Allan milham Allan milham
Podcast 255

255: A High-Impact Transition into Your Third Act with Allan Milham

Today, I’m speaking with Allan Milham. Allan is a Master Certified Coach and the Founder of Questage®. His company helps leaders deepen their emotional intelligence and become more self-aware by creating leadership and development programs to expand awareness, increase performance and fulfillment.

Allan has a world of experience, a graduate degree-level education in our field and more than 25 years of experience impacting top-performing teams and individuals ranging from startups and Olympians, to Fortune 50 companies.

With his unique perspectives on the retirement stage of our lives, his team is focused on capturing the values and core beliefs that truly matter by offering highly customized programs tailored to each individual or team's needs and desired outcomes.

In this conversation, we dig into Allan’s high-impact concepts for the transition into your third act, why baby boomers may hold more value in today’s workforce than they think, and how everyone has the opportunity to be a leader and make an impact as they transition to the next stage of their life.

In this podcast interview, you’ll learn:
  • Why Allan’s road mapping process for the third act of life applies to all retirees and not just top-level executives.
  • The long-term impact that leaders in retirement are capable of.
  • The three P’s of a high-impact transition and why Questage® dropped the term retirement.
  • Why the ideal client of Questage® must believe in paying it forward.
  • Helping their clients determine the holistic lifestyle that focuses on productivity, paying it forward but also enjoying their personal life.
  • The gap in the baby-boomer demographic and how we could see four generations in the workforce.
  • Allan’s advice for those who are considering a big career change, and why organizations value boomers more than they think.
  • The Questage® 90 day roadmap process and how it works over a long period of time.
Inspiring Quote
  • "With zero training, Olympians can silence their inner critic and listen to a voice of positivity that says, ‘Let’s go for it.’ If you could master that at 20, my leaders in their 30s, 40s, 50s, and 60s certainly can master that." - Allan Milham
  • "We can't rush the discovery process because whatever comes out of that is going to be the seeds of where you're going." - Allan Milham
Interview Resources
Offer valid in the 50 United States and the District of Columbia, to first-time requestors. During the offer period, receive one (1) in-stock book per request. Limit (1) book per week per household. Limit three (3) books total each calendar year, between January 1 and December 31. Offer valid while supplies last. Howard Bailey Financial, Inc. reserves the right to cancel, terminate or modify this offer at any time. Void where restricted or otherwise prohibited.
Read the Transcript

Casey Weade: Allan, welcome to the podcast.

Allan Milham: Thank you, Casey. It's really great to be here. Excited for this.

Casey Weade: Allan, I've got a lot of retirement coaches here on the Retire With Purpose podcast, but I must say, you seem to hold a unique place in that stratosphere of retirement coaches. There's a wide range of different types of retirement coaches out there in the world today, some that are just in the game, some that have been doing it for nearly a lifetime, such as you. So, you have a world of experience. You have a graduate degree-level education in this space. You're one of the top coaches that are out there today in this space, but I think one of the things I found most unique about you, Allan, is your experience working with, not just top-performing individuals and teams, but Olympians, Fortune 50 companies. And I was curious, as I'm reading that, I can just imagine the average retirees sitting here going, so he coaches Fortune 50 executives into the next phase, Olympian's into the next phase. How does this apply to the average aspiring retiree?

Allan Milham: That's great. And I'd like to say that we all are Olympians to a certain degree, but many of us, obviously, we don't go for the gold. And the opportunity I had really was at the beginning of the Olympians, back when they were coming back from going for the gold, I was with a career consulting firm, one of the world's largest, working out of the San Francisco office in the 90s. And it had such a huge impact all the way to who I am today. And the reason for that is that I can understand why they were well muscled in their sport, Casey, but what I couldn't get my head around is how at the ripe age of 20 and 21, they weren't freaking out, all that pressure, particularly with the United States and how we love the win, and every one of them with zero training had the ability to be able to manage who had the microphone in their head between that voice of fear, doubt, anxiety, sort of that inner critic versus a voice of positivity that said, let's go for it. And I thought, my goodness, if you could master that at 20, 21, my leaders in the 30s, 40s, 50s, and 60s certainly can master that. So, that really shaped my performance-based model that I've been using for the last couple of decades. And it certainly has shaped my road mapping process for the third act of life.

Casey Weade: Well, I'm really excited about getting into the road mapping process here in a little bit. I think we're going to find that very, very helpful. I just wonder you've got all these retirement coaches coming out of the woodwork, varying degrees of experience and education. Why? Why do retirees need coaching? And I mean, is it really that hard to retire that we need a retirement coach of your level?

Allan Milham: That's right. Yeah, yeah, yeah. Well, I have to probably place myself in an outlier category for you because we don't use the word retirement. So, we used it originally, it was high-impact retirement for the third act of life, and our prospects and our clients just shot that down, like retire? I'm not retiring. I don't want that word hung up on me at all. I'm active and I want to continue to be active. And so, we have to do a rather extensive redesign because I just assume that retirement was a part of what we call that third act of life.

