Artwork for podcast Wisdom-Trek © - Archive 1
Day 259 – Why Doesn’t Anyone Ever Feel Rich or Happy?
14th February 2016 • Wisdom-Trek © - Archive 1 • H. Guthrie Chamberlain, III
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Wisdom-Trek / Creating a Legacy

Welcome to Day 259 of our Wisdom-Trek, and thank you for joining me.

This is Guthrie Chamberlain, Your Guide to Wisdom

Why Doesn’t Anyone Ever Feel Rich or Happy?

Thank you for joining us for our 7 days a week, 7 minutes of wisdom podcast. This is Day 259 of our trek, and yesterday we hiked the trail of The Wisdom of Being Teachable. Today we will explore why it seems that no one really feels rich or happy. I discovered this short story on Jeff Haden’s blog, and I feel it is worth sharing. If you miss any of our Wisdom-Trek episodes, please go to to listen to them and read the daily journal.

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We are recording our podcast from our studio at Home2 in Charlotte, North Carolina. As mentioned previously, we will be in Arizona for 4 days, so I am recording some additional podcasts ahead of time for while we are away. These days may be somewhat shorter as we will take quick daily treks on some short trails.

Let’s head out on the trail for today and learn…

Why Doesn’t Anyone Ever Feel Rich Or Happy?

One day I’d like to meet someone who is actually rich. Sometimes I think I’ve found one, but it always turns out I’m wrong. No matter how rich I assumed the person to be, within a few minutes I find out just how “poor” that person really is.

Take the guy who sold his company for more than $40 million. (Well, actually $100 million in total; $40 million is his share.) I was sure he was rich. Then he told me how for tax and estate planning purposes he had structured the disbursement of funds over 10 years. So sure, on paper he may be “worth” $40 million, but he only gets around $4 million each year. And despite all that nifty financial planning the taxes are still so high he doesn’t see nearly that much. It’s a bummer.


Another example is the guy who just splashed a cool $450 grand on a Lexus LFA with the Nürburgring package. His everyday car is a Porsche 911 Turbo S. I was sure he was rich. Then he told me what he wants most in life is a Bugatti Veyron only they cost about $2 million. Sure, he has money he said, but he doesn’t have that kind of money. He thinks about it all the time. It’s a bummer.

Then there is the guy with the 110-foot yacht. Strictly speaking, it’s a ship not a boat since it’s big enough to carry several small boats and a couple of jet skis on a platform at the stern. And, it has a pool. I was sure he was rich. Then he told me how expensive the yacht is just to own: fixed costs like cleaning, upkeep, dock fees, and crew run over six figures a year. And what about the expense of actually taking it for a cruise? He told me firing it up is so expensive he sometimes has to think twice about whether to take it out of the harbor. It’s a bummer.


How about the story of the guy who – I know it’s a cliché, but it’s still true – started a company in his garage, financing it with credit cards and a loan from his father-in-law. A couple decades later his company owns its building (and a few more), employs 500 people, and generates tens of millions in annual revenue. He put his three kids through Ivy League schools and then gave them significant seed money to start their own businesses. I was sure he was rich. Then he explained how he still has to work 60- to 70-hour weeks and can maybe take one week of vacation a year. Sure, he would like to have more free time, but running a company that size requires constant and total attention. Why it could all go away in an instant, he said. And then what would happen to his family? The very thought makes him shudder. It’s a bummer.


So I decided to set my sights on a different target. By definition there can’t be that many rich people; maybe statistical probability was the problem? So I decided to look for someone who is happy. After all, not everyone can be rich, but anyone can be happy.

I thought I found one when I met an entrepreneur who had just landed her first big customer. And, it was not just a big customer, a truly enabling customer – one who made it possible for her to hire much-needed employees, make long-delayed equipment purchases, and finally get creditors off her back. I figured that surely made her feel happy.

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Then she told me how much she hates to recruit and interview…and actually having to supervise those employees on a daily basis? Ugh. She told me how adding equipment, maintaining a larger inventory, and managing the huge increase in production was such a pain. “Don’t get her wrong,” she told me as she looked around to make sure no one overheard, “but she often longs for the good old days when life was a lot simpler.” It’s kind of a bummer.


Another example is the guy who, after years of putting out feelers and constant hints, was finally invited to serve on the board of a startup. The company has potential, he said, but it’s not Twitter or Facebook or even Fancy. Now serving on one of those boards would be cool. This? He thought it would be fun, but it’s kind of a bummer.

Then there is the gal who just bought a bigger house? Bummed because it takes so much work to clean. The guy who just doubled his income? Bummed because now his taxes are higher. The gal who just landed her dream job? Bummed because now her daily commute is half an hour longer.


Seems no one I meet, no matter how much money or success they’ve achieved, is actually rich, not really. And although I’m stretching the premise to make a point, it seems no one I meet, no matter how fulfilling and gratifying their life might be, is actually happy, not really.

But that’s okay. I’ll keep looking. Someday I might find someone. And hopefully, that someone is you.


The moral of this story is anytime we place our financial confidence and personal happiness on earthly resources, we will never have enough and never be happy. If you are not content and happy where you are today with what you currently have, you will never be content or happy with more.

The 1st letter that the Apostle Paul wrote to understudy Timothy gave us the solution if you don’t consider yourself wealthy it is found in 1 Timothy 6:6-8, “Yet true godliness with contentment is itself great wealth. After all, we brought nothing with us when we came into the world, and we can’t take anything with us when we leave it. So if we have enough food and clothing, let us be content.”


If God has allowed you to obtain wealth in this world, the key to a life that is happy and full of joy is in 1 Timothy 6:17-18, “Teach those who are rich in this world not to be proud and not to trust in their money, which is so unreliable. Their trust should be in God, who richly gives us all we need for our enjoyment. Tell them to use their money to do good. They should be rich in good works and generous to those in need, always being ready to share with others.”

Let me ask you another question. When will you be content with what you have? What will make you happy? Tomorrow we will be back on the trails as we explore another short story. So, encourage your friends and family to join us and then come along tomorrow for another day of our Wisdom-Trek, Creating a Legacy.


That will finish our podcast for today. As you enjoy your daily dose of wisdom, I encourage you to help us promote Wisdom-Trek in the following four ways:

  1. Leave us feedback about the podcast on, so we can continually improve.
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Thank you for allowing me to be your guide, mentor, and most of all your friend as I serve you through the Wisdom-Trek podcast and journal each day.

As we take this trek together, let us always:

  1. Live Abundantly (Fully)
  2. Love Unconditionally
  3. Listen Intentionally
  4. Learn Continuously
  5. Lend to others Generously
  6. Lead with Integrity
  7. Leave a Living Legacy Each Day

This is Guthrie Chamberlain reminding you to Keep Moving Forward, Enjoy Your Journey, and Create a Great Day Every Day! See you tomorrow!