Insights and Inspiration from Randy Robertson’s Journey through Unexpected Change to Creating Impact
Career transitions are rarely easy, especially for those seasoned by decades in a single industry. But they can become a profound opportunity for reinvention, growth, and finding renewed purpose. On this episode of Looking Forward Our Way, Brett Johnson and Carol sat down with Randy Robertson—now Regional Storyteller for Special Olympics New York—to talk about the lessons from his dramatic shift from global creative services leader to nonprofit storyteller, and how embracing curiosity, resilience, and authenticity led him to more meaningful work.
The Shock of Sudden Change
After nearly 30 years managing creative services in a global consulting firm, overseeing teams from Chicago to India, Randy Robertson was abruptly laid off in a “12-minute phone call.” Like many older professionals, he suddenly confronted not just financial and logistical challenges, but a deeper blow to identity and self-worth.
“So much of our identity is tied up in your job,” he reflected, “and it’s even just a little simple comment as you run into somebody at the store like how’s your work going? … Oh, I’m unemployed. Like it’s tough. I haven’t said that in 30 years.”
Rediscovering Skills and Building a Resilient Mindset
Despite the initial shock, Randy Robertson found grounding in both practical resources and his supportive network. With his wife’s job covering benefits and a severance package providing a financial buffer, he had a window to focus on his next steps.
Drawing on a vast LinkedIn network built over years, hundreds of colleagues across industries, he reached out, often to people he barely knew. The response was heartening: “Some sent me links to their new companies, job classified web pages … some set up 15-30 minute phone calls. … I was amazed how many people did give me 15 minutes, 30 minutes, whatever.”
He also encountered a humbling reality: after submitting dozens of applications to roles similar to his old one, most resulted in silence or form rejections. “It got very demoralizing … you do have to kind of say, you know, what do I want to do?”
From Reinvention to Rediscovery: Rekindling a Long-Lost Passion
A turning point came from an unexpected source: a podcast about “unfinished business.” Asked what remained undone in his life, Randy Robertson blurted out, “sports writing,” a passion he’d set aside decades before. With encouragement from his wife, he began writing again. Not for pay at first, but to rebuild confidence and flex creative muscles that had lain dormant. Leveraging AI tools like ChatGPT and publishing on Substack, he began “Life with Mary,” documenting daily life with his autistic daughter.
Not only did the blog help him reconnect with storytelling, but it also created a fresh, current writing portfolio. Essential for pursuing new, writing-focused career options.
Continuous Learning and Embracing Technology
Facing a competitive job market and younger candidates, Randy Robertson recognized that learning new digital skills was vital. “I always pushed [my old team] about adopting more tools and keeping … relevant. But then when I was out on my own, what are the tools [out] there?” He dove into LinkedIn Learning for SEO and WordPress, built a blog with help from AI, and participated in virtual networking groups like “Tuesday Tune Up,” which provided community and accountability.
The Power of Authentic Networking
Through relentless networking, on LinkedIn, in his neighborhood, church, and community, he learned that often “you’re better off asking. And if they don’t have time or they blow you off, … you didn’t really lose anything.” These relationships not only kept his spirits up but also expanded his view of what was possible.
Landing the Perfect Role: Aligning Passion, Skill, and Purpose
When the “Regional Storyteller” role at Special Olympics New York opened, it felt tailor-made: journalism, sports, and special needs all intersected in a position that valued his experience and authenticity. His age, once perceived as a disadvantage, became an asset for connecting with coaches and parents. He learned video editing and social media storytelling and continues to expand his skills, supported by an organization embracing his perspective.
Impacting Lives—Sharing Mary’s Story and Beyond
“Life with Mary” has become more than a writing exercise—it’s a resource for families raising children with autism, a way to share honest lived experience, and a means to give a voice to the often unheard. Feedback from families and even strangers has affirmed the importance of telling these stories, both for the autism community and for those seeking understanding and inclusion.
Advice for Others: Keep Asking, Keep Learning
For job seekers, especially older adults, Randy Robertson urges a blend of resourcefulness and openness:
- Network widely: Reach out to old and new contacts; be persistent and unafraid to connect.
- Use technology sensibly: Job boards and LinkedIn are useful, but moderate your time. Focus on learning the skills today’s employers want.
- Stay curious: Pursue courses, workshops, or skill-building—often, local libraries or community organizations offer free access.
- Listen and stay open: Transitions may lead to rediscovering joys set aside years ago.
- Remember your value: Age brings experience that can be a unique asset—many organizations value the wisdom and empathy that come with it.
In Randy Robertson’s words, “you just got to get started, get your foot in the door somewhere … and see where it takes you.”
For anyone facing unexpected change, loss, or reinvention, this journey is a powerful reminder: resilience, curiosity, and honesty—combined with a willingness to leverage your network and learn—can transform challenge into fulfillment and renewed impact.
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
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 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.
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