Tales & Trails of a Traveling Wiseguy

Earlier today I posted my personal reflections on the past year. I dubbed it 2025: A Year of Waiting. That post wasn't all of my personal reflections, though. It was just one part. It turned out after I wrote and edited the part on how 2025 was the year of Being Sick Sucks— a tag I attached to 47 posts last year— I felt so down I needed a break from writing. I didn't want to risk that this retrospective gets stuck in my WIP queue for another few days, though, so I published what I had. I planned to come back with the rest later. Later's now.



The thing about Waiting... as a theme is that it has both negative aspects as well as... not-so-negative (I can't quite bring myself to say positive) aspects.

The negative kind of waiting comes with all the things that are beyond our control. Like, do I get sick with a virus despite generally being safe and smart about hygiene? How long does that virus take to run its course? How long does my wife's recovery from a planned surgery take? How many complications happen along the way, each setting her back two weeks or more, through no fault of her own? All we can do with these is keep waiting, and keep pushing out our expectations for how long we'll be waiting.

On the other hand there's the type of waiting that comes with a situation where we have some control. We set ourselves up as best we can for the long term, then navigate through the complications and changes thrown our way. Though there can be frustrating setbacks, overall it is fulfilling to nurture the plan to its fruition. Planning with money is one of these situations.

Money: I Planned Patiently, and Now I'm There!

Years ago I started repeating the mantra Five Good Years. Hawk and I did a budgeting exercise to figure out how much money we'd need to spend on a monthly basis in retirement. We included things other people often overlook when they do this as a kitchen table budgeting exercise: health insurance costs, maintenance and insurance on the house and cars, costs for replacing cars every several years, and of course, the costs of living the active lifestyles we'd like to keep.

Once I had the cost side of the budget I worked on the income side. I used my models of an investment portfolio to figure out how much we'd need in the bank to generate cash flow to fund our expenses.

It was much too early to retire then, of course. But it wasn't a Y/N question. It was a matter of when.

And that's where I started saying Five Good Years. Because from what we had then, I estimated that it would take five good years— meaning, five good years of stock market returns— to get us to our goal.

Of course, Five Good Years seldom happen all in a row. I knew that when I started saying it. I figured Five Good Years would actually take 7 years. There'd be a downturn and recovery in the market cycle somewhere in the middle.

As it turns out, Five Good Years took 10 years. I coined the Five Good Years mantra in... checks blog... April 2015. And it was around September 2025 that we reached our target number.

Why the difference, BTW? Why 10 years instead of my forecast 7? Two things. First, unanticipated disruptions gave us more not-good years than I expected. Hawk had two long periods out of work. Second, we had to raise our target number significantly. Even though I accounted for inflation in my model, high rates of inflation not seen in 40+ years kicked in in the early 2020s. Over the past 5 years the cost of many grocery staples have doubled. Property insurance has increased 10+% YoY multiple times. And health insurance, which was already one of the largest line items in our retirement budget, has rocketed up in cost at 2-3x the rate of inflation for 10 years.

These setback aside, the good news is we reached our financial goal in 2025.

The less good news is, I feel a bit like the proverbial dog that chases cars and finally caught one and now isn't sure what to do with it.

Career: Way too Little, Much too Late

Another aspect in life where I've been waiting for many years is my career. I've been waiting for opportunity for advancement to come to fruition.

While waiting I've suffered numerous setbacks over the years. And this year there were even more setbacks.

Early in the year, in January 2025, my company had a big layoff. IMO it was poorly strategized and poorly executed. And that wasn't just my opinion. It was so bad that a lot of good people said, "Fuck it, I'm out," and quit of their own accord. Then in September there was another layoff. That one left us too short-staffed to complete all the work tasked to us in our compensation plan.

Along the way my boss has been saying earnest things about helping me build my career. But at this point it's way too little and way too late. Even if I wasn't already financially at the point of saying, "I'm outta here!" just the fact that it feels like he's shuffling deck chairs on the Titanic while telling me he'll help get me promoted would make me prefer to look elsewhere for my next opportunity anyway.

Our Costco dividend check arrived this week. It's for $55.50. That's less than last year's $68 rebate and way less than the nearly $114 we earned in 2023. But still, $55 is nice, right? Welllll....

