Kary Oberbrunner Retire with Purpose Kary Oberbrunner Retire with Purpose
Podcast 1

001: Transitioning from Day Job to Dream Job with Kary Oberbrunner

At the age of 35, Dr. Kary Oberbrunner left his day job at a nonprofit to pursue his dream job: igniting souls. Through writing, speaking, coaching, he helps individuals and organizations clarify who they are, why they are here, and how they should invest their time and energy.

Before this, Kary struggled with stuttering, depression, and had a history of self-injury. Today, as the founder of Redeem the Day and Igniting Souls, and the author of several books, including the new edition of Day Job to Dream Job, he helps individuals in both the business and the nonprofit worlds transition into lives that offer them the 3 Fs – Freedom, Finances, and Fulfillment – while addressing their major fears.

Today, Kary joins the podcast to talk about his own journey of self-recovery, how he helps people who say “I hate my job and I don’t know what to do” find purpose, and what he’s doing to make a difference. In a world where so many people who supposedly “have it all” are so unhappy, it’s a must-listen – and could very well help you change your life for the better.

In this Podcast Interview, You’ll Learn:

  • How The Shawshank Redemption inspired Kary’s book – and how it serves as a central metaphor for much of his work.
  • What it really means to be “trapped” – and why it is no way to live.
  • The single thing that is most damaging for children as they grow up – and what you can do about it.
  • Why the side hustle is becoming increasingly common in our society – and how to find and embrace yours.
  • The day Kary “woke up” – and how he became laser-focused as he transformed his life.
  • How to make a value proposition statement, attract buyers to you, and cut through confusion and ambiguity.
  • Why people aren’t toxic and trying to hold you down – but may tear you down because of their own fears, lack of action, or apathy.
  • What we can do to reclaim the clarity we had in youth that we often lose sight of in middle age.
  • When you should NOT run from your day job – and why the most unhappy retirees feel that way.

Inspiring Quote

When at least three people have asked you for advice in a certain area, you are a perceived expert in their mind.” – Kary Oberbrunner

“It’s often less about dream discovery and it’s more about dream recovery.” – Kary Oberbrunner

Interview Resources


Day Job to Dream Job: Practical Steps for Turning Your Passion into a Full-Time Gig

Dream Job Bootcamp

The Shawshank Redemption (Movie)



Man’s Search for Meaning The Classic Tribute to Hope from the Holocaust

Happiness Is a Choice You Make: Lessons from a Year Among the Oldest Old

Listen to the Kary Oberbrunner Interview

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Read Full Transcript


Casey: Today, we’re here with Kary Oberbrunner on the Retire With Purpose Podcast and typically I would kind of give my little overview of who Kary is. However, I just got done reading here a few weeks ago, Day Job to Dream Job, and Kary does such a great job of writing the book itself. I actually put a great bio of himself in the back of this and I wouldn’t normally just read something whether it’s on TV or we’re doing a podcast or whatever it might be. But you know what, Kary, I’ve got to read your bio. I’m going to read this passage from the book.

Kary Oberbrunner left his day job to pursue his dream job, igniting souls. Through his writing, speaking, and coaching, he has helped individuals and organizations clarify who they are, why they are here, and where they should invest their time and energy. Kary struggled to find his own distinct voice and passion. As a young man, he suffered from severe stuttering, depression, and self-injury. Today, a transformed man, Kary invests his time helping others achieve their true potential. He is the founder of Redeem The Day, which serves the business community, and Igniting Souls, which serves the nonprofit community. The author of several books, he has earned his doctorate. Actually, already a doctorate here. We’re speaking with Dr. Oberbrunner. He earned his doctorate and transformational leadership. Kary also serves as a founding partner on the John Maxwell team, a huge fan, and also, he says he and his wife, Kelly, are blessed with three amazing children.


Casey: So, Kary, with that, I welcome you to the show.

Kary: Hey, listen. I’m excited to be here. Love this concept of what we’re talking about today and I dressed up just for the interview today.

Casey: Well, I appreciate that. Yeah. If you’re not on our YouTube channel on watching the video interview here with Kary, you might just be in your car listening to the podcast, you wouldn’t realize that he’s sitting here and true to the dream jobber fashion in a gray t-shirt and drinking those kombuchas and that was how we tuned in together. We just kicked off just a few minutes ago and Kary pops on the t-shirt. I said, "Wow. You really live it, don’t you?”

Kary: That’s right. Well, listen, this topic is so important because 86% of the population right now are not happy with where they’re at. In fact, they’re saying to themselves, “I really wish I was in a different context. I wish I was in a different venue. I wish I had a different job. I wish I could retire but I feel trapped and therefore I can’t.” And listen, Casey, as we talk about the feeling of trapped, what that really means is those are prison-like conditions and you know as a reader of the book that I actually use the metaphor of Shawshank Redemption to talk about this 86% of the population of whom I used to be where I felt imprisoned in my day job. And let me tell you that that is no way to live your life.

Casey: Well, and when we first started talking right before we got started with our recording here, Kary, I could kind of see it and I felt this with a couple of different people I’ve interviewed over time where they go, “What am I going to talk? Retirement? I hate retirement.” I interviewed a business owner and he said, “I hate retirement. What am I doing here?” And you’re talking about, well, how do I quit my day job and start my dream job. And I had to start, you know, most of the people we’re working with are in that demographic of 60 to 65 and most of our listeners are 45 to 75. They’re in retirement, they’re starting to think about retirement, and more and more of the people we’re working with are transitioning from a day job into their dream job.

And for people like you and I, that just love what we do, we’re not too concerned with retirement. We’re not thinking, "Well, yeah, I can’t wait to get to 65 so I can get on Medicare and I got social security then I can then live the dream.” It’s, "Well, why don’t we start living the dream today?” And I’m finding more and more people I’m working with that are transitioning into a dream job and we’re helping them establish their finances in such a way that allow them to truly live their dream and do it risk-free. You’re helping a lot of people do this that are maybe in their 30s or 40s transitioning into a dream job kind of what I might call a purpose-based retirement. They’re stepping into something they absolutely love and that is real scary.

