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Casey Weade: Replace Yourself, Retire With Purpose & Scheduling Priorities

My guest is a certified financial planner, a retirement planning professional and a best-selling author. He has been a sought-after speaker on progressive personal finance and retirement planning strategies.

He hosts the Retire with Purpose podcast, television and radio show. In addition, he's been featured in national media outlets such as The Wall Street Journal, USA Today and CNBC.

Our special guest is Casey Weade.

In this show, we’ve got a little smorgasbord of topics for you. Let me give you a little insight. Originally, I was thinking this was going to be straight up all personal finance, money, retirement and investing and it is with something more.

We talked about how to replace you, a little nod to my entrepreneurs out there. We also talked about retiring with purpose. What is that exactly mean and why you want to build your retirement strategy around that?

We also talked about the scheduling of priorities. If you want to get something done, you want to hear what Casey has to share with us here. We also get into challenging the 4% rule, what the single best investing/retirement strategy is for you. You want to hear that strategy.

With that said, let’s get to it.

Dustin
Casey, prior to your youngest son's birth, you discover that he had a condition called CDH, that's Congenital Diaphragmatic Hernia, which came with a small chance of survival. I can’t imagine getting news like this. Take us back to what was going on in your world and how this unfolded for you.
Casey
Life was pretty intense at the time. I was working a lot of hours. I was in that stage of my entrepreneurship career, which was 60, 80 hours a week. Go as hard as you possibly can go. My wife was pregnant. We're ready for this second little guy to come along. We go into the doctor's office. She's getting her ultrasound. They're not saying anything. It's dead silence. I'm trying to figure out, “There must be a problem.” They walked out of the room, left us in there. They came back in and said, “We want you to go across the street to the high-risk doctor.” At that moment, I knew something was wrong. We walked in. He shared with us the bad news. It was tough to hear that he had a slim chance of survival.
It was positive to know that if we relocated to Cincinnati, which was about four hours away from our home base, if we relocated down there and I would have to be relocated down there and not back home for an extended period of time, at least three months. It ended up being six months that I was away from the business. I had never been away from the business or out of the office for more than two weeks my entire life. I've got to be gone for like 3, 6 months, maybe more. It could have been a year or more. I ended up being about six months. It was a life-changing experience for our whole family. I would say it probably had the biggest impact on me because I was a bit of a workaholic prior.
Dustin
I could relate to the 60 to 80 hours. First, we should take a step back. Will you explain what CDH is? What does that mean to people?
Casey
CDH is a very rare congenital defect. It's Congenital Diaphragmatic Hernia. Essentially, he had a hole in his diaphragm. Your diaphragm separates all of those gut organs from your chest organs. There are different levels of severity. He was on the higher end of the severity spectrum. Those gut organs were born into his chest, suppressing his lungs and heart and some of those vital organs in his chest. When he came out, obviously he's not breathing. His lungs aren't operational. We've got to get in there, patch that hole up, put all the organs back where they belong, and about a dozen operations later, he's doing pretty solid.
Dustin
When you say patch the hole up, is that like taking a tissue or does it naturally grow over time? How does it work?
Casey
They take a piece of Gore-Tex and they sew it in there. You can see your skin, your internal organs. I'm not a physician, but my wife would be able to explain this to you beautifully. She was deep into the details and loves the medical world. If you were to look into your abdomen, you wouldn't be able to see that Gore-Tex patch as it would get covered with essentially skin cells.
Dustin
Originally, the frame of this conversation for me was this is a money conversation. This is about retiring with purpose. That's what you're known for. We'll talk about the book here. You had mentioned something that is near and dear to my heart as a family man. You're working 60, 80 hours. This life incident happens. You've got to move, never having experienced two weeks off from the office. How did you transition? How did you now start to think about business? I want you to frame this, Casey, for that person that maybe is grinding 60, 80 and maybe that life incident is around the corner and they don't know it yet.
Casey
It was a total game-changer for our business. Our business exploded after I left. People always joke about that. I feel like the business needs me. I feel like I need to be there all the time. I had a couple of months in order to prepare. We found out around September. We needed to move in November. I knew I wouldn't be able to get back. I had to put a new CEO in place. I had to put a new HR director in place. I had to structure the business to continue to operate in my absence. I had to replace myself in like 60 days. Usually, people will try to replace themselves for over six years, not 60 days. It was a mad rush, training and getting everybody ready.
