Working Overtime

When o3 Plans Your Career Better Than You Do

Watch AI write my five-year roadmap, then grab the step-by-step template to do it yourself

As AI races ahead, we try to step back from the fray every once in a while. Each quarter, we gather for a "think week” to reflect on our work from the previous quarter and come up with new ideas that we can build to keep delivering an incredible experience for our readers. In the meantime, we’re re-republishing five pieces by Katie Parrot with insights on how AI is changing our professional lives. Yesterday we re-upped her piece about how companies' "zero-AI" policies reflect our tendency to equate struggle with value. Today we're running Katie's experiment in using o3 as a career coach.—Kate Lee

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I’ve always hated the question, “Where do you see yourself in five years?” Answering it feels like an exercise in forced self-aggrandizement—vaulting myself to the top of the org chart just to prove I have the right measure of ambition and am not afraid to "think big." If someone could supply an answer that felt authentic rather than pandering to whatever hiring manager asked the question, I’d Venmo them a finder’s fee.

So the Friday after o3 dropped, filled with equal measures of curiosity and dread, I let OpenAI’s newest model take a crack at earning a co-writing credit.

All screenshots courtesy of Katie Parrott/o3.

Six seconds later, I was staring at a scrollable epic, complete with revenue mix, milestones mapped to the quarter, and a five‑bullet case for why this future is “plausible.” In o3’s 2030, I’m editor in chief of Every, running a product studio, and on sabbatical writing a romantasy novel.

This model dreams bigger for me than I do.

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Six months ago, GPT‑4 helped me reorient after a layoff. Since then, my career has evolved—and ChatGPT has leveled up from reactive analyst to agenda‑setting aide‑de‑camp.

Most stories about AI’s rapidly progressing capabilities hinge on fear: Automation eats jobs, algorithms erode agency, everything human gets flattened into paste. o3 presents a subtler puzzle: instead of waiting for prompts, it drafts possibilities. It proposes versions of you that you might actually want to become, and charts a path to get you there.

This essay is my field report on co-authoring a future with a machine unburdened by human baggage around ambition. Come to watch AI turn an argument into an action plan; stay for instructions on how to build an o3 career coach of your own.

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