Kary: Absolutely. Look, at the age of 35 just so people know a little bit of my quick story, at the age of 35 serving in a nonprofit organization I was tapped by the senior leadership and told, "Look, we see you as the future leader of this organization," and there are no secrets here. I mean, it was a nonprofit organization with over 1,000 members and it's a great honor to be tapped but in that organization, here’s the crazy thing. It’s, "Hey, we pick you as the successor but you’re not going to assume the role for ten years because the founder needs to use his transition plan to transition out.” So, think about that, Casey. Here I am, dad of three, young ones under six, three under six. Did my doctorate. Studied for this. This was like the dream and I feel like it’s totally wrong like I’m not supposed to spend the next 10 years of my life sitting on the bench which let’s face it, some of your listeners right now maybe they’re sitting on the bench because they know if they retire today they would lose a whole pile of money that would come to them in three or four years. And so, they feel like they’re clinging on just to essentially go to jail every day so that they can collect more money.

But here’s the interesting thing, just two days ago a gentleman named Doug who’s 63 suddenly says to me, “Kary, today I’ve decided to retire,” and I’m like, “Why, Doug?” He said, "Because I just got a prostate cancer diagnosis.” So, see, is that interesting, Casey, how it sometimes takes life to wake us up? And we get a diagnosis and then suddenly it’s like, "No, I’m retiring yesterday,” and then we feel like we got to live our lives when in reality we need to get kicked out of the nest. Have you seen this to be true as you talked to people as well?

Casey: Well, I think one of the things you said that really struck me, I had to highlight it and circle it, you said professional prostitution.

Kary: Oh. That was strong. I got a little bit of heat when I said that.

Casey: Yeah. But that was so good because as you said, I’ve got one of my best friends that his dad was getting ready to step into retirement. He turned 65 and he’s going to retire when he’s 65 and then they give him, the CEO loses his job, and now they’re, “Wait. We want you to be a CEO. We’re going to double your compensation and not only we’re going to give you this great compensation package but you’re going to be running the organization. You got this great title,” and so many times we’re doing that for the title or for the compensation and they didn’t need the money. They didn’t need the money and they wanted to retire but now they couldn’t. They felt trapped. They’re in jail. And I think that was why you talked so much about the movie, Shawshank Redemption, and the book. I mean that was a constant theme throughout the book. You actually wrote Day Job to Dream Job while you sat in Shawshank prison. Is that right?

Kary: Right. Well, I actually sat in Andy Dufresne, played by Tim Robbins, his cell that he went into solitary confinement after playing the music on the loudspeakers, the opera music, so that the prisoners can feel freedom and then he got put in the solitary confinement. That’s actually where I wrote the book and I’ll tell you why I wrote it because I was…

Casey: You say you wrote the book there. How much time did you actually spend in that cell?

Kary: I made a few trips.

Casey: This isn’t a small book.

Kary: I made a few trips there and little did I know that the Ohio State Reformatory because I didn’t grow up in Ohio, it’s 90 minutes from my house so I didn’t know that but here I am watching this movie and all of a sudden, I google it. And I thought it was in Massachusetts or something like why is that awesome place in Ohio?

Casey: This awesome place.

Kary: Yeah. But anyway, I look it up. Sure enough, it’s there and I literally explained to the staff there the vision of the book and the vision of the book is that you go from prison to plan to pay off. Okay. So, you go from prison, Shawshank, to plan which is the book, Day Job to Dream Job, to your payoff. So, it’s like Zihuatanejo if you know the movie, at the end of the movie Morgan Freeman and Tim Robbins had this reuniting in Zihuatanejo after they get out.

Casey: Mexico, right?

Kary: Right. Because Tim Robbins wanted to be a charter fisherman and here’s what I tell, Casey, I tell people that dream jobbers have three things in their life. They have freedom, finances, and fulfillment. Freedom to go as they please, finances to earn as they wish, and fulfillment to live as they like. And so, you can have the two out of three and you’re still in jail but really a dream jobber they have all three and that cannot be replaced by any salary.

Casey: Well, I think it’s hard for people to make that transition because of this fear they have and I think you’ve actually helped people make this transition. They were in that later stage of lives where they were at retirement age, where they said, “I’ve really got this dream job that I want to follow,” and that’s one of the things that if you didn’t know about Kary that he does. He helps consult with individuals that are going through this transition out of a day job into a dream job and it’s kind of weird. I feel like I do the same thing every day. However, I’m kind of working on a different side of the equation because I’m working on the financial side but there’s so much more that goes into that. And just the other day I had, well, I’ve got a client that I’ve worked with now for about three-and-a-half years, a doctor, single, no children, multimillionaire, lives off $50,000 a year, and continues to work in earnest. He says, “Well, I’m making seven figures. How can I possibly quit?” So, with the only reason that you continue to work is for somebody else. You’re not working for yourself anymore. Now, you’re working for charity or you’re working for some airs that you don’t have. And so, you’re having these conversations every single day.

Kary: I am.

Casey: And so, share with us somebody that you’ve helped kind of overcome that fear.

Kary: Yeah. Listen, I’m going to show you the exact person. His name is Steve and let me just take - for those of you who are watching on iTunes, you can’t see this but…

Casey: Head on over to our YouTube channel.

Kary: There you go. So, in 2015 of August, no joke, see, right there, August 14, 2015, so three years ago this gentleman named Steve sends me an email, “We’ve never met but I feel like I know you. I’ve got your book from blank and I finished it this week. I’m sitting on the shores of Lake Huron while on family vacation.” You see it, Casey? He can’t even disconnect from work. I mean, this is how bad it was. He took his work with him wherever he went even on family vacation but he says, “I must disconnect from my day job. My wife agrees. Can you help me? How do I start this process?” So, what I did is I basically said, "Look, man, you got to go through a Dream Job Boot Camp. And this guy I’ve never seen anyone take it as serious as him but I don’t think you can see this picture but he basically printed out every single thing. I mean he started taking notes. He started tracking everything and I could tell this guy was serious and basically, we talked and I shared with him this Shawshank metaphor illustration and he kept saying, "Yeah. You know, I feel like I’m Andy,” and I said, “Hold on, Steve. You’re not Andy in the movie. Do you know who you are?” He’s like, "No.” I said, “You’re Tommy.”

