Sept. 8, 2025

Betsy Pepine Joins Dori DeCarlo on The Authors Alley

Betsy Pepine Joins Dori DeCarlo on The Authors Alley
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Betsy Pepine Joins Dori DeCarlo on The Authors Alley

Betsy Pepine takes us on her journey as a serial real estate entrepreneur — reflecting on the challenges she’s conquered and the lessons learned along the way.

Betsy Pepine is a best-selling author, speaker and serial entrepreneur in real estate. Her brokerage, Pepine Realty, has been named as an Inc. 5000 Fasting Growing Private Company in the USA multiple times and has earned spots on the Top 50 Florida Companies to Watch and Florida Trend Best Companies to Work For lists.

Additionally, the Wall Street Journal has consistently recognized Betsy’s real estate team as one of the top-producing real estate companies in the United States. Betsy also owns a title company, real estate school and property management brokerage.

 Betsy is endorsed by her mentor, real estate mogul, and Shark Tank shark Barbara Corcoran, as well as leading media personalities Dave Ramsey and Glenn Beck. Passionate about helping at-risk families with children, Betsy founded Pepine Gives, a 501(c)3 non-profit foundation that helps families facing housing insecurity. 

Born in Philadelphia, Betsy now resides in Florida with her family. Her book, “Breaking Boxes Dismantling the Metaphorical Boxes that Bind Us” takes us on her journey as a serial real estate entrepreneur — reflecting on the challenges she’s conquered and the lessons learned along the way.

Join host Dori DeCarlo on a combined Authors Alley and Business Spotlight and connect with Betsy at BetsyPepine.com and on LinkedIn, Instagram, Facebook, TikTok, YouTube and get her book here.

Please support UnsilencedVoices.org a global 501(c)3 nonprofit that empowers survivors of domestic violence, sexual assault, and human trafficking. 

We thank Smith Sisters and the Sunday Drivers for our theme song, "She is You".

Be sure to connect with us come tell us your story!

WordofMomRadio.com - sharing the wisdom of women, in business and in life.

Become a supporter of this podcast: https://www.spreaker.com/podcast/word-of-mom-radio--5252572/support.

WEBVTT

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She is sure, she is true, she is straw straw,

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she is true, is true, she is praise, pray, she

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is she is you.

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Hello, everyone, welcome to today's Word of Mom Radio. Here

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on the Word of Mom Media Network. I'm your host,

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Dori Di Carlo, and you know we are here week

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after week, show after show, breaking those myths that morepreneurs

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and business women, especially those of us building our businesses

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from home, that we're just dabbling in between bake sales

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and getting our nails done.

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We're not.

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We are smart, we are savvy, and we are sharing

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the wisdom of women in business and in life. And

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I'm looking forward to bringing today's guest into our author

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z Ali, but also our business spotlight. Betsy Peppine is

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a best selling author, speaker, and serial entrepreneur in real estate.

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Her brokerage, Pepine Reality, has been named as the Ink

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five thousand's fastest growing private company in the USA multiple times,

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and has earned spots on the top Florida fifty Companies

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to Watch and Florida Trend Best Companies to Work For lists. Additionally,

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The Wall Street Journal has consistently recognized Betsy's real estate

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team as one of the top producing real estate companies

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in the United States. Betsy also owns a title company,

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real estate school, and property management brokerage. Betsy's endorsed by

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her Mentor, real Estate Mogul and Shark Tank Barbara Corkran,

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as well as leading media personalities Dave Ramsey and Glenn Beck.

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Passionate about helping at risk families with children, Betsy founded

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Papine Gibbs, a five oh one c three not for

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profit organization that helps families facing housing insecurity. She's earned

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an ex nomics degree from Duke University in an NBA

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from the Wharton School of Business at the University of Pennsylvania.

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Born in Philly, she now resides in Florida with her family.

