Good morning friends, it’s Monday, August 11, 2025. The weather is: 85 degrees outside and sunny, and I am relaxing at my favorite coffee shop near my house in Fort Worth, Texas.

A year ago today, I was visiting my Aunt and Uncle in Hudson Wisconsin with my mom. I didn’t know it when we planned the trip, but my Uncle owns a Indian Scout motorcycle, and was happy to let me ride it. That turned an already fun week into an epic fun week.

On top of that, Wisconsin was having a cold spell, so the temperatures were averaging around 70 degrees, which is waayyyy cooler than then 105 degrees we have in North Texas during August.

The only downside was that Chartable (where I was working as an account manager at the time) had an epic fail after an update was pushed by the engineering team, and our customer’s dashboards and data were unavailable for pretty much the entire week. This is a worst case scenario for a software-as-a-service company, and our customers were understandably pissed off. Unfortunately there was nothing I could do about it but keep an eye on our internal Slack channels and wait for updates from the engineers.

So while I was having the time of my life riding a motorcycle around Wisconsin, our engineers at the company were having one of their worst weeks ever. A strange coincidence, but that’s how it goes sometimes.

Turns out my Uncle Scott and I wear almost exactly the same clothing sizes, so I borrowed his jacket and chaps for the ride from Hudson to Prairie Du Chien and back.

Here’s the journal entry from the end of the week:

So great to see Scott and Cheri, Mark and Tami, and a bunch of my Mom’s family in Prairie du Chien. Visited the dike and downtown in Hudson. Getting ice cream and pizza. Riding Scott’s motorcycle around Hudson and down the Mississippi River. Stopped in Red Wing MN to buy new Red Wing Chelsea boots. Stopped in Winona to get lunch with Brett Terpstra. Stayed at Mark and Tammy’s house. Getting dinner / breakfast at huckleberry’s. Watching the Brewers win while drinking Spotted Cow at the Sawmill Saloon. Walking home along Michigan street. Getting coffee and working at Simply coffee shop. Erik put on a great show at the concert in the park and then again after at the Tavern. Getting burgers and a T-shirt from Pete’s. Fish and chips at Blackhawk. Driving the motorcycle back to Hudson along Wisconsin’s west coast Mississippi River road. Shooting clay pigeons with Scott. Took mom for a motorcycle ride to give it a good clean and polish at the car wash. Playing pickleball and table tennis with Scott and Cheri.

Good memories. I’m hoping I’ll have time to go back soon. Trading the summer heat in Texas for the cool weather up north is definitely one of my all time favorite life hacks.

Thanks for reading,

Aaron

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