Episode Summary
Executive Summary: Jason Pfeiffer argues that change creates opportunity if leaders and individuals adapt quickly, define themselves by transferable values, and treat careers as experiments. He explains his "build for tomorrow" mindset through history, his own career moves, and practical leadership advice on communicating change, embracing discomfort, and focusing on opportunity set B to future-proof growth.
Main Topics: Change as opportunity, not threat: Using the bubonic plague as an example, Pfeiffer shows how disruptive events can reshape systems and create new economic and career opportunities, and argues that once change is here, leaders should focus on what it enables. Identity beyond the job title: Pfeiffer advises defining yourself with a transferable one-sentence mission that is not tied to a single employer or role, so career shocks do not erase your sense of value. Career strategy: skill-building and opportunity set B: He describes building a career by learning specific skills in each role, then seeking extra responsibilities and side projects that expand future options beyond current job requirements. Leading teams through change: He outlines how managers should announce change: acknowledge that employees had less time to process it, explain the value, start with the audience's perspective, and frame the change as a better version of something familiar. Willingness to be bad before being good: Pfeiffer relays Ryan Reynolds' insight that success in new endeavors requires tolerating initial incompetence long enough to improve. Learning from failure and sustaining excellence: Through stories about The Rock and other high performers, he argues that adaptable leaders are self-aware, learn from mistakes, and turn low moments into growth moments.
Key Arguments: Major disruptions can produce structural benefits, so leaders should stop resisting the fact of change and instead ask what new opportunities it creates. A stable career depends on a transferable identity statement, not on anchoring the self to a role that can disappear overnight. Professional growth comes from understanding what you need to learn next, not just chasing the next promotion or title. Opportunity set A is the work assigned to you; opportunity set B is the unassigned work, side projects, and learning experiences that create future advancement. When communicating change, start with the recipient's current reality, values, and familiarity rather than with the company's excitement about the change. People generally resist new things but embrace better versions of things they already understand. To get good at anything new, you must accept being bad long enough to build competence. Long-term excellence is driven by adaptability, self-awareness, and the ability to convert mistakes into lessons and service to others.
Data Points: Europe population affected by bubonic plague: upwards of 60% - Pfeiffer uses this estimate to explain how the plague created a labor shortage that changed employment relationships Career start year: 2002 - He says he graduated college in 2002 and began in newspaper journalism Current age mentioned: 42 years old - He identifies his age while describing his career path Number of newspaper jobs he quit early in his career: 2 - He says he quit two newspaper jobs to pursue freelancing Time at Entrepreneur before editor-in-chief role: 9 months - He took the executive editor job in 2015 and made a play for editor-in-chief nine months later Brand age: 40-something years - He says Entrepreneur has existed for over four decades and needed a broader audience view Recommendation text line: Text Hawk to 66866 - Promotional call to join Mindful Monday and receive email updates Audience size reference: tens of thousands - Used to describe the number of Learning Leader subscribers receiving the Monday email Book title: Build for Tomorrow - Jason Pfeiffer's book on embracing change and future-proofing a career
Pivotal Quotes: "People hate new things, but they love better versions of old things." — Jason Pfeiffer: Advice on how managers should frame change so teams can accept it more easily "Don't ask for an opportunity, be the opportunity." — Jason Pfeiffer: His core idea for career advancement and leadership value creation "In order to be good at something, you have to be willing to be bad." — Ryan Reynolds: A lesson Pfeiffer shared about learning new skills and tolerating early failure
Implications: Listeners should treat disruption as a catalyst, build transferable value, and lead change by starting from others' perspective. Careers and organizations grow faster when people seek unassigned opportunities, learn continuously, and reframe fear as part of the process.
About The Learning Leader Show With Ryan Hawk
View all episodes from The Learning Leader Show With Ryan Hawk