This $55.50 isn't free money. We paid to get this money. We paid $60 for Costco Executive Membership. So we actually lost $4.50!



This rebate is the big selling point of executive membership. Costco charges an extra $65 (now; up from $60 last year) for this elite tier of membership and, in return, gives you 2% back on all Costco purchases, except gasoline.

I'm sure for many families it's a win. I know because I see them in the checkout lines with their carts full to the rim. Meanwhile we virtually never have more than 1 layer of items resting in our cart. The previous two years we came out ahead on the deal. This year we paid our money and came out a bit short.

Coincidentally our Costco membership is up for renewal right now. I'm of two minds about whether to re-up at the executive level.

• On the one hand, it wasn't worth it this year. We lost a few dollars. Even last year, it didn't pay off hugely. We only netted $8 on the deal.


• On the other hand, coming up $4.50 short at the end of the year isn't anything to get upset about. It's not even milkshake money nowadays. And maybe next year we'll earn more. Though the ante has been raised. Membership is now $65 for basic tier plus an extra $65 for executive.

Right now I think I'm leaning toward renewing. There is one perk to executive membership I'm eager to try out.... Executive members get earlier shopping hours at Costco! 🤣 I haven't availed myself of that elites-only benefits yet— mostly because every time I've planned on doing it I decided I'd rather sleep in instead and deal with the crowds at the store later in the day. 🤣 But maybe this coming year I'll drag myself out of bed early to play Let's Go Shopping!

It's time for another chapter in the story mystery of the church up the hill. This is now part 3 of the story. Originally I had thought I'd be able to fit it all in one journal entry but as I started writing the story it grew. It grew first from one blog to three. Then as I took a slight detour into writing about AI and photography in part 2 I realized the story will take 4, maybe 5, chapters to complete.

As I noted in the previous chapter, my dad lost his job when I was a little kid. The retail chain he worked for went out of business.



Dad's job wasn't a great job. The hours were brutal. As a store manager he was salaried, not hourly, so he didn't get paid for his extra work. And extra work was required every time a store employee called in sick and no substitute could be found, and every time there was a break-in afterhours and the alarm company and the police called. The way my mom told the story, years later, break-in attempts happened regularly, like at least once a month. The store was in a rough neighborhood.

Dad's job wasn't a great job, but at least it paid the bills. I think. Then he lost the job, with little or warning.

This was the mid 1970s. As I noted in the previous chapter, the economy sucked. Technically the US had just pulled out of its worst recession since the Great Depression, but hiring had not yet resumed. I imagine younger folks today who lived through the jobless recovery of the Great Recession in the late 00s understand the pattern.

Speaking of younger generations and modern patterns, my parents in the mid 1970s did something that's familiar to a younger generation today: they hustled. With "real" jobs not really hiring, my parents both took on whatever odd jobs they could find. Between hustling and scrimping and borrowing, they kept a roof over our heads and food on the table.



This is where some of my earliest memories meld in with the stories my parents later told. Oddly I don't remember my parents being stressed around that time, or unhappy. Probably that's because I was too young to recognize such emotions. It could also be that my parents hid their stress and worries well from us younger kids. One snapshot memory I do have from back then is my parents giving each other a high five when my mom said, "We did it! We paid the mortgage this month."

I also have early memories of some of the jobs my parents did during that time of hustling. My mom started selling Tupperware. Many of my earliest memories are of riding with her in the car as she drove back and forth to the Tupperware warehouse. We'd return with a suitcase full of products she'd sell via Tupperware parties.



I wish I could say that Tupperware was how my parents pulled out of the economic nosedive after my dad lost his job. I wish I could say that Tupperware was how my mom built  a lasting and fulfilling career as an entrepreneur— which was part of the Women's Liberation pitch Tupperware was making back in the 1970s. Alas, I'm not sure my mom ever made any money with Tupperware.

That's because Tupperware was, for many years, a multi-level marketing (MLM) organization. In MLMs most distributors make very little money. See Wikipedia's Tupperware page, for example.

