This week on YAFPNW, we welcomed back Roger Whitney, CFP® and award-winning podcaster. The last time we spoke to Roger was on Episode 2 of YAFPNW… four years ago! Time flies, doesn’t it?

Funnily enough, that’s a big part of what Roger and I discuss in our latest episode: time. As a financial planner who serves retirees, Roger has a unique perspective on the planning process. He dives deep into the three phases of his retirement planning experience, as well as the Retirement Answer Man podcast and his membership community, Rock Retirement Club.

What people really want out of retirement

After 300 podcast episodes of the Retirement Answer Man, Roger has learned quite a bit about his clients, retirees in particular. One of his biggest discoveries was how people approach retirement. Roger likened retirement to a release valve. Daily work stress, a hectic commute, meetings, traveling for the job: all this builds up pressure. Our culture and marketing (as well as our profession) make retirement out to be a goal that will release all of that pressure. But it doesn’t. It may be because people don’t spend enough time thinking about what they really want out of retirement.

What do people really want? It’s not so much the absence of work. “They just want more control over their time and freedom to pursue things that they enjoy,” Roger said. “Rather than retirement being like a light switch that you turn on or off, work or no work, most people would prefer to have more of a dimmer switch, to slow down their pace and do work that they love a little bit more, but have some time freedom.” 

Discovering this has influenced Roger’s planning and how he talks to his clients about retirement. He’s even taken the advice to heart, swapping a 9 to 5 career for working remotely, more freedom to spend time as he likes, and more control over his life.

The “bling of planning”

Roger likes to view financial planning as project management. The relationship between financial planner and client is a collaboration, not a delegation. By setting that expectation for the relationship first, Roger is able to help clients figure out what they want and how they can achieve those goals together.

Optimization is the “bling of planning” as Roger called it: it’s the fancy and fun part of financial planning. This part involves setting goals, called SMART sprints, for his clients to reach. They’re not limited to financial goals, either. Roger shared the experience of a retiree client who was able to enjoy traveling, but didn’t have many people to talk to when he was home. Roger set a goal for this client to build a social network slowly by participating in local community events. This kind of work, Roger said, is the one of the only ways planners will thrive in the future. Anyone can handle the financial side, but if you’re not adding value in other ways for your clients, you’ll become irrelevant.

Podcasts and the Rock Retirement Club

Roger himself is a great example of evolving as a financial planner and offering clients value that they can’t get elsewhere. In addition to his long-running The Retirement Answer Man podcast, he founded the online community, Rock Retirement Club. Members of the club receive resources and tools for financial planning, as well as the support and engagement from other like-minded people who want to plan for retirement on their own.

And to better his practice even more, Roger recently started another podcast called The Agile Financial Planner. (“Because I don’t have enough to do,” he quipped.) Starting this podcast and talking about his agile financial planning process has helped him tweak his tools and processes. 

The financial planning profession is a hard journey for everyone, especially those who are newbies. That’s why it’s important to always be learning and evolving, to add value to yourself as a financial planner. And remember that the journey takes awhile, “a lot longer than you think it’s going to take,” said Roger. Surround yourself with people that you want to be like, grow your network, and you’ll have a better chance of finding career opportunities down the road.



[tweet_box design=”box_10″ url=”” float=”none” excerpt=”For us as planners, this is one of the only ways we’re going to hold our relevance and thrive in the 21st century. The financial stuff is table stakes…If we’re not adding value, substantial value, over that, we’re done. – @Roger_whitney on #YAFPNW”]For us as planners, this is one of the only ways we’re going to hold our relevance and thrive in the 21st century. The financial stuff is table stakes…If we’re not adding value, substantial value, over that, we’re done. – @Roger_whitney on #YAFPNW 198[/tweet_box]


What You’ll Learn:

  • What Roger has learned about clients through podcasting
  • Roger’s views on the evolution of the financial planning process
  • The first phase of the retirement planning experience
  • Optimization, or the “bling of planning”
  • How client decisions change over time
  • What it means to deliver the “wham”
  • All about Roger’s podcasts and retirement club
  • Roger’s advice for those new to the profession


Show Notes:

In this episode of YAFPNW, Hannah Moore, CFP® and Roger Whitney, CFP® talk about:

Want to keep up with Roger on social media? Follow him on LinkedIn and on Twitter at @Roger_whitney.


