The Courageous Choice

WRKdefined Podcast Network
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Every breakthrough begins with a decision — a moment of hesitation followed by a leap. “The Courageous Choice” is the podcast that explores those defining moments when leaders, entrepreneurs, changemakers, and individuals bet on themselves, defy expectations, and step into the unknown. Hosted by Jamie Jacobs, founder and CEO of Gig Talent, each episode explores bold career moves and industry-shaping innovations. We dive into the risks, the resilience, and the rewards that come with making the courageous choice.

  1. The Courageous Path to Purposeful Leadership

    18H AGO

    The Courageous Path to Purposeful Leadership

    This episode is a heart-to-heart dive into the real, raw relationship between fear and leadership. Barb Krol, Chief People Officer and seasoned coach, shares her transformative journey and powerful insights on how fear shapes us — and how embracing it can make us stronger, more authentic leaders. If you're ready to confront your fears and step into your most courageous self, this episode is your wake-up call. In this episode: Barb’s personal journey from fear of losing her career to fearless authenticity How fear manifests in leaders and how to recognize it in ourselves and others The connection between fear, shame, and grief, and how to navigate these emotions Practical steps to manage fear through small, courageous actions The role of vulnerability and candor in leading with confidence How to transform fear into exponential leadership impact The importance of continuous inner work and self-awareness for lasting leadership legacy Timestamps: 00:00 – Podcast Intro 00:33 – Introduction of guest Barb Croll, Chief People Officer at Orange County’s Credit Union 01:50 – Exploring the journey of leadership effectiveness and the role of fear 02:54 – Mid-career fear vs. later-career fear: Success vs. Mortality 04:00 – How leaders unknowingly operate from a place of fear and the denial of it 06:50 – The connection between fear, leadership, and shame 08:50 – The “Lion” vs. “CYA”: How fear affects decision-making and risk-taking 10:45 – Careful Candor: Learning to be comfortable being uncomfortable 12:20 – Comparing the “waves” of fear to the process of grief 14:30 – Redefining grief in the workplace: Aging, body changes, and career endings 15:50 – The “Second Act”: Finding boldness and fearlessness late in a career 18:10 – Breaking free from "political shackles" to add real value 19:10 – Can we fix the system? Systemic change vs. individual growth 20:45 – Leadership in the age of AI and rapid technology: Leading with less data 22:45 – The Kaizen Principle: The power of 1% daily improvement over perfectionism 25:20 – Silencing the inner chatter: "Did I do my best today?" 26:30 – Barb’s Final Advice: Do the internal work and "don't get caught in your belly button" Resources & Links: - Daring Greatly by Brené Brown - Kaizen Principle Explained - Orange County’s Credit Union  Connect with Barb: Linkedin Thanks for listening to “The Courageous Choice.” Be sure to leave us a review and subscribe so you don’t miss any conversations.  For more information, visit gigtalentagency.com or email us at podcast@gigtalentagency.com if you have any questions.

    28 min
  2. Leadership: Beyond the Facade with Phillip Stenger of Ascent

    APR 20

    Leadership: Beyond the Facade with Phillip Stenger of Ascent

    Are you tired of trying to win everyone's approval and losing your authenticity in the process? In this episode, Phillip Stenger drops truth bombs about leadership, fear, conflict, and the courage it takes to be real. Get ready to challenge everything you thought leadership should be — because real change begins when you embrace the uncomfortable. In this episode: The difference between respect and likeability, and why it matters How fear of not being liked can sabotage your leadership Building trust through honesty — even in tough decisions The power of embracing mistakes and vulnerability Practical tools for courageous leadership on your toughest days The role of meditation and mental health routines in resilient leadership Why you should own your wrongs — and celebrate your failures How to lead with confidence without losing yourself The concept of "confidence humility" rooted in self-awareness Moving beyond superficial niceness to real, tough conversations Timestamps 00:00 - Authenticity over approval in leadership 02:05 - First lesson on being liked in finance 06:14 - Respect vs. likeability: what leaders can actually control 08:23 - Building a company while managing external approval 10:42 - Fear, uncertainty, and how experience builds confidence 12:18 - Meditation, mental health, and leadership presence 14:37 - Making unpopular decisions with honesty 19:47 - The danger of “nice” cultures that avoid hard conversations 22:26 - What courageous leadership looks like in the moment 24:39 - Confident humility: strong opinions, open mind 25:10 - Advice for early-career professionals afraid of being disliked 28:35 - The permission slip: leaders can be wrong 30:24 - Building a culture that learns from mistakes Resources & Links: - Radical Candor by Kim Scott - The Courageous Leadership Series - “Confidence Humility” book - Meditation for Leaders - Headspace - Own Your Mistakes - Harvard Business Review Connect with Phillip Stenger: LinkedIn Thanks for listening to “The Courageous Choice.” Be sure to leave us a review and subscribe so you don’t miss any conversations.  For more information, visit gigtalentagency.com or email us at podcast@gigtalentagency.com if you have any questions.

