I still wrestle with “shoulds.” They’ve just changed over the years. It’s a hard habit to break, and for me, it almost happens in layers. I get by one set of shoulds, and as I go for my next level, I encounter more. Early in my career, my shoulds sounded like this: follow the rules, do what others say, wait your turn, don’t rock the boat. I thought that was the only way forward.
The truth is, those shoulds kept me small. I gave more credit to other people’s voices than my own. I thought someone else had the power to decide when I would be recognized or move ahead. What I didn’t realize is that I had what I needed to step into leadership and make an impact wherever I felt I could.
When I started training in NLP, I learned that “should” is what’s called a modal operator of necessity, which simply means words like should, must, have to, or need to that create a sense of pressure and obligation. These words create weight on our shoulders, closing doors and locking us into the belief that there’s only one way to succeed. But the moment you release a should, it feels like permission. It’s no longer “I should,” it becomes “What could happen if I tried?” That shift opens the door to possibility.
In leadership, shoulds show up everywhere. Leaders tell themselves they should act a certain way, communicate a certain way, or mimic a style that isn’t their own. Women in leadership, for example, often feel they should be more aggressive to be taken seriously. The result? They spend an enormous amount of energy trying to be someone they are not. And that is exhausting.
Readiness is about moving from should to want to or get to. Should closes the door. Readiness opens it.
Shoulds can also show up in how we lead others. Do you catch yourself telling your direct reports what they should do, instead of inviting them to explore options? When we place our shoulds on others, it can feel like pressure, limit creativity, and shut down initiative. A more powerful approach is to ask questions that help them notice when they are “shoulding” themselves and encourage them to reframe it into what they want to or get to do. That simple shift builds awareness across the team and creates a culture of choice and possibility.
If you are noticing too many shoulds in your own head, the first step is simply awareness. Pay attention to when you are “shoulding yourself.” That awareness alone is powerful because it takes what has been running in the background and brings it into the light. Once you see it, you can change it.
This is where The Clarity Compass comes in. It provides a practical way to explore your readiness for leadership and move past the weight of shoulds:
- North: Why. Why is leadership important to you? Ask yourself this question more than once. Each answer takes you closer to the heart of your purpose. Is it about serving your industry? Strengthening your community? Supporting the people you lead? Knowing your why creates fuel for when leadership feels hard.
- East: What. What kind of leader do you want to be? And just as important, what kind of leader do you not want to be? Think about leaders from your past who inspired you and those who drained you. List the qualities on both sides. This is your chance to paint a picture of the leader you want to grow into.
- South: Who. Who do you admire? Who are the leaders you look up to? If you can recognize qualities in them, it’s because those qualities exist in you too. Who are the people you don’t want to emulate? That awareness matters as well. And most importantly, who are the mentors or peers who can walk alongside you as you grow? Leadership is not a solo sport.
- West: How. How will you move forward? One exercise I use is drawing a simple organizational chart on the back of a napkin. At the top, write your leadership goal — something you want to pursue. On the next line, list the categories or focus areas needed to reach it. Under each, write the specific actions or projects that will move you closer. This turns possibility into a plan.
- Center: Now. Once you’ve worked through the Compass, don’t let it sit on the shelf. Within 48 hours, choose one action you are willing to take. It can be small — scheduling a conversation, reaching out to a mentor, reading an article, or journaling on your why. What matters is that you do something now. That is your next clear move.
This compass provides direction for your leadership. The “shoulds” that don’t align with this direction need to be challenged. That gives you Clarity of direction, and less stress!
Reflection Prompt / Exercise
Take ten quiet minutes this week. Write down every time you hear yourself say or think “I should…” Then go back and replace each one with “I choose to…” or “I want to…” Notice how it feels different in your body and your mind. This simple swap can shift the way you see your options.
If you are carrying the weight of too many shoulds, give yourself permission to set one down this week. Choose curiosity over pressure. Choose readiness over rules. That single shift could change how you lead and how you live.
Ready to drop a “should” and explore what’s possible instead? Visit my website to explore resources, programs, and tools designed to help you and your team take your next clear move.
