The Courageous Choice
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.
Episodes
June 19, 2026 • 24 mins
This conversation breaks down why so many AI and automation investments fail inside organizations, and what to do instead. The core idea: companies keep layering new tools on top of processes they don't actually understand end to end, which leads to wasted spend, poor workforce planning, and avoidable layoffs.
You'll learn how to audit the technology you already own, measure usage on a much faster cadence, and redesign work s...
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June 3, 2026 • 37 mins
This episode breaks down why so many organizations struggle to adopt AI and manage change, and what leaders can actually do about it. You will learn why readiness matters more than enthusiasm, why AI adoption cannot be measured like traditional software, how to get genuine buy-in before launching a transformation, and why copying another company's culture almost always backfires. It is a candid conversation about leadership, honest...
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May 20, 2026 • 20 mins
Most companies treat AI as a cost-cutting tool, but the real competitive advantage comes from using it to create new products, services, and capabilities. In this conversation, Pedro Arellano, founder of Wallabi, explains the framework of dual transformation and why business leaders who only optimize existing processes will fall behind.
In this episode, you will learn why AI transformation is not a technology project, how to bui...
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May 5, 2026 • 29 mins
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 episod...
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April 20, 2026 • 34 mins
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 ...
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March 11, 2026 • 37 mins
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 ...
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February 25, 2026 • 26 mins
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 th...
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February 11, 2026 • 31 mins
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 outcom...
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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 ...
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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 highl...
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December 17, 2025 • 36 mins
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 ...
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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 ins...
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November 12, 2025 • 24 mins
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 t...
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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 int...
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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 te...
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September 24, 2025 • 37 mins
The role of HR continues to evolve, yet ambiguity still surrounds its true impact at the executive level. In this episode, we sit down with John Boudreau, Author, Speaker, Coach, Consultant and Advisor at Dr. John W Boudreau, to explore how courage and clarity can reshape the CHRO’s position in modern organizations. John reflects on four decades of research and advisory work, offering a framework for how HR leaders can define...
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September 10, 2025 • 28 mins
Courage doesn’t always show up with noise. Sometimes it’s quiet, intentional and rooted in knowing where we stand. In this episode, Susan Kelliher, Founder/Principal of Sentima Advisors LLC and Board Member of the National Safety Council, Airvet and EJ, explores how courage shows up in the workplace — whether in the boardroom, during sensitive conversations or in moments of personal growth. With a career shaped by...
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Leadership today requires more than just strategy — it demands grace, courage and a willingness to let go of outdated norms. In this episode, we sit down with Dr. David Blake, Chief Executive Officer of Building Forward Now, and author of "Leading With Grace," to explore how leaders can liberate others, lead authentically and make bold, meaningful transitions in their careers. David reflects on lessons from the military, the ...
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August 6, 2025 • 35 mins
Courage isn't always loud — it often shows up in quiet moments of truth-telling, tough decisions and choosing impact over approval. In this episode, we speak with Ian Ziskin, President of EXec EXcel Group LLC, to reflect on decades of HR leadership, executive coaching, and organizational transformation. Ian shares insights on leadership, building trust and how courageous choices define a legacy. We also explore the fine balan...
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July 23, 2025 • 31 mins
Leaders often face pivotal moments that call for courage, resilience and reinvention. In this episode, we speak with Kip Knight, Founder of CMO Coaches. He shares hard-won leadership lessons from his career across iconic companies and how he knows taking leaps of faith can be transformative. Kip reflects on what it means to lead with integrity, how to navigate change, and the importance of authenticity, gratitude, and risk-taking &...
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