In this episode of Creating Confidence with Heather Monahan, Heather explores the challenges and rewards of speaking up for yourself in both personal and professional settings. She discusses how expressing authentic needs and establishing boundaries impacts confidence and wellbeing, while sharing practical strategies for building assertiveness through low-stakes practice scenarios that prepare you for bigger asks.
Heather draws from her own experiences with rejection and adversity, including revising her book proposal fifteen times and receiving only one publisher acceptance out of fifteen submissions. She covers topics including resilience in the face of setbacks, the importance of diversifying income streams, cultivating gratitude during difficult times, and building confidence independent of external validation. The episode emphasizes how consistent effort, strategic persistence, and surrounding yourself with supportive people can transform obstacles into opportunities for growth.

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Speaking your truth and asserting your needs in relationships is challenging but empowering. Expressing authentic feelings leads to greater self-respect and personal growth, even when outcomes are uncertain.
Owning your voice requires courage in both personal and professional settings. While the outcome isn't always favorable, the act of speaking up is transformative. Articulating your needs ensures everyone's needs are heard and respected, and overcoming the misconception that self-advocacy is selfish unlocks personal empowerment.
Building assertiveness starts with small requests—like persistently asking for a plastic cup at a football game—which builds confidence for bigger asks later. Begin in low-stakes scenarios, and when met with "no," stay friendly and positive while escalating the request. This persistent approach often yields results and sharpens assertiveness skills over time.
Your decisions and boundaries directly impact your confidence and long-term wellbeing. Choosing not to speak up erodes self-assurance, while suppressing your voice leads to resentment, frustration, and even physical illness. With practice, asserting yourself becomes second nature—what begins as conscious effort evolves into automatic response, transforming your life.
Establishing authentic connections requires confidence, approachable body language, and positivity. A genuine smile and open posture encourage cooperation, while flexibility and readiness to pivot facilitate goal achievement in any negotiation.
Heather Monahan's experience exemplifies the importance of resilience when facing rejection. She revised her book proposal fifteen times over a year before her agent approved it, noting "if I had thrown in the towel at version 14, you wouldn't be reading this book today." After her agent sent the proposal to fifteen publishers, she received only one "yes" initially, but a friend's advice—"it's not how many no's you get. The truth is you really only need one yes"—helped her reframe rejection as feedback rather than defeat.
Monahan stresses wisely allocating resources using her "grief to gross ratio," evaluating whether potential reward outweighs effort. During the pandemic, when her speaking engagements vanished, she adapted by diversifying revenue streams and maintaining inner certainty despite chaos. She chose to believe the crisis could be "exactly the right time" for her book's message about overcoming adversity, turning obstacles into opportunities through a growth mindset.
Difficult moments can consume our attention, causing us to forget the abundance of good surrounding us. Monahan reflects that it's vital to refocus on blessings and embrace moments of joy even amid hardship. She emphasizes that life's circumstances can transform dramatically in a short span—hardships aren't permanent, and blessings can arrive unexpectedly. She also acknowledges that experiencing sadness can honor past beauty while fostering hope for future possibilities.
Meaningful friendships require consistent effort and presence. Monahan prioritizes attending pivotal moments in friends' lives, which strengthens bonds and creates lasting memories. Her decades-long friendships offer irreplaceable perspective, loyalty, and support through life's highs and lows. She stresses the importance of intentionally surrounding yourself with positive, uplifting people, as the company you keep greatly shapes emotional well-being.
Confidence starts with mindset. Monahan emphasizes mental preparation before taking action—whether channeling a persona like Sasha Fierce or using positive self-talk. When speaking at an unfamiliar international finance conference, she trusts her ability to forge connections by finding common threads with her audience, reinforcing her belief in her adaptability.
A significant test of internal certainty comes in moments of waiting after making a bold ask. Monahan advises powering through silence without filling the gap prematurely, noting that "he or she who speaks first after the ask loses." She learned to interpret silence as simply an absence of communication rather than catastrophizing or assuming rejection, seeking facts and expert guidance instead.
When selecting a publisher, Monahan arranged calls to assess investment level and leadership style, choosing the partner whose leadership demonstrated full engagement and alignment with her goals. This reinforces that feeling valued and choosing compatible collaborators are essential to maintaining confidence independent of external praise.
Monahan demonstrates entrepreneurial resilience through identifying customer needs. Noticing consistent inquiries about coaching, she launched a group program via LinkedIn with a money-back guarantee and limited enrollment. The program sold out within days, generating immediate revenue and testimonials for future growth. She exceeded expectations by over-delivering during the inaugural month, though she soon realized this approach was unsustainable.
By adjusting offerings and pricing based on experience, Monahan balanced serving clients effectively with protecting her time and energy. She emphasized that both provider and clients must benefit for the model to last. She highlighted the critical importance of testimonials in a recommendation-driven market, urging entrepreneurs to collect them immediately as proof of value.