I took off. I had this, “Casey is going to live off in the Bahamas for the next six months.” The team may not have pulled together quite as they did in this scenario, but they did. They all got behind me. In that first quarter that I was out of the office, the business grew 50%. It was this realization to me that the business doesn't require me to be there every single day, all day. I don't have to be the first one to get to the office and the last one to leave. My thought process was always, “I've got to set this example. I've got to be the one that's working harder than anybody else if I want them to work hard.” I was showing them at the same time that they didn't have to have a life. I wasn't showing them the full spectrum of what life should be. Being down there and that environment for me made me realize I didn't have to be in the office 80 hours a week. It also made me recognize what's important in my life and how much I did enjoy working at the same time.
Dustin
Your son is doing amazing. He's thriving now. You had mentioned the last operation.
Casey
The last operation was this past fall and he's doing amazing. This is one of those things where you never know if it's going to come back. He could have complications down the road. It could be a year from now, it could be 50 years from now. For right now, he's doing well.
Dustin
This is why we do this to ask that question. That was a huge lesson replacing yourself in 60 days for that business owner.
Casey
As part of that, sometimes our businesses as an entrepreneur, they need us to leave. They need us to get out of the office and stop bogging them down. That's what I've started to do. I'm scheduled around three months out of the office a year. I do that strategically to give the team some time to breathe because when I'm in here, I am ready to go. I'm going 120 miles an hour and I am ready to implement new things, get the ball rolling, grow and get better. Sometimes they need a little time to catch up before Casey's back in the office.
Dustin
I lead with this question, Casey, as I was telling you beforehand, some personal question because a lot of us can relate, maybe not necessarily to this particular situation. We've all had something happen or some of us are about to have something happen. I like to think that we're putting people in a position mentally for what life throws out because that's the game of life. Another side of this is being in a position financially. I want to get to that. I want to talk about that because it's one thing mentally to have it. You were fortunate you had a business and you had a team around you. It's about being ready financially. You talk a lot about money. You talk a lot about retiring with purpose. I'm curious as to what you mean by retire with purpose.
Casey
A lot of that comes out of that experience that I had with our son. You don't usually get the experience of retirement until you are retiring and then it's almost too late. Most people when they're retiring, they're not business owners. Most people that are retiring, they worked in a job for 30 or 40 years and now they're transitioning to 30 or 40 years of retirement. They don't get the opportunity to step away from work for 6 months, 1 year or 18 months and see what that truly feels like. That's one of the things that I teach I the people that we're working with is to take some time and get a feel for retirement. Test the waters out a little bit before you take that dive committee because you might find that you enjoyed your work life or maybe not all of it, but there are certain aspects that you want to continue to carry on with you into retirement.
I know for me, when I first got down to Cincinnati, I'm thinking, “I've got several months off. I'll focus on my family. I'll focus on our son. I'll focus on our other son. I'll focus on my wife. I'll focus on my health. I'll take care of myself.” I quickly realized that I wasn't very happy. My happiness level fell pretty quickly because I didn't have that purpose every single morning. A lot of it was having a schedule. I thought not having a schedule would be fantastic, but not having a schedule was not fantastic. I need a regimen. I needed to have certain aspects of my life that I could focus on during that period of time. That brought me a sense of purpose and fulfilment, things that I enjoyed.
Dr. George Schofield was on my podcast a while back. What he said resonated with me from this experience. He said, “You need to have a lot of ponies on the track and don't let those ponies turn into Clydesdales.” For me, work had turned into a Clydesdale. When I was down there, I said, “Let's get some ponies on the track. I'm going to get back into the gym. I'm going to wake up early. When I wake up at 6:00, from 6:00 to 7:00 I'm going to read, from 7:00 to 8:00 I'm going to work out and from 8:00 to 12:00 I'm going to work on personal development, professional development. I'm going to be in the hospital from 12:00 to 4:00. I'm going to go back. I'm going to make dinner for my wife from 4:00 to 6:00.
I needed that structure and all of those things bring me a lot of happiness. Some people might look at that and go, “He wants to work out. He wants to read. He wants to make dinner for his wife. Those are the things that brought me happiness. It took me sitting down and analysing those things. Trying to not say, “I'm going to work on professional development from 7:00 AM to 7:00 PM.” Let's see if we can find some of those things that I'm passionate about. Inject them into my day, throughout the day, and not let any single one of those things turn into Clydesdales because that's when it becomes a problem in life. If we can constantly think about that, every single day, waking up and thinking about how many ponies do I have on the track? Am I going to ride them all? Is anything turning into a Clydesdale? If it is, I need to reign it back in.