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And we're going to be talking about her new book,

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Breaking Boxes, Dismantling the metaphorical Boxes that bind Us. It

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is a really interesting book and I really look forward

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to bringing you in and as I said, I want

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to have you in the business spotlight and the author's

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alli because you are doing so much. So with all

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that being said, Betsy, welcome to Word of Mom Radio.

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Oh thank you for being here. I mean, I appreciate

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you having me here. Very happy to be here.

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It's my pleasure.

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So I would love for you to take us on

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your journey that led you from real estate to now

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becoming an author.

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Okay, real estate I've been doing for twenty years. That

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was actually a second career for me. I got into

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that when I was thirty seven, and I've been doing

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that for the last twenty years. The book was birthed

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about two years ago, and then it came out last year.

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And I say birth because people say, well, why did

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you write it? I'm like, I didn't write it. It

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came out.

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You know.

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It was coming out whether I wanted to or not.

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And the book is surprising to a lot of people

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that know me in my industry. The book really has

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nothing to do with my day job. It has nothing

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to do with real estate. It has everything to do

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with my journey through life. And I call them boxes,

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the boxes that I felt that either I was put

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in or I put myself in that confined me and

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my journey of understanding that boxes exist. What boxes I

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was in, were they serving me? And if not, a

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self evaluation of why am I choosing to stay? If

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they no longer serve me, what is holding me back?

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And then how do I dismantle what is holding me

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back to exit those boxes gracefully. And then the final

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piece was an awareness of what boxes am I unintentionally

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putting others in that may be harming them. So that's

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kind of been in a.

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Nutshell, you know what.

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I find it very interesting, the metaphorical boxes, and I

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want to talk about that. Why they exist and how

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do they serve us and how do they hinder us?

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Yeah? I think so for me, I use the word

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I use the metaphor boxes because I am in real

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estate and I see boxes every day, and I see

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the purpose of these cardboard boxes. They're temporary, you know.

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You use them to pack up your valuables, to keep

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them safe and out of harm's way, and then you

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move to your new location and then you unpack the box,

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and you dismantle the box and you put it out

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at the curb for the garbage pickup day. And I

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think that, unlike those physical boxes, humans have a tendency

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to use boxes, but we put people and ourselves in them,

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and we have a tendency to forget why they exist.

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And so I think boxes exist because metaphorical boxes to

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keep us safe. You know, at the we were hunter gatherers.

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We had probably the first box we knew was danger

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or not dangerous, right, what was a threat to our

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true survival and what was not whether it was an

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animal or another tribe, but it was good bad right

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to protect us. And then it just grew from there

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and it's we have to have boxes because there's so

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much information and data being thrown at us, we cannot

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process it all individually, so we have to make these,

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you know, more broad groupings to help digest the information

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that's coming in at us. I think that they also

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protect us, I mean, and give us comfort. People find

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comfort in maybe their religion or they're being known in

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their family of origin or their race, you know, or

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their ethnicity. There's comfort, there's cultures, there's traditions that are

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passed on, so there's a safety. We're a tribal community

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and so there's a lot of safety in feeling like

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you belong to a certain tribe whatever we're talking about.

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I think the danger is, and it's inherent, is that

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the minute we identify that we're in a box, or

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we identify somebody else in a box, there is a

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tendency to stop seeing them because you see the box

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and you don't need to see the individual. I write

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about a story where I used to take when the

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girls were really young. My daughters were really young. I

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would take them on these hikes in the woods and

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show them all the different types of barks on the trees,

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and the different color leaves, the different shapes, and how

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some have fallen some haven't fallen. And I remember then

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when I taught them the word tree, my girls were

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no longer interested in stopping at each tree, and they

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would pull me along and say, Mom, we know, we know,

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it's just a tree. And that's that's the harm is

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that we feel like we short circuit. We don't need

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to really further explore it because we assume we already

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know it's just a tree.

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You know.

