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Join us on our journey as we explore six areas of interest on The Long Strange Trip.

10/28/2026

What if we stopped waiting for a crisis to talk about death?

When a loved one enters hospice, families are often overwhelmed and forced to make difficult decisions under pressure. These conversations are much harder when no one has prepared for them.

In this week’s episode, I sat down with Traci Arieli to talk about why we need to make conversations about death more open and accessible—before a crisis hits.

🔗 Learn more: https://thelongstrangetrip.com/post/thelongstrangetrip-episode36

🎥 Watch the full video: https://youtu.be/AqqEvK5j-k8

10/27/2026

When was the last time you laughed so hard that you forgot about everything else?

Life can get heavy, and sometimes we take things so seriously that we forget to make room for laughter. But a little humor can help us break that cycle, take a breath, and see things differently.

Maybe growing older isn't about losing our sense of humor. Maybe it's about remembering to use it.

🔗 Learn More: https://thelongstrangetrip.com/post/thelongstrangetrip-episode35

▶️ Watch the full episode: https://youtu.be/VDHLxpE-OKI

10/26/2026

The worst decisions don't always look reckless. Sometimes, they look responsible.

I opened a restaurant to keep my catering crew employed through a Vermont winter. My intentions were good. I wanted to protect my people. But I skipped the simplest step: doing the math.

A good reason doesn't automatically make a good decision. Sometimes, the most responsible thing you can do is stop and question your plan before committing to it.

🔗 Learn more: https://thelongstrangetrip.com/post/the-responsible-choice-that-cost-me-50000

🎥 Watch the full episode: https://youtu.be/cSkGtIGosJo

10/23/2026

Sometimes, getting through the hardest parts of life isn't about being strong all the time.

It's about finding a reason to laugh, even when things are difficult.

Humor, reframing, and changing our perspective can help us handle life's challenges. We can't always control what happens to us, but we may have more ways to cope than we realize.

🎥 Watch the full episode: https://youtu.be/VDHLxpE-OKI

🔗 Learn More: https://thelongstrangetrip.com/post/thelongstrangetrip-episode35

10/22/2026

What's the first thing that comes to mind when you hear the word “risk”?

Danger? Caution? Or opportunity?

Here's something I've learned: sometimes, we're not really afraid of risk.

We're afraid of what happened the last time we tried something and it went sideways.

That past experience can quietly influence the decisions we make today.

But what if we stopped letting yesterday's failures decide tomorrow's possibilities?

🔗 Learn More: https://thelongstrangetrip.com/post/fear-of-risk-or-fear-of-not-changing

▶️ Watch the full episode: https://youtu.be/iMqFXD3i5rg

10/21/2026

One man told me the saddest day of his life was the day after he retired.

He woke up with no sense of purpose and no idea what to do next.

In this week’s episode, we talk about something people often overlook when planning for retirement: figuring out what will make life meaningful when work is no longer at the center of it.

Retirement isn’t just about stopping work. It’s about finding a new reason to get up in the morning.

🔗 Learn more: https://thelongstrangetrip.com/post/thelongstrangetrip-episode35

🎥 Watch the full episode: https://youtu.be/VDHLxpE-OKI

10/20/2026

What if getting older gives your brain an advantage you might not expect?

Jeanette Leardi explains long-term memory through a simple analogy: our brains are like libraries filled with everything we've learned and experienced. A younger brain may retrieve information faster, but there's more to the story when it comes to aging and wisdom.

🔗Learn more: https://thelongstrangetrip.com/post/thelongstrangetrip-episode34

🎥 Watch the full episode: https://youtu.be/qJvMlTwTFp8

10/19/2026

What's the risk of staying exactly where you are?

At 73, navigating my own cancer diagnosis, I've started looking at risk differently. Sometimes, the biggest risk isn't trying something new. It's putting off the conversations we need to have, the changes we've been thinking about, and the things we keep waiting to feel ready for.

Here's a question worth sitting with: What's the risk of not changing?

🔗 Learn More: https://thelongstrangetrip.com/post/fear-of-risk-or-fear-of-not-changing

▶️ Watch the full episode: https://youtu.be/iMqFXD3i5rg

10/16/2026

We often hear that getting older means losing our edge. But what if age also brings strengths that younger minds are still developing?

Older brains can be better at recognizing gray areas, considering exceptions, and using experience to approach problems from multiple perspectives.

That’s why bringing younger and older generations together in the workplace matters. We solve problems differently, share knowledge, and become more effective when we learn from one another.

🔗 Learn more: https://thelongstrangetrip.com/post/thelongstrangetrip-episode34

🎥 Watch the full video: https://youtu.be/qJvMlTwTFp8

10/15/2026

The messy middle is where we make some of our worst decisions.

Your old identity doesn’t fit anymore. Your new one hasn’t taken shape. You don’t know which way is up.

Josh Patrick has seen what happens when people enter this stage without preparing for the transition ahead. The hard conversations and rough plans we make before change arrives can give us something to stand on when everything feels uncertain.

And about those boats? Sometimes, the boat isn’t the answer.

🔗 Learn more: https://thelongstrangetrip.com/post/four-stages-of-transition-and-why-preparation-matters

🎥 Watch the full video: https://youtu.be/TSN0SPsqisI

Address

1233 Shelburne Road Ste E6
South Burlington, VT
05403

Telephone

+18028461264

Website

https://podcasts.apple.com/us/podcast/cracking-the-cash-flow-code/id1031040294

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