Episode Summary

In this episode, Meghan O’Keefe discusses her journey from aspiring comedian to becoming a prominent figure in digital media at The New York Post's Decider.com. Over Hendrick's and Tonics, Meghan reflects on her early days in the comedy scene in New York, her transition into entertainment journalism, and her current role where she influences how streaming content is perceived and reviewed. The episode delves into the nuances of media and comedy, exploring how Meghan's personal experiences shaped her career path. She candidly discusses the challenges of finding her voice in a male-dominated industry and how her shift from comedy to journalism led to a more fulfilling career. This conversation not only highlights her professional evolution but also touches on broader themes of media influence, personal growth, and the unpredictable yet rewarding nature of creative careers.

Quotes:

"I was really depressed and then when I finally started to get stuff together, I went back into comedy a bit. I started getting more confident in Boston. It’s kind of making me want to die. And not only that, but I’m seeing friends get big breaks and they don’t seem happier."
"I always loved writing of any kind. And this, I was just really struggling and as I was starting to get like, you know, when Mark was coming to me with the cider at the same time, someone else was trying to get me for their site. And I started to realize, Hey, this entertainment journalism thing I like, and I'm good at it and doors are opening."
"The advice I try to give to like, the interns we talk to at Decider is like, you’re so young and your life ahead of you and if anything I’ve learned from my meandering path is that you should be open for the idea that your dream could change."

Key Takeaways:

The importance of being adaptable in one’s career, highlighting how shifts in interest and industry can lead to more fulfilling opportunities.
The emotional and professional resilience required to navigate the volatile nature of creative industries, particularly in shifting from comedy to journalism.
The personal growth that comes from self-reflection and openness to change, which can lead to discovering one’s true passion and niche within a broad industry.

The Monday Microsegment for the week of 7/7/2025