Let Your Heart Land: What Hailey Whitters Taught This Non-Country Fan About "Should"

I'll be honest with you, I am not a country music person. So when I first heard Hailey Whitters' Heartland, I wasn't expecting it to stop me in my tracks. But it did because of one word she kept repeating in the opening verse: Should.

"I should be married by now. Two kids in a paid-for house."

Oh. Oh. There it is.

"Should" Is the Ultimate Stress Activator

In the world of stress management, we talk a lot about cognitive distortions — the mental habits that quietly fuel our anxiety, our burnout, and our sense of never being enough. And "should" is one of the most insidious of them all.

I should have gotten that promotion by now.  I should be further along in my career.  I should have made different choices.  I should be somewhere other than where I am.

Every "should" is a quiet indictment. It's a comparison between where you are and some imagined, idealized place you were supposed to be. And here's the sneaky thing about "should", it sounds like motivation, but it usually functions as shame. It doesn't move you forward. It just makes you feel like you're already behind.

Hailey Whitters packs four "shoulds" into the first eight lines of her song, and I felt every single one of them. Not because her life mirrors mine, but because the feeling behind those words is universal. The sense that time is flying and you don't have enough to show for it. That somewhere along the way, you made wrong turns, missed windows, fell short of some invisible benchmark that someone — society, your family, your younger self — set for you.

Comparison Is a Thief (And Not a Very Honest One)

Here's a question I ask my clients, and I'll ask it here too: How does comparing yourself to some other version of your life serve you?

Not a rhetorical question. Really sit with it.

When you measure yourself against where you "should" be, you are comparing your real, lived, complicated, full-of-context life to a version that never existed (okay, maybe in the multiverse but this isn't Marvel). You're not comparing yourself to an actual person — you're comparing yourself to a fantasy. And the fantasy always wins, because it never had to deal with what you've actually dealt with.

Comparison also tends to be wildly selective. We compare our insides to other people's outsides. We compare our worst moments to someone else's highlight reel. We almost never say, "I should have had their hard days too." We just want the outcome, divorced from the journey.

Whitters captures this perfectly in her pre-chorus:

"I've been on the rocks, I've been on the road

On the other side of every door closed." 

That's the part we leave out when we "should" ourselves. We forget the rocks and the road. We forget the closed doors. We just see the gap between where we are and where we imagined we'd be — and we call it failure. So how do we mind the gap?

The Mall Map and the Vision Board

A few years ago, I made a vision board. You know the kind — images, words, intentions for the life you want to build. But somewhere in the middle of it, I did something a little unconventional. I put a mall map icon on it.

Specifically, I put that little star and those two words: You Are Here. Not as a reminder of where I wanted to go. As a reminder to be where I am.

Because here is where I've learned, both personally and professionally: the present moment is the only place where life is actually happening. The past is a memory. The future is a projection. Right now, this day, this version of me is the only place anything real can occur.

What if, instead of "I should be somewhere else," you asked: What if I appreciated more of where I am - what I am learning, growing, and becoming?

Let Your Heart Land

The chorus of Heartland is the antidote. After all those "shoulds," Whitters doesn't offer a pep talk or a to-do list. She offers a landing:

"Yeah, you gotta let your heart land."

I love this so much. Not "fix yourself." Not "try harder." Not "pull yourself up by the bootstraps." Just land. Come back to yourself. Find your footing.

In the final chorus, she adds:

"You gotta let your heart land / In the middle of nowhere."

The middle of nowhere. The place that doesn't look like the destination you planned. The ordinary Tuesday. The life that doesn't photograph as well as you imagined. That's where she's asking you to land because it's actually where you are — and there is so much there if you allow yourself see it.

This is what appreciation does. It doesn't require your circumstances to change. It asks you to change your relationship to the circumstances you already have.

A Few Questions to Sit With

I'm a coach, so I can't help myself — here are some gentle prompts to take with you:

• What "shoulds" have been loudest for you lately? Where did those benchmarks come from?

• If you removed the word "should" from your internal monologue, what would be left?

• What is one thing about your current life, exactly as it is today, that you genuinely appreciate?

• Where do you need to let your heart land?

I didn't expect a country song to give me a coaching session. But that's the thing about messages that are true and relevant, they find you wherever you are. 

If you're in the middle of "shoulding" yourself to exhaustion, consider this your invitation to enjoy: You are here. And that's a pretty good place to start.