And Then Life Pulled Me Back In


On this episode of Building a Better Dave, I open up about a lifelong battle with debt, from childhood lessons learned at the family kitchen table to the hard realities of bankruptcy, divorce, and the ever-looming burden of credit cards. I share how persistent financial setbacks reshaped his perspective on money, hard work, and resilience. Just when he thought he had finally conquered debt, an unexpected basement flood pulled him back in, reminding him that life's challenges are never really finished. Join me as I explore what it means to keep pushing forward when setbacks strike, the value of perseverance, and how sometimes tearing things down is the first step to building something even better.
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Sequence of Topics Covered
1. Introduction & Theme of Debt
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Dave Jackson introduces debt as the main topic and his lifelong struggle with it 00:00.
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Show info and contact details are provided 00:08.
2. Early Lessons in Money and Debt
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Memories of his dad doing taxes and the tension around finances 00:36.
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The influence of the Lannister motto, "A Lannister always pays his debts," on his upbringing 01:22.
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Story of borrowing $300 from his grandfather to buy a car and the process of paying him back 01:28.
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Learning there are no "free lunches" and needing to earn money for things he wanted, such as music albums 01:47.
3. Family Finances & Value of Money
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Family's economic background (not rich, not poor, but frugal) 02:24.
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Use of coupons, hand-me-downs, and lessons in financial responsibility from his mother 02:33.
4. Adult Experiences with Debt
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First marriage: fertility challenges lead to substantial credit card debt for treatments 02:41.
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Living paycheck to paycheck and discussing bankruptcy, which conflicted with his "pay your debts" values 03:30.
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After 9/11, wife's hours were cut, leading them to file for bankruptcy reluctantly 03:40.
5. Struggles with Debt in Later Life
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Marriage to a partner with poor credit and inheriting someone else's credit card debt after divorce 04:17.
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Failed attempts at debt consolidation and the difficulty of accessing better loan rates 05:09.
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Gradual process of securing slightly better loans and working towards being debt-free 05:25.
6. The Turning Point: Selling the School of Podcasting
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Conversation with his boss about potential for the School of Podcasting 05:42.
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Decision to sell the business for enough money to pay off debt, while maintaining a professional relationship 06:23.
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Finishing 2025 debt-free and entering the new year with a clean slate 07:07.
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Enjoying financial freedom and considering future opportunities and contributions to family 07:38.
7. Setbacks: Home Flooding and New Debt
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Feeling of finally catching up to peers in life after years of feeling behind 08:03.
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Discovery of water damage and mold in the basement after heavy rain 09:18.
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Realization of the high cost involved in repairs and choosing to finance the repairs rather than deplete savings 10:30.
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Resuming strategies from earlier years to manage debt and expenses 11:05.
8. Mindset and Coping Strategies
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Acceptance of debt as a temporary setback and readiness to cut corners and reduce expenses (e.g., fewer streaming services, no fast food) 11:48.
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Reflecting on the possibility of being in debt into old age and the impact on personal plans 12:22.
9. Tackling Change and Optimism
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Clearing out the workshop and preparing for basement renovations 12:51.
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Parallel between demolishing basement parts and the demolition of his childhood schools 13:31.
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Considering new configurations for the basement, such as moving down his podcasting studio, and seeking hidden benefits 14:05.
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Drawing inspiration from his grandmother's longevity supported by daily movement 14:18.
10. It is What It is
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Paying for repairs and looking forward with optimism, knowing things will improve 14:46.
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Mention of listener support through "buy me a coffee" on the website to help with expenses 14:58.
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Closing wishes for the audience and a tease for the next episode 15:19.
This show is LISTENER Supported.
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Today I thought I would talk a little bit about
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debt because all my life I've been trying to get out of it.
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And well, live from the basement,
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it's building a better Dave. Check us
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out@betterdave.com email
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us@dave betterdave.com
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or call in your comments
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888-563-3228.
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Now here's your host, Dave Jackson.
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When I was growing up, I remember
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my dad doing his taxes probably on a Saturday
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and probably Sunday, and my mom
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pulling me aside being, you know, the annoying 78 year old
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boy that's just spastic and stupid and just kind of
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saying, please don't poke the bear, just please leave your dad alone. And he'd be,
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he had all these papers all over the kitchen table and shoeboxes
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of receipts and all sorts of stuff. And
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if you've ever watched hbo, there's a
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show called Game of Thrones. And it's all these different families and
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they're all fighting for the kingdom, you know. But one of them is the
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Lannisters. The Lannisters. And one of their sayings is a
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Lannister always pays his debts. And that was kind of
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my dad. He was always, you know, I remember my
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Grandpa lent me $300
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to buy my first car. And I had a paper route at the time
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and we did paperwork and I will do this many payments and
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yada yada yada, and you will pay back your
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debts. There are no free lunches. In fact, even growing up,
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I remember I wanted the song Pinball wizard by
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Elton John. And the only way you could get that,
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this is way before Spotify kids, was to buy the
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double album. No, there was no 45 single or
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cassette. You had to buy the double album of the
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movie soundtrack from the who. And it was a lot of money.
