Feeling stuck after a sudden job loss or career shift? Get inspired by a real-life story of resilience, reinvention, and the pursuit of purpose.
On this episode of Looking Forward Our Way, hosts Brett Johnson and Carol sit down with Randy Robertson, who candidly shares how he navigated an unexpected end to his 30-year corporate journey and found new meaning as a regional storyteller at Special Olympics New York.
From managing global creative teams to rediscovering his early love for writing, Randy walks us through his step-by-step approach to tackling unemployment, overcoming self-doubt, and building an authentic new career path.
Learn firsthand how Randy harnessed the power of networking (both online and in person), leveraged learning platforms and job resources, and turned personal experiences—including those with his adult daughter living with autism—into a powerful storytelling platform that helps others. You’ll come away with real strategies you can use, no matter where you are in your career journey.
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Key Takeaways:
- How to approach sudden job loss with resilience and a proactive mindset
- Practical tactics for networking, using LinkedIn, and making coffee chats count
- Embracing new skills and staying technologically relevant at any age
- Leveraging personal experience and unfinished business in creating a meaningful career pivot
- The value of community support, volunteering, and purpose-driven work
If you’re facing a career crossroads, feeling stuck, or hunting for inspiration to reignite your professional life, this conversation is a must-listen.
Frequently Asked Questions
Who is Randy Robertson and what is his role at Special Olympics New York?
Randy Robertson is a regional storyteller for Special Olympics New York. He previously worked for 30 years in global creative services for a business consulting firm, and now shares stories about Special Olympics athletes and events, focusing on the special needs community 00:20, 29:44.
What role did networking and LinkedIn play in his career transition?
Networking—both direct outreach on LinkedIn and personal connections—was crucial. Randy Robertson messaged hundreds of contacts and found many were receptive and willing to help.
How did Randy Robertson approach learning new skills and technology?
He used online resources like LinkedIn Learning, took targeted courses (such as SEO and WordPress), and embraced new tools relevant to his evolving career goals.
What is Randy’s blog “Life with Mary” about, and how does it support the special needs community?
“Life with Mary” is Randy’s Substack blog sharing stories about daily life with his daughter Mary, who has moderate autism. The blog provides insights for families with special needs children and raises awareness for both those inside and outside the autism community 19:13–21:17, 31:03–41:33.
What advice does Randy Robertson offer older job seekers facing a career pivot?
Focus on networking, don’t hesitate to reach out to contacts, use job boards for research (not as your only strategy), and be open to reimagining what fulfilling work might look like in your next chapter.
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Recorded in Studio C at 511 Studios. A production of Circle 270 Media® Podcast Consultants.
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Copyright 2026 Carol Ventresca and Brett Johnson
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Listener Disclaimer
The views and opinions expressed by the experts interviewed on this podcast are their own and do not necessarily reflect the views of the podcast hosts or any affiliated organizations. The information provided in these interviews is for general informational purposes only and should not be considered as professional advice. Listeners are encouraged to consult with qualified professionals for specific advice or information related to their individual circumstances. The podcast host and producers do not endorse or guarantee the accuracy, completeness, or reliability of any information provided by the experts interviewed. Listener discretion is advised.