And the truth is today, at best, it's probably protirement. And the reason that I think it's such a big conversation right now is that we're the first generation, and I say we because I'm in it, almost 30 years older than you are. We're in a time where, thanks to our medical and thanks to technology, we're in a time now where if you think back to what your grandfather did, 65 or 70, that was very different. The idea of knitting or fishing full time is just off, it's not even on the agenda. People desire in the third act of life to be very, very proactive, to be purposeful, and to be productive.

And so, the Questage High-Impact Transition program does not mention the word retirement because for our clients, not just not, I actually believe that word of sort of going to dissipate over the next generation because you've heard the 60 being the go-go years, the 70 the slow-go, and the 80's no-go. And my belief is in the next two decades, we're going to be pushing that out. One of my favorite stories is a man I met in Kansas, 88 years old, had a very successful business with prize machines for a very large fast-food company in the United States. And I was introduced to him and I was just struck at 88 of his presence and his energy. And I said, "When are you thinking of slowing it down?" And he looked at me, saying, "That's such a great question. I just talked to my wife last night about that. I'm thinking of this next year, I'm going to bring it down to about 40 hours a week." And I just thought, what an amazing attitude, right? 88 years old.

So, I think you're seeing a very different narrative. And for a lot of leaders, because I'm in the leadership space, they've spent so much of their identity in their career that when that day comes, whether they won the money game, whether the organization's saying, "You're 65, you got to go," or they just say, "Look, I personally feel it's time." For a lot of particularly men, when you remove that business card and that title, there's no there there because their entire identity had been focused on this thing we call work.

And it's interesting, I created Questage a couple of years ago, really from a memory that I had as a career consultant in my 30s when I was about your age in San Francisco. And this one executive came in, and the way you worked with us is the company had to afford the program. You couldn't walk in off the street. And so, here, in front of me, this gentleman by the name of Tom, who's probably about 60, 65, CFO, and it was an acquisition. So, he didn't get the nod. The other gentleman, the leader got the nod.

And I'm looking at this amazing resume with a great education. And the depression and the anxiety in him was just stunning because his whole life had been his work. And when that business card was removed, we had to start really from scratch to be able to look and have him own his experience on that resume and then to retool it in a way to move him passionately forward based on the skills and the competence and the values that he wants, but Casey, I never forgot that thinking, wow, particularly for where we are today, we need leaders to continue to lead for the next decade. We can't just hang it up. Until your generation gets another 10 years in, we have a void because the next thing, the Gen X is only a 10-year generation. And so, we need the millennials to get a little older to be able to fill that leadership void that's happening with regard to the baby boomers.

So, I think we could not have enough coaches to be helping in partnership to really have that third act of life be meaningful, to be full of productivity. If you're a Questage client, you have to have a desire to pay it forward. So, we insist that if someone's working with us, that they have an innate yearning to be able to continue to lead, whether that's in foundations, charity, volunteer, consulting, doesn't matter, but we really want that leadership narrative to continue. And so, does that help?

Casey Weade: Yeah, well, speaking to that, and we talk about leaders, it seems like the right individuals for you or those that are leaders, those are the ones that fit best into the Questage Program, so I would view this; however, one of my favorite mentors, Andy Stanley, is what I would consider one of the biggest names, if not the best leaders out there in the world. And he argues that we're all leading in some capacity. We're all leadings.

Allan Milham: Correct.

Casey Weade: So, what type of leaders? How do you define leadership? And what type of leader would be the best fit for this program?

Allan Milham: Well, for the Questage High-Impact Program, it really is for what I refer to as top-performing leaders, that they've been able to make their mark. They were able to navigate to the top of the organization to be able to lead with great momentum and great capacity. I share that definition. All of us have the opportunity to lead and to be leaders, right? And my belief is that leadership is always on. It's not just about your work. It's how you lead at home, how you lead it with your spouse, your children, how you lead in the community. And it's interesting because leadership came to me at a very early age back when I was 10, 11, 12, in Boy Scouts and in church and in school, student representative, and whatnot.

And I'd always been fascinated about what had left some people plateau and others continue to thrive and climb. And so, I've always been a student of that, around human potential. And so, while I have to have the privilege to be working rather high up in organizations, your point is well taken that when we get to the third act of life, it's a leadership conversation, no matter where you are in the organization, to take control and to be able to look to say, how can I pay it forward? How can I be relevant? How can I be productive? And how can I really be seeing the third act of life through the lens of positivity? Because when we're unplugged and when we're separated from the herd and not having a network, that positivity lead becomes a negative narrative, right?

And we go in and look at nursing homes and seeing how they're living so long and they're thriving because, for many of them, they're lifelong learners. In fact, one phenomenon that's happening now is nursing homes and living facilities are being placed on university campuses. We have an amazing new project that opened up on the Arizona State University property, and they have full access to classes, they have full access to the university. So, this learning mindset of being a learning leader in your life, I think is really taking hold, and it's going to continue to grow.

