CHAPTER 35

Stop Should-ing on Yourself

In a session a while back, my counselor Eleanor said to me, “Mike, it sounds like you’re should-ing all over yourself.” I laughed when she said this, as I’ve heard this expression many times before—I’ve even given this same feedback to others. However, something about her saying this to me at that particular moment caught my attention.

As I started to take inventory of the most important aspects of my life, I was a bit shocked to realize that much of my motivation in these areas comes from the perspective of what I think I should do, say, or feel, and not from a place of what’s authentic and true for me.

Most specifically, I find myself challenged by various competing “shoulds” in my head in regard to my business and my family. Both require quite a bit of energy, which is true for most of us. Because I run my own business, I have to make a lot of choices about where to focus my time and energy—writing, traveling to speak, staying home with my family, and so on. The choices I make have a big impact on my family not only because I’m the primary breadwinner but also because they determine how much I’ll be around to help with day-to-day life. I try to be as mindful as I can about these choices, although it isn’t always easy. If I’m not conscious about it, that voice in my head can easily pop up and say “You should be spending more time with your family” when I’m on the road speaking or up early (or late) working on a project. At other times, that voice can start talking when I’m on vacation with my family, at an event at the girls’ school, or even playing a game with one of them: “What are you doing? You should be working right now, so you can send these girls to college and make more money for your family.”

Our obsession with doing, saying, or feeling the way we think we should is actually less about genuine desire or commitment, and more about a lack of self-trust. When we operate from that place of should, it’s often because we’re feeling scared, flawed, or simply not confident in our own thoughts and beliefs. This insecurity leads us to look outside of ourselves for guidance, and this often causes us even more stress.

What if instead of asking ourselves “What should I do?” we asked different, more empowering questions like, “What’s true for me?” or “What am I committed to?” or “What do I really want?” These questions, and others like them, come from a much deeper place of authenticity.

This is not to say that everything we think we should do is inherently bad. That is clearly not the case. Some things we think we should do—like eat better, communicate with kindness, exercise, try new things, organize our lives, take care of ourselves, and so much more—can be important aspects of our success and well-being (as well as that of those around us).

However, when we come from a place of should, our motivation and underlying intention for doing something is compromised—even if it’s something we consider to be positive or healthy. In other words, we often feel stressed, bitter, resentful, or annoyed when we’re motivated by should. This “should” mentality is based on an erroneous notion that there is some big book of rules we must follow in order to be happy and successful. There are times, unfortunately, when I’m doing something “fun” like riding bikes with my girls, watching a movie with Michelle, or going to a ball game with some buddies, but my obsession with what else I “should” be doing takes me away from fully enjoying and appreciating the experience in the moment.

The distinction here is one of obligation versus choice; “have to” versus “want to.” When we stop should-ing on ourselves, we’re less motivated by fear and can choose to be inspired by authentic desire.

Sometimes we may also find ourselves looking to others to tell us what we “should” do. While there’s nothing wrong with our seeking guidance, our deepest truths come from within. When we let go of our insatiable desire to figure out what we “should” do, we give ourselves permission to listen to our inner wisdom, trust ourselves, and make whatever changes we deem to be important. And, if there are actions we want to take that we believe will enhance our experience of life, we can take them from a place of self-trust. There are so many new and exciting possibilities we can create once we let go of “should.”