Monahan also reflected on building personal accountability systems without external oversight, creating clear objectives and maintaining regular check-ins to sustain focus and motivation independently.
1-Page Summary
Speaking your truth and asserting your needs, especially in relationships, is challenging but deeply empowering. Expressing your true feelings leads to greater self-respect and personal growth, even if outcomes are uncertain or difficult.
It takes courage and confidence to ask for what you want, whether it’s in personal or professional settings. Owning your voice does not mean the outcome will always be favorable, but the act of speaking up itself is transformative. The process is rarely easy, even for those who seem outwardly confident. In business, it may come naturally, but personal relationships often demand even more bravery.
Articulating your needs is vital—not just for yourself, but to ensure everyone’s needs are heard and respected. Overcoming the misconception that self-advocacy is selfish unlocks personal empowerment. Success is not guaranteed every time, but what matters most is showing up authentically and making your needs known.
Getting what you want often starts with simply asking, as shown by persistence in everyday moments—like requesting a coveted plastic cup at a football game. The courage to make even small requests builds the foundation for bigger, more significant asks later. Remind yourself of past successes and use motivational strategies to boost confidence, whether that’s channeling your inner Sasha Fierce or thinking of a time when you achieved something remarkable.
Begin standing up for yourself in low-stakes scenarios. Each small victory fuels bigger changes and increases confidence to tackle more significant matters. When a request is met with “no,” stay friendly and positive, and try escalating by asking if someone else can help—often this persistence leads to the desired outcome. If nothing else works, remember you’ve lost nothing by asking, and each attempt sharpens your assertiveness skills. Over time, consistent practice transforms you into someone who confidently advocates for yourself in any situation.
When met with resistance, don’t stop at the first “no.” A friendly, persistent approach—such as asking to speak to someone with the authority to help—surprises people and often yields results. This method, rooted in positive interaction and willingness to negotiate, makes even unlikely requests possible.
Your decisions and boundaries directly impact your confidence and long-term wellbeing. Prioritizing others’ needs or expectations at the expense of your own can lead to insecurity, frustration, and even health issues.
Choosing not to speak up chips away at your self-assurance. Failing to set limits for yourself—whether by taking on overwhelming obligations or remaining silent when you disagree—gradually erodes confidence. Conversely, standing your ground builds it.
Resentment and frustration result when you suppress your voice over time. Suppressed feelings not only discourage, but can manifest as physical illness. Regularly speaking up, without focusing solely on outcomes, brings relief and prev ...
Speaking Up, Setting Boundaries, and Finding Your Voice
Heather Monahan's experience exemplifies the importance of resilience and perseverance when facing rejection and adversity, underscoring how persistence, strategic action, and inner certainty can drive personal and professional transformation.
Heather Monahan describes her journey writing a book proposal, which she revised fifteen times over the course of a year before her literary agent finally approved it. With each submission, she faced rejection and mounting frustration, questioning herself and even her fit with her agent. Despite the discomfort and self-doubt, she continued revising, noting, “if I had thrown in the towel at version 14, you wouldn't be reading this book today.” She acknowledges that this process tested her self-confidence, requiring her to repeatedly pick herself up after setbacks.
Monahan faced further rejections as her agent sent her proposal to fifteen publishers, but she received only one “yes”—initially from a small publisher with an unsatisfactory deal. However, maintaining her focus on the possibility that “it was exactly the right time to publish her book,” she ultimately received strong offers from two major publishers. A friend’s advice—“it's not how many no's you get. The truth is you really only need one yes”—helped her reframe discouragement into determination, reinforcing that each rejection was feedback for improvement rather than a final defeat.
Monahan stresses the importance of wisely allocating resources and energy. She employs a personal “grief to gross ratio” to evaluate opportunities, asking herself, “what's the work put in versus the potential outcome?” If the potential reward outweighs the effort, she pursues the action; if not, she reevaluates her commitment. This approach extends to creating multiple revenue streams and diversifying business models, providing stability when conditions shift. During the pandemic, the cancellation of her speaking engagements—a primary revenue stream—forced her to adapt and innovate in problem-solvi ...
Resilience and Perseverance Through Rejection and Adversity
Difficult moments can easily consume our attention, causing us to forget the abundance of good surrounding us. It's human nature to focus on the one challenge, sadness, or obstacle rather than the many positive things happening simultaneously. However, over time, pain lessens and struggles subside. It is vital to refocus on what is good, to recognize blessings, and to actively find and embrace moments of joy, even amid hardship. Heather Monahan reflects that during quarantine, some days she was grateful for her son, their health, and their view, even as she faced overwhelming challenges like thinking her car was stolen when it was simply on another parking level. A helpful strategy she employs is always identifying something to look forward to in the near future—then, once reached, setting a new goal to maintain momentum and hope.
