It’s no secret that I enjoy using AI.
I’m naturally curious, and whenever I become interested in something, I tend to obsess over it for the long term. I like frameworks, systems, and ways of thinking. Whether it’s product strategy, philosophy, or boxing, I enjoy going deep rather than wide.
Because of that, ChatGPT has become much more than a search engine for me. I don’t just use it to find information. I use it to challenge my thinking, refine my frameworks, expose weaknesses in my reasoning, and explore different perspectives. It’s become part of how I think through problems.
Recently, I noticed that this behavior expanded into something else.
It became part of how I made a purchase.
The Problem
For several months, I knew I needed new boxing shoes.
The basketball shoes I’d been training in for years were completely worn out. The soles were breaking apart, and I had started feeling pain in the ball of my foot.
Since I take boxing seriously and plan to compete, buying new shoes wasn’t an impulse purchase. It was an investment in something I care deeply about.
Naturally, I assumed the answer was simple.
Buy boxing shoes.
So I started researching.
I looked at reviews, watched videos, compared brands, and discussed different models with ChatGPT. Adidas, Nike, Asics, Everlast, Hayabusa—they all seemed like good options. My boxing coach, a former Canadian Olympian, even gave me his own recommendations.
On paper, every option sounded good.
When Research Meets Reality
Eventually, I found a boxing store that carried several different models.
I tried on six different pairs.
To my surprise, none of them felt right.
They all felt much less comfortable than I expected. There was very little cushioning, I didn’t feel as light on my feet as I anticipated, and the narrow sole didn’t match the way I naturally moved while boxing.
I left without buying anything.
The following week, I tried on basketball shoes instead.
Then more basketball shoes.
Altogether, I probably tried close to twenty different pairs of athletic shoes over the course of several weeks.
I still couldn’t make a decision.
Not because I lacked information.
Because I wasn’t convinced.
The Conversation
This is where I noticed something interesting about my own behavior.
Throughout this entire process, I kept returning to ChatGPT.
Not to ask the exact same question repeatedly, but because my own decision criteria kept evolving.
We talked about what actually defines a boxing shoe.
Whether cushioning mattered.
Why some professionals preferred one style over another.
Whether basketball shoes could actually be the better option for my particular movement style.
Each conversation refined my thinking.
The AI wasn’t making the decision for me.
It was helping me clarify the framework I was using to make the decision myself.
Eventually, after nearly a month of conversations, I bought another pair of basketball shoes.
Ironically, they cost more than I originally planned to spend.
The moment I put them on, I knew they were the right choice.
I haven’t regretted the purchase.
What I Learned
Looking back, three things stood out.
1. AI had already become part of my everyday behavior.
By the time I started shopping for shoes, I had already spent months using ChatGPT to discuss boxing strategy, coaches, different fighters, southpaw versus orthodox styles, training philosophy, and my own development.
Using AI to help with a purchase wasn’t a new behavior.
It was simply an extension of an existing one.
2. The purchase wasn’t isolated.
Buying shoes wasn’t a standalone shopping event.
It emerged naturally from an ongoing conversation I was already having about boxing.
My interest in boxing came first.
The purchase followed.
That feels fundamentally different from opening Google and typing “best boxing shoes.”
3. The decision was conversational.
Perhaps the biggest change was how the decision evolved.
Instead of searching once and choosing from a list, I refined my thinking over time.
Every conversation helped me clarify what I actually valued.
The AI wasn’t replacing my judgment.
It was helping me develop it.
Why This Matters
This experience changed the way I think about product discovery.
My purchase wasn’t driven by a single search.
It emerged from weeks of ongoing conversations about a subject I genuinely cared about.
As people spend more time interacting with AI around their long-term interests, I suspect more purchase decisions will happen this way.
The recommendation isn’t the beginning of the journey.
It’s often the continuation of a much longer conversation.
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