No More Cookies

I signed up for a course to learn how I might use AI to improve my work. Rather than me get to understand AI, the premise of the course is “get AI to know you” so it can calibrate its interactions with you to produce the outputs that will serve you best.

Its framework is a series of questions, similar to a personality profile, from which it makes informed predictions about what motivates you, what scares you, your obvious strengths and the weaknesses you thought you’d hidden. For someone who loves self-reflection, this is intoxicating. It provides a conversation partner who is _endlessly_ fascinated with your favourite topic and is biased towards being complimentary, following up anything I tell it with “yes, yes…tell me more.”

It’s not without genuine merits. The circular interview style tunes the AI’s model of me ever more accurately. And because it can generate its own follow up questions, this becomes a quiz that only I could take.

Once I’ve answered everything — questions about my working style, goals, how I deal with conflict, praise, criticism — it begins generating long detailed reports. Reports from different perspectives on all sorts of topics that could fine tune my life.

The first report reflected something I’d told the AI for myself: I want to write more, and I want to get better at writing that will be interesting and helpful to other people.

After six reports—each one a perfectly tuned mirror reflecting my working patterns and aspirations—I hit generate on the seventh. The AI paused.

“I can generate this report and many more after that. But the 10,000 words I produce won’t be yours. You told me you want to write for others. Use this time to write something of your own.”

In one sense, my efforts had succeeded. AI knew me well enough to deliver not what I’d asked for, but what I actually needed. It’s as though I asked for one more cookie, and AI handed me an apple saying “go write your damn post”.

At the same time, the exercise might be a failure. Self-optimisation is a seductive trap. Lose weight, gain muscle, slow down, be more efficient. Any advice is worthless until put into action and anything learned about myself is useful to only one person until I open myself up to the vulnerability of sharing it.

It’s human tendency to choose comfortable self-reflection over vulnerable creation. It can be terrifying to put your thoughts out into the world with your name on them. I’m 400 words into this post and still debating whether to post without a smart tool or framework to share.

But maybe we don’t need another tool. Maybe the point is that making and sharing something imperfect can connect much more powerfully than sharing nothing at all.

PS. Myers Briggs ENFJ-A, Enneagram 2w3 → 7, Kolbe FF 6-7…