Ryan Isaac is an education fundraiser & longtime baseball insider who spent more than a decade working in professional baseball. In this episode, Ryan shares how he broke into the industry, what it was like navigating the uncertainty & mobility of baseball careers, and why becoming a parent ultimately reshaped his priorities. He reflects on the identity shift that comes with leaving a dream job and finding new ways to stay connected to the work you love. The conversation also explores how Ryan rediscovered his voice through writing and launched his baseball newsletter, Warning Track Power, as a creative outlet beyond his day job.

Ryan's question for Tim: What was the biggest obstacle you faced during your career transition? 

Key takeaways:

1. Ryan shares his early career ambitions as a writer and journalist, including working at Wine Spectator in New York City while nurturing a long-standing passion for baseball. 
2. He describes leaving journalism to pursue a career in professional baseball during the early “Moneyball era,” including moving to San Diego without a job lined up to put himself closer to opportunity. 
3. Ryan recounts how a chance phone call led to his first full-time role with the San Diego Padres, marking his official entry into Major League Baseball operations. 
4. After leaving baseball, Ryan transitioned into fundraising for an independent school, gradually building experience through expanded responsibilities during the early COVID period. 
5. During the pandemic, Ryan reignited his creative outlet by writing about baseball, leading to the launch of his newsletter Warning Track Power as a personal and intellectual release.

Links:
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