Now, if people don’t know about Tommy in the movie, Tommy’s the guy that gets let out in the courtyard and shot by the warden and murdered. And Steve’s like, "What are you talking about I’m Tommy?” And I replayed back to him his own advice that he was saying and how as he was aging he was getting more and more ostracized from the company, put in situations where he wasn’t agreeing with what he was even saying anymore, and this set up was beginning to take place. And he knew what I was telling him that the writing was on the wall and if he didn’t get out, he was going to be taken out. And sure enough, man, look at this, on January 14, 2016 so we’re just talking about five months later he crawled out of the sewer pipe in his own words and I got him on video here where he actually shows it and check out his statement here in January and then I’ll let you push him to ask questions but he says, "Please forgive my lateness in getting this note to you. I really needed sometime this week to disconnect from my day job and reconnect with my family. I did not realize the toll the past year has had on me.” Casey, do you see that too where people don’t even realize the toll of everything?

Casey: Oh, yeah. And I think there are some things, some statistics you shared in your book about that that you said you need - if you want to live longer, get into your dream job. You shared with us five different reasons that you should start your dream job and one of them is living longer and you shared with us some statistics. And I thought they were pretty interesting and ones that would be pretty darn motivating if I was in Steve’s situation and you said that the L.A. Times reports there’s a 33% increase in heart attacks on Monday mornings. The NCDC says, "More people will die at 9 AM on Monday morning than any other day of the week.” Entrepreneur magazine says, "Twenty-five percent increase in work-related injuries on Monday morning and male suicides are the highest on Sunday nights while we start to think about Monday in our current financial situation.”

Kary: You talk about jail. I mean, there’s a term in Japanese called karoshi which literally means death by working and if you googled that term you will see images of people in Japan that are literally dying like a dude in a suit dying, laying there because they don’t have boundaries. They’re just taught like honor super big in that country and, yeah, I mean we talk about all the cancers and all of this stuff and the alcohols that take people's life. What about stress-related heart attacks? What about this suicide that we've seen kind of rise now that Hollywood is finally talking about it because there have been multiple people that have killed themselves who had it all. They've had all the money, all the fame, all the connections, and they still feel like a life without purpose is killing them.

And, yeah, that’s why I’m passionate about this cause. It’s not, "Oh, I hope people buy my book or I hope people join my boot camp.” It’s like you know what, Carl Jung, a Swiss psychologist or “Yung” as some people say, in all of his research he said, “What’s the most damaging thing in the life of a child?” And when I was asked that question I was like, “I have no clue. Is it abuse? Is it abandonment? Is it alcoholism?” The thing that he said was, Casey, the unlived life of the parent was the most damaging thing for the life of a child because for 18 years they saw their mom or dad or guardian live a life that they literally hated and then they looked at their own schooling and said, "Why am I doing school when mom and dad come home to say, ‘Don’t talk to me. Give me the remote. Give me a 12-pack. Let me sit on the couch so I can veg out?’” Veg is short for vegetable and we all know vegetable have zero brain waves, dead brain waves. And that's how most people, unfortunately, are coping with a job that they hate.

Casey: Well, I think you talk about the rest. I mean, there’s so much there that we need to unpack but I want to kind of go back to this whole the – what did you call it, the Japanese word for it?

Kary: Karoshi, I believe.

Casey: Karoshi, right? So, we’re experiencing that when we are working whether we’re 20 years old or 60 years old but aren't those risks greater and greater as we get down the line? We get to be 40, 50, 60. I mean, the risk of heart attack is going up, and so the damaging effects of working in a job are much worse during the end of our career than the beginning but it's much more difficult to step away at that point because you go, “Well, I’ve only got three years left or I only got five years left,” but then what are you going to do after that three to five period? What's next? And I wouldn't say it's not just the health risks that get bigger once you get to the tail end of your working career, but it's a financial risk too. If you’ve got five years left and you're in a job you really don't like, well, the risk of you may be losing your job is probably a little bit higher and be very highly dependent on that last few years of income in order to make the transition successfully in the retirement. So, starting that process, I mean, this was just one of the things that went off in my head, starting in that process sooner rather than later is not just helpful for your physical health and your longevity, but also your finances.

Kary: Exactly. I mean just to do the full loop on Steve because people might want to say like, “Great. He graduated from your program. Then what?” Look at his page. You can google him.

Casey: Sure Foundation Strategies.

Kary: Yeah. Sure Foundation Strategies. Today, he’s a consultant. So, so many people that are in their 50s, 60s, 70s they have so much knowledge and so much expertise that you know what, it's a crime not to share that content and wisdom and I get it. Listen, some people today might be like, “Well, gee, I don't know anything about social media. How can I get clients? Blah, blah, blah.” Listen, you could always find an excuse. I have an 83-year-old author who just published her first book six months ago.

Casey: It’s never too late.

Kary: Yeah. Her name is Pat Gano and she crushed it and I have other people who are in their 70s who are writing books. So, the point is this like if you think you’re old, you’re old. Okay. I know people that are dead at 20 or 30. They just haven't made it official yet and they're just walking around as dead people who feel trapped. Age is irrelevant. You talk about Diana Nyad. Remember her? She swam 110 miles at the age of 64. She had this dream of crossing this channel and she failed five other times in her 20s, 30s, and so forth, and at 64 she crushed it. So, I don’t believe for a second that age is anything to worry about. It really isn’t. You have some of your best years now and let's face it, my buddy, Doug, that I just mentioned he retired overnight because he said, "This prostate cancer. No way, man. I’m going to enjoy travel.” Well, now it might be a little bit too late and that's the fear that some people have.

Casey: Let’s talk about Steve a little bit. What did Steve do specifically? What was his living before he became a consultant?

Kary: That's a great question. He was basically in this organization for a lot of years just like most people. You get in there, you rise up through the ranks, you become part of that corporate, you know, and he literally showed me his watch, the gold watch I mean. It sounds…

Casey: He got the gold watch before he retired?

Kary: No. I mean, afterwards, he did, but it sounds cliché, but I mean that's what most people want to do is they just they fall into a job. They keep getting promoted. They keep finding their identity. They keep finding their significance and there's like you said, there are trials, and then they come in and save the company and then suddenly they look back and say, "Wow. There went my whole life.” I retired at 35, Casey, not because I was a multi-multimillionaire. In fact, I was a nonprofit leader with three kids and a wife but look at it this, man. I said, “You know what, I’m going to go create my dream job,” and after I did, people said, "What was your process?” In the in the book, I actually give the nine steps that you can take for any profession, any industry, but I tell people this all the time: clarity attracts, confusion repels.

