Jason Feifer started his career writing about middle school dances at a tiny local newspaper, frustrated and convinced he was capable of more. Stuck in a role that wasn’t moving him forward, he quit, sat in his dumpy apartment next to a graveyard, and began cold-pitching major publications with no connections. That decision transformed his trajectory, eventually leading him to become Editor-in-Chief of Entrepreneur Magazine and a leading voice on career growth and adaptability. In this episode, Jason chats with Ilana about why doing only what’s expected of you slows your growth, how to identify opportunities, and steps to take control of your career in an unpredictable world.

Jason Feifer is the Editor-in-Chief of Entrepreneur Magazine, a podcast host, book author, and keynote speaker who helps people build careers and companies they love by sharing lessons from the world's top entrepreneurs and leaders.

In this episode, Ilana and Jason will discuss:

(00:00) Introduction 

(03:48) Cold Pitches From a Bedroom Next to a Graveyard

(06:41) Developing an ‘Opportunity Set B’ Mindset

(09:51) Building Skills Strategically Across Jobs

(12:58) Renting a Title vs. Owning Your Name

(17:02) The Mission Statement That Survives Any Job Loss

(24:22) Why Jason Walked Away From His Biggest Hit

(31:51) How to Test Multiple Ventures At Once

(34:31) How a Lawsuit Accidentally Built Jason’s Success

(40:00) The Danger of Labeling Yourself

(47:47) Q&A: How Do You Become More Adaptable?

Jason Feifer is the Editor-in-Chief of Entrepreneur Magazine, a role he has held for over 10 years. He is the author of Build for Tomorrow, host of the podcast Help Wanted, and a sought-after keynote speaker who has spoken for companies including Pfizer, Alibaba, Clorox, and more. Jason also advises startups, sits on multiple advisory boards, and writes the weekly newsletter One Thing Better. His work centers on adaptability, personal reinvention, and helping individuals and organizations thrive through change.

Connect with Jason

Jason’s Website: https://www.jasonfeifer.com 

Jason’s LinkedIn: linkedin.com/in/jasonfeifer 

Jason’s Instagram: https://www.instagram.com/heyfeifer/

Resources Mentioned:

Jason's Newsletter, One Thing Better: https://www.jasonfeifer.com⁠ 

Jason’s Book,

Build for Tomorrow: An Action Plan for Embracing Change, Adapting Fast, and Future-Proofing Your Career:

https://www.amazon.com/dp/059323538X

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