Ep 89. How to Reinvent Yourself Without Fear of Being Judged

From Burnout to Becoming Someone New

It built me, and it crushed me, all at the same time. And I wasn’t expecting such a rich transformation in such a short period of time. Meet Jenn Pike, entrepreneur, author, and women’s health educator with 30 years of experience. She’s built a successful global business, but her biggest transformation wasn’t just about success. It was about becoming someone new.

Jenn : I think for me, it was, can I pull this off? Can I get up there and stand on the stage and pull this dress off without being judged? How do you be her now in the everyday things? I feel like I don’t really know her. I feel like there’s this alter ego that has come forward.

Danielle: So, Jenn , I’m going to ask you a little bit about your story. First, I’d like to acknowledge what I’ve witnessed on stage at Pink Skirt. The woman that came out on stage was really moving to see as someone who knows you and was with you a few months prior in the mastermind, I guess in January, to see you walk out in that dress and rock the presentation. Of course you’d rock it. I wasn’t expecting anything less. But I wasn’t expecting such a rich transformation in such a short period of time. So I want to talk to you about that today and take a peek behind the scenes as to what got you there.

The Business That Built Her and Burned Her Out

Jenn : I had opened up my own in-person business. I had a boutique studio. Best and hardest thing I’ve ever done in my life. I always talk about this: when you work for other people, you always think you can do the job better. Like, “Oh, if this was my place, I would do this and I would do that.” And then it’s your place, and now you’re responsible for everything and everyone.

Saying yes to building that business, it built me and it crushed me all at the same time. I had a lot of days where I had to show up with a certain energy. I had to perform, while behind the scenes, I was in deep, deep burnout. And the deeper I got into my own personal burnout, the more resentful I was becoming toward the thing I actually loved so much.

It was an interesting period of time in my life where I loved what I was doing so deeply, and yet it was actually deteriorating me at such a high level. As time went on, I really recognized that, and my burnout became the birthplace of the audacious woman. I had to make some deep decisions, and I did. I sold that company and moved everything online. I’ve been fully online since 2016, so I was really ahead of the curve when everyone else started doing that in 2020. I got to put the reps in and practice what that felt like.

Now I sit here, 10 years later, and I’ve built a really successful global online company. I’ve written books, and I just handed in my newest manuscript. That moment on the stage at Pink Skirt made me realize, “Oh, I am actually fully stepping into the evolution. I feel like I’m moving into the legacy years of my work.”

I feel like the last 30 years were the brick-and-mortar years, literally one brick at a time, building this foundation in business, in my body, in my life, and in my relationships. Now, as I transition into these next 30 years of my life, there’s a different woman who has been woken up in here and is taking me forward.

Danielle: Amazing. I want to go back to one part of your story: the burnout. When you sold that business, in hindsight, are you able to see why that season was so necessary, especially because of the birth of the audacious woman that came after it?

Jenn : I was always told from the youngest age, “You’ve got this.” I was like a one-woman show from when I was a little kid. “We don’t have to worry about you. You’ve got this. You walk your own path. You create your own reality.”

I was never the person you had to tell, “You should go do this,” or “You should work harder,” or “You should figure this out.” I was like, “I’ve got it. I’ve got it.” It’s amazing at the time, and I am so grateful for that version of me. Bless her and her blissfully ignorant little soul that didn’t understand what was on the other side of it.

But I believe I needed to go through that because I didn’t know how to ask for help. I would ask for help, but then I would micromanage the help I was being given. I always felt like I had to be the one doing more for everyone else. I look back in two ways. I look back with so much gratitude. I wouldn’t even be the kind of woman who would be invited to have this conversation with you today had I not done that and gone through it.

I also look back and think, wow, if I had just had the right mentorship or the right people around me, I could have taken that business and made it successful in a different way without compromising myself at so many different points. I think that’s why I’m so passionate about business mentorship for women now. I’ve seen the possibilities, and I’ve seen the multiple sides of what can happen. For a lot of us, we make things so much harder than they have to be.

Danielle: I totally resonate with all of that. Let’s talk about Pink Skirt and the woman who walked on stage in that dress. Everyone listening, please go find Jenn on Instagram and scroll back to the pink section on our page, because you’ll see her at Pink Skirt. You’ll want to take a screenshot and use your fingers to make the image bigger to look at her dress and your cleavage!

Now I’m thinking, what am I ever going to wear on stage again? When we’re speaking at Sam’s event, I’m like, “What the heck am I going to wear?” My husband was like, “Just put the same dress on.” I’m like, “I can’t do that. I can’t do that. What am I going to wear?”

It was so good. So good. I think you said on stage that your daughter was the one who encouraged you to wear it. Was she?

