I took some time to think about my own startup journey this week, and one of the things I realized was my lack of courage at certain key points. For example, I should have taken the hard choice of firing a colleague earlier, but instead I dragged the relationship longer than it should. I should have pitched more frequently at certain events, but instead took the passive reaction of sitting back. I should have led our company, instead of letting it run itself.
I now believe that courage is like a muscle - it can be worked on and improved. The key is to putting oneself in tough situations where one has to make courageous decisions, and learning from those scenarios.
Two years ago, three friends and I drove an ambulance from London to Ulan Bator for over four weeks. We had to make critical decisions like when to sit tight and when to keep driving, how to deal with stressful situations, and how to respond when we got pulled over by the police for "speeding". This year, my friend and I trained and ran a triathlon that we were totally unprepared for and had to exercise the courage to keep going.
I look for opportunities to exercise courage, and I look for the same characteristic in people around me.