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7 Podcasts that will Help You Tune into a Fulfilling Career Transition

  • Writer: Kristin Schuchman
    Kristin Schuchman
  • Sep 30, 2025
  • 4 min read

Updated: Oct 29, 2025

Listen and learn to strategies to ease the discomfort of your next career change


The moment you begin contemplating a professional pivot, the path ahead can feel like an unfamiliar wilderness. Information is everywhere, but genuine, actionable wisdom—the kind that guides you from "what if" to "what next"—is elusive. Podcasts can also be an excellent resource for individuals looking to advance their careers. From interviews with successful professionals to discussions of the latest trends and insights, podcasts provide a wealth of information and inspiration for anyone looking to stretch themselves professionally. Below is curated a list of essential podcasts that cut through the noise.

Podcasts for a fulfilling career transition


1. Pivot with Jenny Blake: Your Strategic Podcast for a Career Transition


Though currently on hiatus, Jenny Blake's "Pivot" podcast is a consistently insightful resource for anyone contemplating a career move, big or small. Blake, a former Google career coach, offers practical strategies, actionable frameworks, and interviews with individuals who have successfully navigated their own pivots. She delves into topics like identifying your transferable skills, managing fear and uncertainty, and building momentum towards your new goals. Think of it as your personal career strategy session, available whenever you need it.


Portland Connection: While Blake isn't based in Portland, her pragmatic and forward-thinking approach resonates with the city's strong entrepreneurial and creative spirit. Her emphasis on skill-building and adaptability aligns perfectly with the mindset of many Portland professionals considering a change.


2. The Tim Ferriss Show: Deconstructing Success Across Industries

While not exclusively focused on career change, Tim Ferriss's long-form interviews with high-achievers across diverse fields offer invaluable insights into different career paths, skillsets, and ways of working. Hearing the origin stories and daily routines of successful entrepreneurs, artists, and thought leaders can spark new ideas and help you identify what truly resonates with you. Plus, Ferriss often dives deep into practical tools and strategies for learning new skills and optimizing performance – essential for any career transition.


Portland Connection: Portland's vibrant and eclectic professional landscape mirrors the diverse range of guests on Ferriss's show. His focus on unconventional paths and "lifestyle design" often aligns with the independent and purpose-driven ethos found throughout the Rose City. He also used to host an annual conference for and by unconventional thinkers called The World Domination Summit in Portland with pal Chris Guillebeau but ended the event in 2022.


3. Second Life by Hillary Kerr (Who What Wear Co-Founder): Inspiring Stories of Career Reinvention


Hillary Kerr is the co-founder of the influential fashion website Who What Wear but has since launched the Second Life podcast, which features candid conversations with successful women who have made significant career changes. Hearing firsthand accounts of the challenges, triumphs, and unexpected twists involved in these transitions can be incredibly motivating and provide valuable lessons learned. It's a reminder that career paths are rarely linear and that reinvention is often the key to long-term fulfillment.


4. The Happiness Lab with Dr. Laurie Santos: Understanding Your Values and Motivation

Before making any drastic career moves, it's crucial to understand what truly drives you and what contributes to your overall well-being. Dr. Laurie Santos, a Yale professor, delves into the science of happiness, offering evidence-based insights into how to cultivate more joy and fulfillment in your life. This podcast can help you clarify your values and identify the types of work and environments that are most likely to lead to long-term satisfaction, regardless of the specific industry.


5. The School of Greatness by Lewis Howes: Inspiration for a Life Reimagined


Lewis Howes' The School of Greatness is an expansive podcast featuring interviews with successful entrepreneurs, athletes, authors, and thought leaders. While not solely focused on career change, it consistently provides a massive dose of inspiration and practical advice on mindset, overcoming fear, and pursuing a life of purpose. Listening to diverse success stories can help you redefine what's possible for your own professional journey.

6. The Career Advancement Show by Career Contessa: Actionable Steps for Your Next Move


The Career Advancement Show from Career Contessa provides tactical, actionable advice for women (and anyone, really) looking to grow in their careers, which often includes making a strategic pivot. This podcast covers everything from negotiating salaries and networking to identifying new career paths and building essential skills. With no-nonsense advice, humor, and fresh takes on unconventional topics, The Career Advancement Show is a great podcast for concrete steps when you’re not just thinking about a career transition, but actively planning one.


7. Find Your Dream Job by Mac Prichard: Practical Strategies for the Job Search


Once you've done some soul-searching, "Find Your Dream Job" by Mac Prichard of Mac’s List offers a more direct, how-to guide for the actual job search. Pritchard delivers practical advice on resume writing, interviewing, networking, and leveraging online tools. If your contemplation leads to a firm decision to move, this podcast helps bridge the gap between introspection and execution.


Portland Connection: Mac's List is a Portland-based job board and career resource that connects job seekers with purpose-driven opportunities in Oregon and Southwest Washington. Host Mac Prichard founded Mac’s List before launching the Find Your Dream Job podcast, which boasts a national audience and focuses on standing out and effectively navigating the application process provides essential tools for job seekers in competitive job markets eager to land their ideal next role.


Contemplating a career change is overwhelming, but you don't have to navigate it alone. Podcasts like these demonstrate how other people in similar situations explored various options to eventually find meaning and fulfillment in their careers. So, indulge in your activity of choice while listening to podcasts – take a hike, unload the dishwasher, lounge in the backyard – as you strategically contemplate your next steps.


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Kristin Schuchman, MSW is a career counselor, business coach, and author based in Portland, Oregon who works with creative and mission-driven professionals. She writes resumes and coaches individuals seeking support for career indecision, next steps, work re-entry, advancement, starting a business, and work-life-balance. She offers a free 30-minute Zoom or phone session and presently works with clients in-person in Portland and remotely. You can find her books The DIY Website Workbook and Jump Start: How to redirect a career that has stalled, lost direction or reached a crossroads on Amazon.


2 Comments


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Jun 17

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