The Courageous Choice

Jamie Jacobs (Gig Talent)
  • 5.0 (7)
  • MANAGEMENT
  • UPDATED BIWEEKLY

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

    2D AGO

    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
  2. 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
  3. 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
  4. 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
  5. From Burnout to Breakthrough: Transforming Workplaces Through Wellbeing with Ashish Kothari of Happiness Squad

    12/03/2025

    From Burnout to Breakthrough: Transforming Workplaces Through Wellbeing with Ashish Kothari of Happiness Squad

    The path to happiness often begins with the courage to make a change. In this episode, we sit down with Ashish Kothari, Founder and CEO of Happiness Squad, to explore how redefining success, shifting workplace mindsets and building human-centric systems can unlock both individual and organizational potential. Ashish shares his deeply personal journey from corporate leadership to founding Happiness Squad, offering transformative insights on wellbeing, leadership and the future of work. He explains why flourishing must become a strategic priority, how organizations can tackle burnout at source and how leaders at every level can create meaningful change.  Key Takeaways: 00:00 Introduction. 01:09 A battle with anxiety inspired Ashish to pivot his career toward well-being. 05:22 Ashish says his calling, not courage, drove his career transformation. 10:06 Burnout is often worse in nonprofit and frontline roles than in corporate jobs. 15:02 Trust, belonging and deep work fuel human energy. 19:58 One-size-fits-all programs fail; teams need tailored interventions. 25:34 Leaders can drive systemic change without top-level support. 29:59 The Eisenhower Matrix helps reset priorities and reduce overwhelm. 32:36 People want to contribute, but broken systems create changeable helplessness. Resources Mentioned: Ashish Kothari https://www.linkedin.com/in/ashishkothari1/ Happiness Squad | LinkedIn https://www.linkedin.com/company/happiness-squad/ Happiness Squad | Website https://happinesssquad.com/ VIA Character Strengths https://www.viacharacter.org/ World Economic Forum https://www.weforum.org/ 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 #BusinessGrowth

    36 min
  6. Guiding Owners Through Hospitality Transitions with Vikram Sood of NuPala Hospitality Development

    11/12/2025

    Guiding Owners Through Hospitality Transitions with Vikram Sood of NuPala Hospitality Development

    Success in hospitality, like in life, often comes down to making the courageous choice. In this episode, we sit down with Vikram Sood, Managing Director of NuPala Hospitality Development, to discuss the pivotal choices that defined his journey, the lessons learned in hospitality and the importance of resilience in uncertain times. We explore what it means to take courageous steps in both career and life. From global luxury hotels to independent consulting, Vikram shares how bold decisions shape leadership, culture and long-term growth. Key Takeaways: 00:00 Introduction. 01:26 Reopening a long-dormant resort reshaped San Diego’s luxury scene. 05:13 Moving to Las Vegas revealed a shift from luxury hospitality to gaming priorities. 10:12 Guiding owners through new builds and strategic transitions became his focus. 14:20 Courageous choices evolve, from early experimentation to confident decisions later in life. 16:23 Rising wage ordinances challenge leaders to do more with less. 18:26 True leadership is measured by impact on people, not prestigious titles. 20:02 Entrepreneurship demands backbone, faith and resisting the easy route. 22:41 Passion, not pedigree, should guide careers through uncertainty and change. Resources Mentioned: Vikram Sood https://www.linkedin.com/in/vikram-sood-33462610/ NuPala Hospitality Development https://www.linkedin.com/company/nupala-hospitality-development/ Four Seasons Hotels and Resorts https://www.fourseasons.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 #BusinessGrowth

    24 min
  7. The Future of HR: Building a Bold, Human-Centered Approach to Hiring with Tim Sackett of HR Tech 100 Fund

    10/22/2025

    The Future of HR: Building a Bold, Human-Centered Approach to Hiring with Tim Sackett of HR Tech 100 Fund

    The rapid rise of AI is reshaping how organizations approach hiring, talent management and leadership. In this episode, we sit down with Tim Sackett (Not a Life Coach), General Partner and Co-Founder at HR Tech 100 Fund, to discuss the courageous decisions companies and recruiters must make to stay ahead in a rapidly changing talent landscape. Tim shares candid insights into how technology, human connection and cultural clarity intersect to shape the future of recruiting, and why courage is more vital than ever for leaders, recruiters and employees alike. Key Takeaways: 00:00 Introduction. 02:35 AI is doubling applicant volumes and reshaping the recruiting process. 05:14 Recruiters must overcome rejection and have the courage to pick up the phone. 10:20 Making people feel valued and wanted is a powerful part of recruiting. 15:27 Digging into passions and cultural fit is just as important as evaluating skills. 20:56 Driving meaningful change takes courage, even when the risks feel high. 25:03 Knowing recruiting capacity empowers leaders to set realistic expectations. 30:05 Patience is a crucial leadership skill, especially during change. 32:31 Helping others defines success more than titles or identity. Resources Mentioned: Tim Sackett https://www.linkedin.com/in/timsackett/ HR Tech 100 Fund | LinkedIn https://www.linkedin.com/company/hrtech100/ HR Tech 100 Fund | Website https://hrtech100fund.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 #BusinessGrowth

    34 min
  8. The Future of HR: Elevating HR Through Courage and Strategy with Dr. JP Elliott of Future of HR Consulting

    10/08/2025

    The Future of HR: Elevating HR Through Courage and Strategy with Dr. JP Elliott of Future of HR Consulting

    The future of HR requires bold choices and the willingness to step into uncertainty. In this episode, JP Elliott, Founder of Future of HR Consulting, explores how courage shapes leadership, careers and the evolving workplace. JP shares his journey from corporate HR leadership roles to building a global podcast and launching the NextGen HR Accelerator. Together, we examine how HR leaders can make courageous choices in the face of technological disruption, shifting expectations and the rise of AI. Key Takeaways: 00:00 Introduction. 02:24 JP shares how 20+ years in HR led him to launch “The Future of HR Podcast.” 04:54 HR leaders must invest in themselves as expectations rise. 10:48 Insights from 150 interviews shaped a framework for great HR leadership. 14:48 The future path to CHRO remains uncertain as technology reshapes the role. 16:10 HR leaders must share tough perspectives, backed by deep business understanding. 17:54 Courage is giving yourself permission to ask hard questions. 20:18 The most courageous choice ahead is investing in yourself. 22:44 Action beats reflection — courage comes from taking the first step. Resources Mentioned: JP Elliott https://www.linkedin.com/in/jpelliottphd/ Future of HR Consulting | LinkedIn https://www.linkedin.com/company/future-of-hr-consulting/ Future of HR Consulting | Website https://www.futureofhr.com/ “The Future of HR Podcast” https://podcasts.apple.com/us/podcast/future-of-hr/id1644712611 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 #BusinessGrowth

    23 min
See All (18)

5
out of 5
7 Ratings

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
    Jamie Jacobs (Gig Talent)
  • Years Active
    2025 - 2026
  • Episodes
    18
  • Rating
    Clean
  • Copyright
    © Copyright 2025
  • Show Website
    The Courageous Choice