Dustin
There are certain people out there that would love to sit in the hammock. I do get a sense of purpose out of working, creating and developing myself so I can completely relate. I think a lot of people reading this can.
Casey
Not everybody is like that. I can tell you about the extremes. I've got one couple that we've been working with for a number of years. When they came in to visit with us, one was an engineer, one was a nurse and they'd worked in the same places for years on very long hours. He did a lot of travel. She worked a lot of late-night shifts. They had a bunch of kids. They never had the opportunity to spend time with each other. When they step into retirement, their purpose was to make up for a lifetime that they felt like they lost out of time with one another. That's all they wanted. That's all they're doing. They're traveling the country, spending time with their kids, spending time in their faith, getting involved in the church.
They are happier by a gazillion times more than they were when they first came down and visited with us. They were relatively pretty miserable people when we first connected. Now they are the happiest clients we have. At the other end of the spectrum, I've got clients that are worth hundreds of millions of dollars. There's one that is a bit of a mentor of mine. You might've read about him in Job Optional. For him, this is somebody that he said he wants to create. That is his purpose. He wants to live and create. He sold his company for $100 million. He's making a bigger impact in the world than he's ever made before. He's doing the things that he loves to do, but he is more work-related and other ones, more family-related. We're all unique, but we need to determine what that is that drives us.
Dustin
Casey, what's your advice for people that are a few ways from retiring. I'm not saying they're fresh out of school, but to retire with purpose, to ascribe to this, for those that are still working, still doing their thing, not ready to retire yet. What's your advice for them so that they can get to this idea of retiring with purpose?
Casey
I truly believe that where I am at is largely out of this constant goal-setting mentality that I've had ever since I was in elementary school. I know that makes me a weird kid. There are not too many elementary school kids that are writing down their goals and sticking them on their mirror. That's been something ingrained in me by my parents and grandparents. I had some sports psychologists that I worked with when I was younger. That has been something I've done my entire life. Maybe it sounds cliché that you need to set goals, but sometimes we need to get back to the basics. I always thought that was so basic that I didn't teach people that.
When I started working with my team members, the people that are on our team, I'm sitting down with them, going through their goals and having them come into this meeting with me with three personal goals, three professional goals. I had some of them told me they've never set goals in their entire life. I was astonished that it was even a possibility. The people that are reading this right now, they're probably goal-setters. I still want to say I found very successful people that don't set goals. Those goals will drive you towards wherever you want to be, whatever that purpose and passion are. For me, I'm not one of those who says, “You need to write those things down. You need to read them every single morning.” That can be a little discouraging quite honestly. You write those things down and that is a process of self-discovery to help you determine what you value in life and where you want to be in the future. If you're thinking about that, once a year, at a minimum every quarter preferably, that's going to help you get to where you want to be someday in the future.
Dustin
I want you to speak more to that. I completely agree with you that some people don't even know that it's possible. This next segment would be me, which was I wasn't specific enough in my goals. I had set a goal of I to want to write a book this year or I want to make more money this year. Only until now have I set financial goals. Will you speak to the specificity and also financially, what should they be thinking about from like a financial perspective? Should I save X percent of my revenue or income this year? Should I be putting $10,000 a year into retirement? Maybe invest in my first stock? What's the advice you have there?
Casey
This comes back to purpose because there's a huge difference, a vast difference between the traditional retiree that's going to save their entire lives and retire at 60, 70 years old in contrast to the fire movement people that want to create a bunch of streams of passive income. They want to continue to work their entire lives. That's a misnomer this financial independence, retire early. They're still going to work. They're going to do the things they want to do and not spend 40 hours a week on it or whatever it might be. It does come back to purpose. What are you trying to accomplish in your life? Are you trying to retire 40 years from now? Are you trying to grow a business? Are you trying to create other passive income streams? Do you want to spend time with your family? There are people out there that hate work and they don't want to work at all.
