ANNA BERGSTROM

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Stop “Shoulding” Yourself

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ANNA

I work with high-functioning leaders and entrepreneurs who've outrun the tools that got them here. The pattern underneath the problem is where we start.

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Somewhere in you, there’s a quiet, clear read. This isn’t it.

Then a tightening in your chest. And right behind it, a louder voice argues back. But I should.

Notice the order. Your body spoke first. Your brain answered back.

After the brain answers, you probably start rationalizing the thing it thinks you should do. For example, a career decision, a job, a next move the brain thinks you should make: “I should make this move because…”

  • …the pay is good.
  • …the title is impressive.
  • …people will get it when I explain it.
  • …everyone will be glad for me.

Or, maybe your brain thinks you should do everything yourself. Spin all the plates. Fill all the slots on your calendar. “I should keep doing things this way because…”

  • …I’ve always done it this way.
  • …things will fall apart if I don’t.
  • …they’re depending on me for this.
  • …it’s faster if I just do it myself.

Notice what these lists have in common: you were willing to invest significant time and energy rationalizing why the should makes sense.

Meanwhile, the original thought, this isn’t right, was quietly swept away.

So here’s the real question: what made you invest significant effort into the second thought, the brainy one, and dismiss the first, the body one?

Here’s my hunch: we’re wired to move away from ambiguity and toward clarity. Biologically speaking, clarity means safety. Will I get eaten by a bear? is a dangerous question to sit inside of. I will not get eaten by a bear is a relief, whether or not it’s actually true.

Your inner knowing, this isn’t right, doesn’t offer that relief. It tells you what’s wrong without telling you what’s right. So your brain reaches for the should instead. Never mind that it was never actually tested. It just feels resolved. And resolved reads as safe.

The should also hands you a well-defined path forward, a job you should want, a task you should keep doing yourself, but it never factors in whether that path is actually right for you. Your inner knowing would factor that in. It just doesn’t come with directions.

Here’s the thing: you don’t have to choose between the clarity your brain craves and the knowing your body already gave you. The knowing is where the clarity actually comes from, you just have to catch the moments you’re dismissing it, and ask it a better question. What, specifically, feels off? What would need to be true for this to feel right?

That doesn’t take a grand gesture, quitting your job, reinventing how you show up. It starts small: catching the moment you brush the knowing aside. It’s seeing, specifically, what’s actually yours to carry, and what never was, whether that’s a job offer you’ve been talking yourself into, or a task you’ve been gripping out of habit.

Once you see that clearly, it applies everywhere else too: the career change, the business decision, how you spend your time. All of it, measured against your goals, your needs, your values. Not anyone else’s.

So start here. Next time you feel this isn’t it, and the should is already building its case: pause. Rewind. And ask it a better question: What, specifically, feels off? What would need to be true for this to feel right?

Questions for reflection:

  • Where have you felt this isn’t it, and reached for a reason to move forward anyway instead of sitting with it?
  • What have you been rationalizing because it’s clearer than the alternative, not because it’s right for you?
  • Where could you invest your time and energy gaining real clarity, instead of convincing yourself of something you already know isn’t yours?

If this resonated, I work with leaders on exactly this kind of pattern (the one underneath the problem, not just the problem itself). Book a free discovery call to explore together.

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