Why “what if” thinking is both my best design tool and my worst habit

Last week I sent a pitch email and immediately started imagining the recipient reading it, cringing, and forwarding it to a colleague with a “look at this” note.

Nobody responded. Not because they hated it. Probably because they were busy. But I had already lived through the rejection, the embarrassment, and somehow the part where it became a cautionary tale.

Here is what I have been slowly realizing: most of my unhappy moments are not caused by things that actually happened. A proposal gets rejected, yes, that stings. But the hours of misery before the rejection? The spiral after sending a pitch? The quiet dread before a student reviews my portfolio feedback?

That is all imagination. Specifically, it is “what if” imagination, and once it starts, it compounds.

What if the proposal reader questions my past experience? What if my students think the advice was generic? What if the silence from that email means exactly what I fear it means? Each “what if” builds on the last until I am treating a fictional outcome as fact.

I came across the idea of first principles thinking recently, which is essentially the practice of stripping a problem down to what is actually, verifiably true and building from there.

It is almost the exact opposite of what I naturally do. I start with a fact (I sent an email) and immediately start constructing a story around it using the least generous interpretation available.

First principles would ask: what do I actually know right now? The answer is usually: almost nothing yet.

The uncomfortable part of this realization is that it removes a certain kind of comfort. When I am unhappy because of a “what if,” there is nothing concrete to fix or respond to. The problem is the thinking itself, which is harder to address than a real outcome.

I do not have a clean solution to this yet. But I have started noticing how often I walk into a bad mood that I personally constructed, with no outside help at all.

Turns out I am a more prolific creator than I thought. Just not always making things I intended to.