067: How to Use Your “Halftime” to Make a Difference with Dean Niewolny
Everyone wants to live a life of significance – and few people know this better than Dean Niewolny. Dean is the CEO of the Halftime Institute, where he helps people expand their own “first half” success and skills into passion and purpose for meeting human needs and making a difference.
In his book Trade Up, Dean takes readers through your “Halftime”—when you pause to consider how to finish the game—to fuller, richer work and life. He speaks at events around the world, encouraging business leaders to channel their first half achievements into a second half defined by joy, impact, and balance.
Before his own “halftime” experience, Dean spent more than twenty years in executive roles with three of Wall Street’s largest financial firms, finishing his career in the financial sector as market manager for Wells Fargo Advisors in Chicago, where he oversaw a $100 million market.
Many people find themselves searching for purpose and meaning as they approach retirement and try to turn success into significance – and the Halftime Institute’s resources, tools, and strategies are helping people of all ages find it as they walk through the journey of life.
Today, Dean joins the podcast to share the story of why he left his career in finance (and why you don’t have to walk away from your job to serve), how to make the most of the skills and talents hiding within you, and how to leave behind an impactful, powerful legacy.
In this podcast interview, you’ll learn:
- What Dean’s “halftime” looked like, why the concept didn’t immediately resonate with him, and the moment he realized that making money wasn’t the sole purpose of living.
- How so many people find opportunities to serve and live a greater purpose within their existing jobs after their halftime – and how the Halftime Institute’s unique coaching process accelerates this process and empowers you.
- Why simply volunteering at your church or another organization rarely connects you to your calling, how this can lead to new struggles and discontent, and how to use your time, talent, and treasure to the best of your ability.
- What Dean’s mentor did to force him to take action, make a plan, and change his life.
- Why you don’t need to be hugely successful to become significant – and how “low cost probes” help professionals find their passions, put their toes in the water, avoid making major life changes that don’t work.
- The four things that stand out among people who finish well.
- “For we are God’s workmanship, created in Christ Jesus to do good works, that he has prepared beforehand, that we may walk in them.” – Ephesians 2:10
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Casey: Dean, welcome to the podcast.
Dean: Casey, thanks for having me.
Casey: Hey, I’m really excited to have you here with us. I know we’re just going to have a fantastic conversation. I really connected with the Halftime Institute with what Bob Buford’s put out there. Your book, Trade Up, which I just had the opportunity to finish reading here recently and just really enjoy the content there. I think it’s exactly what a lot of the families we’re working with they’re going through and then we’re going to be able to have a conversation regarding purpose and meaning and just the process that the Halftime Institute uses to help walk people through this whole journey of their life in this time of their life that they’re going through. So, I’m really excited to have the opportunity to hear it from your mouth, the CEO of the Halftime Institute and someone that’s lived it themselves, and I guess I want to get started with kind of what your explanation of what the Halftime really is and what your Halftime look like.
Dean: Yeah. Well, Halftime itself is just a season of life that years ago used to be this sweet spot of 55 to 70 years old and what we have found over the years is that it can be as young as someone in their 20s and someone as old as in their 80s. We just had a gentleman go through and he was 83 years old. Instead of calling it halftime, he called it overtime. So, this season of halftime is really, you know, if you read the book, Halftime, the tagline is going from success to significance and what we really do is we help men and women identify those areas of passion where they can go and serve in and volunteer and do things that really have meaning. Most people get to this season of halftime in their life and they’ve been successful. They’ve been successful in business. They’ve made plenty of money. They’ve climbed the corporate ladder, but they get to this place in life and just say, “Hey, this is somewhat empty. There has to be more to life than this.” And, Casey, that was my experience as a young man. My goal was to go out and make as much money as I possibly could, buy all the toys I could because I thought that would bring me all this happiness.
And I was reasonably successful at that. I was in the financial services industry for 23 years, but I read this book, Halftime, in the late 90s and early 2000s and this whole concept of going from success to significance didn’t really resonate with me right away because, again, I thought that happiness would be by making money and accumulating material possessions. And I got to this point my life in 2006 where I looked out my 40th floor office window at the Mercantile Exchange Building in downtown Chicago and I just said, “God, there has to be more to life than this,” and that started me on this halftime journey and that’s where many men and women get to. They get to this point, you know, there is this burning desire in everyone to live a life of significance, to leave a legacy, to leave an impact. And if it’s all about focusing on yourself and making money, ultimately, that will end up being empty. So, to answer your question, folks come to our program and we help them really figure out what are your strengths, what are your gifts, what are you passionate about? And we coach them through that and then ultimately connect them to areas that they’re passionate about.
Casey: Well, Dean, I really connected with the text itself, this halftime, and I think you said it can happen at any time during your lives, and I can’t, I mean, I’ve met with thousands of pre-retirees, retirees. I can’t say that any of these individuals spent the first half any differently than any of the others. There’s very few that are going through that beginning period of their lives. Maybe it’s five years, maybe it’s 30 years, but it’s all about accumulating assets, making as much as we can so that we put it away and that someday we might be able to retire and eventually, we have enough and we say, “Well, now what?” Now, we kind of get to this point of disillusionment and that’s what I felt during that period of time. I just felt, “Well, now what? What do I do with this next stage of my life?” and kind of I think walking through the text was really helpful and you said something earlier. You said that we were reasonably successful, and I want everybody to know Dean’s being pretty modest there.
Dean, I know you had the cars. You had multiple houses. You had your own plane at one point. I don’t know if you still have that, but you are very, very successful, but I think we can and we can go through this at any level of success. It doesn’t have to be tens of millions of dollars. It could be much less now.