Mom stopped selling Tupperware after a short period of time. Likely that's because she netted little or no money after a lot of work— work planning and presenting at Tupperware parties, hustling to get people to place orders (remember, in a tough economy), then having to pick up & deliver the orders once they were shipped to the local warehouse. But while the dream of making it a sustainable career disappeared quickly, the Tupperware itself did not. Mom bought a number of pieces herself, because they were useful. And they lasted. The bright, 1970s vintage colors and those fluted lids were a mainstay in our house for many years after.

To be continued....

Phoenix Getaway travelog #2
SJC Airport · Sat, 20 Sep 2025. 9am

Over my past several trips via SJC airport I've found that parking in the hourly lot next to the terminal can be a win. Yeah, it's not cheap at $31/day or $26 with a reservation a few days in advance. But when the cost of Uber/Lyft to the airport runs from $30 to $40+ each way, parking is a win, cost-wise, on short trips. Plus, time-wise, driving and parking means I control the schedule; no waiting on drivers who are slow to arrive or get reassigned and starting the process over from "Please wake up and start driving toward me" after I've already been waiting several minutes. And sometimes I've been able to park really close to the terminal. Alas today was not one of those days.



Paying to park in this lot is a gamble. It's a gamble because the lot is long and narrow. The long axis stretches directly away from the terminal. So if you luck into a spot near the front, it's a quick walk to the building. If you luck into the lot being 99% full with everything close already filled up.... Well, the spot I got today was 4 spaces from the far end.



It's a long walk to the terminal at the other end.

And for this I'm paying $104— $26/day times 4 days. I took the gamble on parking here for a 4 day trip because I figured it was worth a little something extra for Hawk with her broken toe not to have to depend on Uber/Lyft, which can occasionally be weird. Well, it's a good thing I dropped her at the terminal first, because walking from here would've been a no-go for her.



Oh, and there was a cheaper lot I could have booked my reservation in. The lot across the street would've been $80 total, $24 cheaper. And note that the worst spaces in that lot are still not as far out as where I'm parked here. And I wouldn't even have had to park at the far end of that lot.... It's less than 2/3 full.

You pays your money and you takes your chances.

Canada travelog #2
Mississauga, ON · Sat, 23 Aug 2025. 8am.

We landed at YYZ airport (yes, that's really the IATA code for Toronto's airport) this morning at 6:43am local time. Our flight from San Francisco was just over 4.5 hours from takeoff to landing. And on this red-eye I managed to sleep pretty much the whole time. I was already nodding off before we were wheels-up at SFO and, except for being awoken by announcements on approach and falling back asleep, I basically didn't wake up until we were taxiing at YYZ. Those first class seats we sprung for sure helped.

Once off the aircraft and and in the terminal, it was the standard old airport shuttle, international style, I became familiar with years ago. Hike up ramps and escalators to a long, empty corridor. Trek seemingly a mile in that corridor, because the flight always lands at the far end from passport control. Wait in line for passport control— except with modernization in digital entry there's barely a line anymore. But the lack of wait there just means there's more wait now at baggage claim. Remember, those bags have to travel a mile from the aircraft, too! 🤣 Then collect your bags, pass the basically rubber-stamp customs check, and exit into the arrivals hall.

Once in the arrivals hall I decided to take a moment to try my luck with an ATM. I say "try my luck" because I'm still salty about getting raked by a cooked exchange rate at an airport ATM in Italy. Wise to that experience, I spotted where this Canadian ATM tried to do the same thing, asking me to confirm a bogus exchange rate. I said NO, expecting to cancel the transaction. But then a funny thing happened. I got cash.



"WTF! I said NO to cancel and they charged me anyway?" I fumed. I resolved to check my bank balance later to see how badly they raked me. Recall when this happened in Italy, there was a whopping 15% vig in addition to the €4.50 flat fee service charge. Here there was also a C$4.50 flat fee, but at least my credit union refunds such charges.

When we had some quiet time a bit later in the morning (after picking up our rental car, driving to the hotel where my brother-in-law is staying, and waiting for him to shower, dress, and meet us in the lobby to go out for breakfast together) I found another surprise. I looked up my bank balance details and saw that the transaction had gone through at the fair exchange rate.

WTF? In polite Canada you can just say "NO" to highway robbery by a bank ATM and... not get robbed?!

