Breaking Boxes

We explore how success without joy pushes you to redefine life on your terms, and how dismantling the boxes of expectation can unlock purpose, resilience, and impact. Betsy shares practical tools for healing, building a mission‑driven business, and choosing joy daily.

• rising from divorce and layoff to design a new career path
• naming family and cultural boxes that limit growth
• creating a two‑year pivot plan with clear contingencies
• therapy, EMDR, yoga, and journaling as healing tools
• reframing failure as learning and pivoting
• detaching from praise and criticism to reduce fear
• joy as a daily state, not a fleeting emotion
• building housing impact through a focused nonprofit
• living intentionally with what you read, hear, and who you keep close
• where to find Breaking Boxes and connect with Betsy

Purchase “Dismantling the Metaphorical Boxes That Bind Us” on Amazon, Target, or BetsyPepine.com. Connect on social at @BetsyPepine.

Get ready to break free from obstacles and live life on your terms!

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Chapters

• 0:00 Welcome And Mission Of The Show
• 3:23 Meet Betsy Papine And Her Path
• 5:54 Divorce, Layoff, And Pivot To Real Estate
• 9:36 Family Expectations And Living Others’ Plans
• 13:05 Planning The Leap And Killing Plan B
• 16:03 Midlife Success Yet Unhappy
• 19:44 The Boxes That Don’t Serve Us
• 23:11 Tools For Healing: Therapy, EMDR, Journaling
• 27:13 Joy Versus Happiness
• 30:13 Resilience: Redefining Failure And Detachment

Transcript

Cassandra: 0:50

Good day out there to all my listeners, and I'd like to welcome you to Is Your Way and Your Way podcast. And for those new listeners out there, I'd like to introduce myself to you. I am your host. My name is Cassandra Crawley Mayo. And also, you, many of you are aware that this podcast is really about self-improvement. I would say personal, personal development. And I always have a prayer prior to any of my episodes that something said by a guest will motivate you to pivot and do what it is that's going to enable you to start living your best life on your terms. So today, on is your way in your way, I'm gonna pull back the curtains on how to overcome barriers, redefine success on your terms, and learn that the real measure of achievement isn't just the size of your portfolio, it's the size of your impact. So, what beliefs you need to break to build that life, you you are called to live. Stay tuned, you're about to find out. I'd like to introduce my special guest to you, and her name is Betsy Pepine, Pepine, Pepine, Pepine, Pippee, Pippee. I just asked her how to pronounce her last name, and I didn't get it right, but but that's kind of okay. I got it now. I'd like to welcome you to Is Your Way in Your Way. Oh, thank you. I'm very happy to be here, Cassandra. Yeah, you know, um, your journey kind of mirrors the mission of this show, and it's all about overcoming personal and professional barriers to create the life of purpose. And also, it you even though you rose to the top, wasn't just about business savvy, it took courage for you to step out of your comfort zone of willingness to serve others, and I just want to applaud you for that because you're just living proof that when you remove those limits you place on yourself, you can impact lives on a massive scale. So, kudos to you. Kudos, thank you. Sure, I'm gonna read a little bit of your bio just so my listeners understand what qualifies you to talk about. And our topic today is this man how to dismantle the boxes that no longer serve you. So, Betsy is a best-selling author, serial entrepreneur, powerhouse in real estate, whose brokerage, her she has a reality company, has repeatedly ranked among the nation's fastest growing private companies and top producing real estate teams. She is endorsed by the giant like Barbara Cochran and Dave Ramsey. And for you, no Barbara, who was on a Shark Tank, and we all know who Dave Ramsey is, the financial whiz. Uh, Betsy's leadership extended beyond her business. She's the founder of Pipping, Pipping, Pipping, Pipping gives, a nonprofit dedicated to helping at-risk families secure housing. Also owns a title company, real estate school, a property management firm. She combines business brilliance with a heart for service, showing that success and significance can and should coexist. So, Betsy, let's tell our listeners who who are you? Tell us about your background a little bit, your backstory. Who is Betsy?

