Back story on these posts
I am writing this post in January 2026 to give background on a set of 25 year-old emails that I rescued from my old Cloudyhands website to publish here.
Here’s how I happened to be making this trip:
I left Autodesk at the end of 1999, and suddenly I had a lot of time on my hands!
- Harvard Class of ’70 was keeping me WELL informed that my 30th Reunion was coming up!
- Long road trips are kind of a family tradition.
Me and my mom did them most summers growing up in Louisville. - I was newly single so I could just pick up and go on my own … and a change of scenery for a few weeks would be pretty nice!
- One of the changes for the new “single guy” me was to trade in the common-sense Peogeot sedan we had as a couple and to get a rough and ready a Tacoma with 4WD with a camper shell!
So LET’s GO!!!!
From my time in the corporate world at Autodesk, I was still a Windows guy.
Every night I would cart my trusty Windows laptop into the motel room or friends guest room where I was staying and hope the wifi was good enough to send out the group email reporting on my day!
I still used Outlook for my mail. This was way before gmail was a thing.
I visited my share of small town libraries when the motel wifi didn’t cut it. Looking back, those library visits were a treasured part of the trip!
The stories were “published” as emails to a distribution list of friends.
Back story on why this trip!
I graduated from Harvard College way back in 1970.
So when the year 2000 rolled around, simple math tells us that my 30th college reunion should be happening back in Cambridge MA.
I had attended a couple of earlier reunions: my 10th and my 15th.
At the time of those earlier events I was living in the Washington DC area, so it was a simple matter of packing the car and heading up the Eastern seaboard for the weekend.
In 2000 I was living in far-away northern CA, so this one was going to require a lot more planning.
The Universe came together to make this happen
- I left Autodesk in 1999.
- My divorce was finalized so I was thoroughly single.
- I started working at a start-up in the City called LagunaStreet.
- LagunaStreet was fun while it lasted, but it didn’t last very long.
So suddenly I had all the time in the world to do silly things like drive cross-country for a reunion.
The timing was pretty close though, I had a little over a week to plan it, pack the Tacoma and get to Cambridge MA.
I was still living in my pricy apartment in downtown Mill Valley, but I no longer had the software job to pay for it. Leaving it vacant for a month with no job prospects seemed kind of extravagant, so I sublet to a kid working at the Depot. That turned out to be kind of a disaster (another story for another post :), but that’s what I did.
Technology in 2000
Technology was different then. I publish this at the time as a series of emails from my pacbell.net account to a select list of friends.
- I would compose the emails at night in my motel bed.
- I would watch the weather channel in the morning to plan my day.
- Most motels had internet by then so I could shoot out that day’s report before I went to bed!
Pictures were with my trusty Canon SureShot. Every few days I would hit the Public Library whereever I was and upload my pictures from the camera to the laptop, and thence to the world!
Re-reading these, I had a much chattier style and seemed to be a more leisurely traveller back then. Technology was different. I take time to drop into the local library to check my email and maybe write a little bit.