The Pink Dress Decision

Jenn : I had a dress that was very much me. I had my safe dress, and then I had this dress. The talk I was giving was called “The Audacious Entrepreneur,” which was all about being an audacious woman. When I saw this dress online, I thought, “Ooh, I’m just going to buy it and see what it feels like and looks like when I get it.”

When I got it, I came out in my safe dress first. My husband, my son, and my daughter were there, and they each had two friends over. They were like, “Oh, that’s really pretty.” Then I came out in the other dress, and immediately my husband and my son were like, “Absolutely not.”

Chris was like, “Yes, love it,” and Sam was like, “You can’t wear that on stage.” Then my daughter was like, “Mom, you cannot wear the other dress.” She said, “The other dress looks cheap now. Mom, you have to. This is the audacious dress. You have to wear this dress.”

But, being me, I showed up that day to hair and makeup with both dresses.

Danielle: You did?

Jenn : I had them both with me. I walked in, and Renee and Anita were in the back. Renee was like, “Oh, are you doing a dress change?” I said, “I don’t know which one I’m wearing.” I needed to have this backup.

I did my hair and makeup, and then my makeup artist, Jenny, said, “Okay, let’s get you into your dress.” I said, “Well, I brought two. I’m going to put on the one that I’m not too sure about first.” I literally went behind a drape, like a curtain at the window, and put this dress on. I came out, and there were five women in the room. I was like, “Okay, this is the first one.”

Everyone was like, “Oh my God!” They didn’t even want to see the other one. They were saying, “This is the one. This is 100% the dress.”

I was like, “Are we sure? Really?” I was actually looking for someone to tell me to put the safe thing on.

Danielle: Nobody was.

Jenn : Nobody was. I was like, “Damn it. I guess this is what I’m wearing.”

Danielle: Let’s talk about that for a moment, because there’s such a great story here about how you help women and how I talk to women about self-image. It’s so important to have that feeling you had in that dress, while waiting for someone to give you permission to stay with what’s been normal for you. Even as successful as Jen was the moment before that dress, it was still your baseline—what we call in our world the paradigm. It’s the habitual way of showing up that’s getting you your habitual results.

There’s nothing wrong with those results. You’re a multimillionaire. They’re great results. People want them.

And yet, you know there’s a next level for you. Giving you permission to wear that old dress would have been a disservice to you. It would have kept you in that place.

Jenn : For sure. It sounds silly when you talk about it through the lens of, “It’s just a dress,” but for me, putting that dress on meant I was exposed in ways that were physical, too.

Danielle: Yeah, you were.

Jenn : And also, for me, it was, “Can I pull this off?” Can I get up there and stand on the stage and pull this dress off without being judged?

The Fear of Being Judged

Jenn : That was the thing in the back of my head. Am I going to be judged for coming out in this? Meanwhile, I teach in a sports bra and tight pants for a living! It’s so crazy to be able to hold both of these things at the same time. They all felt like truth to me in that moment.

I could witness it. I was like, “Oh my God, this is so wild, how much my safety net is wanting to pull me back to just stay safe and get on that stage.” At the same time, there’s this new part of me that I really am still not familiar with. I feel like I don’t really know her. I feel like there’s this alter ego that has come forward.

She won the battle that day by getting me on stage in that dress. But I’ll tell you, I was sent the recording of the talk a month ago, and I’ve still not listened to it. I keep saying to myself, “I’m going to wait until I have a moment where I can really be present with it and listen.” But that’s not actually true. There’s something else going on.

I’m super honest about it, and it’s wild to me because I am very audacious in my life. I’m bold. I have a lot of courage. I’m not afraid to say a thing. I cut through BS all the time, and I’m really proud of that part of me.

But there’s this visibility piece of owning that on a different level. It’s not just about helping more women. It’s about owning it for myself. That feels a little too ostentatious, a little too audacious.

Honestly, it has been the most wild trip to witness this struggle. I have women like you and Adele in my life, and all these very powerful women who live in that energy of the universal laws and the stories we make up for ourselves. I’m so well-versed in all of it. At the same time, very deeply, there’s a piece of me that feels like, “Do not rush your arrival. Do not rush how this is going to unfold for you.”

I took the entire month of August off to finish writing my book, The Audacious Woman. I say the book actually wrote me. I handed my manuscript in last week. When I handed it in, I told them, “It’s not 100% done, but I have to give it to you and get it out of my hands and my soul right now so I can have a minute.”

I asked them to send me back the first draft of edits, and I’m going to trust that, at that time, the pieces that need to be added will be ready to write. It’s been interesting.

Danielle: Let’s go to the book in a minute. I want to go back to you going on stage in that dress and how this part of you won that day. You said it yourself, and I’m always talking to my clients about this: it’s almost like there’s a secret scoreboard that only you can see. Your paradigm or your future self—only one of you can win.

