In this episode of Creating Confidence with Heather Monahan, Heather addresses the common trap of waiting for perfect conditions before taking action. She argues that analysis paralysis and perfectionism serve as fear-based excuses that prevent progress, emphasizing instead the value of imperfect, immediate action. Through personal examples—from launching her podcast amid chaos to securing interviews with high-profile figures—she demonstrates how messy progress creates opportunities that never materialize while waiting.
Heather also shares her approach to building professional relationships through generosity and value creation, explaining how leading with "How can I help you?" opens doors. She discusses the persistence required to reach ambitious goals, including her years-long effort to connect with Gary Vaynerchuk and the strategic adaptability that led to interviewing Jesse Itzler. Throughout, she illustrates how vision, patience, and continued effort lay foundations for unexpected breakthroughs, like when her TEDx Talk reached Dr. Phil's producer years after its initial release.

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Heather Monahan urges people to take action now instead of waiting for perfect conditions. She observes that many individuals fall into analysis paralysis, endlessly waiting for the "right" moment to pursue their goals, which only stalls progress and serves as an excuse driven by fear.
Monahan describes how the desire for perfection causes people to freeze, wanting everything—the timing, circumstances, and market—to align perfectly before moving forward. She labels these as excuses, arguing that perfectionism blocks action and keeps people from achieving their dreams. Instead, she insists that imperfect action is far preferable to inaction. Sharing personal stories about launching a podcast or traveling to the Dr. Phil show despite chaos, she emphasizes: "Done will always be better than perfect." Real, messy efforts yield growth and produce unexpected opportunities that would never surface while waiting. Monahan explains that "imperfect real work is more valuable than perfect imaginary work."
Monahan discusses how fear of the unknown keeps people from living authentically and reaching their full potential. She recalls remaining in an unfulfilling job for over a decade because she was afraid to make the leap without knowing what lay ahead. Only after leaving did new possibilities open for her. She highlights that challenges and chaos are inevitable parts of progress, and committing despite uncertain outcomes reveals capabilities invisible while standing still. Her message is clear: "Just do it. Waiting is not the answer. Take messy action."
Heather Monahan demonstrates how generosity, genuine support, and a commitment to adding value build powerful professional relationships and open doors.
Monahan illustrates the importance of actively supporting others as the foundation for reciprocal relationships. When approaching Gary Vaynerchuk's partner or Jesse Itzler's business partner, she centered her approach on "How can I help you?" rather than what she could gain. This attitude builds trust and earns future support, as seen when Gary's partner responded: "If there's ever anything I can do for you, don't hesitate to ask, consider it done." She also emphasizes that maintaining a strong LinkedIn presence filled with reviews and examples of her work builds credibility before any initial interaction, showcasing her expertise and authentic persona to potential collaborators.
Monahan sets herself apart through attentive gestures. After noticing Jesse Itzler admired her microphone during an interview, she sent him the same model as a gift with a thank you note, demonstrating genuine care beyond any transaction. Her approach is rooted in the belief that continually adding value attracts opportunities. By offering to support others' projects and promote partners' businesses, she creates goodwill that comes back in the form of introductions to dream guests and prestigious interviews. She believes, "Keep leading with good, keep adding value to others… at some point, good's gonna come back to you."
Heather Monahan shares how persistence, creativity, leveraging networks, and adaptability help her achieve ambitious goals, particularly in securing connections with high-profile individuals.
Monahan illustrates the importance of continual outreach by describing how she spent years messaging Gary Vaynerchuk before receiving a response. She emphasizes that consistent efforts increase the probability of eventually reaching your target, and rejection is not an endpoint but a step in identifying the right path. She makes it a habit to monitor prospects through Google Alerts, which revealed Gary was launching a wine company. She then targeted his more accessible partner, recognizing that connecting with team members can create new entry points. Monahan also underscores the value of networking for introductions, recounting how friend Scott offered to introduce her to Jesse Itzler's business partner and another friend facilitated an interview with Ryan Serhant, demonstrating that cultivating supportive networks dramatically increases opportunities.
Monahan describes the importance of embracing uncontrollable circumstances in collaboration. When told Jesse Itzler only did Zoom interviews on a limited schedule, she immediately accepted these terms. When technical difficulties threatened the connection, she volunteered to fly to Atlanta instead. Her willingness to adjust logistics and remain solutions-oriented encourages partners to engage rather than avoid, helping to ultimately achieve shared goals.
Success is often built on vision, patience, and delayed gratification. Heather's story underscores how long-term commitment, authenticity, and adaptability connect past efforts to unexpected opportunities.