So, I don't think it's wise to just go in and say, “Hey, I’m quitting tomorrow.” “What are you going to do?” “I don’t know. I’m going to figure it out.” I'm all into the side hustle. The side hustle is so key and there are so many people today that are doing the side hustle. In fact, the number increased I believe by, I’ll google this later, but I believe it went from 13 million to 44 million Americans within a five-year period, who said, “I'm actually gaining income other than my main job.” So, it increased like three times in five years because the Internet and side hustles are becoming so much more common which I think is very wise.

Casey: I want to touch on that transition thing in the freelancing and part-time gig but I think there are some people that are listening, they’re saying, “Well, Steve, he sounds kind of like a big shot. He has a corporate job.” He was a professional, had all kinds of insight in the ways that he could transition into a consulting position. I see most people that are transitioning into their dream job in retirement, they’re doing consulting. I mean, there are other things you can do in retirement whether it's opening a boutique or writing a book, doing things online. There's a lot of opportunities but I think that the average blue-collar worker goes, "Well, how am I going to - I don't have anything to offer. How am I going to find my dream job? What am I going to possibly consult on? I've been working at in the line at GM for the last 30 years or the gas company.”

Kary: Yeah. I got a great example. I’m going to go straight personal here. I’ll do two family members. So, the first family member is more in your demographic. This guy, my father-in-law. His name is Mike. Mike got a buyout at the age of 52, 53, from Verizon where, sure enough, it's like, "Hey, you're being expensed. You’re expensive to keep on.” He started in the company and sure enough, some of these blue-collar workers that worked out on the field they’re in the lines so he got a buyout. Anyways, the guy is a genius with his hands. I mean he can just do things that I'm like, "Okay. I got to call him an expert,” and he's just amazing at it. So, no joke with what he does. This is crazy. He literally and this is going to be disrespectful for some people. Some people are like, “Oh, okay,” but he goes around on junk day, okay, where people are literally in richer neighborhoods throwing out the best stuff like this beautiful chair that has one leg that’s cracked or something like that. He literally goes around, loads it up, brings it back to his workshop, and puts like minutes or sprays it down or something, puts it on eBay. The guy’s making a crazy amount of money and he's working with his hands. And now he's in his 60s, but it's a beautiful…

Casey: He’s dumpster diving and making dough.

Kary: Yeah. I mean, yeah, exactly.

Casey: What a great example of you can literally find something that you can do, right?

Kary: It’s unbelievable. He'll call us up and we’ll be like, "Oh my gosh, you know, I found this thing that was being put out on the curb and I just made $160 and I spent 10 minutes fixing the wheel,” and I’m like, “How did you even fix the wheel? I don’t even know how you did that.” But in telling you, like you can do this and so, yeah, there are things that my sister who is a different demographic. She worked at Victoria's Secret as a manager for like 17 years. No college education and felt like she was trapped in retail. Well, guess what, you google Sarah Oberbrunner. She's in the top 2% of all real estate in Wisconsin because she's crushing it and she's great with people. Retail taught her that, and she's single, and she's making a ton of money offering a ton of help but there’s another example we’re trapped in retail. Every Christmas, every Thanksgiving, every working, working, working, working and now she can set her own hours and she's got a team around her now.


Casey: If you're ready to take the next step towards securing the confident retirement you've always wanted, then stop by RetireWithPurpose.com. You have three options to get started. If you want to stay on top of current retirement trends, you can sign up for my weekend reading for retirees where I offer up four trending articles on retirement from experts in the field with my own personal insights directly to your inbox every single Friday or maybe you're ready to see what a purpose-based retirement strategy would look like for you. Then apply to receive a free copy of one of my latest retirement planning books. And if you have specific questions you'd like to get professional guidance on, you can sign up for a complimentary consultation. It's up to you. Again, that's RetireWithPurpose.com. Now, back to the podcast.


Casey: You brought up somebody, you brought up the whole transition, the partial transition, the freelancing hour-time thing and I think something that a lot of folks struggle with is how can I have that conversation with my employer at this point in my career when I'm…? I’ve been here for 25 years. How could I possibly leave? And there is somebody, Mark Henson, you brought up…

Kary: Sparkspace.

Casey: Yeah. Great story about Mark. Actually, I thought it was you as I was reading the book, “Oh wait, no, no, no. Okay. This is Mark.” Yeah. It was a great story about how he was somebody that actually I wrote down what he had said, but he went to his employer and the employer actually helped him make this transition, right? They gave him the time and the opportunity to spend on something he really loved doing and I think most people, “Whoa, how am I possibly going to approach my employer and have this conversation?” Because, I mean, you talked to almost any entrepreneur that's been highly successful. I think it's highly false that they went all in and took massive risk in order to have massive reward. They always had some kind of fallback position so that they knew they couldn’t end up in the gutter someday and that's what you - you're not telling people, "Just go quit your job and start something to make a transition.” How do you have that kind of conversation with an employer?

Kary: So, listen, there’s a Wisconsin research study that was done at the University of Wisconsin that says that you will be more successful if you have a side hustle. I’m trying to google it right now to get the study but you are actually more successful. I got it right here, okay. So, it basically, okay, by the way, 44 million Americans, that was the stat, are doing a side hustle right now. But basically, the point is that the study Wisconsin says that the people that we often glorify that the greatest people had a side hustle and here's why I think this is so important. You develop in you discipline and skills that if you just said, “I'm cutting cold turkey,” the pressure would be too great financially. So, let me say that again. This is what I did. Here I was a nonprofit leader in an organization. I started writing books on the side. There's no reason my employer can say, “Well, you can’t write a book especially on the topic of what you're passionate about.”

