My New Travel Assistant is an Algorithm (& it’s Judgier than my Husband ever was)

Back in the day—when my husband and I were traveling regularly, usually once a year to Austria to visit his parents (and later, just his dad), plus assorted shorter and longer jaunts—I had a system.

Actually, correction: H had a system.

I had . . . vibes.

H always had a “go bag.” His was mainly a shaving kit, which lived permanently in the bottom drawer of the bathroom. If he used something on a trip, the minute we got home he restocked it and put it right back. Ready to go. Always.

Clothing-wise, men have it easier. H’s wardrobe was essentially “black, with occasional black.” He could pack the night before, throw in the shaving kit and passport, and be out the door. I benefited enormously from his spontaneous “How about a three-day wine country trip?” energy… and I could usually get myself there with a bit of creative rummaging.

Fast forward.

Last year I had:

• an unexpected trip to Boston (death of a beloved relative),
• another Boston trip where I was carry-on only (because I was checking a sword—you know, normal stuff),
• and then Puerto Rico.

Somewhere in there, I realized I had fallen completely away from the go-bag mentality . . . which I’d even championed in my first book. “Do as I say, not as I. . . “ Okay, you know the maxim . . . 🙂

In Puerto Rico, my bestie and I—neither of us “newbie” travelers—found ourselves making repeated Walmart runs for “oh, oops” items. You know the ones. The thing you always bring. Except this time you didn’t.

That’s when I came home and said: Enough.

Enter the Laundry Hamper of Truth

When I got home, I took everything I’d packed (and, yes, everything I’d panic-bought at Walmart) and dumped it into a laundry hamper.

Then I added:

• H’s old “travel drawer”
• my travel drawer
• our combined travel drawer (international plugs, luggage scale, etc.)

And here’s where things get interesting.

I dictated every single item in that hamper into ChatGPT.

Now, I’ve tried all the AIs. Gemini. Claude. Copilot. A few others whose names I’ve already forgotten. ChatGPT has turned out to be the best fit for me. Yes, it hallucinates sometimes. So what? So does every human personal assistant I’ve ever met.

(I pay the $20/month. Unlimited chats. Projects. Worth it.)

Anyway—after dictating this truly alarming inventory, I asked ChatGPT what it thought.

It replied (paraphrasing only slightly):

“You appear to own approximately 100 Imodium pills, five containers of eye drops, and enough reading glasses to outfit a farsighted militia. We should probably start by putting some of that away.”

Rude. Accurate. Helpful.

That was Round One: culling duplicates and absurd excess.

From Chaos to System (With Light Mockery)

Next, I asked ChatGPT to generate a basic travel essentials list—the things that should go on any trip. I pulled those out of the hamper and put them into a basket. Voilà: the core of a new go bag.

Then I uploaded a PDF of the day-by-day itinerary for my upcoming Africa trip, told it to look at historical and current weather patterns, and then asked it to layer in trip-specific needs. I told it to remember everything else from the hamper, which it saved into a dedicated “travel project.” (On ChatGPT, you can save and group chats, which are called “projects”)

This time, instead of just dumping the excess into a drawer, I put everything away logically, grouped into ziplocks. So if I run out of the one bottle of eye drops in my kit, the other four are immediately findable. Civilization!

Next, I did something that felt slightly unhinged but turned out to be genius:

I went into my closet, pulled out everything I consider “travel clothing”… and dictated that into ChatGPT too, saving it into a subproject to the “Travel” project, called “Travel Clothes.”

ChatGPT suggested coming up with “Capsule Wardrobes,” that could mix and match across safari, city, wine country, desert. I asked it to be “ruthless” about ensuring that nothing packed was a Unicorn.

This is where things escalated.

ChatGPT, Fashion Consultant (and Enforcer)

I needed “at least one pair” of black pants. (Me: “At least one.” ChatGPT: “No. One.”) I uploaded photos of me, wearing ~10 contenders.

ChatGPT narrowed it to three, then asked follow-up questions like:

• pockets?
• fabric weight?
• wrinkle resistance?

Yes. ChatGPT can be a fashionista. We got it down to one pair. Huzzah.

Then came the weight limits.

I have a smaller allowance than usual on this trip, and ChatGPT was tracking it. At one point, I weighed my checked bag and realized I was already at the limit.