They get a lot of benefit out of volunteering and spending time by the pool, spending time with their spouse. There are others that have to be creating something huge in life, in the world and making a big impact on it. Those take different types of financial strategies. For me, if we start at the basics, there are those basics. I know that's probably what you want to start with. For me, it was maxing out my Roth IRA and along came HSA. You had your Roth IRAs. You had your HSAs. Those tax preference accounts are a good place to start, but I would also exercise some caution in that. This was one of the best things my dad ever taught me. I remember that first year I maxed out my Roth IRA, he said, “I expected a pat on the back. Casey, you did a good job-saving. You saved $5,000 in your Roth IRA.” I thought I did such a good job. I've got this money put away for retirement.
He said, “Do you know where the real money is made? Do you know where real wealth comes from?” I said, “Hard work, saving?” He said, “It's not the stock market.” What did you invest in? I wanted to brag about you have this stock or that stock and how good I was at picking these things. He said, “What kind of difference is that going to make in your life?” A lot of us will brag about this stock that made us 20%, which was $100. It doesn't have a long-term impact on our life. The real wealth, he said, is made in business and real estate. This is coming from a financial advisor at the time around 30, 40 years in practice sitting down with thousands of wealthy individuals. Finding that it wasn't the stock market that made any of them rich. People will say, “Warren Buffett got rich investing in the stock market.” He did. He invested in companies. He was a business owner. That's vastly different.
The problem he had with me maxing out my Roth IRA was what if you find a good opportunity that comes along in business or real estate? You need to have that cash available for that. A lot of us listen to the talking heads that tell us to max out our 401(k) start at 10% or start at 5%, increase at 1% every single year and then that great real estate opportunity comes along and you've got to take the 10% penalty from your 401(k). You’ve got to pay taxes on those dollars. You get all these strings attached to the funds and it takes too long to get it and now the opportunity is gone. I would strongly encourage younger savers to make sure they're not putting money in tax preference accounts, put some funds there. They're great things. However, make sure you've got some funds you're setting aside for the real opportunities in life.
Dustin
I'm glad you brought that up. This is a question that we've received and it's this idea of real estate. The question is essentially in one form or fashion is why is a financial planner, someone that is often compensated by the product that they prescribe or they offer, would they be motivated to recommend real estate in a portfolio outside of REIT or stock, a real estate related stock? Why would they recommend to their client to get into real estate? How do they walk that line there?
Casey
It's a difference in the type of individual that you're working with. I have young friends that want to work with me all the time. They'll be in their 20s, 30s, 40s and they'll say, “Casey, I'd like you to manage my investments,” and “What would the goal be in that?” “Can you get better returns than I'm getting?” I'm like, “I don't think so.” I buy the S&P 500 index fund and ride it for the next 20,30, 40 years. Pretty much any mutual fund or financial advisor that's out there, when you're young, your goals should be to keep your expenses as low as possible and maximize growth. If it's all about accumulation, it's all about growth. You don't need a financial advisor for that. Go back to the basics.
Dave Ramsey has got some great basics out there to help you get started. As you accumulate wealth, this natural transition happens where it does make sense to start working with a financial planner. If you're young, you're building a real estate portfolio, you don't need a financial advisor to tell you to do that or how to do that or work with you on that. If it gets to multimillions and billions, you've got a different need. It's not about growth. It's not about getting a bigger return on your investments on those properties. It's about protecting those properties from major financial risks. That's when you pay a financial planner. You pay a financial planner to protect your wealth and not to make wealth. That's the type of individual we're working with.
People that are 55, 65, they're making a transition or retirement; their goals have shifted from accumulation to preservation. It's about protecting my wealth, make it last a lifetime. Those major risks are emergencies, longevity and rising taxes. It could be inflation. It could be major long-term care expenses. It could be legal issues, your liability. That’s where it makes sense to start working with a planner and pay an advisor is not to have them hit home runs, not to have them help you accumulate those assets but to protect those things. That's when I hired my financial planner. It was at a point where I said, “I’ve got a lot of different things going on. I’ve got a lot of different investments, a lot of different portfolios, a lot of different insurance products, a lot of different real estate. I wanted a second set of eyes.”
Dustin
Do you proactively manage your stuff and send it out for that second set of eyes? How does that dynamic work because you know your stuff?
Casey
I don't manage my own investments. I've got third party asset managers who are overseeing those accounts, and that's something that I've transitioned to over the last couple of years because I always love getting in there and making the trades. I started getting further and further away from it. It goes back to what dad always said, “What kind of impact does that making in your life?” It's not making a monumental impact where the impact is happening is in my business and with my family. Those are the things that I should be spending that time on. When it comes to actual management, there's a third-party asset manager that's managing those individual assets because that's all they do all day, every day.
