Where I Stand
- Tobi spent 20 years going deep on ONE domain: internet commerce. I'm across FeatureOS, SupportWire, blog, vault, skills, analytics dashboards, and knowledge management. That's not depth — that's surface area.
- Tobi still codes. He starts new stores, builds apps, makes a new Rails app with every version. This isn't nostalgia — it's how he maintains empathy for what building at Shopify feels like. When was the last time I built something inside FeatureOS as a customer, not as the CEO?
- "Fall in love with problems, not solutions." I'm in love with building tools. The vault, the AI skills, the summarizer. These are solutions looking for problems. The problem I should be obsessed with is: why do customers churn from FeatureOS?
- Tobi says internal tools shape culture more than any memo. I'm building elaborate internal tools for myself. But am I building internal tools that make my team faster and more aligned?
- "Play the table, not the ball." I'm reacting to whatever's in front of me — a new video to summarize, a design to polish, a blog post to write. None of these are positioning me for the next shot. Distribution is the ball I keep ignoring.
- Tobi argues taste scales but barely. He's kept Shopify's taste intact at massive scale. My taste hasn't been tested at scale because I haven't reached scale. Taste without distribution is a private hobby.
- Domain modeling is the job, per Vanessa Lee. Have I modeled the feedback domain deeply enough that FeatureOS's primitives last years? Or am I shipping features without a durable model underneath?
What I Need to Change
- Pick ONE domain and go absurdly deep for the next 12 months. If it's product feedback, then SupportWire serves that domain — not as a separate product, but as an extension of understanding how customers communicate needs.
- Spend one day this week using FeatureOS as a new customer. Sign up fresh. Feel every rough edge. Document every moment of confusion. This is Tobi's "empathy through building."
- Stop building tools for myself and start building tools for the team. What does my team need to move faster this week? Build that instead of another vault skill.
- Apply domain modeling discipline to FeatureOS. Can I describe the feedback domain in primitives and relationships that would survive 3 years of product evolution?
The Hard Question
Is your obsession with craft serving your customers at scale, or is it a sophisticated way of admiring your own work?