In this episode of “Between Over and Next,” hosts Holli and Robert interview Howard Waldstreicher, fondly referred to as Howie, whose remarkable career transition unfolds a narrative of relentless pursuit and adaptation. After a notable stint as a software engineer and a successful career as an entrepreneur, Howard shifted gears and landed a job after a 20-year hiatus from the information technology world eventually becoming the oldest intern at Facebook, which led him to author his book, “Facebook’s Oldest Intern.” He rekindled his programming skills to re-enter the workforce amidst challenging dynamics, personifying the drive to thrive against all odds.

Howard shares his inspiring journey of reinvention and discusses the obstacles he overcame, the lessons he learned, updating a 20-year-old resume, and adapting to radically different corporate cultures, poignantly described through his interview experiences and eventual success landing a role in the titan of social media—Facebook/Meta. Through determination and an unyielding spirit, Howie demonstrates that possibilities are boundless, irrespective of age. Howard’s story is a powerful reminder that it’s never too late to pursue your dreams and embrace new opportunities. To learn more about his transformational story, be sure to listen to the full episode.

00:00 Introduction to the podcast and guest, Howard Waldstreicher 04:25 Howard’s motivation for writing the book and inspiring others 05:26 Overcoming obstacles in switching careers and reentering the workforce 08:11 Howard’s strategy for interviewing and comparing the experience to 30 years ago 09:03 Howard’s successful job offer and the excitement of working at Facebook 10:25 The unique cohort experience and diversity at Facebook 10:52 Adjusting to the culture and differences between Facebook and previous workplaces 11:51 Comparing the strict culture at EDS to the relaxed culture at Facebook 11:55 Howard talks about the differences between working at Facebook and other companies 12:15 Robert discusses the challenges of corporate bureaucracy 12:50 Howard mentions the oddities of office interaction at Facebook 13:55 Howard takes control of a meeting and highlights communication challenges 14:46 Howard discusses the difficulties of communicating through text messages 15:17 Howard shares his biggest lesson from working at Facebook 16:30 Howard reflects on how his entrepreneurial background helped him succeed 16:52 Robert asks if the 30-year-old Howard could have gotten the job 17:30 Howard explains how being older and wiser worked to his advantage 18:03 Howard shares what inspires him 18:17 Howard discusses his plans for the future 19:24 Holli acknowledges the impact Howard made at Facebook 20:09 Howard advises listeners not to act or look old 20:34 Robert discusses the impact of age discrimination in job interviews 22:00 Holli emphasizes the importance of adapting to corporate culture 22:50 Holli encourages listeners to embrace new opportunities 23:24 Robert highlights the power of networking 23:46 Holli concludes by emphasizing the importance of pursuing dreams at any age 23:24 Robert emphasizes the power of connections and networks 24:10 Holli highlights the importance of asking for what you want 25:42 Robert explains the challenges of relating to different generations 26:13 Holli praises Howie for self-publishing a book 26:31 Robert discusses the accessibility of self-publishing in the digital age 28:06 Contact information and request for feedback 28:33 Conclusion and closing remarks

Key Takeaways:

1. Embracing change and taking risks are key to navigating career transitions, regardless of age.
2. Networking and leveraging connections remain crucial, though they may not always yield immediate results.
3. The ability to adapt to new working environments and reimagine your skillset is pivotal in today’s job market.
4. Howard’s experience underscores the importance of opening up to learning and continuous growth.
5. Age should not define or limit potential; it can indeed align with new opportunities and successes.

Howard’s Notable Quotes:

“It’s not easy, but you can do it. And I was proof that you can do it.” – Howard on reinventing oneself. “I felt I could motivate people and inspire… It just becomes harder as you get older, can you do it? Do you believe you can? And I did it.” – Howard when asked about why he wrote his book. “What they don’t have, and what I brought to the table, was the life experience.” – Howard on what set him apart in the workforce.