Where you get nailed, Casey, is if you're a bad employee. If you're a bad employee and you’re disengaged which the Gallup poll actually says that only 29% of employees are engaged in their job. The other 71% are disengaged or actively disengaged. But if you're a good employee like Mark Henson was, Mark was the one who organized the company softball game. He was the one who showed up, filled up with energy and excitement. So, I mean, this guy was a valuable employee and then he went to his employer and said, "You know what, there's this space that opened up in downtown Columbus and I think it would be great for the company to have a meeting space.” They’re like, “Oh, no, no. We don't have time for that, but you can do it. If you want to do this on the side, you can have this room.” And you're right. You read in the book. Mark would go there in the morning. Set up the space. Rent it. Go to his day job. Take lunch off. Run back. Set it up for another meeting. Run back. Finishes day job. And then clean it up at night. And, yes, you cannot maintain that pace forever. There is this launching process that happens but it needs to start with the getting your feet wet and that's what happened. Mark did this and sure enough, then what his employer said is, "You know what, it seems like you're really passionate about this. Can we still keep you, but only at 30 hours?”

Casey: That’s exactly what he wanted.

Kary: Yeah. And that's exactly what he wanted and eventually, it came to the point where they said, "You know what, we need you for this new project that came in. You either need to step up your hours or you need to break free,” and by that point. I mean, he had everything mapped out. He loved it. That's the other thing, Casey, a side hustle confirms your passion because it's dumb to just say, "Hey, I’m done with you,” and go out and experiment. But when you can do a side hustle and then see, “Oh my gosh, I feel so much more alive,” and you know it's funny. You might say, "Well, my family wouldn’t be okay with me doing a side hustle.” Your family actually might thank you because you come home more alive, more excited, you're more engaged. You finally have some pep in your step instead of, “I got to go to work again,” and all this stuff.

Casey: Then tell us, we heard about Mark's transition, but you did a similar transition, right? You did directly into this dream job you live today. What did that transition look like for you?

Kary: So, for me, believe it or not, it was a couple things that bridged the financial gap. Because again, I have a wife who’s a truth teller. She's not one of these wives who are like, "Oh, honey, you do whatever you want you. I trust your dream.” She's like you know, "We got three kids. They’re under six. How are we going to do this?” which is great because…

Casey: You had to turn your sales language in there.

Kary: But that’s the truth. I had to tell her first but here's what happened. Remember, I was writing Book 1, Book 2, Book 3, Book 4 all during my margins of being a dad. I mean, literally, I woke up probably about two hours earlier and wrote in that space. So, that’s what’s crazy. I mean, you can do a lot an hour a day. Turn off the stupid Netflix. Shut down the media and the surfing which you’re surfing because you're in pain and you just try to cope with your pain, start avoiding the chronic pain, and I tell people often I get this from my coach, Chet Scott, "But pain is inevitable. Misery is a choice.” So, like you can either have the acute pain of starting your side hustle, which is short-term focused and intentional or you can live your life in chronic pain. Most people choose chronic pain.

Instead, what I did, Casey, is I said, “I’m going to set the alarm 90 minutes before anybody gets up. Work on that book.” Well, sure enough, a wealthy individual came to me and said, "Oh my gosh, you're writing these books. I want a book. Have you ever thought about being a ghostwriter?” And I’ll tell you what, Casey, I said, "Absolutely.” And then I went home and I googled how do you become a ghostwriter? I’m serious. I just said yes to this gentleman named Scott and he’s like, "Well, what do you charge?” and I called one of my friends who was a ghostwriter and, you know, at that point that first gig I gave a crazy big price and I said, “You know, this is what it would be,” and he’s like, “Well, do you have a contract?” I literally made all this stuff up because I tell people, “Look, all you need is to take imperfect action.”

Everyone is such a perfectionist, they say, "Unless I know that 27th step, I’m not going to take the first step.” Clarity comes with action. You take the first step and the second step appears. So, literally, ghostwriting and then becoming a coach on my books. I started to basically get hired to coach on my books. That was kind of the income and once I started doing it, I loved it. I hate an office. Today, I’m in my wife's office. I don't have an office and people might be like, “Well, gee, you must not be making money.” Dan Sullivan says that an office is where an entrepreneur goes to hide from opportunity.

Casey: Yeah. I love Dan. Such a great inspiration there. So, I think there are two things there that you said that really allowed to make that transition. One, you just said yes. You said yes to the opportunity when it presented itself. But you set yourself up to be introduced to the opportunity in the first place. Some might say, "Well, you're lucky.” Well, you put yourself in the position to be lucky so when luck came along, you are able take advantage of it and that was largely by doing things that other people in your position weren’t willing to do, putting in the hours that other people aren't willing to put in and those hours can be very painful, painful time. They can take with your margins, right? They can take away from the time you want to spend with your family, but maybe that only last five or ten years and you have 60 years of bliss, 60 years of doing what you want to do. We’ve got to make those sacrifices.

Kary: A couple things you said, I have a quote that I say often, "When you prepare for the moment, the moment is prepared for you.” So, I literally began preparing for the moment because prior to getting that side hustle, there came a point I didn't even share this part in the story, oh my gosh, remember when they came to me and offered the job at that nonprofit and they said, “Will you be the successor?”

Casey: Yeah.

Kary: I thought about it. I prayed about it and I just knew the answer is no so here I am stuck. Do I tell them yes and then quickly come up with this side plan for three years from now or do I tell them no and then maybe suffer the wrath? Like, "No, I don't want to be the successor.” “Well, then why are you here? You know you're out.” So, no joke. This isn’t my proudest moment, but I basically said no. Then as an emotional dad of three under six, I basically cried to my director, not by choice. I mean, it just emotionally came out and I said, "Please, don't fire me because I don't have another option.” And I’ll tell you what, that’s the day I woke up and I said what am I doing? And I woke up and I said, "You know what,” first of all, they’re a great organization. They didn’t fire me. They let me stay on another two years, but I knew the writing was on the wall and those next two years, Casey, I became laser focused. I didn’t go out hunting with the guys. I didn’t go out cycling with the guys. I mean, I literally said, "Work, life, faith,” and then I said, "Side hustle,” and I got so serious like Andy with Shawshank. When he knew the writing was on the wall and he just dug on the side of that cell with the little rock hammer at night when everyone is sleeping and sure enough, he came up with his escape plan.

Casey: And I'm curious, I mean, you went to this very intense transition period. How do you spend your time now? What does a typical day look like for Kary?