I want them doing those things. I've got a financial planner that's looking over the overall allocation from overseeing the third-party asset managers, making sure the insurance premiums are paid, making sure I have proper coverage, taking a look at my tax returns, seeing if there's anything that I've overlooked, looking at my beneficiaries. I have messed up my beneficiaries so many times. You wouldn't think that would be something that a financial planner would overlook. We all overlook our beneficiaries, especially as we start accumulating more and more stuff, more and more accounts and investment accounts. We need to make sure there are beneficiaries and all those things. It's one of the simplest things to do that's most often overlooked is making sure we have the right beneficiaries in place. It’s having somebody else that can oversee all those things that are going on and I'm still the quarterback.
Dustin
One of the things that popped up for me, you had mentioned FIRE. We've interviewed quite a number of people that are part of that movement that the Financial Independence Retire Early. Most people aren't retiring early because they love what they're doing and they love to contribute. I wanted to ask you, typically we have a conversation, you go from accumulation to preservation and that generally happens for most people, let's say in the working world, not in the FIRE movement when they're later in life. It's not about your age. It's about a number. Is there any hard, fast rule when one ought to be going from accumulation preservation? Is there a number, a rule of thumb or anything like that?
Casey
You've heard it right. The rule of 100, take your age, subtract it from 100. I don't think that applies when you're talking about someone in my situation or someone that's in that FIRE movement, someone that's in their 20s, 30s, 40s. Most of these individuals, they aren't necessarily living off their portfolio. Most of the time they're living off passive income streams from rental properties or royalties and businesses they've invested in and things like that. That comes down to who you are and where you're making your money, how you're creating that income stream. For me, I'm a conservative guy. If you look on an allocation basis, I probably only got about 20% of my portfolio in the stock market and that goes back to where the real money is made.
It's made in businesses, real estate. For me, I'm also still creating a revenue stream for my business. It's okay that I've got these other assets there. I would also throw into that most people don't think of their business as a stock because they go, “I've got control over it.” The reality is it's a very risky investment. You've got all your money in one basket with that business. We don't realize how much risk we're taking on with that. My dad always said, “Do you need to take what you've earned in your business? Set it aside someplace safe. I give you something to fall back on. That's what the mine is there for. I know that worst-case scenario, everything can fall apart. Business can be gone and I've still got funds that I can fall back on that will guarantee my income for the rest of my life. That gives me the ability to take greater risks in my business and leverage that confidence to do things I probably wouldn't do otherwise. If you look at my overall net worth that way, he's got about 90% at risk.
Dustin
Casey, where were you several years ago? I needed you several years ago to have this conversation with me. That's one of the things that I did. I put everything in the business. That's what everyone was saying. I was envisioning some big payday. I made small investments, but I wish I had made smarter money moves. That's why I'm excited to be part of the WealthFit crew is to communicate that message, “It's great to invest in your business. It's great to do the 60 hours open for that payday. At the same time, you should be putting that money elsewhere and diversify.”
Casey
There can't be anything more important than setting yourself a number, knowing what your number is that you have to have. I had a business consultant asked me this question probably a few years ago. We were sitting on my back porch and having a drink. He looks over and says, “Casey, what's your number?” I told him what my number was. What's weird is you'd think a financial advisor would know their number. I don't think most of us ever think about what our number is, especially when we're in our 20s or 30s. We don't think about it. We're trying to get by. He said, “Casey, once you figure out that number, once you achieve that number, you'll be amazed at what changes in your life.” I set a number and I see so many business owners who are pouring everything back into their business and that makes for a pretty uncomfortable life.
For some, it works. For some, you hear the stories of how it works but for most, it doesn't. Most small businesses are going to fail. If you don't have anything to fall back on, all that work was for not. I always worked towards that number, knowing, “I've got to have X amount of dollars.” Maybe for you, it's $1 million or $10 million or $100 million, but you know what you have to save every year to hit that goal. You know what type of return you have to get every year to hit that goal. Once you get there, our business exploded. My happiness, the meaning that I received that every single day had also skyrocketed. We have to get to that number as fast as we possibly can. That's what's happening in the FIRE movement largely is people know their number. They're saving as much as they possibly can every single year to get to that number or they're trying to create passive income streams outside the business to satisfy that number and an income stream instead of a lump sum. There are different ways to get there, but that is what's going to elevate your business.
