Tales & Trails of a Traveling Wiseguy

Texas Trip log #3
Residence Inn · Wed, 12 Nov 2025. 12:05am.

My Southwest Airlines flight to Austin not only left on time this evening, it arrived early. "Well, we got you to Texas 15 minutes early," the purser quipped over the speakers. "When we're late next time we'll call it even." See, even Southwest employees know their airline has a reputation for arriving late. 🤣

It's not as simple as, "We arrived early, woohoo!" though. The system is not set up to handle flights arriving early. As is frequently the case with an early arrival, our flight had to sit on the tarmac waiting for our gate to open up. You see, in the name of efficiency the airline figures out how to use the fewest gates possible, which generally means a gate doesn't open up until 2 minutes before your flight is supposed to land. So all of our 15 minutes of earliness was consumed just sitting there, 300 feet short of the gate.

Since I'd canceled my car reservation when my travel plans changed at 41,000' I thought I'd save a bit of time getting to the hotel by hopping in an Uber instead of walking all the way to the car rental depot. Oops, no, the designated spot for ride-share pickups is in the same far parking structure as the rental cars.

Well, one advantage of taking an Uber remained not having to drive. It was going on midnight local time as we whisked across uncrowded highways around Austin. Though it was only 10:45pm for me, on California time, it was still late by my usual schedule. I thought I might nap a bit on the flight. Strangely, I didn't. I was wide awake the whole dang time. And now I was struggling not to nod off.

The Residence Inn was quiet when I arrived. Despite rates being high when I booked the hotel seem to have low occupancy. I checked in, got my keys, and went upstairs to my room. To my chagrin I found that I was in an "armpit" room— wedged on an inside corner of the building, where there was no window near the bed and only a small window near the desk that looked straight into a hallway window 5' away. It's like they assigned me the worst room in the hotel. So much for Lifetime Titanium status. Not only don't I get an upgrade, even a trivial one, I pretty much get a downgrade. And I'm paying $200++ a night for this!

I called down to the front desk to complain about the room with its missing window. "Do you have anything better you can put me in?" The desk agent tap-tapped on his computer and asked me to meet him at the elevator for new keys. "It's a one-bedroom suite," he informed me. Well, it's the same size as the other room, just there's a wall in the middle. 🙄 But at least it has 2 windows... which it turns out will be really important tomorrow when I'm trying to get work done, because the lighting in here sucks!

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.

I saw a news article last week about Lyft CEO David Risher discussing enshittification in the ride-hailing platform. Recall that "enshittification", a term attributed to author Cory Doctorow, is the process of services getting worse for both consumers and sellers/advertisers/workers to enhance investor returns. Does Risher cop to Lyf being enshittified in his April 24 letter to shareholders? Eh, not quite.

Risher's letter (posted publicly at the link above) follows a familiar, three-step formula for leadership communication:

1. Things are going great! Fantastic! Look at these impressive charts!


2. But amid all this success, there's a pitfall we need to worry about.


3. But we can avoid that by all pulling together and working hard, with the benefit of this great new discipline I've thought of.

Enshittification is the pitfall Risher describes in part 2. But really the letter isn't about enshittification; that's just a motivation to help explain his brilliant new strategy in part 3, which he dubs "Falcon Mode".

That said, enshittification is a real pitfall at Lyft. I've seen the service enshittifying over the past few years and have groused about it many times in my blogs. My complaints:

• Lyft rides have been getting more expensive and are frequently much more expensive than its direct competitor, Uber


• Lyft rides often cost more than the price displayed when I choose the ride, due to hidden, extra fees tacked on.


• The process of getting matched to a driver is taking longer and longer. Multiple times I've selected a ride in Lyft, waited several minutes, then canceled it and pursue another option— including asking my spouse to drive me to Oakland!

Risher only barely touches on any of these three problems. The closest he comes is writing about needing to improve the number of drivers by making the platform more friendly for them. More drivers might improve the first and third problems, indirectly. But Lyft drivers I talk to don't tell me the problem is the platform is "unfriendly" or "hard to use". It's that they make less money with Lyft than Uber. That is the key sign of enshittification— customers see worse service and higher prices, while suppliers fume about getting less and less.

NYC Quickie Travelog #2
DEN Airport - Sun, 23 Mar 2025, 2pm

It's been a long road to New York City today, a longer road than it had to be... but maybe easier?

Traveling nowadays is always a series of tradeoffs. The most direct flight coast-to-coast? Stupid expensive. Or only middle seats in steerage left. Or both. The next most direct flight? Nonstop to EWR. Which is fine if you're staying in New Jersey, but to upper midtown Manhattan it's 4 trains on 4 different systems. Or 3 trains plus walking 2km. Or $100++ for Uber/Lyft. So I chose to fly Southwest to LGA. Which means taking a connection. On the plus side, my Southwest elite status and Southwest's open seating policy— soon to be RIP— guarantees I can get a decent seat. And a midday connection in Denver means I can eat lunch at a real table and choose something tastier than an airline snak-pak. See? Tradeoffs.

