Breaking Barriers In Property Management

In this honest conversation, Karry Canfield shares her journey from surviving domestic violence and homelessness to rebuilding her life and career with support from Entryway. She talks with Sheila Greene about finding housing, mentorship, career training, and community through Entryway’s Leasing 101 program.

Now Karry gives back by volunteering and teaching leasing classes, helping others see new possibilities for themselves.

Content note: This episode discusses domestic violence, a violent assault, and homelessness.

Learn more about Entryway: https://entrywaytalent.org
Watch the episode on YouTube: https://youtu.be/jJaxXvfrEiU

What happens when the host becomes the guest? In this special reverse-host episode, Takara Fuller Doby flips the mic and interviews Breaking Barriers creator Sheila Greene about the real story behind the show—and behind her career.

Takara and Sheila unpack what motivated Sheila to start Breaking Barriers: decades of being overlooked in property management leadership, a mentor who taught her to focus on one thing at a time, and a mentorship program that unexpectedly changed lives. Sheila opens up about the “what if” fears that almost stopped her, the confidence gap that holds women back, and how speaking her goals into existence helped her rise from property manager to VP of Operations to CEO.

The conversation also explores community, Runway of Strength and support for domestic violence survivors, the power of networking, and the importance of rest, boundaries, and letting go of guilt. Their challenge to every woman listening: name the barrier you’ve broken, then help someone else break hers.

IN THIS EPISODE:

• Focus on one thing at a time to build momentum

• Confidence and self-advocacy matter as much as competence

• Growth begins when you push past the “what if”

• Mentorship is a two-way gift

• Rest and boundaries make you more effective

• You are allowed to take up space

ABOUT THIS EPISODE:

Takara Fuller Doby, a host with Christian Television Network, steps in as host and interviewer. Sheila Greene, founder of Breaking Barriers, takes the guest seat to share her story.

CHAPTERS:

00:00 Welcome: Sheila Becomes the Guest

01:02 The Motivation Behind Breaking Barriers

05:00 Mentorship & the Power of “Me Time”

07:34 Pushing Past the “What If”

09:46 Runway of Strength & Giving Back

13:37 You Need a Village—and Why “Breaking Barriers”

17:54 Speak It Into Existence

19:56 Networking & the Little Black Book

29:51 Rest, Recovery & the Sabbath

34:17 Stop Apologizing, Own Your Worth

37:21 Empowering Others to Lead

40:21 Final Challenge & Sign-Off

If this conversation encouraged you, follow Breaking Barriers with Sheila for more honest conversations about leadership, faith, mentorship, and empowering women to break through their own barriers.

#BreakingBarriers #WomenInLeadership #Mentorship #Confidence #PropertyManagement #FaithAndLeadership #WomenEmpowerment #CareerGrowth

Have you ever been winning at work — and still almost walked away?

In Episode 7, Sheila Greene gets personal. She shares the story of leading one of the biggest turnarounds of her career — taking a property from 150 vacant units down to 10 in just four months — only to find herself handing in her two weeks notice because of the leadership environment around her.

What happened next changed everything.

The owner drove three hours unannounced just to ask her to stay. And the question he asked her during that walk is one she still carries with her today as a CEO and leader in affordable housing.

This episode is for every leader who is doing great work and wondering if it's even worth it.

TIMESTAMPS

00:00 – Introduction00:43 – Welcome to Breaking Barriers01:43 – Managing a distressed property02:43 – A difficult leadership environment03:14 – The moment everything changed04:15 – Three lessons that stuck forever06:33 – Final thought on what leadership really means

LISTEN AND FOLLOWApple Podcasts — https://podcasts.apple.com/us/podcast/breaking-barriers-in-property-management/id1858163436Facebook — https://www.facebook.com/profile.php?id=61574188828407

Youtube: https://www.youtube.com/@BreakBarrierspodcastSubstack — https://breakingbarrierswithsheila.substack.comAll Links — https://linktr.ee/breakbarrierspodcast

