#523 When to Push, When to Pivot, and When to Ask for Help with Heather
In this episode of Creating Confidence, Heather Monahan shares her experiences transitioning from a radio industry professional to an author and speaker after being fired from her position. She discusses how her career pivot led to opportunities including speaking engagements, a TEDx talk, teaching at Harvard, and writing for HarperCollins, while emphasizing that expertise in one field does not guarantee immediate success in another.
Monahan explores the role of continuous learning and persistent effort in career development, drawing from her own journey of leveraging past experiences to enhance future endeavors. She addresses the importance of self-compassion during career transitions and explains how viewing setbacks as opportunities for growth, rather than failures, can contribute to professional development and a growth mindset.
This is a preview of the Shortform summary of the May 21, 2025 episode of the Creating Confidence with Heather Monahan
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1-Page Summary
Overcoming Adversity and Perseverance
Heather Monahan shares her journey of personal and professional growth through adversity. After being fired, Monahan used this experience to reflect on her career trajectory and learn from past decisions. She notes that this reflection helped her realize she should have started her own company earlier in her career.
Despite being an industry expert, Monahan had to restart her career path, achieving unexpected success through speaking engagements, a TEDx talk, teaching at Harvard, and writing for HarperCollins. She emphasizes that progress comes through "messy and aggressive action, repeated action," and success requires persistent effort and continuous learning.
The Importance of Patience, Grace, and Self-Compassion
During her transition from radio industry professional to author and speaker, Monahan learned valuable lessons about self-compassion. She discusses how expertise in one field doesn't guarantee immediate success in another, emphasizing the importance of giving oneself grace during career transitions. Rather than viewing setbacks as failures, Monahan encourages seeing them as opportunities for growth, pointing to her own journey from being fired to achieving various professional accomplishments.
The Power of Experience, Expertise, and Continuous Learning
Monahan's transformation from self-publishing her first book to working with HarperCollins Leadership demonstrates the value of leveraging past experiences. Her new book's success as Amazon's number one new release three months before launch showcases how applying learned lessons can enhance future endeavors. She emphasizes that challenging oneself in new environments, while initially frightening, becomes more manageable over time and contributes to developing a growth mindset.
1-Page Summary
Additional Materials
Counterarguments
- While Monahan's reflection led her to believe she should have started her own company earlier, it's possible that her experiences and the timing of her firing were necessary precursors to her readiness to successfully launch a business.
- Success through speaking engagements, a TEDx talk, teaching at Harvard, and writing for HarperCollins is impressive, but it's important to acknowledge that not everyone has access to these opportunities, and success can be achieved through various paths.
- The idea that progress comes from "messy and aggressive action" might not resonate with everyone; some may find that careful planning and strategic action align better with their personal or professional goals.
- The concept of self-compassion is valuable, but it's also important to balance self-compassion with accountability to ensure that one learns from their mistakes and takes responsibility for their actions.
- While viewing setbacks as opportunities for growth is a positive mindset, it's also valid to recognize and address the emotional and practical challenges that come with setbacks.
- Leveraging past experiences is indeed beneficial, but it's also worth considering that sometimes, past experiences can limit one's thinking and innovation if not critically assessed.
- Challenging oneself in new environments is a way to grow, but it's also important to recognize the value of expertise and sometimes deepening one's skills in a familiar environment can be just as beneficial for personal and professional development.
Actionables
- You can start a "messy action" journal to document daily actions that push you out of your comfort zone. Each day, write down one action you took that felt uncomfortable or imperfect, reflecting on what you learned and how it might lead to progress. For example, if you're shy, your action might be initiating a conversation with a stranger, and then noting how it felt and what outcomes it led to.
- Create a "setback flip" challenge for yourself where you identify a recent setback and brainstorm five ways it can be an opportunity for growth. If you were passed over for a promotion, list how this can free up time for personal projects or motivate you to seek additional training.
- Develop a "growth mindset roadmap" by identifying a new environment or field you're curious about and outline small, manageable steps to explore it. For instance, if you're interested in gardening but have no experience, your roadmap might start with planting a single type of vegetable and gradually expand to a full garden, documenting the learning process and mindset shifts along the way.
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Overcoming Adversity and Perseverance
Heather Monahan provides insight into how overcoming adversity and persevering through challenges can lead to personal and professional growth.
