Decision Vision

Decision Vision Episode 69: How Should I Choose a Second Act Career? - An Interview with Jim Deupree, ChapterTwo®

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Decision Vision Episode 69: How Should I Choose a Second Act Career? – An Interview with Jim Deupree, ChapterTwo®

What’s involved in a career pivot? How do I distinguish a mid-life crisis from the legitimate need to pursue a second act? Jim Deupree of ChapterTwo® joins “Decision Vision” to discuss these questions and much more with host Mike Blake. “Decision Vision” is presented by Brady Ware & Company.

Jim Deupree, ChapterTwo®

Jim Deupree is the Founder and CEO of ChapterTwo^®.

Jim began his career as an automotive engineer, then pivoted to IBM when he discovered the role and power of computers. Two years in, he asked IBM to switch his career from development to sales, and three years later he was at IBM HQ. Soon he did something he now realizes was pretty unique:  he decided that he would only accept roles he knew he would enjoy. So he turned down promotions at numerous stages until roles he wanted became available, and it served him well. He truly enjoyed his entire career there, and it led him to a diversity of experiences most of his peers did not achieve.

His IBM career featured a number of intrepreneurial leadership roles and concluded voluntarily when he wanted to gain experience with smaller companies and after authoring two strategy books for banks. First he became SVP of a local management consulting firm, then an entrepreneur. He founded a company with a new business model, taking it through all of the steps including raising equity under SEC regulations. Launching a second company followed. While running that company he volunteered to help C-Suite executives in transition sort out defining and getting their next role – as part of a major outplacement company with a center dedicated to CXO executives. After 18 months they asked him to stop his other activities and run the Center.

Beginning in his twenties he have served on non-profit boards helping the community every place he has lived, ranging from the arts to homeless to protecting homeowner rights to leadership and governance. He has also served on five for-profit boards, and been active in the National Association of Corporate Directors, where I served as President of the Atlanta Chapter and as a Founding Director of the Carolinas Chapter. Current roles include the local and national boards of CEO Netweavers and Board Chair – Strategic Leadership Forum, Carolinas.

Six years ago, Jim founded ChapterTwo as his third start-up, based on realizing the shortcomings of the outplacement model for senior executives and their advice about how much they would have valued charting their career before ending up in transition.

For more information on ChapterTwo, go to their website.

Michael Blake, Brady Ware & Company

Michael Blake is Host of the “Decision Vision” podcast series and a Director of Brady Ware & Company. Mike specializes in the valuation of intellectual property-driven firms, such as software firms, aerospace firms and professional services firms, most frequently in the capacity as a transaction advisor, helping clients obtain great outcomes from complex transaction opportunities. He is also a specialist in the appraisal of intellectual properties as stand-alone assets, such as software, trade secrets, and patents.

Mike has been a full-time business appraiser for 13 years with public accounting firms, boutique business appraisal firms, and an owner of his own firm. Prior to that, he spent 8 years in venture capital and investment banking, including transactions in the U.S., Israel, Russia, Ukraine, and Belarus.

Brady Ware & Company

Brady Ware & Company is a regional full-service accounting and advisory firm which helps businesses and entrepreneurs make visions a reality. Brady Ware services clients nationally from its offices in Alpharetta, GA; Columbus and Dayton, OH; and Richmond, IN. The firm is growth minded, committed to the regions in which they operate, and most importantly, they make significant investments in their people and service offerings to meet the changing financial needs of those they are privileged to serve. The firm is dedicated to providing results that make a difference for its clients.

Decision Vision Podcast Series

“Decision Vision” is a podcast covering topics and issues facing small business owners and connecting them with solutions from leading experts. This series is presented by Brady Ware & Company. If you are a decision maker for a small business, we’d love to hear from you. Contact us at decisionvision@bradyware.com and make sure to listen to every Thursday to the “Decision Vision” podcast. Past episodes of “Decision Vision” can be found here. “Decision Vision” is produced and broadcast by the North Fulton studio of Business RadioX®.

Visit Brady Ware & Company on social media:

LinkedIn:  https://www.linkedin.com/company/brady-ware/

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Show Transcript

Intro: Welcome to Decision Vision, a podcast series focusing on critical business decisions. Brought to you by Brady Ware & Company. Brady Ware is a regional service accounting advisory that helps businesses and entrepreneurs make vision a reality.

Mike Blake: And welcome to Decision Vision, a podcast giving you, the listener, clear vision to make great decisions. In each episode, we discuss the process of decision making on a different topic from the business owner’s or executive’s respective. We aren’t necessarily telling you what to do, but we can put you in a position to make an informed decision on your own and understand when you might need help along the way.