Then there's the tradeoff of departure and arrival times. Flying west to east already makes scheduling hard, given the 3 hour timezone change. When flying with a connection the choices are often leave stupid early, arrive stupid late, or both. I found one itinerary that wasn't ridiculous on either end— depart 9:20am, arrive 8:05pm— but it meant hauling up to OAK airport, 40 miles from home.

Then there's ride-hailing services. Those have become a tradeoff all unto themselves. You want sneaky fees and shell games finding a driver? More and more, those are standard. When I hailed a ride at 7am this morning the app spun for a few minutes then assigned me a driver 12 minutes away. Then that ride disappeared. "We're looking for a new driver," the app told me. Then, "We're still looking for a new driver." My estimated pickup time telescoped to 20 minutes past when I first pressed the "Buy" button.

Fuck that, I decided and woke Hawk up to drive me to OAK. Fortunately for her this didn't come out of the blue. We discussed last night the possibility of me needing her to give me a ride at 7:15am. Yes, that's how enshittified Uber and Lyft have become; that I now routinely make a Plan B for "What to do if Uber and Lyft are useless."

Well, I got to OAK in good time, no thanks to anyone but my gracious spouse. And the flight left on time, so here I am in DEN, as planned, with time to eat lunch at a real time and without my elbows pressed in against my sides. OTOH it's still hours to NYC, and I'm not going to get to my hotel until at least 9pm local time— and even that only if things continue to go (mostly) right. Tradeoffs.

Update: MOAR tradeoffs in traveling to NYC!

Panama Travelog #35
Metropolitan Park, Panama - Mon, 30 Dec 2024. 12pm.

"It figures," I scowled as I arose to brilliant sunshine pounding through our hotel room's floor-to-ceiling windows this morning. "The first sunny day in Panama City is our last full day in Panama!"

What a fitting thing to say on this star-crossed trip. A bit of good news is hard to appreciate because it reminds us of all the frustrations we've had to deal with.

But hard to appreciate doesn't mean impossible. And with a list of possible activities Hawk drafted in advanced we looked for the most outdoorsy one still in the area. It would be Panama City's Metropolitan Park, right in town and with a small network of trails including a stellar view of the city itself.

We Ubered over to the park's visitor center. The fare was $3.19 for a trip of just under 4km. Uber is ridiculously cheap here by US standards. I left a baller, 30%+ tip— a whole dollar. 🤣



From the park visitor center we walked 0.7km up a trail that mostly paralleled a road through the park then 1.1km up to the top of Cerro Cedro. It's the 2nd highest hill in the city, at 160m (524') above sea level. Outlooks at the top of the hill provide commanding vistas in multiple directions, including the one in this photo showing the main downtown area of Panama City.

Edit: Which building is our hotel? We're about 90% of the way over to the right in the photo above, just to the left of the tall, black building (Tower Bank) anchoring the right edge of the picture.

As we looped back down a different trail from the summit we saw some wildlife. I'll share short videos of those in another journal entry.

Update: see my journal with video of 3 animals we saw in the park.

Trade Show Travelog #8
LAS Airport - Thu, 5 Dec 2024, 6:15pm

Another year of AWS re:Invent is a wrap. The exhibitor show closed at 4pm today. I'm now at the airport awaiting my 7:15pm flight home.

I worked the full day at the show today, 10am-4. I was only on the duty roster to work 'til 1pm. In the morning I checked with Southwest Airlines to see if I could change to an earlier flight. The option was there to confirm a seat on the 4:20pm departure... but I decided, "Enh, I'll see how things are going at the show at 1pm and check again later." That was a mistake. By 1pm all the confirmable seats were gone.

But staying through 4pm was also a good thing, for the team. The booth got busy in the afternoon, even after other people peeled off to travel home. The last 8 of us were often all tied up working. And people responded well to Jenkins the Butler being in the booth.



Yes, I dressed as The Butler again today. I drew a lot of traffic into the booth just by people recognizing me— or, should I say, my persona. They'd walk by, do a double point, then point and laugh (in a good way!). I'd wave them into the booth. Lots of people took selfies with me.

I also had a good conversation with an overseas partner while dressed as Jenkins. This was an executive meeting with one of our VPs... and the partner VP recognized me from Jenkins World conferences as far back as 2018! We also compared experiences from 2022 getting out of Orland, FL when Jenkins World was canceled last-minute due to an oncoming hurricane.

