The Hidden Cost of Holding On

The Persistence Trap: Why We Struggle to Let Go

We live in a culture that prioritizes persistence. This idea has been deeply ingrained in us. From childhood, we are taught that success comes from hard work persisted in over time, that it belongs to individuals who never give up, who push through obstacles, and who fight for what they desire. While persistence and determination are powerful forces, they can often blind us to reality and prevent us from seeing the dynamic impact of recognizing when to let go.

We have all had times in our life where no matter how hard we hoped and pushed, we just couldn’t get what we wanted.

Yet as soon as we let go of that outcome, we were able to find the same or greater fulfillment in something else.

Sir Thomas Wyatt’s Lesson on Recognizing When To Let Go

Sir Thomas Wyatt’s famous poem Whoso List to Hunt illustrates the truth of unattainable desire better than anything else in literature.

He was a poet who was imprisoned twice during the reign of King Henry VIII—once for suspicion of having a relationship with Anne Boleyn, the King’s second wife.

This poem is often interpreted as an allegory for their relationship.

Somehow, despite the chaotic and revolutionary times in which he lived and his courtier life, Wyatt was able to avoid execution—unlike Boleyn—eventually bringing the Petrarchan sonnet to England.

He is often critically regarded as a secondary figure in the transition period between Chaucer and Spenser, but his alliterative-grounded verse creates a distinctly Anglo-Saxon sound that was widely reevaluated by modernist poets.

The Hunt as a Metaphor for Unattainable Goals

Essentially, the poem presents the extended metaphor of an unattainable hunt.

The speaker chases a deer that ultimately belongs to royalty, so he cannot claim it—exhausting himself in the process.

But the lesson remains clear: there are times in life when chasing a goal, whether that is a person, a dream, or an idea, becomes an act of self-destruction rather than an admirable pursuit of growth.

This poem ultimately teaches us that letting go isn’t an act of weakness or a resignation of failure. Instead, it is a recognition that some things are not meant for us—not because of an inadequacy, but because they do not align with who we are ultimately meant to become.

It’s like that piece of popular wisdom: if you got everything you originally wanted, you would have sold yourself short.

Ultimately, we have a limited idea of what makes us happy, while the universe has the full perspective.

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When Love Isn’t Enough: The Painful Truth About Chasing Someone Who Won’t Choose You

Perhaps the easiest way to see how this poem plays out in our own lives is to think of a past relationship that went sour.

One of the most painful lessons we can learn in life—and yet one of the most necessary—is that love is often not enough.

We live in a culture that depicts love as the great conqueror.

We are told that if we only love someone deeply enough, that emotion alone will overcome any obstacle. But love, much like success—however you define it—is not just about how much we may want something.

More often, it is about timing, alignment, and a mutual willingness to participate and grow.

I’ve been in relationships, sometimes over the course of a few years, where I pursued women who remained emotionally unavailable.

They would show glimpses of affection but could never commit or remain open.

I had convinced myself in each case that if I were patient enough, if I loved them enough for long enough, they would eventually wake up to what the relationship was and choose to love me back in the way I needed.

But this is a one-sided, mistaken view of love.

Love isn’t a prize to be won or a rational realization—it is a connection that must be freely given.

The Cost of Fixating on an Unreachable Dream

In Wyatt’s poem, the speaker realizes this distorted relationship too late—just as I did, just as we all do.

He confesses that he is “wearied” from chasing the deer, and yet he is obsessed with her.

He cannot take his mind off of her. And yet he recognizes that this chase has been futile—like trying to “hold the wind.”

When we tie our happiness, fulfillment, or sense of worth to an external outcome, we can get caught up in this state of mind.

Not only in our personal or romantic relationships, but in any area of life where we start to think:

“If only I had… If only I was… If only I did… then I’d be fulfilled.”

This chase is not only exhausting but can be self-destructive.

How many people fall prey to misery and depression as a direct result of chasing someone who didn’t choose them back?

I know this pain personally.

I have made myself sick over trying to get someone to choose me because my own sense of self was directly tied to their approval.

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Read The Poetics of Fulfillment: Why Chasing Happiness Is Killing Your Fulfillment (And How to Stop) 

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Recognizing When To Letting Go Creates Space for Something Greater

Letting go, in this context, is not about giving up on love and joining a convent.

It is about making space for the right kind of love—the kind that doesn’t require endless chasing or a test of endurance.

In order to bring new furniture into a room, we must make space for it by removing what is currently there. Only then can something new flow in.

Nature abhors a vacuum.

Recognizing when to let go means understanding that no matter how much you may love or care for someone, their inability to love you in return is not a reflection of your worth.

It is simply a sign that they are not part of your path.

Quitting Can Be the Smartest Move You Make

Wyatt’s speaker, after much struggle, finally admits that his chase is futile. He realizes that the deer is not his to claim in the first place, no matter how much he wants her:

“There is written, her fair neck round about: / Noli me tangere, for Caesar’s I am.”

This lesson extends far beyond love.

Just as we can fixate on the wrong person, we can also get caught up in the wrong career, the wrong goal, or even the wrong idea of success.

We live in a culture that glorifies persistence and often equates quitting with failure.

But sometimes, quitting something that isn’t serving us is the most intelligent decision we can make.

Success Isn’t Just About Effort—Recognizing When To Let Go

Consider someone who has spent years striving in a career that doesn’t fulfill them. Perhaps they chose the profession because it was prestigious, or to please their parents or partners, or because they once felt it was their true calling.

But when something is misaligned, it eventually leads to unhappiness, burnout, and, often, stagnation.

At some point, you must ask yourself:

“Am I struggling because I need to try harder, or because I need to change direction?”

I know this feeling all too well.

I remained trapped in a career I hated because I was afraid to admit I had made the wrong choice. I feared what others would think, feared losing status, feared being seen as weak.

But holding on and pushing harder wasn’t resilience—it was literally killing me.

Once I recognized when to let go, I was able to be honest with myself.

This idea of success wasn’t serving me anymore.

By pivoting, I found something that sparked joy and excitement in my life.

Letting go wasn’t failure. It was clarity.

The Question You Must Ask Yourself

Letting go requires immense strength.

It takes courage to walk away from something you once wanted with all your heart.

It takes wisdom to recognize when a path is leading nowhere.

And it takes self-respect to choose peace over endless struggle.

Wyatt’s speaker eventually reaches this point of realization.

He knows he must leave the chase behind, no matter how much it pains him.

His final words—“wild for to hold, though I seem tame”—suggest an acceptance of the truth: some things are not meant to be possessed, no matter how much we desire them.

Now, ask yourself:

What are you holding onto that is holding you back?

And what might happen if you finally let it go?

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