Podcast Summary: Creating Confidence with Heather Monahan

Episode: Confidence Classic: Why Fear Means You’re Exactly Where You Need to Be
Host: Heather Monahan
Date: September 9, 2025

Episode Overview

In this Confidence Classic solo episode, Heather Monahan dives deep into how fear and adversity are not only unavoidable but are actually crucial signposts that you're heading in the right direction for personal and professional growth. Drawing from her own life journey—from humble beginnings, through corporate adversity, to entrepreneurship and best-selling authorship—Heather candidly reflects on the transformative power of difficult moments and how to spot when it’s time to leave the wrong “table” in search of the right one. She also answers a listener's question about overcoming the legal fears of writing honestly about personal experiences in a public way.

Key Discussion Points & Insights

1. The Impact of Adversity and the 'Right Table'

• Adversity as Strength Training:

  • Heather recaps personal stories from her career, highlighting how facing sexual harassment, public humiliation, and being let down by peers actually strengthened her, making her more resilient and unshakeable.
  • "The next time you’re facing adversity, choose to see it as this is my strength training moment. That’s going to help springboard me to that next level." (06:12)

• Surround Yourself with Genuine Supporters:

  • Using examples from her own journey, Heather stresses the importance of leaving environments where you aren’t valued and seeking out rooms where you’re truly wanted and supported.
  • “When you’re sitting at a table surrounded with people that don’t actually want you there, there’s nothing wrong with you. You’re in the wrong room. Get up from that table, leave that room, and go find a room where people want you at the table.” (00:00, repeated at 29:00)

• Red Flags Are Deal Breakers:

  • Heather encourages listeners not to ignore early signs that people are unwilling to stand up for them in crucial moments.
  • “Red flags are not red flags. Those are deal breakers.” (11:00)

2. Seeing Through Your Own Lens

• Will Smith Oscars Incident Reflection:

  • Heather analyzes the Oscars slap (Will Smith/Chris Rock/Jada Pinkett Smith) and uses it to illustrate that people interpret situations based on their own past experiences, advocating for empathy and open-mindedness.
  • “Everybody sees situations and experiences through the lens of their life... you feel differently based upon the lens you see things through.” (02:30)

• Desire for Public Defense:

  • Heather confesses her emotional reaction to someone being publicly defended, something she rarely experienced, despite disavowing physical violence.
  • “I want to be with people who don’t hit people, but who jump up to defend me immediately, who don’t shrink back into the darkness... I want to be around people who really have my back. And I want that for you.” (08:10)

3. Personal Backstory & Climbing the Ladder

• Early Hustle and Setbacks:

  • Heather shares her journey from humble beginnings in Worcester, MA, through a rapid ascent in radio sales, supported by a strong work ethic developed through early, varied jobs.
  • “I came from nothing, and I taught myself sales, from hustling and paper routes and bartending…” (15:40)

• Catalyst Moments:

  • Unexpected heartbreaks and professional challenges (being cheated on, being harassed at work, losing her job) often turned into opportunities for radical change.
  • “All these awful things had to happen to propel me to say, I’m willing to make the leap.” (18:20)

• Learning Strategic Lessons:

  • Highlights the importance of knowing who the true decision makers are and not being afraid to walk away when necessary.
  • “Never ask someone who can only give you a no. Never ask them for a yes.” (21:55)

• Reinvention After Getting Fired:

  • Shares how being fired as Chief Revenue Officer forced her into entrepreneurship, writing, and speaking—ultimately allowing her to discover her purpose and step into greater opportunities.
  • “When you’re shrinking yourself to fit in somewhere you’ve already outgrown, you’re not living to your potential.” (26:50)

4. Finding and Owning Your Purpose

• Following the Magic:

  • Encourages listeners to take seriously the moments in life and work where they feel energized (“magic moments”) rather than dismissing them as impractical.
  • “If you ever have that moment in your life that just feels like magic, but then you shake your head and say... I can’t pay my bills with this. Don’t do that.” (27:22)

• Turning Setbacks into Launchpads:

  • Reflects on reframing getting fired as a redirection, not rejection, and finding validation in the stories of other successful figures who bounced back from setbacks.
  • “I have not been rejected. I have been redirected to something so much bigger and so much better for me.” (24:50)

• Building a Speaking Business:

  • Heather details her serendipitous entry into public speaking, building a business around it, and the importance of seeking out people who have already done what you want to do.