The end of the show at 4pm might have felt like the end of the workday. But, ugh, it was not. First, I stayed to help the team tear things down and box them up until about 4:30. Then it was a loooong walk back to my hotel's bell desk where I'd left my suitcase. Then it was a long wait, 15-20 minutes, for a car via Uber and Lyft. Oh, and prices were high. Uber wanted over $80. Lyft was under $50... until I clicked for the ride then it was suddenly $65. This isn't the first Lyft has been thieves. But still they were cheaper. 🤷 Oh, and traffic made things take a long time to get to the airport. The ride was almost 25 minutes. It's less than 5 miles.

At the airport my first order of business— after getting through security, that is— was to get dinner. Dinner at 5:30pm was the first food I've had since before 8am today. Yes, I was so busy at the show I skipped lunch today. But now I've eaten, and I'm sitting, and I'm finally unwinding. So far my flight home to SJC is showing on time. Fingers crossed Southwest doesn't find a way to disappoint as usual.

Thanksgiving '24 Travelog #1
OAK airport - Sat, 23 Nov 2024, 6:20am

Hawk and I were up early this morning, like alarms set at 4:30am early, to begin our Thanksgiving trip. It was still pitch dark out when I checked Uber and Lyft at 5:10am to roll to OAK airport. The fares were ± $100. I chose Lyft and... waited. It was still pitch dark out at 5:15am when I gave up waiting on their shenanigans with how long it would take for a driver to arrive, even after trying the more expensive "priority pickup". It was still pitch dark out at 5:17am when we decided "Fuck it, we'll drive our car to the airport and pay for parking," as I backed our car out of the garage. The enshittification of everything.

It's mostly pitch dark out now at 6:20am as I write this, sitting comfortably in the airport gate area. The first light of day has just appeared over the trees. Actual sunrise isn't for another 38 minutes.

Oh, and the decision to park at the airport was not quite the over-under I thought it would be. When Uber/Lyft cars were running ±$100 each way I figured that parking, 9 days at $20, would be cheaper. Nope, parking is now $26/day. So driving is not cheaper, even at eye-watering ride costs. Well, at least we have certainty about our schedule. And don't have to wait for pickup-time shenanigans when we arriving home 9 days from now, late at night and tired.

Our flight departs at 7:30am. Tracking shows the inbound aircraft operating on schedule. So chances seems good we'll depart on time. The airline is even estimating we'll arrive on the east coast 20-25 minutes early. This is Southwest Airlines, though. I'm all but certain they'll find a way to leave 10 minutes late and waste that 20-25 minute buffer somewhere.

This morning I got an email that struck me as strange right off the bat. Lyft was advertising to me that I should use their service for my commute. "WTF?" was my immediate thought. "Hiring a ride to/from work every day would be expensive!" ...Not that I actually have a commute right now. I've been 100% remote the past 5-6 years and partly remote another 5 years before that. But I've also had plenty of in-office jobs, and I've both driven and used transit for commuting, so I have a strong sense of how (un)realistic this is.

People who read my blog regularly should know that when it comes to a proposition like "Does it make sense to use ride share services for commuting!" I don't just say Yes or No and move on. If I think it's a plausible idea I'll do a back-of-the-envelope calculation to be sure. And even if I think the idea is absolutely nuts I'll still work out the math just to demonstrate how cracked it is. 😅 So here's some math— and some thinking about the situations where ride-sharing for a commute might make sense.

My company's office, the one I was officially de-assigned from back in, like, 2018 in a cost-cutting move— is 10 miles away. A quick check on ride-share apps shows the fare to get there right now is about $24. Let's call that $27 with a tip. But that's mid-day. I could imagine commute hours trips easily running $30-35 with traffic and demand pricing. That's $60-70/day.

Spending $60-70 per day on a commute is a lot. If you do that every day, let's say 20 working days (average) per month, that's around $1,300 per month or $15-16k per year.

This reminds me of the calculations I did when I was starting my first professional job. I worked out that the costs of taking transit (which really wasn't designed for the commute I had) were higher than the costs of owning a car. And yes, I considered not just the monthly cost of a car loan but also insurance, maintenance, and gas. My calculations showed that the transit costs I avoided paid for all my car costs— meaning I had the car for leisure use nights and weekends basically for just the cost of extra gas I needed to buy.

Indeed, "It's cheaper just to drive" has been the answer for most commutes I've had since then. And those have ranged anywhere from just over a mile each way to nearly 40 miles each way. The one thing that has swung the needle in favor of transit versus driving was when there was no free parking at the office. That would change up the calculation of driving vs. ride-sharing, too. For example, one of my customers says that parking near his downtown SF office is $20 even in the company-sponsored garage. Though rather than motivate him to use transit or ride-sharing it actually just motivates him to limit his in-office workdays to one a month.

