In this episode of Lonely at the Top, Rachel sits down with Emma Whittard, a former senior executive in global children’s publishing turned transformational coach for women leaders in midlife.

Emma shares what it was really like to rise through the ranks at companies like Disney, DreamWorks, and Warner Brothers, including the invisible loneliness of being the only person in the room who knew how to build something entirely new. From running international publishing businesses to launching a startup-within-a-studio at DreamWorks, Emma reflects on the emotional cost of responsibility, especially when success quickly turned into loss and layoffs.

Together, Rachel and Emma explore the isolating reality of leadership decisions that affect livelihoods, the lack of mentorship for innovators inside large organizations, and how women in particular are conditioned to carry enormous pressure quietly. Emma also speaks candidly about midlife transitions—shedding inherited stories of worth, productivity, and self-sacrifice—and why the best leaders are those who stay curious, ask great questions, and allow themselves to remain human.

Episode Highlights

• “I was the only person in the entire company who had ever done this before.”
  Emma describes the profound loneliness of building a new business inside DreamWorks with no roadmap and no peers.
• Creating a global business plan while sitting on her bed with a toddler nearby
  A striking image of how leadership, motherhood, and pressure collided in real time.
• The moment everything changed from expansion to contraction
  Being asked to dismantle the very team she had just built—and how close that brought her to burnout.
• “That’s the closest I’ve ever come to a breakdown.”
  Emma’s most vulnerable admission about the emotional toll of leadership without support.
• The spa certificate that saved her nervous system
  A small but profound example of how self-care—not strategy—was what she actually needed.
• “Leaders who ask great questions are the best leaders.”
  Emma reframes leadership as humility, curiosity, and connection rather than certainty.
• What she would do differently now
  Naming mentorship and embodied support as non-negotiables for anyone at the top.

Connect with Emma:

• EmmaWhittard.com

In this episode of Lonely at the Top, Rachel sits down with Sorby Grant, President and CEO of Climb Hire, an equity-focused workforce development nonprofit supporting underemployed adults in accessing real economic mobility.

Sorby reflects on the emotional cost of being the decision-maker, the pressure of stewarding a mission rooted in justice and opportunity, and the quiet exhaustion that can make it hard to recognize success while you’re living it.

A central thread of the conversation is social capital — how access to relationships, trust, and informal networks determines who gets opportunities and who stays stuck. Sorby unpacks why talent alone is rarely enough, how the “hidden job market” really works, and why teaching people how to build professional relationships is a critical equity intervention.

She also opens up about her own leadership evolution: stepping into the CEO role after working closely inside the organization, navigating the shadow of a founder with a very different leadership style, and learning to claim her own authority without losing the heart of the mission.

Connect with Sorby:

• https://climbhire.co/
• Sorby@climbhire.co

In this episode, Michelle Markwart Deveaux—author, singer, facilitator, coach, and founder of multiple mission-driven businesses— shares her journey from theology and the arts into business ownership, and the often unseen emotional labor of building something meaningful in systems that weren’t designed to sustain creatives. She speaks candidly about self-doubt at high levels of leadership, the difference between being nice and being clear, and why direct communication, while necessary, can deepen isolation at the top.

Together, Rachel and Michelle unpack how leaders learn to keep moving forward even while privately questioning their worth, impact, or belonging. Michelle reflects on her desire to be impactful rather than “important,” and why self-examination is not indulgent but essential for ethical, sustainable leadership.

Episode Highlights

• A candid exploration of how self-doubt often increases—not decreases—at higher levels of leadership, especially for women and femme founders.
• Michelle unpacks the difference between being nice and being kind, and why leaders eventually have to choose clarity over likability.
• A nuanced conversation about how direct communication creates effectiveness while simultaneously increasing isolation at the top.
• Insight into how many creatives and consultants unintentionally undervalue their work due to inherited narratives about money, art, and service.
• A powerful reframing of leadership success: impact over importance, and why visibility without integrity leads to burnout.
• Discussion of how leaders often miss or minimize opportunities because they’ve learned to downplay their own significance, particularly in female-socialized leaders.
• An honest look at how leadership requires holding consent, agency, and boundaries in environments that reward over-giving.

Connect with Michelle

• https://thespeakeasycooperative.com/
• https://www.instagram.com/thespeakeasycooperative/
• https://www.linkedin.com/in/michelle-markwart-deveaux/
• Michelle@faithculturekiss.com