When “Should” Runs the Show: Reclaiming Your Voice in Music and Life

by Sarah Hollandsworth

We’ve all been there, caught in the loop of “shoulds” and “shouldn’ts” that leave us second-guessing our choices. These thoughts often sound like logic, motivation, or discipline, but they’re usually rooted in fear, comparison, or outdated definitions of success. For many musicians, this inner voice is constant and convincing. And often, it’s what keeps us stuck.

Maybe you’ve caught yourself thinking things like:

• I should be practicing more (no matter how many hours you’ve practiced).

• I should have this figured out by now.

• I should take every opportunity, I can’t say no.

• I shouldn’t want something different.

• I should stay in this job. It’s secure.

• I shouldn’t rest. I haven’t earned it.

• I should be further along by now.

• I shouldn’t charge that much, what if they say no?

The problem is, “should” (or shouldn’t) usually doesn’t come from your sovereign, authentic self. It stems from cultural, institutional, familial, or internalized beliefs about who you’re supposed to be. While those expectations may have helped shape your path, they can also disconnect you from what you truly want.

As a coach who works with high performers from a range of backgrounds, I see this pattern all the time. A client wants to pivot careers but thinks, “I shouldn’t leave. I’ve invested so much. What if people think I failed?” Another wants to rest after years of grinding but feels guilty for not saying yes to every gig. A talented performer dreams of starting something new but keeps chasing an outdated version of success that no longer resonates.

This kind of thinking can be subtle. It might show up as over-scheduling, burnout, procrastination, or guilt. You may feel like you’re working hard but not making meaningful progress, or that you’ve achieved things that look good on paper but don’t feel great in your body.

So, what do we do about it?
The first step is awareness. Start noticing when the word “should” shows up in your thoughts or conversations. Then ask two powerful questions:

1. Says who?

2. What do I actually want?

That second question can be surprisingly difficult, especially if you’ve spent years filtering decisions through someone else’s definition of success. Reconnecting with your own voice is a practice. But it’s also an act of autonomy. It’s the moment you begin shifting from obligation to choice.

Let’s say you’re caught in a “should” loop about taking an audition. Pause and ask: Why? Is it because you’re genuinely curious and inspired, or because someone else says that’s what you’re supposed to do? Neither answer is wrong, but noticing the difference puts you back in the driver’s seat.

Or consider the phrase, “I should be further along by now.” Compared to what? A career timeline you created at 18? Someone else’s curated Instagram page? An invisible industry standard that was never actually yours?

“Should” keeps us chasing a moving target. But when we question it, when we pause long enough to hear what’s really true, we create space to design lives and careers rooted in self-trust and intention.

This doesn’t mean abandoning structure, discipline, or ambition. It means realigning those things with the values that are alive for you now. Not the ones you inherited or assumed, but the ones that feel true in your body today. It’s the difference between saying, “I have to do this,” and “I choose to do this.”

Of course, we all have responsibilities and realities to navigate. But even within those, there is often more freedom than we allow ourselves to claim. Shifting from “I should” to “I choose” is a reclaiming of power. It’s how we stop performing our lives and start inhabiting them.

If this resonates, here are a few journal prompts to explore:

1. What’s one “should” that’s recently been running the show in my life or career?

2. What am I afraid might happen if I let that “should” go?

3. What do I want more of in this season of my life?

4. What would change if I fully trusted myself to know what’s right for me?

Whether you're a student mapping out your future, a professional navigating burnout, or someone reimagining what comes next, remember: you don’t have to earn the right to want what you want. You don’t need permission to shift. You are allowed to change your mind. That’s not failure, it’s growth.

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Sarah Hollandsworth is an ICF certified executive coach, strategic consultant, and sales and marketing executive with over 15 years in the music products industry.
sarahhollandsworth.com