Late Night, Early Morning in Chicago

Chicago Trip Log #3
Downtown Chicago - Tue, 12 Aug 2025, 6:30am

Don't hit it too hard the first night. That's one of my rules of sales trips. There's a temptation when in a new location, meeting colleagues I maybe haven't seen in a while, not being tired from a full day of meetings (yet), and  wanting to live it up after the many little ignominies of flying coach, that all contribute to eating and drinking too much and staying up too late the first night of a trip. I went into last night with good intentions... and feel like I mostly failed.

At first I thought I would enjoy a casual dinner and retire early to my picturesque corner room overlooking the park. I waited downstairs for a while to see if any colleagues might happen by who'd like to join me. One did... and she dragged me off to a steak house where a colleague of our had made a reservation. Good news: it's Bavette's Bar & Boeuf, a well regarded steak restaurant in Chicago. And the 5 of us there had a great time. And I enjoyed a few drinks without getting drunk. Bad news: I didn't get back until 11pm. And I'd eaten so richly that between that and the time zone change, I couldn't fall asleep until almost 1:30am. Even worse news: at 5:30am my body shouted, "Adrenaline, motherfucker!" for no goddamn reason and woke me up well before even my 6:15am alarm.

So, here I am.  I haven't even started the first day of 3 days of sales training, and already I feel like it's going to be a long slog. 😖

Update: Oh, at the restaurant I mentioned to one or two of my colleagues how happy I was with my nice room. They got corner rooms, too! Of course, they also made Club this past year— like I did. So maybe the upgraded rooms were doled out to us top performers, similar to when they sent a chauffeur in a $600,000 car to pick us up from the airport a few years ago.

Long Day 1 of Training; Quiet Evening

Chicago Trip Log #4
Downtown Chicago - Wed, 13 Aug 2025, 7am

Just like I figured was going to happen after I stayed up too late carousing with colleagues on my first night in Chicago, Day 1 of training on Tuesday was a long slog. It started at 7:15am with breakfast in the meeting rooms, the training proper running from 8 to 5, and then a small team meeting until 5:45pm. 10.5 hours of being "on"— after me getting only about 4 hours of sleep. Ouch.

I kept a game face on for most of the day. Late in the afternoon, though, I kind of lost it. Around 4pm the person who was speaking was not that engaging, and I nodded off a few times. I don't know if I actually fell asleep for a moment at a time, but I definitely did blank out a few times. I got lost in my own thoughts and suddenly realized that I'd stopped seeing or hearing what the speaker was talking about. Fortunately the next speaker was stronger. And the small team meeting at the end of the day was no problem since that was just 3 of us so I was actively engaged. It's much easier to stay focused when the content of the meeting is actively engaging rather than when I'm passively consuming it.

Those 4pm nap attacks, though, told me that I needed to take it easy last night instead of staying up late carousing with colleagues again. Thus I sent my regrets to our regional sales leader that I wouldn't be able to attend his dinner. I figured I'd instead eat on my own and get back early.

As I was considering where to get dinner solo I saw on Slack that one of my colleagues hadn't been invited to any group dinners and was looking for company. I invited him to join me. We agreed on a Chicago pizza chain (Giordanos, for those keeping score) with a restaurant location a few blocks away and walked over there. We split a pizza and an appetizer and enjoyed a couple beers each while chatting amiably about mostly not-work things. It was a right-sized dinner, both in terms of food, drink, and energy levels.

On the walk back from dinner I spotted a few of my colleagues in the hotel bar. I resisted the mild temptation to join them. I knew that "Hey, come have a drink with us!" would easily turn into 2-3 drinks and likely another evening of staying up too late. Instead I retired to my room for a quiet evening. I was in bed not long after 11pm.

This morning I'm feeling a lot more ready for a full day of training than I was yesterday morning. The difference is today I've got 7.5 hours of sleep behind me rather than just 4. That means tonight I should in good shape for the next group dinner / late evening of carousing with colleagues.
Update: over dinner last night I mentioned to my colleague that I'd been upgraded to a nice corner room with a wrap-around balcony at the hotel. "I'm in one of those, too," he said.