This is not an essay about product management.
This is about what it's like to navigate the heights of creativity and the depths of exhaustion, simultaneously. It's about what it means to really learn, by doing.
The AI mandate
This summer, against the backdrop of rapid changes in the product landscape, I dove headfirst into the circus of AI tools. Prototyping. Researching. Designing. You name it, I tried it.
Most of my education was self-led through hands-on projects, podcasts, and YouTube. Some was structured through online courses, much was with my team at work. All of it left me wanting.
The tools and use cases for building with large language models change so rapidly that I inevitably feel unsatisfied, knowing I'll never catch up. And worrying. Because there's this sense that learning AI is imperative for the long-term viability of my career. It's this prescribed framing of what success in my field looks like that really discomforts me.
Don't get me wrong, I love learning. It's the best part of the PM job. Watching the wholesale transformation of how we build, in real-time, is astonishing. Yet the gravity assigned to "upskill in all things AI" feels like it's missing the point.
The possibility of AI makes me feel more creative than ever, yet the industry narrative focuses on speed to market and an upskilling arms race.
So I'd like to propose a different approach: How might we make this more fun?
Choosing a playground
Having spent the last decade of my career at the intersection of technology, real-world logistics, and labor, I'm uniquely interested in AI's role in real-world operations. As a proud geriatric millennial, raising kids far from family, I'm also constantly seeking ways to feel more connected with my community.
I was inspired by Groupon founder Andrew Mason, who recently opened a physical board game social club in Berkeley as a way to experiment with building a brick-and-mortar business around AI tools. Instead of just reading about AI, he built something real where he could actually test it.
So I decided to play in my small mountain town. I started with services I use, identified ones that seemed fun to explore (wine shop, paving company), and offered to solve one or two workflow problems for them, using AI.
In the process, I remembered what I love about this job.
4 reasons why working with small businesses can level up your skills
Rapid iteration cycles
Stakeholder alignment hell doesn't exist in Main Street businesses. Ship something Monday, get feedback Tuesday, iterate Wednesday. This cycle forces you to develop product intuition through fast feedback loops. And it's glorious.
Constraint-based thinking
When working with old-school businesses you learn to solve problems with existing tools before building new ones. Their operations are already complicated enough. Take a local pool and spa company with $14M in revenue and 700 customers on a maintenance route. They had a leaky bucket problem. Literally. Their chemical usage was through the roof because techs were heavy-handed with treatments.
The solution? Skip the fancy inventory software. Instead, we added QR codes and digital scales to their existing workflow, then used an LLM to spot patterns. Transformative results, no data analyst required. This mindset forces creativity in ways a massive budget never will.
End-to-end product ownership
You ARE the research, strategy, execution, and customer success team. You can no longer hide behind specialists; you feel every part of the product lifecycle. You get to own everything, which makes you a better PM, and makes AI less of a luxury and more of a lifeline.
Real user empathy
Solving a problem for someone in your community is immediate and visceral. I can't hide from the local wine shop owner who takes her kid to the same soccer practice as my three-year-old. There are no user personas here, just actual people I'm solving real problems for. You learn fast what actually matters.
What this has to do with AI
As working parents with two kids under three, my husband calls our collective exhaustion "a lifestyle." But here’s the thing: when you have 45 minutes between putting your kids to sleep and your own collapse, you can’t waste time on another course that just scratches an itch. My activities really have to count. This constraint has, in fact, become my greatest competitive advantage.
As I reflect on the past few months of experimenting with AI through local businesses, I've come to remember a common truth: you'll never really learn something unless you get your hands dirty and raise the stakes. No amount of podcasts, classes, or sandbox experiments in our work environments can replace that urgency.
Which brings me to my latest project: I'm building a much-needed night nanny service from the ground up as a way to experiment with AI tools. Yes, I'm solving for myself. But dammit if that isn't the most motivating way to learn.
Your turn
Stop applying for jobs and pick one business you frequent. Watch how they actually work. I bet you'll spot three workflow headaches that you + AI could solve and learn more about practical applications than any course could teach you. Plus, you might just have fun 😉
Want to follow-along as I learn more? You can catch me here.