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A more recent example, I remember, you know, a girlfriend

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of mine was had to leave something early because she

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was going to a dinner party and they it's a

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I was asking her about it and she's like, oh,

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we do it once a month. It's a wine. It's

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like a wine pairing, and they choose a different country

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every month. They rotate houses, and you everybody cooks in

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that country of origin, and then you bring wines for

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that from that country. I was like, oh, that sounds

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really fun. And I said, where are you know wear

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that out this month? And she said Father Jeff's. And

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I said, you know, Father Jeff, the priest at Queen

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of Peace. And she's like yeah. And that through me

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and I thought to myself, why I don't know anything

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about Father Jeff other than the fact that he's a

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preset queen a piece. And it's like, wait a minute,

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I was. I had made all these assumptions about Father

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Jeff only knowing he's a priest.

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You know.

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And so I think that's the I mean, that's that's

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a simple and an innocent example. But it can also

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become more more sinister when we start assuming we know

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certain things about people just because the one attribute we

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know one attribute about them.

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I find that that's very interesting.

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Yeah, that's the danger it is because you do we

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put people in different boxes.

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Yeah, we all do, I mean, and the biggest one

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probably is the gender box. I mean we I've often thought,

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even before I was on this journey, when I was

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having my own children, I remember, you know, my in laws,

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I love them dearly, but they very much wanted girls,

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to the point where I was so worried that I

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was going to have a boy, and what would I

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do because they would be so disappointed. And I, you know,

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as now you know, they're in their late twenties, I

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look at that and say, how silly that is. But

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at the time I was like, oh my gosh, I

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just want a healthy child, you know, and who cares

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what gender it is? And even these gender revealed things

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which were not a thing when my girls were growing up.

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But I'm like, what are we celebrating. We know nothing

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about this, we know nothing other than the genitalia, right,

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but we are celebrating it as though it means so

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much more. And what are we telling that child? And

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that's our introduction into the world, right, So that's probably

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the very first box we encounter, even before we're born,

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and then it just it grows from there.

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It's interesting because in today's climate, this whole paranoia. Now,

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you know, kids don't understand gender, boys dresses girls, girls

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stressed as boys. Now, all of a sudden, it's become

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this big thing. It really has, And it's so ridiculous

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to me because, if anything, you're now making people uncomfortable

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when they're really little. She'd just be playing. That's all

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it should be. And you give very candid examples of

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things that happened to you. I understand the weight thing

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because my cousin and I my cousin is still a

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natural size one.

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It's who she is. It always was.

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I'd eat two cookies, she'd eat the bag, and I

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was always the chubby one. And I look back on

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pictures of me when I was doing theater at eighteen

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nineteen years old, thinking to myself, I thought I was back. God,

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I know what a body that I was built like

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Marilyn Monroe when I was fifteen, and I'm dancing with

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girls that are a size zero. So of course I

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was always made to feel because I had breasts and

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rear end and let and again look back at those pictures, going,

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oh my goodness, but.

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Dori, so what if you were so what if you

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look back and you were heavy?

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Not everybody's supposed to be a size too.

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Right, And I feel, you know, we from a time

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we were very young. You know, women's currency is there

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is their looks, and that that just really you know,

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that will set me off on a whole other direction.

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But even my grandmother, who I'm named after, she would

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be Oh my gosh, she'd probably be one hundred and

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fifteen or twenty right now if she was still alive.

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She I remember her telling me all these exercises she

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did as a child to flatten her butt, and yeah,

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she said that was the inesthetic for women. So all

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her friends and her, they would roll on the floor

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to try to flatten their butt because everybody, the boys

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liked the flat butts. I was like, this is crazy.

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Now. My mom was big breasted like me.

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She always shoulders back, head up, love it chest high,

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all way.

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Way.

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There are so many different things in your book that

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just sparked so much in my brain of the things

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that happened and how whether it's intentional or unintentional. H

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it is very easy. Yeah, we'd be put in these boxes.

