AI Shoulder Surf V3

markdownlint-disable MD003 MD033 MD046

What follows is an AI summary of our meeting. The target audience is mostly the folks who were on the call, but I’ll be happy if anyone else gets something out of it.

On Thursday, May 28, 2026 we had our third AI Shoulder Surf. Thefirst writeup explains the format, but the short version: it’s an informal Zoom call where we share screens, talk about what we’re working on, and admit what we don’t know.

The connective thread this time was Tailscale: everyone at the table had quietly built a private home lab and was reaching it from anywhere without exposing a single port to the public internet.

markdownlint-disable-line

" Stop....hammer time? " by troy_williams is licensed under CC BY 2.0.# Olaf: Coach Claude

I have a triathlon coming up, so I asked Claude to build me a training program. I fed it a GPX file of the bike course so it could analyze the climbs and base the training around the actual route, then gave it my constraints — swim on these days, long run on a Wednesday — and it laid the whole thing out nicely.

As a bonus it generated a little static website for the plan. I spun that up on myHetzner VM and within about five minutes something had already tried to GET the.env file. It wasn’t being served, so no harm done, but it was a good reminder of what the open internet is like the moment you put anything on it. So I moved the whole thing onto my Tailscale network instead. Now my training plan isn’t getting probed by creeps — it’s just there for me when I want it.

The other nice touch: Claude also produced an iCal subscription and parks it in a GitHub gist. I subscribed to that URL from my phone calendar, and it actually updates when the plan changes. I’m happier with that than I would be wrangling a spreadsheet or paying a monthly fee for an app that doesn’t quite do what I want.# Aaron: A job-hunt workspace you can reach from anywhere

Aaron has been job hunting, and he hit the familiar problem of bookmarki…