Casey Weade: This is one of the things that gets me up in the morning every single morning, gets me excited every single day about what we do, is we do how– I feel like we have such a massive opportunity today with the largest generation in history stepping into retirement with financial independence if they can focus those energies away from what they've been working on for the last 30 or 40 years, which is typically accumulation. All they've been focused on is accumulating as much as they possibly can. Now, if they can let that go, I think it could change the world.

Allan Milham: Totally.

Casey Weade: And I want to know what impact you believe this generation really can make if they show up as leaders in retirement as a whole. If we really grasp this and really take hold of this and move it forward, what do you think the long-term impact of that is?

Allan Milham: I think the long-term impact is, well, short and long, I mean, when you say long-term impact, we're talking about what kind of change can the boomers do in the third act of their life. They can have a positive ripple effect in our world. And we can spin the wheel around whether we're talking about culture change, whether we're talking about climate, whether we're talking about economies, whether we're talking about social justice. If we can just wake up and be very clear of what each of us feels a yearning for to make that difference in the third act of life, the ripple effect is huge, but we don't have time, right? I mean, I'm humbled at 64 years of age to wake up every morning, still thinking I'm your age. I mean, I'm just like, where did the decades go? I'm energetic. I have a lot of fun, but I can't account for, like where to go.

And so, when I'm now looking forward and looking at the next maybe two or three decades, that matters to me. It's like we don't have the luxury of time now. And I expect that we all have a little slowdown, but for me, that's why Questage matters. This is an important legacy for me to be able to be in this conversation and to ensure that we have boomers in the right mindset that they're not coming with scarcity. I challenge my leaders to be very mindful to what they absorb around news because there's a lot of negative stuff, and that can impact our systems if we're not forced yielding to be able to say, okay, I got it, but I'm not going to take it in, because for some, as we get older, some feel hopeless, like how can I possibly be a change agent without this enormity of noise and problems we have? And so, I really challenge us to be able to look at what we can control and how we can individually be committed to wake up, as you say, every morning, excited to be able to make that difference in whatever domain they're called to do.

Casey Weade: Make that impact. You talk about a high-impact retirement.

Allan Milham: Correct.

Casey Weade: I want you to define for our listener, what is a high-impact retirement? How do you define a high-impact retirement? And then, where does leadership show up in retirement? And is there a spectrum there?

Allan Milham: Yeah. So, we talk about high impact, I mentioned that before, but I sort of call the three P's, right? One, it's all about purpose. And you've had some of your folks talk about the power of purpose, it's embedded in your work, but as we get to the third act, we get to reengineer what that means, really being very purposeful. And in the first phase of the work with our clients, we have a discovery process. They certainly know who they are, obviously, the third act of life, but we're actually taking some very unique assessments that have them really take stock of what really matters to them now in the third act.

Our clients come with a robust resume and a very stretched-out toolkit of competency and skill. What we do is to say, with all due respect to all that you have on the table, what are you passionate about? Which of these competencies and skills just have you thinking, if I could do this daily, game over, right? And so, we have to undo a little bit and take some of the stuff out of their 20, 35, whatever years of gaining to really go back and really pull out the best in class for them.

And then second to that is looking at what does productivity mean to you. And again, we have to sort of get a new mindset here because productivity for a lot of leaders meant their day job, and getting up and going almost on autopilot. My wife just retired after 33 years as a senior executive for Marriott. And I will tell you that our daughter, who's 21, I can just imagine our grandchildren looking at my wife and saying around the age of 10, so another 10, 15 years, just saying, "How many years did you stay in that company?" Because that we're now going entrepreneurial, so we're staying less than 40 months in a job. You've certainly read about the great resignation in April this year, where four million quit and another two million in May. So, this is a phenomenon I can't get my arms around, even though I'm a boomer, and loyalty and stay the course.

And when I started in Mariott and when I left Mariott at the age of 30, 31, I was a regional director of sales and marketing. And my mother had two words for me, get therapy, because back then, the big company will take care of you. It'll give you the security and just stay the course. And that's not the new normal. So, we really look at what are you looking for around productivity? And productivity, the cool part for the third act of life is it is the productive piece around where do you want to pay it forward, around work and volunteering or teaching. And then, what about life productivity? And that's the fun part for a lot of our clients because it's really looking to say, what's the holistic lifestyle that I yearn to have, around travel, family, health? And so, it really works both sides to be able to move them forward. And what we get is a really positive mindset that comes out of that that has me excited for Monday mornings to be able to get up.

We have dear friends of ours who have retired, and they're fascinating. They both were successful in their own way and they shared with us when they go to a cocktail party, they never sit down at a table. They actually stand and mingle. And if anyone comes up to them and introduces themselves and says, "So, what do you do? What's your career about?" They stage an emergency and say, "You know what? We have to go. Well, you know," because they don't want to be in that conversation. They don't want to live in the past. They want to be with someone that says, hey, who are you? What are you about? What are your hobbies? What are you doing? Where do you live?

