Dan The Road Trip Guy

The Unexpected Journey: From Corporate America to Financial Coaching

• Dan • Season 4 • Episode 86

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What happens when life's detours become your destination? Stephen Dawson's journey from the corporate world to purpose-driven entrepreneur reveals how unexpected challenges can shape our greatest callings.

Stephen's path took its first major turn during the 2008 recession when, just eight months into his first job after college, he found himself unemployed,  and questioning his purpose. This crisis moment sparked a passion for personal finance that would simmer quietly during his subsequent fourteen-year corporate career at Macy's and Amazon. Though professionally successful, Stephen gradually recognized the growing disconnect between his daily work and deeper calling.

The transformation came unexpectedly during a quiet moment in church when Stephen received what he describes as a divine message to use his financial knowledge to serve others. This clarity gave him the courage to leave corporate America behind and establish himself as a financial coach for people seeking both financial freedom.

Throughout our conversation, Stephen shares remarkable stories of serendipity and connection—from the college night he discovered his passenger once owned the very car he was driving, to a Pacific Coast Highway adventure featuring natural wonders and disasters that profoundly shifted his perspective on life's fragility and beauty.

For anyone contemplating major life changes, Stephen offers this powerful decision-making framework: "Imagine yourself at 90, looking back. Will you regret doing this, or will you regret not doing it?" This perspective has guided him through career changes, relocations, and challenging goals that fear might otherwise have prevented.

Whether you're questioning your current career path, seeking financial guidance with spiritual alignment, or simply enjoy stories of how life's unexpected turns can lead to our true calling, this episode offers both practical wisdom and inspirational insights about finding purpose beyond the paycheck.

You can reach Stephen at stephen.m.dawson@gmail.com

Speaker 1:

Welcome to Dan the Road Trip Guy. I'm your host, dan, and each week we'll embark on a new adventure, discovering memories and life lessons of our incredible guests, from everyday travelers to thrill seekers and everyone in between. This podcast is your front row seat to inspiring stories of passion, resilience and the pursuit of happiness. So buckle up and enjoy the ride. I am excited to be on a trip today with a gentleman I met back in January of this year. We are in a group that meets every Thursday morning at 6.30 am. We talk about a lot of things, one of those being goals and leadership, and we were brought together by a mutual friend, and I'm just excited to spend a little time with. His name is Stephen Dawson and learn a little bit more about him and what he has been up to over the past years. So welcome to the show, stephen.

Speaker 2:

Thanks, Dan, for having me Glad to be here.

Speaker 1:

Yeah, it's a pleasure to have you. This will give me a little more insight that I haven't found out in the past eight months from you. Take a couple minutes and just tell my listeners who is Stephen Dawson.

Speaker 2:

I was born and raised in Indianapolis, where I grew up. I went to many Indy 500s. While I was there I went to college at Indiana University. After school I just happened to have my first job land in Cincinnati. I didn't know one person here, but that's where my first job took me, so came here not long after. I met my wife, amber, and she's from here, so that really put roots down here for me, tying to her. I've worked in corporate roles, mostly at Macy's and Amazon, for 15 years here in Cincinnati. I did have a two-year stint where I was out in Seattle working with Amazon, but four years ago I left corporate America. Now I'm a solopreneur as a financial coach and really my purpose is to help people gain financial freedom and unlock the life that God designed for them, and I just love my vocation.

Speaker 1:

Yeah, that's great, and until I linked in with you, I had no idea that you worked at Macy's and Amazon, so that was kind of cool. And I also noticed your co-owner of looked like your wife's photography company. Is that right?

Speaker 2:

Yeah, so she has since sunset it. But for several years I was working with her Uh, she has a wedding or had a wedding photography business. I would really, just once I left my corporate job, uh, I was also helping her out with some of the administrative work, the bookkeeping, but also going and being her second photographer, slash assistant on wedding days. So that was a big change, because I'd be I'd be spending my saturdays running around with camera equipment, family photo lists, trying to just keep everything, uh, orderly. Those were, those were, high stress days, but I'm glad that we're done with this.