Mike Blake: My name is Mike Blake, and I’m your host for today’s program. I’m a Director at Brady Ware & Company, a full service accounting firm based in Dayton, Ohio, with offices in Dayton; Columbus, Ohio; Richmond, Indiana, and Alpharetta, Georgia. Brady Ware is sponsoring this podcast, which is being recorded in Atlanta, per social distancing protocols. If you like this podcast, please subscribe and your favorite podcast aggregator, and please consider leaving a review of the podcast as well.

Mike Blake: So, today, we’re going to discuss, should I be thinking about my second act? And I think about this question a lot, maybe more often than I have been. Last Saturday, I’m recording this on May 8th, but last Saturday, I had the audacity to record my 50th trip around the sun. And so, I’m sort of in second act thinking territory as well, perhaps, because I planned to live for a very, very, very long time. I’m sort of greedy that way.

Mike Blake: But I’m also heavily involved in business transitions, whether it’s somebody who’s selling a business, or somebody is buying a business as their so-called second act, or whether it’s a succession planning. And we’ve had discussions about most or all of those topics. We’ve had a discussion on succession planning and how you hand the business after the next generation. We’ve had a discussion on how you go about selling your business, and how you figure out the timing, and what are some of the mechanics in doing that.

Mike Blake: But before you get to any of those phases, the business owner or the executive has to reach a point where they decide that some kind of change is desirable and necessary. And the funny thing about this is 10, 12, 15 years ago, we just knew that everybody by now, maybe before now, was going to have to sell their businesses. They’re just going to be too damn old. They weren’t going to want to be in the businesses anymore. They’re going to want to play golf, spend time with their grandchildren, do anything other than businesses. So, people like me, we were rubbing our hands and licking our chops because we thought they’re just a bunch of businesses that we’re going gonna come on the market.

Mike Blake: And then, a funny thing happened. A lot of people decided to hang on to their businesses, started to hang on to their careers. And I think there are a lot of reasons for that. One, I think that the ’08-’09 recession raised enough wealth and, frankly, just put the fear of God into enough people that they decided they’re going to hang around and generate some more value, some more income for a few years before they move on to that second thing or even entertain the risk of moving on to something different, even if that was going to be income producing.

Mike Blake: And also, what we’ve figured out – and, again, haven’t just turned 50. I appreciate this more than I ever did – is that 65 ain’t all that old anymore, especially if you’ve not been working a manual labor job. If you’ve taken care of yourself and if you’re blessed with reasonably good genes, you can be viable and vibrant well into your 70s. And there are business owners who would hang onto their business even into their 80s. And so, this demographic brick wall that we thought was going to happen really has not. Sure, there’s been an uptick in sales and transfers but has not been this rush to the door of millions of people feeling like they had to sell their businesses because there was a countdown that was going on.

Mike Blake: Well, here we are, a decade after the Great Recession, and we now find ourselves in the COVID whatever the heck this thing is. I don’t know. I speak eight languages. I don’t know a word in any of them that properly describes this. But at any rate, we’re in this thing. And I think this is now prompting people to think more about that second that. We’re seeing such dislocation. My own personal view is that we are not going to go back to what the world was like in February. I think that’s gone. I think people are increasingly realizing that, and they’re expressing various stages of grief in doing so. And that means a certain jobs are going away, certain industries are going away, certain needs are going away. And in their wake, jobs, industries, and needs are being created, and they’re being defined in real time.

Mike Blake: And if there’s ever a time when thinking about your second act because maybe that job is going away, maybe that company is going away, or maybe you just sort of see the writing on the wall, maybe it’s not going away today but you see in 10 years, it’s just not going to be the same thing, and it’s just not going to be as rewarding for you to do it anymore. You may be thinking about about some sort of second act or second career, as it’s often referred to.

Mike Blake: And as it happens, in my network, I know one of the best in the business at helping people figure out this the second act thesis. I have friends who have worked with him and have gone through the program. I’ve been honored to have, at times, been a mentor in the program, which is really interesting because at the time, I was half the age of a lot of the people that he was serving. But he’s really the expert on this. And we’re gonna have a great conversation with my friend Jim Deupree, who is founder of ChapterTwo.

Mike Blake: He founded ChapterTwo 12 years ago to help senior executives proactively set their compass for a career path going forward that is both significant and satisfying. All of his clients are selected in part for commitment to the pay-it-forward approach. And that’s really important. His clientele is somebody that is is not just sort of, “I got mine,” but it’s somebody that is, “I got to give back.” And Jim, he just brings this breadth of experience. You look at his resume, it’s like he’s lived three lifetimes. He’s been an entrepreneur, has raised millions of dollars of capital. He’s been an angel investor, which I did not know. So, a lot to talk about that at some point offline.