And so, it's really an important distinction because, for a lot of people in the third act of life, they're looking through the rearview mirror and living what's already happened. And for us, back to your point about how could the baby boomers have an impact in our world? Well, the biggest part is not look in the past, but look in the future, what matters and be in conversations with that so you can start creating networks and communities to really move us forward.

Casey Weade: So, we had three P's – purpose, productivity, and positive mindset?

Allan Milham: Correct.

Casey Weade: Awesome. I love that. And I'm wondering how many individuals are actually falling into this category, on average, and from your perspective, maybe even know some numbers or statistics to a certain degree. Are most retirees living a high-impact retirement and showing up as great leaders in retirement?

Allan Milham: So, I don't have global statistics on this. We're in sort of a niche area, and it really is sort of split. I mean, we're talking about high impact. We're talking about sort of looking at the third act and being really successful. And we have to be mindful that we sort of, I call it the tale of two worlds because Bloomberg had an article out in April that talked about the fact that a lot of people were retiring early. They wanted to live their life now. So, through the pandemic, what families were doing, as they said, we had retirement scheduled for five or ten years, but we rejiggered it because it's not worth the price tag. It's too stressful. The virtual environment, it's just not fun. They're not in teeming environments.

And so, there's one piece where people who have done well with their portfolios in the market or whatnot have literally stopped the game to be able to be in, I want to live well now mode. Unfortunately, we also have the other side, which you well know of, and that is the fact that we have a number of boomers who are going to have to work well into their 70s, if not forever because they don't have the financial reserves. And so, that's going to be interesting for us to watch because basically, we're going to have four generations in the workforce, which has never happened before. And it's very likely that we can have a 72-year-old person reporting to a 28-year-old manager.

And so, I'm really curious to watch how that plays out, but there was a research project or research that came out that really spoke about sort of the mindset around what's the mood around retirement. And for a lot of people, they think that the best, and I'll get you the research on, specifically with the numbers, but there was a very large percentage of people thinking that work opportunities would be great for them in the third act of life. And as we look at the work and what's needed, they don't need the benefits. So, they come at a pretty cool price tag because they have their health care for. And so, it's nice to see that there's a percentage of boomers feeling optimistic and feeling positive, but we have to be mindful at the other end of the continuum, there is a part of our population that I worry about because how do we ensure they have the resources and to be able to live into their 80s and 90s if they don't have the financial wherewithal to do so? And that concerns me.

Casey Weade: Yeah. I wanted to ask you, as you're working with individuals, exactly how you help them uncover where they make this big impact. How do they recognize their full potential? But I think that ties in really well with one of the questions we had submitted from one of our Weekend Reading listeners. So, those of you that have subscribed for Weekend Reading for Retirees at, you have the ability. You received an email about a week prior to the interview. You can submit your questions. And that's what we did with Patty.

Patty said, "Is it practical to try to start from scratch in a new area? For example, I thought it would be cool to work on climate change as a data analyst, but my background is in electrical engineering, so I'd effectively have to go back to school for quite a while, I think." And I think a lot of individuals are going through this. She went on for quite a while. I think she has quite the resume. And I think that there's a lot of individuals that feel this way. They've been in the same position for a lot of years, but they're not necessarily passionate about it. There's something else they'd really like to do, but they go, I don't know if I have the time to start over again.

Allan Milham: So, great. First of all, I love her vision. That is awesome. And consider, if we can, a 3x3 box, just imagine we've got this box with nine boxes within it, right? Three rows of three boxes, and imagine that, so for Patty, she's on the upper left-hand corner right now with her resume, with her specific skills of what she's done. And for her, to be a part of where she's desiring to go, we have to ask the question, what are the transferable skills that we can leverage to move her over to that?

Now, if she's in box 1, that means that she touches boxes 2, 4, and 5 if you're tracking with me visually here, right? So, that's the easiest transition because touching that box 1 means that we can use those transferable skills to move her into something new. And what she's pointed to is box 9, right? If there is nothing that she has that she can repurpose into where she's wanting to go, therefore, box 9 does not touch box 1. That is a reengineering job. Now, boy, I'd love to talk with her because I think, first of all, if I'm a betting man, she definitely has transferable skills that we could reengineer to be able to have or at least be in the conversation because there's so much she hasn't been really specific of what she wants to do in there, but I have to believe there's a way. I mean, my gosh, it's so emerging.

And second is that years ago, there was a fascinating research project that came out. They interviewed thousands of H.R. professionals. And they basically asked the question, are you looking for someone that can do the job? They have the skills. Are you looking for someone that's just motivated and interested in what you're about? Or are you looking for someone that really connects with your culture? And when you meet them, you're just like, wow, you're one of us. And for a lot of people, they thought, no, it's all skills-based, we need the skills. Now, the response that came out of that was really surprising. And certainly, for high technology, bio, or medical, obviously, skills matter greatly, but for a lot of work, the number one response was, give me the person that's compatible with us. Give me the person that fits with our culture and we'll get them what they need.