Dean: Absolutely. I mean, absolutely and, yes, I did have a plane but it’s a single-engine plane, so I just want to be clear on that. But I think the one thing I should point out here is if someone reads my book, Trade Up, who reads Halftime, they may walk away from that and say, “Well, it’s bad to make money,” and that is absolutely not the case. It’s fantastic to make money. It’s great to make money. It’s really at the end of the day where is your heart when it comes to the money you have? Is it something that you’re doing for just yourself or is there a purpose for your money? So, it’s incredibly important to point out making money is not a bad thing. It’s a great thing and really if you look at the Halftime Institute when folks come through our program, 60% of the men and women that goes to our program actually stay in the industry they’re in. They don’t leave the marketplace and go into the nonprofit or into a ministry. Now some do, but not everyone. Many stay where they’re at and the folks that they serve wherever they’re at, that ends up being their ministry. That’s their area that they can have purpose and have impact.
There’s an interesting story about a guy who came to our program that work for Lowe’s and he was an executive for Lowe’s down in the southeastern part of the United States and this gentleman had a passion for homeless men and women, mainly homeless children, and he came to our program and it became very evident and clear that this was his passion. So, his initial thought was, “I’m going to leave Lowe’s and go and serve with some homeless organization to help those men, women, and children.” He found out that just in his region alone there were 500 employees that were living out of their cars working at Lowe’s and that became his serving opportunity. That became his purpose to help those families. So, my point saying that is the majority continue to make money, which is great, and they stay where they’re at.
Casey: Yeah. You told another story about a gentleman that had come to the Halftime Institute after reading one of the books and I think if I get the story right, he just kind of decided, “Well, I need to set fire to everything,” and just completely decided to sell his cars, sell his house, quit his job, and he was just going to go do something completely different. And the reality was after he went through your process that he was already in a place where he could live his purpose much like the story of this person from Lowe’s. And I don’t know, maybe it’s the same person that had the story but that I think is really, really important because I believe you talk about learning what you were created to do and some of us were created to do the things that we’re already doing, but doing it in a different way that really fulfills our passions and our purpose. We were delivered these gifts by God and we need to embody those and embrace them and figure out how we can use those strengths and talents, those gifts to better the world.
Dean: Yeah, absolutely. It’s an interesting story. I’ll share with you. It’s not the same story so I know you read the book, which I appreciate, Casey, but this particular gentleman worked for a very large financial institution. If you remember when Smith Barney existed, he was one of their top producers and prior to coming to our program, he thought that in order to live a life of significance and really make a difference, he had to become like Mother Teresa and give everything away and sell everything and Danny came to our program. And honestly, he was probably one of the most miserable individuals I’ve ever spent time with initially because he was just so unhappy and when we sat down with him, I asked him, “What’s wrong?” He said, “Well, I thought in order to make a difference that I had to live a life where I couldn’t continue to make money, I couldn’t have nice things, I had to get rid of all that in order to make a difference.”
He actually was clinically diagnosed with depression and ended up in the hospital and when he came to the program, we said to him, “Gods wired you to be a leader, to go and make money, to connect with your clients,” and through a series of events he ended up back in the financial services industry and has 1,500 clients now, and has changed his business a little bit so he can focus on those folks and really serve them well so he’s flourishing at this point.
Casey: Well, you said that he’s really discovered or you helped him discover what he was truly created to do. And how do we learn what we’re actually created to do? Sometimes we think we have it figured out, but we don’t really know, and we read the Bible, we hear one thing, we read this book, we think, “Well, maybe that’s it.” How do we ultimately get to the core of what we are created to do?
Dean: Yeah. It does take time and it does take effort, and both of those require someone to kind of stop and take an assessment of where they are in life and begin to really focus on going on this journey. So, for me personally, and I’ll share some other stories here quickly but for me personally I thought this idea of living this successful life in the financial services world and making a lot of money was the all, end-all, and soon as I mentioned earlier, found out that it wasn’t. But what I really needed to do in 2008 was to take an extended period of time to really focus on what are my gifts, what are my spiritual gifts, what are my strengths. We use StrengthsFinders. Many listeners probably are well aware of StrengthsFinders. What am I really passionate about? You’d be surprised that the majority of men and women that go through our program will say, “Well, I’m not passionate about anything,” and that’s just not true. You do have passions around something.
So, we really help folks figure out who are at the core. How has God wired you? I always love using this verse out of the Bible, Ephesians 2:10 that says, “For we are God’s workmanship, created in Christ Jesus to do good works that he has prepared beforehand that we may walk in them.” So, if you look at that verse in the Bible, what that is telling me is that we have gifts, talents, and abilities, and passions that we’re expected to figure out and use. So, this is a season where you really have to take an inventory of yourself and really understand, “How am I wired? What are my strengths?” So, if I look at my strengths, I’m a relater, I’m an achiever, I’m a developer, and I have other strengths and my spiritual gifts are wisdom, discernment, and encouragement. So, if someone said to me, “Hey, Dean, why don’t you go build a house for Habitat for Humanity?” It doesn’t fit my strengths and it really doesn’t fit my gifts. I’d be awful at that.
So, it’s really critically important that when someone reaches this season of life which everyone will get there at some point where they say, “There has to be more to life than this,” that you really take a timeout and really assess who are you at the core, what are your gifts, what are your strengths, what are you passionate about, and then plug into some of those things as we call low-cost probes and try various things in order to find out what really resonates with you. So, just to wrap that up, when I went through the program, my wife and I had a passion for orphan children and we thought that we would help build orphanages in the Dominican Republic, Haiti in South Africa. That was what I felt was my calling or next step. After going through the program here at Halftime, yes, I’m passionate about orphans and yes, I still am involved in that, but my true Ephesians 2:10 calling if you will, was to help other men and women figure out what God’s plan is for their life. So, Casey, it’s a season that takes time where you really have to take time to take inventory of yourself and ultimately, you will find that right purpose.