Speaker 1:

Yeah, yeah, my daughter's a photographer and I don't know if I've ever told you that. And yeah, weddings, they just stress her out. She still does a few, but not as many as she used to.

Speaker 2:

Yeah, it's a big day obviously for couples and you're essentially in the photographer role. You're essentially in most cases like the de facto wedding planner or wedding coordinator that day, really keeping things moving and you never really know what you're going to deal with. Things inevitably happen. Stuff gets off schedule. So yeah, it's kind of you got to be on your game nonstop. Yeah, it's an interesting job but I learned a lot. But that's really ultimately what kind of perked my interest in self-employment and entrepreneurship, because I really really like that aspect of it. So that was kind of a good ground for me to test the waters, if you will, on that.

Speaker 1:

Yeah, that's great. We'll dive into that self-employment here shortly. And then I don't know if in eight months I knew you were an Indy 500 fan, so that might be kind of news to me tonight and maybe you've told me that my family had tickets.

Speaker 2:

We don't anymore, but even before I was born my uncle had a section way high up in turn two of the 500. So we had the same seats every year and once I think my first one I was three or four years old and pretty much once I was in my teen years and into early 20s we were I was going with my dad and family every year. It's been gosh. It's probably been six or seven years since I've been to the 500, but I've seen a lot of good races there and that's a real good section for where it always seems like that's where crashes and accidents and yellow flags happen. So it's exciting. We had exciting seats for sure. Yeah, watching the race every year.

Speaker 1:

Wow, that's fun. I didn't know that. That's great to know, so that'll give us more to talk about on Thursday morning. Well, this is Dan, the Road Trip Guy, and one of my first questions I'd love to ask tell me about your first car or a fun car story that you've had.

Speaker 2:

My first car was a 87 blue Toyota Camry, hand me down from my dad. It was resting out, had all kinds of issues. It got me through high school, but not by much. So once I was getting ready to go to college it's like, okay, I need a real car that's reliable. It's the fall of my freshman year at Indiana University in Bloomington, indiana. The car that I'm driving then it's a 1993 Teal Honda Civic. We had bought it a few months earlier over the summer from a middle-aged guy in a Papa John's pizza parking lot. It just was parked there and had a for sale sign. Then we got to talking and, lo and behold, I bought the car and for me that was an upgrade from what I had before. But it still had its warts. One thing it notoriously did anytime I went over a bump, the windshield wipers would trigger and it would just start. The windshield wipers would go back and forth and I'd have to reset it, just stuff like that.

Speaker 2:

But one of the things when I was a at college I was living in a scholarship house with a bunch of other guys about 40 other guys. As a freshman we had to rotate, taking turns doing sober driving for all the upperclassmen. On the weekends we may be out at the bars. Of course we're not of age. We would be assigned on duty. Okay, we got to pick up John at 2 am from Kilroy's out on Kirkwood Avenue, just to keep everyone safe and it was kind of just a responsibility that we were expected to do.

Speaker 2:

It's one Saturday night, it's two in the morning. I'm almost done, ready for the night to be over, I pick up one of the guys in our house. I pick him up from the bar district in Bloomington and he's got a girl that's with him and I'm taking him back. She's sitting in the front seat, he's in the back seat and we're about half a mile from the house that we're going back to. And near the house there's these railroad tracks. So I drive over them. The windshield wipers start going.

