If you ever want to read a short, enjoyable biography of an actual hobo, I recommend "You Can't Win" by Jack Black (no, not that Jack Black): You Can't Win https://www.amazon.com/dp/1902593022/ref=cm_sw_r_cp_tai_RMjLEb9QPVJHY It's a wonderfully interesting read, and I'm close to placing it on my "recommended reading for small business owners" list. Oh, and Wikipedia says it'll be a movie soon-ish.
Portrait of Jack Black by Edward Weston This "you can't win" idea keeps popping up on my perceptual dashboard. Bill Callahan recorded a wonderful cover of a Kath Bloom song, "The Breeze/My Baby Cries". There's this passage from the song: "Yesterday I talked with my father He said that we could never win It's so hard to tell Where I end And my father begins So if you see me passing by Please hold me deep in your heart"
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What constitutes winning? I think there are multiple valid answers, and a variety of contexts in which winning might look different. For me, in the main, winning is maintaining a healthy average velocity. IIRC, I picked up this lovely way of phrasing it from Shane Parrish. This defines winning based on inputs that I have more control over rather than outcomes I have less control over. I like that. It's goal-setting 101, but good to remind ourselves about this anyway. What does winning look like for you? -P