Kary: Yeah. So, listen, now that the kids are back in school, the days are what I want them to be. And I know that sounds like, “Oh, wow. That's pretty cool.” But today, I mean, this morning I went up, got up before the kids get up and I went cycling with my buddies because health is very important to me. Then I went home, took the kids to school. The hallway on the school, conversing with the kids, helping them prep for their tests.

Casey: Not just running in and dropping the kids and getting out as quickly as you can.

Kary: No. I mean being really engaged and I went to Hilton Polaris. It's a hotel near our house. Why? Because I met with our videographer for a conference that’s happening in October and we mapped out the whole shoot of the conference and then I grabbed my kombucha and now I'm doing an interview with you and then what happens after this I’m meeting with finalists in the Author Academy Awards contest that I created from all over the world. Like, it literally is a dream come true. And like you said, there is pain to do a side hustle and its short-term pain but it's worth it because you create the life that you want. And I’m also the CEO of a publishing house now called Author Academy Elite, Igniting Souls, Redeem The Day. I mean, I have this whole thing now, which is a tribe of souls on fire. I speak, I coach, I write, but it's amazing and what happened, Casey, is I went from a few years ago thinking it was all about me since where we all start to now I tell people selling is serving and marketing is storytelling.

So, anybody who’s listening right now who says, “You know what, I don't have a lot of skills,” can you serve and can you tell stories? And maybe you feel like I'm oversimplifying it but if you can serve people, you can sell people and if you can tell stories, you’re an awesome marketer or what have we been doing in the last 15 minutes? Telling stories, marketing. So, look, there are so many opportunities today. You don't need to be a Walmart greeter. I’m not against Walmart greeters. They’re nice people.

Casey: It might be a unique ability, right?

Kary: Yeah. It might be. It might be. There you go, strategic coach, but I believe that, well, here's a quick formula. It's called a VPS so let’s get practical. Value proposition statement. This is borrowed from somebody else but, literally, your listeners can do this. It's a formula. I am ____ who helps ____ do or understand ____ so that ____. So, when I meet with people right away I talk with them. I say, “I am ____.” What are you? “I am a consultant. I'm a coach. I’m a financial planner, so I am ____ who helps ____,” that’s your target audience, “do or understand ____,” that’s the impartation of skills or knowledge, “so that _____.” Now, when you can do that, that’s called your value proposition statement, that my friend will attract buyers to you. Prior to that, if it takes you 29 minutes to explain to somebody what you do, I tell people it’s called the drive-through drill. Nobody wants to drive through a fast food restaurant and say, “Hey, what do you guys serve here?” and the guy says, “I don’t know. What do we serve here, Bill?” Everyone's going to drive away and you are a brand. You're a CEO of a cool little company called YOU and if you don't know your value proposition statement, by certain your clients and your future clients won’t know it either. You need that statement that that tells people what you do.

Casey: Well, I hope if you’re driving down the road right now, don't try to write everything down that Kary is saying. It’s all extremely valuable stuff and I know you want to absorb it. Just go to RetireWithPurpose.com and we’ve got everything in the show notes. You can highlight it, you can print it, and enjoy it. Kary, something that I wanted to touch on that is something that I see with a lot of families that I work with, yes, I’m working with couples, I'd say probably 80%, 90% of the families we work with are families or couples making their transition into retirement or they're saying, "You know what, I want to do consulting or I want to start a new business. I want to do something I really love every day,” and they’re being held back by their spouse, by the significant other quite often. It sounds like you had a very supportive spouse, but it takes a little selling, but ultimately you had a very supportive spouse that helped you make this transition. And one of the things you wrote in your book, as you said, when you don't seem fearful, loved ones often take it upon themselves to make sure you feel the fear. How should someone receive and interpret these comments that they’re receiving from someone that might be the closest person to them?

Kary: Yeah. Well, I’m going to give them the benefit of the doubt. I don't believe that your loved ones, your family, your close friends. I don't believe that they are toxic and they want to keep you down. Here’s what I believe one of two things. They’re either scared for you because they don't want to see you get hurt and they think wisdom, conventional wisdom especially, is going to somehow talk some sense into you, but let me just challenge that for a moment, Casey. Is conventional wisdom to put all your chips on one employer where they can walk in one day and say, "You're done,” and then you lose everything or is it more wise to be an entrepreneur perhaps where you have multiple clients and if one client comes in and says, “I'm done with you,” you got 29 other clients? So, I challenge conventional wisdom a lot.

The other reason why family and friends often shoot us down is because you are saying yes to your dream and I'm not about unicorns and rainbows and just, hey, believe you got a dream and go for it. You'll notice Andy Dufresne had a dream and for 19 years, he dug against the side of his cell and came out with a plan. In other words, I’m a truth teller. It does take work. It does take hustle. But what you do when you say yes to your dream is you force your family and friends to look in the mirror and many of them look in the mirror and say, "You know what, what Casey’s doing, what Kary’s doing, what Steve’s doing, what Mark's doing, you know what, I have a dream too but I'm not willing to look in the mirror. And a result, them rising to the top in their dream is forcing me to look inside and I'm not happy with what I see so I’m going to tear them down so I can feel better about my lack of action and my apathy.”

Casey: That’s so true. You know, most of these people when they’re in that transitional period and they’re trying to figure out can I make this? It comes out of fear. That's what I see from spouses, it’s this fear of the unknown and ultimately, it's that the plan hasn’t been formulated well before it was delivered. I've got a couple that I worked with and when I originally met with him, she didn't come. She didn’t even know he was meeting, right, and he wanted to figure out how he could transition into retirement and he said, “I haven't told her yet.” He didn’t bring her in until the third session and we had everything laid out in detail, exactly how this is going to go and, yeah, she was concerned, but imagine how much more fearful she would've been if he would approach that conversation not having any of the answers.

Kary: But you know what’s interesting, because I totally get what you’re talking about, look at the guy who tried to talk Andy out of his dream. It was Morgan Freeman. Morgan Freeman pulled him out in the courtyard and said, "Look, man, you're crazy. This is a pipe dream. You’re nuts. What are you thinking?” And you know what, Tim Robbins just walked away and basically said, “You know what, I'm doing it anyway,” and notice who followed him. See, that's the crazy thing. Morgan Freeman follows Tim Robbins because he has to look inside and say, "Oh my gosh, Andy Dufresne’s living a free life and I'm not,” and he eventually followed him to Zihuatanejo. So, I get it, man. Listen, there was a time where my wife probably thought I was crazy, probably thought I was nuts but I'll never forget the day where she came to me and said, “You know what, Kary...” She didn’t say, "You're right,” but she said because normally she is right, but she said, “I'm proud of you and we weren’t in the right spot prior to this, and I believe in you.”