In this episode of Breaking Barriers in Property Management, I sat down with Jessica Dimas, Director of Operations at Rainey Property Management, for a conversation that was personal, honest, and deeply real.We talked about motherhood, career growth, caregiving, burnout, taking risks, and what it means to keep showing up when people don’t see everything you’re carrying.Jessica’s story is a reminder that sometimes the right role doesn’t exist until the right leader builds it. And sometimes, one decision can change the direction of someone’s life and career.Strong women aren’t strong because life is easy. They’re strong because they carry the hard things and keep moving forward anyway.00:00 – Welcome + why this conversation is personal00:30 – Introducing Jessica Dimas + her leadership journey01:40 – Shared life experiences: motherhood, caregiving, and pressure03:40 – What balancing leadership, motherhood, and life really looks like04:40 – The truth about overwhelm as a high-performing woman05:10 – When work starts impacting family life06:00 – The cost of ambition: missed moments and hard lessons07:10 – Guilt, burnout, and the pressure to always say yes08:00 – Feeling like you have to choose between career and family10:00 – Facing a breaking point: pregnancy, travel, and uncertainty11:00 – Considering walking away from it all12:00 – The moment everything changed: redefining the role13:30 – Why women shouldn’t be penalized for motherhood16:30 – Building a role that didn’t exist before18:00 – Creating support systems to prevent burnout19:30 – Stepping into leadership and owning your worth21:30 – Growth happens outside your comfort zone23:00 – Building a department from the ground up24:30 – Finding your “why” on the hard days25:20 – The shift from surviving to leading26:30 – Advice for women feeling stretched too thin27:30 – The importance of self-care and small moments29:00 – Leadership, resilience, and unseen strength32:00 – The power of one decision to change your career35:00 – Taking risks and betting on yourself37:00 – Building teams that last and creating real impact38:00 – Closing thoughts🔗 Follow & ConnectFacebook: https://www.facebook.com/Breakingbarriersinpropertymanagement/LinkedIn (Podcast): https://www.linkedin.com/company/breakingbarriersinpropertymanagementLinkedIn (Sheila Greene): www.linkedin.com/in/sheila-greene-tx

In today’s episode, I interviewed Takara Fuller Doby, a powerful woman with a powerful story of overcoming and breaking barriers. I also want to take a moment to highlight an amazing event that is making a real impact: Runway of Strength: Fashion for a Cause.

Join us this Saturday, April 18 at 3PM at New Hope Church, 121 N. Knights Ave., Brandon, FL — they are almost SOLD OUT!!

This is more than a fashion show. There will be amazing vendors, raffles, and powerful entertainment all coming together for a purpose.This event is all about bringing awareness, uplifting survivors, and empowering women to walk boldly and fearlessly.

https://www.eventbrite.com/.../runway-of-strength-fashion...

If you’re unable to attend but still want to support this incredible cause, you can donate here: Support + Donate: https://runwayofstrength.org

Every contribution helps bring awareness, support survivors, and make a real impact. Even sharing this goes a long way.

There is a common misconception in our industry that Regional Managers need to be superheroes who can fix every problem just by showing up. However, the real solution isn't found in a single person’s strength—it’s found in the systems they build.On this episode of Breaking Barriers in Property Management, I sit down with our Regional Vice President over California, Cesar Carranza, to talk all about it.

We debunk the myths surrounding the regional role and dive into what it actually takes to succeed. I talk about how the key to thriving isn't just working harder, but mastering prioritization, delegation, and consistent systems.

Cesar and I also discuss:Why financial education is a powerful tool for developing regionals into strategic leaders.

How to support on-site staff by building their confidence through clear guidelines and structure.Why some regionals thrive while others face burnout, and how to create a path toward long-term success.

If you are ready to move past the "magic" and start building a more resilient portfolio, give this episode a listen.

Social Media Links:

https://linktr.ee/breakbarrierspodcast

In this episode, you’ll learn how to build leadership confidence that lasts.

If you’re in a leadership or management role and you’ve ever second-guessed yourself, overthought decisions, or felt imposter syndrome creep in, you’re not alone. The difference is learning what confidence really is and how to strengthen it on purpose.

In this episode, you’ll get practical tools you can start using right away, including:

• What confidence actually is and what it is not

• Habits that build confidence over time

• How to quiet the inner critic and lead with clarity

• Breaking down imposter syndrome and the thought patterns behind it

• Showing up consistently even when you don’t feel “ready”

• Simple shifts that strengthen your leadership presence

If you want to lead with more clarity, steadiness, and trust in yourself, press play.

In this episode, you’ll learn how to handle difficult conversations like a pro.

If you’re in a leadership or management role, these conversations are unavoidable. The difference is how you approach them and what results you get on the other side.

In this episode, you’ll get practical tools you can apply right away, including:

• How to navigate tough conversations with clarity and structure

• Active listening that keeps the conversation productive

• Staying professional when emotions rise

• Setting expectations so next steps are clear

• Delivering feedback without creating defensiveness

• Addressing issues early before they escalate

If you want stronger communication, higher accountability, and fewer repeat problems, press play.

Join Sheila Greene, CEO, mentor, and industry leader in property management, as she shares lessons that shaped her leadership story. This episode dives into the growth moments that defined her path, the guidance she would give her younger self, the power of mentorship, and more. Her insights are real, inspiring, and packed with takeaways for anyone who wants to lead with clarity and confidence in the property management space or beyond. Tune in and get inspired to level up your own journey.