Unexpected Struggles of Success | RTWOS EP 5 with Jenn Pike – Shamelessly Ambitious Episode 130

Filed in All Episodes, Business Strategy, Emotional Intelligence, Leadership Development, Releasing The Wounds Of Success Series — November 28, 2023

In the pursuit of success, often glamorized and celebrated, there’s a side that is talked about less frequently — the wounds that come with it. That’s why I felt so called to create this series, Releasing the Wounds of Success. In my recent conversation with wellness expert, hormone practitioner, and serial entrepreneur, Jenn Pike, we delved into the uncharted territories of success, the unexpected struggles, and the healing process that is in store for all of us.

Jenn is someone I’ve followed for years after finding her through cycle syncing and learning about hormones and the body. But, I’ve loved being a follower of Jenn’s beyond that because I love everything that she stands for. She brings incredible education to the industry that I find to be so non-negotiable when it comes to women, particularly high achievers, desiring a great deal of success. Jenn is a medical exercise specialist and functional diagnostic nutritionist specializing in women’s health and hormones, but she’s also a best selling author of three separate books: Simplicity Project, Simplicity Kitchen, and Simplicity Body. She really is an incredibly fiercely driven founder and audacious woman and I know you’ll resonate with her story. Connect with Jenn on Instagram, her podcasts: The Simplicity Sessions & The Audacious Woman, and find more on her website!

The Pressure of Seven Figures

Jenn shared a pivotal moment when the “seven-figure title” became attached to her. The narrative shifted from the joy of the pursuit to the pressure of meeting expectations. The realization struck hard — this journey was starting to feel less like her own and more like an obligation dictated by the industry and specific mentors. 

“At what point is it enough? We’re constantly chasing after those numbers and metrics and at what point do we then start outsourcing our own knowing of what feels sustainable for the sake of doubling it… tripling it… hitting the next milestone and whatever that may be?”

Months into this high-stakes pursuit, she took a bold step of parting ways with her business mentor. The reason? The advice the mentor was giving Jenn didn’t align with her core values, and it felt like she was sacrificing her well-being for external measures of success.

“All of a sudden when this seven figure label got attached to me, now it was like, ‘well, it doesn’t matter if this is fun, this is what we have to do in order to get to the end goal.’ So a couple months into trying to do that, I actually parted ways with the business mentor I had at the time because I was like, ‘this is your journey. It is not mine. This does not feel good.’ My body was starting to feel panic because all I kept going back to was that this meant more work and less time with my family and myself. This is going to put me back in that place where I spent four days on the couch and complete burnout and was ready to go be a cashier.

I was just like, I can’t do this anymore. Actually, when I started to get more and more successful, my nervous system completely triggered a level of PTSD in me.”

Triggering Past Trauma

As achievements piled up, panic set in. Jenn’s experience is extremely common & something we probably don’t talk about enough when it comes to building a successful business. The fear of more work, less time for family, and the return to burnout-induced couch days was looming. She had multiple external voices urging her to push harder and do better, or risk failure. Even after building her business from the ground up to $1M, people told her if she pulled back, she’d be failing not only herself, but her team, too.

Defining Success on Her Terms

That’s when she decided she needed to put a hard stop on the way she was doing things. No more conformity to external expectations. This was her life, her company, and her team. She had built a million-dollar business without relying on any ads or external funding. Jenn’s journey to success had started seven years ago, but it took nine months to reach the million-dollar milestone. The business model that was once scaling was now all about doing it at her pace and building something sustainable.

The Price of Success

As we’ve learned throughout this series, success, however, wasn’t without its challenges. The pressure to maintain constant growth was taking a toll in all areas of her life. Success, for her, was not just financial; it was about creating impact across various facets of life — motherhood, relationships, and personal well-being.

Mom Guilt and Leadership Challenges

But during the pursuit of success, Jenn, a mother of two teenagers, opened up about the perpetual struggle with mom guilt. She noted she felt like she was given a budget for all the different roles she carried.

“I’m half assing it as a wife, I’m half assing it as a business owner. And I was like, how do I bring my whole ass into everything that I want to do? It always felt like I was given this amount… this budget, like now, I have to split the funds up and spread myself across all these areas. I really struggled with that for so long cause I always had this guilt of not being good enough.”