Mike Blake: He’s been a blue chip company executive holding executive positions in companies you may have heard of, such as IBM, Ford Motor Company, Coca-Cola Company, and across a range of industries and functions, including manufacturing, financial services, consulting and so forth. He served as President of the Atlanta chapter of the National Association of Corporate Directors, which is a very exclusive group, and was a founding board member of the New Carolina Chapter, and he was recognized as a board.

Mike Blake: And this is where I know Jim primarily, he co-founded and served as president of an organization called CEO Net Weavers and continues to serve on their operating committee. And CEO Net Weavers, I can’t believe they let me in, but it is a fantastic organization where it’s a group of service-minded current and former executives who want to take their knowledge, their networks, and give back to the next generation of professionals, business owners, entrepreneurs to help them be successful and help position them to turn around and give back to the next generation that is coming back behind them.

Mike Blake: He’s adjunct faculty at Kennesaw State University, which is a a fantastic school on the outskirts of Atlanta and teaches their executive MBA classes. And I did not know this last point, which was he is the author of two strategy books for banks regarding effective use of the internet. And I actually do bank valuation on occasion. So, I need to read those books. So, I’m going to ask him for autograph copies. But, Jim, thanks so much for coming on the program.

Jim Deupree: You’re welcome. It’s a delight to be here. And I’m a big fan of Mike Blake for all he does to help people too, by the way.

Mike Blake: So, thank you for that. So, let’s jump into it. A lot of people know what a second act is, may understand instinctively what a chapter two is, but not everybody does. So, in your mind, what is it and why do people need help figuring it out?

Jim Deupree: Okay. Well, to me, it’s a pivot. So, going up to the next level in an organization, moving from director to vice president or whatever it is, is not a second act, or moving to another position, similar or maybe higher position in the same industry. The second act is really deciding that for whatever reason, I want to move on from what I’ve been doing and go to something that’s substantially different industry, major different kind of a role. Maybe it’s leaving corporate America, buying a business, becoming an entrepreneur, or moving from an operating role in a consulting or moving to join the board of directors.

Mike Blake: So, what are some signs that act one either is ending or should be ended? How do you know or what should start your thinking that maybe that’s the kind of transition you need to really start thinking about?

Jim Deupree: I think it’s a couple of things, Mike. 70% of people in corporate America say that they are not fully engaged in their job. That’s a stunning number; yet, it’s been repeated in many different surveys. And a third of those are meaningfully disengaged. So, to them, either they don’t like their leaders, and they’re turned off by their leaders, or the role has become mechanical or rote. It’s, “I can do it in my sleep. It’s not inspiring. I’m not really building anything. I’m just maintaining status quo.” So, when that happens, it’s not fun. You don’t skip into the building to go to work. You just kind of drag yourself in.

Jim Deupree: The other one is industries are changing, as you mentioned, in your opening. I mean, a lot is going on, and every industry is changing in many ways. But sometimes, the industry is not as appealing as it was when you started. Or, sometimes, the mission is not as appealing. So, those two things are really the keys. And I call it the voice in your head. The people I work with will admit that they had a voice in their head a year or two before they really acted on that voice that was telling them it’s time to start thinking differently.

Mike Blake: So, there’s a question I want to sneak in here and sort of go off the script because I think it’s important. When I think about second act, I tend to vision somebody that looks like me or maybe is a little bit older than I am, somebody that’s had a longish chapter one. And then, they’re ready to sort of cast aside. But then, it occurred to me that that may not necessarily be true. In fact, I know for a fact that one of your clients is a dear friend of mine is about five years younger than I am. And I know somebody who I think effectively did a chapter two right out of college or right out of, as it turned out, law school. You can have a chapter two pretty early, can’t you?

Jim Deupree: You sure can. It’s interesting. So, the biggest single group by age group of our clients are people in their 50s. And they are generally saying, “I really want to lay the pathway to say that I can continue to be relevant and enjoy the things I’m doing. Not necessarily trying to reach higher levels at that point, but I just want to make sure that this plays out in a way that’s enjoyable to me and to the degree possible that I have control over how long I do it, how long I’m in this role versus I find myself being ejected or as the British say, made redundant.”

Jim Deupree: The 40s are saying, “I really want to decide if I want to go for the brass ring. The tremendous sacrifices that are required to go for the top jobs. And so, I want an independent view of what my probability of success is based on getting to know me really well, and then that journey looks like versus not going for the top rating, maybe giving up some calm, but having a better balance of life.”

