Advice Q&A: My best travel packing advice
How to stay sane and not crash out, and actually wear everything in your suitcase
We are in the midst of summer and as I’m about to go on a few adventures myself, this question for my advice column came at exactly the right time.

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My inaugural advice column kicks off with a question from Debbie, who said she needs help with:
PACKING!! it’s so frustrating - no matter how hard I try to pare down, I always pack too much! Also, I misjudge the weather… thinking oh it will be hot but then realizing I need a warm layer which I didn’t bring. Also I pack into a small rolling bag (or two, sometimes, for a longer trip) and like to go carry-on, esp. if I have to change planes. Any wisdom, tips, therapy advice appreciated!
Well Debbie, you’re in luck because not only have I written on the subject of packing and how to do it well (read: like your suave, sophisticated self belongs and blends rather than sticks out like a loud American tourist), but as a seasoned world traveler I, too, am curious about how others manage multiple day or weeklong trips with carry-ons only.
Along with my list of 10 essentials for air travel, here are my other tips:
Today’s newsletter: Carry-on packing, closet indexing, and cookie-stuffing-gate
To try: Sudoku method
Recently, I came across this potentially groundbreaking Sudoku method of travel packing:
The resource below offers a bit more detail, despite the fact that I do not share the same fashion sense nor style with the writer, e.g., I do not own a single thing from LuluLemon.
But the logic remains: Every item in your suitcase should at least go with one other thing, be it a shawl or accessory or shoe.
I will not bore you with even more templates from luxury travel advisors nor images of capsule collections for things that you may not already own, but this is definitely a more mindful way of packing that I’ll try in the coming weeks, and report back if it’s a success.
The good news is that on my last 9-day trip, I did wear everything I packed in my suitcase. Yay!
I’m Shindy. I sold my financial content company and now I write this weekly culture, money, and lifestyle Substack. I’m a journalist and bestselling author featured in Forbes, The Wall Street Journal, Business Insider, Bankrate, Cheddar TV, and HuffPost. If you haven’t yet, and would like to join more than 7,200 people on the internet who I call my “shin-siders” then tap this button right hee-ya:
To try: Indyx
As for combing through your wardrobe, one thing I’ve begun doing is indexing my closet.
I have two closets: one in Miami and one in Charlotte.
I need to figure out what’s where.
Enter Indyx (not an ad). I first read about it in New York Times Wirecutter, and while I’ve tried other clothes indexing apps before, I always gave up out of lack of utility.
It was a matter of time before something better came along, with the ability to tag, label, and work within the app, like create outfits.
For my upcoming vacations, I will log everything I pack into Indyx.
I use the free version, because I don’t feel the need to connect with others, or consult styling advice.
What I am enjoying is gaining insight into what I have and don’t need more of.
Of course, the worst part of these fashion logging apps is the effort required to log all of your clothes.
It’s a slog, and I dedicated about two hours to catalogue my Miami closet, but I’ll get there.
What about you? Have you tried either the Sudoku travel packing method, or how do you keep track of what you own?
📺 I’m watching:
Widow’s Bay, Apple TV. On the last ep!
📚 I’m reading:
I’m between books at the moment.
As in, I’ve downloaded a few samples here and there, but like a fussy baby that won’t latch, I’m finding it difficult to stick to anything beyond the first 10 pages.
I’m headed to two beach destinations over the next month and would love some recs, so please drop your latest, most riveting, must-read summer fiction below:
In the lull, I’ve been catching up on business news to fill the void.
Shopping app Phia has been accused of skimming commissions from retailers and creators. The app, an AI-powered tool that helps you locate the lowest prices while buying (mostly fashion) online, is not notable (I never used it) except that it’s co-founded by Phoebe Gates (yes, that Gates).
My Substack algo and circle is heavily New York- and marketing-girl-adjacent, so this has been all over my feeds.
It’s amusing to see all the commentary, equal parts cackling glee and mean girl; people just love a female founder takedown story.
Through dastardly code that was injected behind the scenes, the company was helping themselves to revenues that belonged to other retailers and creators.
Here’s the original Bloomberg report plus an Inc. breakdown on the issue.
Also, Ali Kriegsman has been doing stellar reporting on this, suggesting that at the same time Phia stopped working with the affiliate service ShopMy was when this cookie-stuffing-gate started.
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Until next time,
Shindy
On Instagram + TikTok
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hmmm the Sudoku square maybe (I don’t play Sukoku) but this makes so much sense: “Every item in your suitcase should at least go with one other thing, be it a shawl or accessory or shoe.” thank you Shindy!
In traveling next week and will try the Soduko method! Although I'll definitely add a dress (or two.) As for book recs, I really enjoyed The Fountain by Casey Scieszka which no one is talking about and I can't figure out why!