Chicago Trip Log #7
Back Home - Thu, 13 Aug 2025, 11:20pm

Leaving Chicago this afternoon/evening was a comedy of errors. Kind of like the movie namesake of my tag for traveling— Planes, Trains, and Automobiles— aspects of getting from point A to B to C that should have been straightforward went awry.

The first frustrating miscue was it taking forever to get a Lyft ride. The app showed drivers within 1.5 blocks of the hotel, but then matched me to a driver 9 minutes away who still had a passenger to drop off first. "There's no way in downtown Chicago at rush hour the closest driver is 9 minutes away," a local friend of mine quipped. Then when that driver got as close as 6 minutes away, Boom! They switched me to a new driver. Who was 13 minutes away and still had to drop off a passenger.

"That's bullshit," my colleague opined. "I'd cancel and try again." So I did. And got matched to another driver 9 minutes away. I decided to stick with that as it seemed like the best I was going to get unless I wanted to pay a lot more.

Then my driver got lost. In downtown Chicago. Meeting me in front of an 80-floor skyscraper. So not exactly a hard-to-find address! Except obviously it was. The driver made wrong turns and had to circle around not once, nor even twice, but three times. I thought about cancelling again but didn't want to go to the back of the 13 minute queue.

Ultimately it took 25 minutes from when I first called for a car until one arrived. Then the ride took 55 minutes due to traffic. 80 minutes total... and if I'd walked to the train, it would've taken about 50 minutes for the same trip. And cost about 1/25th as much.

Paying a lot more for a ride instead of using transit

As an aside, I was planning to walk & ride the train until the last minute. I figured the timing of transit versus a car ride was favorable— which is often very much not true—and saving the company money was an act of good corporate citizenship. What changed my mind was that same colleague I mentioned above who openly laughed at my "save the company money as a good corporate citizen" line.

"It's not like it's your money," she began. Then after I used that citizenship line she laughed and told me about a few examples she's seen recently of managers in our organization running up huge bar tabs and expensing them. "All they did was get themselves drunk. They didn't accomplish anything necessary, like getting themselves to the airport. And they had zero hesitation."

Put in perspective against pouring $100 down my throat, paying $70 for a ride instead of $2.50 for the train was a reasonable business expense.

The usual with Southwest

I'm flying Southwest this trip, so you know what happened once I got to the airport.



Yup, my flight was delayed.

Delays actually started appearing via notifications on my phone a few hours earlier. I ignored them earlier in the day, figuring the actual delay would be fluid until the aircraft serving my flight left its previous station.

Even once I was at the airport, and my scheduled flight time was just 2 hours away, the delay kept moving around. The flight was 10 minutes late. Then 30. Then 45. Then on time. Then 10 minutes late. Once it actually left its previous station 25 minutes late, it stabilized— it would be 25 minutes late. Like I said.

The weird thing, though, was despite Southwest showing a 25 minute late departure they claimed we'd actually arrive a few minutes early in San Jose. Yeah, I didn't believe that either.

Thankfully once our flight was ready for boarding the day's comedy of errors was over. The flight went smoothly. There were lots of empty seats, so I enjoyed an exit-row seat with an empty middle next to me. With two free drinks thrown in thanks to my elite status, it was almost like flying first class.

Ultimately we arrived just 10 minutes late. Not bad. And once we were on the ground at SJC I used my finely tuned skills at timing calling a ride so that a driver was pulling up to the curb just as I got to the ride-hailing area outside the terminal. I walked through my own front door right at 11:00pm, just 30 minutes after the flight touched down.

Frequent flying blogger Gary Leff posted a blog Sunday on his View From The Wing (VFTW) website, "Amex CEO Admits: ‘We Made Benefits Hard To Use On Purpose’". As a person who's been playing the game of milking credit cards for airline/hotel points and benefits for years I found none of it surprising. I've noticed the changes Amex CEO Steve Squeri is referring to, even if he was saying the quiet part out loud.

For example, when I opened a costly new Amex Hilton card a few months ago I thought really hard about whether the newly raised $550 annual fee would be worth it. Yes, the card has more benefits that ever before, in absolute terms; but those benefits are structured in ways that limit them and make them more difficult to use. And Amex Hilton is hardly the only card making these kinds of changes. It's happening broadly across American Express, of course, but also with its main competitor in the points-and-loyalty space, Chase.

