Why keeping our options open is making us fail

Growing up I’ve always heard adults talking about the importance of keeping their options open. In college I heard my friends trying to go into consulting and law school precisely because it will help them keep their options open. Being a jack of all trades was respected and the ideal of being well-rounded idolized.

I had become so exposed to this notion that optionality is a positive thing that it became second nature to me. I applied to consulting jobs and even when I decided to go down the tech path I tried to optimize my next career move based on optionality. However, I’ve recently come the conclusion that I was wrong.

But why? Why shouldn’t we keep our options open? I believe that the only way to become truly excellent at something is to only focus on that one thing. That means forgoing all of those other opportunities that we might have. Making these trade-offs can be really hard. However, once I internalized the fact that excellence is all about focus it became really easy to discard any opportunity that I believe was being a distraction.

See the problem of optimizing for optionality boils down to people’s fear of making trade-offs. For so long I wanted to keep my doors open because I didn’t want to make a decision that I would regret. Why decide to commit to something that I wasn’t sure of when I could just defer that decision a couple of years into the future? The reality is that in many cases there’s no strong incentive for people to make decisions now vs in the future. In most cases, the opposite is true. For example, many people that want to start companies defer making that decision in favor of gaining experience at a company. The problem is that deciding to stay at a company is typically rewarded with job safety, promotions, and in many cases social capital. Meanwhile, starting a company is always rewarded with risk.

Having said this, I will say that exploring your options is always important. I wouldn’t have the capacity to drop everything and focus on one thing if I was not sure that I had explore my options. However, there’s a difference between proactively exploring your options and reactively avoiding making a decision. Understanding this distinction has helped me focus on what matters to me and forgo every other option.