54. What Hiring Managers Really Think About Your Career Gap

54. What Hiring Managers Really Think About Your Career Gap

If you've taken a break from the workforce, you’ve probably worried about how to explain the empty space on your resume.  But do career gaps actually hurt your chances of getting hired, or could they be the exact thing that makes you stand out? In this episode of B Student: Summer School, Ashley Billings hosts a live panel discussion with Central Florida employers - including The Mayflower at Winter Park, Orlando Health Winnie Palmer Hospital for Women and Babies, Florida Blue, and The Bar Method Winter Park - and hiring leaders to pull back the curtain on modern workforce trends. As artificial intelligence changes how businesses operate, recruiters are looking for the exact human skills that technology can’t replicate, like emotional intelligence, adaptability, and resilience. The panel shares honest feedback on why a career pause to raise children, care for family, or navigate a major life transition doesn't diminish your professional value. In fact, it often builds the exact leadership experience today's companies are looking for. What we discuss in this episode: * The shifting reality of how hiring managers view resume gaps * Why soft skills and emotional intelligence matter more than ever in an AI world * Turning volunteer work and life transitions into professional leadership experience * How to build confidence and own your story when returning to the workforce * Behind the scenes of the Relaunch mock interview experience * Actionable advice for women and younger professionals entering a competitive job market Time Stamps: -00:00 - Why Career Gaps Are More Valuable Than You Think -02:35 - Meet the Employers Behind the Panel -05:12 - What Stands Out in Today's Hiring Process -07:48 - Why Initiative Matters More Than Resumes -10:15 - The Soft Skills Employers Want Most -13:08 - What AI Can’t Replace in the Workplace -15:52 - How Career Pauses Build Leadership Skills -18:40 - Volunteer Work as Professional Experience -21:25 - What Employers Love About Relaunchers -24:10 - The Confidence Advantage of Life Experience -26:58 - Inside the Relaunch Mock Interview Experience -29:12 - Advice for Younger Professionals Entering the Workforce -31:35 - Why Relaunch Changes Lives -33:18 - What Employers Really Think About Career Gaps -34:45 - Final Encouragement for Women Returning to Work ----------------------------------- Listen to more episodes of The B-Student Podcast wherever you get your podcasts. ----------------------------------- Connect with our Guests at: Taylor Womack: https://www.linkedin.com/in/taylor-mckenzie-womack-855b68b5/ [https://www.linkedin.com/in/taylor-mckenzie-womack-855b68b5/] The Mayflower at Winter Park: https://www.linkedin.com/company/the-mayflower-at-winter-park/ [https://www.linkedin.com/company/the-mayflower-at-winter-park/] Joshua Montemayor: https://www.linkedin.com/in/joshua-montemayor-647a7a24a/ [https://www.linkedin.com/in/joshua-montemayor-647a7a24a/] Orlando Health: https://www.linkedin.com/company/orlando-health/ [https://www.linkedin.com/company/orlando-health/] Karl Davis: https://www.linkedin.com/in/karl-davis-b7489b84/ [https://www.linkedin.com/in/karl-davis-b7489b84/] Florida Blue: https://www.linkedin.com/company/florida-blue/ [https://www.linkedin.com/company/florida-blue/] Karen Moreno: https://www.linkedin.com/in/karen-moreno-59317735/ [https://www.linkedin.com/in/karen-moreno-59317735/] The Bar Method Winter Park: https://barmethod.com/locations/orlando-winter-park/ Learn More about Winter Park Chamber of Commerce: https://www.winterpark.org/ [https://url.avanan.click/v2/r01/___https://www.winterpark.org/___.YXAzOndpbnRlcnBhcms6YTpvOjc1N2I2YjkxNjlhMTRkMmQyZDNiYjM2NjAxNjVmOTJlOjc6NTVmNjo3OGI3MTc3NzE1NmUyMzhmYTdjMzFiNDk4Mjk5YzllYWFlMmNiOTM0MGZlOWI4OTQyYWNkNGI5NGNlOTIzNGNlOmg6VDpO] -------------------------------- Podcast produced by Hi Hello Labs: https://www.hihellolabs.com/ [https://url.avanan.click/v2/r01/___https://www.hihellolabs.com/___.YXAzOndpbnRlcnBhcms6YTpvOjc1N2I2YjkxNjlhMTRkMmQyZDNiYjM2NjAxNjVmOTJlOjc6NjE0Nzo5YzkyNTgyNThlYzE1OWNjNzE0ZDhjODJiNTdjOTc0NGMzNDJiOGYzNzFjNmMxMWQzN2Q3MGVjZDhmMmJlYzU2Omg6VDpO]