Dustin
Casey, my journey into the personal finance space has been relatively short in terms of interviewing people and taking a passion and reading it. I'd always want to work on growing the business, marketing and sales. One of the things communicated to me was this idea of that 4% rule. If I've got $1 million, with the 4% rule, I should be able to get a 4% return without touching the principal of that. As a conservative number, is that something that you subscribe to? Is that rough information to get to my number? If I could live, my family could live off of $40,000 a year, I need to get to $1 million because I should be able to get a 4% return without touching anything. What are your thoughts?
Casey
I would exercise caution with that because it wasn't meant to be applied to someone that wasn't living a traditional retirement. The 4% rule was meant to be applied to someone that's going to live a 30-year retirement. This was created by Bill Bengen back in the ‘80s. It evolved into the safe max rule in the 90s. They were using back-tested data on a stock and bond portfolio saying, “If we look back throughout history, we pull 4% out of our investment portfolio every year making annual adjustments for inflation.” They found they had a 95% chance of success. That's over a 30-year time horizon. If you are 40, you might need that to last more like 60 years. Your safe withdrawal rate might've gone from 4% to 8%. There are two major risks facing people that are trying to use that strategy now and that are a stock and bonds strategy.
You've got stocks, which we look at market valuations; put it in one of the most expensive markets in history, which means we should see lower returns moving forward over the next 30 years. We look at the bond portion of that portfolio with interest rates and your all-time lows. One, they're not paying well now. As interest rates rise, your bond valuations are going to fall. This is an interest rate environment we haven't experienced. Factoring those two things in, I would exercise caution with that. I had a great interview on my podcast with Todd Tresidder, who focuses on financial planning for younger generations. It’s an unorthodox way of planning.
If we're a younger individual, we should think about creating those income streams. How are we going to generate that income and make it inflation-adjusted? I am perfectly fine working of a lump sum and saying, “If I need, $100,000 a year, how much do I need to set aside? Maybe I want to set aside $5 million to generate a net, $100,000. We've got to take into consideration taxation or age, how long we want those things to last. I do like Todd's method and this is why I say nobody's method is perfect. I am not arrogant enough to think that I have all of the answers.
You have to find the one that fits right for you. His method that he used was interesting, which was, “Let's focus on the income streams.” If I need $100,000 a year in income, it's not about the number, it's about the income. How do I generate that? Maybe I can generate $100,000 a year in passive income from a $1 million real estate portfolio that's debt-free. You can think about it based on either a lump sum that gives you confidence, which is what I used because I don't want to create the income. I don't want to create unnecessary income that's going to cause more taxation. Give me the lump sum, keep it tax-deferred, make sure I don't have to generate income on those assets, that's going to cause me more taxation than I'm already paying. If I was thinking about it more from a FIRE perspective where I didn't want to work and I did want to live off those income streams, maybe now I'm focusing more on a cashflow basis, if that makes sense.
Dustin
It's funny because you talk about the conundrum of the FIRE. From the outside, often we'll think it's all about retiring early and never working again. For some people, as you said, that is the case. I often find many people either like to start a blog or write a book or get into something or try to monetize it to create that income stream. Fittingly, you wrote a book called Job Optional: The Science of Retiring With Confidence; The Art of Living With Purpose. Casey, why did you write this book?
Casey
For me, it was a large realization that I had a couple of years prior. I have always been a goal-setter. Throughout my entire life, I was checking the boxes. This was a while prior to writing the book, but I had written a couple of other books prior to this. I had gotten much clearer on my message over the years. The book came out of the experience of looking at my goals and going, “I've checked everything off the box.” All the way up to financial freedom, I've checked every single box and I go, “What do I do? Why would I continue to work?” I contemplated it a lot and going, “Maybe I should step away from work. Maybe I should focus more on my family, my spirituality and what we need to do is go back and look at our childhood.” That's how we help a lot of individuals find their purpose in retirement. A lot of it comes out of your childhood, the things that maybe you were passionate about and the lessons that you learned.
