Dan Caplinger

speaker

1,715 appearances 16 recordings 4 series first heard Oct 2023 last heard 18 Sep

Dan Caplinger’s voice in public audio — every appearance, attributed to the second.

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recordings per month · last 12 months

Recordings per month over the last 12 months — 15 in all, peaking in Nov 2025 with 3.

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Motley Fool Hidden Gems Investing · Two Retirement Experts Discuss How They’ll Decide When to Retire · 31 Jan 2026 podcast

You know, it was just as easy to stay inside and do the same work that I'd been doing for 15 years at that point.

Fast forward to now, and I mean, I've really enjoyed the past five years of work.

And so, yeah, it's been a great market in that period.

I've roughly, probably more than doubled my retirement savings in that period.

And so from a financial standpoint, like I think any financial planner would say that I'm totally set and that I shouldn't worry, but...

Nevertheless, just as I experienced earlier in my career when I was a financial planner, I was working with people who were at the age that I am now, you never feel like you have enough.

You never feel like you have everything set that you're gonna be able to account for every possible contingency that you're gonna be able to deal with whatever the uncertainty of the moment is in current events, in politics, in geopolitics, in economics, whatever it is.

And so I think that holds me back as much as anything, as well as trying to figure out, okay, yeah, I know what I'm going to do the first year of retirement, and it's going to be a blast, but am I going to really want to do that?

Am I really going to want to travel?

Am I really going to want to be away from home for 10 years?

And if that's not the case, well, geez, should I just take a one-year sabbatical and then just kind of come back to where I am?

Those are some of the questions that I'm asking myself at this point.

So I think that probably the best thing that people can do is to work with the people that they know, talk with the people that they know, either who are in that situation or who are preparing the same way that you are looking to prepare.

Talk to people who've recently retired.

Ask them, what are they doing?

And how's it been?

And has it been as good as they expected it to be?

What are the things that are better?

What are the things that aren't quite as what they expected?

What are some of the things that if they had it to do over again, they would change maybe?

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