So, back to Patty. I'm curious just with that, I'm hearing a value proposition here. She wants to plug into something that is desperately needed right now in our world of fix. And so, the job is to look at how you can transfer skills based on what you're looking for and reengineer it that way. And if there's some schooling, I'm not a fan of her investing eight years ago, get four or five years in a page, unless she's absolutely a lifelong learner and desires to do that, but I would suggest there's a way that she can actually get into that world with her resume. We just have to reengineer it and how to sell it from there.

Casey Weade: So, if someone's feeling this way, they might be surprised that they actually do have skills that would apply to an area that they want to be in, that they didn't know actually would apply in those areas. And in addition, it's just like our business, right? How many times have we been told, you hire for culture and then you train for the skills? And there's a lot of companies out there today that I think are adopting that. And that's not the way it used to be. I think, as a whole, most businesses hired for the skills, and then they try to figure out how to fit you into the culture. And I think we've adapted to that over time.

Allan Milham: Agreed. And here's a secret weapon for Patty. Here's a secret weapon for Patty. I'm assuming she is a boomer. Organizations love our work ethic, organizations love the boomers. They're not playing games. They're going to show up on time. They're going to be respectful. They come with professional skills. That's right. And that's the thing that really is exciting for a lot of organizations because they know that they'll have dependable people that they'll be there to show up. And that means a lot for organizations.

Casey Weade: Yeah, we just hired our first boomer. So, I'm really excited to bring him on the team because he's just...

Allan Milham: Awesome.

Casey Weade: Yeah, and you can just see kind of a sense of wiseness that he brings to the table. So, I'm excited to see what he does, but I want to ask you, Patty is talking about starting a new career in a way, a lot of individuals, it sounds like you're working with are starting a new career, starting a business. They're going to continue to work. Do you find that most individuals, in order to have a high-impact retirement, do they have to be working? Or are you redefining what work is? Is there a different definition you have for work at this stage?

Allan Milham: Yeah, and that's why we use the word productivity because work has so much that comes with that word. And for a lot of people, it's not a positive one, right? I mean, if they've had to stay in there to pay the bills or whatever, so when we talk about back to the three P's or on purpose, productivity, and positivity, because productivity is very fluid. And we do tenure mind maps. So, let's just say I've got a 65-year-old person who's retired, and she or he is looking at the next decade. We're looking out to say, "Well, let's talk about productivity, and why you want to pay it forward. And let's talk about how much time you want." And it may be that they want to be there 30 hours a week now, but maybe in five years, it's going to go down to 15 hours a week. So, we get to holistically look at the time and say, "How do you want to be productive, both from a place of paying it forward as well as holistically looking at lifestyle? And we need a couple of years because it's such a shift.

My wife and I are operating without a blueprint right now and I'm to this business because we've been pretty Type A throughout our careers and now we're seeing that we have a way to flex it up and down. And that's the beauty of productivity, is that hopefully, if well designed, I plan to do this for as long as I can because I love it, but it gets to scale versus when we say work, it's like boundaries come in around. Is that 40 hours? Is that 30 hours? And does that mean going somewhere? So, we get really, really to start in a white room to recreate a blueprint or a road map that just is a lot of fun and taking ownership of what you bring to the table.

Casey Weade: I'm thinking this time, you said, the mind map, the road map here, this is probably going to answer the next question I have, and it's one that I get quite often, they'll say, well, I want to start a new career. I want to start a new business, but I want to maintain my flexibility. I want to be able to flex, as you said. I want to be able to have those weeks. I go, you know what? I just don't want to work this month, and then I'm going to have next week where I want to put in 80 hours. How do we get to this white space and really map it out to make sure we maintain our flexibility while still getting the same level of productivity we're trying to do?

Allan Milham: That's right. So, there's good news in your question, and that is partly because of the pandemic, I think this is a part of the great resignation that occurred, as there is, and this is more a younger generation versus older, but we certainly can appreciate this because the new worker today wants that flexibility. They don't want to be tied down to a desk. It's really much more, Casey, of an entrepreneurial mindset, if you think about it, where you have that fluidity, you have that flexibility, and you want to bring productivity, you want to bring results, but you want to be able to do it in a way so that it serves your road map.

And my belief is, certainly with the need for skilled workers in the next couple of decades, that can happen. It can be really beyond the terms. Remember, I said there's a leadership shortage right now. So, that senior leader got to say, "Hey, I have 35 years of unbelievable knowledge and wisdom, and here are the skills. And can we sort of co-create a way where I could pay it forward for your organization and design from there?" And that's what's happening today, which is really exciting. So, I want to go back to your bold hire of a baby boomer because you just brought in, I know she or he has wisdom. I mean, obviously, they have wisdom, but how does that knowledge you're going to infuse into your culture? Will it be respected? Will it be desired? Because some of the younger generations like, hey, that's all fine with your long-term career. I'm going to go do my thing over here.