Jim Deupree: And people I work with in their 30s are saying, “What I’d really like to do is define this, so that I can have a time with my family now, and then I can accelerate my career in five years. So, how do I lay that out?”

Jim Deupree: And you mentioned the ones out of college, Mike. And it’s interesting because in my mind, everybody who go into a top tier MBA school should go through a process like this because, in general, they either leave to go to investment banking, or consulting, or in rare occasion, to some corporation. They don’t fully understand the hundred-hour weeks that those things involve and the travel. And they haven’t thought through what they would like to be doing in 10 years. So, if they did think through and say, “Well, I may want to still do that at the start because it’s a great foundation, but in 10 years, I want to own my own business, or in eight years, I want to own my own business.” They would probably develop a different network even in MBA school, and they would probably take some different courses.

Jim Deupree: So, in the last group are the people in their 60s, and they’re really saying, “I want to lay this out in a way that says that I’m shifting from the title, and then I come to things that are more significant to me personally and to my family.”

Mike Blake: Yeah. And sort of a corollary to that too, I think … well, let me ask you this. I suspect that one of the psychological hurdles that you have to overcome is the notion of sunk cost, right? I suspect that one area of resistance to taking on the second chapter is while I have a lot invested in chapter one, how do I just sort of let that go? Now, the accountant training in me, I’m not an accountant, but the accountant training and he says, while rationally, I ought to think of that as a sunk cost.

Mike Blake: And I have a friend, I mentioned, who did an early chapter two. He actually happened with my RA in college. And now, we’re back together here in Atlanta. He went to law school, worked in law school for a year, and then decided that he hated it and went into technology, right? And that was kind of tough. But the same time, he’d already spent that money. So, it wasn’t like he was going to get it back necessarily by going back and being a miserable attorney. Does that ever enter into the mindset of some of your clients? And if so, how do you kind of break that down?

Jim Deupree: It really doesn’t. I mean, personally, I’m a big believer in, “We are where we are. Now, how do we move ahead.” And people, what they’re looking for is more significance and more satisfaction. And if they weren’t getting it, then you got to walk away from that cause. I mean, one of the questions, I think, Mike, is, there a need for a second-act period? And I looked at a couple of numbers. So, 50% of college students changed their major during college. And whatever they thought they were going to do, then they go change it. Maybe a funny analogy, but the divorce rate, the odds of staying married to the same person are probably 40%. And as you pointed out, we’re all going to work for 50 years or more in today’s world. So, it would be very natural to say, “I don’t want to spend 50 years of my life doing the same thing, particularly if it’s not making me happy.”

Mike Blake: Now, let me take the flip side. Are there signs where … and it sounds like it is a rarity, but the natural question is for some people, maybe one act actually isn’t enough, right? Are there signs where maybe your state … let me ask the question differently. How do we distinguish the need for a second act from a garden variety mid-life crisis?

Jim Deupree: That’s a good question. So, to me, there are two reasons why you don’t need a second act. The first is you’re just really enjoying what you’re doing. Yeah. So, if you’re really enjoying it, then why go to something else? And the second is you’re building a business for your family, you’re building a legacy, and you feel really good about that, and you feel good, and it’s relevant, and it’s substantial to you. So, if those two things are present, then there’s no reason to think about a second act. A third thing that keeps people thinking about one is being risk averse. That’s not the right reason, but it certainly happens a lot.

Mike Blake: And in fact, I imagine, perversely, the riskier thing is staying in the thing that you don’t find fulfilling.

Jim Deupree: Correct. And it’s riskier for your health, as well as your finances.

Mike Blake: So, you deal with people that are considering and implementing the second act that come from a variety of backgrounds, that are entrepreneurs, business owners, family business owners, executives in large companies, small companies. Are there common threads to all of them, or does the background of the individual tend to shape what the trajectory of the second act looks like, or do people just sort of come to you and help them and say, “Hey, here’s my life. It’s a whiteboard,” and then you’re going to help erase it, so they get a fresh mental start?

Jim Deupree: It’s more the latter. I mean, what’s common across all of those is people, in their own minds, people that would appear enormously successful on their resume do not necessarily share that personal view. And even more frequently is it’s been great to be the CEO of a company that makes catalytic mufflers, but that’s not exactly the legacy that I’d like to leave. I’d like to take my resources and my talent and do something before I step down that I feel is really good for poor people and for humanity, and not necessarily for free. There are a lot of ways to contribute, but I want to pivot to where, to me, it’s more meaningful. So, that’s the biggest driver.

