Window Seat

Window Seat

Reader Q&A: Travel trade-offs, points from scratch, and and a new chapter

Answering questions like how to think about upgrades and travel without burning out

Tori Simokov's avatar
Tori Simokov
Jan 21, 2026
∙ Paid

Welcome back to another edition of reader Q&A! I’ve started incorporating these every so often because they have become a pulse check of sorts.

They show me how people are thinking right now: what you’re prioritizing, what you’ve been questioning, and where you maybe are craving a little more clarity. I love getting insight into your thought processes because it helps inform my own work, so thank you for sharing them with me.

Read on to learn:

  • A life update I am very excited about

  • The biggest travel mistakes I see people make again and again

  • The one credit card I would choose if I had to start from zero

  • My honest take on whether it’s too late to start a Substack newsletter

  • Which souvenir I wish I saw more hotels offer

As always, these reader Q&As are not just for travel questions, they’re a chance to get to know me a little better, too.

Making me happy lately: meeting up with internet friends + spending time with family (aka my puppies)

What are the biggest mistakes you see people making travel-wise? —Emily

Optimizing trips at the expense of your own enjoyment. I understand the appeal of trying to see as much as possible—I used to do it myself. But once I learned to slow down a bit and prioritize my own exploration and discovery over checking off boxes, traveling became so much more fulfilling.

Another big one is defaulting to the cheapest option without considering what it’ll cost you in terms of energy, time, or stress. For example, paying extra for the direct flight or the hotel in the city center and writing off the expenses as strategic, not indulgent.

Sooo you’re moving?? Are you staying in NYC? Tell us more! —Molly

This post is for paid subscribers

Already a paid subscriber? Sign in
© 2026 Tori Simokov · Privacy ∙ Terms ∙ Collection notice
Start your SubstackGet the app
Substack is the home for great culture