Guest Post: How to Live Like You’re Rich for Pennies on the Dollar

Today I bring you a story from Clay. He doesn’t have a website or anything, he just wants to share his story about how he found his own freedom. It is quite a powerful read and more people should hear it.  

A little over three years ago, I was just like many of you.

I had two car payments, a mortgage payment that I could barely afford, a semi-secure job…etc. I had no savings, felt unfulfilled with my lot in life, wished I could move but was chained to my house because it was worth much less than I owed on it, and I pretty much just went through every day thinking, “This is as good as it’s going to get…. and I don’t like it!”.

My wife and I lived that way for several years and then our lives changed dramatically. You’re probably expecting me to tell you about some get rich quick scheme I discovered and how you should jump on board too. But, that’s not what this story is about.

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In Feb. of 2013, I was fishing with my son and his friends in our neighborhood when my wife called me on the phone. I couldn’t make out what she was saying at first because she was crying uncontrollably. She had taken my 8 week old daughter to her 8 week wellness checkup and the doctor didn’t like the fact that my daughter was still jaundiced. So, he drew some blood and told my wife he’d call her if anything was wrong. Well, a couple of hour later, the doctor called and asked my wife to come back to the doctor’s office. He needed to discuss something with her. My wife asked to be told over the phone but he insisted she come it.

So, my wife went to the doctor’s office and explained that my daughter had a rare childhood liver disease and that he had already reserved a room for her at the hospital. He explained that my daughter would need surgery first thing in the morning. This… rocked… our… world.

The next morning my daughter had a life saving surgery where they removed her gal bladder, and rerouted her intestines so that her liver would drain. They explained that this was not a permanent fix but that it was to hopefully put off the need for a liver transplant until she could get a little older. In Feb of 2015, we got the call that my daughter had a donor match available and she got a liver transplant. She’s doing amazing and we are so thankful.

What does all this have to do with living like your rich for pennies on the dollar? Well, I’ll tell you.

We spent over 10 months in hospitals, many times out of state, between the time of my daughter’s initial surgery and a few months after her transplant. It hurt us financially – really bad. In fact, we lost everything in bankruptcy. Sounds bad right? Well, in a sense, it was. Going through bankruptcy is not fun and the feelings of failure were hard to deal with as well.

But losing everything, including our debt, was freeing. We were no longer stuck in one place because we no longer had a mortgage. We could live anywhere we wanted to. And, after everything we’d been through, we needed a change of scenery for a while.

I had read a book by Tim Ferriss called the 4-hour work week where he talks about how the “new rich” live. He talks about how the “new rich” prize mobility, freedom, and experiences over money and possessions. And, I loved the way he explained it. He says that we don’t want to be rich just so that we can have millions of dollars in the bank. We want what we believe the millions of dollars in the bank could afford us to do. We work and work for years and years hoping to one day retire with enough money to enjoy ourselves. But, there are a few problems with this mentality. We don’t know if we’ll live long enough to get to retirement, we don’t know if we’ll be physically fit enough to enjoy retirement and get to do the things we want to do, and we don’t even know if the world economy will allow us to ever retire anyway.

Who’s richer?

Tom works 80 hours a week for a corporation in an office downtown and makes $100,000 dollars a year. He has no time to play golf or travel and misses many family events like his kid’s sports and birthday parties. He hopes that one day, when he’s 65 years old, to be able to have enough money to do all the things he always dreamed of doing.

Bill works 15 hours a week working for himself and makes $35,000 a year. He spends his free time traveling with his family, playing golf, and learning new languages. He doesn’t care if he ever retires because he loves his job and is doing all the things he wants to do right now.

So how do we live like the “new rich”?

Choose to do what you want to do and do it now. Enjoy your life now instead of deferring life’s greatest experiences until retirement. Here’s how you can do it…

  1. You have to be able to be mobile. Either by working for yourself or convincing your boss you are more productive working remotely.
  2. Sever ties to debts that lock you down to one location (preferably by paying them off).
  3. Play the slow seasons with rental homes.