Mike Blake: So, implicit in a second act means you’re not already retired. Let’s put the financial piece aside for a minute because I think that’s a different kind of conversation. But assuming the financial wherewithal is there, and people sort of make a choice between a second act versus retirement, what do you think are sort of the markers that suggests that a person is going to be more happy having an active second act versus going off and playing golf, or fishing, or playing bridge, or painting, or whatever it is you’re doing as a retired person, or is that even a choice? Maybe I’m even positing a false choice.

Jim Deupree: No, it is a choice, and it’s interesting. It’s a conversation I have frequently. I haven’t met many people that want to go play golf five days a week, by the way, because, again, I’m blessed with working with people that are very intelligent and very accomplished. But the real marker would be two things. One is people who are good leaders. People who are good leaders still want to go build things or help things. They they can’t get enough satisfaction out of just being active. And obviously, people that still are healthy and have high energy. And you also have to think about the impact on your spouse. If you’re going to suddenly be at home all the time, and you haven’t been for the whole first years of your marriage, what’s that going to do to things at home? So, from that point of view, I think that’s the big driver, the people that just say, “I want to keep doing something.”

Jim Deupree: Now, what they don’t necessarily want to do is another job, and they don’t want to get sucked into a lot of travel or those pieces. So, for those folks, we talk about what we call a portfolio approach. It’s do two or three things that you enjoy and that are meaningful. And then, as time marches on, then you drop one of those. And now, you’re down to two. You’re shifting your balance. And then, ultimately, you may drop the second one. And so, it’s a way of saying, “I know I can still stay relevant as long as I want and be engaged; and yet, we can still have time to travel.

Jim Deupree: We have a thing, Mike. We talk about the 85/85/85 plan for people who are in that space. So, the first 85 is work. There’s 240 days in a year. So, it’s probably actually 245 days. So, the first 85 is work. So, you’re doing stuff that you would call work just at a diminished rate of intensity. The second 85 is intellectual stimulation. So, it’s going to conferences, it’s reading things, it’s learning things, it’s participating in discussions, so that you’re still keeping your intellectual juices flowing. And then, the third one is recreation and travel. So, more time with your spouse. And people really respond well to that notion. And most the people I work with have a lot of trouble containing the first part to 85. They want to keep expanding that to where it’s almost back to where it had been before.

Mike Blake: And so, in your role, I’m giving all of that extra self-promotion, but that’s okay because I think it’s important, because it sounds like you have that scope creep, if you will, in your chapter two. Do you or do people sort of have somebody else that tries to help keep tabs on them and say, “Hey, look, I thought you wanted a chapter two but you’re starting to look chapter one as of late”? Do you sort of help them manage that and help them develop the habits of being a chapter-two person?

Jim Deupree: Yes. And our business model is pretty unique. I think Mike mentioned that all of our clients are pay-it-forward. They’re wired to help other people. It’s part of our screening. So, we just have it, when you come chapter-two client, you become part of our family. And I look forward to and reach out to engage on both the personal and career basis and stay in touch. And no one has ever abused that. If anything, people are too careful about wanting to take advantage of that. But it’s been a wonderful part of what we do.

Mike Blake: So, we talked about second chapters but is that necessarily the upper bound? A lot of us are going to live to being 90 to 100. And particularly, if we have some medical advances, we’ll so mostly have our marbles when that happens. Are third and fourth chapters potentially on the table, in your view?

Jim Deupree: Well, this is either my sixth or seventh.

Mike Blake: Okay.

Jim Deupree: So, they definitely are. And I think I would say three would be a norm. I mean, the idea of a lifetime job has kind of gone away. The tenure in roles is reducing constantly. The time we spend in roles and the opportunities to make a change. So, if the average isn’t three or four already or within five years, I’ll be surprised.

Mike Blake: And what are the first steps of that transition look like? Is it just simply you to tell whoever you’re working for or with that I quit, you throw in the towel, or is there something that kind of happens that leads up to that, that begins that transition?

Jim Deupree: It’s definitely the latter. And so, before I started chapter two, I spent five years leading an outplacement center for C-Suite executives. And most of them had been completely surprised that all of a sudden, they’re no longer there. I mean, this wasn’t a client, but I knew one guy who foresee a six-month severance. So, for six months, he went out, and got all dressed up, and drove to a Starbucks, and just spent the day there, so he didn’t have to tell his wife he lost his job. It’s very-.

Mike Blake: Really?

Jim Deupree: Yeah.

Mike Blake: I always see that on TV. I never knew people actually did that in real life.