Casey: There’s something that you said. I want to get into all those tools here in just a minute because I think those are extremely valuable exercises to go through as you’re trying to find those purpose or what you really created to do, but I think this is a really important topic and it was something I read in the book. You just mentioned that and I quote you said that, “In Christ’s name all ministry is noble and good, but not every good thing has your name on it,” and that I think that’s such an important thing because I can go build a house but I’m horrible at building houses. It falls down. If somebody wants me to help them fix their car that might be something that God would bless but it wouldn’t get fixed the way they wanted to be fixed. I need to use my gifts the way that God intended them to be used. Can you explain or just kind of explain a little deeper that quote?
Dean: Yeah. There’s a difference between volunteering and calling. Volunteering is something that you can do. Calling is what you have to do. So, there’s a big difference between those two. So, if you go in and you volunteer at a church, for instance, I could volunteer and help our cars in the parking lot, but would it be the best use of my gifts and talents and abilities? Most likely not. And what we see day in and day out is that men and women have this incredible burning desire to go and do something and really make a difference, but they don’t know where to go and do it. They don’t know how to do it. So, what typically happens is they will go to their church, for instance, and say, “Hey, I’m here. I like to volunteer,” and the church doesn’t really know where to plug them in. No disrespect to any church, but they don’t really have the programs to facilitate someone who has talent at a fair level of talent and ability and how to plug them in. So, in most cases, they’re plugged into something that doesn’t really fit their calling. So, there’s a difference between volunteering and calling and like I said at the beginning, volunteering is something you could do, you can do, but calling is something that you have to do.
I have a burning passion for special needs children, so I volunteer at the church and help special needs children. But it’s not my Ephesians 2:10 calling. My Ephesians 2:10 calling for this season of life is to be the CEO of the Halftime Institute and help other men and women figure out their Ephesians 2:10 calling. So, what happens is you get into this season that I call smoldering discontents and when you’re in that season of smoldering discontent, you’re really struggling to try to figure out what does God want me to do. What should I do to really make a difference? And if you ultimately go down a path to just volunteer which there’s nothing wrong with that, I want to be crystal clear, it ultimately will lead to you being itching to find something else to do because it’s not truly your calling. So, there is a difference between both of those and sometimes folks will just say, “I’m going to go and volunteer,” and then after a certain period of time to get really frustrated and say, “Well, this isn’t what I thought it was going to be. I just thought it will be more of this.” And that’s because there’s a difference again between volunteering and your true calling.
When you identify your true Ephesians 2:10 calling and you spend time really understanding that, your life will ultimately have joy, impact, and balance and every day you’ll wake up just excited to go and do what that calling is. So, that’s a long explanation, Casey, but there is a difference between those two.
Casey: So, this passion you have for helping orphans, helping special-needs children, do you feel like you’re – are you satisfying that itch? How are you doing that?
Dean: Yeah. I would say right now I’m not satisfying it to the level I would like because my roles and responsibilities in my Ephesians 2:10 calling is the CEO of Halftime. It takes up a majority of my time, but I will say that I always want to do more of that, Am I doing it? The answer is yes. Lisa and I, my wife Lisa and I, we have an orphanage in Durban, South Africa that we help build and so there is a part of us that is serving orphans. There is an organization here locally in Dallas where we live that does horse therapy for special-needs children and I get out there as often as I can. So, I am doing those two things but probably would like to do more.
Casey: And how will you get to the point where you’re more? What’s this next evolution look like for you?
Dean: Well, it’s interesting that you asked that question. If you look at Bob Buford, the gentleman who wrote the book, Halftime, he talks about the sigmoid curve and many of the listeners I’m sure are aware of the sigmoid curve. It’s the lifecycle of a product that typically starts down and then it goes up and pretty soon at some point it turns over on itself. And Bob had 16 of those sigmoid curve lifecycles over the course of his life. So, when we talk here at Halftime about your calling, your calling can be maybe one, two. or three different things and it’s typically for a season. Very rarely does someone come to our program and we identify their calling and that’s the calling they do for the rest of their lives. It’s a version of that most likely but to answer your question, I’m in my sigmoid curve if you will, at the Halftime Institute as the CEO of the Halftime Institute and I’ve been here nine years. I hope I’m here for the next 20 years, but I don’t know if that’ll happen, so we’ll see. I do want to start building margin around my time so I can go and serve in those two other areas a little bit more than I am.
Casey: When you talk about margin of your time, how do you go through that process of building margin? What’s that really mean and how do you walk yourself through this? I mean, it sounds like you’re accepting that you’re living your gifts, you’re fulfilling what you’re created to do. However, you still have these desires and you still want to give more and that’s okay. I think it’s that idea of it’s okay where you’re at be happy with that and be proceeding forward and it will change at some point in the future, and it sounds like you’re making that change by building some margins. So, what’s that process look like?
Dean: Well, we always talk about no margin, no mission. It’s hard to go and serve in your area of purpose or your mission if you don’t have margin in your life. So, here’s a perfect example. When I was in the financial industry, I had this passion way back in the late 90s to help homeless men and women become gainfully employed so I would help them with their resumes but I was working 60-hour weeks at that time. So, there was no way that I can fulfill my mission because I had no margin. So, at that time I needed to take a look at my calendar and try to build margin around my time. We talk about building margin around three things, your time, your talent, and your treasure. So, in order for me to go and help men and women with their resumes, I had to look at my calendar and figure out a way to either remove something from my calendar that wasn’t a priority or as high of a priority or duplicate things where you can do them at the same time.
For instance, when I have my quiet time in the morning, I now will read my Bible as I’m on the treadmill, so I’m able to read the Bible and get my exercise and at the same time because it’ll build margin in my calendar for time to go and do other things that I want to do. So, back in the late 90s in order to serve these men and women, I needed to work longer days, Monday, Tuesday and Wednesday and Friday and I cleared out Thursday afternoons and I went and served at this homeless shelter to help men and women. So, when we talk about building margin around your time, talent, and treasure, you really have to look at from a priority standpoint. What’s on your calendar right now that’s not a priority that you could remove potentially? Okay. Maybe it’s reading Sports Illustrated. I don’t know. I love really reading Sports Illustrated but maybe for some that’s not a priority or maybe there’s other things that you can remove to build margin.
