Backsliding - Why We Fail
It’s been a long time since the last episode. This one exists because I needed it more than you did. Last fall I was living 43 floors above Austin, taking $20,000, $30,000, even $43,000 days — a couple hundred thousand a month — and telling myself I was being careful. Then I shorted a stock, it hit my stop, and instead of closing it I added 10,000 shares. An hour and a half later a million dollars was gone. The strange part: it didn’t hurt as much as the $5,000 I lost on non-farm payrolls in 2006, because that $5,000 was everything I had. This episode is a reading of, and an argument with, Meghan O’Gieblyn’s Harper’s essay “Backsliding: On the paradox of willpower.” The line that holds it together is Simone Weil’s: we have to try to cure our faults by attention and not by will. Willpower is how you get the terrible fall. Attention is how you notice the state you’re actually in before you add size. Trading is easy. You wait, you take it, you stop it if it’s not good, you let it run if it is. Those things are impossible in the wrong state of mind. The work is not another mantra about protecting the account. The work is quieting the voice, paying attention to one small thing — bird watching, serving someone, a word you repeat until you mean it — until, in the moment that matters, you don’t have to command yourself. You just obey. I made this for me. I’m the worst example in it. Essay: Backsliding, Meghan O’Gieblyn, Harper’s, July 2026 (https://harpers.org/archive/2026/07/backsliding-meghan-ogieblyn-willpower/) Harper’s gives two free articles a month. I’ll also put the link at robbooker.com. Also mentioned: Paul Tudor Jones on Invest Like the Best; Roger Lowenstein, When Genius Failed; Michael Singer, The Untethered Soul; Simone Weil, Gravity and Grace; Iris Murdoch; William James; Romans 7; Philippians 4:8.