Jim Deupree: Well, in this case, he did. And it’s very traumatic to end up in an unplanned transition. Your family is upset. We’re gonna have to move. What’s going to happen to our country club status? And then, again, I get to work with people that it’s not about keeping the roof over their head, at least, short term, but it’s so disruptive. So, all of our work is now focused on planning ahead. It’s the voice in your head is speaking. And the time to start thinking about that is while you’re still in the role. And you start by saying you want to set your compass for what would you really love to do, what would what would give you joy. And it’s not just the job, the title. It’s the culture, it’s the nature of the business, it’s the meaningfulness of it, all of those points. So, you go through and define a handful of options. And typically, there are options a person hasn’t thought of.

Jim Deupree: The next step is, then, to say, “Let’s go talk to been-there-done-that people, other pay-it-forward people,” and they will have a completely candid conversation, “This is what we like, this is what we didn’t like, this is what surprised us.” So, then, you take those options off the table one at a time until you’re down to one or two. And the third step is, then, you say, “Now, I’m going to adjust my link, and I’m going to think about the kind of network I want to lead to that next role. So, I’m going to build a campaign. And then, I’m going to wait. I’m going to wait till the right opportunity comes along. And that may either mean the right job or it could mean I get a chance to exit in a financially profitable way for my company.” But all that time, you can actually enjoy the job you’re in more because, now, you know it’s not forever, and you have a plan B in your pocket, and you’re just ready to activate it whenever the right time comes.

Mike Blake: So, in case of transition, break glass kind of thing.

Jim Deupree: Right.

Mike Blake: And that scenario you bring up, I think, is so poignant because … and again, myself having just turned 50, one of the things I thought to myself is, “Well, I better kind of like the job I have because once you once you hit that 5O, getting that next job becomes a lot harder, and requires a lot more thought and a lot more preparation.” I mean, age discrimination is real, right? And so, I think, if you’re going to make a transition, obviously you can do it, you help your clients do it, but part of the reason also they need you is because it is, I think, all the more challenging, and you have to be more creative and, in a way, kind of create your own role rather than wait for somebody to give it to you. Is that fair?

Jim Deupree: A couple points on that, Mike. I think the age discrimination is not as real as many people feel.

Mike Blake: Okay.

Jim Deupree: I will tell you, if you’re a CMO or chief marketing officer, it’s real because there is a perception that you just are out of touch with the way that the 20 and 30-year-olds are communicating and acting. But we have a big glut of middle management in our country because of the past recession, and there is a lot of places where I called the silver savvy group is really needed and respected. But sometimes, it’s entrepreneurial companies. I’ve got a client who is a CFO for two or three startups, and she played a role not only of CFO but, pardon the expression, kind of a den mother role, and it was very much appreciated.

Jim Deupree: So, the second point is that people busy in careers did not understand how to play the game in finding a new role. It changes all the time. It’s changed dramatically. And even in the last three years, the role of search firms has dramatically changed and pivoting. And so, if people try to do this on their own, they end up saying, “Well, I think I should try this, but I’m not sure. So, I’ll wait till tomorrow. Then, I’ll wait till tomorrow.” And they keep procrastinating on taking the necessary steps. If somebody that they trust and has done it a hundred times says, “This is what you ought to do next,” then they go do it.

Mike Blake: So, when I think and I just reflect on the mentoring that I’ve had the privilege to do with some of your clients, I tend to think of people that are, at least, walking into chapter two, they’re thinking of a new career or sitting on a nonprofit board. Are those the most common options or what are some other alternatives if maybe those two things don’t necessarily appeal to you? What are some of the other items on the chapter two menu?

Jim Deupree: The most common one is probably advisory work. So, I’ll give you one example. One of my clients had had three chapters already. So, first chapter was in medical device field. Absolutely loved it. He was actually in the heart area. He loved being in the operating room. Then, didn’t want to move the family. So, second chapter was in financial services and wealth management. And the third chapter was in a big real estate investment trust. And now, it’s time. And so, as we went through this work, the first chapter was really the one that they loved the most of all the things they done. Going back at a lower level wasn’t gonna make a lot of sense. So, first of all, we had to build a bridge for 15-20 years later, how do you reenter? What are your credentials? And it led to finding the right people as sponsors and a series of advisory sort of board roles that have been really rewarding, lucrative hard work but a lot of fun as well. So, that’s the most common.

Jim Deupree: Nonprofit organizations, because most of our people are very active leaders, the pace is too slow. So, they like it for the giving back. They don’t like it for the pace. And actually, board seats are not a real common outcome, part, because they’re very hard to come by. And also, though, people who are used to making decisions are not always good on a board because, now, you need to voice your opinion, you need to respect the opinion of others, and you need to be ready for a collective judgment, not the one you feel is right.

Mike Blake: Yeah. I mean, that’s a great point. And we need to have an episode on boards too, but you’re right. Having having to share and share a lot, if you’re used to and frankly have been successful being in the driver’s seat, that’s gonna be a very difficult mental transition for some.

