In this episode of 'Sh*t I Just Quit My Job,' host Maricella Herrera dives into a candid conversation with Megan Senese, a legal marketing and business development expert who co-founded the company Stage. Maricella and Megan discuss the challenges of navigating career shifts, dealing with corporate burnout, and the importance of authenticity in business. They explore Megan's transition from the corporate legal world to entrepreneurship, the strategies she used to build her business from the ground up, and the vital role of relationship building in professional success. Megan also shares valuable insights on personal branding, navigating layoffs, and the significance of doing things differently in a crowded market. The episode ends with Megan's advice to her younger self: just hold on, it will be over soon.

About Megan Senese:

Megan Senese is a legal marketing and business-development entrepreneur and co-founder of Stage, where she helps lawyers grow their practices through authentic relationship-building and strategy. She is especially admired for her ability to bring empathy and genuine human connection into an industry often driven purely by numbers.

Show Notes

00:00 Podcast Introduction

04:30 Childhood Dreams vs. Reality

21:06 The Big Quit

23:36 Pandemic Burnout and the 2% Raise

32:25 Unlearning Corporate Toxicity

35:47 The Leap to Entrepreneurship

42:04 The Thousand Meetings Strategy

49:23 Business Development Advice

51:21 Going Unhinged on LinkedIn

55:06 The So Much to Say Podcast

58:43 Final Advice: Hold On

Takeaways:

1. The podcast delves into the complexities of personal reinvention, particularly after quitting a job that was once deemed defining.
2. Listeners are encouraged to embrace the chaotic journey of self-discovery and the uncertainties therein, recognizing that it is a universal experience.
3. A significant theme discussed is the importance of authenticity in business, suggesting that one can still be themselves while building a successful enterprise.
4. The speakers emphasize the necessity of building genuine relationships and connections rather than relying solely on traditional networking methods.
5. The conversation highlights the emotional and psychological challenges faced during career transitions, particularly in acknowledging and navigating grief associated with leaving a familiar job.
6. Insights are shared on the evolution of personal branding and visibility in a digital age, stressing the need for uniqueness in content to stand out.

In this conversation, Denis Keane shares his journey from a corporate career to entrepreneurship, highlighting the challenges and lessons learned along the way. He discusses his experiences in the nightlife and restaurant industries, the importance of people skills, and the role of adaptability in navigating the ever-changing landscape of startups and technology. Denis emphasizes the need for risk-taking and the value of understanding business fundamentals, while also reflecting on personal growth and self-worth.

Show Notes

This episode presents a profound exploration of career transitions, personal growth, and the entrepreneurial spirit through the lenses of Maricela Herrera and her guest, Denis Keane. The narrative begins with Maricella's honest reflection on her struggles with motivation and the emotional toll of returning to her routine after a significant hiatus. Her vulnerability lays the groundwork for a rich discussion with Denis, whose dynamic background as an entrepreneur in the nightlife and technology sectors illustrates the multifaceted nature of career journeys. Denis recounts his experiences navigating the challenges of establishing a successful nightclub in a gentrifying neighborhood, offering insights into the importance of risk-taking and seizing opportunities. The conversation further delves into the lessons learned from both industries, emphasizing the value of people skills and the necessity of adaptability in the face of uncertainty. As the episode unfolds, listeners are invited to reconsider their definitions of success and the paths they choose, ultimately reinforcing the idea that both personal and professional growth often emerge from embracing chaos and uncertainty.

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Takeaways:

1. In the podcast episode, Dennis Keane discusses the necessity of adaptability in business, emphasizing that the ability to pivot is crucial for success in rapidly changing environments.
2. A significant theme addressed in the interview is the importance of understanding financial metrics, which is essential for running any business effectively, including restaurants and startups.
3. Dennis highlights that personal connections and people skills are indispensable, as they enhance communication and foster a productive workplace culture in both the restaurant and tech industries.
4. The conversation reveals that fear of failure often inhibits individuals from pursuing their passions, and Dennis advocates for embracing risk as an integral part of the entrepreneurial journey.
5. Dennis's journey illustrates how experiences in the restaurant industry can provide transferable skills that are extremely beneficial in the tech startup world, particularly in managing teams and understanding customer dynamics.
6. The episode also touches upon the evolving role of AI in business, suggesting that those who adapt and learn to leverage technology will thrive, while those who resist will likely fall behind.

About Denis Keane:

Denis Keane is an entrepreneur and investor who has founded multiple businesses, backed early-stage startups, and advised companies on growth and business development. Most recently, he served as COO and investor in an AI startup that successfully exited through acquisition. Denis now works with founders and leadership teams to help scale operations and unlock new growth opportunities.

Two weeks before the Chicago Marathon, Maricella was terrified. Not just about the race—about what it would mean if she finished and felt destroyed, ashamed of her pace, not wanting to run again.

In this deeply personal episode, she shares what it's like to show up to something hard while feeling like a fraud. She reads her raw journal entries about training anxiety, works through shame about being "too slow," and tells the story of race day—including the sign that changed everything.

This isn't a story about hitting a time goal (she didn't). It's about discovering you're stronger than you thought. About the tools and reminders we need when we forget we're capable. About hope, shame, and doing hard things scared.

Maricella shares a tattoo on her leg that says "Braver, Stronger, Smarter"—from Winnie the Pooh, gotten after the hardest moments of her life. She talks about the bracelets she wore during the race, her partner who believed in her when she didn't believe in herself, and what it means to find your strength not in the outcome, but in showing up.

This is the final episode of 2025.

In this episode:

- Pre-race anxiety and the bonking pattern during training

- Working through shame about pace and performance

- Reading unfiltered journal entries from two weeks before the race

- The difference between facts and fears

- Hope as fuel vs. tying self-worth to outcomes

- Race day: the sign, the nausea, the finish

- Feeling strong instead of destroyed

- The anchors we carry (bracelets, tattoos, people)

- Feeling like a fraud even after accomplishing hard things

- Using tools (therapy, journaling, friends, AI) to see clearly

- Showing up scared and doing it anyway

Mentioned in this episode:

Win the Inside Game by Steve Magness

SAFE methodology (created by guest Jaqueline Oliveira-Cella)