50. How to Return to Work After a Career Break (With Confidence)

51. The Soft Skills AI Can’t Touch: Career Success & Real Estate with Courtney Pelfrey

How do you pivot careers from higher ed to real estate while managing motherhood and a family business? Courtney Pelfrey (Miller Grant & Company) joins Ashley Billings on the B Student Podcast to reveal the reality of building a relationship-based business in Winter Park, FL. In this episode, we go past the transaction to discuss the emotional side of home buying, the truth about career transitions, and the "secret" soft skill every professional needs: curiosity. Watch the full conversation to learn: * The Pivot: How Courtney moved from 10 years in collegiate career services into the real estate industry. * The "Baby" Metaphor: Why closing on a home is like bringing home a baby and why aftercare matters. * Curiosity vs. AI: Why curiosity is the leadership skill technology can't replicate. * Family Dynamics: The challenges and rewards of running a brokerage with your father and sister. * Working Motherhood: Practical wisdom on staying present as a mom while building a recognizable local brand. * Relationship Business: Why being "purpose-driven" wins over trends every time. Whether you're a relauncher returning to the workforce, a new agent, or a business owner in a new season of life, Courtney’s journey offers a roadmap for staying aligned with your values. If you enjoyed this episode, make sure to subscribe, leave a review, and share it with someone navigating a new season in life or business. Time Stamps: * 00:00 – Meet Courtney Pelfrey & Her Career Pivot Story * 02:12 – Why She Left Higher Education for Real Estate * 04:48 – Building a Family-Owned Real Estate Business * 05:31 – Why Closing on a Home is Like Bringing Home a Baby * 07:15 – Working With Family: Strengths, Roles & Dynamics * 09:42 – Creating a Relationship-Driven Real Estate Brand * 12:18 – The Emotional Side of Buying & Selling Homes * 14:36 – How Career Services Prepared Her for Real Estate * 17:08 – The Reality of Working Motherhood & Flexibility * 19:45 – Balancing Business, Kids & Boundaries at Home * 22:04 – Social Media, Branding & Standing Out in Real Estate * 24:26 – Advice for Young Realtors Starting Their Careers * 26:18 – Why Curiosity Is a Powerful Leadership Skill That AI Can’t Replace * 28:10 – Serving the Winter Park Community & What’s Next for Miller Grant ----------------------------------- Listen to more episodes of The B-Student Podcast wherever you get your podcasts. ----------------------------------- Connect with our Guest: Website: https://millergrantandco.com/ [https://url.avanan.click/v2/r01/___https://millergrantandco.com/___.YXAzOndpbnRlcnBhcms6YTpvOmViODlmMmM4YjYxODg5NTBjNzI1NjA1ZDQ4NzZlMmE1Ojc6YWE4OTo2NmUxODUxMWEyZjliZTUxY2ZiMWI1YjkyZmYzOWFkMDY0M2M2ZTU5OTQyZjBkY2RlNWNkYzhiZDU4YzEzZmUyOmg6VDpO] Instagram:   https://www.instagram.com/courtneympelfrey/ [https://url.avanan.click/v2/r01/___https://www.instagram.com/courtneympelfrey/___.YXAzOndpbnRlcnBhcms6YTpvOmViODlmMmM4YjYxODg5NTBjNzI1NjA1ZDQ4NzZlMmE1Ojc6NzUxMDpjYTI5MTA1ZTczNWU5MTVmMGEzYTFhNTc3YTZjNWIzMmFhNmE0NzY2Nzg3NWNlMTM5MzU0N2VhYzhkMjc3MzQ5Omg6VDpO] LinkedIn:  https://www.linkedin.com/in/courtneympelfrey/ [https://url.avanan.click/v2/r01/___https://www.linkedin.com/in/courtneympelfrey/?isSelfProfile=false___.YXAzOndpbnRlcnBhcms6YTpvOmViODlmMmM4YjYxODg5NTBjNzI1NjA1ZDQ4NzZlMmE1Ojc6NWQ4YTo5OTA1NDRmZWU1OGYxZjAxNTM3MmNjODBlMjBkMjNkMWFkZjEyYWRkYTkyYWM4YjkzZjA2MWMwMjBmNTNmOTBkOmg6VDpO] Learn More about Winter Park Chamber of Commerce: https://www.winterpark.org/ [https://url.avanan.click/v2/r01/___https://www.winterpark.org/___.YXAzOndpbnRlcnBhcms6YTpvOmViODlmMmM4YjYxODg5NTBjNzI1NjA1ZDQ4NzZlMmE1Ojc6OTcxYToxZmU4MjU3OTZjZTg5Njk0MDZjNjk4NTcwNDkwYjQ5MDc0ODY3YjMwZmZiMWIxOGI0YWE4MWRhMDZlZGM5YWQwOmg6VDpO] -------------------------------- Podcast produced by Hi Hello Labs: https://www.hihellolabs.com/ [https://url.avanan.click/v2/r01/___https://www.hihellolabs.com/___.YXAzOndpbnRlcnBhcms6YTpvOmViODlmMmM4YjYxODg5NTBjNzI1NjA1ZDQ4NzZlMmE1Ojc6NmQwMjowZDgxYTkyZWQ3ZGQ3MTc3ZWVmMTJhMjQ0MzExZWE4NWQ2MTNjZjBlOTBmYTQwYWE3NmRkZGVkZGJjNjc0YzI2Omg6VDpO]