Jim Deupree: It is.

Mike Blake: Give me … well, I’m not really a war story, I guess a success story. What is one of the more creative second acts you can recall, or third, or fourth acts you can recall somebody creating?

Jim Deupree: Yeah, I love that question. So, I had a client who had been a serial CEO, been CEO two or three times, happened to end up with a very nice payday and said, “I just love hot air balloons. So, I’m going to become a hot air balloon pilot.” So, he bought a hot air balloon. He went out to Phoenix to go through the FAA school, got certified to fly himself and his family, really enjoyed that, decided he was going to take it the next step and get certified as a commercial pilot. And so, he did that. He was based in Florida. And he did that for a couple of years.

Jim Deupree: And then, ultimately, discovered that the life of a commercial hot air balloon pilot is you wake up at 3:00 in the morning, you collaborate with the other pilots, and decide where the right takeoff spots and landing spots are, so you can arrange all the equipment. You call your clients at 4:00 to tell them where to meet you at 5:00. And you go up in the balloon, and you serve them some champagne at sunrise, and then you can pack up the balloon, and you do the same thing the next day. Maybe you do it again at sunset. So, he had a blast doing it. And then, ultimately, after three years returned to a CEO role.

Jim Deupree: I’d like to make that point. I would love to see in our society people just at your age, people in their 50s, take a gap year. We take it as college students, but way too many people end up work, work, work, work until they’re too frail to travel the way they would like, and you don’t have as much energy around all the pieces. So, we could ever figure out in society how to say it’s perfectly okay to take a gap year in your 50s for one or two years, and then return highly energized. I think it’d be wonderful.

Mike Blake: Interesting you bring that up. So, that balloon story, first of all, it hadn’t occurred to me there’s a commercial pilot rating for hot air balloons. But it makes sense, right? You’re not getting me in a hot air balloon anyway, but if you were, I’d rather it not be the second flight that person ever has taken. So, I learned something there. But interestingly, that did wind up in effectively being, I guess, a three-year sabbatical before he returned to his conventional career. And hours aside, odd hours aside, I’m sure is very rejuvenating for him.

Jim Deupree: Absolutely.

Mike Blake: And he probably has about the best photo album you can imagine.

Jim Deupree: I’m sure that’s true too and lots of [indiscernible].

Mike Blake: So, what is the process? I know you go through a pretty detailed and lengthy process on how you figure out what that next act – I’m going to call it next act from now – on should look like? Can you tell me a little bit about that and why those steps of that process are so important?

Jim Deupree: Sure. It’s really three steps. So, step one is discernment. It’s what would you really like to do, what culture would you enjoy, are you better suited to a small company or a large company, all of those kind of factors. And we do that through a series of assessments that we put together. I use a term that … again, I get to work with very bright people. They know things about themselves, but if I use the television vernacular, they don’t have the dots connected as high definition pixels. So, the picture is not clear. They’re just data points.

Jim Deupree: And so, through that process … and we end up spending three hours with an industrial psychologist that I’ve used and we’ve done this hundreds of times together now, and it’s very revealing process. And now, we typically say, “These are the three or five options that you should focus on.” Usually, half of those are ones they’ve never thought of or never occurred to them. We also say, “These are the things you should avoid,” because when people start thinking about a transition, they want to look at everything. It’s like a big market, and I want to go down every aisle. And it’s a mistake to chase rainbows, and you confuse your friends and you say, “Well, I was talking about with this. But now, I’m talking about this.” So, it’s important to say, what should you avoid and what should you focus on? So, that’s the step one.

Jim Deupree: And ,then once we get that defined, it’s these conversations I mentioned earlier with been-there-done-that people. And you say, “I know I could do that, but that’s not exciting to me as the second one on the list. So, I’m going to drop that went off the list.”

Jim Deupree: The third part is how do you get yourself in the market? And that means that the opportunities, the ones you want are going to find you and they’re gonna find you through the way you represent yourself on LinkedIn, they’re gonna find you through the leadership story that goes to your friends and colleagues. they’re going to find you through what you say when you get a chance to talk to people face to face. And one of the things we’ve learned is the more crisp you are, the faster things happen.

Jim Deupree: People that say, “This is what I want,” don’t get very far. It has to be, “This is how I can help this organization grow and succeed.” And then, people that say, “I can do anything,” are not credible. So, it’s a whole process to say, “This is your message and this is where you play it and how to play it.” And then, it’s just working with them. We end up with some amazing stories with people about once they get in that stage, and sometimes things happen, they need to stay for a while longer or all kinds of things, but we end up being an advisor through the process of exploring and even negotiating roles as well.