So… once we realized we had nothing holding us where we were (no house payment) we decided to go somewhere else and try something new and experience something different. I started searching the web to understand where the slow seasons were and what times of year they were for different regions of the country.

I learned that fall through the end of winter was the slow season for rentals for many states from South Carolina northward, so I started looking at properties on VRBO.com. After a sifting through a few hundred, I found one I liked. It was 3500 square feet, on an enormous lake, with a dock, a bonus room, 4 beds, three baths… etc. During the slow season, it was $1,600 a month including utilities. During the peak season, it was $4,000 a month. I snapped it up for all the slow months.

Then, because I knew that the slow rental season in Florida was the summer, I found a condo on the beach for the summer months so I could come back and run fishing charters (I’ve been a fishing guide for 11 years). Even though summer was slow for rental houses, it was peak season for my charter business. For the past 11 years, I’ve made 75% of my annual income in the summer months. The condo rental was 45 minutes closer to the marina than the house I previously owned, it was on the water, had an awesome pool, and it was cheaper than my mortgage used to be. $1,800 a month for May-July, including utilities. If I were to rent it in the winter, it would have been $3,800 a month.

The houses are amazing and the prices are super cheap, but the best part is, we can go somewhere else if we want to. There’s nothing keeping us in one spot. No mortgage holding us hostage. I could go to Colorado in the summer, Tennessee in the winter, or any other number of states – and I can live in homes that I otherwise would never be able to afford.

You don’t want millions of dollars in the bank, you want the freedom you think those millions could afford you. If you’re after the freedom, you can have it now. It’s just takes a little lifestyle design and planning. 

I highly suggest checking out Tim Ferriss’ book, The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich. I’m not associated with it in any way, I just think it’s a really interesting read. He goes into great detail about how to “live like the new rich”. Check it out.


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  1. Mrs. Picky Pincher

    So true. You can live a rich life without the debt and stress that comes with our modern perception of a “rich life.” I prefer to live in a way that people can’t tell how much I make. 😉
    Mrs. Picky Pincher recently posted…How To Actually Help Someone Who’s GrievingMy Profile

  2. Cody @ Dollar Habits

    I’m so glad to read that your daughter is doing well now. I can’t even begin to imagine what you and your family have gone through.

    Your housing and location strategy sounds awesome. Those sound like some really great homes and the picture is amazing. Thank you for sharing your story.
    Cody @ Dollar Habits recently posted…How to Harness the Power of HabitsMy Profile

  3. FIbythecommonguy

    Awesome story and glad to hear your daughter is doing well. Talk about freedom to come and go. Are your kids in school yet? If so, how do you handle that? Do you plan to follow this path for the foreseeable future?
    FIbythecommonguy recently posted…DIY Fence BuildMy Profile

    1. MrDD

      Clay and his wife homeschool their kids. They have no plans to go back to the way they lived before.

      1. FIbythecommonguy

        Awesome and thanks for the follow up.
        FIbythecommonguy recently posted…DIY Fence BuildMy Profile

  4. Graham @ Reverse the Crush

    Excellent article!
    I’m not sure why the concept you describe in this post is so difficult to understand. I can’t fathom why anyone would want to do work they are not passionate about until they are 65 years old. I read the 4 hour work week back in 2015 and it definitely changed my way of thinking. You’re exactly right that the millions in the bank is not the goal – that does nothing for you. It’s about the freedom it provides and it’s about owning your time.

    Thanks again for sharing the great post! I am glad to hear that your daughter is doing well now! All the best to you and your family! Take care 🙂
    Graham @ Reverse the Crush recently posted…My worst investing mistakes, EVERMy Profile

  5. Mr Defined Sight

    Very moving story, thank you for sharing it with us. I’m sorry to hear about what you went through. As a dad myself, stories like this really get me. I’m glad you found a silver lining though and turned the experience to work in your favor. Very smart to take advantage of the cheaper rates during the “off seasons”. I could see myself doing something like that down the line. I wish for continued good health for your family!
    Mr Defined Sight recently posted…Hate Your Job? This Can Be A BenefitMy Profile

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