50. How to Return to Work After a Career Break (With Confidence)

Thinking about returning to work after a career break — but not sure where to start? In this episode, Ashley Billings interviews Betsy Gardner, CEO of Evermore Advisory and former President & CEO of the Winter Park Chamber of Commerce. After her own 13-year career break, Betsy created the Relaunch program — a proven return-to-work program now helping professional women confidently reenter the workforce across the country. Whether you've been out of the workforce for 2 years or 15, this episode breaks down exactly what it takes to come back — not at the bottom, but at your level. What you'll learn: * How to return to work after a career gap without starting over * Why women struggle with confidence after a career break (and how to rebuild it) * How to update your resume, LinkedIn profile, and personal brand for reentry * The 3 drivers of every career decision: control, content, and compensation * Why forward-thinking employers are actively hiring career returners The leadership and soft skills that make returning women high-value hires This episode is for you if: * You're woman considering returning to work after time off for family, caregiving, or personal reasons * You're mid career-transition and need a confidence reset * You're an HR leader or employer looking to hire experienced returning professionals Timestamps: (00:00) Introduction + Betsy Gardner and the Relaunch program (03:05) The origin of the Relaunch program (06:10) The business case for hiring women returning to the workforce (09:15) Why women leave the workforce and struggle to return (12:20) The confidence gap after a career break (15:10) Betsy's personal career reentry story (18:05) What Relaunch teaches (branding, resumes, LinkedIn) (21:00) The psychology of returning to work after years away (24:05) Control, content, compensation: the 3 Cs of starting a job (27:10) How employers should view resume gaps in 2026 (30:00) The hidden skills career returners bring to the workplace (33:00) Final advice: stop waiting for the "right time" to return to work ----------------------------------- Listen to more episodes of The B-Student Podcast wherever you get your podcasts. If this episode helped you, subscribe, leave a review, and share it with a woman who needs to hear it. ----------------------------------- Connect with our Guest: Website: http://Humanintheroombook.com [https://url.avanan.click/v2/r01/___http://Humanintheroombook.com___.YXAzOndpbnRlcnBhcms6YTpvOjhkNjEzZWUzNzc2ZDljZDA5OTUzY2RhOTFhNjBmYTY0Ojc6OTJmZTozMzc4MmQzMjY0ZGI5MGM1ZWM5MWU2OWU0Yzg3ODczYTA3MzZmODA2MjI4YzkwODlkMmQ2NjQ3MTFhNWZjMzAyOmg6VDpO] Or http://Betsygardner.com [https://url.avanan.click/v2/r01/___http://Betsygardner.com___.YXAzOndpbnRlcnBhcms6YTpvOjhkNjEzZWUzNzc2ZDljZDA5OTUzY2RhOTFhNjBmYTY0Ojc6NzYwMDo5YjU4ZjZiZjM1ZWY3MmE2ZTZjNmM4ZWY3NjBjMjE4OGNkYTY2ODZmNWYyMDM2NzAzMmRmNDNiZjQ3NmYxZmVkOmg6VDpO] Instagram:  https://www.instagram.com/thebetsygardner [https://www.instagram.com/thebetsygardner] YouTube: @humanintheroompodcast Learn More about Winter Park Chamber of Commerce: https://www.winterpark.org/ [https://url.avanan.click/v2/r01/___https://www.winterpark.org/___.YXAzOndpbnRlcnBhcms6YTpvOjhkNjEzZWUzNzc2ZDljZDA5OTUzY2RhOTFhNjBmYTY0Ojc6OWI5NzpmNzAwN2M5MmViMGYxZTNiM2ZkNjcyNWUxMjIzNWUyMGVkYjNiMTg1ODZjNzcwMjZkMjhkY2IwMWRhZDI4MDRkOmg6VDpO] -------------------------------- Podcast produced by Hi Hello Labs: https://www.hihellolabs.com/ [https://url.avanan.click/v2/r01/___https://www.hihellolabs.com/___.YXAzOndpbnRlcnBhcms6YTpvOjhkNjEzZWUzNzc2ZDljZDA5OTUzY2RhOTFhNjBmYTY0Ojc6NmJmOTo4ZWZjNmIwYzBlNGFlNmRmMGMwOGI5MjdjMjQwM2MyYmQ4Y2FiNjczM2FlMzE4MmU1ODcxNDIwYTRjNGU5NDNhOmg6VDpO]