And sometimes you need to not – she used to be the enemy in my head like she doesn’t believe me, she doesn’t believe me, and you know what, that was actually me saying, “I don’t believe in me either.” I had become convinced in my own mind, not reckless, but I had become convinced in my own mind first and then she could borrow my belief. I think that that's very important. I highly doubt I would've done it without her support because she did support me. But there comes this time where Jeff Bezos, I mean, look at Amazon today. People try to talk sense into him and say, "Come on, man. What do you mean you're to start this bookstore online? Just play it safe.” I mean, everybody who’s ever done anything was tried to talk off the ledge and yet they had this burning desire. The word entrepreneur, I know we’re talking a lot about that today, but the word entrepreneur means bearer of risk, bearer of risk, and you know, Casey, that with your financial planning, you mitigate, you eliminate the risk.

Casey: Put a backup plan together.

Kary: Yeah. So, that's the secret strategy of my book: prison, plan, payoff. And if people go from prison to pay off, they’re crazy. That's where Howard Bailey and, Casey, they help you put a plan together and that's what's needed and that's what Dream Job Boot Camp does as well.

Casey: Well, what you said about, these are borrowing, right? Where we’re borrowing that ability and then it kind of becomes the spouses and I can’t tell you how many times, I actually cannot think of a situation where I’ve sat down with a couple where, I mean, just a couple I was talking about a moment ago, we just had their review the other day and she's – I said, “How’s work?” She said, “I'm quitting.” Every single time where a spouse is against retirement of the one spouse because they’re afraid of it then they see him or her do it then they go, “Oh, that looks nice. I think I can do that too,” and then we find a way that they do it. That happens without fail.

Kary: That is so funny. Listen, I got to just share this here. See this business card, Clearwater Counseling?

Casey: Yeah.

Kary: My wife when I left my day job, she was at a counseling firm. Guess who's the entrepreneur now? My wife. So, same thing exactly what you're saying. She had to see it in me first and now she loves it because now she can not take clients on certain days. See our son’s games. Before that, she couldn’t. She was like in a prison where you had to work certain hours, certain times, rent out your office certain hours. Now she's freedom, finances, and fulfillment.

Casey: So cool. Now you also said in the book that there are some reasons that you should not leave your day job and I thought this was really neat because not only do they apply to people that are working, that are in their day job, trying to find their dream job that can really take them all way to retirement, but people that are also thinking about retiring, have some bad type of restlessness as you said in your book. And you named reasons that people should not leave their day job, boredom, running from improvement, escaping an assignment, haven't paid the price when you think you're better than people around you. And that's a big view. People that retire because of those reasons are the most unhappy retirees I run into.

Kary: Yeah. Listen, if you're leaving because you’re bored, you're not going to something. You're running from something. I believe that when you retire that you should go to something. And as a result, retirement now has a purpose. I mean, we all know about Viktor Frankl, Man's Search For Meaning, the guy who was in a concentration camp. He saw prisoners dying all around them and it wasn't that they were in pain and suffering. The people who died in the concentration camps were the ones who didn't have a purpose beyond their suffering. If you are just suffering in your day job but you don't have a purpose, you’re going to be purposeless on the other side and you’re not going to have that fulfillment. In fact, you might be more in pain because now you don’t have a title, you don’t have income. I encourage people, yes, you absolutely need purpose beyond your job and then move toward that and that's the most fulfilling life there is.

Casey: As we wrap up here, how do you find, how do you help people find that purpose? How do you help? If you're sitting there going, “I don't know. I just hate my job. I don't really know what I want to do in retirement and I don't really know what I want to do if I want to start a new career,” how do you help people identify that purpose in themselves and really dig deep to find it?

Kary: We have a process in all of our programs, we call them soul on fire questions, and it's a list of 81 questions where it forces you to put down the remote control, the iPhone, anything else that's a distraction, and it forces you to get clarity on what you really want because reality is most people are surviving. They’re in boredom. They’re coping with their pain. They really haven't done the deep work to say, "You know what, what do I want to have achieved prior to my death? What places do I want to have visited?” Here’s another thing, Casey, as well. Oftentimes, when I work with people they are known as the answer person in a certain subject. I tell people often, “When at least three people have asked you for advice in a certain area, you are a perceived expert in their mind.”

So, no joke. We have one client who is amazing at decorating and it comes easy to her. So, for a year she thought, "Oh please, these people are just patronizing me. They're coming into my house saying, ‘You’re a great decorator. How you do that?’” Well, I told her, “Have three people asked you how to do this?” and she's like way more than three. I said, "Look, there is a need. You have an ability and now you need a framework to charge them. You need to process.” And suddenly she got a framework and it's, you know, hey, come in for a consultation and, hey, here's option A, B, or C and now she has a business, but again, most people they are too good that they think everyone else can do it. As a result, they don't see that there's a business inside them because they have a need. The public does and they have an ability to meet that need.

Casey: In one of our past episodes we interviewed John Leland of the New York Times. He wrote Happiness Is A Choice You Make.

Kary: Wow.

Casey: And it was a great book that really just profiled several people that were near the end of their lives, 85 to 105 years old, and one of the things that he said in the book, life is kind of like chess. There are so many moves on that board that you can't just start making a move. You have to play the end of the game and work your way back to the initial move you make. I mean what you're helping people do is say, "When you're 85, what’s going to be important you? When you’re 90, what's important to you? When you’re 80? When you're at the end of your life, what's important to you? And now what does it take for you to start living like you are 85 every single day of your life, and following that passion? Because that passion when you're 85 is probably the same passion you have now and you can somehow monetize it.