The second thing is how can you take maybe two things that you like to do and do them at the same time? Like I just mentioned, I like to read the Bible every morning for an hour, but I also like to work out and I do those at same time. I’ll be on the treadmill walking or doing the elliptical and reading my Bible at the same time.
Casey: So, this is the time part.
Dean: This is the time part. You can’t serve in your area of passion or purpose if you don’t have margin around your time. It just doesn’t work. So, that’s critically important. Now, even if you’re in the marketplace and you’re still gainfully employed as a C-level executive even, okay, you can build margin in your calendar and go and serve in the areas that you’re passionate about. It just takes time and effort to do that. So, margin around your time, margin around your talent, talent meaning how do we go and identify areas that we can go serve and use our expertise? So, for instance, my expertise at the time I went and serve the men and women at the homeless shelter was around hiring men and women at the organization I was at. So, at that point, I was an expert at reading resumes and understanding resumes. I hire probably 200 people that year. So, I built margin around my talent to go and use that talent elsewhere. Okay.
Then the third thing, around your treasure, your treasure really doesn’t have anything to do with necessarily giving money away. Building margin around your treasure has much more to do with how do you adjust your lifestyle in a way that you can free yourself up in order to go serve in your area of passion. So, Dean and Lisa Niewolny, myself and my wife, we were living this life where we did have the things you mentioned earlier, the four homes and all this other stuff, but in order for us to serve at Halftime and in order for me to become the CEO of Halftime, I can say that nonprofits don’t pay quite as well as for-profit organizations, so we had to build margin in our treasure and we had to right-size ourselves. So, we still drive nice cars, but we drive used cars. We still have a very nice home, but it’s not the home we used to have, and we don’t have the airplane and some of the things that we are able to get rid of. And honestly, it is a freeing experience when you downsize and free yourself up. So, that’s how we build margin around time, talent, and treasure.
Casey: Well, you talked about this transition away from your previous career very successful, making a lot of money, and I have this conversation so many times the families that we’re working with that say, “I’m making more now than I’ve ever made in my entire life. How can I quit now?” But they don’t want to work and the more money they make, they’re really just making it for somebody else. They’re going to give it away or they’re going to leave it to their children someday. They can’t spend it, but they feel, “It’s irresponsible of me to leave this behind. People would give their right arm to be creating the kind of living that I am creating right now. I’m at the peak of my earning years. How can I retire?” So, how did you step away from the money?
Dean: Yeah, that’s a great question. I loved making the money. I love the quarterly bonus checks, but you ultimately will get to a point in your life if it’s in your 20s, 40s, 60s, 80s, where the money just isn’t as important as it used to be. And again, I want to stress that making money is not a bad thing. We have many people go through our program, who they love to do deals. They love to make money. They love negotiating the deal and they continue to do that. They just build margin in their time or go serve in their area of passion. For me, anyway, I got to this point in the early 2000s that I just didn’t like the work I was doing at that point. It wasn’t bringing me fulfillment and satisfaction. To be honest with you, I was quite unhappy going into work. I wasn’t unhappy when I received the quarterly bonus checks. I was quite happy in those days but the other days, it just wasn’t fulfilling to me after 23 years. So, I had a gentleman who was a mentor of mine who said, “Dean, I’m not going to call you anymore until you figure out,” this was 2003, “when your end date is at this particular job,” and he said, “Because I can’t bear to talk to you every month because all you do is gripe and complain.”
So, for me at that point, the money wasn’t the most important thing anymore. I achieved that. I got there and I realized at that point, wow, this isn’t all it’s made out to be. Really what’s important is relationships and making a difference and leaving a legacy for my children and impacting the world in a very positive way. So, when that gentleman called me back, my mentor, and said, “When is it?” I said, “Five years. I’m going to leave in five years, the end of 2008, beginning 2009,” and it completely changed everything for me. I went into work happy every day. I would have a totally different demeanor every day because I knew at some point, I would be leaving to do something different. So, Casey, for me the money piece was so important for me for the first 20 years and then that last three or four years, it’s just like, “Well, there has to be more to life than this.”
What was impactful for me in probably my 22nd year or so in the financial services industries, I went to a funeral for a little old lady and I walked into this church and it was packed with kids and I said to the person next to me I said, “What are all these kids here for?” and she said, “This lady built into all these kids. She was a teacher and she made a difference in every one of their lives.” And it hit me that day sitting in that church and like, “If I died today, first of all, I don’t know who would come to my funeral or if anyone would, but what impact am I leaving if today was my last day? If today was my last day, did I make a difference in anyone’s life or was it all about Dean Niewolny accumulating things for him and his family? So, that was a life-changing situation for me to go to that funeral and see. This lady didn’t have a lot of money, she was 80 years old, but she left such a legacy and an impact on the kids.
So, the money for me was very important. The last thing I’ll just say it was very important until the end of my career when things change, I just have to stress that again, making money is not a bad thing. Many folks come to our program. They want to continue to make money. They love that. Not a bad thing. It’s just really when you get to the end of your life, you’re going to look back and it’s going to be about relationships and it’s going to be about impact and it’s going to be about the difference you made in people’s lives not playing in your casket saying, “Well, I made millions of dollars. Look at me.” It won’t matter at that point.
Casey: Well, I wonder, would Dean do it again? You’ve been through this period of time, made a lot of money. A lot of the finances that the position you’re in today is because of that hard work and sacrifice, maybe not even doing the things that you want to do in order to get there and now that’s enabled you to go follow this passion. It’s enabled you to go partner up, be the CEO of the Halftime Institute. It’s enabled you to spend more time with your family. Still have the nice cars, the nice house, and would you go back and do it differently if you had the ability to do so? In some ways, we’re told you got to make sacrifice and that’s just what it takes in order to ultimately get there. What are your thoughts on this?
