A Career Mistake That Got Me Fired—and Changed Everything (Tash Doherty)

My guest for Episode #302 of the My Favorite Mistake podcast is Tash Doherty, a British-Irish-American author, blogger, and podcaster currently based in Mexico City. A graduate of the Wharton School at the University of Pennsylvania, Tash previously worked in analytics for Postmates and Vox Media.

Episode page with video, transcript, and more

Today, she is the creator of Miss Educated—a popular blog and podcast covering business, pleasure, and women's health. Tash is also the author of the coming-of-age young adult novel These Perfectly Careless Things, self-published in 2023. She gained viral attention on TikTok by openly sharing her experiences with birth control.

Fresh out of Wharton at age 23, Tash joined Postmates in San Francisco, working in analytics. When offered a team change, Tash ignored her gut instinct and reluctantly joined a team run by a manager whose working style clashed sharply with her own. Within months, their professional relationship deteriorated, leading to Tash's unexpected firing just two weeks before the company conducted widespread layoffs.

Initially painful, this mistake forced Tash to reassess her career direction, ultimately opening the door to writing, entrepreneurship, and creative independence—turning a devastating setback into her favorite mistake.

In this episode, we also discuss Tash’s insightful critique of technology companies and their unintended contributions to economic inequality, her process of transforming a teenage passion project into a published novel, and practical advice on balancing creativity with financial sustainability.

Questions and Topics:

• What’s your favorite mistake?
• Were there early signs of trouble with your boss, Sumit, or did problems develop later?
• How did you choose Postmates as your first job after graduating from Wharton?
• Did your poor relationship with Sumit impact your job performance?
• Was it hard to trust another company or manager after that experience?
• Did you ever consider starting your own company again after leaving Postmates?
• Do entrepreneurs have a responsibility to reduce economic inequality, or is that up to policymakers?
• What specific mistakes do you see tech companies making right now?
• What led you to write your article, "How Tech Is Ruining the World"?
• Can you elaborate on how tech companies like Postmates worsen inequality?
• What did you mean when you described tech workers as being "incurious about the machine"?
• Is the tech industry truly improving society or causing greater harm?
• How should entrepreneurs or policymakers handle technologies that cause harm when scaled?
• Tell us about writing your book, These Perfectly Careless Things—how did it evolve over time?
• How do you decide when your writing is finished and ready to publish?