53. From Launching Old Navy & PINK to Building a Local Coffee Shop | Tracy Liffey | B Student

Tracy Liffey spent years helping launch some of the most iconic retail brands in the world, including Old Navy and PINK by Victoria's Secret, eventually overseeing creative teams of more than 100 people. But despite a highly successful corporate career, she chose to make a major pivot. Today, she is the founder of New General Café, a beloved clean food and coffee brand in Winter Park, Florida. In this episode of the B Student podcast, host Ashley Billings sits down with Tracy to talk about what it takes to leave corporate America and build a business from scratch. Tracy shares an honest look at the identity shift that happens when you leave a major job, the daily realities of entrepreneurship and working motherhood, and how to build a business that values community and connection over quick trends. Throughout this episode, Tracy shares: * The realities of walking away from an executive corporate career * Behind-the-scenes lessons from launching global brands like Old Navy and PINK * Learning a completely new industry from scratch and building New General Cafe * How to listen to your customers and pivot when things get tough (including navigating COVID) * The identity shift that comes with leaving a successful career to start over * Balancing the demands of entrepreneurship with working motherhood * Practical advice for anyone navigating a major career transition or launching a small business Time Stamps: (00:00) Welcome to The B Student Podcast (02:15) How New General became a community hub (05:30) Leaving corporate America to be more present (08:10) The original vision for New General Cafe (11:25) Listening to customers and pivoting fast (14:40) Creating healthier coffee and food options (17:55) Learning the food and beverage business (20:45) Building with community support in Winter Park (23:30) Navigating COVID as a small business (26:45) The reality of entrepreneurship as a working mom (30:10) Lessons from Gap, Old Navy, PINK, and Victoria’s Secret (33:20) Advice for women considering a career pivot ----------------------------------- Listen to more episodes of The B-Student Podcast wherever you get your podcasts. ----------------------------------- Connect with our Guest: LinkedIn:  @tracy-brand-liffey Website: https://www.newgeneral.us/ [https://url.avanan.click/v2/r01/___https://www.newgeneral.us/___.YXAzOndpbnRlcnBhcms6YTpvOjE4MzE1NjFjYmQ1NDM2YjUxZTAyZGJhYzdlOTA5Yjk1Ojc6Y2E1ODpjZjdlNmM0ZTg4MjlhOGU4NDcyNmEzNzJjYTFiM2M0YjQ5MmQ1NTZlZjM0ZGI3ODFmNzdiODEzNGRkNDRiYzZjOmg6VDpO] Learn More about Winter Park Chamber of Commerce: https://www.winterpark.org/ [https://url.avanan.click/v2/r01/___https://www.winterpark.org/___.YXAzOndpbnRlcnBhcms6YTpvOjE4MzE1NjFjYmQ1NDM2YjUxZTAyZGJhYzdlOTA5Yjk1Ojc6ZDcyOTo4ODM4YjAxNTIzM2Y2N2QyZDljOWVlN2EwOTc0ZmZjMDg4YjlkNDc5MDI3MDAxYjk3NTFlMDhjMDA0YmE0Y2I1Omg6VDpO] -------------------------------- Podcast produced by Hi Hello Labs: https://www.hihellolabs.com/ [https://url.avanan.click/v2/r01/___https://www.hihellolabs.com/___.YXAzOndpbnRlcnBhcms6YTpvOjE4MzE1NjFjYmQ1NDM2YjUxZTAyZGJhYzdlOTA5Yjk1Ojc6MTEwZjphMDgxMTExOTk2ZDBlNzJhN2VmNDE3N2NiYjA1MDRkZTIyOTBlMWFjMTUwNmQ5YWRkMTY3YzhhYzcxNDViY2ZiOmg6VDpO]  #BStudentPodcast #WinterParkFL #NewGeneral #WomenInBusiness #CorporatePivot #Entrepreneurship #OldNavy #VictoriasSecretPINK #SmallBusinessOwner #CareerTransition