[show_more more=”Show Transcript” less=”Hide Transcript”]

Episode Transcript

Hannah: Well, thanks for joining us today, Roger.

Roger: I am excited to be here.

Hannah: So for the listeners who may have just joined in the last, I don’t know, 190 episodes, you were actually episode number two on this podcast. So it is so fun to have you back and kind of see how your story has evolved since we had last spoken.

Roger: Well I sure hope it has, otherwise I’ve sort of been stuck in time.

Hannah: Oh my goodness. So episode two, you were the Retirement Answer Man. And you had… I mean it was quite a few episodes back then, but tell me how has that grown over the last three or four years?

Roger: So yeah, the Retirement Answer Man podcasts, we’re in episode, we just hit 300, so we’re 300 and something and that’s a weekly show. We’ve never missed a week, which I’m proud of. So how has it grown? Well, it’s probably 10, 20 times in terms of listenership. From a financial planning firm perspective, it’s totally changed my life. We have a Rock Retirement Club, which is an educational site with over 300 members of it. It’s pretty much changed my entire life since we’ve last talked.

Hannah: Okay. So tell me about that. So you started serving retirees, especially as planners, we like to think we know our clients, but I feel like when I think of you and kind of what you’ve been doing in your space, I feel like you’ve really gotten to know the clients and the people in this space. So how has your perspective of retirees and what they’ve needed changed and evolved, and how have you changed your practice to serve them better?

Roger: I think that’s what the podcast has accomplished, unintentionally. So when I started the podcast, it was, I’m working with people with similar issues, I think out loud, so I’ll just start a podcast to teach what I’m thinking about which will clarify my thinking to serve my clients. So, that was the impetus of the whole exercise, plus some self-discovery. But what I found was the more that I focused on people over 50, that are either on the approach to landing in “retirement” or landing and trying to manage this major life change, the more that I focused on that publicly, the more I gathered people that were dealing with the exact same issues because they were searching out wisdom on those issues.

Roger: And by creating feedback loops for them to be able to communicate with me, they actually informed me as a group more about my clients, which has been just this beautiful, I call it a virtuous circle. So when we survey or we have meetups with people that listen to the show, they are telling me in their own words what they’re thinking about, what they’re worried about, what they’re excited about, and that is exactly the same things my clients are. So it’s helped me up my game as a planner. So, probably one of the biggest insights, is that we think of retirement as this goal. And our industry definitely focuses on retirement, this word, and most people are running away from the hectic work life that they have and they’ve latched onto this word retirement as sort of the savior to release the pressure from their commute and their drive and the meetings and the travel and everything else.

Roger: And so they’re running away from all of that pressure and they see retirement, and the brochures sort of make it look this way, is that that’s the release valve. And what ends up happening is most people get to retirement and they think they’re going to release the pressure and they really didn’t spend much time thinking about where they were actually going. What I’ve learned is most people don’t, “Want to not work, want to retire.” It’s not the absence of work that I’ve learned, it’s they just want more control over their time and freedom to pursue things that they enjoy. So it’s not the absence of work. So rather than retirement being like a light switch that you turn on or off, work or no work, most people would prefer to have more of a dimmer switch, to slow down their pace and do work that they love a little bit more, but have some time freedom. So that’s probably the biggest lesson that I’ve learned from talking with literally thousands of people over the years.

Hannah: So how has that influenced your planning and how you even just talk to your clients about retirement?

Roger: Well, one is helping them acknowledge that if it’s true for them, because some people just want to retire and that’s cool. But helping them understand that it’s not a race to a destination like climbing Mount Everest and then you reach retirement and all life is happy. It’s really about how do you have a more balanced journey because there are a lot of competing interests that people intuitively get that they don’t really outwardly talk about. One is they want to have a great life today. I mean, you’re young, I’m 53. I want to have a great life today and I’m doing my best to have that.

Roger: But I also want to be okay and have a great life when I’m 80, or when I’m 60 or 70, and those are always at odds with each other. Because in order to have more later, I might have to sacrifice more now. The message with financial planning has generally been sacrifice, sacrifice, sacrifice. You’ll be in the hot tub on the brochure later on in life. That’s not balanced. So, a lot of it is helping people think through all the in between of how they can create a life that’s more structured around what they want, not just now, but for the future.