49. Why Creativity and Curiosity Matter in Leadership | Jennifer Deery | B Student

Today on the B-Student Podcast, Ashley Billings interviews Jennifer Deery, Executive Director of the Albin Polasek Museum & Sculpture Gardens, about her journey from corporate banking leadership to nonprofit arts and culture leadership in Winter Park, Florida. Jennifer shares how growing up moving frequently helped shape her adaptability, curiosity, and leadership style. She opens up about earning her Fine Arts degree, working as an art director in the corporate world, and eventually transitioning into museum leadership and nonprofit management. This episode explores: * Career pivots and professional reinvention * Leadership lessons from corporate and nonprofit spaces * Why arts and culture matter to local economies * The impact of museums and cultural institutions * The story and legacy of sculptor Albin Polasek * Creativity, curiosity, and lifelong learning * How art inspires innovation and community connection * Winter Park’s thriving arts and culture scene * Stroke awareness and resilience through creativity * Advice for young creatives and aspiring leaders Jennifer also shares exciting updates about upcoming exhibits, educational programming, collaborations with local organizations, and the museum’s vision for the future as it celebrates 65 years. If you’re passionate about leadership, creativity, entrepreneurship, nonprofit work, museums, community development, or personal growth, this conversation is packed with valuable insight. Time Stamps: 00:00 – Introduction to Jennifer Deery & the Polasek Museum 02:08 – Childhood influences, travel, and discovering museums 04:12 – Jennifer’s first year leading the museum 06:18 – The future vision for the Polasek Museum 08:03 – Transitioning from board member to Executive Director 10:38 – Why arts and culture are economic drivers in Winter Park 13:02 – Collaboration between local museums and cultural organizations 15:02 – Jennifer’s career path from art school to corporate leadership 17:20 – Creativity, psychology, and leadership in business 18:55 – Museum tourism and attracting visitors from around the world 20:02 – Upcoming exhibits, events, and community programming 23:24 – Albin Polasek’s resilience after stroke & advice for creatives Listen to more episodes of The B-Student Podcast wherever you get your podcasts. Like this video, subscribe, and comment your favorite London spot or what city has most transformed you. ----------------------------------- Connect with our Jennifer: Website:  https://polasek.org/ [https://polasek.org/] LinkedIn: @jennifer-deery Instagram:  https://www.instagram.com/polasekmuseum/ [https://www.instagram.com/polasekmuseum/] ----------------------------------- Learn More about Winter Park Chamber of Commerce: https://www.winterpark.org/ [https://www.winterpark.org/] Podcast produced by Hi Hello Labs: https://www.hihellolabs.com/ [https://www.hihellolabs.com/]

