Dan Caplinger

And, you know, we talk about these plans and it's kind of like, well, do you want to travel with me?

And the answer is sometimes yes, but probably not as much as I want to.

And so at least for now, she's comfortable with the idea of kind of even if I were to go to a full retirement, she'd be comfortable working and continuing to do the health insurance stuff.

Yeah.

You know, that's another one of those uncertainties, though, that comes up because right now, if we retired, I live in Massachusetts.

We have the Obamacare coverage.

And even before Obamacare was around, the state had its own health care exchange.

And so that's an option for us.

It's a really expensive option.

the coverage under her job is a lot more affordable.

And so that's a big question that comes up is sort of like, okay, if I stop doing what I'm doing, like, do I want to go full retirement or do I maybe want to do something else?

Like get another job that might, I don't have to worry about the financial aspect of it as much.

I don't have to maximize my salary anymore, but just getting something for those benefits might actually be

The most important part, because it's a natural thing, the health care expenses tend to go up.

This is kind of the most vulnerable time in my late 50s and early 60s before I'm eligible for Medicare.

That's the biggest threat to my financial situation is an unexpected health situation.

Well, boy, I hesitate to say retire because I kind of feel like I'm almost like one of the friend that you were mentioning before, where it's more like it's going to be a transition more than a retirement.

And so, you know, I really hope that I'm spending my time doing something, whether it's paid work, whether it's volunteering, whether it's something that makes a difference, need to make a difference somehow.

But I will tell you this, there is a natural transition point coming up this year in 2026.

It's my 20th Fooliversary as a contractor is May 31st, 2026.