Flexibility vs Randomness

Ah, ADHD my old friend

A challenge of any creative endeavor is striking a balance between being stubborn to your vision and being flexible about learning. Neither extreme works well - especially in entrepreneurship when it’s critical to respond to the market but also critical to not be so responsive that you lose your insight and become undifferentiated. This is true for most creative fields too.

I have ADD (ADHD but without the hyperactive part - I can sit still for the most part but my brain hops around a lot). It’s a real gift when it comes to being creative and doing lateral thinking, but it can also lead to some real randomness. It’s hard to know the difference sometimes - good ideas are usually an initially unintuitive hop from what you’re doing at the moment, or a connection that seems unlikely but that pays out. Or sometimes, when you are stuck on something, coming at it from a different perspective helps. But sometimes it’s just procrastination.

It’s hard to grapple with this problem. Again, neither extreme is really optimal - the right mix is somewhere in the hard middle. So, you have to attack it less with a formal rule and more with heuristics, like “do the important and urgent stuff first, then important and not urgent” etc.

Sometimes I find that timeboxing or budgeting helps. Like, I get to say or do three random things per day, or per meeting, and I try to keep myself in that box if I can. Another thing is to try to stop and ask, “can I plausibly point at how this advances me towards the current goal?” If not, then at least give a limit to the amount of time spent in that state - it’s ok to do something that “feels right” for a while even if you can’t explain why, but too much of that begins to tip over into randomness.

One other strategy I use to manage this, related to budgeting, is “parking lot”: I’ll let myself have random ideas but simply record them somewhere without doing much, and come back to evaluate the list when I have time. Often, I find that time makes things clearer, in both directions. This lets me have all of the creative ideas I want without being disruptive. This works well in meetings - I take notes and often just don’t say what is in them because they become less relevant by the end.

As with many things in our professional lives, there is a balance here. In a moment like this with AI, where there are lots of new tools and techniques to use, it’s easy to become lost either by being so rigid in our workflows that we miss out on something new and powerful, or being so enamored of chasing all the new ideas that we never get anything done. Striking this balance is hard, but critical.