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In this episode of Time to Press Pause, host Ellen Williams welcomes two guests: executive coach and Morningstar Ventures CEO Andrea Chilcone, and philanthropic advisor Stephanie Borsari. Andrea explains three common reasons professionals “press pause” in their careers: being involuntarily forced into change (such as restructuring), retiring without clarity on the next chapter, or experiencing a slow values or lifestyle clash. Stephanie falls into the last category; though she had a successful career in executive management, she discovered her role was unfulfilling and misaligned with her deeper values. With Andrea’s guidance, Stephanie decided to leave her position and step back to rediscover what mattered most.

During her professional sabbatical, Stephanie tried out various creative pursuits—writing poetry, considering new hobbies, and reevaluating her work identity. Eventually, she discovered she wanted to return to philanthropy on her own terms, establishing an independent consulting practice that allows her to focus on connecting private foundations and donors to meaningful causes. Andrea notes that not everyone must become a business owner; what’s important is to discover the path that authentically aligns with one’s strengths and values.

Both Andrea and Stephanie emphasize the privilege of taking a reflective pause, underlining the honesty and integrity needed to answer difficult questions about one’s true calling. Modern leadership, Andrea adds, acknowledges no individual can have all the answers. Stephanie now embraces vulnerability and emotional connection as key to her identity, and they both advise leaders to press pause the moment they discover they are no longer their best selves or are working for the wrong reasons.

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In this episode of Time to Press Pause, host Ellen Williams speaks with Henry Poydar, founder and CEO of Steady, a predictive coordination platform that grew out of his earlier venture, Status Hero. Henry describes two pivotal moments when he paused to reconsider his next steps. After co-founding Bantam CRM and joining Constant Contact post-acquisition, he spent three years working on a major systems integration project—a process he likens to open-heart surgery. Longing to return to hands-on product development, he created Status Hero, a tool that addressed the challenges of large teams trying to stay aligned asynchronously. Eventually, he built Status Hero to a seven-figure ARR before realizing he needed additional capital to scale beyond his solo efforts. Choosing investors who shared his commitment to sustainable growth allowed him to assemble an elite distributed team and rebrand as Steady, expanding the product’s capacity to serve entire organizations.

Throughout the conversation, Henry highlights how his technical background fueled fast, iterative development and let him adapt Status Hero to user feedback almost instantly. He also underscores the value of maintaining strong networks, crediting connections from Constant Contact and elsewhere with helping him raise the kind of funding that aligns with his vision. Finally, he emphasizes the importance of transparent communication and context-sharing so that everyone on a team understands the “why” behind decisions. According to Henry, leaders should be deliberate about taking time to reflect, ensure the entire organization remains curious and informed, and continuously reinforce the mission and values that guide the work.

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In this special New Year’s episode of Time to Press Pause, host Ellen Williams compiles lessons from several Season 1 guests to help leaders make 2025 a purposeful and growth-oriented year. Each guest highlights a key insight for personal and professional development:

• Stay Open to Possibilities
  DC Glenn, half of hip-hop duo Tag Team and CEO of CLG Investments Inc., discusses the importance of setting aside ego and embracing every opportunity as it arises. He compares past experiences to a “language model” that informs future decisions, emphasizing continual learning and evolution.
• Lead Authentically on Social Media
  Jaci Clement, CEO of Fair Media Council, underscores the need for leaders to be visible online. She recommends sharing enough personal insights to humanize yourself without overexposure, reinforcing that people want to see the real face behind the brand.
• Accept Life’s Uncertainty
  Alan Furlong, CEO of The Growth Doctors, recalls a life-altering injury at 16 to illustrate how quickly circumstances can change. He reminds leaders that there’s never a full guarantee of certainty, and that sitting with “unknowing” often reveals new opportunities that align more closely with market needs.
• Root Decisions in Core Values
  Barbara Fonti, founder of The Fonti Group and chief business coach at Big Dream Executive Coaching, emphasizes creating a personal “root document” of non-negotiable values. By aligning decisions with these core values, leaders can bring authenticity and consistency to every role they play.
• Plan Your Pause
  Dr. Marie-Helene Pelletier, leadership psychologist and author of The Resilience Plan, stresses the importance of scheduling pauses just as strategically as you schedule other organizational activities. Building “pause time” into your routines safeguards resilience and mental well-being.
• Pause for Collective Good
  Carol Silva Moralez, CEO of Upskill NWA, advocates not only for personal pauses but also for team-wide reflection. By giving everyone thinking space and involving them in critical decisions, organizations foster a culture of collaboration, well-being, and continuous improvement.

These insights form a powerful blueprint for stepping into 2025. Ellen invites listeners to begin the new year by pressing pause more deliberately—allowing space to focus on what truly matters, stay open to possibility, and stay grounded in personal values. Season 2 of Time to Press Pause promises more real-life C-Suite stories, offering further inspiration for leaders ready to thrive in the year ahead.