Dean: Yeah. Looking back, it’s a great question. The answer is absolutely I would do it differently. I would absolutely do it differently because what I have learned in the last nine years is the joy that I have every day getting up and doing what I do. I love it and what I see and everyone else was going through our program is this incredible joy they have in making a difference in people’s lives and in this world. And so, the answer to your question is I would definitely do it different. What’s interesting at Halftime Institute, Casey, is that we used…
Casey: Dean, I interject, you’re really good at making money. You’re really good at giving financial advice and consulting with people. It would be easy to mistake that as your God-given talent or gift that you’re created for.
Dean: Yeah. Good point. Let me rephrase. I would do it differently. I’m not saying I would change my career path because that is the career path that I should’ve been on and I was I was good at it but I would’ve built into my life much earlier opportunities to go and make a difference and build relationships and build into people’s lives. I spent from age, what, 20 up to age 46, doing everything for Dean Niewolny. I mean, it was all about me. It was all about what cars could I have, how many boats could I have, I want to buy this little airplane, how many houses. It was all about me. So, I regret that to a certain extent because I missed out on those 26 years or so where I could have been building into others. Yes, I was good at helping other people make money and I was good at what I did but I would argue that I didn’t really build into them from the standpoint of life change.
Now, if you’re a financial advisor, you can make surely a very good case that you are building into someone’s life, you are helping them have a financial or a successful financial future if that’s the way you approach the business. I didn’t approach it that way. I honestly being real transparent approached it from the standpoint of how much money can I make for me. So, there are many including my financial advisor that I have right now that he cares a lot about me, and he loves me and his approach to the business is much different than mine. His approach is how can I do the best job possible for the Niewolny family, so they’re set up and financially sound? So, it’s important to point out here that I’m surely not putting down the financial business at all and it’s a phenomenal business. It’s just your heart and how you approach it. And for me, when I say I’ll do it differently, that’s what I mean. I would’ve stayed in the financial services business because I did at the very beginning of it and really love it, but I would’ve carved out more time to make a difference in other people’s lives.
And that’s the interesting thing that’s happening here at Halftime right now. It used to be like I said earlier this 55 to 70-year-old age range was our sweet spot. Now, we have kids. My daughter’s 21 so I call them kids. They’re in their 20s. They were saying, “Hey, I don’t want to have to go and be successful before I’m significant. I want to be significant now. I want to be successful and significant right now.” So, there’s a shift taking place. The other shift is on the older end. It’s men and women who are in their 70s and 80s. We just had a guy 83 go through our program trying to figure out what’s next for him. So, this idea of significance is important.
Casey: Well, I think it’s important as we have this conversation to share with people that Halftime Tarzan rule because it could be really easy just to jump off a cliff and get started and feel like you need to run before you can walk and I really like this rule and I think it’s important to share.
Dean: Yeah. The rule of the jungle, the Tarzan rule. Unfortunately, I didn’t follow it, but it worked out for me personally, but the rule of the jungle is don’t let go of one vine until you have another vine in your hand. And we really stressed to men and women that go through our program that when you go through the Halftime program and it’s like a funnel, Casey, you come in with all these ideas and thoughts and what’s God really wiring me for? And if you look at a funnel, ultimately, at the end of about a year of coaching and some of the other things that we do, you get really crystal-clear on two or three things maybe that God has planned for you to do. So, what we do is and have men and women go and do what we call low-cost probes. So, they’re still gainfully employed or doing whatever they’re doing but we asked them to go and do low-cost probes and we help set them up.
Casey: And what are those low-cost probes? Offer some examples.
Dean: Sure, I mean, they can be a variety of things. For instance, there’s a lady in Houston, Texas after she went to our program. She had this burning passion for infant babies and so her low-cost probe was to go into Bentall Hospital in rock drug-addicted mothers, their babies and she went in and rock those babies every day. Well, that is now become her ministry. She left what she was doing and now does that every day, but as a low-cost probe, we suggested to her to go and try that and then ultimately, it became what she was doing. For me personally, when I was going through the Halftime program, one of the low-cost probes was for me to go to a church and help people become financially independent and help them with their finances because that was my background. So, my coach said, “Dean, it sounds like you still have some passion about helping people figure out their finances.” So, I went to a church up in the Chicago area and volunteered in their Good Sense Ministry to help people with their finances. But I soon found out that wasn’t a fit for me. That just wasn’t a fit.
So, the low-cost probes are an opportunity for you to go and take, identify your area of passion and go put your toe in the water to try it to see if that’s the right choice. High-cost probes are when men and women come to our program they feel after a few months that, “Hey, this is what I’m supposed to do.” They let go of the vine. They don’t have another vine, but they just jump into something that they think they should be doing. That’s a high-cost probe and we really stressed for people not to do that.
Casey: Do you have any examples of anybody that maybe went through some of these low-cost probes or even high-cost probes and found, “Wow. I thought this is my passion. I thought this was what I supposed to be doing but I was wrong.”
Dean: Yeah. There is a gentleman that went through this program and he came to us with this idea already in his mind that this is what I’m going to do, but wanted to kind of check the box and say, “Hey, I went through the Halftime program,” but he was clear in his mind that what he wanted to do was go and start a venture capitalist fund for social enterprise. And at the end of the day, not to bore you with the story, but he left the job he was at, which was a very successful role at a very prominent company and started this venture capitalist fund that after about three or four months didn’t work, and he had to leave that and go back into the marketplace and go back to where he was. So, that I would say is a high-cost probe. The other part of that high-cost probe for him was it did damage to his marriage and to his children because there was so much stress involved. So, that’s, Casey, a high-cost probe. We really try to help the individual figure out what they’re passionate about but it’s really a family adventure even though you’re going about it yourself. You know, how is this impacting the spouse? How is it impacting the children? So, it’s really critically important to before again letting go of one vine and grabbing the other one that you’re sure that low-cost probe is where you should jump in.
Casey: Well, I got some other low-cost probes that you had in the book but along this line of incorporating your family and how important that is to make sure they’re board, you recommend that couples do this planning together, planning their halftime as a couple. What’s that look like and why?
