Tales & Trails of a Traveling Wiseguy

Today was my official last day of work / start of retirement. Yeah, it seems like I've been retired for almost two weeks now. That's because after I submitted my notice of resignation exactly two weeks ago, my company walked me the following Monday.

I've been doing a whole lot of... nothing much... to soft-launch my retirement. Yes, I had/have great plans for what to do in retirement, but I'm caught in a slow period right now. Hawk has been working through medical issues that have made her unable to travel and do outdoors adventures. Recently I decided that since she's on the DL (disabled list) I might as well go on the DL, too. Thus my choice to see a dermatologist about removing a lump on the back of my head. No cardio exercise or even going to a pool for me for a few weeks.

One thing I've reflected on at this two-week anniversary is this meme I've shared a few times when discussing retirement:



I'm happy to report that I am no longer feeling like the sad person in this illustration. I'm not yet the happy person recording cell phone video of sunny long-range vistas— though I know that will come eventually. Once we get off the DL together.

What's changed? I figured before a combination of two things were making me feel down. One was unsorted feelings about quitting my job, for good. The other was misgivings about "What if the money in retirement doesn't last?"

Well, the latter's already getting a bit of a test with how markets have been slumping the past two weeks. And it's not bothering me. I built our financial plan to handle bumps like this. Nearly every day I revisit the numbers to remind myself it's working.

That leaves unsettled feelings about quitting as the culprit for my feelings of sadness and anxiety. Two weeks later isn't a hugely different vantage point to revisit this question, but in terms of how I'm feeling about it, it's close to night and day different already. I have no question about whether I was right to leave that job. I am so over it now. Zero regrets.

I've been working on my taxes... for 2026. As in, the taxes that aren't due until April 2027. Why not work on my 2025 taxes? It's because my banks haven't sent me the forms yet! So for lack of anything better to do I'm getting a head start on next year. 😅

I'm still doing my own taxes, though for the last 12 or 13 years I've used TurboTax to help automate things. Is TT helpful? Yes. Is TT frustrating? Also yes.



Using TurboTax is like having an abusive partner.

Thankfully I'm not to the point yet this year of actually using TurboTax. That'll start next weekend when I dig in on my 2025 taxes.

So far in working on my 2026 taxes what I'm really doing is building & refining estimates on my own spreadsheets and then using those estimates to guide investment decisions. Among other things I've green-lit taking profits on a few investments I want to trim, then hit the pause button on profit-taking, and adjusted my 401(k) contributions twice. It's better to do these things with a plan and with data to support the plan, versus doing them blind and being surprised by an unexpected tax bill a year from now.

After our car went kaput on Sunday (dire warning messages on-screen, fluid pouring out of the engine) we had it towed to a trusted mechanic on Monday. Long story short, we picked it up yesterday with a $4,000 repair bill. The problem was a cracked oil filter housing. The car has just over 60k miles.

This breakage wasn't a result of an accident or even hard use. We don't take the car to track days. We don't even drive particularly hard. This failure was simply the result of weak design. A $4,000 repair— at barely over 60k miles!

"Is this normal?" I asked the service writers at the shop. Hawk had asked too, over the phone. Together we asked 3 different service writers. All of them said, "Basically, yes." This part of the engine is known to fail at 60k-80k miles.

"How many other expensive repairs like this are we going to need to make before this car is even considered 'high mileage'?" I asked.

The advisors shrugged.

With a bit of affably prying I elicited from them, "Buy a Toyota." These are BMW specialists. And they all own Toyotas. 😰

Look, I understand that repairing a BMW isn't cheap. When I bought my first BMW, a used M3 twenty years ago, I knew that though I was buying the car for less than 20 grand, the price of a base Toyota Camry new, the maintenance bills would still be those of a 50 grand performance car. "You're going to have $700 oil changes!" people warned me— and I accepted that. (Actually, though, $700 wasn't an "oil change", it was Inspection II service, which included replacing spark plugs and inspecting numerous things in addition to simply changing the oil.)

Even though our current BMW, a 230i convertible that we love, isn't as highly tuned as an M3, I get that repairs are always going to be more expensive than a Toyota Camry. But having a failure of a major engine component— because it was built of plastic— at merely 60k miles is beyond the pale. What's going to break at 70k? At 80k? Is this car going at the point in its life where it's going to have $4-5k maintenance costs yearly?

"It's at the point where it starts getting expensive," one of the service advisors admonished us.

Fuck that, it's just 60,000 miles! 60k is not "high mileage"! Our previous BMW started getting expensive, too— but at 120k miles.

Is this the new normal for BMWs? They're not just expensive but start falling apart at 60k? This is not what I signed up for.

I had a pretty quiet weekend again this past weekend. Boring, too. How boring? So boring that I started my taxes. ...And I don't mean my taxes that are due April 15. I started next year's taxes. The ones for 2026 that aren't due for another 15 months!

Why start so soon?

As I've mentioned before, I start my taxes a year in advance. Obviously I can't fill out forms yet. I mean, I won't have the numbers for at least another 12 months... and even the forms won't be available until around this time next year! But what I do start a year in advance are estimates.

I like to know in advance approximately what I'm going to owe for taxes. With that knowledge I can adjust my withholding rates, if necessary, and also pay quarterly estimated taxes accurately. My goal is not to be surprised by a big balance due or refund come April— whether that's April 2026 or April 2027. A big balance due can mean penalties owed to the IRS... and a big refund means I've lent them money at 0% interest! Either way, ugh.

Working on these estimates now for the tax return I'll file 15 months from now already has proven worthwhile. As I plan to retire soon this year I'll be shifting from earning significant amounts of money in wages to getting most of my taxable income from dividends and capital gains. That has tax implications. Dividends and capital gains are taxed lower than wages. There's an interesting edge case where some dividends and cap gains can be taxed at 0%. That provision never applied to me before because my wages were always too high. I worked through that edge case in my planning this weekend. It lowered the tax I expect I'll owe by several thousand dollars. Hooray! And by knowing that now I know not to overpay on quarterly estimated taxes and give Uncle Sam a big, interest-free loan. That makes my advanced preparation a double win.

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.