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And so I had to wash a lot of cars and
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sweep a lot of floors. And I did not. It was never.
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Was it like, how much is it? Oh, 18 bucks. Here you go. That
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just didn't happen in the Jackson household. We
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weren't rich. We weren't like, we never went
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without food. But I had a lot of hand me downs
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growing up from my brother. And my mom was the queen
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of coupons. And so I understood the
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value of money, which is why
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when I got married, I knew my wife had
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one ovary. So I knew having a kid was a
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long shot. But we figured, ah, you only need one ovary.
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And who doesn't love trying to have a kid? Well, it turns out that's A
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big pain in the butt after a while, especially if your wife also
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has endometriosis, which is basically speed bumps for kids
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or for sperm. And
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we ended up charging up, I think four, at
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least three credit cards with fertility treatment. And
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I remember her saying, well, because we were
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literally living paycheck to paycheck.
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And I remember saying we should file for
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bankruptcy. And I was kind of like, how dare you?
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Atlantis pays his debts. And the only
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reason I ended up filing for divorce, well, that happened
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later too, but for bankruptcy was 911
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hit and her hours got cut by about 20%.
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And that's all it took when you're living paycheck to paycheck.
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Yeah, I could only juggle so much.
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And so I've always hated debt. I was deeply ashamed
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of that. I had to file for bankruptcy.
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And so if we fast forward, you
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know, I'm out of debt, doing great, always. You know, my,
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my credit is amazing. And then I find
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someone who has horrible credit and I
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marry them. And that was also the case with now ex
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wife number two. And
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we went through many years of marriage counseling.
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Luckily we weren't charging it, but we might as well have, because when we
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finally decided to get divorced, one of the stipulations
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was I had to take her credit card debt,
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even though it wasn't stuff that I bought. It was like, hey, if you
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want out of this, you got to take this.
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And that's how bad I wanted out of that marriage, because I did not want
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to go back in debt. But I took five figures
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of credit card debt, and it took me
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many years because I tried to get a consolidation loan
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to get a better rate. And they're like, no, no, your
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income to debt ratio is too high. We can't give you a loan.
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And I'm like, of course, it makes no sense to give someone a loan
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when they actually need one. But I finally got a,
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an okay loan that was pretty awful. And then I got another one that was
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a little better and a little better. And I finally was about
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three years out from getting
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debt free. And my boss
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and I had a meeting about the school of podcasting.
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And he said, hey, like, why isn't the school of podcasting
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bigger? He's like, everybody loves you. You're a great teacher,
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you're well respected. Why isn't like
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this place the place to learn how to podcast? And I said,
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because it's a part time job and it pays part time
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money. I go, but I'm having a blast. And he was like,
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okay. And the next day he came back and he said, do you think it
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would be bigger if you had more time? And I go, yeah,
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absolutely. And he said, well, what if I bought
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it, meaning the school of podcasting,
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and then you could do that as part of your day job. And I was
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like, that's interesting. How much money are we talking? And he
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offered enough money for me to go, ooh,
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that would get me out of debt. And again,
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that's really, really important to me. And so
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I thought about it. I really like my boss. In fact, we have
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half the conversations were about how do we not mess up
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our relationship? Because he really likes that. I work for
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PodPage. I really like working for PodPage. We
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have a thing in our agreement that after a year, if we want to unravel
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it, we can. But I ended up selling
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the school of podcasting. And I was out of debt
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back in December of 2025.
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So I went into 2026 with no debt. And
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I was loving it because again,
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when I'm in debt, I really don't like it.
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I don't like it at all. And so I was spending
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thousands of dollars to get the debt away.
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And so now that thousands of dollars a month
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was going into my bank account, which was cool.
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I have more money in the bank than I've had ever.
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And I was like, well, great. And I was starting to think about the things
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I could do. I might build a garage on the house. I could.
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I got great nieces and nephews that are eventually going to be
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headed to college. Maybe I could help with that. All the different things
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I could do. And it was, it made me feel
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normal because again,
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I had this weird. I always felt like I
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was four years behind everybody else in life because
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when I graduated from high school, they went to college. I did not.