Mike Blake: So, we’re talking with Jim Deupree of ChapterTwo. So, I’m going to sneak in. I’m going to sneak in some free consulting for myself or asking for a friend because I have you on the podcast. Have any of your clients ever gone into academia as a next chapter?

Jim Deupree: Yes.

Mike Blake: That’s something I’ve thought about because, one, I look the part, but I wonder how many people kind of think, “I really wish I could have studied X when I was in college,” and you sort of go back. And sometimes, going to college too, when you just don’t give an F what anybody thinks about you, that can also be very liberating, I would imagine.

Jim Deupree: Yeah, Mike. And so, a few years ago, more than a few, probably 15-20 years ago now, I actually explored pivoting from when I was at IBM into teaching business school. And I met with the dean of a business school, a noted business school, and he said, “You’re not going to be happy.” He said, “First of all, the best executives are not necessarily the best teachers. So, we would need to figure out if you are really a good teacher. But secondly, you’re not going to be happy because in academia, there is a pecking order. And if you don’t have a PhD, you don’t have a voice at the table. You may sit there and listen, but you don’t get to say, ‘This is how I think we should do it.’ And then you get no vote. And so, unless you’re willing to take the time out to go do that, just keep that in mind.”

Jim Deupree: Now, since then, as you mentioned, I teach MBA students at Kennesaw, and I teach ethics. And I have complete freedom for how I construct that course and teach it. But many of the courses now are highly scripted. 80% of what you teach has to be from the book, basically. And so, you don’t have the degree or freedom to go build something that you think. So, it’s a good gig. It pays best for people that have a CPA because there is a real shortage. Pay’s worst for people that want to be an English teacher. It’s nice summer vacations. It can be a platform for consulting, but it’s the driven people that are most of my clients, a very few of my selected that. A couple have but very few.

Mike Blake: So, we’re running out of time, and we want to be respectful of your time. I know you got to get back to doing what you’re doing. But the last thing I want to ask specifically is why is an outside perspective so helpful? I mean, everybody that you’re dealing with – I know because I’ve met them – they’re intelligent, they’re focused, I would even say largely self-aware people. Why do they need help figuring out something like this? Why do they need an outside party, a third person, an advisor to help figure this out?

Jim Deupree: So, everybody needs somebody to bounce their thoughts off of. And what I’ve learned is friends don’t work for this discussion. They won’t tell you what you need to hear because they’re afraid of hurting your feelings. And sometimes, they have their own bias about, “Well, if you got into this, then there’s a way that that would actually help me too.”

Jim Deupree: The second thing that happens, if you talk to three lawyers, you’re gonna get three different opinions. And if you talk to three friends, you’re going to get three different opinions. So, you say, ‘All right, I’m going to have a hundred cups of coffee over the next year. And with my friends, I’m going to figure this out.” At the end of the year, you have 50 different opinions, and they don’t jibe together. And generally friends don’t … this is not your specialty, it’s not their specialty. So, how this whole process works has a big impact on the really realism of the things you may consider.

Jim Deupree: So, I just have learned that people waste a lot of time and got nowhere without this kind of help. Now, obviously, some people figured it out, and some have done it brilliantly on their own. Some have been lucky. It’s not for everybody, but for those that sincerely want to say, “I really want to get the best next act in my career,” I believe that that this kind of advice and process is immensely helpful and makes things work faster.

Mike Blake: And that sounds a lot like what I advise people when they’re trying to get advice in their startup. Your friends will cheer you on because frankly, they don’t have any skin in the game. The skin in the game is to spare your feelings, basically. And that’s often where the worst advice comes from. And I’ll bet you, there are a lot of similarities there. So, I think I understand that. Jim, this has been a great conversation. We’re running out of time, but I’m sure there’s lots of other questions we could have covered and should have covered. If somebody is going to want to contact you and learn more, how can they do that?

Jim Deupree: The best way is through our website, which is www.chaptertwo.net. And it’s T-W-O, not the number two, and there’s no hyphens or anything. There is the “contact us.” You can get directed to me through that. Also, there’s some pretty useful information there. So, chaptertwo.net.

Mike Blake: Well, thanks again. That’s going to wrap it up for today’s program. I’d like to thank Jim Deupree of ChapterTwo so much for joining us and sharing his expertise with us. We’ll be exploring a new topic each week, so please to announce that when you’re faced with their next executive decision, you have clear vision when making it. If you enjoy this podcast, please consider leaving a review with your favorite podcasts aggregator. It helps people find us, so we can help them. Once again, this is Mike Blake. Our sponsor is Brady Ware & Company. And this has been the Decision Vision Podcast.