Another thing that could swing the needle in favor of ride-sharing is if you don't go to the office every day. Suppose you need to be in-office 2 days a week. Then the example commute I described above averages $130/week, $520/month, and $6,200/year. That starts to compare favorably with the costs of owning a car.... Though if you don't own a car you've probably got to add on a lot of ride-share trips for other things such as grocery shopping, visiting friends, and occasional dining out. I don't see many ways ride-sharing to work makes sense for people living in areas that make driving a practical necessity.

I'm back home from my brief trip to Southern California. It was a bit longer than initially planned, both because of extending it a smidge to accommodate a second customer meeting and because of a delayed flight. I got home just after 8:30 tonight, making it a round trip of not quite 30 hours. Still, I'm glad to be home.

One thing I checked as I got home was the relative value of using Uber/Lyft to and from the airport instead of driving. On a same-day trip several weeks ago I drove to the airport and used hourly parking. For one day it was $30, much cheaper than an Uber/Lyft round trip. For this trip I figured I'd be parked over 24 hours, doubling the cost to $60, so I went with Uber/Lyft. Well, the round trip was nearly $60. It was a tie, cost-wise. And I had an annoying wait for a driver on the outbound leg. Fortunately I got a driver quickly on the homeward ride tonight. But what this shows me is that for two-day trips it's worth it to pay $60 for parking. I mean, that seems obscene, paying $60 to park for just a smidge over 24 hours, but the price comparison checks out.

In my old days of travel, the 90s and 00s, I'd drive to the airport and park. Parking was expensive, but taxis were even more expensive. Even when leaving for a week I could often find a coupon that made parking for a whole week cheaper than two taxi rides. Plus, taxis were unpredictable. After calling for a pickup at my house I might wait 30 minutes for a driver to show. Though parking at the airport entailed its own form of waiting... like waiting up to 20 minutes for a shuttle from remote parking to the airport, then the agonizingly slow and/or long ride in the shuttle.

Uber and its imitators like Lyft changed that up in the early 2010s. Suddenly instead of using 50 year old technology to dispatch 20 year old cars, I could hail a ride in a near-new car using my smartphone. And it was half the price of a taxi. And I could pay with a credit card without arguing. Driving to the airport and parking became a rarity.

Over time Lyft and Uber have become more expensive. A ride between my house and SJC now runs around $30 normally with surge pricing of $50+ at peak times and late evenings. SFO is $50-60 normally, $80+ on surges. And that's before tip. Ten years ago tipping was not a thing with Uber and Lyft. They added that in, and we users accepted it, because they were screwing their drivers and we felt sympathetic. Bottom line, Uber/Lyft prices have increased to the point that driving and parking is attractive again, on shorter trips.

I did a quick cost comparison ahead of my day trip to Phoenix yesterday. I realized I could park in the hourly lot for probably half the price of two Lyft/Uber rides. Unlike the long-term lot or an offsite lot, which requires those infuriating shuttle rides, the hourly lot is seriously convenient to the terminal.



The photo above shows where I parked (black SUV on the right) relative to the terminal (straight ahead). It was just a few minutes' walk to the terminal door. That totally beats the old rigamarole of the long-term lot with waiting up to 20 minutes each way for a shuttle bus and then shuttling miles at low speed.

Edited to add: Driving and parking also gave me certainty about my schedule. There were no doubts about how long it would take a ride share to arrive of if the driver would cancel. One of my colleagues scheduled an Uber for 5:30am the night before— and the driver simply didn't show. 😨 He had to hail another ride after giving up, then that driver canceled and another was assigned. The net result was he got to the airport 30 minutes later than expected and arrived at the boarding gate only 2 minutes before boarding began. What bullshit! I am so glad I wasn't playing that game.

On the way home last night I was pleased all over again with how convenient and cost-effective the arrangement was. During the flight I made arrangements via text to meet Hawk for dinner— but the dinner date needed to be timely because it was already getting late. The plane docked at the gate at 7:20pm, I was in the terminal by 7:25, minutes later I was riding the escalator down past baggage claim, and....



BAM! I could literally see my car from the escalator down into the arrivals hall. No waiting 20 minutes for a shuttle bus that drives slowly to a remote parking lot. No waiting 10 minutes for a Lyft that says "4 minutes away" for 6 minutes. For amusement I timed my walk from the terminal door to my car door. 1 minute 52 seconds. 💥

Less than 15 minutes later I met Hawk at a favorite local pizzeria, Giovanni's. I arrived just as she was getting out of the car. A delicious meal together was a great way to wind down a day that had already been 15 hours of go-go-go.