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I thought I had a great job. It was a union job, working
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in a grocery store. And when you're making almost 10 bucks an hour in
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1984, you know, 83,
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that was not bad money. I was living with my brother, life was
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great. And then the store got sold and
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I lost my job. And that's when I went back to school the
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first time. But everybody else had a four year start. So I've
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always felt like I was behind. And now I
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felt like, all right, I finally caught up to everybody else that was
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my age and I was kind of, oh, I was proud of myself
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just because I dug myself out. And it was great
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until May. What is this? April of this
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year? We got, you know, April Showers bring May flowers
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and we got a lot of April showers. And
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I go down to the basement, which is an absolute just.
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It's just a big giant storage shed with crap everywhere. I grew
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up in the basement, but I only go there now to
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do laundry. And so I go down to do laundry and it's
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raining cats and dogs outside. And all of a sudden I notice that there
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is some invisible person peeing in my basement.
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I can hear it and I'm like, wait, where's that sound coming
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from? And so I kind of walk over and like,
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sounds like it's coming from behind those boxes. So I move all these
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boxes out of the way and a. The first thing I see is mold
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on the wall. Now, I worked for a company that used
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to maintain houses that had been
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foreclosed on. And I know what happens if you get water in the
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house. It's one of the worst things that can happen. And so I see mold,
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and out of the wall is, I don't
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know, a little quarter inch stream of water
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shooting about an inch and a half out of the wall and it's
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hitting the floor, hence making the peeing sound. And I was like,
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well, that looks expensive. And it's one of those things that,
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yeah, I could stick some goo in it and hope that the, the drain just
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mysteriously doesn't show up in another part of the house.
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But like I say, I know what happens when you get water in your
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house. And so I did a bunch
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of quotations from people and had people come in and look
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and it's like, well, I had money in the bank and
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if I wanted to, I could almost pay for it
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in cash. But as much as I hate
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being in debt, I want to have that Dave
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Ramsey nest ready in case things. I'm
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always thinking something's going to go horrible. And
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so I financed, I will be financing and I'll be
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back in debt. And I was like, ugh. But
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some things you got to do even if you don't want to do them. I
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would much rather finance a garage or
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finance rebuilding the basement and making it
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bring back the pool table and the ping pong table and a kick butt stereo.
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Maybe move my podcasting studio down there.
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Everything except, I don't know, have them dig to China
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to fix my draining problems.
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So I spent my whole life crawling my way out
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of debt. It seems like at least in my 20s since then.
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And I got out and life pulled me back in.
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Then I guess the advantage I have
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is I did make it. I. I saw what it's like to live
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debt free. And I know how to cut corners. I'll go back to only
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having one streaming service. I'll go back to no fast
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food. I'll go back to all the things that
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I've done my whole life to save money
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and to get out of debt. I just thought I was done
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exercising that skill. And life has said,
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no, not yet. And then I go, well, wait a minute. If it
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takes me 5, 10 years to pay this
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off, like, I'm going to be pushing 70 at that point.
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It's a little late to put up the ping pong table. Maybe at that point.
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I don't know. We'll see. But I hate being in debt.
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And it is what it is. And you got to do what you got to
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do. The only thing you have control
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over is how you react to it.
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And so I have to go around and
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get everything off the walls. And I'm in
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what we used to just call the workshop. And it has this
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huge all along the wall, this
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super bench that my dad had made. And I see where it's not
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connected to the wall, but it's really heavy.
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And we were talking about we might just cut it up
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because a, I've never used it. It's not like I'm building anything
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and bring it out. And I was like, you know, and then
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there are parts of it. We're just going to have to demolish part of the
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basement to fix it. And I was like,
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well, they demolished my
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elementary school. They demolished my junior
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high school and my high school. Why not?
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You know, I've joked how, you know, all the wooden paneling
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is gone from the room that used to have the pool table because of a
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flood. That was one flood back before I was here.
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And I was like, well, sometimes you got
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to tear things down. And, yep, they're not going to be like they
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were, but they might actually be better.
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And I was thinking of all the different ways I could configure the basement and
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maybe put my podcasting stuff down there. It's cool,
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it's quiet, and
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it'll give me a reason to go up and down the steps. And that worked
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for my grandma. She lived to be well into her 90s, and
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she slept upstairs. So every day, you
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know, she would go up and down the stairs, and I'm like, well,
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that's maybe what I need to do. What are the benefits
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of this particular situation?
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And I guess we're gonna find out, because there's no way around it.
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And I wrote the check to get things started.
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And now it's just a matter of, like, well, as I always say,
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it's gonna get better. There's a link
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in the description of this show.
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If you find it entertaining, if you find it thought
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provoking, if you get some sort of value out of this and you want
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to give some value back, you can go to betterdave.com
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and there's a button there that says, buy me a coffee. And if you buy
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me a couple thousand,
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it'll help me pay off the basement. Yay. There you go. That's all.
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So I hope life on your side of the computer
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glass is amazing, and I'll see you again soon with another
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episode of Building a Better Day.