Kary: Yeah. I tell people often that you know back to your point a second ago, it's often less about dream discovery and it's more about dream recovery. So, when we’re born in this world, believe it or not, many times we have more clarity than we do when we’re middle-aged and toward the end. Because as a kid you come out and you say, “I want to be this. I want to be that. I want to be this,” and you have crystal clear clarity and so many times it’s not about, “Hey, I got to go discover now what I want to do.” It’s like, “I got to recover and almost like take myself out of the matrix of everything that I've been taught is good and acceptable, and I need to unplug the matrix.” And I think that something powerful happens when people can do that when they start listening to their own heart and their own voice, rather than what everybody else is saying, and then pair up with you and your team because there's this truth-teller component that we all need, a guide. We need a guide to help us make that transition.

Casey: Well, yeah, Kary, it's been great and I've got one question I like to ask every single guest that comes on the show and really every person I ever sit down with on a consulting basis or even large groups. I want to at least get the engine started and some that haven’t even thought about this yet. You’ve been thinking about this for years. This is probably too easy. This is like cheating. What does retirement mean to you?

Kary: What is retirement to me? One word. Freedom. Freedom because for so many years I used the word “have to”. I have to go here today. I have to go to this meeting. I have to go to this appointment. And one day I woke up and said, "Look, have-to are each prison bars and have-to creates a cell and that means that I’m no longer free and literally, today and every day I wake up and say, “I get to,” and it’s not just semantics like I literally get to do what I love. So, to me, I retired at 35. Even though I’m working hard today and every day, L. P. Jacks talks about the master in the art of living draws no sharp distinction between work and play, labor and leisure, mind and body, education and recreation. They simply pursue their vision of excellence and leave others to determine whether they're working or playing because to themselves, they always appear to be doing both. That's a master in the art of living. There is no work. There is no play. It’s integrated.

Casey: Gosh, you know, we could continue to have this conversation for another hour but there is one thing that I have to - that really hit me hard. You said it earlier in the show. You talked about how you just talked about – you kind of talked about have-to, get-to thing and so I've got a three-and-half-year-old that last night he said, "Dad, do I have to go to school tomorrow?” I said, "No, you get to go to school tomorrow.”

Kary: Awesome.

Casey: And so, that got me thinking it's all about, you said a lot of this comes out of what you experienced as a child, what you saw your parents do. That’s one of the most damaging things you can do to a child, live in your own little prison your entire life. They get to see that and just think that that's the way life is. What about grandparents, right? I mean, grandparents are like for me, my grandparents were some of the biggest influence in my life. I named our company, Howard Bailey, after my two grandfathers.

Kary: Wow.

Casey: And I wonder what kind of advice could you give to grandparents who want to show their grandchildren how they can live their purpose in life and how they don't have to live in a jail cell every day? Without at the same time, I think some grandparents some have this fear, this generation that they go, “Well, they just don't like hard work. The millennials, boy, and generation Z, they just want to go to work at 9 and come home at 4.” So, it's like this delicate balance that they say, “I really want to empower them to do what they love doing and get out of jail, but I don't want them to think they don't have to work hard.”

Kary: Right. I think the best thing a grandparent can do is have the video match the audio and what I mean by that is that let them see in you this harmony. We've all seen movies. I don’t want to make a racial slur by calling them a certain movie but we've all seen movies where the audio doesn’t match the video and they're talking and the mouth’s opening and we say, "That's a fake movie. What’s going on?” The old movies back in the 70s.

Casey: Right. All the old kung fu movies.

Kary: Exactly, exactly. But today when a young person sees that, "Hey, you should follow your dreams.” “Well, why don’t you do it?” You know, that's an immediate disbelief and the audio doesn't match the video. So, Steve's exact words to me, I referenced Steve a while ago, his point was, “I want to be believable because right now my kids are not seeing and my grandkids they're not seeing a guy who's living what he's telling them,” and he knew there was this disconnect and so I do believe millennials and X and Z and you name it and Y and all the generational labels, they work hard about what they’re passionate about. So, right now, there's a ton of young people who are passionate about Fortnite. They're working so hard.

Casey: The video game, right?

Kary: They’re working so hard to become an expert in that. What you need to do is you need to tap into what they're passionate about and they will still work hard. A lot of people at sports, acting, music, they will work hard on what they're passionate about. That's the key is matching that passion and then the hustle will come.

Casey: Share your passion with your children. No matter what your stage in life, right?

Kary: Love it. Yeah. And expose them to different things, different experiences.

Casey: Well, Kary, is there anything that you would like to share with our audience before we close up here?

Kary: You can find all about me if you just google Kary Oberbrunner. I tell people I’m a bald guy with a girl’s name so google will correct you when you butcher my name, so no worries about that, but I have a daily show. I have books. I have programs, live events. All of it is just built around helping people become souls on fire and I'll close with a quote by Ferdinand Foch, a French general who said, "That the most powerful weapon on earth is the human soul on fire,” and I truly believe that when we are souls on fire we’re living out our God-given purpose. And so that's my deep passion is to help people become souls on fire.

Casey: Well, Kary, there's another thing that you have I believe coming up here. We’re recording a little bit before the second release of Day Job to Dream Job.

Kary: Yes.

Casey: And I'm telling you it was a great book. I mean, whether you're stepping into - I mean, it really doesn’t matter where you’re at. There were things in this book, I would say I'm living my dream job and I’ve got notes on almost every page. I mean, I really thought there was a lot of valuable information that I could actually input in my business and it was helpful even from a marketing perspective. And so, I think anybody could benefit from that book. I think sometimes you read a book titled like that and you go, “Eh, I'm happy already.” But, hey, whether you're happy or not, pick it up. I mean, it was a great book. You're rewriting it right now, adding a lot of good information and releasing that October 27.

Kary: October 27. Yeah. It’s mainly updated information because you can imagine four years ago even just some of the stuff that existed technologically has changed and so the people are going to get the same message but they’re going to get some updated statistical research and stuff like that.

Casey: Tools.

Kary: Tools, exactly.


Casey: Great. Kary, wow, thank you for this opportunity. Honestly, I had no idea this was going to be as great of a conversation as we had and I know you've helped people with the hour you spent with me and that's our mission here on Retire With Purpose. So, thank you so much.

Kary: Well, listen, a big shout out to you because I think very few people in your industry are having these conversations and thank you for being an industry disruptor, an industry leader in this area.

Casey: I understand you're not too far away from us so maybe we’ll be able to get a cup of coffee someday.

Kary: Awesome. Thank you so much.