5. On Fear, Truth-Telling, and Legal Risk in Writing

• Listener Q&A on Legal Anxiety in Memoir Writing (33:08)
  • A listener asks about how to handle potential legal backlash when writing personal stories that involve real people, especially adversaries.
  • Heather candidly describes the fear she felt when releasing her first book, Confidence Creator, and the conflicting advice she received from her sister (an attorney), her editor, and author James Altucher.
    • “My sister is an attorney... she said, ‘You can’t publish this. You’re gonna get sued.’” (36:00)
    • “My editor... said, ‘Just do it anyways. I never got sued.’” (38:00)
  • Sharing wisdom from James Altucher’s podcast, Heather demystifies fears around lawsuits and underscores the importance of consulting a real attorney while also acknowledging that many fears never materialize.
  • Ultimately, she reveals she was never sued, and shares the added confidence gained after a lawyer for her major publisher explained that the statute of limitations had expired, so she was “in the clear.”
  • “I was so sure I was going to get sued. I didn’t get sued... I was worrying about something that never even transpired. I was wasting my energy on things that never came to fruition.” (55:20)

Notable Quotes & Memorable Moments

• On Room Selection:

  “When you’re sitting at a table surrounded with people that don’t actually want you there, there’s nothing wrong with you. You’re in the wrong room. Get up from that table, leave that room, and go find a room where people want you at the table.”
  —Heather Monahan, (00:00 & 29:00)

• On Adversity as a Springboard:

  “The next time you’re facing adversity, choose to see it as this is my strength training moment. That’s going to help springboard me to that next level.”
  —Heather Monahan, (06:12)

• On People Who Have Your Back:

  “I want you to be with people who have your back. I want to be with people who have my back.”
  —Heather Monahan, (08:15)

• On Dealing With Fear:

  “Fear is a green light that means go and go faster, remember?”
  —Heather Monahan, (44:25)

• Red Flags as Deal Breakers:

  "Red flags are not red flags. Those are deal breakers."
  —Heather Monahan, (11:00)

Essential Timestamps

• 00:00 – Opening advice on choosing the rooms and tables where you are celebrated.
• 02:30 – Reflecting on the Oscar’s slap (Will Smith/Chris Rock); empathy and perception.
• 06:12 – Using adversity as strength training.
• 08:10 – Public defense and craving true supporters.
• 11:00 – Red flags and what really matters in your inner circle.
• 14:08 – Heather’s early background and work experience.
• 18:20 – Turning heartbreak and hardship into opportunity.
• 21:55 – Learning to find decision-makers and not waste time.
• 24:50 – Reframing failure as redirection.
• 27:22 – ‘Magic moments’ and following your passion.
• 29:00 – Reiterating the importance of finding the right people.
• 33:08 – Answering a listener's question on legal fears in writing.
• 36:00 – Attorney’s warning.
• 38:00 – Editor and James Altucher’s counter-advice.
• 44:25 – On fear being a signal to move forward.
• 55:20 – Looking back, Heather realizes worries about lawsuits were unfounded.

Takeaways for Listeners

• Fear and adversity are indicators of growth and opportunity, not warning signs to turn back.
• Your perspective is shaped by your journey; honor it, but remain open to others’ viewpoints.
• Audit your circle: Be where you are wanted, not where you are tolerated.
• Strategic risk and honest self-advocacy open new doors—sometimes in the most unexpected ways.
• When paralyzed by legal or personal fears about telling your story, consult experts, but don't let fear keep you silent if telling your truth matters.
• Keep your confidence active—decide, plan, and surround yourself with those who elevate you.

Heather leaves listeners with encouragement:

“Keep creating your confidence. You know I will be.” (59:05)