I’m a sailor, so if I take my boat out, like you and I go out sailing for a day, and we’re coming back in toward the dock, and I dock the boat perfectly. And that’s satisfying for me. It feels good. But if I come back in and I teach you how to dock the boat and you dock the boat perfectly, that’s fulfillment for me.
Benz: Well, it seems like, Larry, what you’re talking about there is human connection and making a difference to another person and how they’re operating. Can you talk about that, the importance of relationships and human connections in all of this?
Jacobson: Absolutely. I think it’s critical. I think that socialization, connections, family, friends is the thing that will keep us alive the longest. For me, as I said, I didn’t discover until I got back from my sailing trip that the ultimate satisfaction in life was seeing other people make their dreams come true and helping them to achieve what they want to achieve. And I can do that because I now have the skills and the wisdom to be able to do that. I only coach on what I know. Sometimes, like, I’ll look at coaches and see someone who’s 30 years old and they become a retirement coach. Well, I’m sorry, but I just don’t see the credibility. It’s like, I’ve gone through it, I’ve done it, and I’ve created—my coaching program is based on experience, not only mine, but now my clients’ experiences as well. And there’s just nothing that feels better than being with a client and seeing them go, oh, I get it. And the light bulb goes on, and it’s like, oh, that makes me feel really good. It’s like when you’re getting a present. It’s much more fun to give a present and to watch the reaction of who you’re giving it to than it is to receive a present. So, I think it’s critical. I think the people connection is really important.
Arnott: You mentioned William Bridges and his work on life transitions. And I’m curious, are there any other thinkers or books that you’ve read related to retirement that you thought were particularly helpful?
Jacobson: Let me think about that. For sure, William Bridges, his work affected me. When I created my program, Sail into Retirement, one of the things that surprised me, I was pleasantly surprised, was I created the program and then after that, I started doing research on retirement. And that’s when I found people like William Bridges. And it was confirmed to me that I was on the right track that what I was saying was correct because that’s what other authors had said as well. I talk about Maslow, Maslow’s hierarchy of needs. And I think that he influenced me a lot. And yeah, Bridges, that’s it for now, I would say.
Benz: What do you think we get wrong about retirement planning in the US apart from focusing too much on the money? And it sounds like you think too many people show up in retirement too burned out to really think much beyond leisure. But what else do we get wrong?
Jacobson: We think that retirement is the end. We think that retirement is quitting, is stopping. I think it’s the opposite. I think that it’s our chance at a do-over and it’s our chance to relive our lives but this time directed by us with exactly what it is that we want to do. Now, I understand that not everybody has the means to do that, to do what they want to do. Some people even have to continue working. I continue working because I like it. I get great satisfaction and fulfillment from helping other people. But other people may have to continue working for income. But for those who can retire and just don’t look at it as quitting, it’s not stopping. It’s a do-over. It’s starting over again. You get to do whatever it is you want to do. And I think that’s the difference. I think that’s the challenge for us in America.
Arnott: What’s your take on the whole financial independence, retire early movement, people who might want to save aggressively so that they can retire at a much younger age?
Jacobson: Well, I think these people think that when they retire, they stop. And they just want to go and retire somewhere and live somewhere and play golf or go skiing or whatever it is that their favorite thing is to do. And I think that there’s a lot missing there, which is they’re not going to see the fulfillment and purpose of their lives. And I think they’re going to be disappointed.
Benz: I’m curious what’s left on your must-do list for retirement? It seems like you’ve ticked a lot of boxes, and you’re not really retired. But what are the things that when you think of what you want to accomplish in your lifetime, what’s left there?
Jacobson: Oh boy. The thing is, I’ve traveled a lot of places, so I don’t care to travel anymore. I’ve been rich, and I’ve been poor. I’ve done just about everything I’ve ever set out to do in my life. And so, what I’m enjoying now is writing. And so, I have a new book coming out next week, and I think I have three more books in the works, and I’m loving that. My challenge is that I sit down at my desk, and I stay there, and I need to get up more. So, I have this software that tells me when to stand and when to drink water and all those things. But I think that writing and speaking are big interests of mine. And in addition, while I think I’m a good public speaker. I’m a better public speaking coach. And so that’s one of the things that I do is I coach other speakers and basically again, it’s the same theme. It’s helping other people make their dreams come true. So, I think that’s what I’ll continue doing until they end.
Benz: I’m curious, Larry, while we have you here, if you had to give one or two bits of advice to people who do public speaking, what would you say?
Jacobson: Video yourself when you practice. That would be the main thing. Don’t just practice into a tape recorder or audio, but video yourself as well, so you can see all your actions and your movements and your behaviors on stage. I would say be overly prepared. When I did my first Ted talk, I had a goal. I practiced it. I went through it a hundred times. I was doing it in the bathtub, and I was doing it while I’m cooking. And I could almost have said that speech backward. And that helps a lot is to be prepared. Most people who are nervous on stage are nervous because they don’t know the material enough. Have that confidence and the confidence comes from you know that material cold. Those are a couple of things.
Benz: So, practice makes perfect.
Jacobson: Yeah, yeah. On one of my websites, there’s a free document that people can get with 11 tips to better public speaking. It’s on the website ownthestage.org.
Benz: Wonderful. We’ll include it in the show notes.
Jacobson: Good.
Benz: Larry, it has been a real treat to talk to you, to hear your inspiring story. Thank you so much for taking time to be with us today.
Jacobson: This is a lot of fun. Let’s go another hour. Thank you so much.
Arnott: I’m sure we could.
Jacobson: Yeah, absolutely. And if you want to do it again, I’m happy to. There’s so much to expand into. And also, people should be able to look out that the book is going to be republished with a new edition and it’s going to be called What’s Your Encore?
Benz: Wonderful. Well, thank you so much, Larry.
Jacobson: Thank you.
Arnott: Thanks, Larry.
Benz: Thank you for joining us on The Long View. If you could, please take a moment to subscribe to and rate the podcast on Apple, Spotify, or wherever you get your podcasts.
You can follow me on social media at @Christine_Benz on X or Christine Benz on LinkedIn.
Arnott: And at Amy Arnott on LinkedIn.
Benz: George Castady is our engineer for the podcast and Kari Greczek produces the show notes each week.
Finally, we’d love to get your feedback. If you have a comment or a guest idea, please email us at TheLongView@Morningstar.com. Until next time, thanks for joining us.
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