In this episode of Creating Confidence, Nicole Kalil joins Heather Monahan to discuss the foundations of authentic confidence. Drawing from her experience as a former executive in the finance industry, Kalil shares her transition from struggling with authenticity to becoming what she calls a "Confidence Sherpa," helping others develop genuine self-trust rather than superficial confidence.
The conversation explores how true confidence comes from within rather than from external achievements or validation. Kalil outlines five major obstacles to building confidence, including perfectionism and unhealthy comparison to others, while Monahan adds context through her own experiences with maintaining authenticity in professional settings. Together, they examine practical strategies for developing self-trust, setting healthy boundaries, and embracing individual strengths.

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Nicole Kalil shares her transformative journey from an executive struggling with authenticity to becoming a guide for others seeking confidence. Despite her success as a female executive in the male-dominated finance industry, Kalil found herself grappling with inauthenticity and a lack of true confidence. She often suppressed her natural qualities like empathy and vulnerability to fit into the masculine environment.
Through observing confident individuals and extensive research, Kalil began understanding the distinction between superficial confidence and genuine self-trust. Her transition to mentoring others in confidence-building strategies solidified her own journey and established her role as a "Confidence Sherpa."
Kalil and Heather Monahan challenge common misconceptions about confidence, emphasizing that it stems from self-trust rather than external achievements or others' perceptions. Monahan shares her experience with a property purchase and dismissal from corporate America to illustrate how genuine confidence is an internal state independent of circumstances.
To build authentic confidence, Kalil recommends keeping commitments to oneself, establishing healthy boundaries, and embracing unique strengths rather than imitating others. Monahan reinforces this by sharing how she maintained her authentic style, even wearing ripped jeans for a speech, which ultimately boosted her confidence.
Kalil identifies five major obstacles to confidence:
Monahan supports these points through her own experience, describing how attempting to fit an inauthentic image and relying on job titles for confidence ultimately proved unfulfilling.
1-Page Summary
Nicole Kalil takes us through her introspective journey of overcoming inauthenticity and the facade of confidence, detailing the path that led her to become a "Confidence Sherpa" for others.
Despite ascending to an executive role at a Fortune 100 company in the finance sector, Nicole Kalil felt the pangs of inauthenticity and a deep-seated lack of true confidence. As one of the few women in a predominantly male industry, she faced internal turmoil between trying to meet external expectations and maintaining her sense of self. She noted that this disconnect only fueled her confidence issues.
Early on, Nicole found herself expected to participate in women's events within her field but initially resisted, feeling more compelled to assimilate into the traditional male-dominated environment. This resistance was one of the personal elements that made writing the initial portions of her book particularly challenging, as these chapters forced her to confront and articulate personal experiences and motivations that she typically did not share in her public speaking engagements.
In her struggle to fit in, Nicole grappled with authenticity in her participation in executive meetings. Despite sharing her opinions, she often resorted to a masculine demeanor, suppressing her innate qualities like empathy, transparency, and vulnerability, to mirror the behaviors she thought signified strength and confidence within her industry.
Nicole’s journey into the heart of true confidence began with keen observation.
Nicole scrutinized those around her who exuded confidence in order to understand their essence, yet she also identified underlying insecurities among individuals who were ostensibly successful or high-earning. Through this exploration, she realized the complex nature of confidence, discerning the difference between superficial confidence and deep self-trust.
Her path to self-discovery also ...
Nicole's Personal Journey To Becoming a "Confidence Sherpa"
Nicole Kalil and Heather Monahan challenge the common misconceptions about confidence, asserting that it's not derived from external achievements or others' perceptions but from trusting oneself and embracing authenticity.
Nicole addresses the false notion that confidence is a byproduct of reaching certain milestones or earning approval from others. This understanding is contrasted with Nicole's personal journey of progressing in her career but feeling inauthentic and lacking self-confidence despite external appearances. Heather Monahan shares her story about a property purchase that felt wrong due to an uncomfortable interaction with a realtor, which led to the realization that genuine comfort and confidence are internal states that are not dependent on situational victories or the approval of others.
Nicole Kalil talks about the "confidence con," the misconception that confidence is something one acquires from external sources, such as success or societal approval. Heather Monahan echoes this sentiment by reflecting on her dismissal from corporate America, which made her understand that true confidence is an inward state that cannot be taken away. They suggest that confidence is knowing and doing what one feels they are supposed to be doing, which is an indication of self-assurance, not dictated by external circumstances or momentary feelings.
Nicole Kalil stresses the significance of honoring commitments, not just to others but to oneself. She points out that people often neglect personal commitments, and this undermines self-trust and confidence. Keeping these commitments is a foundational step in building authentic confidence.
Kal ...
Defining and Cultivating Authentic Confidence
Nicole Kalil identifies common obstacles to confidence and shares insight into how these challenges can be addressed to build true self-assuredness.
Nicole Kalil talks about perfectionism, which she frames as the number one confidence derailer. This damaging belief system creates a pressure to always be perfect, which ultimately undermines self-trust. Kalil suggests that striving for flawlessness is an unrealistic goal that hampers confidence.
Kalil defines the second confidence derailer as "head trash," referring to our negative self-talk. She explains that this internal criticism, such as feelings of inadequacy, is usually mean, not true, and certainly not kind. By challenging this self-critical dialogue with kindness, individuals can work towards overcoming this obstacle.
According to Kalil, comparison acts as the third confidence derailer. It involves pitting oneself against others and typically results in comparing one's regular life to someone else's best moments. This unhealthy comparison often leads to feelings of inadequacy and undermines confidence.
The fourth derailer, Kalil mentions, is overthinking, which leads to inaction and regret. She stresses that overthinking prevents us from taking any action, which, over time, individuals regret more than the actions they do take. Kalil shares her own experience of overthinking while writing her book and illustrates the importance of taking action, however imperfect, rather than being paralyzed by analysis.
Common Confidence "Derailers" or Obstacles
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