Old Dog, New Tech: Learning AI at 57

Jumping Back Into Learning

After graduating college in the 19XXs, I was ready to learn from life—not another classroom. For decades, my education came from people, teams, and experiences in resort operations.

Then an unexpected career change (also known as job loss) left me wondering what was next. Instead of rushing into another role, I enrolled in an eight-month postgraduate certificate program in Artificial Intelligence and Machine Learning.

It may have been part stall tactic, part self-therapy—but it turned out to be exactly what I needed to wake up new parts of my brain and reframe the next chapter of my career.

When I told friends and family what I was doing, I joked that I wanted to create new brain synapses. Turns out, that wasn’t far from the truth.

Immersion in a New World

The program required 10–12 hours a week of study, and our instructors warned us it would be rigorous. One graduate even admitted he’d taken a leave of absence from work just to finish.

That should’ve been my first clue.

Within days, I was neck-deep in new vocabulary, new software, and new ways of thinking. The pre-course work alone felt like learning a new language—complete with late-night study sessions and dreams in Python code.

It was humbling, frustrating, and fascinating all at once. I wasn’t just learning new material; I was retraining my mind to learn differently.

The Click Moment

About three months in, something shifted.
Concepts started to make sense. I was no longer drowning—I was swimming (though maybe not elegantly).

The coursework became collaborative, and I learned to ask for help, a skill I’d long advised others to use but rarely practiced myself. It was a reminder that growth always comes with humility.

Lessons in Adaptability

Balancing part-time consulting work with demanding coursework brought new challenges—like discovering that repetitive typing can, in fact, cause physical injury. But those small struggles underscored a bigger truth: learning something new requires whole-body effort.

By the time August rolled around, my classmates and I celebrated completing the program. We were scattered across the country, but our shared sense of pride connected us. We had done something difficult, meaningful, and affirming—proving that curiosity doesn’t have an age limit.

Key Takeaways

• Learning rewires your mindset—not just your skills.

• Mastery isn’t the goal. Growth happens through the process.

• Curiosity opens doors to new people, perspectives, and possibilities.

• Challenging yourself builds resilience and adaptability.

• You’re never too old to learn. Ever.

About the Author

Peggy Hiller serves as a catalyst for intelligent organizational transformation—helping leaders align people, purpose, and AI to create more meaningful, efficient, and human-centered organizations.

Peggy has spent more than 25 years leading operations within the ski and hospitality industry, including serving as Vice President of Operations at Arapahoe Basin and CEO of a national ski association.
She now partners with business leaders to make Artificial Intelligence and Machine Learning accessible and practical—helping organizations develop strategies that align technology with people and purpose.
Known for her collaborative, authentic approach and ability to connect big-picture strategy with real-world operations, Peggy brings empathy and humor to complex change.
She believes the first step to any AI journey is simply starting the conversation. She’d love to work with you to discover your unique AI strategy.