Breaking Free: Jennifer Thompson on Silencing Self-Doubt and Redefining Success

  • Published on:
    October 23, 2024
  • Reading time by:
    4 minutes
Breaking Free: Jennifer Thompson on Silencing Self-Doubt and Redefining Success

Meet Jennifer Thompson, the dynamic force behind If We’re Being Honest: Silencing the Lies We Tell Ourselves to Live a Life We Love, a breakout bestseller that’s empowering women to redefine their success and embrace their true potential. As a mother, entrepreneur, and marketing manager with over 17 years of experience at Fortune 100 and 500 companies, Jennifer has spent her career navigating the pressures of perfectionism, self-doubt, and societal expectations. Now, she’s on a mission to help other women break free from limiting beliefs and lead lives filled with authenticity and fulfillment.

In this exclusive feature for Women on Topp, Jennifer shares the deeply personal journey that inspired her book, the challenges she’s faced as a woman in leadership, and the powerful strategies she’s developed to help others silence the inner critic and step into their own greatness. Her story is one of resilience, transformation, and the courage to embrace vulnerability—reminding us all that success isn’t about external validation, but about living a life that’s true to who we are.

Can you share the key inspiration behind your book, If We’re Being Honest, and how it relates to your experiences as a marketing manager in Fortune 100 and 500 companies?

The inspiration behind If We’re Being Honest is deeply rooted in my personal journey of challenging the lies we tell ourselves and confronting societal expectations that shape our identities. As a marketing specialist and now manager in Fortune 100 and 500 companies, I frequently found myself wrestling with self-doubt and the relentless pursuit of external validation. In a world where success is measured by titles and recognition, I realized how easy it is to lose sight of who you truly are. This experience pushed me to reexamine the lies I had been telling myself about success, motherhood, and life in general, revealing how confining and untrue they really were. I made it my mission to undo every lie I had internalized and break the cycle before it broke me.

If We’re Being Honest serves as a transformative guide for silencing those negative beliefs and stepping into our authentic selves. It parallels my corporate experiences where I navigated challenges and grappled with the need to prove my worth, with the personal struggles that many women face as they balance career ambitions and motherhood amidst societal pressures. The book emphasizes that genuine fulfillment comes from embracing our true selves rather than chasing external expectations.

By sharing my story and the insights I’ve gained throughout my career and motherhood, I aim to empower other women to break free from the constraints of self-doubt and embrace a life filled with purpose and authenticity. Ultimately, the book is a call to action for readers to redefine success on their own terms and lead lives that they genuinely love.

We’re Being Honest Book

What specific challenges have you faced as a woman in leadership roles, and how have those experiences shaped your approach to empowering others?

One of the biggest challenges I’ve faced as a woman in leadership has been navigating environments where I felt the need to prove my worth—both to myself and to others. It wasn’t just about earning a seat at the table; it was about asserting my right to even be in the conversation. Whether facing self-doubt or confronting entrenched, siloed mindsets, these experiences have profoundly shaped me into the leader I am today.

I’d be lying if I didn’t mention that throughout my career I have noticed another critical trend happening within corporate environments: the tendency to promote individuals into leadership roles simply because they excel in their current position. This rush to elevate experts frequently overlooks that leadership demands a different skill set that some simply are not equipped for. It’s not just about how much you know; it’s about how well you can trust others, delegate responsibilities, and empower your team to make decisions. Being an expert does not inherently qualify someone to manage and nurture others, effectively.

Ultimately, leadership success is not measured by individual performance but by the ability to inspire and empower my team. It’s about creating a space for others to thrive, which begins with the understanding that leadership isn’t about control or micromanagement; it’s about trust. Trusting your team to excel in their roles means providing them with the tools, guidance, and support they need to grow.

As a leader, my responsibility is to ensure that my team feels confident, supported, and empowered to achieve their best. When people know they have your backing, they are far more likely to take bold risks, share transformative ideas, and evolve into leaders themselves. Leadership goes beyond giving direction; it’s about fostering an environment of trust, collaboration, and mutual respect. I want my team to understand that their ideas carry weight, their contributions matter, and they are entrusted to lead with independence. I don’t want anyone to have to fight to have their voice heard or worry about their worth when they step into a room, like I did.

When you empower others to make decisions and stand by them when they take risks, you cultivate a resilient and thriving team. This approach not only nurtures growth but also lays the foundation for long-term, sustainable success within any organization.

How do you think marketing strategies need to evolve to better serve women and address their unique challenges and aspirations?

Marketing strategies must evolve by shifting from a one-size-fits-all approach to one that recognizes the nuanced experiences, aspirations, and challenges women face in today’s world. Historically, marketing toward women has leaned heavily on traditional gender roles or superficial empowerment narratives. However, today’s women are multidimensional. We are leaders, entrepreneurs, mothers, and change-makers. This means marketing needs to speak to the whole person, not just one aspect of our lives.

