Day 2 of Training: A Better Pace

Chicago Trip Log #5
Downtown Chicago - Wed, 13 Aug 2025, 10:30pm

Day 2 of training has gone better than Day 1, particularly in terms of not zoning out in one of the late-afternoon sessions. Partly that's because I got almost 2x as much sleep last night as the night before; partly it's because today's session mercifully ended around 3:15 instead of going up til 5— or even 5:45pm.

After the early end today I headed up to my room to unwind and do personal stuff for two hours. Just that bit of relaxing "me" time really helped. At 5:30pm I headed back downstairs to meet my colleagues for a team dinner. We walked out to a restaurant a few blocks away.

The weather in Chicago is stupendous today. Early in the week it was hot and sticky, with highs in the upper 80s. Since then it's gotten cooler. Today the highs topped out at 79°. And after some clouds at midday the sky was clear all afternoon. We enjoyed our walk to the restaurant, taking a scenic detour through Millennium Park to pose for a group selfie at The Bean.

Dinner was a 3 hour affair, including the time to walk there and back. Sales team dinners are always way slower than dinners out Hawk and I enjoy ourselves. For one, team dinners usually involve a nicer restaurant— or at least a more expensive restaurant— where people are expected to stay longer. Two, the pace of dinner is slower because everyone is talking. And three, the pace of dinner is slower because we end up ordering drinks, then salads and appetizers, then mains, then desserts. When Hawk and I dine out by ourselves we usually just order mains and call it done. Sometimes we add dessert as an indulgence.

After dinner the team stopped at the hotel bar for a nightcap. This time I joined them, unlike last night. And this time a nightcap was just a nightcap. My boss was paying and he's not generous. I mean, he's expensing it to the company so it's not his money, but still he's not generous. He closed the bill after one round of drinks. But that was okay with me because I didn't want to stay up late again. And anyway the server accidentally brought me two drinks. 😂🥃🥃

I got back to my room just after 10 this evening. Now I'm winding down and hope to be in bed, lights out, before 12. Yeah, that's not early.... At home I'm often lights-out by 10:30. But it's not that late by the norms of a team business trip. Certainly it'd still be earlier than the 1:30am I got to bed Monday night!

Update: Haha, nope. I stayed up until almost 1am. 🤦 I just couldn't get to sleep.

Training Day 3: It's a Wrap!

Chicago Trip Log #6
Downtown Chicago - Thu, 13 Aug 2025, 4pm

This installment of sales training is a wrap! We finished Day 3 a bit early, around 3:30pm. It was both an easy day and a hard day. ...Easy, because there were only 8 of us involved in for Day 3 (versus 40-ish for Days 1-2) and our manager kept it casual. But also hard because we made the whole day about interactive group activities. There was no time to tune out by reading news on a smart phone or blanking out during a dull session.

And we pushed each other hard during our collaborative activities. Yesterday I'd introduced people to the warrior saying, used by famous generals from ancient Greece to the likes of Norman Schwarzkopf, "We sweat in training so we don't bleed in battle." Well, today my boss giddily repeated that phrase when my colleagues balked at how hard he was pushing them.

Most of the 8 of us are now downstairs at the hotel's bar enjoying one for the road. I'll leave momentarily for the airport. Even though my flight's not 'til almost 8pm I'd frankly rather not hang around a hotel bar— especially one where beers on tap are $15! I'd rather find a quiet spot at the airport and cool my heels there. Then, it doesn't matter if something goes crazy wrong with traffic. I'll be less than 5 minutes from my gate.

Comedy of Errors Leaving Chicago

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.