A Fun Collection of Random Thoughts You Didn’t Ask For

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I was trying to decide what to focus on in this post because I’ve had several random thoughts spending some quality time in my mind lately.

Sometimes my brain just has stuff bouncing all over the place. So I decided, why not just touch on a bunch of them?

So here we are with a mish-mosh of random thoughts all crammed into one delightful mess of a blog post!

Between the action-packed stock market real-life movie so many of us are in, our current spending, and some interesting changes we might be making to help our daughter’s financial situation for college, it’s a jam-packed post!

Plus, right now, there’s a pretty good chance we’ll be moving again. Where the heck are we going now?! Find out here, folks!

The stock market roller coaster… dum dum dummm!!

When it comes to random thoughts, I think this one has been on a lot of folks’ minds. Has anyone noticed the stock market for the past several weeks? 😉

This is probably one of the first stock market bits of craziness that I’ve been paying a little more attention to in my life. Sure, I lived through:

• Black Monday (October 19, 1987) – too young to even care
• Dotcom Bubble Crash (2000-2002) – I wasn’t paying attention to the market, but coincidentally started really investing then… I was a genius without even knowing it!
• Global Financial Crisis (2008–2009) – I was still young and naive and just kept investing… still a genius!
• COVID-19 Crash (February–March 2020) – I was a little “smarter” then and had some cash on hand, so I “bought the dip.”

But this time around has been interesting. Politics aside, there’s no doubt that we brought this one on ourselves. Sure, the market was already overpriced, but this whole tariff game has been insane and kicked off mass confusion in the stock market.

Who knows how things will turn out? I’m optimistic that the market will come back, but what do I know? I’m a glass-half-full kind of guy, so I’ll stick with that. How long could it take to come back… you never know. It could take years, or it could be back to where it was by the time this post comes out.

What makes this unique for me is that we’re not working and we’re living off our portfolio. And then I watched it wipe $250k from our portfolio in a very short amount of time. That wasn’t pleasant to see…

I use the Empower Dashboard to keep an eye on our net worth (among a ton of other features it provides). It’s a free service and works extremely well if you want to try it out.

That said, I’m surprisingly not worried about it. Although this was mostly related to the implementation of tariffs and continues to snowball as folks “cut their losses” because they’re scared of seeing their portfolios being crushed, I was expecting this. I wasn’t expecting the tariffs, but drops in the market in general should be expected. That’s how a healthy stock market works, and I knew this would happen eventually.

Fortunately, we have our portfolio structured so we can get through 5-6 years without needing to sell any stock, which takes a lot of the worry away.

I’m not a CFP or CPA or anything like that, and I can’t give advice – nor will I. But I can tell you more of the random thoughts on my mind.

My initial thoughts are that hopefully, if you’re retired and living off your investments like we are, you’ve done something similar to what we did and don’t need to do anything rash. If I were nearing retirement, I’d consider seeing how this plays out for a little bit before pulling the trigger. If I were working full-time, I’d just put my nose down and keep doing what I’m doing. It’s money I don’t need right away, so I’d just keep going through the motions of saving and investing for the long term.

This time around, we weren’t sitting on any spare cash we could have thrown in. However, I did do one thing I thought was worthwhile… I did part of our annual Roth IRA conversion early.

I normally wait until December to see how much we should convert to give us the best ACA subsidies while still converting as much as we can while staying in a lower tax bracket. But I saw an opportunity and wanted to take advantage of it.

I converted $50k from my traditional IRA (my old 401(k)) to my Roth IRA. I’m sure we’ll still do more in December, but I thought this was a good move for us to start with. There’s no selling/buying involved – it’s just a recharacterization of the funds. But converting when the market is down means we’re moving more shares for the same dollar amount – kind of like buying more at a discount. That way, when those shares recover in the Roth, all the growth happens tax-free.

So that was it for us. I know some people don’t look at what the market’s doing, but I like to see it. Since it doesn’t phase me much and I know I won’t make any rash decisions, I think that’s fine.

That said, it’s natural to feel good when you see your portfolio growing rather than going down, so I selfishly hope the market rebounds sooner rather than later!

Some strategic planning for our daughter’s college costs

Our daughter, Faith, is almost 15 and is a high school freshman as a homeschooler. She started homeschooling when we moved to Panama (the country) in 2019. At the time, this was just going to be temporary until we got settled and would enroll her in an international school.

Well, she took to it well and preferred it to regular school. And we’ve been able to appreciate it as well since it gives us the flexibility to travel when we want. So she continued homeschooling even after we moved back to Ohio in 2022.

Life is good. She does well with it… and yes, she has a social life and friends… and no, she’s not missing out on the “high school experience.”

More importantly, she’s starting to consider colleges. It’s early, and we’re not oblivious that things may change over the next few years. That said, right now she’s considering going to school in North Carolina because they have a public university that’s supposedly a great school for her planned major.

Ok, so here are my random thoughts on this… I want in. Well, I’m sure she’s not going to let me live in the dorms with her, but I’ll settle for just moving to North Carolina. Winters in Ohio… yuck. I’m ready to go now!

What’s nice is that we have a lot of flexibility as early retirees, but especially as early retirees with a low household income every year.

So we’re talking about possibly moving to North Carolina in the near future. That gets us out of Ohio (yay for me!) and drops the cost of tuition for Faith. After doing some digging, you need to be a resident of North Carolina for 12 months prior to the first day of school to be eligible for in-state tuition. And that drops the cost of tuition down a ridiculous amount.

That means we’ll likely be here in Ohio for another year or two before we make the move. It’s not set in stone, but I do like the idea. My best friend from high school lives in the vicinity of where we’d be going, which is another bonus. Plus, Justin from Root of Good lives there, so we’d be in good company!