When I was a kid, I spent a lot of time with my grandparents. My dad was a hard-driving entrepreneur. He was working all the time. It seemed like he was never home. For me, that's why I got so obsessed over getting to this place of financial independence so I can spend more time with my kids that I felt like he didn't when I was a kid, and mom was a well-known school teacher in the state. I spent a lot of time with my grandparents, Howard Weade and Ralph Bailey. It became the name of our company, Howard Bailey. Howard was this conservative guy. We played this game on Christmas and asked dad, “What was your dad great at? What was his biggest talent?” He said, “Saving.” I was like, “Exactly.” That was what Howard was good at. He was a conservative saver. He was good with his money.
Ralph Bailey, on the other hand, was someone that gave away pretty much every penny he ever made. He was someone that won the biggest award in the state of Indiana for his work in education and giving back to the community of education. He worked in his late 80s and gave me a passion for education. I realized at that point when I looked at my goals list and I had checked off all the boxes. I said, “All these goals I've ever set ever since I was a kid, they only ever had to do with money and things. It was about the collection of money and things.” It didn't have anything to do with family, giving back to others, serving others. It didn't have to do with teaching and education. It was void of a lot of the things that bring a lot of meaning and happiness in my life. At that moment I was like, “How can I start moving those things back on this goal list and creating more purpose in my life out of this?”
Some of us, we get to that place of, “I've got financial independence, I'll retire now.” There's something wrong with our society and thinking that's what God intended. Sorry to get too religious on you here, but we were given certain gifts and talents. We were meant to apply those things. For me, I had this gift for planning, goal achievement, running in business and creating wealth. I was good at that. I found that the financial independence that I had, it was a framework that I hadn't recognized before. I had created this framework around my financial life that gave me this confidence that I had financial independence. I knew that I had all my bases covered.
I never worried about the stock market. I didn't worry what was next in Washington, what's next with tax rates or inflation? I didn't worry about any of those financial things that allowed me to elevate myself, my life, my family's life to the next level. I wanted to share with people my journey. How did I get to that point of financial independence, which led to me having to analyse my purpose and meaning and then spell that out? Because I've read so many books over my career. Over the last few months, I've probably read at least a dozen New York Times bestsellers. I find a lot of them are glorified business cards, especially in the financial industry that doesn't tell you a thing. You might read a whole book and in the end, you find out they were trying to sell you life insurance the whole time. I wanted to put something out there that people could pick up, get true value out of and learn something that's based on academic principles, not some opinion. I had frustration with the books that are out there. I felt like I had a lot of value to add to people's lives. Talking about a topic that they may not get to until it's too late.
Dustin
You talk about science, which I could get like its math, numbers, science. It's black and white. It's the science of retiring confidently. You've got that part in there that I wanted to ask you about. It's the art of retiring with purpose and we talked about it, but talk about that part is not so scientific and artsier.
Casey
We're all unique. We're all different and the things that we enjoy. That's what we've been covering, throughout this discussion. We all have different ways that we find meaning and happiness that comes into our lives. That trickles down to how we manage our assets, how we manage our life savings needs to be reflective of what we truly value in life. We have to sit down and spell out that purpose. What is it that brings me purpose and meaning in my life? Sometimes we can get a little overwhelmed by that. It doesn't have to be all that overwhelming. There can be some pretty basic things. I want to give credit to a friend of mine that runs several different businesses. Ken Wimberly shared this with me. It's been something that I've been thinking about. It’s as simple as his purpose, which is to set a great example for his children, his spouse and all the people he interacts with on a daily basis.
That's a pretty simple purpose. It doesn't have to be overwhelming. For some of the families we work with, it can be, “I want to spend more time with my grandkids or we want to travel, we want to have an RV.” That creates this foundation that we can build this plan off of those impacts all those different areas. That to me is artistic. There is some art in that because I get frustrated by the talking heads. Most financial advisors are saying this is the way to do it. That's not necessarily true. Take Daniel Crosby, who is one of the top behavioural finance experts in the world. He was on a friend of mine's podcast, Brad Johnson. As they're talking through financial planning and the right investment tools and biases that advisors have, advisors will say, “Never use annuities or the stock market is bad. Only use mutual funds, only invest in real estate.”
What Daniel Crosby said, which is a guy who is one of the best-known money managers on Wall Street as well. This guy lives and breathes the stock market. He said that the best strategy is the one that you can live with. It's not the perfect tool or investment that's out there. Dr. Wade found, and I'm a big fan of his, a professor of retirement income at the American college. I love reading his academics, these white papers that he's put out, all the study and research that he's done in retirement income planning. In the end, there isn't one perfect strategy. It's got to be the one that we can live with. There's an art in that and that takes some time. That's where I get frustrated with advisors that say, “Fill out those questionnaires, send it back in and I'll show you exactly how to allocate your investments.” It's more of an art than that.