The evolving needs of her children, coupled with the demands of leadership, posed challenges. Moments of self-doubt crept in — was she missing crucial life moments due to work commitments? Striking a balance remains an ongoing battle, but Jenn has realized what is truly important to her so she’s restructured her work schedule so she can be more available for her family.

Navigating the Uncomfortable Relationship with Money

As a mom of a 15 & 17 year old, Jenn is changing the narrative her family carried growing up. When relating to money, Jenn’s family instilled the value of always having “enough,” practicing gratitude, and never needing abundance. Yet, as financial success has come Jenn’s way, she’s been met with some uncomfortable money moments. The discomfort of having more than “enough” as an adult led her to resist spending, rooted in the fear that such success might not repeat itself or that she didn’t deserve to have an abundance of money so she ought to give it to someone who needed it. She says that, now, her goal is creating a level of “rebellious wealth.” This means that all of their expenses are paid for, plus a little bit of “F you” money to the world where they get the freedom to invest.

“Anything above and beyond that we are super grateful for, but I will not sacrifice who I am for more money. Ever.”

Embracing Personal Power

The conversation took a poignant turn as Jenn admitted to an ongoing struggle of fully embracing and embodying her audacious self. Judged throughout her life for being intimidating and too powerful (extremely relatable) she found it challenging to consistently project her audacity. The fear of being judged for her character cut deep because while judging someone based on appearance is tough, being judged on your character is harder because that’s who you are to your core. She often found herself retracting to avoid criticism until she realized the importance of spending more time in spaces and energy of women who not only can witness your audacity and boldness, but lovingly accept that part of you and then reciprocate it.

It’s so cliche but so true that “getting in the room” really makes a difference. Whether physical or virtual, surrounding yourself with people who see you for who you really are, where you can be shamelessly ambitious & validated through your journey, is priceless. What we all desire is to feel like we belong, that we are right, and that there is space for us. && there is space for you my friend. The REDEFINE Mastermind is open for applications! While we don’t start until February 2024, I will officially begin looking at applications on December 1, 2023. There are only eight spots for this intimate mastermind, because I truly want to be able to pour as much of myself as I can into you and I want to keep the integrity of the intimacy that I desire inside this mastermind alive. This is a four month experience where we’re not just chasing quick wins — we’re here for the long term. It’s about creating a business that doesn’t constantly need you, where we prioritize human connection, ethics, and emotional wellness. This is therapy for you and your business, because when you’re building something unshakable… It truly starts with the roots.

Finding Healing in Shared Stories

As the conversation unfolded, it became evident that success is not a linear path, but a series of peaks and valleys. Jenn’s openness about the wounds of success and the ongoing healing process resonates with many women navigating similar journeys. In a world often obsessed with constant growth and external validation, Jenn’s story serves as a testament to the importance of defining success on your own terms and embracing the power within.

This conversation with Jenn offers a raw and authentic look at the complexities of success. It’s a reminder that behind every achievement lies a personal journey, complete with struggles, vulnerabilities, and ongoing self-discovery. In sharing her story, Jenn empowers others to embrace their unique paths and find strength in vulnerability.


This series is equipped with an additional email that goes along with each podcast episode that gets a little bit deeper with additional therapeutic action steps so you can release your wounds, too.


The Hybrid-Mastermind Experience where tailored business strategies get a therapeutic edge — pairing emotional wellness with a customized approach that meets you where you’re at and takes you where you’re going. Applications are open now to WAITLIST members only. It’s not too late to jump on the waitlist for yourself: JOIN NOW.


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I am the definition of duality—I swear like a sailor and break rules like it’s my job, but I also hold incredible space for my clients and work my ass off to help them achieve the success they’re after (but faster).

My background in counseling and my experience founding three multi-6-figure businesses gives me a unique perspective on what it means to show up and serve as an ethical and successful CEO. Leaning on my experiences, along with the experiences of the hundreds of women I’ve been honored to work with, I offer founders a psych-backed and human-first approach to scaling their legacies—both in and out of the office. 

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