So, there's that whole assimilation and learning. My last book was called Out of the Question: How Curious Leaders Win. I co-authored that with a colleague of mine, Guy Parsons, and the whole piece of the book was talking about the learner leader versus the nowhere leader. And the nowhere leader was the old general, the commander control, do as I say, leave your emotions at home. And that leader is quickly going to the cliff. And this new learner leader mindset where they're more of the guide than the general, they don't have to know all the answers. They lead with curiosity. And those kinds of leaders are going to create the compelling cultures of tomorrow. And guess what? With all these resignations, it's going to force organizations to get culture right, right?

Casey Weade: Yeah. It's definitely more important than ever to really determine what kind of leader you are and make sure you're heading towards that leader leader, servant leader, or learning leader.

Allan Milham: That's right.

Casey Weade: I want to hit on the custom road map, specifically, because I did get really excited about this because I love a good road map. I have had to get a road map since I was a little kid, as far as setting goals, putting myself on a track, knowing what I need to get there. So, I love a good roadmap. We use something very similar with the families we work with when it comes to their financial life. This is part of your individual transition program. What does a custom road map actually look like? Can you make this more tangible for us?

Allan Milham: Sure. So, we got into this, it goes all the way back to my career consulting days, if you can believe it. So, it's really beautiful to have this beautifully tied for my entire career. And for a lot of leaders that are coming into the third, or I would say anyone coming into the third act, a lot of them, they need some structure, they need some guidelines. They're okay, I've got my resume. I've got some interests and whatnot, but what do I do with it? So, what Questage does, it sort of like takes all that stuff and shakes it out, and then we capture the essence of what's most important for the third act of life.

So, we capture the values and the core beliefs that matter. We use an amazing tool out of South Africa that it's coming into America, both in organizations, as well as we use it for the third act of life that really allows our clients to understand their core motivation, and there are nine motivations in this model. And it allows them then to look at the lens of who they are through these positive qualities, these core strengths, but also blind spots. We all come with blind spots and weaknesses. And so, we integrate that particular assessment along with some core exercises to be able to start looking to say, what are we going to pack for the journey? What matters to you? Skill, competency, values, motivations. And what do we need to let go of? What are the things that you no longer want to touch? Because sometimes we think, well, I got to just pack this in here because I know it, or it's going to be a part of the job.

Well, not in this new conversation because we really get to say, what do you pack or want for the journey that's going to excite you most? And then, we litmus test it because the third act of life roadmapping process is definitely a team sport. So, we build an advisor network, it's their individual network, where we start leveraging and bringing in people that really know them so we can check to make sure how we got it right, and they can challenge them because they have the history with them. And so, we bring in folks, and also, on the flip side of that, we begin to create a new network for them because their own network is going to die out. It's no longer relevant if they've left their full-time work, then they have some people to go with them, but the third act of life is very much a team sport and about really showing on how to harness to build your new network, your new community that you can lean into.

And then, from there, that road map starts to get very tactical because now, we're going into scenario testing where we're looking to say, okay, here are the skills and confidence, here are the values. We know your productivity spreadsheet, this is where I talked to earlier about how much work, how much time each week over the next coming years, as I say, we play with a decade forecast model. And then we begin to look at scenarios, what are possible scenarios that fit the attributes of what you've got here? And so, this is the research and targeting, and this is where they go into the network and say, hey, what do you think about this possibility? Do you know anyone? So, this is where we actually really want to warm it up so they're not going cold at all.

And then, much like in the old days, they get out and have informational conversations with possibilities and begin looking for the right opportunity. So, it's a 90-day process to get all that built, and once it's built, then they go out at their speed and how fast they want to make this transition happen to be able then to plug it in and put it on steroids.

Casey Weade: I've done so many of these types of exercises over my lifetime, and a lot of these things, you go out, you walk through all these exercises, do the coursework, and then you end up with something. You feel really jazzed up about it. And then it ends up stuck in a drawer for the next decade. And you shared that this is a decade forecast. And you also said that it helps keep what matters most to you front and center. So, how is this utilized over time to make sure that you're continuing to keep those things front and center? How often do you revisit it? How often do you update it? How exactly does it work over time?

Allan Milham: Well, look, the first thing that I want to speak to is the fact that there's a new ownership that comes with this process because there are sort of, we're moving into a new active life, and it's the third act. And our belief is it can be your best active life. So, when I talk about mindset, there is a bit of shifting of what you're letting go of, to say thank you, it's served, and that's now in my rearview mirror. And I know it's important to underscore that because a lot of leaders when we go through the process is amazing how they don't own your gifts. It's like, oh, yeah, I did that. Well, yeah, I did that.