Roger: I’ve sort of done that for myself in my journey, since you and I last talked. The last time we talked, I worked in a downtown office. I had partners, I was a Chief Compliance Officer, I had lots of responsibilities, I had my nine to five. Now I work mainly out of my house. I have total time freedom. This year my wife and I are going to Colorado for five weeks and I’ll work from there. We did it last year. So I probably work a lot more than I did in that nine to five, but I control my time and when I actually do it, which feels like freedom. What I helped them figure out is where can we find more elegant solutions than just simply saving more to get to that big R.

Hannah: I love talking to planners like you because you’ve been around for several decades at this point.

Roger: Be careful there.

Hannah: I know, I was trying to word that right. How have you seen the financial planning process evolve with how you work with clients? I mean, we talk about the six step and now it’s a seven step process. How do you see that playing out in practice?

Roger: Here’s my view on the financial planning process, and I used to teach the retirement planning segment for the CFP Certificate Program at the University of Texas Arlington here. The way I look at it is I’m going to pivot to project management methodologies because this is a passion of mine and software used to be developed in what was called a waterfall methodology, which I equate to the traditional financial planning process, which is you gather massive amounts of data, you set big audacious goals way off into what you want the ideal product to look like and then you create this big project or financial plan all at once. Then you present your product to the market, you present your plan to the client in Lord knows how many hour meetings of sitting through all the slides. That is how traditional planning was generally developed, was it was a product, here is your plan in your beautiful binder.

Roger: And that is basically how it has been practiced and it’s been evolving, but how we teach financial planning has not been evolving, in that, that waterfall technology or methodology that creates these big massive projects, there’s a big problem with them and you’re probably too young Hannah. But, this is what resulted if you bought Microsoft Office, you would get 20 CD ROMs and you would sit there for hours while it loaded onto your computer and as soon as it started working it was outdated or bloated with way too much than what people needed. That’s how I sort of equate traditional financial planning. I think it has evolved in practice with many advisors even though it’s still taught that way.

Roger: I equate modern financial planning akin to what happens on your smartphone, where you have these applications, where first they ship and they’re a minimal viable product, and then they update. You always have to update your apps on your phone or on your computer nowadays. That’s because they were developed using something called agile methodology, which is much more lean and focused on lots of iteration, prioritization, creativity and problem solving. So rather than try to get bogged down in creating this massive plan, it focuses on just trying to have lots of little wins. And so what I’ve coined is the new style of planning, which a lot of us knew, we just don’t have verbiage around, it is agile financial planning. I do agile retirement management, which is basically taking that very iterative process and working with clients, being more life coach, financial coach and financial advisor, and thinking of it as a project management exercise rather than this big plan I have to do before we get to the assets.

Hannah: I love that what you’re saying. So my next question is, when somebody who’s been listening to your podcast and comes to you and says, “Hey, I need help with retirement planning,” what does that process look like? What is that experience for that client?

Roger: So the first things I make sure they understand is I tell them that what we’re doing is a project management exercise. I tell them that this is a collaboration, not a delegation, meaning that I am the project manager and I have worked on countless projects that are very similar to yours, but you’re not just going to give me everything and I’m going to figure it out. We’re going to figure it out together because they are the expert in their life and all the backstory and what they actually care about. And that’s a little bit of a shift then what they typically hear because if you talk to a normal advisor, they generally want someone that delegates. Then they just show up and present how they’ve done in the market. So, that’s the first thing I make sure that they want.

Roger: So on my end, we make sure there’s a good fit. And so the way that we start the process is we first said, what do we want to accomplish over the next six months? Basic triage. What is it that sparked you into action to even want to engage me? And let’s set a benchmark of what would be a good job six to 12 months from now? A lot of times that will be, well I have to figure out what to do with my pension. I need to figure out how I’m going to pay for retirement. I need to figure out whether to buy or sell this house. There are a lot of things like that. Every client will be different.

Roger: Then what I do is we take that as a benchmark and then I walk them through, okay, first let’s set up the project. Setting up the project, and I specialize in retirement, and this would be a little bit different if you’re far away from retirement, is we start off with what I call the feasibility phase, and that is let’s dream really big about the kind of life you want to have in retirement. I challenge them to dream bigger than they are typically are comfortable with in terms of what they want for basic lifestyle, what they want for the spice of life, whether that’s travel or toys or gifting or whatever.