Speaker 2:

Of course they did, yeah, and she says oh my gosh, this is my old car. She takes a close look around inside the interior and she's asking me a couple of questions like when did you buy this? Where did you buy this? And we confirmed that this is her old car that her dad had sold a few months earlier. And then, a minute or two later, I dropped them off and then I parked the car and I'm just sitting there for a minute trying to process what just happened, and that was a moment when I just kind of realized there are these moments of serendipity in life that will let me know that I'm connected as a piece of this larger puzzle that everyone's a part of, and you never know, on any given day, what kind of reconnections or pieces that you didn't even know went together in two people's lives, how they, just in a moment, can come together. That one was kind of a crazy. That was a crazy night and I was like not expecting that when I went out to pick up people from the bars. Yeah, that's.

Speaker 1:

That's pretty funny. I'm an assessment junkie and I took the strength finder and one of my strengths is connectedness and that I believe everything is kind of connected in the universe. I always attribute that to my faith in God, but that's just interesting that this car was connected, that you connected with these people, that's amazing.

Speaker 2:

Yeah, I mean, that's the thing with life is you never know whose paths you'll cross, meeting at the right moment at the right time and the right place? Yeah, it does. I agree with you, dan. I feel like it sort of really gives me more hope and this feeling like we are all part of this bigger. You know existence, we're all social people by nature. You know we're meant for a connection and it's just kind of exciting when those kinds of moments come together.

Speaker 1:

Yeah, absolutely. Wow, thanks for sharing that. That was fun. I don't know if as a kid you took them or as an adult you've taken them, but any epic road trips or just road trips in general that stand out in your mind and you go, wow, that was, that was quite a trip.

Speaker 2:

Yeah, even as a kid, we would go on a lot of road trips. I think probably the most interesting one I had was as an adult, though. So this was back in 2017, and my wife and I this is when we're during that two-year stint in Seattle that I mentioned we're driving down the Oregon coast in a brand new black Dodge Charger that we had rented, so we're a couple of days into this two week road trip from Seattle to San Diego along the Pacific Coast Highway, so this has been kind of one of my bucket list items for a long time, and once we're out there, I'm like we got to go down here. We're in Oregon early in our trip. That morning, we see the big solar eclipse that happened that summer, and we were in the perfect spot, in the perfect band, where you could see this total eclipse, and the birds are going crazy, and that was just a really unique experience, but I didn't plan all of our lodging on like okay, every night on our trip. This is where we're staying. So one of my mistakes, though, was that, okay, that was kind of a prime area geographically for where people would be to see the eclipse.

Speaker 2:

So we keep driving and driving in Oregon, and I mean on that stretch of highway on the coast there's really not a ton of hotels. We ended up finding this dumpy. It was a motel in Brookings, oregon. It looks like the if you've ever seen the movie Psycho, the Bates Motel just like not a place we'd normally stay. But we didn't really have many options at this point. We just it's like hey, let's just stay here for the night, get up early and leave in the morning. So we wake up in the morning there's this distinctive odor that we smell. My wife says someone's got to be smoking here in this next room. Anyway, we open the door and the sky is completely hazy with smoke. It's really hard to breathe. And she something is very wrong here. So she looks at her phone, finds out there's a forest fire three miles from where we're staying and there's a mandatory evacuation order. We hadn't heard anything until she saw that and we realized like we got to get the heck out of here right now.

Speaker 2:

So we start driving south, get into Northern California and then later we see that same morning on our phone that they're down in Big Sur there's been a landslide. I mean we're still like a week away from getting there at this point, but that was a major thing that derailed. We realized like this is going to derail our plans because we're going to have to go all the way around the inland. We won't be able to drive along the coast. At that point I'm just thinking this has been kind of a crazy turn of events.

Speaker 2:

And a couple hours later we get to the Redwood State Park in Northern California and I had never seen anything like this with these massive redwoods, and we're walking around in this park. I just am looking up in amazement and realizing that some of of these trees are over 2000 years old. And how can this happen from just a little seed. Then I just start thinking more about everything that's happened, with the eclipse the day before, the fire from the morning, the landslide, and that's.

