👀 Seeing Things Twice

On rewatching what matters — and leading with fresh eyes.

Lately, I’ve been learning from my daughter Olivia.

She just returned from a school trip to Williamsburg, Virginia — full of stories and reflections. On the flight back, she rewatched Life of Pi and texted me her thoughts. Not surface-level takes, either. She dove into the many layers of that film and challenged me to revisit it with fresh eyes.

And that’s been sitting with me.

How many things in our lives — in our work — do we think we’ve already seen or figured out, when in fact we’ve only experienced the first layer? How often do we default to familiar interpretations instead of peeling back the next one?

Talking with Olivia reminded me of what it means to stay curious — and how that same mindset is quietly reshaping the way people around me are showing up.

More and more, I’m hearing from friends who want to experiment — not just with AI or tech stacks, but with how they work, lead, build, and relate to each other. People who might not call themselves “innovators” but are definitely living like them.

Sometimes, adaptation starts with watching a familiar story again and seeing something different.

☀️ Happy Monday!

⚡ Quick Hits

  • Tool I’m Exploring: CodeSandbox.io – a brilliant sandbox for testing code, ideas, or concepts with real-time collaboration. Worth a try if you’re building in public or mentoring others.

  • Conversation Spark: “What’s something you thought you understood, but recently saw in a completely different light?” (I’ve been asking this in a few 1:1s — the answers have been surprising.)

  • Signal I’m Tracking: The quiet rise of “solopreneur CTOs” — individuals spinning up multiple agents, apps, and products using AI-native tools, without waiting for permission.

🧰 Workflow of the Week

Tactile AI experiments > Abstract strategy decks.

We’ve been testing a framework internally: prototype first, explain later. Instead of spending time convincing a stakeholder or executive, we just build a small working version — even if it’s rough — and use that as the conversation starter. It’s lowering resistance, shortening cycles, and creating more “aha” moments.

If you’re leading change in your organization, this might be your edge.

🧠 Prompt

“What’s something I’m pretending to understand — that I’m actually still figuring out?”

This prompt has helped me reframe a few stuck projects and sparked some good hallway conversations this week. Try it with your team. Try it with yourself.

🛰️ The Takeaway

We don’t need all the answers — but we do need better questions. And sometimes, we need to let a kid remind us how to see the magic in a story we thought we already knew.

Thanks for reading. Keep looking forward.

— Alejandro

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