Why the Happiest Retirees Spend Their Money Differently
Stay Wealthy Retirement Podcast
Taylor Schulte, CFP®
4.7 • 678 Ratings
🗓️ 2 April 2026
⏱️ 35 minutes
🧾️ Download transcript
Summary
Saving for retirement is one challenge.
Feeling comfortable (and confident) enough to actually enjoy it is another.
Even when the numbers say you're okay, uncertainty about the future can make it hard to use money for the things that matter most.
Today, I'm revisiting a conversation with Dr. Daniel Crosby where we talk about money, happiness, and why spending is often harder than saving.
It's especially relevant for me as my family currently navigates some big financial decisions... and a birthday trip for my oldest son that almost didn't happen. 🫣
In this episode, we discuss:
→ What the research gets wrong about the link between money and happiness
→ Why certain types of spending leave a bigger impact than others
→ A simple mindset shift that can make spending feel safer in retirement
→ What people near the end of life rarely regret—and what they wish they had done more of
This conversation is a good reminder that money is a tool, and the goal is to use it to support the life you truly value.
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Transcript
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| 0:00.0 | Welcome to another episode of the Stay Wealthy Retirement Show. I'm your host Taylor Schulte, |
| 0:05.0 | and every week I tackle the most important financial topics to help you stay wealthy in retirement. |
| 0:11.0 | And now on to the episode. My oldest son turns nine next week, and every year we give |
| 0:19.5 | our kids the same choice for their birthday. |
| 0:21.7 | They can have a party with their friends, or they can choose a family experience, something |
| 0:26.7 | fun, new, and different that we can all do together. Year after year, they choose the experience. |
| 0:32.4 | And this year, my oldest wants to go see his favorite hockey team play, the Las Vegas Golden Knights. So that's what we're doing. By the time you're listening to this, we'll be on the road headed to the entertainment capital of the world. We'll catch a game, check out the new Wizard of Oz show at the Sphere, and then we'll get outside for a hike at Red Rock Canyon before the long drive home. And as excited as we are, I'll be honest, this trip almost didn't |
| 0:55.9 | happen. Like many of you, we're in the middle of making some very big financial decisions right |
| 1:00.6 | now. We're actually in the process of buying a new home, which means navigating high prices, |
| 1:05.0 | higher interest rates, and just the general financial pressure and stress that comes with all |
| 1:09.4 | of it. And I had this very loud |
| 1:11.4 | financial planner voice in my head saying, maybe we don't offer a family experience this year. |
| 1:16.7 | Maybe we just stay home, nudge him toward a simple party with his friends, and save the money. |
| 1:21.7 | Which on paper sounds like the responsible thing to do. But here's the thing. Spending money on experiences with our kids, |
| 1:29.2 | creating memories together, cherishing this time while they're young and still choosing us over |
| 1:33.8 | their friends, that's something my wife and I genuinely value and something we've made clear to |
| 1:38.7 | each other that we want to prioritize. And I don't want to let the fear of spending or the stress of a |
| 1:43.9 | big financial decision rob us of that. When I took a want to let the fear of spending or the stress of a big financial |
| 1:44.4 | decision rob us of that. When I took a step back, I reflected on something that today's guest |
| 1:49.5 | Daniel Crosby talks about in this conversation. He explains that money does a really good job |
| 1:55.6 | of helping us avoid pain, paying for housing, food, security, all the basics. But beyond that, how we spend money |
| 2:03.7 | starts to matter a lot more than how much we have. And one of the most powerful ways to use money |
... |
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