Dean: Yeah. It’s critically important, critically important, and I’ll use myself as an example. I remember when I was going initially through the Halftime program, we did an exercise and it’s called the three disruptive questions and I’ll never forget it. The first question has to do with cost accounting, and they asked me and the others, “What is all your winning costing you?” and I said, “What do you mean what’s all my winning costing me?” “Well, it must be costing you something. It’s either costing you your time, your relationship with your spouse, relationship with your kids, your spiritual life, your health. What’s it costing you?” And after listening to that, I realize that it was costing me my marriage and my relationship with my kids because I wasn’t available and I didn’t take the time to go on dates with my wife and I didn’t go to our kids’ dance recitals and things like that. So, the cost accounting thing hit me like, “Wow. I’m not doing a good job in that area.”
The second question they asked is asset protection and asset protection had to do what’s priceless in your life and what are you doing about it? And it could be the same thing. It could be your spouse. It could be your kids. It could be your health. It could be your faith. One guy that I know I decided that his spouse was obviously priceless in his life and he started something called a Linda Day which is a day every week that he doesn’t work, he only does what his wife wants to do that day. Now, I just got to tell you, I said that to my wife Lisa and she said, “I just want you to know every day is a Lisa day.” So, they knew. But what’s priceless and what are you doing about it? And what I ended up doing on my calendar is making sure that my wife and children’s events were on the calendar first.
Then the last question they asked just to wrap that up was around metrics. If your life turned out perfectly in three years, what would that look like? And it wasn’t what would you be doing. It was what would that look like. And I just said, I would be flourishing in my marriage. We would be strong in our faith. Our kids would have high self-esteem. And so, the family being involved is critically important and that’s what we’ve learned. The successful half timers put their spouse’s interest before theirs. Now, if we have a man or a woman goes to our program, we will ask right upfront what are the dreams of your spouse? What are you doing to help your spouse accomplish those dreams? My wife’s dreams are to help single mothers with children, so she ended up writing a book called Girls of Greatness and she ended up starting up this program called Girls of Greatness. But it was only after I learned through the Halftime program that I need to make her a priority that she started to flourish and I started to flourish.
So, Casey, it’s critical as you’re going on this journey to make sure that your spouse is in all conversations that they’re fully aware of what’s happening because when someone decides or gets to this point in their life and they say, “Boy, God, there has to be more to life than this,” like I did, and you walk into your house like I did, and say, “I think God’s telling me to sell everything and downsize and I think we got to sell our house.” Not a good way to go about it. So, that happened in 2006 and it took us until 2010 before we made the transition. Critical. The other thing regarding the children, it impacts the children. It impacts the children because the children know dad as the managing director of Wells Fargo, that was my last position, well now dad’s no longer there. So, who is my dad? What’s his role? Dad, what’s your title? And even from a spouse standpoint, the identity piece is critically important. You lose your identity if you leave your position. So, family is critical to bring on the journey because they get scared. They’re wondering what are we doing? What are we putting at risk? Is this a midlife crisis? What is it? So, important to have them involved.
Casey: Like you said, you just run and say, “Hey, I’ve got this great idea.” You start just verbally vomiting on your spouse because, I mean, that’s what I do. I get back from self-development events, fatherhood retreats. I get back from and we get out of church on Sunday and all of a sudden, I am really excited and maybe she doesn’t really understand. Where is that coming from and why are you so pumped up and can we just rewind a little bit? How do you think we should handle that interaction? Maybe I’m asking selfishly because I just recently got back from a father’s retreat and I jump back in and I’ve got three pages of notes. I’m ready to dive in and she just spent the last three days taking care of the kids by herself and she wants some her time, but I’m jazzed up. How do you think we should introduce this to our spouses when we come up with these big ideas that we think are going to be life-changing for not just ourselves but our family?
Dean: Yeah. It’s a great question. I don’t know if I’m the right guy to answer because I didn’t do it right. So, I think the thumbtacks and you guys can learn from me, I remember in 2008 going through the program and I walked in and Bob Buford who wrote the book, Halftime, was sitting next to me and his first question was, “Dean, where is Lisa on this journey?” and I said, “Well, I’m not sure. I just know I’m supposed to be on the journey,” and he said, “Stop.” He goes, “Whatever you do, don’t move forward unless you’re equally yoked,” and he said, “If you have a hard time explaining it to her what you’re feeling and you wanting to make this change, write her a letter,” and I’ll never forget that. I wrote her a letter because I was having a hard time explaining what I was feeling but what we have learned here over the last 10 years for sure is that the best way to approach this type of conversation is to ask your spouse first, “Honey, let’s talk about your dreams. What do you see going forward for yourself? What can I do to support you in your dreams, in your area of passion?”
And that usually will open up a dialogue and she’ll start sharing and then you can share, “Here’s where I’m at today. I’m starting a feel, this inkling that I want to do something different.” But if you really make sure that you stress to them that you care about their dreams and aspirations, I think it’s a great way to start that conversation.
Casey: Well, I think it’s important to emphasize not to do that selfishly. You’re not simply asking that question so that you can get where you wanted to get to, but really coming from a place of being genuine and really caring about what those dreams are.
Dean: Yeah. I think that’s absolutely right. I mean, it’s critically important like I said earlier to have a very authentic, real conversation with your spouse to really understand what their dreams are and again be real transparent and authentic about what you’re feeling about yourself. We do have many men and women who go through our program and the second piece to our program is something called the Thriving Family Weekend. So, a man or a woman will come to our program and we call it the Launch Event. They go through that by themselves. The next program is Thriving Family Weekend where the spouse comes. You would be surprised at how many spouses come to that weekend not knowing at all what their husbands or wives are doing. They’re like, “What am I here for?”
Casey: I’m sure that goes well.
Dean: Does not go well at all. But, yeah, so open dialogue is critically important.