Speaker 2:

That's a moment where I'm just like sitting there, I distinctly remember, under this massive tree and just realizing that there's things going on in mother nature that have been developing for millennia. And then there's also these sudden natural disaster events that just can happen in an instant. And that trip really gave me a newfound respect for mother nature and you know, I'm in that moment just realizing that there is something bigger than me that's calling the shots dictates things and that's something that's outside of my control, and it was just a very humbling experience going through all of that, especially from being in the Midwest where there's, other than a occasional tornado, there's not a whole lot of natural disaster stuff like that. That ended up being a great road trip, though I still do need to get back to Big Sur because we never got to see that part. The rest of it was a really cool experience.

Speaker 1:

Yeah, that's fun. Yep, you'll have to make that journey down the continue down the Pacific coast.

Speaker 2:

Have you been on that?

Speaker 1:

stretch, Dan, we have. We went down through Big Sur gosh, it's been years ago, but we've traveled almost the entire way. We did a road trip a few years ago from Petaluma, California, and then we went up the coast to Portland. That was, yeah, beautiful ride. Somebody told me we were out there and somebody saw my map of what we were doing and they're like hey, look, you got to go see crater Lake. And so we got off the beaten path. I don't know if you've ever seen crater Lake, but that was the most amazing view I've ever seen.

Speaker 2:

Yeah, that's on. Yeah, that's one of the items on my bucket list to get over there and we weren't really to Crater Lake when we were in Washington. We really weren't that far. That reminds me we need to get to that one.

Speaker 1:

Yeah, you'll have to go there. Cool trip. Yeah, love it out there. So we'll switch gears. We'll talk a little bit about you mentioned. You worked at Macy's, you worked at Amazon, then you became a business owner, this financial coach, which I'm very interested to learn about. But take me a little bit on that journey of what took you out of the corporate world and and turns you into this financial coach.

Speaker 2:

I had a not or it was more of a less than ideal time timeline when I started entering the real world for work. I graduated in 2007 and then got my first job right before the great financial crisis, with the housing market and the Great Recession in 2008,. I got laid off eight months into my first job, just with downsizing that was going on across the board and that was a really rocky start. Where I was this unemployed single guy living in Cincinnati, still didn't really know anyone very well here and financially it was a hard time because all of a sudden I'm facing, I'm in debt, I don't have any savings, I don't have a job and I really didn't feel like I had a purpose in my life at that time. But I had a really long, difficult and emotional phone call with my dad during that and he kind of helped me see some of the light at the end of the tunnel, to get back focused on, you know, picking myself back up, and I got my next job at Macy's, where I worked for eight years and then Amazon for six years. But during that time I think really that incident that I just mentioned losing my job early on that really motivated me to learn more on the personal finance side, because I'm like I don't want to get in this hole again, I don't want to ever go back there and I want to really put myself. What are the things I can do to really put myself and family in a good position where we have cushion, where we have flexibility, where one of us loses our job, we're going to be okay?

Speaker 2:

I consumed a lot of books, a lot of blogs over the period where I was working in corporate America and I found this really stumbled upon. This thing called the acronym is FIRE, f-i-r-e, which stands for Financial Independence, retire Early, which basically is all about learning how to save and invest as much as you can and eventually get enough where you can quit working and retire early and not work if you don't want to. And once I found out about that along the way, I'm all in, I'm sold on this. I'm still, at that same time, kind of grinding away in corporate America and just over the years I got kind of burned out. I learned a lot from those roles and they were great experiences, but for me, I realized it is not sustainable for me to work 40 years like a whole career in corporate America. Fortunately, we got to a point where we were in a financial spot where I could leave my corporate job and I was helping my wife at the time with her wedding photography business but I still didn't really know what I was going to do with my life. I just knew I needed to get out of that environment.

Speaker 2:

So one day I'm sitting in church and I'm praying silently. There's this moment where God tells me that I was given this gift but I've only been using it for selfish purposes, for this financial skill. In that moment he gives me this calling and purpose to use those gifts that have been given to me. Use those same gifts to serve others through financial coaching, really help people gain financial freedom and unlock the life that God has designed for them.