    33 min
  3. Redefining Talent Access in the Age of Disruption with Tony Buffum of Human Cloud

    MAR 11

    Redefining Talent Access in the Age of Disruption with Tony Buffum of Human Cloud

    Tony Buffum, Head of Enterprise Strategy at Human Cloud, joins us on this episode to talk about the evolution of talent strategy and what it truly takes for leaders to navigate workforce transformation with courage. With more than two decades leading global HR and talent transformation initiatives, Tony brings a rare perspective across enterprise, platform and advisory work. He explains how the shift toward flexible and on-demand talent models is not just an operational adjustment but a strategic reset. We explore the courageous choices leaders must make as traditional workforce models strain under new realities. Tony challenges organizations to rethink how they align people, technology and business strategy and to move beyond incremental change toward intentional transformation. Key Takeaways: 00:00 Introduction. 07:02 Traditional workforce planning struggles to keep pace with shifting talent demands. 08:52 Flexible talent enables expertise deployment within days, not months. 15:02 Over 50% of students now prefer independent work over full-time roles. 19:08 Success requires managing flexible and full-time talent as one aligned team. 24:07 Private equity value creation depends on rapid, flexible access to expertise. 27:20 Technology shifts require talent models that flex as fast as markets change. 34:15 HR must lead workforce transformation or risk being displaced by it. Resources Mentioned: Tony Buffum https://www.linkedin.com/in/tony-buffum-hrexecutive/ Human Cloud LinkedIn https://www.linkedin.com/company/humancloud/ Human Cloud | Website https://humancloud.work Human Cloud platform https://app.humancloud.com Upwork https://www.upwork.com Thanks for listening to “The Courageous Choice.” Be sure to leave us a review and subscribe so you don’t miss any conversations.  For more information, visit gigtalentagency.com or email us at podcast@gigtalentagency.com if you have any questions.  Want to be featured as a guest? Sign up here: https://docs.google.com/forms/d/e/1FAIpQLScrwfuBIhL1-eC5V8mUF9GJaKl3U0jI7hIEvake7wAWJF0DaA/viewform #StartupCulture #OrganizationalTransformation #StrategicLeadership

    37 min
  4. Scaling With Courage and Clarity with Allie Danziger of Ascent

    FEB 25

    Scaling With Courage and Clarity with Allie Danziger of Ascent

    Allie Danziger, Chief Marketing Officer of Ascent and former Founder and CEO of Ampersand Professionals, joins us to discuss choosing growth before certainty. From raising her hand during layoffs to selling two companies and stepping into a CMO role, Allie shares what it means to have the courage to lean into discomfort and bet on yourself before you feel ready. Career fluidity, scaling teams with clarity and questioning the way things have always been done is often the beginning of real innovation. Key Takeaways: 00:00 Introduction. 02:24 Raising your hand creates opportunities that others wait for. 10:40 Scaling requires clarity on roles and accountability. 13:04 Consultants accelerate execution when speed matters most. 15:42 Choosing the harder environment fuels long-term growth. 17:52 Discomfort is a signal that growth is happening. 19:00 Developing early talent builds confidence and real capability. 22:56 Saying yes early shapes the trajectory of your career. Resources Mentioned: Allie Danziger https://www.linkedin.com/in/alliedanziger/ Ascent | LinkedIn https://www.linkedin.com/company/ascentfunding/ Ascent | Website https://www.ascentfunding.com AscentUP program https://www.ascentfunding.com/ascentup/learners/ Thanks for listening to “The Courageous Choice.” Be sure to leave us a review and subscribe so you don’t miss any conversations.  For more information, visit gigtalentagency.com or email us at podcast@gigtalentagency.com if you have any questions.  Want to be featured as a guest? Sign up here: https://docs.google.com/forms/d/e/1FAIpQLScrwfuBIhL1-eC5V8mUF9GJaKl3U0jI7hIEvake7wAWJF0DaA/viewform #StartupCulture #OrganizationalTransformation #StrategicLeadership

    25 min
  5. Choosing Clarity Over Comfort in Modern Leadership with Jackson Lynch of Talent Sherpa