Casey: You have this thing, the three questions. Does that fit into this conversation that you might have with your spouse?
Dean: Yeah. I think the three questions are what I shared already, the asset protection, cost accounting, and metrics and those questions do fit into the conversation with your spouse, absolutely, because when you look at what’s all this costing you. If it’s costing you your relationship with your spouse, it’s time to say to your spouse, “I’m sorry. I focused on myself. This is costing me our relationship and I’m hurting you,” or to your kids and I’ve had this conversation. I’ve sat down with my kids, “You know, my job is costing me my relationship with you and going to your baseball games and dance recitals. That won’t happen any longer.” So, yeah, Casey, for sure the three questions are important to have in that conversation to address those.
Casey: Well, you’ve shared with us a lot of different tools but there’s one that we didn’t get to that I think is so easy to do and might offer some tremendous value, and I wouldn’t imagine you recommend all of your Halftimers do this if it wasn’t highly impactful and you have them all read USA Today. Can you tell us a little bit about that?
Dean: Yeah. So, I’m going to share with you a survey but it’s important for me to share this because Harvard came out with this survey and says lack of purpose is an epidemic. 50% of people age 50 to 65 would change careers to have worked with more meaning and purpose. 50% of folks would change and right now they’re saying that only 20%, this is a Gallup poll, only 20% of men and women that go to work every day feel like their job is really making a difference. 80% go to work every day and feel like their job’s not making much of a difference. So, yeah, so we need to ask people around purpose because I said earlier that a lot of people will come to us and say, “Well, I’m not passionate about anything. I’m here because I don’t know what I’m passionate about.” So, what we often do is say, “Well, you’re passionate about something. Everyone’s passionate about something. You just have to take the time to figure out what that is.” So, what we do is we say, “Do a simple exercise. Go and read the USA Today for a week and come back to us and tell us what makes you mad, sad, or glad, what really resonates with you, what really causes your emotions to fester.” And usually, they’ll come back with something.
Now, one gentleman came back and said, “Well, that doesn’t work. That doesn’t work, all I’ve done is read the USA Today for a week and all I’ve been doing is reading the sports section. I just can’t put it down.” We said, “Exactly. That’s exactly what you’re passionate about. You’re passionate about sports,” so he started an inter-city ministry sports ministry in Memphis Tennessee for children and he’s flourishing in that area. So, we have them read the USA Today just to get them thinking about what they’re passionate about. A lot of times men and women get to this point where they turn their dreamers off and there are certain dreams that you have, and I love baseball. I love auto racing. I have a lot of dreams and you do too. And a lot of men and women don’t think creatively around this area of their dreams and their aspirations. We’ve had a gentleman come through who love golf, so he takes disabled children golfing. We had a gentleman who loves go fish and he takes disabled children out fishing. So, turn your dreamer back on in the season and really think about what am I good at and what do I love to do every day that I could get up and say, “Man, I can’t wait to go do that today.”
Casey: I like that that turn your dreamer back on because sometimes we kind of stop dreaming over the years. It just becomes a thing that we slowly get pounded out of us, we’re little kids, and we’ve got these big dreams, we’re going to be the president, and then we say, “Well, maybe the vice president. Well, maybe the governor or maybe the mayor. Ah, I hate politics.” I think there’s a lot to that just getting back to what gave you your passion, purpose, when you’re younger and sometimes it takes something to jumpstart that. You had mentioned how this gentleman is reading the sports section and he’s just thinking he like sports. There’s nothing to do that but it took somebody that interpret that data. It’s like going to a physician getting a blood test and then getting the results and expecting to be able to understand if you have high cholesterol, blood pressure, and what that ultimately means. You needed somebody else there to kind of push you along that had some experience.
Dean: Yeah. Well, what we do here is we have Halftime coaches and I would say coaching is the secret sauce. If you look at any professional athlete even they’re at the top of their game on Michael Jordan and Tiger Woods, Phil Mickelson, they all have swing coaches and coaches even though they’re some of the best in the world. So, at Halftime, we have Halftime certified coaches that help one go on this journey over the course of the year, someone who’s hit the potholes, who’s made the mistakes, who’s been down this journey, and it’s just critically important to have someone guide you. I had a Halftime coach in 2008 when I went through this program and I can’t imagine where I’d be without him. I mean, he was just absolutely fantastic. So, it’s important to have that.
Casey: Well, if somebody’s curious about this process, can you just can walk us through what it looks like to engage with the Halftime Institute, what you walk those individuals through, what that experience looks like?
Dean: Yeah. So, there’s a lot of different experiences here at Halftime. You can go to the HalftimeInstitute.org and there’s a number of different programs and in the programs are anywhere from going through a very robust year-long program all the way to doing a virtual cohort where you never meet your actual coach but you do a Zoom-type meeting so we have a number of different programs. But typically, the program goes like this and that is that you sign up for the program and we have what’s called a Launch Event and that’s typically a two-day event that’s held down here in Dallas. Now prior to that event, you have two coaching sessions with your coach, and they will help you figure out kind of what are the areas that we need to work on. So, we do initially, Casey, a foundation assessment that will ask you a number of questions around your faith and your health and you as a father, financially, and all sorts of different things in order to grade yourself and then your spouse grades you and then one of your best friends grade you.
So, you come in knowing what you need to work on because in order to hear clearly what God’s plan is for you, you need to be free of all these things that are holding you back. Very difficult to go serve in your area of passion and purpose if you’re in massively in debt and you’re worried about that every single day. So, two coaching sessions, foundation assessment, then you come to a two-day program and your coach is here as you go through the two-day program. Day one has everything to do with archaeology. How has God wired you at the core? What are your strengths? What are your gifts? What are your passions? What do you love to do? What would the perfect life look like for you? And we start on day one and it’s exercises all day long that you’ll find to be very, very impactful. We have a dinner that night. The next day is all about construction with your coach. You begin to put together a roadmap on the different things that you need to do over the next two to three years in order to attain and serve in that area of purpose.
