How to Know When a Risk Is Worth Taking

When my kids were little, there would be an occassional tantrum. I always chose my battles carefully because not every hill was worth dying on. In fact, I would use that language with them, “…this is a hill I’m going to die on, and these gloves are going on your hands because it’s freezing outside”, or “…it’s okay for you to continue to cry about putting these shoes on, but this isn’t a hill I’m going to die on”. In these situations, they knew they could continue to cry but I was going to “win”, or they could continue to cry but it was a waste of energy because I didn’t truly care what they decided. Either way, it took the steam out because they knew clearly where I stood. And I only chose hills that were worth it, like the ones where they were going to get frostbite and their fingers were going to fall off.

Building your capacity to be “competently couragous” requires a lot of discernment. What hills are worth dying on, and which ones aren’t?

🧤 Are your deeply held values or other ethcial standards being violated?
🧤 Is the timing right?
🧤 Are there allies who can/will support you?
🧤 How does acting now fit into your (or your organization’s) broader objectives?
🧤 Have you accumulated enough social capital to take the risk?
🧤 What are you willing to lose/not lose?

When you raise a fuss or hammer every single issue, your voice gets diminished. The wagons circle with you on the outside. Being courageous requires taking risks, but it doesn’t mean you should take on every issue. Use your voice, but use it well. Develop discernment, and when the stakes are high, approach risk strategically.