I'm not the only person for whom Leff's blog is more of a "Well, duh" moment than a wakeup call. From my reading on sites like FlyerTalk.com I'd say that most people who are serious players of the points credit card game have been seeing these changes coming. Cards are getting to the point where there is value there, if you fit the right profile of being able to use enough of the benefits, but the value is so close to break-even that it's arguably not worth pursuing anymore.

Is the airline/hotel loyalty credit card gravy train coming to an end? Could be. If so, it was fun while it lasted. Maybe soon I'll just use my 2% cash-back cards all the time.

I haven't even caught up with my backlog of blogs from our trip to Italy last week (they're held up on my time to deal with touching up photos) but already I'm ready with a retrospective. Here are Five Things:

1. Despite a few frustrations around the edges of the trip and a few things that went wrong with the parts my company planned, I very much appreciate being named to Club and getting to go on this trip. There were times I grumbled (privately), Maybe I should skip this trip and plan my own. Well, that would've been expensive. Just the flights alone would've cost us $5,000. The three hotel nights that were included plus the food and misc. expenses were worth another $2,500.


2. The highlight of the trip was our 2½ days in Rome. This was a side-trip we planned— and mostly paid for— on our own. (The Company let us book a stopover on the flights they paid for.) We hired private tours for the Colosseum, ruins of Caesar's palace, the Roman Forum, and Vatican City (the part that's still in my backlog), and augmented that with trekking to the Spanish Steps, the Trevi Fountain, and the Pantheon (also in backlog) on our own.


3. Hiring private tour guides was expensive, eye-wateringly expensive in the case of the Vatican tour, which cost us over $1,200, but there's real value in it. With guides we saved the time of having to do lots of research and planning ourselves, we avoided waiting in lines and wandering around trying to figure out where to go, and we had someone who helped us ensure we saw the best things we could. Yeah, we could have cut the costs maybe in half by booking group tours instead, but we've had mixed experiences with even smaller, 12 person sized group tours. When time's limited, when it might be years, if ever, before you go back to that place again, go big.


4. Our "beach" resort stay, the part paid for by the company, reminded me that when you're at the beach there's an enormous different in really being at the beach. If you can't just walk out the door of the building, across a pool area, and be on the sand, you might as well stay a few miles away and drive to the beach. At the resort in Chia, Sardinia, it literally was a drive; the beach was 4km away from the resort hotel! As a consequence we went to the beach just once. We could have had more fun going back to our favorite splashy pool resort in Phoenix instead.


5. As much fun as visiting Italy/Rome was, and as little a fraction of the whole as we saw, we're kind of done with it. We're definitely not feeling, "Ooh, let's plan another trip to Rome!" Partly that's because we saw the highlights we cared about; partly it's because there's so much else in the world we want to see, too! I could see returning to Italy specifically for Pompeii, to see the ruins; Venice, for its unique canals; and maybe Florence, for its Renaissance architecture. But I don't think I'd want to spend more than a few days in each.

You know your relationship with someone is bad when you find yourself doing the math to answer the question, How much longer until I can quit these clowns? In this case the clowns are my mortgage company, and "quit" means pay off my mortgage so I can be done with them.

I've noted before that I don't like my current mortgage company. My loan has been sold a few times, starting from the originator, whom I genuinely liked. Then it was sold from Originating Lender A to New Bank B. Bank B worked fine when everything could be automated but was a pain in the neck to deal with every single time the computers kicked out an exception that required human intervention. Now Scumbag Debt Collector C— yes, my new mortgage servicer is a scummy debt collector— pisses me off with every single communication they send me because, well, they're a debt collector. All their processes as they try to move into mortgage servicing still read like they're a debt collector, treating me like a deadbeat borrower who's fallen behind on payments.

The answer, BTW, is 6½ years. In another 6.5 years of steady monthly payments I'll have this loan paid off.

Could I be done with these clowns sooner? Oh hell yes! I could increase my monthly payments to retire the debt sooner. Hell, I could just write a check to pay off the balance. The whole balance. It's not that big anymore. I've been paying down the mortgage for 20+ years and have never taken cash out on refinancing.