So, there's an ownership component here about really looking in the mirror. Bring that mirror down and look and say, wow, this is the new me. This is what I'm taking forward. This is what I'm communicating, and then to take it out. And the beauty of the process is that once they've gone through it, they can certainly come back for a tuneup if they want, but they got it. So, now it's a polishing activity every 6 to 12 months. How am I doing? I said these things I thought were the right proportion of time, but now that I'm doing it, I want more vacation time, or I'm loving this work I'm now, and this assignment is so cool. So, I'm going to push back a little bit of the leisure stuff because I'm just loving the opportunity I'm doing to be productive. And we certainly want them compensated, if that's important to them, give it away for free unless they choose to.

And I think the other piece, Casey, is that this is always a team sport, but it's a partner sport. So, we bring the spouse or the partner into the conversation because obviously, in the old model where you had, maybe the traditional model of the male person working and the wife having the more important job of raising children and whatnot, right? And then all of a sudden, this whole thing stops. And so what about the spouse? What about the partner? So, actually, two I mentioned from Cape Town, South Africa, we actually extend that to the partner because they need to be in this narrative. Because they want to live the third act of life together, so we absolutely need to have that woven in and to make sure that they're both excited and signed off for the game.

We had a 71-year-old client who's just really, very powerful. He was a competitive achiever in this motivational wheel I'm talking about. So, I want to get out there. I'm not done in his life and said, "Well, what about our travel? I want to take three or four months and go to Paris." And we're like, you know, collision, right? So, we have to get that all defined and agree to up front, so you have a unified and signed off a line plan for the people that are going to be impacted by the client's road map. And then...

We had a life transition expert on the show a while back, and she discussed what a transition looks like from having a beginning, then having an unknown period and having an ending to every transition. And the goal, I would believe in working with someone like you, Allan, would be to reduce that unknown period, reduce the amount of time we spend in the unknown and get to the end of that transition, and get on with their lives as quickly as we possibly can in a solidified manner. And I think this speaks to another one of our questions from one of our Weekend Reading subscribers, got a question from Jeff, and I think you can tie that in here. It's really about timing.

Jeff said he's planning on retiring in four to five years, but he's worried that since he currently doesn't have a lot of hobbies, that he's going to be bored after he retires. He says, "Would Allan recommend getting into three or four hobbies or activities now to make the transition smoother? Or is it okay to wait until I retire?" And I think, one, you can speak to that particular question, but I'm also wondering, as you tie this in here with when do people start to work with you? Is it four to five years out? Is it 90 days before retirement? What does this timeline look like? And when do they start incorporating some of these things in here? And you know what? Maybe Jeff shouldn't have any hobbies if he doesn't have hobbies.

Allan Milham: Yeah, well, so let's unpack that. So, first of all, the reason I love coaching so much is that, let's go do the work and then get on with your life. I'm not a big fan of handholding for years. So, this is a 90-day process, and if you want to come back for some tuneup, you can, but I'm a real believer, as I mentioned earlier, we don't know a lot of time, so we've got to get that transition right and do it quickly, but do it carefully. I mean, we can't rush the discovery process because whatever comes out of that is going to be the seeds of where you're going. So, we can't short circuit that upfront phase because we need to get the best stuff to ensure it's authentic, it's real, it matters, but once we've got those components, wow, now, we can accelerate.

So, for him, normally, we love getting people who are like six months out. And the reason for that is that unfortunately, a lot of people who leave their work report that it was not an elegant dance. It was sloppy. It didn't feel clean. They said that the management, one research said, and I get this for you, that they just said, a large percentage of people who retired just said, I didn't feel supported. And psychologically, we want to get ahead of the game. So, if we can be working with you to give you, we're not with you for the six months, but we're starting just to get you into that mindset so you have time, and then we sort of co-create to say, well, when do you want to go into phase one?

For a lot of people, they want to know what do I need to be mindful of? How do I close out my career? How do I leverage the network? Or what do I do about that for those I want to take with? So, there are some very specific things that we want to grab hold of, and then once they're done, that's really where we come in because it takes time to figure this all out. And if they're working full time, there's just not that much capacity. And for some people, they need a break. They actually need to take a little mini-sabbatical. Others are good if they don't.

Casey Weade: They don't have the mindspace for it.

Allan Milham: Yeah, exactly.

Casey Weade: If you find the individuals that are four to five years out, they're just not there yet. It's not really enough to have a good conversation.

Allan Milham: That's correct.

Casey Weade: Maybe that's the case.

Allan Milham: But there are some inquiries that you can be within that four to five years just to be curious as you move closer and closer, right? And so, we can set those inquiries for them to just ponder so that when they get up to that point, they've done the pre-work and they're good to go. And then it's just a matter of, as I said, once we've gone through the reflective process, then we can accelerate. Now, hobbies, as far as I know, there's no universal statistical response I can give you on that. Some people are motivated to do stuff. Others are like, whatever. Unfortunately, on the bummer side, is I can't remember the number of hours, people, I think there's a report that came out that average American retirees watch 48 hours of television a week. That's not good news for this narrative.