Betsy: 4:36

Oh, that's a tough one. Um, I describe myself as a wonderer, somebody who's just insanely curious about all things, um, constantly wanting to learn and grow um internally, externally, through other people. Um so that's how I would describe myself. Uh, first and foremost, in terms of roles, I'm a mom, single mom of two incredible daughters, um, a daughter, uh a sister. But I am an entrepreneur. Um, I it was just definitely a second career for me. I started out in a in a career in the pharmaceutical industry in the marketing um sector, and I did that for almost a decade, and really was not my passion at all, but it served a lot of other needs for me at the time. Okay. You know, and then through through a unexpected divorce and layoff at roughly the same time, I decided that God was trying to tell me that I was not on the right path and perhaps I should pursue something else, and um and decided to pursue real estate, which is something that I'd always had an interest in. And so I did that. I started 20 years ago and I just started building honestly companies after that. I started my brokerage, then I started a mortgage company, I started a title company, I started a real estate school, started a property management company, and most importantly, started a nonprofit that serves the cost-burdened families in our area with their housing needs.

Cassandra: 6:13

Wow, you've done a lot. Let me ask you, did your backstory growing up have anything to do with what you're currently doing?

Betsy: 6:21

Yes, it did in a in a roundabout way. Um, yeah, I mean, I my back my family of origin is um heavily into uh the healthcare industry, and I had a lot of pressure um to enter that industry. And so my sisters and I all went to the same college. We all were pre-med. We all worked alongside our fathers in our summers, um, helping him and his colleagues. And so that was just expected. And so, and that's why I pursued the path that I did um out of college. I decided I knew I didn't want to be a physician that would not have spoken to my soul, but I did stay in the pharmaceutical industry to stay in the healthcare space. Um, so so yeah, so that part contributed to where I am today. Um, I think I got really frustrated because I felt like I was at that time, you know, living somebody else's life, not mine. You know, I was living somebody else's um expectations of me and not really pursuing what I wanted to pursue. And as is often the case, sometimes our greatest um setbacks are our greatest opportunities for growth. And I think it was because I had the setback of a divorce as well as being laid off of a corporate job, it made me reevaluate my life and the direction I was headed and made some significant changes so that I would be leading a more uh a life that was more parallel to what fulfilled me and made me happy, but made my heart sing.

Cassandra: 7:56

Yeah. Um yeah, yeah, I like that because many of my listeners today are unhappy or not really doing what they want to do, but yet uh like many of us will do probably what our parents wanted us to do. I know individuals personally of that, and that's not it. So, what was it about you or what is it that enabled you to pivot? I'm not saying you didn't struggle in doing so, yeah, but just something that perhaps will help my listeners understand. Well, how did you do that? Was that this was this in your DNA? Were you rebellious because of what I mean? What was really happening?

Betsy: 8:40

Um, I don't know. I I do think I was probably considered, I am definitely considered now the black sheep of the family because I am the only one that's divorced, um, and I'm the only one that's not a physician.

Cassandra: 8:53

Okay.

Betsy: 8:54

Um and I honestly don't think I think I'd still be in the pharmaceutical industry had I not had those two experiences. So I'm so blessed to have had those two experiences because I'm so much happier now than I ever would have been in pharma. I was staying in that role because I liked the income. I liked the I did like the quality of life. Like I didn't have to do a lot of um, I didn't have to do a lot of work outside of the nine to five, and that was important to me because I had two very young daughters at the time. So I liked the quality of life, I liked they they they allowed you to travel, which I liked, and I liked the income, but I was not passionate about the job. Okay. You know, and life is so short not to be passionate about what you're doing on a day-to-day basis. Yeah, absolutely. And I think I got to the point where it's like, what do else, what else do I have to lose? I lost my job, I lost my marriage. You know, that so pivoting then seemed, I think, a lot more doable than had I not had had those two experiences. So, relatively speaking, that was an easy pivot. Okay, yeah, okay, yeah.

Cassandra: 10:01

And I I like that because uh, you know, we all know life is tough, you know, and a lot of times we we have choices. Uh we could be bitter about what happened to us in our life, uh, be better. And you chose that, not really knowing what the future would look like, but you knew that what do I have to lose? Why not? Right.

Betsy: 10:26

Why not? And I mean, I did have a plan, and I think it helps to have a plan. So I gave myself two years. I I had I had enough of a nest egg that I could live very meagerly for two years and be okay. And so I thought, okay, if it doesn't, if I haven't made it on my own in two years, then I'll go. And my plan B was to go to the large healthcare facility in our town and work in their marketing department. But fortunately, I didn't have to do plan B. Plan A worked out.

