You know the feeling.

You wake up with a mental checklist already running. You should respond to emails first thing. You should stay late at work. You should be grateful for the job that pays the bills, even if it drains the life out of you.

And if you dare to think about doing something different—something for yourself—here comes the guilt.

We’ve been conditioned to believe that success comes from fulfilling expectations—not necessarily our own, but the ones imposed on us by society, family, and even our past selves. And that’s precisely why so many people stay stuck: they’re living according to the "shoulds" instead of their true calling.

But what if you could rewrite that script?

The Weight of “Should”

For years, I told myself a story.

I should stay in my high-paying but soul-crushing career because it was “responsible.”
I should put off my dream of starting a business because it wasn’t “practical.”
I should work harder, say yes more, sacrifice, grind.

And like so many people, I confused guilt with discipline. I assumed that if a decision made me feel uncomfortable, it must be because it was the wrong one. But the truth is, discomfort isn’t always a warning sign—it’s often an invitation to grow.

Unfortunately, most people never get past this internal conflict.

They feel the pull toward something different, something better—whether it’s starting a creative project, changing careers, or pursuing a long-dormant dream—but they let the "shoulds" drown out their intuition.

And that’s how years slip by.

But you don’t have to live that way. You can ditch the guilt and pursue your calling—and it starts with one simple exercise.

The “Stop Should-ing” Exercise

Here’s how to free yourself from the expectations that are keeping you stuck.

Step 1: Make a List of Every “Should” in Your Life

Write them all down—the obligations, the expectations, the invisible rules you’ve been following. Be brutally honest.

• I should stay at this job because it’s safe.

• I should always be available to others, even when I’m exhausted.

• I should wait until I have more experience before starting my own thing.

Once your list is complete, sit with it for a moment. Whose voice do you hear in each statement? Is it your parents? A former boss? Society’s expectations?

Often, the rules we live by were handed to us—not chosen by us.

Step 2: Challenge Each One with “What If?”

Next to every “should,” write a counter-question:

• What if staying in this job isn’t actually the safest option?

• What if I set boundaries and people still respect me?

• What if I stopped waiting for permission and just started?

This step is about planting tiny seeds of possibility. When we’ve been stuck in a pattern for years, it’s hard to see an alternative. But curiosity disrupts inertia.

Step 3: Rewrite the “Should” as a Choice

The final step is the most liberating. Rewrite each “should” into an empowered choice.

Instead of:
I should stay in this job because it’s safe.
Try:
I choose to explore new opportunities that align with my values and future goals.

Instead of:
I should be available to everyone, all the time.
Try:
I choose to protect my energy so I can give my best to what truly matters.

Instead of:
I should wait until I feel more ready.
Try:
I choose to act now, knowing I will learn as I go.

By reframing obligations as choices, you reclaim control over your life.

The Permission You’ve Been Waiting For

When I finally did this exercise for myself, I realized something shocking: nobody was actually holding me back but me.

The moment I stopped asking for permission and started listening to my own instincts, things shifted. I left the job that was suffocating me. I launched my business. I stopped proving my worth through burnout and started building something sustainable.

And I never looked back.

If you’ve been wrestling with guilt about making a change, consider this your permission slip. The people who thrive aren’t the ones who followed every rule. They’re the ones who had the courage to question the rules in the first place.

So, tell me: What’s one “should” you’re ready to let go of today?

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