So, if we're talking about individuals that have been all in with their work, we need to move them into the possibility of thinking to say, well, just imagine that you had time to do something else, what would that look like? Are you an adventurer? Are you a reader? Are you team-based? Are you a soloist? And just to be curious intuitively, to be able to say, what would I like to do with the time that could be purposeful, productive in a positive way? Then I would invite that for him, right? And I don't know how much time he has right now free to begin engaging with hobbies but trust the intuition.

One piece we've not talked about, which is really critical, is the mindset. And really the mindset, Casey, sits on top of that positivity, productivity, and purpose. And it's really for him to look at the mindset and ask if I wanted to upgrade my operating state, if I wanted to upgrade sort of how I'm holding my future, what would that look like for him? What would you want to choose?

Casey Weade: Guessing for those that you work with, those that have little to no hobbies currently, I would imagine those are the ones that typically continue to work, maybe in a different capacity. Those that have a lot of hobbies, they probably really enjoy more of a traditional retirement.

Allan Milham: Correct, because they'd already been in it. They know what it means to have sort of a decent work-life integration and they've invested in time to do those things or with family or with community or travel. So, you're absolutely right. For a lot of folks, they've already figured that out, but for some, they've been all-in with work. And that's the one, or maybe we close on this because there's something very fascinating, which I know one of your former interviewees, which you guys talked about it recently. And it's that fascinating thing that I've observed ever since I was in my 20s when I had the privilege to live abroad when I was in college of this dynamic, when you go to a cocktail party, what is the first thing out of someone's mouth to you? So, what do you?

Casey Weade: What do you do, Allan?

Allan Milham: What do you do? Right. And what struck me back when I was in university is that I lived in the south of France during my junior year, and they didn't ask about my parents' location. They ask about, where are you from? Tell me about your family, what matters. What brought you here? And I was always struck as I got into my 20s and 30s and 40s just to see how prevalent that really is, in America, because other cultures they lead with the humanness of the person in front of them, not the doingness of their work identity. And so, that's a calling for all of us to look at that relationship between the shingle, the title, whatever we do. I love your– I can't remember what it was called, father's first, what was that? You were in something that, I can't remember the name of that group.

Casey Weade: Front Row Dads.

Allan Milham: Front Row Dads. Yeah, that was such a game-changer for me to hear because literally, if we could just take that concept out for your generation, it would change the narrative of this whole thing around our doingness and our attraction to the titles and compensation and what our work is. And back to my dear friends, Betsy and Larry, who just stand up, and they don't sit because if they got that doing thing coming at them, they're out of there. So, it's important for us to look at that. And I'm excited for what you do at your age because you got it right. And I wished I had you as a dad. I had an absentee father and he died early when I was a teenager. And the guidance, and when you ask about the boomers still being there and bringing in your first boomer in your company, that's cool because you're now integrating generations to make your organization that much more special and exciting.

Casey Weade: It's so kind of you to say that, Allan. On this elevator speech piece, I guess, it throws me off, and I think about having an elevator speech in retirement is, I'm at that stage and I've been in it so long where, in our working life, you have to have an elevator speech. Why do you put together an elevator speech? Well, so that you can get business, right? So, you can pay a price, or maybe you get a new job someday. You have to have this really refined elevator speech, which I always found extremely annoying in the first place. It just seems so ingenuine to put together one of these elevator speeches.

Allan Milham: That's right.

Casey Weade: How does that apply in retirement? Someone asks you what you do. What is the goal behind crafting this elevator speech? Is it for you? Is it for them? What's the goal, because the goal has shifted, right?

Allan Milham: The goal has shifted. And when you get to the third act of life, if I'm meeting someone and that we get in this conversation about their family and their travel and then we start playing off each other because I've been there. I've been there. It was a fascinating experience when I had the chance to be in London. And you start a new conversation that has nothing to do with work. And what happens is now, there's a connection forming because it's sort of like, oh, my gosh, I feel like your brother from a different mother. And so, notice how you can generate and be in conversation with no need, and we have to call it, we all come with ego, but what we're noticing in the third act of life is the more fragile ego is the one that's going to live more on their accomplishments of the past. And the more stable ego, much like what we were talking about, the learner leader versus the nowhere leader has the ability just to say, you know what? I see you. And I would enjoy just to have a cup of coffee and get out of the sales mode. I appreciate it, Casey. We all have done our 90-second scripts, but the script I'm talking about for the third act of life is a script that's authentic, it's real, it's engaging. And people want to be in conversation with that. They want to lean in. And that's where new friendships emerge from when you just bring your full self there versus your old career self there.

Casey Weade: I can see massive value in that for anyone. It's just relationship building, right?

Allan Milham: 100%.

Casey Weade: And you can't build relationships off of incentives that are placed in the wrong location.

Allan Milham: That's correct.

Casey Weade: Your incentive here, especially in retirement, is to develop a new friend, make a new friend, and then you've really crafted the right elevator speech around.

Allan Milham: That's correct.

Casey Weade: So, Allan, I can't wait to see the impact that you continue to make with this generation. I look forward to talking again in the future. Thanks so much for joining us on the show.

Allan Milham: Thank you. It's been a real pleasure.