Dagan Thogerson has played over 2,000 shows in his career, including 15 years behind the kit for the legendary indie-rock band Murder by Death. He joins Tom to peel back the curtain on the "Road Dog" lifestyle and the transition from a 16-year-old playing biker bars to a professional session musician.

We dive into the "B-Side" of the music industry: the part that involves spreadsheets, ticket counts, and boundaries. Dagan explains why the most important skill for a touring professional isn't how fast you can shred, but whether you're a "good hang" who is reliable and accountable when things get messy - a truth that translates directly from the tour van to the office.

Lindsay McGuire was a SaaS powerhouse, a director-level "titan" in the Indianapolis tech scene. But deep down, she felt a calling back to her community. She joins Tom to discuss the psychological hurdle of walking away from the "golden handcuffs" of software and the pivotal advice from her mother that changed everything.

Now the Assistant Director of Advancement, Branding and Outreach at The Milk Bank, Lindsay discusses the "revolutionary" shift from marketing software to saving infants' lives in the NICU. We dive into:

• The Fear of the Jump: Overcoming the internal monologue that says leaving a high-level role is "stupid."
• Public Health vs. MarTech: Moving from the "fight or flight" of software trends to the thoughtful, high-stakes pace of community health.
• Junior League & Capacity: How to give back without burning out.
• The Metaphysical B-Side: A hilarious and brilliant story about how selling Thor’s hammers and "potions" at a jewelry store became a jumping off point for her content marketing career.

Rebecca Fleetwood Hession spent 20 years in corporate sales before realizing she was living in a state of constant dysregulation. Now a professional coach marking her 10-year anniversary, she joins Tom to discuss the science behind why we stay in jobs that chew us up.

We dive into the "Same = Safe" paradox: the nervous system's tendency to choose known pain over the uncertainty of change. Rebecca explains why great leadership requires self-care to keep the prefrontal cortex online for decision-making, and why the "billboard" style of top-down communication is killing team commitment. Whether you are an executive or a founder, this episode is a masterclass in why business is, and always should be, human.

What does the first year of a marketing career actually look like? Madison Stiles and Noah Burlingame join Tom to peel back the curtain on the transition from Indiana University grads to full-time agency professionals.

We dive into the "Welcome to the Jungle" reality of learning cross-channel marketing, why your GPA matters significantly less than your "vibe check," and the danger of comparing your job search to your friend's group text. Whether you are a junior in college or a recent grad feeling "behind," this episode is a guide to navigating the autonomy of remote work and the importance of getting comfortable being uncomfortable.

Every afternoon at 3:00 p.m., the clock resets for Araceli Gomez-Aldana. A veteran journalist and reporter at WBEZ, Araceli joins Tom to discuss the "Groundhog Day" reality of the news cycle and why her career is defined by a Harry Nilsson song.

From her roots in a small town in the Chicago Region to a prestigious fellowship at Stanford, Araceli breaks down the unglamorous truth about breaking into media today. She talks about why the "prescriptive" career timeline is total bullshit, how to build a portfolio when no one is hiring, and the high-stakes world of waiting for sources to call you back. She also dives into the discourse around AI in the newsroom and why vertical video might be the only way to save attention spans, and critical thinking, in 2026.

Sophie Hunter is the founder of Sorella Creative and a social media strategist who's worked in fast fashion and now thrives as a freelancer. She joins us to talk about the BRUTAL reality of catastrophizing your way through a marketing career, and somehow succeeding anyway.

Sophie's story is a masterclass in authentic self-awareness. She shares why marketing yourself feels "icky" even when you're literally a marketer, how she went from Brutal by Olivia Rodrigo energy in fast fashion to Hand in My Pocket balance in freelance, and why she keeps a folder called "REMEMBER" filled with screenshots of nice comments for when imposter syndrome hits hard.

She breaks down the unexpected challenges of going freelance (spoiler: it's not the work, it's the micromanaging clients who want pink heart emojis), why ChatGPT can write your content but shouldn't, and why maybe your new year's resolution should be "boundaries", too.

Plus, learn why the Smiths will always transport her back to her Tumblr days.

Brian Talbot's career is a masterclass in flexibility: from trying to be a "radio god" and selling ad time to becoming a voiceover artist and now a high-level Fractional CMO. He joins Tom to prove that in every role, especially sales and marketing, the most critical asset is simply being yourself.

Brian dives into why authenticity is the only differentiator left in the age of AI, and how he learned to embrace his own voice (literally, by inventing a "Brian's normal voice" character). We discuss why setting boundaries with clients is not only acceptable but essential for long-term partnership, and why CEOs need to stop viewing marketing as a black hole.

Plus, Brian breaks down his successful scaling framework, the Market, Message, and Map, and shares the tough conversations required to get leadership buy-in and turn a team's Net Promoter Score around.

Lisa Levey, a veteran reality TV producer and editor who's worked on Real Housewives of New Jersey, Bravo shows, and more, joins us to talk about the brutal reality of freelance life, why AI can't edit reality TV yet, and the stories nobody asks about.

Lisa's journey is a masterclass in sustainable creative hustle. She shares why living in constant fear is actually her superpower, how she's never had a traditional job, and why the process of making TV matters more than the finished product everyone obsesses over.

She breaks down what really happens behind the NDA-protected walls of reality TV, why everyone wants to know about the Housewives but nobody asks about the thousands of hours of footage it takes to make a 30-minute episode, and how she's built a career without ever feeling secure.

Hear Lisa get incredibly real about her side project, The Otherhood Collective, which tells stories about family, parenthood, and the paths that don't fit into society's neat little boxes. Plus, learn why her theme song is "Work Bitch" by Britney Spears and why that's actually perfect.