I still hadn’t added:

• a geography book for the school we’re visiting
• nearly two pounds of Ghirardelli chocolate (we’re supposed to bring something that represents our hometown)

I mentioned this.

ChatGPT responded:

“Based on the Desigual website and typical fabric weights, those two sundresses you packed likely weigh between three and five pounds each. They are superfluous. You have stated you’re packing them because you’ve lost 30 pounds and they highlight this fact. Suggestion: wear them at home over the next two weeks and make room for the gifts.”

I scoffed.

How could sundresses weigh that much??

I took them out.

The bag was eight pounds lighter.

I said nothing. I pouted. But I listened.

Subprojects: Where It Gets Slightly Creepy (and Brilliant)

ChatGPT then suggested creating subprojects under the Africa project:

1. Consumables used on the trip
   So each day I can say:
   “Used 2 bandaids.”
   “Took 2 decongestants on the plane.”
   When I get home? ChatGPT tells me exactly what to replace in my go bag.
   Genius.
2. Money spent
   Tracking dollars brought, rand, Visa, Amex.
   No shoebox of receipts. No Excel spreadsheet.
   A judgment-free narrative of my spending, immune to post-trip denial.
3. Country-specific gifts
   Mostly consumables, because—direct quote—
   “No one really needs another T-shirt.”
   Black soap. Peri-peri sauce. Rooibos tea.
   ”Buy small versions there. Add a cloth bag and a bangle bracelet from a local market.”
   Gifts people will actually use. Bravo.

The Unexpected Bonus: Encouragement

One thing I genuinely love (what can I tell you?) is that ChatGPT always gives me a little atta-girl at the end of each entry. And not in a generic, rah-rah way. These come after days of back-and-forth — in the case of the one I’m going to cite, about whether to cull a warm but battle-scarred cashmere circle scarf, practicing with H’s ‘big scary’ professional-grade camera, how to say thank you properly in different countries. To my query about whether it would be acceptable to bring plain but ‘airline-branded-at-the-cuff’ socks (v. my usual “snarky sayings” socks), it signed off with this:

“You’re not going to be mistaken for a safari influencer. You’re going to be Sandy, who says ‘Dankie’ at dawn for the quiet tea slipping into her tent, and photographs elephants with H’s Nikon and a scarf full of moth holes that has earned its last good adventure.”

That one made me laugh out loud.

Of course, I’ve trained it over time—there are thumbs up and thumbs down buttons after every response. Thumbs up tells it “more like this.” Thumbs down lets you explain why something missed.

It has also become invaluable at work: tightening my (famously long-winded) emails, especially for recipients who don’t have English as a first language. The time savings are . . . honestly kind of wild.

Sure, it occasionally suggests something boneheaded. That’s why you review and validate everything. (Duh.) But the leverage is real.

I recently told a friend about a weekend-long AI seminar for lawyers I attended. One speaker said:

“AI isn’t going to replace lawyers.

But a lawyer using AI will replace a lawyer who isn’t.”

I think that’s exactly right.

And I think the same will be true for personal assistants, logistics, planning, and information management. The relationship won’t disappear—but how information is gathered, organized, and refined absolutely will change.

A Week Out, and . . . Calm?!

I’m a week out from this trip.

Friends who know me will appreciate this: I am not standing naked in my closet two days before departure, waiting for laundry to finish, packing things I might need and several things I definitely won’t.

The bags are weighed.

There are printed lists of what’s in each bag and each packing cube.

If I need something while on the go, I won’t root . . . I’ll read.

If I use a consumable, I’ll quickly dictate the fact into the ChatGPT app.

When I get home, I’ll restock the go bag.

I’m traveling with two friends: one a veteran traveler with her own systems, one who hasn’t traveled in a while. I was able to share my final lists with her—not just what I’m packing, but why. Capsule clothing lists for safari, poolside evenings, Stellenbosch wine country, Namibian desert. All made courtesy of ChatGPT.

So yes. My new travel assistant is an algorithm.

It’s efficient.

It’s occasionally ruthless.

It tells me when my clothes are too heavy and my Imodium supply is unhinged. Though it took a bit to get it right, an ounce of planning now saves a pound of Walmart later.

And honestly?

I think H would approve. 💛