The most dangerous word I know

On the day of my fourth anniversary at Microsoft, I had a realization that my job no longer felt like a good fit. I was very successful, but I was realizing that engineering wasn’t what I was cut out for, nor was it what I was passionate about. The obvious question I started to ask myself was, if not this, what else should I be doing?

That started me down a three year road of asking myself if I should leave Microsoft, if I should pursue several opportunities that came up along the way, and what I should do post-Microsoft. I felt like I no longer wanted to be there, but had no idea what else I should do instead. It wasn’t until I left my job and gained some perspective, that I realized a large part of my feeling stuck was directly tied to the way I was asking the questions.

Specifically, I’ve come to realize just how damaging it was to use the word “should.” It’s such a small word yet it completely transforms how we make decisions and how we view the world and our place in it.

“Should” hides two subtle but important fallacies

1. Fallacy — There is one right answer to your question

When we ask what we should be doing, or what we should do next, implicit in the question is the assumption that there is a single correct answer that we just need to find. We treat our life’s direction like a test question where the answer will be judged against some rubric of our ideal life, and we will have either chosen correctly or incorrectly. This thinking raises the stakes for our decision beyond what it needs to be. With this mindset you’re not only responsible for finding an answer, but you’re responsible for finding the only correct answer.

The reality is that there are likely many directions you could move in, and no one direction is inherently better. What needs to guide you in your decision making process is your understanding of yourself, which once clarified will help you sift through options and pick likely candidates. Your next move doesn’t need to be an absolute perfect decision, but rather a degree of improvement over where you currently are. This frees you from the pressure of feeling like you must choose correctly, and instead lets you just worry about choosing well.

2. Fallacy — The answer to your question exists outside of yourself

Every time you ask what you should be doing, you are declaring that the answers are to be found in some external oracle that you just need to find. You believe that if you could find that external source, maybe the voice of God, maybe some successful person that would just tell you what to do, or maybe a fairy-tale event where you get “discovered” and pulled into an amazing life, everything would be fine.

The reality is that you are wired a certain way to interact with the world, and nothing outside of you can dictate that to you. Nobody can tell you what your favorite flavor of ice cream should be (although advertising certainly tries), you know what it is simply because of the way your tongue is wired for taste. For this same reason you shouldn’t search externally for someone to tell you what your favorite activities will be, and what will make you come alive. That is all something that must come from within. You can seek help in uncovering what those are, which is what life coaching is all about, but the answers will all come from inside of you.

What is external might be a framework that you are choosing to live within. This could be your country’s or state’s laws, and it also might be religious laws. These define boundaries for you and are guide rails to help you interpret what is appropriate behavior and what is inappropriate or illegal behavior. What they don’t do is define for you how you should live within those boundaries. The government doesn’t tell you what job you should have, nor do most religious texts for that matter. That is something that must come from inside of you.

The answer is to change the question.

Instead of asking “what should I do?” ask yourself “what do I want to do?” This doesn’t make it an easier question, but it makes it a much better one, and one that you can actually answer. When you change the question, you give yourself permission to pursue what makes you happy and what makes you come alive. You will orient your energy and focus inward, towards self-discovery, which will yield insight and progress. Ultimately, it is the only path that will lead you from being stuck to being fulfilled.