48. She Quit Law Twice, Then Invented a Water Scooter | B Student | Lindsay Kiley

Lindsay Kiley did it twice. She stepped away from law to raise her kids, went back to try again as a lawyer, and still something didn't feel right. It wasn't until she invented the Swelly water scooter that she finally built something that felt in alignment. In this episode, host Ashley Billings talks with Lindsay about what those in-between years looked like: the failed ventures, the slow realization that returning to law wasn't the answer, and what it takes to keep going when nothing is working. The overnight success part? It's the smallest part of the story. We get into: * Leaving law, returning to it, and leaving again * The Campable startup experiment and what it taught her * Entrepreneurship while raising kids, the parts nobody posts about * How Swelly went from a garage idea to retail shelves * What she'd tell anyone who feels like they've missed their window If you're mid-pivot, stuck, or rebuilding, Lindsay's been there. More than once. This episode is part of B Student: Summer School, a limited series featuring entrepreneurs and professionals who have gone through Winter Park Chamber of Commerce leadership and talent development programming #swelly #entrepreneurship #womeninbusiness #femalefounder #smallbusiness #productbusiness #careerpivot #careerchange #workingmoms #mompreneur #founderstory #youtubepodcast #spotifypodcast #businesspodcast Time Stamps: 00:00 Introduction + Meet Lindsay Kiley 02:45 Leaving Law + Entering the Unknown 05:30 Trying Again (And Why It Still Didn’t Fit) 08:10 Failed Paths: Campable + In-House Role 10:50 Starting Over Without a Plan 13:30 Building Resilience + Not Giving Up 16:00 Mom Life + Returning to Work 18:45 Entrepreneurship While Raising Kids 21:30 Launching Swelly + First Wins 24:00 Expanding the Brand + New Products 26:30 Overcoming Fear + Stepping Outside Comfort Zone 29:30 Advice for Career Pivots + Final Thoughts ----------------------------------- Listen to more episodes of B Student wherever you get your podcasts. Like this video, subscribe, and leave a comment with the moment you knew it was time to make a change. ----------------------------------- Connect with our Guest: Website: https://swelly.us/ [https://swelly.us/] Instagram:  https://www.instagram.com/swelly.us/ [https://url.avanan.click/v2/r01/___https://www.instagram.com/swelly.us/___.YXAzOndpbnRlcnBhcms6YTpvOjQzZDc0YzlhZmU2YWU4ZjRkZGM3OGY2YWE3MjVjYzJjOjc6NWJiNjpkN2I2NGFjZTNkYjQ3NWFjY2Y0OGFmOTc2ODhlMmNkMzEzNDU1ZTUwY2RhZjViMDVjNmVhYzk3NGVkMDc5YjdmOmg6VDpO] Learn More about Winter Park Chamber of Commerce: https://www.winterpark.org/ [https://url.avanan.click/v2/r01/___https://www.winterpark.org/___.YXAzOndpbnRlcnBhcms6YTpvOjQzZDc0YzlhZmU2YWU4ZjRkZGM3OGY2YWE3MjVjYzJjOjc6MmI5ODpiYTFkNmIzM2U4MjZjNmZmZDA1YmJhMmRlZDQwODg0YmUxOTg5MmI0OTcwMTE1ZDgxNTAyNDQ5ZDE4ZGEyZDJjOmg6VDpO] -------------------------------- Podcast produced by Hi Hello Labs: https://www.hihellolabs.com/ [https://url.avanan.click/v2/r01/___https://www.hihellolabs.com/___.YXAzOndpbnRlcnBhcms6YTpvOjQzZDc0YzlhZmU2YWU4ZjRkZGM3OGY2YWE3MjVjYzJjOjc6MWNmYToxNDE3NTc2YzJhNDM2MWZmMThlMWFjNjI3ZjZlNjRjZWEwNDZhOThkYTk0YmFjNDQ5YzRjY2E5ZDIzZjQzMjRkOmg6VDpO]

47. Graduation Day Betsy’s Final Episode

This is more than a farewell episode… it’s a leadership blueprint for the future of work. In this powerful final episode as host of the B Student Podcast, Betsy Gardner reflects on the biggest lessons learned from interviewing top leaders, entrepreneurs, and changemakers across the globe. From navigating business challenges to building meaningful relationships, this episode dives deep into what truly drives success in today’s world. You’ll learn why relationships matter more than strategy, how vulnerability becomes your greatest leadership advantage, and why soft skills are the most critical asset in the age of AI. This episode also explores: * Why human connection is the missing piece in modern leadership * The growing mentorship gap in today’s workforce * How vulnerability builds trust, influence, and impact * The importance of presence, polish, and personal brand * Lessons from top guests including entrepreneurs, chefs, and industry leaders * What’s next for the B Student Podcast and “B Student Summer School” If you’re a leader, entrepreneur, young professional, or someone navigating growth in your career, this episode will challenge how you think about success and equip you with the mindset needed for what’s ahead. Time Stamps: 0:00 Graduation Day & Final Episode Begins 1:30 Reflecting on the Podcast Journey 3:00 Why Relationships Matter More Than Results 4:30 The Mentorship Gap & Human Skills Crisis 6:00 Vulnerability in Leadership & Personal Growth 7:30 Learning to Show Up Authentically 9:00 The Power of Feedback & Being Coachable 10:30 Lessons from Guests & Real Conversations 12:00 The Future of Work, AI & Soft Skills 13:30 What’s Next: Summer School & New Chapter 15:00 Betsy’s Next Move & Final Thank You ----------------------------------- Listen to more episodes of The B-Student Podcast wherever you get your podcasts. Like this video, subscribe, and comment your favorite London spot or what city has most transformed you. ----------------------------------- Connect with Betsy Gardner: Website: https://www.betsygardner.com/ [https://www.betsygardner.com/]  Learn More about Winter Park Chamber of Commerce: https://www.winterpark.org/ [https://www.winterpark.org/] -------------------------------- Podcast produced by Hi Hello Labs: https://www.hihellolabs.com/ [https://www.hihellolabs.com/]