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 Comple

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