    FEB 11

    Choosing Clarity Over Comfort in Modern Leadership with Jackson Lynch of Talent Sherpa

    Clarity at work is rarely about having the perfect answer. More often, it comes from having the courage to say what everyone is already thinking. In this episode, we sit down with Jackson Lynch, Founder and President of Talent Sherpa, to explore why avoiding hard conversations creates confusion, erodes trust and limits performance. Jackson unpacks why transparency is a leadership advantage, how talent density drives business outcomes and what happens when leaders trade comfort for clarity. We also dive into real-world stories from executive roles and large-scale transformations, offering practical insight into how courageous leadership creates momentum, alignment and long-term results.  Key Takeaways: 00:00 Introduction. 01:45 Lack of clarity creates confusion and slows performance. 05:38 Top performers already know the truth, and avoiding it hurts performance. 10:22 An A player is defined by the role and outcomes, not the individual alone. 14:36 Productive meetings feel uncomfortable because real debate builds trust. 19:46 Honest transparency builds trust, even with hard messages. 22:10 Leaders must communicate with clarity, outcomes and decision rights. 25:28 Sidestepping tough questions delays the truth people deserve. 27:53 Work isn’t about comfort, it’s about clear standards and delivering outcomes. Resources Mentioned: Jackson Lynch https://www.linkedin.com/in/jxnlynch/ Talent Sherpa | LinkedIn https://www.linkedin.com/company/mytalentsherpa/ Talent Sherpa | Website https://www.mytalentsherpa.com Jackson Lynch Substack https://jacksonlynch.substack.com Talent Sherpa Podcast https://www.mytalentsherpa.com/podcast Thanks for listening to “The Courageous Choice.” Be sure to leave us a review and subscribe so you don’t miss any conversations.  For more information, visit gigtalentagency.com or email us at podcast@gigtalentagency.com if you have any questions.  Want to be featured as a guest? Sign up here: https://docs.google.com/forms/d/e/1FAIpQLScrwfuBIhL1-eC5V8mUF9GJaKl3U0jI7hIEvake7wAWJF0DaA/viewform #StartupCulture #OrganizationalTransformation #StrategicLeadership

    31 min
  6. Hiring With Precision: Building Leadership Teams Through Partnership with Amy Sulgrove of Talent Executives Group

    JAN 28

    Hiring With Precision: Building Leadership Teams Through Partnership with Amy Sulgrove of Talent Executives Group

    Making the courageous choice in hiring means looking beyond the résumé and building the support that leaders need in order to win from day one. In this episode, we’re joined by Amy Sulgrove, CEO of Talent Executives Group, to explore what it really takes to place leaders who can thrive in uncertainty, build trust fast and drive performance without losing the human connection. We also unpack why executive hiring cannot end on a start date and how the right support in the first 90 days can make or break long-term success. Key Takeaways: 00:00 Introduction. 01:54 Amy launched Talent Executives Group to build real leadership partnership. 04:56 Amplify Executive Search is a collaboration between Talent Executives Group and Gig Talent Collective. 10:16 Jamie reached out and it became an amazing reconnection after many years. 12:35 Cross-functional influence is the leadership capability in highest demand. 15:24 Leaders can handle ambiguity while creating clarity, and Gig Talent helps. 18:04 AI is reshaping hiring and leaders need to validate what is real. 20:51 Zoom interviews get gamed when candidates use earpieces for answers. 23:43 Saying yes to everything hurts precision, so focus on excellence. Resources Mentioned: Amy Sulgrove https://www.linkedin.com/in/amysulgrove/ Talent Executives Group | LinkedIn https://www.linkedin.com/company/talentexecutives/ Talent Executives Group | Website https://talentexecutivesgroup.com/ Thanks for listening to “The Courageous Choice.” Be sure to leave us a review and subscribe so you don’t miss any conversations.  For more information, visit gigtalentagency.com or email us at podcast@gigtalentagency.com if you have any questions.  Want to be featured as a guest? Sign up here: https://docs.google.com/forms/d/e/1FAIpQLScrwfuBIhL1-eC5V8mUF9GJaKl3U0jI7hIEvake7wAWJF0DaA/viewform #StartupCulture #OrganizationalTransformation #StrategicLeadership

    26 min
  7. The Power of Courageous Career Moves: Building Gig Talent With Purpose with Jamie Latiano Jacobs of Gig Talent

    JAN 14

    The Power of Courageous Career Moves: Building Gig Talent With Purpose with Jamie Latiano Jacobs of Gig Talent