Heather's journey to Dr. Phil's show exemplifies how decades of dedication lay the groundwork for breakthroughs. For 20 years, she honed her public speaking skills before stepping on the TEDx stage. Though her 2019 TEDx Talk didn't immediately yield massive attention, nearly three years later Dr. Phil's producer discovered it via the YouTube algorithm. This "out-of-left-field" opportunity traced directly back to years of accumulated experience, demonstrating how previous work finds new value when circumstances align.
Heather openly shares her initial disappointment when her TEDx Talk didn't garner immediate millions of views, yet she continued moving forward. She encourages others to believe in themselves even if immediate payoff isn't evident, emphasizing that "you might not always see the payoff right when you put the work in, but have faith that those dots are going to connect." She deliberately chose to present a unique perspective, focusing on women bullying other women in the workplace—a rarely discussed topic requiring vulnerability. This authentic approach didn't bring instant praise but ultimately caught Dr. Phil's producer's attention.
Heather reflects on how failed ventures like Perielas taught her market lessons and guided her toward more unique offerings. She emphasizes that unexpected outcomes aren't failures—her flexibility in traveling in person after a failed remote interview led to an even greater opportunity interviewing both Jesse and Sarah Blakely live on stage. Heather's years of speaking, content creation, and brand-building culminated unexpectedly when an algorithm delivered her work to the right person. She concludes with personal faith: "I believe the best is yet to come. It's God's plan, not mine." Maintaining a vision, continuing to take risks, and developing new ideas is essential for ongoing growth and ambition.
1-Page Summary
Heather Monahan urges people to take action now instead of waiting for perfect conditions. She observes that many individuals fall into the trap of analysis paralysis, endlessly waiting for the “right” moment to pursue their goals. She emphasizes that waiting only stalls progress and often serves as an excuse driven by fear and uncertainty.
Monahan describes how a common struggle is the desire for perfection before taking steps forward. People frequently freeze, wanting everything—the timing, the circumstances, the market—to align perfectly before they move. She labels these as excuses, stating, “All of that is BS, excuses.” She points out that searching for the perfect moment leads to endless delay, reinforcing fear and uncertainty, and preventing meaningful progress toward goals. Perfectionism, she argues, only blocks action and keeps people from achieving their dreams.
Monahan insists that imperfect action is far preferable to inaction. She shares personal stories about feeling nervous or unsure—for example, launching a podcast or traveling to the Dr. Phil show despite chaos in her life—but always reminds herself and others: “Done will always be better than perfect.” Real, messy efforts yield growth and often produce unexpected opportunities and solutions that would never surface in a state of waiting. She notes that projects and ideas may not always unfold as planned, or fruition may be delayed, but concrete action is what reveals the right direction. For instance, her relationships and partnerships evolved in surprising ways once she put herself out in the world and got started.
Monahan explains that “imperfect real work is more valuable than perfect imaginary work.” She compares the outcomes of waiting against choosing to commit and move forward, recalling how her life improved only after she left an unfulfilling job rather than staying stuck in fear.
Monahan discusses how fear of the unknown and a lack of certainty can ke ...
Taking Immediate Action Over Waiting For Perfect Conditions
Heather Monahan exemplifies how generosity, genuine support, and a commitment to adding value open doors and build powerful professional relationships. Through specific gestures, strategic brand-building, and a mindset centered on service, she demonstrates how fostering reciprocal goodwill leads to long-term opportunities and success.
Monahan illustrates the importance of generosity and actively supporting others as the foundation for strong, reciprocal relationships. When she approached Gary Vaynerchuk’s partner via LinkedIn, she offered her expertise in wine business launches and highlighted her willingness to help him avoid mistakes she had made. Similarly, on a call with Jesse Itzer's business partner, Monahan immediately asked how she could assist and support him, offering ideas and connections for his new ventures.
Rather than focusing on what she could gain, her approach centered on asking, “How can I help you?” This attitude builds trust and rapport, as seen when Gary’s partner responded positively and offered help in return: “If there's ever anything I can do for you, don't hesitate to ask, consider it done.”
Monahan’s generosity extends to peers such as Scott McGregor, for whose charity book she wrote a chapter. Their friendship is marked by ongoing reciprocal support—she continually seeks ways to repay Scott for his kindness and willingness to connect her with high-profile guests.
By consistently helping others, Monahan fosters trust and earns future support, showing that generosity sets apart lasting, fruitful relationships.
Monahan emphasizes that a strong, authentic presence across professional platforms, especially LinkedIn, is vital for building credibility before an initial interaction. She maintains an active LinkedIn profile filled with reviews, recommendations, and examples of her work, allowing potential collaborators to see her expertise and authentic persona in advance.
She advocates for consistent content creation and authentic engagement, which showcases who she truly is rather than projecting a fake persona. This openness not only attracts opportunity but also makes collaboration more seamless, as potential partners already know her reputation, work ethic, and values.
By displaying valuable content and maintaining platform visibility, Monahan demonstrates professionalism and builds confidence in those considering collaboration.
