Learning how to build confidence often begins with understanding why we lose faith in ourselves in the first place. We tend to associate confidence with achievement, assuming that success will eventually silence our doubts and give us the certainty we need to pursue bigger opportunities. Yet even accomplished people can find themselves questioning their abilities when they enter unfamiliar territory, experience rejection, or spend years in an environment that gradually erodes their sense of worth. Confidence, as Heather Monahan explains, develops through the choices we make when uncertainty is still present.
In this episode of Passion Struck, I sit down with Heather Monahan, entrepreneur, keynote speaker, and bestselling author of Confidence Creator and Overcome Your Villains. After building an impressive career in media and rising to the C-suite as a chief revenue officer, Heather experienced an unexpected firing that forced her to reconsider her identity, her professional future, and what she wanted from the next chapter of her life. Her story offers a valuable perspective on career resilience because it reveals how the experiences that unsettle our confidence can also help us discover the beliefs and habits that have been limiting us.
Our conversation explores the relationship between confidence, environment, personal agency, and the courage to act before we feel entirely ready. Heather shares how she learned to recognize toxic workplace dynamics, why she believes you should never take a no from someone who cannot give you a yes, and how small actions can gradually change the way you see yourself. Her experiences invite us to examine a deeper question: how much of our perceived potential reflects our actual abilities, and how much has been shaped by the people, situations, and stories we have learned to accept?
Why Successful People Still Struggle With Self-Doubt
One of the most revealing aspects of confidence is that achievement does not necessarily eliminate insecurity. Heather describes how she struggled with self-doubt and imposter syndrome early in life, particularly while attending a prestigious school on a scholarship. Surrounded by students from wealthier backgrounds, she carried a persistent concern that she needed to prove she was worthy of being there. She responded by pushing herself to excel in sports, leadership, and speaking, hoping that performance would provide the reassurance she could not yet find within herself.
Years later, returning to that same school with her son gave Heather an unexpected opportunity to reconsider those memories. Having traveled internationally and built a successful career, she saw the environment through a different lens. The school seemed smaller, and the insecurity she had once associated with it became easier to understand. She recognized that her younger self had interpreted the setting through shame and self-doubt, creating an internal experience that was far more intimidating than the place itself.
This realization offers an important lesson about overcoming imposter syndrome. Our perceptions are shaped by the meaning we attach to our experiences, and those interpretations can remain influential long after the original circumstances have changed. We may continue to approach a new opportunity as though we are still the inexperienced person who once struggled to belong. Rebuilding confidence requires us to recognize when an old narrative is influencing a present decision and to consider whether our current abilities, experiences, and circumstances support that narrative.
Self-belief develops as we accumulate evidence that challenges the assumptions we have carried about ourselves. Each difficult conversation we handle, responsibility we accept, or unfamiliar situation we navigate can help us develop a more accurate understanding of our capabilities. The goal is to build a relationship with ourselves that can accommodate uncertainty while still allowing us to move forward.
How Your Environment Shapes Your Confidence
Confidence is often treated as an individual quality, something we either possess or need to develop through greater discipline. Heather’s experiences reveal another dimension: the environments we inhabit can either reinforce our strengths or make it increasingly difficult to access them. The people around us influence what we consider possible, how we interpret setbacks, and whether we feel encouraged to pursue growth.
Heather illustrates this idea through a comparison between running alone and running alongside accomplished athletes in Miami, where she lives. When she runs alone, distractions can make it tempting to abandon a goal before completing it. When she joins the larger community of runners around her, their persistence changes the experience. Even when the weather becomes difficult, seeing other people continue encourages her to do the same. Their example makes sustained effort feel more natural and creates a shared standard that helps her remain committed.
The same dynamic can operate in professional life. Colleagues who challenge our thinking, recognize our contributions, and encourage us to take on greater responsibility can expand our sense of what we are capable of accomplishing. By contrast, an environment characterized by exclusion, disrespect, or constant uncertainty can gradually narrow our ambitions. Over time, we may begin to confuse our diminished confidence with diminished ability, even when the underlying problem is the environment in which we are trying to perform.