    There comes a moment when success looks right on paper but feels wrong in practice. In this episode, we sit down with Jamie Jacobs, Founder and CEO of Gig Talent, for a candid conversation about ambition, fear, alignment and what it truly means to make a courageous choice. Jamie reflects on her personal and professional evolution, from corporate leadership to building a company rooted in flow, purpose and community. Her story highlights how courage is not the absence of fear, but the willingness to move forward anyway and create possibilities that didn’t exist, or you couldn’t see, before.  Key Takeaways: 00:00 Introduction. 03:32 Ambition often follows the next visible step before the bigger picture appears. 05:09 Growth and curiosity, not money, drive ambition beyond perceived personal limitations. 10:15 Resistance signals misalignment despite persistence and fear of failure. 12:27 Jamie values contributing to communities and learning to accept support. 15:39 Gig Talent launched in 2019 with the aim of aligning strengths and creating shared value. 18:09 Leveraging AI strengthens Gig Talent’s expertise while preserving human-led matching. 20:06 Every step has value and fear should never dictate when to move on. 21:20 Courage in two words: do it. Resources Mentioned: Jamie Jacobs https://www.linkedin.com/in/jlatianojacobs/ Gig Talent | LinkedIn https://www.linkedin.com/company/gig-talent/ Gig Talent | Website https://gigtalentagency.com/ Thanks for listening to “The Courageous Choice.” Be sure to leave us a review and subscribe so you don’t miss any conversations.  For more information, visit gigtalentagency.com or email us at podcast@gigtalentagency.com if you have any questions.  Want to be featured as a guest? Sign up here: https://docs.google.com/forms/d/e/1FAIpQLScrwfuBIhL1-eC5V8mUF9GJaKl3U0jI7hIEvake7wAWJF0DaA/viewform #StartupCulture #OrganizationalTransformation #StrategicLeadership

    24 min
  8. Building a Human-Centered Workforce in the Age of AI with Edie Goldberg of E. L. Goldberg & Associates

    12/17/2025

    Building a Human-Centered Workforce in the Age of AI with Edie Goldberg of E. L. Goldberg & Associates

    As the world of work rapidly evolves, it demands new approaches to talent, performance and career growth. In this episode, we speak with Edie Goldberg, President and Founder of E. L. Goldberg & Associates, to explore how organizations can adapt to evolving employee expectations, leverage AI for talent strategies and create environments that enable people to thrive.  Key Takeaways: 00:00 Introduction. 01:14 The future of work requires disrupting outdated talent practices with AI. 05:44 Disrupting outdated processes is key to attracting, engaging and retaining talent. 10:22 Companies must tap into diverse talent beyond employees. 17:03 Aging populations and shifting demographics demand more flexible work options. 20:06 Tenure boosts productivity through relationships and knowledge. 25:10 Curiosity and continuous learning are essential for thriving today. 30:21 Diverse perspectives fuel innovation and better solutions. 34:01 Turning a layoff into a successful business was a defining act of courage. Resources Mentioned: Edie Goldberg https://www.linkedin.com/in/edie-goldberg-phd/ E. L. Goldberg & Associates | LinkedIn https://www.linkedin.com/company/e-l-goldberg-associates/ E. L. Goldberg & Associates | Website https://www.elgoldberg.com/ "The Inside Gig" by Edie Goldberg https://theinsidegig.com/ Thanks for listening to “The Courageous Choice.” Be sure to leave us a review and subscribe so you don’t miss any conversations.  For more information, visit gigtalentagency.com or email us at podcast@gigtalentagency.com if you have any questions.  Want to be featured as a guest? Sign up here: https://docs.google.com/forms/d/e/1FAIpQLScrwfuBIhL1-eC5V8mUF9GJaKl3U0jI7hIEvake7wAWJF0DaA/viewform. #StartupCulture #OrganizationalTransformation #StrategicLeadership

    36 min
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5
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About

Every breakthrough begins with a decision — a moment of hesitation followed by a leap. “The Courageous Choice” is the podcast that explores those defining moments when leaders, entrepreneurs, changemakers, and individuals bet on themselves, defy expectations, and step into the unknown. Hosted by Jamie Jacobs, founder and CEO of Gig Talent, each episode explores bold career moves and industry-shaping innovations. We dive into the risks, the resilience, and the rewards that come with making the courageous choice.

Information

  • Creator
    WRKdefined Podcast Network
  • Years Active
    2025 - 2026
  • Episodes
    22
  • Rating
    Clean
  • Copyright
    © All rights reserved by WRKdefined
  • Show Website
    The Courageous Choice