Opera, Wall Street, and a Career Nobody Could Have Written

Jen Litwin is my favorite kind of guest. Her story started with one thing (opera), embarked into a seemingly opposite career (Wall Street), and somehow found herself exactly where she needed to be. When you hear it, it all makes perfect sense even if getting there was anything but perfect. Jen trained as an opera singer at Oberlin and Yale and went on to perform professionally at the highest level. Then, a leader at AIG (where she took a temp job on a trading floor just to pay the bills) told her something that would change everything: as an opera singer, she had all the skills necessary for the trading floor. She wasn't sure she believed him. But the offer was on the table, and Luciano Pavarotti wasn't calling. So she stayed.She spent decades in financial services, then started moderating panels, then coaching. Then someone sent an email with the subject line "The world is not right if you two do not know each other" — and she landed at Speeko, an AI-powered coaching platform where she now leads coaching and strategic partnerships. Today she still teaches music, still performs, and coaches leaders and teams on the one thing she's always understood better than most: the power of your voice.At every step, she felt like she didn't quite fit the box. So she stopped trying to fit it and built something better.This episode is about what happens when you stop trying to be one thing, and what it means to finally find the container that holds all of you.We talk about:What opera training actually builds in a person (hint: it's not just a voice)The conversation that changed the trajectory of her career (and why she almost said no)What presence, gravitas, and confidence actually mean (and how anyone can build them)Her practical advice on navigating the unknown with graceWhy your network isn't a strategy, it's infrastructureThe communication mistakes even the most high-performing people don't know they're makingJen's voice, both literal and figurative, has been her through-line all along. She just needed time to figure out what it was all for.Chapters (00:00) Introducing Jen Litwin(01:03) From Opera to Wall Street(04:00) The Conversation That Changed Everything(09:13) Learning the Floor: What Wall Street Actually Taught Her(11:26) The Long Way Around: From Trader to Facilitator(16:25) The Snowstorm That Made Her Career(21:55) The Moment She Knew Voice Was Her Work(27:34) When the Mosaic Finally Came Together(32:01) Why Relationships Are the Real Infrastructure(36:27) Presence, Gravitas, and the Myth of "You Either Have It or You Don't"(39:30) The One Thing That Fixes Almost Everything (It's Your Breath)(44:27) How to Reframe Nerves as Excitement(50:46) What Speeko Does That Coaching Can't(54:09) The Communication Mistakes Even High Performers Make(1:03:04) The Script She Most Needed to Quit(1:05:32) What She's Proudest OfWhere to find Jenhttps://www.linkedin.com/in/jenniferlitwin/https://www.speeko.co/Spotify For more from The Unemployment Diaries https://substack.com/@aishaommayahttps://www.instagram.com/theunemploymentdiariespodcast/