This distinction matters because resilience is not simply a matter of enduring difficult circumstances indefinitely. Persistence is valuable when it helps us work toward something meaningful, but it becomes costly when we use it to justify remaining in situations that consistently undermine our well-being or potential. Sometimes the most productive way to strengthen confidence is to seek relationships and environments that allow our abilities to develop.
In this episode, you’ll learn
- Why self-doubt can persist even when you have the skills and experience to succeed, and how to recognize the assumptions that keep you playing small.
- How your environment influences confidence, ambition, and the standards you set for yourself.
- Why you should never take a no from someone who cannot give you a yes, and how Heather learned to advocate for her own value.
- How toxic workplace dynamics can gradually undermine your confidence, and why ignoring harmful behavior can make the situation worse.
- How to build confidence through small, uncomfortable actions that help you develop evidence of your own capabilities.
- How journaling, personal boundaries, and a willingness to change your circumstances can help you reclaim your agency and move toward a more fulfilling life.
What to Do When a Toxic Workplace Undermines Your Worth
Heather’s career provides a particularly instructive example of how toxic workplace dynamics can develop gradually. During her time in a senior media role, she describes experiencing exclusion and disrespect from a powerful colleague. Meetings were arranged without her, her contributions were disregarded, and professional opportunities became entangled in interpersonal conflict. Heather initially concentrated on delivering results and hoped that strong performance would eventually make the situation manageable.
Over time, however, the consequences became difficult to ignore. She describes losing sleep and experiencing physical signs of stress while continuing to work in an environment that had become increasingly unhealthy. The experience helped her recognize a pattern that many high performers encounter: when someone takes pride in their ability to deliver results, they may respond to mistreatment by working harder, believing that exceptional performance will eventually resolve a problem rooted in relationships and power.
Heather expresses the lesson directly: “The problem is bad behaviour doesn’t go away when you ignore it; you amplify it.” In her experience, remaining silent allowed the behavior to continue and influenced how others treated her. The longer she tolerated the situation, the more difficult it became to maintain the confident, capable version of herself she knew she could be.
This insight is especially important for people who have built their identity around being dependable, adaptable, or easy to work with. Those qualities can become liabilities when they lead us to absorb every inconvenience and avoid every difficult conversation. Professional maturity includes the ability to distinguish between the ordinary friction of collaboration and a recurring pattern of behavior that undermines respect, accountability, or psychological safety.
Heather eventually created a deliberate plan to rebuild her confidence. She revisited an image of herself at a time when she felt particularly strong, established daily actions, and developed a playlist to help prepare herself before difficult meetings. These steps helped her reconnect with her own sense of identity and begin responding to the situation differently. Her experience demonstrates that rebuilding confidence often requires both internal work and external decisions. Personal practices can help us regain clarity, while boundaries and changes to our circumstances determine whether that clarity can be sustained.
Why You Should Never Take a No From Someone Who Can’t Give You a Yes
One of Heather’s most memorable career lessons emerged when she decided to advocate for a larger role within a broadcasting company. After delivering strong results, she approached the company president with a proposal to create a vice president of sales position overseeing the broader organization. He declined, explaining that she was doing excellent work in her existing role and that the company did not need the proposed change.
Heather took the response seriously, but she also trusted her assessment of her own value. Rather than accepting the rejection as a definitive judgment of her potential, she began exploring opportunities elsewhere. She identified a more substantial position with another broadcaster and decided to give her current employer one more opportunity to reconsider before she resigned.
When Heather raised the proposal again, the president initially repeated his refusal. She then told him she was resigning. He asked her to wait, stepped away to make a phone call, and returned with a different answer: the company wanted her to take the vice president of sales role. Heather later learned that he had needed approval from his father, who held the authority to make the decision.
The experience taught her a principle she continues to share: “Never take a no from someone who can’t give you a yes.”
The deeper lesson concerns the difference between rejection and authority. When someone declines a request, we often assume their response represents the final verdict on our abilities, our ideas, or the opportunities available to us. Yet that person may have limited decision-making power, incomplete information, or constraints that have little to do with our worth. Understanding who can actually make a decision allows us to respond strategically instead of interpreting every refusal as a personal judgment.