Life’s circumstances can transform dramatically in a short span—a month from now, life might look completely different. This quick changeability is what makes life both uncertain and extraordinary. The uncertainty that often evokes fear can end up being a great blessing, as Heather experienced after losing her job five years ago and unexpectedly building a successful speaking career. She also expresses gratitude for the return of in-person events post-pandemic, after a period where live engagements disappeared. Heather emphasizes that even if times are hard or uncertain, hardships are not permanent and blessings can arrive unexpectedly.
Heather acknowledges the importance of recognizing sadness, not avoiding it. Experiencing sadness can serve as a moment of reflection on past beauty or joy, reminding us of what we once had and can have again. This perspective shifts sorrow into a celebration of what was, fueling hope for the possibilities still ahead.
Meaningful friendships require consistent effort and presence. Heather describes prioritizing time for friendships—even when inconvenient or exhausting—because the dividends are immense. Attending pivotal moments in friends’ lives, such as surprising a lifelong friend at his bachelor party, strengthens bonds and creates lasting joyful memories. She reminisces about her group of friends she’s had since age 15, whose shared experiences span decades of life’s highs and lows. Their loyalty and mutual support have carried them through marriages, divorces, deaths, and celebrations together. Such relationships offer priceless perspective and comfort because they know each other's histories and have helped each other weather many storms.
Cultivating Gratitude and Maintaining Perspective During Difficult Times
Building confidence and certainty from within requires deliberate practice, mental preparation, and a commitment to not being overly swayed by external validation. The process often involves drawing on personal experience, finding genuine points of connection with others, recognizing the value of patience, and choosing partnerships grounded in mutual investment and shared goals.
Confidence often starts with mindset. Heather Monahan emphasizes the importance of preparing oneself mentally before engaging in action—whether by channeling the unshakable attitude of a persona like Beyonce's Sasha Fierce or cultivating positive self-talk such as, “I’ve got this.” Motivational music and recalling past achievements where the odds seemed insurmountable serve as emotional fuel, reminding individuals of their capacity to succeed.
Drawing from her own life, Heather describes facing the challenge of speaking at an international finance conference for the first time—a field unfamiliar to her. Instead of doubting herself, she trusts her ability to forge connections by leveraging shared experiences. Heather recalls that her ex-husband worked in finance and uses a story about that connection as an entry point to relate to the audience. She observes that finding a common thread enhances connection and relatability, which is incredibly powerful across any audience or boundary. This approach, rooted in both past experience and genuine outreach, reinforces her belief in her adaptability and problem-solving, further bolstering her confidence in new situations.
A significant test of internal certainty comes in moments of waiting—especially after asking for what you want. Heather asserts that the period of silence after a bold ask can be uncomfortable, sometimes triggering self-doubt or an urge to fill the gap prematurely. She advises to “power through, smile, and don’t say anything,” reminding that sometimes, “he or she who speaks first after the ask loses.”
Heather recounts an experience where, after securing a deal, silence from the publisher prompted worry and catastrophic thinking—imagining rejection before any actual evidence. She recognizes this as an old, unproductive pattern and now interprets silence as simply an absence of communication, nothing more.
Seeking facts rather than assumptions, Heather consults her agent for clarity. The agent confirms that the lack of communication was due to a transition within the publishing company, not a withdrawal of interest. This experience under ...
Building Confidence and Certainty Independent of External Validation
Heather Monahan demonstrates how entrepreneurial resilience and adaptability can drive revenue, generate demand-driven services, and ensure business sustainability, even when external circumstances require a shift in approach.
Heather began by reviewing audience messages and noticed consistent inquiries about consulting, executive coaching, and mentorship. Recognizing this clear demand, she decided to launch a group coaching program. She quickly created a LinkedIn post announcing the new program, offering to hold clients accountable for their goals, and included a 100% money back guarantee to alleviate buyer hesitation. She limited enrollment to 10 people and indicated the price would increase the following month, creating urgency.
Speed to market proved essential: the program sold out within days, even though Heather had not finalized the format. She studied other providers before deciding on a weekly group call supplemented with individual strategy sessions each month. The rapid launch generated immediate revenue as well as a batch of testimonials from satisfied clients, laying the groundwork for future growth.
During the inaugural month, Heather went above and beyond for what she charged, dedicating significant time to one-on-one coaching. This over-delivery resulted in outstanding testimonials, which became crucial assets for promoting subsequent sessions and attracting new clients.
Heather soon realized, however, that pouring all her effort into individual coaching was unsustainable. She adjusted offerings to structure the program in a way that worked for both her and her clients, shifting from exhaustive one-on-one calls to a more manageable model. She emphasized that both the provider and clients must benefit for the model to last, and she learned that undervaluing oneself undermines sustainability.
By re-evaluating the format, Heather was able to balance serving her clients effectively with protecting her time and resources. She faced the challenge of communicating changes transparently to clients, ensuring the relationship—along with business viability—was maintained. Her experience reinforced the need to regularly assess and refine offerings, ensuring long-term sustainability without burn ...
Creating Sustainable Business Practices and Diversifying Income Streams
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