Roger: Then once they dream up this ideal retirement, then we organize what they’re… The resources are to cover that retirement. So we have three sources of capital you can cover retirement. Right? We have social capital, which is like social security and pensions and things like that. We have human capital, which is probably our most valuable asset, our ability to earn some kind of income if we choose to. And then we have our financial capital, what most planners think about, your net worth statement. And then we organize all of that and then we run a feasibility analysis to see if it’s possible. My goal is that the first iteration is not feasible. My goal with clients is that the first time we test this, I’m sorry you can’t do that.

Roger: And the reason is that I want them to tease out as much of what they can dream of on the front end because well, it’s human nature. We can’t get everything, but if we can tease it all out, at least we’re not ignoring it and not even putting it on the table. Because once we do that and we know it’s not feasible, then we work through, I help them negotiate with themselves on what they have to give in order to get things that might be deal killers to them. It’s actually a beautiful process because every client is going to focus on certain things. A good example that is not typical is a client where he was in such a pressure cooker job that his health was literally at risk, but he was the breadwinner, and he was in his early 50’s, and the solution ended up being after, it actually it took a lot longer than normal, that he needed to quit his job and take a year off because his health was literally at risk.

Roger: Then with the understanding that he had to go back to work at some point. He wasn’t quite sure what he would go back to work to, but the solution ended up being that he leave work, take a sabbatical and then regroup and have a mini project to figure out what he will do next. But first get himself in a mental and physical position where he could work. That’s not a typical solution, but for him it was essential because of the personal situation that they were going through. So, that was his deal killer. He needed release away so he could make rational decisions. But every person is going to be different. I talk a lot. That’s the first phase of the project. But then we go on from there. But I don’t want to just sit here and ramble.

Hannah: No, no, no, this is great. I’m so curious. So you kind of come in and you triage the client and say, “What’s most pressing?” And I’m sure in your expertise you’ll be able to identify if they don’t recognize a very pressing issue. Do you continue on? Is it an ongoing relationship? It’s been interesting, I’ve been hearing a lot of people, and I say it on my website too, is we want lifelong lifetime relationships with clients. Is that something that you shoot for or do you expect clients to come and go?

Roger: Yeah, we walk life with people. We’ve experimented with flat fee planning and limited term engagements and one, they’re nowhere near as fulfilling or impactful for either party and two, from a time perspective, it’s too much time for a short term engagement. But if you have the time, if you have some time, I think it’s a worthwhile thing doing. It’s a matter of managing your time via the opportunities that you have coming in front of you. But we just walk life with clients. So for your question, the rhythm with a client is, so we go through this process of feasibility, then we do sustainability and then we do optimization. And so feasibility, let’s get to something that’s possible. Let’s make it sustainable by doing cashflow planning to make sure we don’t get veered off course.

Roger: Then optimization is what I call the bling of planning. That’s generally of what everybody focuses on, right? That’s what we write articles on is all the blingy stuff. Typically all the blingy stuff is not going to be life changing, but it’s fancy and it’s fun to talk about. So, that’s usually where people want to start. And so what we do with clients is we bring them through every meeting. We go through re-evaluating the project to see what’s changed in their life and what’s changed financially, but at the end of every meeting we set what’s called a SMART sprint. SMART is an acronym for goal setting; specific, measurable, actionable, realistic, time-bound. And then we set a sprint, generally it’s going to be 90 to 180 days. Then generally we’ll have two or three sprints at the end of every meeting, and we are very specific of, okay, we agreed that you are going to do ABC by this date, I’m going to do ABC by this date. And maybe there’s some things that we’re collaborating with together.

Roger: The idea around that is I’m much more focused on having lots of wins. I’d rather have less action in one win and lots of action and have our efforts spread and not really get anything accomplished. So a good example of some smart sprints would be building an income floor to plan out how you’re going to pay for the first five years of your life. That’s a very detailed thing, geeky thing that usually is in my boat to come up with that first draft so we can get very detailed financial stuff. But we’ve also had smart sprints, one example is, and it’s not unusual, a client who traveled so much that he had lots of work friends, but if he was home, he wouldn’t have anybody to go out to have a beer with.

