Chris, thank you for this well written piece. Practically action for action, I could have written it, including the Krav Maga, WHM, GTD, warts and all.
For years I was frustrated about being a generalist, you know, jack of all trades, master of none? Compared to one of my friends who's an eye surgeon, capable of operating on someone using a microscope, I'm a total dud.
Until I came across the label of Multipotentialite, i.e. somebody with (high) potential in multiple areas. I am proud to be a multipotential person, able to change a diaper as easily as a car tire, use an AED or start a fire...
Now, if I get obsessed with archery (my recent new new thing) I don't kick myself if after 4, 6 or 8 months I switch to something else. I enjoyed it, I move on, and can come back from time to time to enjoy it again, not as a beginner anymore, but as a top 70-80% practitioner.
Long story short, I commend and appaud you for trying, for constantly learning, for keeping what works and moving on from that which doesn't, because each experience improves you in some way or another.
You can google a piece by Robert Heinlein which I particularly enjoyed and which applies to my surgeon friend: "Specialization is for insects".
Keep searching, learning and trying!