I'm not always the calmest of travelers, but I've collected a few techniques that bring more ease as I prepare for trips. My favorite kind of travel doesn't involve an airplane at all. I like having room in my suitcase for everything I might need, plus the trunk of the car for more, and I enjoy driving one of our own vehicles, with a little bit fewer new things to learn on top of all the learning that travel already affords.
About a month ago, I traveled to Claremont, California for a conference at Harvey Mudd College: (Re)Imagining Liberal Arts and STEM Education in the Age of Generative AI. I heard about it from Josh Brake, a former guest on Teaching in Higher Ed. I shared more about the conference itself in a post about what we should know about AI, as well as a second one about finding value and meaning in a world of AI. For this one, I'll stick to how I prepared.
Cleaning up my packing list
I've used the Drafts app as my packing checklist for a long while, and both Dave and I have recommended it before. Over time mine had collected duplicates, and my categories had gotten messy. So I asked Claude Cowork to do a quick run-through: reorganize things more granularly, find duplicates, and suggest anything useful I was missing.
It didn't blow me away, but it caught a couple of duplicates and suggested some first aid basics, like band-aids and antiseptic wipes, that weren't a bad idea. My list is a variation of one Dave created and has used for years. What I like about it is that, alongside the expected categories (clothing, toiletries, health and medications, electronics and charging), he includes a section for “on person.”
The sections that keep me from forgetting
The “on person” section holds the things that are easy to forget on the way out the door, the kind that can make or break a trip: iPhone, Apple Watch, glasses (reading glasses, since I'm not going anywhere without the pair on my face), purse with wallet, backpack. I would rarely forget any of them, but I like marking them off instead of trusting that I'll remember.
More recently I added a second heading, “travel day items,” for things I can't pack the night before, like snacks that need to stay cold until morning. Small tweaks, but they have made a difference (especially in my stress levels).
My favorite new trick: Toggle Shopping Mode
Here's the part I got such a kick out of learning from Dave. Beyond tapping items on and off, Drafts has quick actions in a menu in the upper right. I've long used one called Checklist Unchecker to reset the whole list so I can reuse it for the next trip.
The new one Dave told me about solves a familiar annoyance: you're mid-pack, your phone goes to sleep, and you have to get back into wherever that list lives. The Toggle Shopping Mode action fixes that. Think of checking off a grocery list, then pausing to compare two products, and your screen goes dark. Instead, shopping mode creates a live activity, so the checklist stays right there in the Dynamic Island, that little black space at the top of the phone.
The whole time I packed, the Drafts indicator sat there, easy to return to. I left mid-day for this trip, so the list stayed live for hours. It even followed me onto CarPlay when I went walking with my friend Jeff, which I found particularly amusing. Talk about being reminded that I still needed to pack that day!

Dave told me about this Toggle Shopping Mode feature a long time ago and I didn't get it until I experienced it. If you already use Drafts, go install Toggle Shopping Mode, and then never look back.
Building a conference hub in Obsidian
The other thing I did involved Claude Cowork and Obsidian, my main note-taking app for under a year now. It's a plain text system, so the files live locally on my computer, though I pay for the inexpensive sync so I can reach them on other devices.
This conference had me like a kid in a candy store, and I wanted to squeeze every bit of learning out of it. The planning team curated a stupendous range of perspectives on AI, with keynotes, lightning talks, and longer breakout sessions, and I was overwhelmed trying to decide where to spend my time. I'd also signed up for a virtual facilitation workshop with a session that conflicted with one here. My mind was alive with possibility and, candidly, a bit of decision-making fatigue.
So I pasted the schedule into Claude Cowork, along with a transcript of me talking through the conflict and my thinking on the choices. For learning opportunities like this, I've been building what I call hubs in Obsidian: a linked table of contents that lets me move between related notes the way you would navigate Wikipedia (hyper linked).
Before long, Claude had co-created a hub with key details at the top (event, host, location, dates, website, schedule, primary contact, tags) and a description of what the conference would explore. From there it linked to everything else I needed:
- My personal schedule, once I'd settled it with Claude's help
- The full conference schedule, plus day one and day two
- People to try to connect with
- The organizing committee
- The recordings and materials
- The scheduling conflict I needed to resolve
- My travel and lodging info, which I keep in Tripsy, along with parking, campus and venue logistics, and the related tasks
It looks like a lot, but it was really just taking everything the planners provided and placing it somewhere easy to use. Because it's plain text and synced, I'd still have all of it on any device even without internet.
For the day one note, Claude turned my schedule into a simple table, easy to print if I had wanted a hard copy, with the time, session, location, and the part that makes it work: a link to a notes file for each session. Tapping a link opened a dedicated note, like the keynote “What should we know about AI?”, with the abstract, a few things to listen for, room to take notes, and a spot at the bottom for key takeaways, quotes, questions raised, and follow-ups.
Freeing up my mind
These two changes, Toggle Shopping Mode and the Obsidian hub, free up my mind for the creativity and learning a trip is really for, and cut the friction of remembering to pack or setting up notes from scratch. David Allen is famous for saying, many times:
Your mind is for having ideas, not holding them.
I think about that often. Even though it's taken me a while to sit down and write this (the conference was a month ago), I'm still turning over how much I learned. I look forward to continue to extend my learning through experimentation and future conversations for the podcast and am thankful to the conference planning team for such an enriching experience. That, plus to Dave, for continually teaching me things in life…
Resources mentioned
- Drafts — the note-taking app I use for my packing checklist, made by Greg Pierce / Agile Tortoise
- Toggle Shopping Mode — Drafts quick action that keeps a checklist live in the Dynamic Island
- Checklist Unchecker — Drafts quick action that resets a checklist for reuse
- Obsidian — my main plain text note-taking app
- Tripsy — where I keep travel and lodging information
- (Re)Imagining Liberal Arts and STEM Education in the Age of Generative AI — the Harvey Mudd / AXL conference I attended
- Josh Brake on Teaching in Higher Ed — how I first heard about the conference
- David Allen / Getting Things Done — source of the “mind is for having ideas” idea