Roger: And he was getting ready to retire. So he was about to lose his entire social network. So a smart sprint for him was, okay, in the next 90 days, find one activity you can do locally to try to meet somebody and slowly build this social network, whether it was church or a game night or whatever, start to build that social network. So we do a lot of hard and soft things because the goal is for them to create the best life they can. So we ended up getting into a lot of softer things too. But the key for us in the process, it’s setting these SMART sprints and then just focus on getting those done and then reassessing and setting new SMART sprints and iterating from there.

Hannah: I really like that approach and it just makes a lot of sense. One of the other things that came to mind as you were talking about it is I love how helping somebody find a social life when they retire is part of financial planning. Even though that’s not tied necessarily to the numbers.

Roger: For us as planners, this is one of the only ways we’re going to hold our relevance and thrive in the 21st century. The financial stuff is table stakes. Anybody needs to know that. I mean Vanguard set the bar, it’s 30 basis points for a CFP and asset management. That’s the bar. If we’re not adding value, substantial value, over that we’re done. So it’s, I think, a call for financial planners, and I think a lot of people are answering it in adding value in a lot of different ways than just simply asset allocation, doing the financial plan and looking at disability insurance.

Hannah: We talk about the value that we add as financial planners and you gave a great example of helping find a social life once they retire, but once they have that social life, are there still places where they’re going to come back to you? What does that look like 10, 20 years into their retirement?

Roger: Well, I think every person’s going to be different, right? Some people are going to be able to self manage ultimately. But I think all the decisions that we make about how we want our life to look like, how we allocate our financial resources, all of the decisions we make, deteriorate over time at different rates. So, I think a lot of clients are going to need to re-up because life changes. I mean I’ve been married 30 years this years, I’ve been married to like three or four different women. She’s just a different version of herself. She keeps changing on me. So I have to keep evolving because I’m changing as well. And so we got to make sure we’re walking hand in hand. So there’s lots of little conversations that go on.

Roger: Absent the kind of things I’m talking about, I don’t know if we will be relevant if it’s just about the money. I think of it this way. I call it the wham and I didn’t even mean to make it up, but I like it now. What people generally want is the wham. They want to know what should I be thinking about? What risks am I forgetting about? What opportunities could I take advantage of? The what. What should I do next is generally what a client wants to know, and that’s a little bit of what agile solves. Once they have the what, then the next is H, how do I do it? How do we go about figuring out that issue, whether it’s longterm care or finding friends or my wife is sick. How do we go about navigating this?

Roger: Then they want the A, they want some action and accountability because humans, they’re not into this stuff. They go about their lives and will get motivated and then that motivation will wane. So we need some accountability and actions so we can actually accomplish things. That gives momentum. And momentum is a beautiful thing in financial planning, and I think something that’s missing a lot of times. Because momentum, this is a very weird world for a normal person. Money’s weird. Talking about money is weird. It’s sort of, I don’t understand all those crazy terms and sometimes we don’t help in that. So if we can have a wham where we create lots of little wins, that’s going to build confidence, that’s going to build agency and that’s going to build, okay, what do I do next?

Roger: I think that’s what our role is, is to deliver the wham, what do they do next? And that is something that’s for a lot of people, life is always changing. Do I buy this house or do I buy that house? Do I build this deck or do I not? There are numerous decisions that come up that they need help in decision making, not simply from the spreadsheet perspective. So I think where we’ll be relevant is in being the project manager and keeping the win streak going and then two, really helping them make decisions. So we’re going to have to become much better at decision making, not just simply financial management. And I think that’s how we keep our relevance.

Hannah: So you have the podcast that you started, your 300 some episodes into it, you have your traditional financial planning practice. What else are you doing? I know you mentioned a community.

Roger: This is all a result of the podcast, and the journey that it’s led me on. There was no grand plan. I just iterated and just kept leaning into it as I felt this was where I was supposed to be going. So we have a podcast where we try to… I think of it as virtual circles. We have the podcast where we tried to just serve the world and hopefully speak something that resonates to a certain part of it and help them have better lives. And then we work with around 80 or so clients where we walk life with them and implement this process, and help them in all of this decision making. We call it walking life with clients because we try it too, and then we have, as a result of the podcast, we have an online community called the Rock Retirement Club, because are a lot of people, they don’t want to work with an advisor. They would prefer to do all this themselves. And the hard part for them is generally speaking, there’s no safe place to get education because most education is, it’s like the internet, it’s basically one big infomercial.

