Every now and then, I take a step back and reflect on my career. And its milestones.
They usually show up during deep shifts — when something so big hits the industry, you can’t ignore it. The kind that makes you feel like a beginner again. Like you’re about to get replaced… or maybe reborn.
AI is one of those moments.
I didn’t welcome it with open arms.
At first, it felt off like yet another overhyped trendy product. Then came fear. But slowly, like the first time I held an iPhone in 2007, I started to lean in.
While I miss spending eight days straight crafting a single app screen in Photoshop, I’m not chasing the past or being too anchored to it.
I’m just recalibrating. Trying to stay sharp and focused.
When the iPhone came out, I had a visceral reaction.
I previously wrote:
The OG iPhone had just launched. Rushed to the 5th Avenue Apple Store on Day 1 to get one. The App Store didn’t exist yet. I couldn’t afford one and was struggling to pay rent, but I was obsessed. Obsessed with what it m…
Keep reading with a 7-day free trial
Subscribe to The Playbook to keep reading this post and get 7 days of free access to the full post archives.