Ten years ago, Tori Simokov says, she was "absolutely terrified" of flying, to the point that she often considered canceling trips. When Simokov entered a long-distance relationship with her now-husband, she was finally forced to confront that fear to travel from Ohio to New York City to see him.

Now, she's achieved an aspiring globetrotter's ultimate dream: quitting her job to focus on travel.

Simokov, 33, started Window Seat, a travel-focused Substack newsletter, in December 2023 as a creative outlet on the side of her full-time corporate job. Since then, her newsletter has amassed a loyal readership of over 5,500 subscribers.

In a May 9 post titled "I quit my job to write you this letter," she announced that she was leaving her full-time job as head of creative strategy at Complex to focus on growing Window Seat.

Quitting her job was a heavy decision for Simokov: "I wanted everybody to feel that weight with me, because it was something that I had just been working on for so long," she says.

Simokov describes Window Seat's content as "equal parts editorial and utility," featuring travel guides, financial hacks, product recommendations and interviews with other travel enthusiasts. Her goal, she says, is to make luxury travel "feel accessible for a new subset of travelers with taste."

Here's how Simokov achieved liftoff on her dream of writing about travel.

Preparing for takeoff

Simokov, who now lives in New York City, made $225,000 yearly in her previous role at Complex, which she describes as "a very, very high-stress job." She worked 60 to 70 hours each week and rarely had time to travel.

"I felt like I didn't have time to do anything else in my life besides work, which was really hard," she says.

After starting Window Seat, Simokov was pleasantly surprised when readers began to pay to subscribe within the very first month. By August 2024, she reached 100 paid subscribers, qualifying her as a "Substack Bestseller." 

Still, concerns about financial stability held her back from focusing on Window Seat full-time.

"I just kept thinking that this is what I want to be doing, but the money was what was holding me back," she recalls.

After over a year of juggling Window Seat alongside her full-time job, Simokov had an epiphany: "If I spent 100% of my time working on Window Seat, then how successful could it be?"

"Once that idea took root in my head, I couldn't think about anything else," she says.

At the end of the day, Simokov realized that she wasn't willing to trade "being able to see the world just in order to have a paycheck," she says.

In April, she gave her notice at work. Since then, she's planned two major upcoming trips: Menorca in July, and Portugal and Amsterdam in September.

Consistency is key

Subscriptions to Window Seat currently cost $7 per month or $60 for a full year, and Simokov makes an average of $930 each month from the newsletter. She hit the milestone of earning a cumulative $10,000 from her Substack subscriptions in April.

Simokov also runs a creative consultancy, V1 Projects, that currently provides most of her income. Subscriptions to Window Seat make up just about 12% of her total income, but Simokov hopes that her numbers will continue to rise: "Eventually, I want Window Seat to be the full-time thing."

In Simokov's view, one of the crucial ingredients to her success is consistency.

At first, she posted new content every two weeks, but since quitting her full-time job, she has accelerated to posting twice a week.

Additionally, she lists having a unique point of view and building community as her guiding principles for success on Substack.

"I'm still kind of figuring it out, but I've always been a pretty organized person," she says. "Right now I'm just kind of leaning on the skills that have always made me successful in that area, keeping a tight calendar, my to-do list, things like that."

'I don't feel any fear'

For Simokov, the most rewarding part of writing her newsletter is "knowing that what I'm doing has an effect on people."

After she wrote about her experience overcoming her fear of flying, a reader messaged her to share that Simokov's story had inspired her to tackle her own flight anxiety.

"She sent me a message, 'I'm looking forward to a lifetime in the skies,'" Simokov recalls. "It just touched me so deeply."

Simokov has experienced several other "pinch me" moments since starting Window Seat, including finding out that she has a famous fan.

Last October, actress Hailee Steinfeld reached out to Simokov via Instagram DM to tell her that Window Seat is one of her favorite newsletters.

Recently, Simokov was invited to LaGuardia Airport for a food tasting event hosted by Delta and Uber. ("You heard it here first: airport food is good now," she says.)

As a longtime Delta loyalist, it was "a dream come true" to meet airline personnel and get a private tour of the terminal.

"I came home and cried because it was such a full circle moment," she says.

The fact that Window Seat is now her full-time gig "hasn't fully sunken in" for Simokov, but she's feeling hopeful about the future.

"The big thing for me, which has been very, very new and something I haven't ever felt before, is I don't feel any fear," she says. "I was very much like, this is the right decision, and I just know that everything is going to work out."

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