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Yeah, there are some beautiful examples of extricating ourselves. I

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went to I took my daughter to see Stuffs Up

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in New York City Broadway show, and I remember just

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being an all there was a woman there. So they

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have dancers in the show, right, it's all women's cast,

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And there was a woman dancer in a wheelchair and

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she wasn't playing a handicapped disabled person. She was playing

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a person, a dancer, and it was first time on

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Broadway that I saw someone that was that had that

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disability but wasn't playing a disabled person, and it was

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I mean, it got me teary eyed because I'm like,

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oh my gosh. And then I thought to myself, what

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courage she had, because I don't know if I would

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have had the courage if I was in a wheelchair

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to even think I could audition for a dancing role

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on Broadway. I don't think as much as I would

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hope I would could do that, I don't know if

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I would have thought that would have been in my

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consideration set. Yet she did and got the part, and

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I just it was just so beautiful to see that.

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On that note, think the example Betsy just gave.

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We're going to take a really quick break and we'll

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be back here in just a moment.

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On Word of Mom.

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Radio, she is brave, she is bold, she is you,

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Go to wordommradio dot com and register as a guest.

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we all win.

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of domestic abuse and gender based violence worldwide. The organization

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currently serves Siri Leone, Rwanda, Ghana, and the USA. In

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org for more information.

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And we're back here on Word of Mom Radio. We

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are talking with Betsy Pepine. I love the example you

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just gave of the woman in a wheelchair auditioning as

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a dancer.

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You know, when they did the.

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Revival of Oklahoma, ado Annie, the actress who played ado

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Annie was in wheelchair. Again, not a part for somebody

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who's disabled. And the new movie Wicked. If you've seen

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the movie Wicked, woman who plays Alpha's sister is in

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a wheelchair. I'm somebody who's worked with people with mobility issues,

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So I knew right from just the brace that she

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was wearing.

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I was like, WHOA, this girl's really in a wheelchair.

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Yeah, I love it. Yeah.

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Nothing excites me more as somebody who's worked with people

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with mobility issues than to see people integrated into shows.

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It's so it really is important, and I love that

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you and your daughter got to experience that.

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Yeah, it was great.

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So let's go back to the book.

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I'm going to ask you, with all the boxes that

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can surround us, how do we gracefully get out of them?

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Betsy?

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So, I'm no expert, but from my personal experience, the

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first step for change is to be even aware, right,

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And so you have to be aware that you're in

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a box to even be able to contemplate getting out

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of one, and to be aware that a box exists

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means that you are consciously attuned to the fact that

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there are other choices for you. And so that sometimes

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takes a while, because sometimes you think, oh, this is

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the only path, and you don't know why, because maybe

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it's what your family's always done, you know, and you've

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always been told from a little child, this is what

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we do in our family, but time out, No, this

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is I have other choices, right, So being aware that

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you have other choices, and also for me it was

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getting your body will tell you before your mind. If

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a box is no longer serving you, you will feel

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it in your body. And so the more you are

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attuned to how you feel, the more you're going to

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be aware that a box may no longer be serving you.

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And that's me a long time because I was not

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raised in a home where feelings were talked about, expressed,

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encouraged to be explored, and so it may be harder

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for some than others. It was very difficult for me

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and I'm still on a journey of doing that. So anyway,

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get understanding then what boxes or holding you back? And

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I always say start with the biggest one, What is

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the one that's causing you the least the most pain

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in your life? And then identified you know, if you're

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staying in a box that's no longer serving you, it

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is serving you in some way. It's there is because

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we wouldn't stay in something that, even if it's seems counterintuitive,

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is serving us. And so what what fear are you

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placating to stay in that box. So it could be

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fear of failure. You know, that's a big one in

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our society. A lot of people. I'm in real estate

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and we have a lot of agents that join our brokerage,

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and I see fear of failure is just seems to

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be universal. I look at that I have. That's a box.

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Failure is a box. Failure is a label that you

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may choose to put on an outcome if you so choose,

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But you don't have to choose that like I don't choose,

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I truly choose. I do not have failure in my life.

