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