Why "Why Isn’t This Working?" Is the Wrong Question

(And What to Ask Instead to Create Forward Momentum)

If you’ve ever found yourself whispering (or yelling), “Why isn’t this working?”; you’re not alone. My clients ask it. I ask it. You’ve probably asked it too.

Especially when you're doing everything "right." Putting in the time. Following the plan. Executing with commitment. And still… the result feels unclear, misaligned, or delayed.

But here’s the hidden problem with that question: It immediately positions you as the problem. And the process as broken. It shifts your brain into evaluation mode without clarity; and worse, it filters your attention toward what’s not working. What’s missing. What’s wrong. Even if there’s powerful momentum building just beneath the surface.

The Question Shapes the Data

When you ask, “Why isn’t this working?” your brain (being incredibly efficient) will go find all the reasons it isn’t working.

You’ll:

• Dismiss the things that are working

• Ignore small wins as irrelevant

• Overlook patterns that could be optimized

• Miss the gold in what you’ve already created

But when you change the question to something more strategic like:

• What’s working here (even partially)?

• What data is this giving me?

• What needs to be released, reworked, or reimagined?

Suddenly you’re not just collecting disappointment, you’re extracting direction.

Progress Isn’t Always Loud

Often, what’s working doesn’t shout. It’s subtle. It’s quiet. It shows up as:

• Greater ease in execution

• Less resistance to showing up

• More clarity in what you don’t want

• A calm decision to pivot instead of quit

These aren’t signs of failure. They’re signs of growth. But if you’re measuring your progress only by a specific metric or outcome, you might miss the transformation that’s already happening.

This Is How You Stop “Starting Over”

Every time we label something as “not working,” we risk trashing useful data. And when we trash the data, we start from scratch. That’s what creates the “I keep starting over” cycle.

The solution? Keep the data. Drop the drama. You don’t have to start over if you evaluate with clarity, self-trust, and a willingness to refine.

Sometimes, what’s “not working” is just the thing helping you uncover your next best step.

Self-Trust in the Evaluation Process

Here’s what I tell my clients: You don’t have to make every plan perfect. You just have to make it work for you.

That means:

• Allowing imperfection without panic

• Evaluating results without self-judgment

• Seeing self-trust as a strategic filter not a fluffy concept

Because when you believe in your ability to pivot, adjust, or stretch through discomfort, you gain something far more valuable than fast success: sustainable success.

Want Help Turning Uncertainty into Clarity?

My private podcast on Mastering Inner Dialogue walks you through the exact conversations that shape our follow-through, evaluation, and ability to move forward—especially when results aren’t what we expected.

🎧 Click here to access the private podcast now → (Just 22 minutes of listening that could completely shift your momentum.)

Let’s end with better questions:

What’s working? What’s this telling me? What will I carry forward?

You’re not off-track. You’re just gathering the data to do it your way.