Speaker 2:

You know, money's a big part of all of our lives, good or bad. It's just the nature of existence that money is a key piece of this, and most of us have challenges in our lives that become barriers to our relationship with God. And I really look at my job as to be a barrier buster. And financially it doesn't matter whether someone you know someone could be a multimillionaire or someone could be completely broke, but in either case, money can be an object that stands in the way of them living in a full relationship with God and my work on this part of my journey currently it's just been so rewarding to not only see the transformation financially in my clients' lives but also really forming deep relationship and community with my clients.

Speaker 2:

And I think that's really something, dan, that was missing in my time in corporate America because I was just this back office kind of necessary role in finance and accounting and audit but I never felt like I was directly actually helping people and now I just love that I'm able to work one-on-one with the families that I do. I get to see firsthand the changes and improvement that are happening in their lives and it's just incredibly rewarding. So I feel very blessed that I finally found my vocation. It was an interesting journey getting here, but I'm just very grateful for what I do have now and just really the opportunity to serve and help others. That's that's kind of what it boils down to for me.

Speaker 1:

That's great and you know.

Speaker 2:

you look back and I don't know if you probably say it's funny but that first job, which happened to be at a time that wasn't great in our country financially, but yet that's when god planted the seed for your future, yeah, and I I didn't see it at the time, but one of the things as I've gotten older is being able to see when there's these really negative incidents in life and, uh, moments of of heavy suffering, there is a lot of good that can come out of that and lessons that you learn, and that's really where a lot of the growth happens. It's not when everything's just great, it's when you face adversity that makes you stronger, but it's not. It's not fun to go through, but it's just a natural part of growing as as humans, and that's, that's just part of the journey that's a great story.

Speaker 1:

And uh, here's a question for you on your, on your business. Is your are your client? You call them clients, I assume, but are they young, old, single families? Is it just a just a mix of all that?

Speaker 2:

Yeah, so I mostly work with couples. Really the age range can vary. I have some clients that they're couples that have young kids and it's growing family and they're in their 30s. And I've got some clients that are empty nesters. They're in their mid to late 50s or early 60s and they're kind of in the five to 10 year window pre-retirement, helping them navigate the journey from working to retirement and how is that going to work out?

Speaker 2:

And anywhere in between, from those folks that I work best with, it's hardworking, friendly, fun Christian couples that are unsure if their money's being managed well, either by themselves and how they've been managing it, or if they've had a money manager but they don't really know. Okay, is this really working out to the way that it should? For us, I'm able to come in and help them really excel at being able to self-manage, where they don't necessarily need to rely on having someone manage their money for them, and that really just instills a lot of confidence in them as they're going through the process and learning more. I just try and simplify things as much as possible. Financial concepts can be super complicated, but they don't have to be, and a lot of that is really just noise. So I kind of try and cut all that out and just say what are the key things we need to focus on and what's important to you, because this is all about just helping my clients use money as a tool to live their best life. Wow.

Speaker 1:

Good for you, thank you. We mentioned bucket list items earlier. What's one big item on your bucket list?

Speaker 2:

Yeah, one I have is going on the Appalachian Trail and doing the full hike. Okay, I know one of your past guests on your podcast. She completed that she did. Yeah, I probably need to talk to her to pick her brain.

Speaker 1:

I would definitely talk to her. That's cool, yeah, and I had another guest who did the Pacific Crest Trail so she did out on the West Coast so that was fun.

Speaker 2:

Yeah, that's another one I don't know as much about, but I probably should look into because I think bottom line is, yeah, I just want to explore more of the country and just the beauty. I know there's a lot of good ways to do that. Yeah, I need to probably dig in more before I put my hiking shoes on.