Cassandra: 10:51

Okay, good. Excellent, excellent. Uh, they always say sometimes if you do have a plan B, you can kind of fall back, but just having that one plan, it's like, okay, I gotta do this because this is my only my only plan. So good for you. Uh Betsy, I I've noticed that there was a point in your career where you you had the kids, you said the business, you've been in real estate, you were in a you were in a good place, but there were points in your life you were unhappy. Okay, so around the age of 40. Yeah. Um, did that have anything to do with the divorce? The uh okay, what what were you unhappy about? What was going on?

Betsy: 11:35

Yeah, that was um the realization that I felt like I had worked all my life and I had I had I was I am very blessed with business success. And I and I understand that. Um, and I think that's what took me so long to even acknowledge to myself that I wasn't happy because I think on paper, if you looked at my life, it it it looked good, and it almost to me was the irresponsible to even suggest I wasn't happy, yeah. But I wasn't, and so I had to get real with myself. Like, you know, 40, I think maybe is a maybe that number, I don't know, but just makes you start to reevaluate things and you recognize life doesn't continue forever, and do I want to continue living this way? And I felt like I had gone through life just checking off all the boxes that that almost like the definition of success. If I do X, Y, and Z, then I'll be happy. And so yes, I was successful in this the eyes of society, but I wasn't happy.

Cassandra: 12:37

Yes.

Betsy: 12:38

And so that led me on this journey that and I'm still on the journey. Um, and it involved therapy, like one-on-one therapy. It involved a ton of reading, bioenergetic work, EMDR, meditation, yoga, um, just a whole bunch of different modalities, journaling, and I which I still participate in these things. And it just led me to this realization that my source of unhappiness was because I in various aspects of my life, I had felt and sometimes occasionally still feel contained. I feel like I'm in these boxes that I didn't necessarily ask to be in, but I found myself in, that perhaps maybe served me at some point in my life, but no longer serve me now, or maybe never serve me, but now I'm just realizing that they never served me. And I began a process of extricating myself from those boxes that no longer serve me. But that was the source of my unhappiness. The boxes could be, you know, my family of origin box. I'm so blessed to be in the family that I'm in. Everyone has, you know, there's always great things about being a part of someone's family. But there's also there's also negative things. And, you know, for me, just this huge weight of feeling inferior because I wasn't in the medical profession, or you know, that I'm raised in a very Catholic family, yet I'm the only one that's divorced. Um, or you know, there's there are certain expectations that we all face just based on our gender. And they may not fit my my mold. So anyway, so those are some of the boxes that we face. But there's I mean, thousands of boxes. You look at them, you start seeing them everywhere once you become aware of them. But trying to identify which boxes were no longer serving me and why was I choosing to stay in boxes that no longer serve me, recognizing it was real fear-based, you know, fear of failure, fear of loss, fear of financial insecurity, um, fear of, you know, being demoted in social status, you know, all these ego-based things. And then really addressing those head on with myself. I found journaling to be very helpful, writing things down. Okay, Betsy, worst case scenario, what could happen? Um, worst case scenario doesn't look so bad when it's on paper. Um, and redefining what failure is. Failure, I realize, is just another box, and I can choose to have it in my life or not have it in my life, and so I banned that box from my life years ago. You know, so it was just that process of un understanding which boxes are holding me back and how do I eliminate eliminate those in my life, right?

Cassandra: 15:25

And that was a process, like you said. Oh, yeah, we're still on it. Yeah, yeah, absolutely. And emdr. Tell my my listeners what that means, EMDR.

Betsy: 15:36

EMDR, I don't honestly don't remember what it stands for. The it's an acronym for something, but it's basically rewiring. Um it's a it's a methodology that therapists use with their patients to help um unblock trauma that can be trapped in your body. And so it's um actually now that you say I think it it's the eye, it's I think the E is I and R is rapid, but it's this science. The science behind it is basically this rapid eye movement they have found somehow rewires your brain to process events in a more positive way. And so you can you can reframe things, it's kind of like in your subconscious. I mean, I'm not a psychological psychologist, so I would you know Google it, but basically it's helping you rewire events in your past so that they no longer hold you back.

Cassandra: 16:54

Okay, it's it's an eye movement to sense the sensitization and reprocessing. Yes, that's yeah, yeah, okay, yeah, okay. Yeah, that that's I I've heard individuals go through that process and obviously it helped, but obviously, like you said, we're still here and it's a process, yeah, and we'll continue to be a working process, but yet you are still in a different place, and that's what what what you needed, you realize that. Yeah, yeah. So um could you tell me so you rediscover your joy, so to speak, just all those things that you went through. Yeah, is there a difference between joy versus happy?