Besides that, Faith is strongly considering a community college for the first year or two to get some of the prerequisite courses out of the way. As a North Carolina resident with a low enough income (something we can control by molding the amount of our Roth IRA conversions), she should be able to do that for free. How’s that for an incentive?!

That flexibility to mold our income by adjusting our Roth IRA conversions should also help her get some good financial aid for the regular university in NC, too. Hopefully, she’d get some grants to bring down those costs even more.

Additionally, Faith is planning on doing some online college classes through dual enrollment at Arizona State University (ASU). I talked about that in my post, Phase 1: Powerful Strategies to Earn College Credits While Homeschooling, so I’ll let you read about that there if you’re interested in learning more about that.

As icing on the cake, she’s got about $30k in her 529 plan. While a decent chunk of money, it’s not a ton, and it’s a far cry from what’s needed to cover college costs nowadays. But it’s still something and another tool in the toolbelt. Combined with the other strategies I mentioned, it’s possible she could even have a little leftover in the 529 (even though it’s a long shot). If that does happen, she could roll the leftover 529 funds into her Roth IRA.

Again, these are all just random thoughts, and it’s hard to say what will happen. Maybe everything will fall into place, and perhaps nothing will, but that’s what’s been rolling around in my head lately.

So we could be moving to North Carolina, which we’d need to do by the summer of 2027. That’s a huge benefit to me since I can’t stand the winters in Ohio. It’s no Boquete, Panama, but it’ll do for now! 🙂

Spending’s up – blame the year of travel!

One of the other random thoughts on my mind has been our spending. It’s up quite a bit lately, and that always makes me a little uneasy.

That said, I knew our spending would be higher. We’re doing a ridiculous amount of travel within a single year (December 2024 – November 2025). We’re traveling for a third of the year, which is a lot. But with how the chips fell, this all needed to be done within a year – use it or lose it.

And even though we got ridiculous deals like $3,200 for a 38-night Europe trip worth about $25k, that’s still $3,200k. It’s also one of many trips throughout the year, and each of these trips costs us something. So, while we’re traveling the world on what should be a heckuva lot more money, it’s only a fraction of the cost… but it’s still a cost.

It makes me a little anxious, even though we’re still good on the money side of the equation. But it’s tough to be a frugal spender for so many years and then make that change to spending a little more than you’re used to.

The good news is that we front-loaded most of this travel. Even though our monthly spending reports in Quicken Simplifi have been abnormally high, our spending reports for the rest of the year should be a little lower than normal. We’ll still end up with a higher-spending year than normal, but I think it won’t be too outrageous. 🤞

Lighter travel in 2026

On the flip side, 2026 is going to be a much lighter travel year. We’re planning a trip to Hawaii in February or March of 2026 to stay with good friends of mine. We’ll be traveling with some other good friends in Ohio who plan to get an Airbnb and stay for a few weeks as well. We’ll likely also stay at a place with our friends from Ohio for part of the time, too. But I’m not great with long flights (as I’ve mentioned before), so I did some research to try to “fix” this somewhat. 😉

We blew out most of our accrued points and miles on all the 2025 travel we’re doing, so we needed a new plan. I learned that we could book United business/first class flights through Turkish Airlines from Los Angeles to Hawaii for only 15-20k points per person (30-40k points round-trip). Understand that this is on a United plane – it’s just being booked through Turkish.

In other words, we’d need only 40k points per person round-trip for the fancier class of service… this is a steal! It’s one of those things that you don’t know what you don’t know. Folks in the travel rewards game are well-versed in this sort of thing, but I’m still learning this sort of minutia.

So after some more digging, I made a plan. Lisa has over 40k points in her Citi account right now – so she’s already covered for her round-trip flight. I just signed up for the Citi Strata Premier card with a 75k sign-up bonus after a $4k spend in 3 months. We’ll make sure to do $5k in spending, which will put us at 80k points – enough for round-trip flights for me and Faith as well. Cool, right?

We’ll try to complete the spending sooner rather than later, though, since there’s a finite number of business/first-class seats available for awards on each plane. Booking sooner vs later is better.

Then we’ll accrue some more miles in our Southwest accounts for the flights to LA. That will either be through regular spending on my Southwest cards or maybe by opening another card with the ability to transfer to Southwest or another airline.

Credit card travel rewards are immensely powerful and have saved us absurd amounts of money and let us travel more than we ever could have before. They’ve also provided for a better class of service on many flights and at hotels, too.

If you don’t carry any credit card balances and love the idea of traveling more for free or cheap, check out Travel Freely. It’s a completely free service I use and love that helps you track your cards, spending requirements, bonuses, and more. It provides notifications to remind you of annual fees as well as options on what to do with those cards at renewal time. And it helps you figure out the right cards to sign up for that align with your goals.

You can read more about the free service in my post, The #1 Best Way To Track Credit Card Rewards, and my Credit Card Travel Rewards page. Or you can sign up for Travel Freely here.

In addition to the Hawaii trip, we might do a vacation with Lisa’s side of the family (usually a beach or lake vacation). And Lisa and I might do a getaway for our 20th wedding anniversary next year.

So, it’s still a little bit of travel and vacations, but nothing like what we have going on currently. Although I have a feeling we’ll start getting antsy and probably end up doing a cruise at the end of 2026 or the beginning of 2027. 😂

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There you have it, my friends – just some random thoughts I’ve had that I thought I would share. If you enjoyed this post, consider signing up for the mailing list. It’s free, I keep you in the loop on the latest posts and what’s going on otherwise. Plus, I’ll send you some spreadsheet freebies I created and use routinely to make my life easier, and they could do the same for you!

Plan well, take action, and live your best life!

Thanks for reading!!

— Jim