Heather’s story also highlights the importance of advocating for yourself with evidence and intention. She had demonstrated her value through results, identified a role that matched her capabilities, and communicated what she wanted directly. Her confidence did not guarantee that the outcome would go her way, but it allowed her to pursue an opportunity rather than remain dependent on someone else’s recognition.
This principle applies well beyond corporate leadership. Whether you are negotiating compensation, proposing a new project, pursuing a partnership, or asking for greater responsibility, it is worth understanding how decisions are made and who has the authority to make them. Sometimes progress requires a stronger proposal. Sometimes it requires a different conversation. And sometimes the most constructive response is to take your capabilities somewhere they can be recognized and put to better use.
The Confidence Lessons Behind Heather Monahan’s Books
When Heather Monahan reflects on her career, the story that emerges is shaped by several moments when the direction of her life changed before she could fully understand what those changes would mean. Early jobs taught her how to sell, follow through, and build relationships. Unexpected opportunities helped her discover that a disadvantage could become a source of distinction. Later, a difficult corporate experience challenged the confidence she had developed over decades and forced her to reconsider how much of her identity had become tied to professional achievement.
Those experiences provide the foundation for her books, Confidence Creator and Overcome Your Villains. In Confidence Creator, Heather explores how confidence develops through action, repetition, and the willingness to pursue opportunities before we feel entirely prepared. Her account of appearing on the Elvis Duran show captures this philosophy in a particularly human way. She made mistakes during an intimidating experience, but she also completed it, learned from it, and added another piece of evidence to the growing belief that she could handle difficult situations.
The lesson becomes more significant when we consider how confidence is often misunderstood. From the outside, an accomplished person may appear naturally assured, and their visible achievements can make the path toward those achievements seem almost effortless. Heather’s experience reveals the smaller decisions that rarely make it into a success story: the uncomfortable conversations, the nights of uncertainty, the willingness to try again, and the gradual process of learning to trust one’s judgment.
Overcome Your Villains extends this reflection to the internal narratives and external relationships that can keep people from becoming who they want to be. Heather’s experience with workplace toxicity helped her recognize how easily someone can normalize disrespect while concentrating on performance. Her eventual decision to examine her own responses and establish stronger boundaries gave her a way to reclaim her agency and reconsider which relationships deserved a place in her life.
Together, these books offer a connected perspective on personal growth. Confidence develops when we take meaningful action and learn from the result, while boundaries help protect the conditions that allow that confidence to grow. Both require a willingness to examine familiar patterns and make choices that may feel uncomfortable in the moment. Heather’s story is a reminder that a difficult chapter can become a source of insight when we use it to understand ourselves more clearly and make more intentional decisions about what comes next.
How to Build Confidence Through Small Actions
Heather’s approach to confidence begins with a deceptively simple idea: confidence grows through action. Many people wait until they feel prepared, assured, or free from anxiety before pursuing something important. That approach can create a frustrating cycle because confidence often develops through the very experiences we postpone until we feel confident enough to attempt them.
Heather describes confidence as something we are either creating or chipping away at in any given moment. The decisions we make around uncertainty gradually shape our expectations of ourselves. When we repeatedly avoid situations that matter to us, we may reinforce the belief that we are unable to handle them. When we take manageable steps into unfamiliar territory, we give ourselves opportunities to develop competence and gather evidence that we can cope with discomfort.
Her experience appearing on the Elvis Duran radio show illustrates this process. After leaving the media industry, Heather was rebuilding her career and facing a future that remained uncertain. The opportunity to appear on a major radio show was intimidating, and the experience did not unfold perfectly. Her phone vibrated during the broadcast, prompting a lighthearted moment in which she had to acknowledge the mistake. Yet she had shown up, navigated the experience, and completed something that had previously felt daunting. She recorded the experience as a win in her confidence-building journal.
That detail reveals an important shift in how we measure progress. If success means performing flawlessly, every mistake becomes evidence against us. If success also includes taking a meaningful step despite fear, then an imperfect experience can still strengthen our confidence. We learn that we can tolerate embarrassment, adjust to unexpected circumstances, and continue moving toward our goals without requiring every attempt to validate our abilities.