And then what happens throughout the year is you have coaching every single month with your coach and then there’s webinars that you can dial into and listen to of other folks who have gone through our program that are out there doing different things. Mike Ullman who was the CEO of JCPenney’s, he’s one of the guys that you’ll listen to. He’s going through our program and he’s out doing various things. So, throughout the year you have coaching and you have a webinar and then the other thing real quickly is in month three you go through something called the Thriving Family Weekend. That’s when you and your spouse will go away for the weekend with your cohort because you come here with eight to ten other folks and you do a thriving family weekend and then you talk about, “What does this mean as far as our marriage is concerned? What does this mean as far as our kids? What’s our family mission statement? What are our family values?” So, we start talking about that.
Then there’s a mid-year reconnect and then at the end of the year there’s a celebration. And so, that’s really the year. Many folks at the end of one year are crystal clear on what they’re going to do next. Many sign up for an additional year of coaching just to help figure it out.
Casey: So, Dean, who’s the right fit for this? Because I can see some listening and thinking, “Well, I’m not a hard-charging entrepreneur or I don’t have enough money yet that I can go through this process.” Is it a good fit for say a stay-at-home mom or somebody that’s already in retirement, that’s in their late 60s? Is it somebody that’s in their 30s that isn’t quite there yet but is on the edge of having a serious crisis and trying to figure out what they’re going to do next and where they’re going to find purpose and significance? Is this for the factory work floor guy that’s working on the factory floor and just kind of doing the daily grind? Who’s this right for?
Dean: Yeah. It’s really right – I don’t want to be salesy but it’s really right to all the folks you just mentioned because there’s different programs here that will fit certain clients. So, we have a program called the 100X program that serves the very, very successful entrepreneur. We have a program called the Fellows Program, which serves basically the C-level executive then we have a program called the Virtual Cohort that serves anyone from the stay-at-home mom to the factory worker to the C-level executive that they’d rather do the virtual cohort. And then for the person who doesn’t want to be in a structured environment like that, we have just one-on-one coaching. So, the lady I mentioned earlier, her name is Sandy Griffith. She’s the one who rocks babies down in Houston. She was a stay-at-home mom, went through our program and just realized, “Man, I love to rock babies and I feel for these babies of drug-addicted mothers,” and that’s what she identified after going through our program. So, Casey, we have a program that fits all the folks that you mentioned.
Casey: That’s awesome.
Dean: Yeah. And what happens is someone would go to HalftimeInstitute.org and they would be connected to Rhonda Kehlbeck, our Director of Admissions, and they would talk with Rhonda and Rhonda would help them figure out where to go.
Casey: It’s so cool that you can do it as a couple. We’ve talked for a long time, my wife and I, how do we go through this process of putting together our family values, our mission statement, how do we set goals, not just individually, but as a team? And we’ve been looking for resources like that and kind of coach you along and it’s nice to have that coach. As you said, it’s so important.
Dean: Yeah. We actually – oh sorry, Casey.
Casey: No, you’re okay. Go ahead.
Dean: We actually started, I should’ve mentioned this actually, that we have a dream together program which is a separate program that husband and wives come to for two days and we just started that about six months to eight months ago and it’s a very popular program.
Casey: That’s neat. Now, I love hearing about all these things that you’re doing. I want to wrap up with one kind of a big question, general question, and that is what are the typical characteristics of those you see finishing well?
Dean: Yeah. So, we have coached thousands and thousands of men and women through Halftime. They’re on this journey. We probably have 40,000 to 50,000 hours of coaching would be my guess over 21 years. And the four or five things that stand out, our number one people who finish well, now we did this as an exercise here at Halftime. We wanted to go back all our coaches and identify what are the four or five things that stand out. So, here’s what they are. Number one, the person who finishes really well is crystal clear on their calling, God’s Ephesians 2:10 calling, whatever that is. They’re not out there floundering trying to figure out they’re crystal clear, “This is my calling. This is the path I need to be on.”
Casey: I want to say those people driving down the road right now, this will be in the show notes RetireWithPurpose.com/Podcast so you don’t need to jot this stuff down, to keep everyone safe.
Dean: Yeah. Don’t write while you’re driving but calling, critically important. That’s an obvious one. The second is the spouse. Folks that we saw that finished really, really well with their spouses, spouses have a priority. What does the spouse want to do? What’s their calling? What’s their passion? What’s their dream? Some of what we talked about earlier. So, calling in spouse. Number three is flexibility. We have found as people get older, they are less flexible when it comes to making changes and making adjustments in their life. The folks that we have seen flourish are those that when opportunities present themselves are flexible to go and do those various opportunities and I’m guilty of that myself. I mean, as I get older, I’m like, “Well, I don’t want to go do that, but it could be the best thing for me.” So, those folks are flexible. The third thing and the fourth thing is encouragement. We found people that really were successful had a circle of friends that encourage them, always were their cheerleaders, always pushing them, always rooting them on to finish and do well.
And what we do at Halftime is we help men and women identify their personal Board of Directors and those personal Board of Directors or folks that will cheer them on that will encourage them and help them if they get off track. One of the sad things just really quick that we see at Halftime is the majority of C-level executives that go through our program come here and they really don’t have any close friends. They have a lot of acquaintances, but they don’t have a lot of close friends, so we help with that. Okay. So, encouragement is critically important. And the fifth is your health. Those that really succeeded and really did well took care of themselves. They were healthy and it was just critically important that they did that. So, calling, spouse, flexibility, encouragement, and health are the five things that people that finish well have done here based on our research.
Casey: That’s awesome, Dean. Well, I hope there’s some out there that will take you up on your offer to do some coaching and you’re doing a wonderful thing out there in the world. You’re helping people fulfill their passion and purpose that leads to a great deal of gratitude that can spread the globe. So, thank you so much for joining us here on Retire With Purpose.
Dean: I loved it, Casey. Thanks for having me.
Casey: Thank you.