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That does not mean that everything goes my way. It

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means that I am very well aware if something doesn't

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go my way. I say to myself, Betsy, what's the

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worst case, I'll have to pivot. If you've reached your

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mid fifties, we've all had to pivot unexpectedly at some

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point in our lives, and we've made it here. So Okay,

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I got a pivot. I know I can handle that,

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and I will get to take a very important lesson

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or learning with me for the rest of my life.

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I don't know what that learning will be right now,

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but I know that if it doesn't work my way,

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I will have learned something incredible that I get to

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take with me for the rest of my life. That

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is worst case scenario, and research has shown worst case

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scenario happens approximately two to three percent of the time.

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So failure really, when you actually break it down, it's

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just a mental construct and if you can just to me,

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that's the easiest one to combat. There is fear of loss,

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you know, that could be loss of social status. You know,

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when you whenever you move, it's like a chess game,

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and whenever you make a move in your life, you're

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going to ruffle some feathers, you know. When I chose

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I used to be in pharma and then I decided

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to go into real estate. That was a huge demotion

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my family, being coming from a family of all physicians,

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being incredibly feeling a lot of pressure to be one myself,

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and then choosing to be in a career that requires

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a ged and a one week course did not sit

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well with my family and was I definitely felt like

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I was knocked down a couple pegs in the status

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of my family when I chose that career. So fear

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of you know, it could be a fear of status

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change ego, and that's just ego. I say to myself,

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that's say that's your ego talking puts your ego on

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the shelf. Move towards the direction of your dreams, because

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we are not our egos, So really identify what is it?

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Is it loss, is it failure, or it could be

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financial security. A lot of times when people want to

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make a move, it involves a career change, and financial

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loss is a big fear. But I do believe nowadays,

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with the gig economy, with everything being remote, with access

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to the internet, it's so easy to supplement your income

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while trying to bridge the gap between your day job

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and your dream job. So I think that one is

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a little bit less scary for people nowadays. But the

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key is to a break down what is it that

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you're fearing, what is holding you back, which of those

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things and work yourself through that and then just plan

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baby steps. What's something very small that you can do

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today that will move you towards that something that I

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do every day and I track it. I a habit tracker,

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but I practice doing something new or uncomfortable every day

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because to me, that's a muscle. And the more I

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do things that make me uncomfortable or that are new

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to me. That muscle gets strengthened so that when I'm

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faced with something that's uncomfortable, it's not as uncomfortable. I

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know I can muster through that because I practice that

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experience every day. So just again, work through your fears.

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What are some things you can be doing today to

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help you get out of that box? Break it down.

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I'm a big believer in breaking things down into very baby,

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doable steps that get you towards your goal.

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What a great way to wrap up this conversation, Betsy,

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as we are closing out, what would you like to

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leave our listeners with? What do you want to say

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to that woman out there listening right now?

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I just think we have so much untapped potential within ourselves,

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and so I would just encourage everybody to take the

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next step into a life that is fulfilling for you.

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If you're unhappy. If you're not unhappy, fine, great, But

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if there's something that's unsettling in your life, have the

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courage seek out mentors. Women want to help other women.

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If we know people need help, we want to be

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there for you. So seek out mentors who have been there,

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that are a couple of steps ahead of you to

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help you on your journey.

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How can they reach out to you?

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Betsy, I have I'm all over social media with my

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name Betsy Peppine. I'm also I've got a website, Betsy

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Peppine dot com. Those are the two easiest ways.

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We're gonna have links to everything, Betsy's book and everything else.

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And I really encourage you to buy the book because.

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Most of the time, the boxes and limitations that we

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put on ourselves, we put on ourselves, we really do.

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It's an amazing thing. And I think back to my

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two favorite things, you know, that little red engine, I

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00:23:37.359 --> 00:23:38.440
think I can, I think I can.

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I think I can, I thought I.

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Could, and everything and Henry Ford his quote, whether you

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00:23:45.000 --> 00:23:49.200
think you can or you think you can't, you are right.