Speaker 1:

You know, got two good resources I can link you up with. All right, hey, and I would tell you hey, if you want to get in the car, you go to Maryland and you drive US Route 50, which comes right through Cincinnati here on your way to Sacramento, california. That to me is that's the best trail. You can do it in a car.

Speaker 2:

Yeah, I might have to add that one to my list too.

Speaker 1:

All right, that's fun. Imagine today you could take a road trip with anyone, living or deceased. Who would it be? Where would you go? What would you talk about?

Speaker 2:

That's a great question. I would have to say Jesus, I give him the keys, I let him decide where we're going, what we're doing, I just simply follow his lead, and that's essentially what I try and do each day. But to actually go on a real road trip with him would just be amazing.

Speaker 1:

Yeah, yeah, that would be a fun road trip. Here's the thing. I think this is what always resonates with me with Jesus, he never got in a hurry. I'm guessing your road trip might take a while.

Speaker 2:

Yeah, and that's okay. It's so easy for us all to just be in a hurry and and busy and it's like, oh, we got to get to the destination, but you got to take it slow and enjoy the scenery. You know, don't rush through life. Now there's a lot. I think there's a lot of wisdom in that.

Speaker 1:

Yeah, my daughter always tells me dad it's about the journey, not the destination.

Speaker 2:

Yeah, that's good advice.

Speaker 1:

Well, speaking of advice, if you could leave my listeners with a couple pieces of life advice, financial advice, what would it be?

Speaker 2:

Yeah, one thing that I've heard it was about 10 years ago that totally changed the way I think about big decisions are to imagine yourself. For any big decision is imagine yourself as you're 90 years old and you're sitting in a rocking chair on your back porch and ask yourself, as a 90 year old looking back will I regret if I do this or will I regret if I don't do this? This framework has really shaped my thinking, and when I think about things in this way, some things that on the surface might look like a really hard decision actually become easy decisions. Because if there's something that I want to do but I never have the courage to do it, I know that I'm going to regret that and I know if I don't do that, it's going to haunt me. And the longer that goes on, I'm just going to wonder what if? What if?

Speaker 2:

So in those moments I've generally done that thing and it's worked out pretty well. And that's been true for changing careers, relocating, taking on challenging goals that I otherwise would have been too scared to do. And you know, look, we all have regrets. I certainly have some regrets, but when I look back on my life, I really want to minimize the number of regrets that I've had and you know, sometimes you got to realize that the riskiest decision of all is not to take a risk.

Speaker 1:

Yeah, Wow, Great advice. Well, Stephen, this has been fun. We're going to see each other in probably about I don't know nine hours or so, whatever it is. This has been fun on a Wednesday night to take this journey with you. This has been fun on a Wednesday night to take this journey with you, and we've been trying to do this for a little while, and you've been so encouraging in my little project. I've got going here and so I just really appreciate your time. Yeah, thanks for having me. It's been a pleasure. And before we go, leave my listeners you're self-employed if they're listening and how do they connect with you? How do they learn about your business If you got a charity you want to mention? That's cool too. Whatever, you want to leave us with.

Speaker 2:

I'm pretty terrible at marketing and so I've got no website, I've got no social media, so really all of the folks that I work with come from referrals, but the best way to reach out to me is really just through email. It's just Stephen with a P-H, so S-T-E-P-H-E-N dot M is in Michael dot Dawson, d-a-w-s-o-n at gmailcom and you can get in touch with me that way. And, yeah, I'd love to connect.

Speaker 1:

Well, perfect, and I hope people do. And thank you for tuning in to Dan the road trip guy. I hope you enjoyed our journey today and the stories that were shared. If you have any thoughts or questions or stories of your own, I'd love to hear from you. Feel free to reach out to me anytime. Don't forget to share this podcast with your friends and family and help us to spread the joy of road trips and great conversations. Until next time, keep driving, keep exploring and keep having those amazing conversations. Safe travels and remember you can find me on the internet at dantheroadtripguycom.

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