Betsy: 17:59

Yes, I think so. Yes, and I felt like I was just kind of soldiering through life.

Cassandra: 18:04

Uh-huh. Right. Just striving, not thriving.

Betsy: 18:08

Right. And um, yes, I absolutely I think that happiness for me is an emotion. So it's like it's transitory, it's it's fleeing. Whereas joy is a state of being. That's how I look at it in my mind. Okay. And it's I actually joy is something that I track every I have a daily tracker and I um I track, I track different things I want to create in my life and manifest in my life, and joy is one of them. And so at the end of each day, I I'm accountable to was my day joyful. Um certain people, you know, yes, I could have been happy one moment, not happy one moment, but overall was was my day joyous. And really, you know, I remember um years ago, I took a personality profiling thing at church, and it was something that I had not, I mean, I've done a lot of personality profiles. This was something totally different, but anyway, you basically got a flag for the country that you resided in. And I resided in the control country, the country of the control. That's where I live. Yeah, right. Well, there's another group that resides in the joy country, and it was so enlightening to me because there were people in that audience that every day, the first question they ask themselves when they wake up is, How will I have joy today? And prior to being in that room, that question had never been one I asked myself. Yeah. Never. And I was like, wow, there are people that that is their goal every day. How am I gonna have joy and experience joy? Yeah, um, so having to like getting to reframe that, it's just so it's almost like a kid in the candy store. I mean, it's theirs for it's there for your taking. Um, so yeah, so I think joy is is kind of a is a state of being, whereas happiness to me is more kind of transitory and yeah, yeah.

Cassandra: 20:08

My thing is I'd rather have joy if I had to select happiness, because I always see happiness as a happening. You know, I remember the day I got married, I was happy. Yeah, okay. That was it, right? Yeah, I got my dream car, I was happy. Yeah, it doesn't last forever. So, and I think joy is priceless, like peace is priceless. Yeah, so so I I like what you said.

Betsy: 20:35

Um, there's a there's a great book that just came out called Joy Span. You know, there's this, there's you know, we have lifespan, right? And then the next stage of people they're they're looking at health span. Health is your quality of life during your life, because why is it why is it great to have um longevity if you're not healthy? Then a third component is joy span. Why, why have a healthy and long life if you're not having joy? So, how do you create how do you create a long, healthy life filled with joy?

Cassandra: 21:10

Right, right. Excuse me, but that was Max. My listeners know who Max says, and he's not in the room, but he just he always wants to be a part of the podcast, unfortunately. Um, what strategies have helped you maintain your resilience and fuel and your leadership? Success. Because you're you're successful now. And you got that other life stuff going on. Yeah. But you have to think about it. You have been resilient.

Betsy: 21:43

Yes, I I definitely have. And it's definitely something that I've worked on. Um so redefining failure, so understanding so truly, I don't I don't believe failure exists in my life. It doesn't mean I get everything I want and that everything works out the way I want. It means that even if something doesn't work out the way I want, I know I'll have to pivot. I know I've pivoted before when I didn't want to, and it's worked out just fine. And I'll have learned something very valuable that I get to take with me for the rest of my life.

Cassandra: 22:19

Okay.

Betsy: 22:19

So that's worst case scenario. So that to me is not failure. And so I feel like that frees me up. So when I'm evaluating, should I do something? Should I make a move? Should I whatever the whatever I'm questioning, where I think a lot of people are held back by fear of failure. I am not, because I don't believe in that, that does just doesn't exist. Okay. Um, I think the other thing that's really helped me is it was a process, it and it started years ago, but I stopped taking anything personally. Anything. I mean, any any anybody's opinions of me, whether they're good or bad, have nothing to do with me. So even when somebody gives me a compliment, while I'm gracious and say thank you, I know, I truly know internally that has nothing to do with me. That's their perception of me, that's the way they were raised, that's what they value, has nothing to do with me. Yeah. And that frees you up because you become impervious to what others think of you. So again, that that fear of, oh my gosh, how are other people going to perceive me if X happens? That that's helped me become a lot more resilient.

