o3 l drafts a future, then waits for your redlines. Prompting is secondary; the real skill is slashing, annotating, and rewriting the version of you the AI proposes until the roadmap sounds like a life you’d want to live.
Then it slid over a single Mad Lib: If vibe coding vanished tomorrow, I’d still spend my time ______ because it lets me ______. I filled in the blanks (”writing” and “understand what I think and connect with people authentically” were my answers) and hit enter. o3 redrew the flight plan yet again. Then it gave me an action item: Block off two hours each month for “agenda‑free writing.”
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o3 is ambitious, but it’s not magic. It drafts the future, but I still have to live it. Here’s how I’m operationalizing the roadmap we built together:
Log the receipts. o3 made me a metrics tracker. I keep a simple spreadsheet where I collect post views, engagement stats, and content outputs. I have a recurring reminder to update it weekly to keep me honest about where I’m winning and where I still need work.
Even with full visibility into a knowledge graph, a user still needs to plan with an agent. Tags alone could scaffold that process — suggesting structure, surfacing connections, and providing transparent prompts to revisit and check progress over time.
Six months ago, I asked whether a language model could sketch my future. Then I closed the tab and got back to work. By Dan Shipper’s reach test, where you measure the success of an AI tool by how often you instinctively reach for a tool, that first-generation career coach flunked.
Try this at home: Build your own AI career coach Somewhere during our first career chat, o3 offered up a tantalizing possibility: It could build a prompt version of itself for me to copy and paste into the custom instructions of a project, so our strategy sessions could span conversations. I had it do that—and so can you.
Chat-based AI coaching is useful in the moment but not habit-forming. Chat is not discoverable — the real question is how the breadcrumbs and receipts a tool provides shape ongoing interaction and behavior change.-
Prompts that work well
- “What’s a sustainable version of ambition for me right now?”
- “Can you help me build a roadmap based on what I’ve already done and loved?”
- “What’s a small experiment I can run to test this path without overcommitting?”
“What am I undervaluing in my current skill set?”
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