Reflect On Challenges to Learn From Mistakes
Being Fired Taught Monahan to Compare Current Self To Early-Career Self
Heather Monahan reflects on the experience of being fired and how it gave her the opportunity to compare her current self to her early-career self. This comparison helped her learn from her mistakes and use this reflection to inform her future decisions. For example, she wishes she had left her job to start her own company years ago.
Embrace Progress and Celebrate Small Wins
Monahan, an Industry Expert, Needed Time and Patience to Restart, Staying Motivated By Recognizing Her Growth
As an industry expert, Monahan talks about her unexpected achievements, which include starting a speaking business, being named a top 40 keynote speaker, giving a TEDx talk, teaching at Harvard, being appointed to a board, writing a book with HarperCon's leadership, and launching a podcast. Monahan discusses her journey of restarting at a different point in her career and the need for time and patience to build up to previous levels of success and knowledge.
She emphasizes that progress is made through "messy and aggressive action, repeated action." Monahan also points out that understanding the connections between one's achievements is only possible after the fact, underscoring the importance of both recognizing and celebrating small wins along the way.
Maintain Faith That Success Will Come Through Effort
Monah ...
Here’s what you’ll find in our full summary
Overcoming Adversity and Perseverance
Additional Materials
Counterarguments
- While reflecting on past challenges can be beneficial, it's important to acknowledge that not everyone may have the resources or support systems in place to turn such reflections into actionable growth opportunities.
- Achieving success after a career setback like being fired is commendable, but it's also necessary to consider that individual experiences can vary greatly, and not everyone may have the same opportunities or platforms to restart their career as successfully as Monahan did.
- The concept of making progress through "messy and aggressive action" might not resonate with or be applicable to all individuals or industries, where careful planning and risk aversion can be equally valid strategies.
- Celebrating small wins is important, but it's also crucial to recognize that some individuals may struggle to identify or feel validated by small successes, especially in high-pressure environments or during times of personal difficulty.
- The idea that success comes from trial and error and persistence might oversimplify the co ...
Actionables
- Reflect on your past self by writing a "Then and Now" journal entry once a month to track your personal and professional growth. This activity involves comparing your current skills, mindset, and achievements with where you were at the start of your career or a specific earlier point in time. For example, if you used to struggle with public speaking, note any improvements or experiences that show how you've grown, like leading a meeting confidently.
- Create a "Small Wins Jar" where you write down even the tiniest accomplishments on slips of paper and drop them in a jar. At the end of each week, empty the jar and review your progress. This could be as simple as completing a task you've been procrastinating on or receiving positive feedback from a co ...
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The Importance of Patience, Grace, and Self-Compassion
Heather Monahan speaks about the significant role of patience, grace, and self-compassion in personal and career growth, especially during periods of transition and uncertainty.
Avoid Self-Criticism and Extend Compassion When Facing Challenges
Monahan opens up about her own challenges with impatience and self-criticism, especially during her shift from being an established radio industry professional to starting anew in different fields after she was let go. She recognizes the importance of granting herself grace and patience to navigate the transition and build success over time. Monahan reflects on her transition and the weight of choosing to accept a severance package, which she calls a "bridge play," and underscores the need for self-compassion when making difficult decisions in life. She also highlights the importance of maintaining belief in one's credibility and turning the act of signing a non-disclosure agreement (NDA) into a positive step toward starting a new business venture.
Monahan Advises Giving Herself Grace to Navigate Transitions and Avoid Self-Criticism For Not Achieving Instant Success
Monahan points out that expertise in one area does not guarantee immediate triumph in another. Reminiscing about her beginnings in the radio business at age 22 and comparing it to her current position as an author and speaker, Monahan emphasizes the unwarranted nature of self-criticism during these periods of change and growth.
Value Time and Experience in Developing Expertise
Monahan confesses that her initial struggles taught her invaluable lessons that contributed to her greater success down the line. She was surprised and proud when HarperCollins called, indicating the hard work she's put into her book launch and recognizing it as a substantial learning experience.
Monahan's Initial Struggles Taught Invaluable Lessons for Greater Success
She recalls how her early-career setbacks were instrumental in learning crucial lessons that later facilitated her success, affirming the value o ...
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The Importance of Patience, Grace, and Self-Compassion
Additional Materials
Counterarguments
- While patience, grace, and self-compassion are valuable, some might argue that they should be balanced with a sense of urgency and constructive self-criticism to drive progress and avoid complacency.
