For the past month, I've written my thoughts into a daily journal. I then send that to a group that read it every day and respond. Had 15 a month ago but some were toxic. I'm now down to 5 people. I understand they don't understand possibly even most of what I write, but knowing they'll read it motivates me to express my thoughts--whatever they are at the time.
But yes to your point about the co-founder, they'll understand everything you're talking about.
Why is very popular in the design community, like the five whys [0]. But now I'm always at odds when I speak about it after listening to Richard Dawkins and other scientists say "why is a stupid question." They advise to ask, "what led to this?" And doing that has helped me reframe situations and make discoveries.
Even still, why is a great shorthand in many contexts. :)