Roger: It’s hard to find a safe place to get really world-class education, in my case, on retirement, when there’s no sales pitch on the other end. So the Rock Retirement Club, our goal is to provide that education, but also to gather people that have the same spirit so they can talk to each other about all the different things that they’re dealing with together. And that’s ended up, we have over 300 people in there and it’s been a beautiful thing. Then I just recently started a podcast called The Agile Financial Planner because I don’t have enough to do.

Hannah: I understand.

Roger: As I’ve evolved this agile financial planning process, starting the podcast and talking about how we do it is teaching me to solidify the processes and the tools. So it’s making my practice better and hopefully putting a framework out to what I think a lot of people are doing already, but giving them a framework in a verbiage to adapt as they see fit or adopt as they see fit. So, that’s what I’m doing.

Hannah: Rock Retirement Club, is that a paid a membership or is that just like a free Facebook group?

Roger: Yeah, so it’s a paid membership. It’s $500 a year and the motto is walk with the wise and become wise. And what we attempt to deliver is world class education tools to take action on the education and then inspiration from walking with like minded people with the same spirit and to be able to have a safe place to ask a question and get an answer without all the craziness of the internet.

Hannah: You don’t want your friends and family maybe to know your questions.

Roger: Yeah. That’s interesting. It’s sort of that airplane effect isn’t it? Someone will share a lot of financial information to get feedback, but not with their family, but they will with people that they don’t and that are… And the nice thing with the club is, and we really don’t market it outside of the podcast, is my podcast serves as the natural filter. So I remember when I was starting it or getting ready to start it, we did a survey of the podcast listeners, seeing would you want something like this? Because we had been asked for it. We got about 800 responses. That gave me a lot of data, but what I did was I said, oh, I need to talk to some people and what would they want, what wouldn’t they want and so forth. And so our team set up and it ended up being like 70 calls in two days. It was a marathon.


I got the answers of what they would want, what they wouldn’t want, which was helpful. But you know what was the most impactful Hannah?

Hannah: What?

Roger: It was pretty moving because everybody, they were in the same spot of life, they were generally self-made, they were very wicked smart in various different ways, they lived all over, but they all had the same spirit and they were all solution-oriented, helpful and they were all really, really nice. It was a constant, wow, these people would love each other. And I think the podcast is a good filter for that because the people that listen that would be interested, they resonate with me in some way. And the people that think I’m an idiot go away. And I think that’s perfect. And so it’s a very homogeneous group, which is if you can walk with wise people with the right spirit, really powerful things can happen. So, it was a pretty moving actually.

Hannah: So what’s next for you?

Roger: I’m building out the retirement masterclass in the club, which will be all the education that people need to really rock retirement from the softer side and the money side. I’m going to continue to work with clients and walk life with them. Then I want to help promote this idea of agile financial planning to help the industry evolve so the right people can thrive going forward. I think that’s going to be the way that we plant our flag in what we offer clients that technology can’t.

Hannah: What would be your advice to somebody who is just starting into the financial planning profession right now?

Roger: It’s a hard journey you’re on. Right? Because we’re in the middle innings of transitioning from a sales profession to a true profession, a counselor profession. A lot of newer planners, and I see this in the XY community a lot, is in general they’re wicked smart, very competent, great service heart, but there’s not a lot of career paths for you other than a sales path. I think my suggestion would be, is realize it’s going to take a lot longer than you think it’s going to take, and start to surround yourself with people that you want to be like. If you can find an organization where you can come on in a role where you have a career path where you don’t have to sell, I think that’s where the future is going to be.

Roger: There’s going to be less firms that are less sales oriented, but have true career paths where people can actually just practice their craft. Because generally the best planners are not necessarily the best marketers. Those people need homes because we need them. So it’s going to be about who you know and the network that you have so you can find those opportunities, whether it’s with a small firm like mine or yours where you can come on because the firms that have the clients are dying for help. But it’s a hard journey. I don’t necessarily have the answer.

Hannah: Well, great stuff. Well, thank you for being with us today, Roger.

Roger: You bet. Hopefully 200 episodes from now, we’ll talk again.