Heather recommends tracking these moments rather than allowing them to disappear from memory. A journal of difficult actions completed, problems handled, and experiences survived can help counter the tendency to remember failures more vividly than progress. Over time, these records provide a more balanced picture of our capabilities and make the next challenge easier to approach.
Building self-confidence through small actions is particularly valuable when a goal feels overwhelming. A person who wants to become a stronger public speaker might begin by contributing to a meeting, then presenting to a small group, and eventually addressing a larger audience. Someone considering a career change might start by contacting people in the field, researching opportunities, or developing a new skill. Each step creates information, experience, and momentum.
The objective is to develop a pattern of acting in alignment with what matters to us, even when uncertainty remains. Confidence becomes more durable when it is grounded in lived experience rather than dependent on reassurance or perfect outcomes.
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About Today’s Guest, Heather Monahan
Heather Monahan is an entrepreneur, keynote speaker, and bestselling author known for her work on confidence, leadership, and overcoming professional and personal obstacles. Her career in media culminated in a chief revenue officer role, following years of experience in sales, revenue generation, and business leadership. After an unexpected firing forced her to rethink her professional future, she rebuilt her career and developed a broader platform focused on helping people recognize their value, strengthen their confidence, and navigate difficult environments.
She is the author of Confidence Creator and Overcome Your Villains, books that explore the relationship between self-belief, deliberate action, personal boundaries, and the courage to create a new path. Through her speaking, writing, and entrepreneurial work, Heather shares practical lessons drawn from her own experiences with career setbacks, resilience, and personal reinvention.
Why Should You Never Take a No From Someone Who Can’t Say YES? | Heather Monahan
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👉 All episode links, my books You Matter, Luma, and The Mattering Effect, The Ignited Life newsletter, and the Start Mattering store are here: linktr.ee/John_R_Miles
FAQ (Frequently Asked Questions)
How to build confidence when you feel insecure?
Confidence can grow through small, deliberate actions that help you develop experience and trust in your own abilities. Start with a manageable challenge, such as speaking up in a meeting, asking a direct question, or pursuing an opportunity you have been postponing. Record what you learn from each experience so that your understanding of yourself reflects actual progress rather than only your fears.
Can a toxic work environment damage your confidence?
A persistently unhealthy work environment can undermine confidence by exposing someone to exclusion, disrespect, inconsistent expectations, or repeated challenges to their credibility. Over time, these experiences may influence how a person evaluates their abilities and approaches new opportunities. Recognizing the pattern, seeking appropriate support, and establishing boundaries can help clarify what needs to change.
How do you know when it is time to leave a job?
It may be time to consider leaving when a workplace consistently harms your well-being, limits your development, or requires you to tolerate disrespect without a realistic path toward improvement. Before making a decision, assess your financial and professional circumstances, explore available alternatives, and consider whether a conversation or internal change could resolve the problem. The important step is to recognize that your current position is one part of your career, not a complete definition of your future.
What are some small daily habits that build self-confidence?
Useful habits include setting achievable goals, following through on commitments to yourself, recording moments of progress, asking for feedback, and practicing conversations that you would otherwise avoid. These actions help you develop evidence that you can learn and respond effectively to challenges. Over time, repeated experiences can make difficult situations feel more manageable.
How can journaling help you overcome self-doubt?
Journaling creates space to examine the beliefs and interpretations that influence your behavior. You can use it to identify recurring fears, distinguish facts from assumptions, record successful experiences, and reflect on relationships that affect your confidence. This process can make patterns easier to recognize and help you decide which actions or boundaries would support meaningful change.
Why should you never take a no from someone who can’t give you a yes?
Heather Monahan learned this lesson when a company president initially rejected her proposal for a larger role, only for the decision to change after he consulted the person with final authority. The experience showed her why it is important to understand who can actually make a decision. A refusal may reflect limited authority or organizational constraints rather than a final judgment of your potential, so identifying the appropriate decision-maker can help you advocate for yourself more effectively.