Monahan sets herself apart through gestures that show attentiveness and genuine care. After interviewing Jesse Itzler at his home, she noticed he admired her microphone. Following their interaction, she sent him the same microphone as a gift along with a thank you note, demonstrating thoughtful attention to detail and a desire to make him feel valued.
Such gestures—whether a post-meeting gift or a personal note—demonstrate commitment to the relationship beyond any transaction, fostering deeper connection. Monahan consistently li ...
Building Relationships Through Value Creation and Adding Value
Heather Monahan shares how a combination of persistence, creativity, leveraging her network, and adaptability has helped her achieve ambitious goals, particularly in securing connections with high-profile individuals.
Monahan illustrates the importance of continual outreach by describing how she spent years directly messaging Gary Vaynerchuk before ever receiving a response. She explains that consistent, repeated efforts—"showing up and knocking on different doors"—increase the probability of eventually reaching your target. This approach is rooted in the acknowledgment that sales, and by extension relationship-building, is a numbers game. When she was finally acknowledged but then quickly dismissed, she accepted it as part of the process rather than a personal failure, using it as motivation to try different strategies rather than losing momentum. Monahan emphasizes that rejection is not the end point but a step in identifying the right path. She notes, “I’ll ask for what I want. When I see the opportunity, I might not always get it in the moment... And if they don't, it wasn't really meant for us,” highlighting the balance of hope and tenacity required.
Monahan makes it a habit to monitor her prospects, setting up Google Alerts—for instance, on Gary Vaynerchuk—to receive constant updates about activities that offer timely engagement opportunities. When a Google Alert revealed Gary was launching a wine company with a partner, she targeted the less prominent partner, recognizing he would be more accessible and could provide a pathway to Vaynerchuk. This strategy acknowledges that directly targeting an ultimate goal may not always be effective, and connecting with accessible team members or partners can create new entry points. She repeated a similar approach when told by an assistant that her target was unavailable, opting to connect with a business partner instead. This creativity in tracking and engaging different paths shows the power of staying alert for relevant developments and adapting one's approach based on the ecosystem around a target.
Monahan underscores the value of networking for introductions. She recounts how a friend, Scott, who she built a relationship with through mutual support and adding value, offered to introduce her to Jesse Itzer’s business partner, opening new doors. Similarly, she secured an interview with Ryan Serhant after a friend—who happened to be interviewing him—recommended her and facilitated the introduction. Monahan highlights that she often did not ask for these favors directly, but previous conversations about her goals and the kinds of guests she was seeking paid off when those in ...
Persistence, Strategic Follow-Up, and Diverse Approaches to Achieve Goals
Success is often built on vision, patience, and a willingness to embrace delayed gratification. Heather’s story underscores how long-term commitment, authenticity, and adaptability connect past efforts to unexpected and rewarding opportunities.
Heather's journey to an opportunity with Dr. Phil's show exemplifies how decades of dedication lay the groundwork for future breakthroughs. For 20 years, she honed her public speaking skills in corporate America before ever stepping on the TEDx stage. When her TEDx Talk was released in late 2019 after significant preparation, it did not immediately yield massive attention or success. However, the experience and credibility gained over those years proved pivotal later.
The relevance of Heather’s earlier work became clear when, nearly three years after her TEDx Talk, Dr. Phil's producer discovered it via the YouTube algorithm. This seemingly “out-of-left-field” opportunity actually traced directly back to years of accumulated experience and effort. Heather notes that the producer was convinced by the TEDx Talk, demonstrating how previous work finds new value when circumstances and timing align.
Heather openly shares her initial disappointment when her TEDx Talk did not garner an immediate reaction or millions of views as she had hoped. Nevertheless, she continued to move forward, trusting that the value of her hard work would connect to future outcomes.
Through stagnant periods and apparent lack of recognition, Heather’s faith in her work and vision sustained her. She encourages others to believe in themselves even if immediate payoff isn’t evident, emphasizing that “you might not always see the payoff right when you put the work in, but have faith that those dots are going to connect.”
Heather deliberately chose to present a unique perspective, focusing her TEDx Talk on the rarely discussed topic of women bullying other women in the workplace. This approach required vulnerability and risk but set her apart from more conventional topics.
Taking the risk to be authentic didn’t bring instant praise, but Heather is grateful in retrospect for following her truth. Her willingness to address a difficult subject and not “show up vanilla like everybody else” contributed to the distinctive qualities that ultimately caught the Dr. Phil producer’s attention.
Heather reflects on her business experience with Perielas, recognizing that, despite the venture not succeeding, it taught her market lessons and guided her toward more unique offerings. She highlights how being a smaller company gave her the ability to pivot quickly, in contrast to larger, less agile organizations.
Vision, Patience, and Delayed Gratification
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