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Yeah, so true.

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And if life is showing us anything, it's that it

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is limitless possibilities.

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There's a lot of stuff going.

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On around us that we might not be able to control,

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but what's going on in our own world, in our

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own sphere, and especially within ourselves, we can break out

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through those boxes and everything else because the only thing

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that's holding us back is that and the other thing

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when you were talking about you know, I've always lived

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with we don't win or lose, we win or we learn,

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So I loved what you had to say. So Betsy,

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00:24:33.119 --> 00:24:35.960
I just thank you so much for sharing your book

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00:24:35.960 --> 00:24:41.279
and your journey with us. Congratulations on what you have

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00:24:41.519 --> 00:24:45.480
created for yourself. Really, just kudos to you.

431
00:24:46.079 --> 00:24:47.839
Well, thank you, Thank you for having me.

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00:24:48.079 --> 00:24:51.079
Oh it has been my absolute pleasure. And for all

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00:24:51.079 --> 00:24:53.960
of you tuning in, thank you so much for being

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00:24:54.000 --> 00:24:56.519
here again. All of Betsy's links are going to be

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00:24:56.599 --> 00:25:00.119
live reach out. It really is a good book and

436
00:25:00.440 --> 00:25:01.799
I think one that will open your.

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00:25:01.720 --> 00:25:02.839
Eyes to some things.

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So go for it, and thank you so much for

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00:25:06.160 --> 00:25:09.240
being here. We're going to close out with our fabulous

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moon song from Smith's Sisters and the Sunday Drivers. So

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till next time, This is dor di Carlo saying, go

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out and create a marvelous youth.

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Bye for now.

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She is sure, she is sure, she is strong, she

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is strong, she is true, she is true. She is

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braz Bray, she is boul, she is she is you,

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is you, she is you, she is she is sure.

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She is sure, she is strong, she is strong, she

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is true, she is true, she is brave. Bray, she

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is bold, she is she is you.

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She is you, she is you, she is you.

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Sure of herself, Yes, she takes care of his Powerful

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and strong. Yes, she knows who she is, has integrity, woman,

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strong and true. You know her by name. See this

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woman as you. She is sure, she is strong, he

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is strong, she is true, is true, she is brave,

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she is.

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She is you, is you?

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She is she is sure, she is strong, is strong,

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00:26:15.920 --> 00:26:21.079
she is true, is true, she is brave, she is

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she is she is she. She is adds value and hope,

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has proved to be brave. See it's never too late,

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never time to behave Reaching for dreams doesn't matter. The

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00:26:34.480 --> 00:26:38.799
age believes in herself from her cage. She is sure,

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she is sure, she is strong, is strong, she is true,

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is true, she is brave, she is bold, is you.

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She is she.

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Is sure, she is she is strong, she is strong,

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she is true, is true, she is brave, is brave,

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she is bold as well. She is you.

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Betsy Pepine Profile Photo

Betsy Pepine

Breaking Boxes

Betsy Pepine is a best-selling author, speaker and serial entrepreneur in real estate. Her brokerage, Pepine Realty, has been named as an Inc. 5000 Fasting Growing Private Company in the USA multiple times and has earned spots on the Top 50 Florida Companies to Watch and Florida Trend Best Companies to Work For lists. Additionally, the Wall Street Journal has consistently recognized Betsy’s real estate team as one of the top-producing real estate companies in the United States. Betsy also owns a title company, real estate school and property management brokerage.

Betsy is endorsed by her mentor, real estate mogul, and Shark Tank shark Barbara Corcoran, as well as leading media personalities Dave Ramsey and Glenn Beck.

Passionate about helping at-risk families with children, Betsy founded Pepine Gives, a 501(c)3 non-profit foundation that helps families facing housing insecurity.

Betsy earned an economics degree from Duke University and an MBA from The Wharton School of Business at the University of Pennsylvania. Born in Philadelphia, Betsy now resides in Florida with her family.