The Grey Areas Podcast with Kelsey Donlon

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The Grey Areas Podcast with Kelsey Donlon

Kelsey Donlon

34 episodes

3 months ago

Welcome back to The Grey Areas Podcast! Today’s guest is Danielle Stead-Blanton, attorney, business strategist, and founder of DSB, a modern legal and consulting firm for creatives, wellness professionals, and female founders. Danielle’s no-fluff approach helps entrepreneurs build protected, scalable businesses without the intimidation of traditional law firms. In this episode, Danielle shares how she left Big Law burnout behind to create a business rooted in strategy and structure. We dive ...

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Society & Culture,

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Welcome back to The Grey Areas Podcast! Today’s guest is Danielle Stead-Blanton, attorney, business strategist, and founder of DSB, a modern legal and consulting firm for creatives, wellness professionals, and female founders. Danielle’s no-fluff approach helps entrepreneurs build protected, scalable businesses without the intimidation of traditional law firms. In this episode, Danielle shares how she left Big Law burnout behind to create a business rooted in strategy and structure. We dive ...

Show more...

Society & Culture,

Episodes (20/34)

The Grey Areas Podcast with Kelsey Donlon

The Legal Wake-Up Call Every Founder Needs: Danielle Stead Blanton on Protecting What You’re Building

Welcome back to The Grey Areas Podcast! Today’s guest is Danielle Stead-Blanton, attorney, business strategist, and founder of DSB, a modern legal and consulting firm for creatives, wellness professionals, and female founders. Danielle’s no-fluff approach helps entrepreneurs build protected, scalable businesses without the intimidation of traditional law firms. In this episode, Danielle shares how she left Big Law burnout behind to create a business rooted in strategy and structure. We dive ...

4 months ago

58 minutes

The Grey Areas Podcast with Kelsey Donlon

Inside Active Burnout Recovery with Ex-Corporate Lawyer Kay Costa

Welcome back to The Grey Areas Podcast! In this powerful episode, I’m joined by Kay Costa, former attorney, first-gen professional, and the creator behind In Lieu of Laundry, where she documents her real-time recovery from corporate burnout. After five years of practicing law and realizing her career was no longer aligned with her values or well-being, Kay made the courageous decision to step away and start fresh. Kay opens up about the emotional and physical toll of her legal career, how bu...

4 months ago

53 minutes

The Grey Areas Podcast with Kelsey Donlon

Colin Rocker Gets Real: The Career Creator You Wish You Had at 22

Welcome back to The Grey Areas Podcast! This week, I’m joined by Colin Rocker, executive coach, keynote speaker, and the founder of For The First, a vibrant community built to support ambitious, first-generation professionals. Colin’s journey from corporate consulting to creating a multi-platform brand is filled with intentional pivots, candid lessons, and powerful insights for anyone rethinking the traditional path to success. In this episode, Colin breaks down what it truly means to design...

4 months ago

51 minutes

The Grey Areas Podcast with Kelsey Donlon

How To Move Forward Confidently After a Layoff with Top Agency Executive Recruiter Meghan Houle

Welcome back to The Grey Areas Podcast! This week I’m joined by Meghan Houle, executive recruiter, career coach, and talent strategist with over two decades of experience helping professionals navigate job loss, career pivots, and bold new beginnings. In this episode, Meghan shares her powerful roadmap for bouncing back after a layoff with clarity and confidence. We talk mindset, strategy, and how to cut through the noise to find roles that actually align with your values. Highlights Include:...

5 months ago

51 minutes

The Grey Areas Podcast with Kelsey Donlon

Navigating Leadership Grey Areas with Lia Garvin: How to Turn Struggling Managers into Effective Team Leaders

Welcome back to The Grey Areas Podcast! This week, I’m joined by Lia Garvin, team operations expert, TEDx speaker, and bestselling author of The New Manager Playbook. With leadership experience at Google, Microsoft, Apple, and Bank of America, Lia has seen it all when it comes to management pitfalls and she’s here to make the hardest parts of leadership feel a whole lot easier. In this conversation, we dive deep into the emotional toll of leadership, the power of trust, and the practical min...