The paradigm version, or the habitual version of you, is always going to want to pull you back into safety, and it will have all the good reasons, right? There’s an obvious difference we can bring to the table through the dress, the way you speak, and the way you upgrade yourself. But the key is, to your point, how do you be her now in the everyday things? What are the micro-movements in your thoughts, feelings, and physical self that represent the woman who was on stage in that pink dress? That audacious upgrade. How do we bring her into your everyday life?

Whether you’re in a robe writing your book, interacting with your family, or going to the grocery store, what changes? That’s where the real thinking work comes in. Yes, we can all do it on those stages, but then it takes time. If you’re conscious about the upgrades that happen in day-to-day life, the reality is that your next-level version, with next-level impact and next-level income, is still doing many of the same things.

Jenn : Yeah, like driving your kids places and perhaps going grocery shopping. I learned this from my ex. One of the best things he gave me, outside of my daughter, was this: he was an actor, and I witnessed him embody new characters often. He would practice a monologue in a new accent. That’s kind of like being on stage, the obvious example.

But I watched him once at the fridge. He had a different posture, and he was opening the fridge. I’m watching from the outskirts of the kitchen, thinking, “What is he doing? What’s happening here?”

He was practicing a new character, noticing that even something as simple as opening the fridge needed to be more regal. It wasn’t El’s dad opening the fridge. It was this character.

Why a New Identity Needs a New Script

Danielle: You’ve said this before, and hearing you talk about it this way, I’m thinking, this is it. It’s about needing a new script. When you’re learning a new script, you have to read it, practice it, and rehearse it until you start to embody it.

Jenn : For me, I feel like I auditioned for a role thinking, “I’m just going to go up there for shits and giggles.” Then I got the role. Now it’s like, okay, you got the part. We can’t tell you when filming starts or any of that. We also don’t have a script, but just stay in that character state.

And I’m over here thinking, “I need a script. I’m a Virgo. Give me a list. Give me something to do.”

It’s been interesting, a little bit of this energy of floundering. When I was writing my book, The Audacious Woman, it was really about this convergence of body, business, and life. How you do one thing is how you do everything, and how you show up is how and who you’re going to be in everything you do. Part of our conditioning is that we’ve been taught to segment the parts of ourselves, compartmentalize, break everything apart, and treat everything as though it’s different. That’s where the struggle comes from.

In reality, it’s all the same. The person you are is the person building the family, building the business, taking care of the body, and being the person you are out in the world. Writing this book and going deep, sharing all these different points in life, didn’t feel like I was writing a script. It felt like I was creating a memoir.

I also wanted it to have the same energy as when women came up to me after that talk and shared their experiences, and the messages I’m still getting two months later. That’s what I want this book to feel like. I want you to read something and go, “Oh my God, she has just articulated and explained something I’ve experienced in a way that I myself wasn’t able to put into words until right now.” I’m just sitting in an interesting place.

Danielle: It’s a great place. I will also say, and this is the show to say it on, it’s wild how you’ve witnessed yourself go through these upgrades. It feels like you’ve turned the faucet on full. There’s more intensity, but you can simultaneously witness yourself almost panic that it’s coming out too fast, and you go and shut it off.

Jenn : Yeah. Part of how I had to manage what that felt like in the moment was to go in and say, “I just have to shut this off for a little bit. I need to take a breath.”

Danielle: It’s about calibrating to the new energy and helping yourself feel safe again in that new place, because the event at Pink Skirt changed you. It couldn’t not have.

Jenn : Yes.

Danielle: So then it’s, “Okay, how can I feel safe being seen like that?” And that takes a moment because you literally expanded, pulled the elastic band back, and went, “What?” Now it’s like, “Okay, I’m going to sit there for a minute.”

Jenn : Yeah. Yeah. It’s so good.

Danielle: I’m proud of you.

Jenn : Thank you.

Danielle: We get to share the stage in November. I’m so excited about that.

Jenn : In two months. My flight is two months from today.

Danielle: And so you have me thinking about outfits.

Jenn : Trust me, no one’s going to be thinking more about their outfit than me now!

Danielle: Oh my gosh. So good. Okay, talk to me about The Audacious Woman. You’ve shared about the book. Tell me about the program.

Inside The Audacious Woman Mentorship

Jenn : What the program was on the morning of Pink Skirt and what it became the second I stepped off the stage are different now. The Audacious Woman is really about, first and foremost, understanding you—the woman who is at the root system of everything you’re building and creating. So many of us believe the reason our business isn’t working or the money isn’t coming is because we don’t have the right strategy, the right prompts, or the right team members. Sometimes that’s true, but you have to bring it back to the person who is at the helm of all of this.

