Josh vs. Gravity: What a Canadian Go-Kart Ride Taught Us About Retirement

What do go-karts, glacier water, and retirement planning have in common? Quite a lot, if you’re Josh Bretl. In this fun and insightful episode of The Own Your Retirement Show, Josh and co-host Mark Elliott take you on two journeys at once: one through the scenic Canadian Rockies and the other through the winding (and sometimes bumpy) road to retirement.

The show kicks off with Josh sharing a recent family vacation that started in Banff National Park. Picture breathtaking mountain views, pristine lakes, and even a baby black bear sighting just ten feet away. If you’re wondering what this has to do with money—just wait. As Josh recounts the highlights of the trip, from drinking glacier water to surviving a family go-kart adventure on a retired Olympic ski slope, it’s clear that this is more than just a travel log. It’s a window into what matters most in retirement: making memories, staying adventurous, and knowing your finances are handled so you can enjoy the ride.

Josh’s family discovered a new thrill in “downhill carting”—a kind of gravity-powered go-kart course originally built for the 1988 Calgary Olympics. It’s a perfect metaphor for what happens when you retire. You go from the uphill climb of saving and working to the downhill flow of spending and enjoying. But, just like the cart track, that downhill ride requires balance, awareness, and a plan so you don’t end up on two wheels in the rain (literally, in Josh’s son’s case).

From there, the conversation shifts gears into what Josh calls “the four big questions every retiree needs to answer.” These aren’t just hypotheticals—they’re the backbone of any solid retirement plan. And if you’re like most people, you’ve asked yourself at least one (if not all) of them:

1. When can I retire?
2. Have I saved enough?
3. Will my money last?
4. Will my loved ones be okay if something happens to me?

Each question may sound simple, but unpacking them reveals layers of financial, emotional, and even psychological factors.

✅ “When Can I Retire?” Isn’t Just About the Numbers

Josh explains that knowing when you can retire isn’t only about your 401(k) balance. It’s about what you want retirement to look like and how emotionally ready you are to stop working. For some, work provides structure, social interaction, or even a sense of purpose. Retirement is a financial decision, yes—but it’s also a lifestyle decision.

He shares the wisdom of his own father: “It’s better to be able to retire than to actually retire.” That’s because once you know you have the option, you’re no longer working out of necessity—you’re working because you want to. That’s a powerful shift in mindset.

Some people choose to ease into retirement by cutting back hours or starting a second-act career. Whether it’s becoming a golf course ranger, working at Home Depot, or going back to school to become a physical therapist (like one of Josh’s clients did in his 60s!), retirement doesn’t have to be all-or-nothing.

💰 “Have I Saved Enough?” Depends on What You Spend

This is one of the most frequently asked questions Josh and the FSR team hear—and one of the trickiest to answer without context. As Josh puts it, “We have to back into that number. What do you spend? What income sources do you have coming in? Then we do the math.”

A couple spending $5,000/month in retirement will need far less saved than one spending $10,000/month. Add in variables like pensions or Social Security, and the numbers change again. For example, a household spending $10,000/month but receiving $6,000 from Social Security and pensions only needs to generate $4,000 from savings. But if Social Security is your only guaranteed income source, your savings must carry a much heavier load.

Josh introduces the idea of “guaranteed income”—sources you can’t turn off, like Social Security, pensions, and certain types of annuities. Everything else—from brokerage accounts to retirement savings—has to be managed and drawn down smartly to fill the gap.

📉 “Will My Money Last?” Tackles the Big Retirement Risks

Here’s where things get real. Retirement is no longer about growing your wealth; it’s about protecting it and using it wisely. Josh outlines three major risks that can derail a retiree’s finances:

1. Healthcare and long-term care costs
   • A healthy 65-year-old couple today may need over $300,000 for medical expenses over their lifetime—and that doesn’t include long-term care.
   • Medicare doesn’t cover everything, and traditional long-term care insurance is expensive and hard to get. Hybrid solutions—such as asset-based policies—offer flexible coverage with better outcomes.
2. Market volatility and sequence of returns risk
   • When you’re withdrawing money in retirement, a down market can hurt you much more than it did while you were still working.
   • One client, John, told Josh he didn’t even open his statements during the 2008 crisis because he knew he had time to recover. But now? He doesn’t want to take those chances. Retirement investing is about managing volatility, not chasing returns.
3. Taxes—arguably the most overlooked threat
   • Josh gets into full-on “tax nerd” mode explaining why rising tax rates are a major concern.
   • Most retirees have saved in tax-deferred accounts like 401(k)s and IRAs. That means the government gets a cut—eventually.
   • Required Minimum Distributions (RMDs) force you to take money out starting at age 73 (or 75 for some), whether you need it or not. That could push you into a higher tax bracket.
   • Roth conversions—paying tax now to avoid bigger taxes later—can be a strategic move if done wisely.

🧭 “Will My Loved Ones Be Okay?” Means Planning for the Unexpected

This is the question nobody wants to think about—but everyone needs to. If something happens to you, will your spouse, kids, or grandkids be okay? Do they know where your money is, how to access it, or what your wishes are?

Estate planning isn’t just for millionaires. Josh calls it the “most godawful” part of the process—not because it’s difficult, but because no one likes thinking about worst-case scenarios. Still, it’s crucial.

Proper estate and legacy planning ensures:

• Your spouse knows how to maintain income streams
• Assets go where you want them to
• Children with special needs are protected
• Taxes and legal headaches are minimized

Even if your estate is modest, having a will, a power of attorney, and a plan makes a world of difference.

💬 Real Listener Questions (and Smart Answers)

The episode wraps up with a listener mailbag segment featuring real-world questions from folks facing retirement right now. Topics include:

• New inheritance tax rules for IRAs (thanks to the SECURE Act)
• Whether or not to use a financial advisor when you’ve been managing money on your own
• How much tax to withhold from retirement withdrawals
• What to do with an extra $3,000/month now that the mortgage is paid off

Each question is met with clarity, empathy, and a healthy dose of common sense. And like everything Josh and Mark do on the show, it’s explained in a way that makes sense—even if you’re not a finance person.

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✨ Final Thoughts

This episode is a perfect blend of family, finances, and fun. Whether it’s Josh’s kids nearly flipping their go-karts or retirees trying to navigate RMDs and Roth conversions, it all comes back to preparation, perspective, and having the right team in your corner.

If you’ve ever asked yourself one of those four big retirement questions, this episode is for you. You’ll walk away with practical ideas, maybe a few laughs, and a better sense of what it takes to confidently own your retirement.

📞 Ready to talk? Call (630) 478-9599 to schedule your complimentary 15-minute call with an FSR advisor.