To better serve women, brands must invest in truly understanding women’s evolving roles and values. This means conducting research that goes beyond surface-level demographics and taps into the emotional, mental, and societal complexities that shape the modern woman’s experiences. It’s about acknowledging and addressing the real challenges women face—whether it’s the balance of career and family, the pursuit of authenticity, or overcoming imposter syndrome.

Effective marketing needs to center on authenticity, empowerment, and inclusivity. Instead of pushing products or ideals, brands should focus on fostering genuine connections and supporting women where they are today in ways that align with their goals. Marketing that embraces women’s full spectrum of ambitions and challenges while providing them with real value, support, and solutions will ultimately create deeper loyalty and trust.

What role does authenticity play in effective leadership, and how can women leaders cultivate this quality within their teams?

Authenticity in leadership has always been a double-edged sword for women. Historically, we’ve been labeled as “too emotional,” a critique that was often weaponized to undermine our credibility in professional environments. But things are shifting; what was once viewed as a weakness is becoming one of the most sought-after qualities in leaders. People no longer want perfection or detached authority—they want someone who is real, relatable, and transparent.

Authenticity builds trust. When leaders are open about their experiences, challenges, and emotions, it creates an environment where others feel safe to do the same. For women, this means owning our emotional intelligence, rather than downplaying it. Emotional awareness is a powerful asset that fosters deeper connections, greater collaboration, and more innovative problem-solving within teams.

To cultivate authenticity, women leaders need to lead by example. This means showing up as our true selves, unafraid to admit when we don’t have all the answers or when we’re navigating difficult decisions. It’s about creating spaces where vulnerability is valued, not punished. Encouraging team members to bring their whole selves to the table without fear of judgment leads to more engaged, empowered, and fulfilled teams.

At the end of the day, authenticity isn’t just a leadership strategy, it’s the key to sustainable, transformative leadership. It creates a ripple effect. When we lead authentically, we give others permission to do the same, creating teams and cultures where everyone feels seen, heard, and valued. And in a world that’s hungry for realness, authenticity is no longer optional—it’s essential.

What are some of your favorite books or resources that have inspired you on your journey, and why?

As a writer, you know I love a good book. Quite honestly, books are the cheapest therapy money can buy. I owe much of my growth to so many brave, powerful women who went before me – but when specifically talking about my journey there are a few books that stand out. These authors and their research, as well as their stories, have profoundly shaped my understanding of leadership, self-transformation, and motherhood. One of the most impactful is Daring Greatly by Brené Brown. Her exploration of vulnerability and courage speaks directly to the heart of authentic leadership, reminding me that real strength comes from embracing our imperfections and showing up as our true selves. This message has influenced not only how I lead but also how I encourage others to do the same.

Untamed by Glennon Doyle has been another powerful influence, particularly in its unapologetic call to break free from societal expectations and discover the woman you were always meant to be before you were caged. It deeply aligns with my belief that women can reclaim their power by shedding imposed narratives and stepping boldly into their authentic selves.

The Radical Awakening by Dr. Shefali added yet another layer of understanding. Her book delves into the spiritual and emotional awakening that many women face, helping me see how transformation often requires confronting long-held beliefs about ourselves and the world around us.

Lastly, Fierce, Free, and Full of Fire by Jen Hatmaker has inspired me to be unapologetically bold in both my personal and professional life. Hatmaker’s work celebrates living authentically and empowers women to claim their space with confidence.

These resources have equipped me with the insights to not only guide myself but also to mentor other women on their own journeys of self-discovery and transformation. I wholeheartedly recommend these books to anyone looking to break free from limitations and embrace their truest, most powerful selves.

Can you share a moment of vulnerability from your life that significantly changed your perspective on success and fulfillment?

One of the most pivotal moments in my life was when I found myself sitting alone in my car, in a Costco parking lot, tears streaming down my face. I had been relentlessly chasing success—working hard to climb the corporate ladder, meet the expectations of others, and balance the never-ending demands of motherhood. But in that moment, it all came crashing down. I had spent so long trying to be everything to everyone that I had lost sight of who I truly was.

That moment was a breaking point, but it was also a breakthrough. I realized that success isn’t about external achievements; it’s about inner alignment. It’s about living a life that’s true to who you are, not one that conforms to societal definitions of worth. I had to redefine what fulfillment meant for me; not as a mother, not as a career woman, but as me. That shift in perspective changed everything.

From then on, I stopped striving for validation from others and started pursuing what genuinely brought me joy and fulfillment. This lesson has deeply influenced how I lead and mentor others. I now encourage people to seek alignment with their inner values and aspirations rather than constantly chasing external approval. True success comes from within—it’s about being honest with yourself and creating a life that reflects your authentic desires, not the expectations placed upon you.

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