The first three months of mentorship are spent understanding who you are and why you’re doing what you’re doing. Why does this matter to you? In business and in life, when things hit the fan, that end goal, that dreamy vision, better be something you’re wildly connected to. You need to know why you’re doing this. Otherwise, you’re going to oscillate. One day you’re going to love it, and one day you’re going to want to burn it down. Then you’ll love it again, and want to burn it down again.

That’s exhausting. I spend the first season helping these women get clear and focused on themselves, their offer, their business, and all of that. We build the root system. In the months that follow, we go deeper into some of the assets a business requires and some of the more linear pieces.

We also talk a lot about how we’re individually designed to run businesses, create offers, make money, and all of that. It’s always so fun because women come in at the beginning with a business plan and a vision for themselves, and it ends up being more of a personal development journey, as business often is. By the end, there’s a lot more clarity, but there’s also a lot more honesty. The thing I’m most proud of is graduating women from this mentorship who are now building a business they really want to build. Not the one they think they’re supposed to build, not the one that got them to a certain point, but the one they actually care about and feel lit up by.

That has been me at so many points. Our million-dollar program, which I built and ran for eight consecutive years, reached a point where I was still passionate about what I was teaching. I still loved the work we were creating and the transformation. But I came to a point where I thought, “That chapter is done for that version of me. I’ve completed what I desired to do, and I don’t have the same energy and frequency about it anymore.”

For me, that means I’m going to sunset that program so I can build a different version of something that I’m super lit up about in this moment. If I look back over 30 years of my business, every business has cycles and seasons. I have a lot of rhythm. I build something, I’m super proud of it, I create the impact and the imprint, and then I go, “Okay, my work here is done,” and move on.

Danielle: That’s such a great permission slip for everyone listening. Let’s bring in a little bit of the laws. The law of the vacuum of prosperity states that it’s important to let go of something of a lower nature that’s no longer resonating, so something of a higher nature can move in. It can’t move in if the other thing is in the way.

I’m not saying this means starting and stopping a million different things at once. You talked about this at the beginning: people stop right before the payday.

Jenn : I’m birthed off of complete.

Danielle: Exactly, and putting in the work to create that completion.

Jenn : You have to give yourself permission to do it at least one time, because doing it that one time allows you to start collapsing time. Doing it again is where you build on that. If you never complete something and you just business-hop and program-hop, you never create a foundation for anything to stick and grow from. I think you learn from that time, bring that learning into the next thing, and constantly adapt.

Danielle: Yeah. You said something else. The law of the vacuum of prosperity was there, and then there’s rhythm, or the seasons of business. That’s super important for us to understand, just like the seasons our bodies give us as women.

Your Cycle and the Seasons of Business

Danielle: One thing we didn’t talk about, which we touched on behind the scenes, was how you haven’t fully noticed the growth within yourself. I’m curious about that.

Jenn : A little bit less so now. When I hear myself talk about it, I’m like, “Oh, there you are!” Yes, there has been growth. But I still feel like there’s work to do. There’s that piece you talk about that I know I’m not necessarily doing.

At the same time, being audacious isn’t always about standing in a pink dress that’s very revealing. I think I have a lot of subtle audacious qualities about me. Part of learning how to move through the day and follow a different script is recognizing the subtle ways I am an audacious woman in everything I do. It isn’t always going to be these outward, obvious ways.

Danielle: I think of the Karate Kid movie: wax on, wax off. How is that version of you who was in the pink dress practicing audacity every day in the micro-moments, at a level you haven’t before?

Jenn : That’s a good question. I think that’s the question, because you’ve always been audacious. So, what is different?

Danielle: Amazing. I’ve got three questions for you that we end every podcast with. The first is: abundance in one word.

Jenn : Liberation.

Danielle: As I was preparing for you to join me today, I wanted to change the question a little because you and I have talked about money before. I wanted to bring it a little more into the money-in-her interface. I was curious about the word you would choose.

Jenn : For me, it’s liberation because I know I’m in abundance when I feel freedom.

Danielle: Yeah. Amazing. The second question is: what’s the one thing you do for yourself in your million- or billionaire-frequency life that is a non-negotiable, selfish thing for Jenn?

Jenn : I go to bed before anyone else in my house. It doesn’t matter if there’s an awesome conversation happening. I go to bed before anyone else in the house, and I take that time for me.

Danielle: You did that on retreat as well.

Jenn : Yeah.

Danielle: Last question. You have one book to read for the rest of your life. Only one book. What book, and why?

Jenn : The Alchemist has always been a favorite for me. I feel like I’m an alchemist at the root of the work that I do.

Danielle: And The Surrender Experiment.

Jenn : Yeah!

Danielle: Look at you, dropping in two. It’s on brand. Amazing. Thank you. I’ve really enjoyed this. I do a lot of different interviews, and you can tell when an interviewer has created a different energetic container to hold the conversation.

Jenn : Thank you. That means a lot, and you mean a lot to me. I appreciate your time.