52. 25 Years at Disney: Leadership Lessons & Career Reinvention with RK Kelley

In this episode of the B Student podcast, RK Kelley shares her incredible career journey from spending more than 25 years in leadership roles at Disney to becoming a driving force behind the Central Florida Pledge, a community initiative dedicated to fostering dignity, respect, and civil discourse across Central Florida. RK discusses career transitions, purpose-driven leadership, mentorship, women in leadership, community engagement, Disney leadership lessons, workplace culture, and the challenges facing organizations in today's divided environment. Throughout the conversation, RK discusses: * Disney Leadership Lessons: What 25+ years in global operations taught RK about workplace culture and respect. * Career Reinvention: Navigating the shift from a high-intensity executive role to a purpose-driven "second act." * The Central Florida Pledge: Why dignity and civil discourse are the most critical tools for today’s community leaders. * Redefining Success: How to prioritize family and values while maintaining professional impact. RK also shares how stepping away from a demanding executive career allowed her to redefine success, prioritize family, and embrace a purpose-driven chapter focused on creating lasting impact. If you're exploring a career change, leadership growth, personal development, women in business, nonprofit leadership, or community impact, this episode is full of actionable insights and inspiration. Time Stamps: 00:00 Welcome to the Podcast 02:01 What Is the Central Florida Pledge? 04:26 Why RK Kelley Chose a Purpose-Driven Career 06:45 How Businesses Can Get Involved 09:12 Creating Respectful Dialogue Across Differences 11:35 The Biggest Challenge Facing Communities Today 13:57 A Vision for Central Florida's Future 16:20 Why Listening Is a Critical Leadership Skill 17:42 Lessons Learned from 25+ Years at Disney 20:35 The Relaunch Program and Career Reinvention 24:15 Mentorship, Self-Doubt, and Growth 28:08 Redefining Success Through Purpose and Family ----------------------------------- Listen to more episodes of The B-Student Podcast wherever you get your podcasts. ----------------------------------- Connect with our Guest: LinkedIn:  https://www.linkedin.com/in/rk-little-kelley [https://url.avanan.click/v2/r01/___https://www.linkedin.com/in/rk-little-kelley___.YXAzOndpbnRlcnBhcms6YTpvOmViZDMzMDdmYTA3MjUwZWY2NTJjZWE5N2Y2YjAyMjBjOjc6ZmExMjozZWVkM2Q3ZWVjYTBiZDRmMGEzNGRkMzYyYmQ0NTI5OTFiNDQ2ZWY3ZTY0NDM3NGJmNjkzYTIyYjU0MGJiZmIyOmg6VDpO] Learn More about Winter Park Chamber of Commerce:  https://www.winterpark.org/ [https://url.avanan.click/v2/r01/___https://www.winterpark.org/___.YXAzOndpbnRlcnBhcms6YTpvOmViZDMzMDdmYTA3MjUwZWY2NTJjZWE5N2Y2YjAyMjBjOjc6M2FmNzpmMjg3YTIzZTIxYjRkMTc4OTVlNzkwZWNhNTMxY2QzOGExMDBlNWMyZTA4MjU3ZGIzNGJlMWI0YjZlNDA4MmM0Omg6VDpO] -------------------------------- Podcast produced by Hi Hello Labs: https://www.hihellolabs.com/ [https://url.avanan.click/v2/r01/___https://www.hihellolabs.com/___.YXAzOndpbnRlcnBhcms6YTpvOmViZDMzMDdmYTA3MjUwZWY2NTJjZWE5N2Y2YjAyMjBjOjc6ODc1ODpkNjcyNzJiOGRlYzhhNzBiNjM4YmZhN2JmMDYzMDQ5MWI3OWU3NTZlZjJjOGJmY2U0MTFjNjQyM2M3ODQ1ODc1Omg6VDpO]

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]