Of course, just because the balance "is not that big" doesn't mean I have that kind of cash sitting around. I'd have sell a few things from my investment portfolio to pay it off. But the thing is, investments are investments. They earn money. And the cost of this mortgage— the financial cost— is small. I have a rate below 2.5%! It's financially a loss to sell assets that return way better than 2.5% APY to pay off a loan that costs less than 2.5% APR.

What would change that calculation? One thing is if the emotional cost of keeping the loan with these clowns becomes too expensive. The first time these clowns screw up in a way that's more than just passively irritating, I may just pay them off and be done with them.

I saw a news article today about moral panic over BNPL. Apparently discussions have exploded on social media recently about people buying tickets for SXSW— the annual South by Southwest music/film/pop tech festival in Austin— using Buy Now, Pay Later (BNPL) services. The tenor of the discussions, which are really more like opposing rants, seems to be  Kids These Days are being fooled into spending money they don't have on things they don't need vs. Old Fogeys who can't open their email without downloading at least 3 viruses. That prompted me to think, What is BNPL— and is it good or bad?

I've been vaguely aware of Buy Now, Pay Later schemes as a way of buying things online for a while now. I say vaguely because I know they're out there but I've never looked into them. And yes, lurking within my terminology is a value judgment. I've thought of them as them schemes because I've been suspicious from the start that they're come-ons that snooker uneducated customers into overpaying, in the form of high interest rates and service charges, on luxuries they maybe shouldn't be buying in the first place. But it's not just stuff like travel and pricey concert tickets; nowadays even DoorDash offers BNPL. If you can't afford a Chipotle burrito without financing it, maybe you shouldn't be eating out so much!

Okay, so what is BNPL? It's micro-credit. When you go to purchase something online, instead of charging it to a credit card, you can charge it on a BNPL plan. There are lots of fintech (financial technology) companies out there— many startups, but also bigger companies now— that offer these short-term loans and are integrated into various e-commerce sites. You go to checkout, you see the BNPL offers, and maybe you pick one of those instead of entering a credit card number. BNPL sets up a small loan specific to the thing you're buying. The merchant gets paid right away, your item ships right away, and you pay for it in installments.

See? Put that way, BNPL is not so foreign. It's kind of like a credit card. But it doesn't require opening a credit card in advance. This makes it accessible to the "under-banked": the socioeconomic group of people who find it hard to use banks or who are under-served or rejected by banks. The modern technology and interface for setting up BNPL works in a way that's way more familiar to younger generations. That helps explain the definite age gap in whether your reaction is "Wow, BNPL is great!" vs. "What's this new-fangled thing that's trying to steal my money?"

Okay, but is it stealing anyone's money? Part of my initial suspicion about BNPL was that it seemed to good to be true. Companies have to make their money somehow. How does BNPL earn money? In particular, are they like another credit provider for the under-banked— payday lenders, who charge outrageous interest rates and fees?

A bit of research shows that BNPL generally does not charge high interest rates. In fact it seems that a lot of offers extend short-term credit to buyers for free. For example, a customer purchasing a $1,000 plane ticket may be offered a plan to pay $250 now with another $250 due each of the next 3 months.

BNPL makes its money, as credit card companies do, by charging the merchants a fee. And, also like credit card companies, they make money by charging fees to the borrower if they miss any of their payments. If you're a few days late with one of those $250 installments, you may find all your remaining installments going up to $260— plus a $7 late fee.

A lot of the moral panic around BNPL is that it encourages people to overspend. I'll just point out, that's been a concern with credit cards for decades, too. I remember when I was a kid watching a family TV show in reruns, a well known older show that was in Black-and-White, where in one episode the teenage characters were getting themselves in all kinds of trouble because one of them had a new credit card and could not understand that he still had to pay for things, eventually. "Really, the moral of this TV show is 'People Are Too Stupid To Understand Credit Cards?'" I thought to myself. And I was a pre-teen then! The point is, what was a moral panic of 1960 seemed foolish by the 1980s. Similarly, much of today's hand-wringing about BNPL seems like people choosing to be frightened by a new technology they're unable or unwilling to understand.

But that said, it does seem wrong that you can finance a burrito on DoorDash.