One year in the window seat
How I built a bestselling newsletter from scratch (and what I’d tell anyone starting out)
In my first letter, published one year ago today, I likened the experience of starting a newsletter to being afraid of flying. Both were scary, but I used exposure therapy—doing the hard thing over and over again—to overcome the latter. I hoped it would also help with the fear I felt in hitting “publish” for the first time.
What was I so afraid of? For one, the “Substack boom” both excited and discouraged me. Seemingly everyone was starting a newsletter…did that leave room for me? I worried about how I would carve out my own space. I worried about being seen shouting into a void.
Ultimately, I worried about failure.
Of course, “failure” is completely subjective here. What does it mean to fail when starting a newsletter? Is it not amassing a certain number of subscribers? Is it getting no engagement? Is it not sticking to a set publishing schedule? Is it not providing readers enough value? Some of these things were within my control, some weren’t.
Fear kept my first letter pretty low-stakes. In the midst of shopping links and some travel news that I sent to maybe 50 subscribers, I offered only the tiniest glimpse of vulnerability. It was the equivalent of sticking a toe in the water to check the temperature before diving in. I didn’t know what I was getting into, what I wanted the letter to become, or how seriously I would take it. I told myself I could figure it out as I went, so that’s what I decided to do.
It’s worth noting that Window Seat is not my first creative endeavor. Five years ago, I launched a brand called New York Old Friends. It was conceived to marry my marketing experience with my design skills; I thought it would be fun to make merchandise in the form of my own label and, surprisingly, it actually was pretty successful. I always sold out of my products, secured organic press hits, and eventually collaborated on a 20-piece collection with streetwear legend Jeff Staple.
I say all that to say: starting another creative project—this newsletter—shouldn’t have given me so much anxiety. But I felt a huge divide between monetizing a skill I believed I was good at/had been doing for a long time (design) and monetizing a skill I feel I am still developing (writing).
But here’s the thing: a year later, Window Seat has grown beyond my wildest dreams. It’s not a big letter by any stretch, but I’ve been able to grow an audience and create a publication I’m proud of, which is more than enough for me.
To celebrate a year in the window seat, I’m sharing insights from my journey of starting creative projects and the lessons I’ve learned that can guide you toward achieving your own unique definition of 'success.'
Lesson #1: just start.
Here’s what I think is the single most important thing you can do when dreaming of any creative project: Just. Start. This reminds me of a sentiment
posted recently in a note:“Just make it EXIST first. You can make it GOOD later.”
When it comes to newsletters, you don’t need to have a business plan, brand guidelines, or a full-blown editorial calendar or content strategy figured out before you publish. You just need a perspective.
My only strategy when launching Window Seat was (and still is) I am my own audience. When I write, I write to myself. I know that if something resonates with or is meaningful to me, it will resonate with or be meaningful to someone else. It might take you a minute to find those people, but if you stick with it, you will. Whenever I second-guess a letter I’m about to publish, I remind myself of this—and for what it’s worth, the letters I’ve doubted the most have been some of your favorites.
Lesson #2: build it (and stick with it and have patience) and they will come.
It’s hard to stay consistent in the beginning when it feels like you’re writing to no one and who cares what you have to say and why you are even doing this and all the self-doubt and insecurity start to creep in. But you have to stick with it and stay the course.
It’s also important to stay consistent once you start growing an audience. I know firsthand: there was one month where I didn’t publish anything. I was unexpectedly laid off from my full-time job and then started a new, very demanding job a couple of weeks later. I didn’t have the time or energy to write and this letter suffered for it. I lost a lot of subscribers. People like knowing what they’re getting from you, so once you set a schedule, keep to it.
Lesson #3: community is everything.
I think the best part about Substack (the platform I publish my newsletter on) is the community here. In my experience, the people here are very friendly and open; it’s been easy to find like-minded writers to connect with.
Building community makes it easier to stay the course when it feels like you’re writing to no one. You cheer each other on. Personally, I like rooting for other people’s success—I think there’s more than enough to go around. I go out of my way to open letters in my email that I’ve already read on Substack just to boost the open rate. I try to always click a link, and I’ll always leave a like or comment. A little goes a long way here, and what you put in, you tend to get back tenfold.
Essentially, my North Star has been staying true myself and my interests, and I can say now—a whole year in—that it has paid off. The biggest reward in how Window Seat has grown isn’t the subscriber growth or the Bestseller badge, it’s the validation that trusting my instincts has resulted in real readership and resonance.
I am beside myself with gratitude to each and every one of you; everyone who has ever taken the time to engage; anyone who has ever forwarded or shared a letter; those who have paid for subscriptions or gifted them; from the bottom of my heart, thank you. It is the most meaningful gift.
***UPDATE: GIVEAWAY CLOSED.*** In the spirit of community and giving back, I’m giving one lucky paid subscriber a bundle of my favorite travel products (worth over $1,000!).
To be entered to win, all you have to do is be a paid subscriber on 1/1/25. I’ll randomly select a winner on that date and notify them via email. Paid subscriptions are discounted right now to just $4/month or $32/year.
The giveaway includes: an Away carry-on suitcase, a large Away Featherlight Tote, an Away crossbody bag, an Away luggage tag, a Calpak luggage tag/phone charger, Goop cream blush and Instant Glow Exfoliator, Summer Fridays Jet Lag Mask, The Outset Lip Oasis treatment, Vacation sunscreen, Soft Services Smoothing Solution, Necessaire Eucalyptus body wash, French Farmacie Elixir Exfoliant, and a black (one-size) set from NEIWAI (top + bottom)
Inspired by
’s genius Wrapped, here’s what happened in the world of Window Seat:In 2024, Window Seat became a Bestselling publication (thank you!! 🥹) and was featured on Substack Reads. Currently, it is read in 46 states and 74 countries, and 27 publications recommend it to their readers—thank you to
, , and (and all the other letters who recommend Window Seat)—for your support! It means the world.Your favorite letters I published this year were about my travel essentials, how I navigate the airport, along with my guide to Paris.
These were the most-purchased items out of all the products I recommended:
I featured 8 different tastemakers on my Seatmates interview series; these were the top issues:
Lastly, Window Seat was featured in so many different newsletters this year. I’m beyond thankful to all of these amazing voices for helping me find community here and for sharing my perspective with your readers. ♡
13 Substack Writer’s Election Week Strategies by
My Favorite Newsletters, Including 17 Exciting Emerging Voices by
Consider Yourself a Shopper #33: What’s In My Toiletry Bag? by
9 Incredible Airbnbs worth building a trip around by
What are the best cute sneakers for travel? by
The Eloping Bride’s Guide to Wedding Attire by
Speedy Boarding with Tori Simokov by
Away x La Ligne: Stripes & Travel Gear by
Thank you for reading and for coming along for the ride. I don’t know how 2025 could ever top this incredible year, but here’s to trying. 🥂 Cheers!
This post contains affiliate links, which means I may earn a commission if you make a purchase (at no cost to you).
Tori Simokov is a Travel Writer and Graphic Designer/Strategist based in New York. To get in touch, email tori@v1projects.com. Want more? Check out Instagram, TikTok, or shop her curated favorites.
Congratulations, Tori! I've loved following along and watching Window Seat grow this year. ❤️
Congrats, Tori! I'm so glad I discovered your newsletter. I recently celebrated my one-year anniversary on Substack and found your insights very helpful.