- The idea that one should avoid self-criticism might be challenged by the view that self-criticism, when balanced and fair, can be a powerful motivator for self-improvement and excellence.
- The notion that expertise in one area does not guarantee success in another could be countered by pointing out that transferable skills and knowledge often contribute significantly to success in new endeavors.
- Some may argue that while initial struggles can lead to greater success, not all struggles are equally valuable, and some can be avoidable or unnecessarily detrimental.
- The emphasis on valuing time and experience might be met with the argument that innovation and adaptability can sometimes outweigh the benefits of experience, especially in rapidly changing industries.
- The perspecti ...
Actionables
- Start a "Patience Journal" to track your personal growth journey, noting down moments where you practiced patience and the outcomes. This could be as simple as waiting an extra day before sending a follow-up email and observing how this affects your stress levels and the response you receive. Over time, you'll have a record of how patience has benefited you in various situations.
- Create a "Setback Canvas," a visual board where you map out recent challenges and articulate the skills or knowledge you gained from each. For instance, if a project at work didn't go as planned, you might identify that you improved your problem-solving or communication skills through the process. This tangible representation can help you reframe setbacks as growth opportunities.
- Develop a "Transition Timeline" for your cu ...
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The Power of Experience, Expertise, and Continuous Learning
Continuous learning is a powerful approach for leveraging past experiences to improve future efforts, stay adaptable and competitive, and navigate through various challenges. Monahan shares her journey and highlights key strategies for growth and development.
Leverage Past Experiences to Improve Future Efforts
Monahan's Shift From Executive to Author Taught Her Key Lessons For Her Book Launch
Monahan reflects on her journey from self-publishing her first book without understanding the process to working with an expert team at HarperCollins Leadership for a new book. She translates the lessons learned from her past role as a corporate executive and her initial attempt at publishing into progress for her current book launch. Monahan shares the achievement of her new book becoming the number one new release on Amazon three months before its launch, which underscores the value of applying experience to enhance future endeavors.
Embrace Lifelong Learning to Stay Adaptable and Competitive
Monahan Highlights the Value Of Acquiring Knowledge and Skills For Future Success
Monahan speaks to the importance of learning from experiences and the substantial role this plays in setting one up for future success. She believes that the knowledge and skills acquired—even from a single experience—can significantly improve one's positioning for success going forward. Monahan shares that her continual effort in learning and preparing for her current book launch with prelaunch activities and a pre-order campaign is a testament to the value of continuous improvement and effort.
Develop a Growth Mindset to Navigate Challenges
Monahan's Growth Thr ...
Here’s what you’ll find in our full summary
The Power of Experience, Expertise, and Continuous Learning
Additional Materials
Counterarguments
- Continuous learning, while beneficial, can sometimes lead to information overload or burnout if not managed properly.
- Not all past experiences may be relevant or beneficial for future endeavors; some experiences might teach incorrect lessons or encourage bad habits.
- The transition from executive to author is unique to Monahan's situation and may not be universally applicable or replicable for others.
- Lifelong learning is important, but it should be balanced with practical application and experience; theoretical knowledge alone may not ensure adaptability or competitiveness.
- Acquiring new knowledge and skills is essential, but it is also important to recognize and utilize existing strengths and competencies.
- A growth mindset is valuable, but it is also important to acknowledge and respect personal limits and to sometimes accept things that cannot be changed.
- Venturing into new arenas can be beneficial for growth, but it can also be risk ...
Actionables
- You can start a "Challenge of the Month" club with friends to tackle new skills or experiences together, providing mutual support and accountability. Each month, select a new skill or challenge that is outside of everyone's comfort zones. This could range from learning a new language to trying out a sport or even public speaking. The key is to choose activities that none of the members are familiar with, ensuring that everyone is starting from scratch and can share in the learning process.
- Create a personal "Experience Journal" to document and reflect on new experiences and the lessons learned from them. This journal should be dedicated to recording the outcomes of new challenges you've faced, what strategies worked, what didn't, and how you've adapted your approach for the future. For example, if you decided to learn how to code, jot down your progress, the obstacles you encountered, and how you overcame them. Over time, this journal will serve as a tangible record of your growth and adaptability.
- Develop a "Skill Swap" arrangement with someone ...
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