Jason Leavitt: Learning How to Grind

“I would not give a fig for the simplicity on this side of complexity, but I would give my life for the simplicity on the other side of complexity.” ~ Oliver Wendell Holmes There’s a profound simplicity that can only be reached by working through complexity. It means that deep understanding is often simple, but achieving it requires grappling with and overcoming complexity. Jason Leavitt believes this wholeheartedly. And this was his path. When he first got involved in trading, everything seemed simple: buy low, sell high, make money. But as he dug into it, his research and experience led him down numerous paths — some fruitful, some not so much — and he, like many of us, reached a point near analysis paralysis. Upon reaching this apex of his learning curve, it was then that he began stripping away the extraneous and superfluous to reach the core of what mattered most to his style and skill set. “We need to be able to comfortably execute within our comfort zone,” Jason says. And the work of getting his process down to the most simple of data points and execution triggers was, and continues to be, an essential ingredient for him to find success. And one of the key methods he gets to the core of what works is to use his own trading results and experiences as direct feedback. If or when he stubbornly ignores his own data, this is when trading becomes hard. The lesson is to listen to what your trading stats are telling you. One of those lessons he learned early on was that to go from bad to good and good to elite he needed to push himself to take bigger positions when the markets aligned best with his skillset. He needed to focus on developing the sense of when conditions are right for him to push. Please enjoy this conversation with Jason Leavitt.