Cassandra: 23:36

Yeah, that's a great. Um, I had a professor, and I'll never forget this. And and it was a husband-wife team, and one of the things they always said is feedback, but people say it's more about the giver than the receiver. And I kind of thought about that because you think of yourself giving someone feedback, you know, saying something to someone. Is it more about it's really more about you than it is them? So I like that mindset that you've created to help you switch over and and rewire and change the narrative. Yeah, I love that. I love that. I want to ask you, but I'm really impressed. Uh your business, you're doing well, I think that's great. But something else I think that's just as powerful is your giving back, you know, this passion to help at-risk families. What did I know? You said when you at home or you were somewhere, something happened. You had something happened when you were in Philadelphia or something like that.

Betsy: 24:37

Yeah, I went to graduate, I went to graduate school in Philadelphia and I was getting an MBA. And just oddly, one of the classes that you could take for credit was gutting row homes in West Philadelphia and rebuilding them with donated supplies and labor. And then we interviewed cost-burdened families and sold those homes to those families at cost. Oh, and so I was in my early 20s and I could see how a house impacts the trajectory of that family, the family tree. I mean, it impacts health outcomes, it incacts educational levels, so many different measures, it impacts more than just having a roof over your head. And so that stayed with me. And then when I started um, you know, getting into real estate, I'd always given back in other ways, you know, rescue, I'm still passionate about, but all these different kind of incongruent ways I was giving back. But about probably eight or nine years ago now, I said, well, how can I if my my goal isn't just to do service, my goal is to make an impact. So if you want to make an impact, how can I do that most effectively? And I thought, okay, well, one, funnel all of your activities into one more narrow focus, and two, do what you're good at. I always say stay in your lane. Well, I'm in real estate, I love all things real estate. So let's give back, make an impact in real estate, and how best to do that by serving a segment of the population that needs our services, but will never be able to use them through the front door. Yes. So that's kind of how that came to be. So I created a nonprofit and we have a partnership with Habitat for Humanity, and we um fundraise and build houses and provide those to um, not provide those, they buy them, but we team them up for success. Um, we there's educational training on how to maintain a home, there's educational training on how to maintain a household budget. So we're really trying to, you know, change these families and their in their family tree with through help.

Cassandra: 26:51

Wow, that is major. And like I said, it's more blessed to give than receive. Yeah, and that in itself should make you feel really good about yourself. So congratulations to you. Well, thank you. Yeah. Uh well, let me one more question because you are in a better space than you were, you know. Um where you are now, what would you tell your 30-year-old self?

Betsy: 27:25

Well, I mean, I would I would tell my 30-year-old self, because that was right around the time I was getting divorced with a one and two year old. And I would tell my I would tell my 30-year-old self everything is gonna be okay. You know, because that was a very scary time. Um I would I would tell, and I have children who are 27 and 26 now, um, you know, and I would say, and I advocate this to my agents as well, is as early as you can to live your life intentionally, you know, it goes by so quickly, and um just live every moment intentionally. That and that includes what you choose to have your eyes read, what you're what you choose to have your ears hear, who you choose to be around and associate with. You know, it's it's all encompassing.

Cassandra: 28:18

It it really is. Yeah, good, great, great wisdom. And you also have your you, like I said, you're an author of the best-selling book, and the book is breaking boxes, right? Yeah, dismantling the metaphorical boxes that bind us. So tell my listeners how they can get the book and how would they be able to get in touch with you?

Betsy: 28:44

Sure. So the book is available on all the major book retailers, Amazon, Target, any kind of major book retailer. It's also available on my website, which is my name, BetsyPapine.com. And then I'm on all the social channels again with my name at Betsy Pepine.

Cassandra: 29:01

Okay, okay. Well, Betsy Pepine, finally got it. I want to thank you for your time, um, your wisdom, and your candor about, you know, things that you've experienced. Uh, I think that's very helpful. And I think when we are open, not with everything, but open, that is a cause for transformation, you know, and you gravitate individuals into your into your life, so to speak, because you are not alone in whatever you have been through. So just for people to witness that and also see your success and understanding it's not always about the money, you know, it's not always about what somebody else wants you to do. This life is short, as you indicated. And and that's why I always preface it is by saying, live your best life on your terms. That's critical. And a lot of people don't know what that is, but I'm hopeful by this time um they they kind of figuring it out and understanding the boxes that they're in and they how they need to dismantle. And they could do that by purchasing your book and listening like this podcast again. So, again, thank you so much. Well, thank you, Cassandra. I appreciate it. Sure.