5 months ago

50 minutes

The Grey Areas Podcast with Kelsey Donlon

The Language of Leadership: Bridging the Gap Between What Leaders Say & Employees Hear with Alejandra Ramirez Wells

Welcome back to The Grey Areas Podcast! This week, I'm joined by Alejandra Ramirez Wells, internal communication strategist, facilitator, and founder of Ready Cultures. With over two decades of experience, including 15 years in Big Laws, Alejandra helps companies close the gap between what leaders say and what employees actually hear. In this episode, Alejandra breaks down her “Head, Heart, Hands” framework and shares how clear, empathetic communication can transform culture from the inside ...

5 months ago

49 minutes

The Grey Areas Podcast with Kelsey Donlon

How to Stay Sane When Work Isn’t: Dr. Morray on Navigating Dysfunction, Stress, and Difficult People

Welcome back to The Grey Areas Podcast! This week, we’re joined by Dr. Elisabeth Morray, a licensed psychologist and the VP of Clinical at Alma, a platform supporting nearly 24,000 private practice clinicians nationwide. With expertise in evidence-based therapies like Acceptance and Commitment Therapy (ACT), Dr. Morray is dedicated to bridging mental health expertise with real-world application. In this episode, we explore what it takes to thrive in high-stress workplaces, strengthen emotion...

5 months ago

55 minutes

The Grey Areas Podcast with Kelsey Donlon

The Power of Mattering: How Leaders Can Create a Culture of Significance with Zach Mercurio

Welcome back to The Grey Areas Podcast! This week, we’re joined by Zach Mercurio, a researcher, speaker and author of The Invisible Leader and The Power of Mattering. Through his work with global brands like the US Army, Delta Airlines, and the National Park Service, Zach shares how purposeful leadership creates cultures where people truly feel seen, valued, and essential. In this episode, we dive deep into how leaders can build trust, repair broken relationships, and activate purpose at eve...

5 months ago

56 minutes

The Grey Areas Podcast with Kelsey Donlon

From Invisible to Influential: How Sophie Hirst, Workbaby CEO, Is Rewriting Early Career Rules

Welcome back to The Grey Areas Podcast! This week, we’re joined by Sophie Hirst, career coach, viral TikTok creator, and founder of Workbaby. From magician’s assistant to Google exec, Sophie has done it all, and now she’s helping Gen Z navigate work with clarity, confidence, and influence. In this episode, we dig into how to communicate like a leader, build credibility before the title, and manage up without the cringe. Sophie shares powerful mindset shifts, practical templates, and the caree...

6 months ago

1 hour 7 minutes

The Grey Areas Podcast with Kelsey Donlon

What Are You Worth? Breaking the Silence on Pay Transparency with Hannah Williams

Welcome back to The Grey Areas Podcast! If you've ever been told it's “rude” to talk about money, or worried that asking about salary might tank your chances, this episode is your reminder that transparency is a tool for equity, not conflict. We're joined by Hannah Williams, creator of the viral movement Salary Transparency Street. What began as one bold video with a borrowed mic has become a national platform redefining how we talk about work, worth, and wages. Hannah shares her origin stor...

6 months ago

1 hour 6 minutes

The Grey Areas Podcast with Kelsey Donlon

The Grey Areas of Parental Leave: Allison Whalen on Navigating Career Uncertainty Before, During & After Leave

Welcome back to The Grey Areas Podcast! This week, we’re diving deep into the often-overlooked transition back to work after parental leave—and what employers are missing when it comes to retention, career progression, and leadership accountability. We’re joined by Allison Whalen, co-founder and CEO of Parently, a platform reshaping how companies support employees during leave. Allison shares her raw and empowering journey through infertility, parental leave at a high-growth startup, and the ...

6 months ago

55 minutes

The Grey Areas Podcast with Kelsey Donlon

Jillian Richardson on Making LinkedIn Weird: Thought Leadership Without the Cringe

Welcome back to The Grey Areas Podcast! If you’ve ever felt like you have nothing to say on Linkedin or worse, that you’ll get fired for saying the wrong thing, this episode is your permission slip to show up anyway (and make it weird). We’re joined by the endlessly brilliant and hilarious Jillian Richardson, a ghostwriter, writing coach, and the mind behind the viral “Make LinkedIn Weird” movement. Jillian breaks down how to turn your thoughts into compelling content, why ghostwriting is bas...

