"Constraints" is when I finally understood why, when trying to get a startup off the ground, it wasn't going to work.
The first (and only) time I tried to make a plan with my co-founder, and there was an obvious constraint, he couldn't work with the constraint. It was at that point that I realized my co-founder just couldn't stop himself from letting his imagination run away.
For context, throughout the process of trying to get our startup off the ground, every other week or so, my co-founder would come to me with some kind of idea and just wouldn't take "no" for an answer. I couldn't understand why he just kept pushing beyond reason, until he got into that mode when we had an external constraint around what the idea could be, and he couldn't adapt his ideas to the fundamental constraint that we had to work with.
At that point I realized that my co-founder was just letting his imagination run away the entire time: constraints be damned! It became clear that my co-founder couldn't turn his insights into actionable plans.
> The first (and only) time I tried to make a plan with my co-founder, and there was an obvious constraint, he couldn't work with the constraint.
The tandem word here is "discipline". Once the constraint is created, then discipline is required to stay within that constraint.
Case in point: deadlines. Deadlines are fine. Deadlines without discipline with respect to scope creep is just setting a team up for failure and low quality work.
It wasn't even a "team." It was just two of us. We simply didn't get far enough, in part because I insisted that we bootstrap until we had a product.