How Do You Know You Are Taking Enough Risk?

Nick Kokonas knows he is taking enough risk when a morning feels close to throwing up and he has not thrown up yet. He is motivated by fear of not living up to the possibilities. Waking up feeling great means the risk is too low. Waking up throwing up means the risk is too high. The aim is a tingle of uncomfortableness, and the original word for the feeling is nausea. The line stayed as a check on whether he was still learning and still pushing the edge of what the possibilities are.

Keith Goggin, a good friend and former business partner, gave him the line while they traded in the 90s and early aughts. They held a ridiculous short position on Plug Power, and the company still exists. Kokonas was really on the verge of throwing up every morning and had not thrown up yet, so the risk sat where they needed it. He internalized the test at the time. When comfort arrived later, the calm meant they were not taking enough risk, not learning, and not pushing the edge of what the possibilities are.

A morning that feels great is too safe. A morning that starts with throwing up is too much. The useful morning stays uneasy and still stops short of getting sick.