Whenever people take a big decision, one of the questions everyone tends to ask themselves is what the worst is that could happen. The idea is that you put a boundary on the worst possible outcome so that you have an idea of what the worst case downside risk is. One lesson from the VC community is that you can only lose your money once. That may seem obvious, but bear with me. When investing, say, 100K€ into an early stage startup, your worst case downside risk is those 100K. However, you should look at the upside of the deal as well. Assuming the startup does well, you may get your money back 10x, 100x or even a 1000x. The worst case is a -1x whereas the upside is, in principle, infinite. Of course, I am human too and every time I fork over money to a startup, I mentally say goodbye to those funds. But I have learned to also look at the upside and ask myself the question what the best is that could happen. That’s not just wishful thinking as I have had nice and successful exits. So, next time when faced with a big decision, ask yourself what is the best that could happen!