6 months ago

50 minutes

The Grey Areas Podcast with Kelsey Donlon

B2B Marketing is Mid: Creative Hot Takes & Insights with Bridget Poetker

Welcome back to the Grey Areas podcast! Today’s episode is all about building a creative career that actually feels good, and what it takes to run a values-first business in a world obsessed with hustle. Our guest is Bridget Poetker, a brand strategist, copywriter, and the co-founder of Creative Little Planet, a content collective helping brands find their voice and cut the fluff. With over a decade of experience across agency life, startups, and solopreneurship, Bridget shares what it really...

7 months ago

51 minutes

The Grey Areas Podcast with Kelsey Donlon

Leadership Without the Politics: Ashley Rudolph on Confidence, Influence & Emotional Intelligence

Welcome back to the Grey Areas podcast! Today’s episode is all about navigating the messy middle, that murky space where leadership, influence, and emotional intelligence collide. Our guest is Ashley Rudolph, an executive coach, former tech VP, and the founder of a leadership coaching practice that empowers high achievers to rise fast without losing themselves along the way. In this episode, we unpack how to build influence before you have the title, what it really means to lead with emotiona...

7 months ago

58 minutes

The Grey Areas Podcast with Kelsey Donlon

Bridging Generations: Navigating Gen Z, the Creator Economy, and Community Building with Lauren Vilips

Welcome back to the Gray Areas podcast! Today, we’re diving into the intersection of brand building, creator partnerships, and how Gen Z is reshaping the future of marketing. Our guest is Lauren Vilips, a powerhouse community builder and strategist who knows exactly how to connect brands and creators in meaningful, scalable ways. As the creator acquisition strategist at Mavely, Lauren leads recruitment programs and partnerships that keep creators engaged, invested, and thriving. Before that...

7 months ago

35 minutes

The Grey Areas Podcast with Kelsey Donlon

Managing Up: How to Get What You Need from the People in Charge with Melody Wilding

Welcome back to the Grey Areas podcast! This week, we’re joined by Melody Wilding, a human behaviour professor, award-winning executive career coach, and the author of Managing Up: How to Get What You Need from the People in Charge. Recognized as one of Insider’s most innovative career coaches, Melody blends psychology, neuroscience, and professional development to empower leaders to build trust, influence, and authority at work. In this episode, we dive into practical strategies for managing...

7 months ago

45 minutes

The Grey Areas Podcast with Kelsey Donlon

Rylie Godoy on Waiting for the Right Position to Open Up

Welcome back to the Gray Areas podcast! If you've ever felt stuck in your career, overlooked for promotions, or like you're doing all the right things but still not getting ahead, this episode is for you. This week, we’re joined by Rylie Godoy, a powerhouse career strategist who helps professionals break free from corporate stagnation and own their worth. After spending 13 years climbing the corporate ladder the hard way, Rylie realized the system wasn’t designed for people like her to succee...

8 months ago

57 minutes

The Grey Areas Podcast with Kelsey Donlon

Navigating The Complexities of Leadership Without Losing Yourself with Connie Gao

Welcome back to the Gray Areas podcast! This week, we’re joined by Connie Gao, a leadership coach dedicated to helping smart, driven, and empathetic leaders unlock their full potential. With a background rooted in research-backed frameworks from Columbia Business School and real-world experience in both startup and corporate environments, Connie brings a structured yet empathetic approach to leadership development. In this episode, we dive into burnout recovery, the gray areas of leadership, ...

8 months ago

56 minutes

The Grey Areas Podcast with Kelsey Donlon

Reclaiming Time: Ashley Chang on Reshaping Careers and Family Life with Sundays

Welcome back to the Grey Areas podcast! This week, we’re joined by Ashley Chang, the inspiring CEO and co-founder of Sundays, a company dedicated to accelerating parents' careers while creating more quality family time. After a decade in product management, Ashley witnessed firsthand how parents, especially moms, are often forced to choose between their careers and their families. With Sundays, she’s on a mission to help parents reclaim their time and thrive both personally and professionally...

8 months ago

33 minutes

The Grey Areas Podcast with Kelsey Donlon

Unpacking HR with DanfromHR: Insights on Careers, Feedback, and Advocacy

Welcome back to the Grey Areas podcast! In this episode, we are joined by Daniel Space, a seasoned HR business partner with experience at major companies like WebMD, Electronic Arts, and Spotify. Daniel is also the creator of the online persona DanfromHR, where he shares valuable career insights and debunks common HR myths through his content on TikTok. With a wealth of experience in both HR and career development, Daniel has become a trusted voice in the job search space, reaching a wide aud...

9 months ago

54 minutes