Dustin
I appreciate that. I find myself encouraging people to get a lot of education as much as is right for them to be the quarterback, to use your word that you mentioned earlier. No one's going to care as much as you do. No one's going to look after it. This idea of hiring somebody and like, “Here, go manage my money.” That's a risky proposition. Maybe I'm saying this to tell myself. It's important to get that education so you could direct people so that you can lead. It's about being a leader in finances, your family and in your business.
Casey
When it comes to the biggest problems people have in their financial lives, most of them are behavioural. Most of it does come down to behavioural issues. If you can control those things as much as possible and the reason the education is so important to your point is that you have to understand what you're invested, why the money is there in order not to panic, not to make mistakes. If you have your entire life savings in an S&P 500 index fund, most research will say you'll be okay for the next 30 years. However, you're not going to be okay if the S&P is down 60%, you decide to sell and wait for a better time to get back in. Two years later, it's rebounded. Instead, if you had funds set aside for emergencies, you had all the funds you needed for income for the rest of your life set aside and you took risks with everything else through the rest of the S&P 500 index fund, at least you'd know, “I'm okay because I've got everything that I need. I can wait ten years for that to come back if I have to.
Dustin
Casey, I could speak more and more with you, but I want to squeak in this one question. Your wife works with you in the firm, is that correct?
Casey
She does.
Dustin
You're running a firm. You're loving it. You are the parents of toddlers. You're thinking about adding more to the family. It's been said you found creative ways to keep those fires burning both at home and at the office. I myself is having a family and knowing that people tuning in have businesses and families, what are those creative ways you've found to light it up both at work and at home?
Casey
For me, your calendar will reflect your biggest priorities in life. If you look at your calendar and it's only business stuff on there, you don't have a single date night scheduled and have time with family. You don't have a financial planning meeting scheduled with your wife quarterly. If you only have business priorities on your calendar, you've got to be honest with yourself. That's your biggest priority in life. Your biggest priority is whatever you've done the best job of scheduling. For me, scheduling is huge. I haven’t always been good at this. If you look back in history, that's all it was on my calendar. It was business things, especially business and self-development.
We spend so much time, as entrepreneurs trying to develop ourselves, and from a professional standpoint or grow our business with a business coach and you have a family coach every single year, I plan time away to spend working on my family and how I can be a better family man. That could be scheduling, which could be my own physical health, my mental health. That could be how my marriages, my relationship with our kids, it could be a lot of different things, but I am scheduling every year. I'm scheduling a couple of days out of the office to focus on family planning time.
I'm also spending some time with my wife at least quarterly sitting down, reviewing our initiatives and maybe this is what's helped us. We run a business together and we have done a pretty good job of prioritizing and managing that business, leading that business. We think of running our family the same way. How can we run our family life like a business? It's got to be scheduled. We've got to have missions. We've got to have a vision. We've got to have values. We've got to be intentional with the time that we spend together. I've bounced around a little bit, but above all else, I think like an entrepreneur and business owner, you've got to think of running your home life like a business life.
Dustin
I want to encourage folks to check out the book, Job Optional. They can do so at Amazon. I know you're going to do something special here. If you liked our conversation, RetireWithPurpose.com and HowardBailey.com. That's where you can check out Casey. Casey, if people want to continue that conversation with you, where else can they do so?
Casey
The main hub is there at RetireWithPurpose.com. What we would like to give up to all of you is we're working on an update for Job Optional. I've got some books here that I need to get off the shelves and I want to get them in the hands of the audience. If you're interested in getting yourself a Wall Street Journal bestselling book, Job Optional, we're going to send it out for free, no cost, no obligation. We have some here in the office. We're going to send them out until they're gone. We've got about 25 of them. What we're going to do is we're going to set up a landing page. Go to RetireWithPurpose.com/WealthFit.
Dustin
If you go to Amazon, you've got to buy it, but this is a way to get it for free. Casey, thank you big time for that amazing offer. Even more so your time, investing your time with us here, paying it forward, sharing that there is an art to this. It's not science and numbers. A lot of people miss that art. I appreciate you bringing that to our awareness so that we can have that purpose in retirement and every day in our living.
Casey
I can't wait until next time. Thank you.

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