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I Guess I Just Have to Try Harder

What do a young man in prison, a senior struggling with cognitive decline, and a global superstar athlete have in common? All three struggle with feeling like they are “enough.” And all three, to varying degrees, feel like the solution to this feeling of “not enoughness” is to work harder, do better, be better. Which is to say that all three—again, to varying degrees—have a hard time with grace.

One of my tasks as a prison chaplain is to mail away correspondence bible courses for grading on behalf of inmates. Sometimes, I read a few of their answers before stuffing them in the envelope. On a recent Monday at the jail, I was struck by—of all things—the penmanship of one of the inmates. Some of the inmates struggle to read or write generally. So, I am used to barely legible scrawl (both reading it and producing it—my own handwriting is appalling). It’s rare to see meticulous, precise handwriting in the digital age. The penmanship caught my attention, but the inmate’s response to a question kept it:

I know that I have failed a lot in my life. And I sometimes have a hard time believing in God or understanding the bible. I want to be a better person and to do better in my life. I guess I just have to try harder.

A few days later, I was visiting with a senior who has been struggling to come to terms with some cognitive decline. I arrived a few minutes early to discover them in a bit of an anxious state. The source of the anxiety was difficult to pin down—there were no pressing appointments, no immediate crisis to deal with, no family discord or relationship deterioration. This person was just very upset with themselves for not remembering a few names in a family picture, and for failing to keep a few calendar items straight. They felt guilty for this, as if they were somehow failing (failing who? me? themselves? God?).  They shook their head sadly. “I guess I just have to try harder.”

This morning, my wife sent me a link to wellness guru Jay Shetty’s recent interview with tennis legend Novak Djokovic. She knows that I love tennis and figured I’d be interested in hearing a bit more of his story. On one level, I was not surprised to see Djokovic on a self-help podcast like Shetty’s (truth be told, I tend to find Jay Shetty a bit annoying). Djokovic is well-known to be freakishly devoted to his physical health. He made many enthusiastic enemies during the pandemic for refusing the vaccine. He treats his body like a high-performance machine and is hyper-vigilant about what he does and doesn’t put in it. He was even detained in Australia and forced to miss the 2022 Australian Open during peak Covid-madness. It’s not exactly a revelation that someone who is still competing at the highest level in an incredibly demanding sport at the age of thirty-eight is passionately committed to wellness.

So, I wasn’t surprised to hear that Djokovic is all-in on all the physical, mental, end emotional techniques to keep him at the top of his game. I was a bit more surprised to hear him say that even after reaching the absolute pinnacle of the sport—he is statistically the greatest player of all time—he occasionally struggles with feeling like he is “not enough.” He traces this to growing up in war-torn Serbia, to a demanding father, to material poverty and to feeling even as a ten-year-old that he was responsible to save and protect his family. And even now, as one of the most recognizable athletes on the planet, with staggering wealth and success, the feeling never entirely goes away.

Djokovic is a Christian, unapologetically proud to belong to the Serbian Orthodox Church. He speaks about God and purpose and “things happening for a reason” easily and persuasively. But I wonder how he feels about grace. He speaks in haltingly admiring terms about Brian Johnson’s immortality project (a project that seems insane and dangerous to me in countless ways, not to mention a project that is only available to the hyper-rich who have the resources to optimize their bodies). He clearly struggles with the idea of limitations (see a previous post where I reflected on this). His response to feeling like he’s “not enough,” like the inmate in the jail, like the senior at the retirement home, seems to be, “I guess I have to try harder.”

I’m not against effort. I’m not against doing what we can to be the best versions of ourselves. God knows our world could use more people who are motivated, passionate, and who feel a responsibility to use their gifts well rather than zoning out in front of their devices. But ultimately—whether you’re sitting behind prison bars or trudging the halls of a retirement home or competing at the US Open—everyone must accept that “enoughness” is not something that we have to produce or maintain or justify. We must all come to terms with the gift of a grace that goes beyond earning.

This is a hard thing to do. I know this very well. My wife sometimes teases me that my self-worth yo-yos up and down based on how I performed that day on the tennis or pickle ball court after work. I think we very naturally try to justify ourselves in all kinds of ways. It could be sports. It could be fitness or body image. It could be performance at work. It could be academics, degrees accumulated, expertise achieved. It could be the zeroes in our bank account. It could be our social connectedness. It could be our kids and their accomplishments. It could be—indeed very often is, particularly among the young—the impression we’re making online, all the odious metrics of likes and clicks and followers and subscriptions. I think we all have some area of our lives that we look to in order to measure our worth, our acceptability, our “enoughness.”

And none of it works in the end. It may get us through a season in life. We may limp along, borrowing our sense of being “enough” from these various domains of life. But eventually, it will all be taken away. Even Novak Djokovic’s body will one day betray him, to say nothing of yours and mine. Our accomplishments will fade from memory. Pick any way we try to justify ourselves or prove that we’re enough—eventually it won’t be up to the task, and we will have to wrestle with the deep question of how, ultimately, we believe that we are justified. Is it something we achieve? Or it something we are given? It it a trophy? Or is it a free gift?

From a Christian perspective, the answer to the problem of feeling like we’re not “enough” is not “try harder, do better.” It is, “receive the gift of the God who has already demonstrated your worth on Calvary’s cross.” All our trying and our doing—our becoming the best versions of ourselves—should only ever be a grateful response to this free gift, not an attempt to earn it. This is not easy to do. We would prefer to earn, to demonstrate, to rank up, to achieve. Grace is hard because it is radically levelling. We are all in the same boat, whether we’re on a New York tennis court or a southern Alberta prison cell. We don’t like this; we recoil from it. We prefer our illusions of sufficiency and control. Until we aren’t and until we can’t.

Grace is, indeed, amazing; but it is also amazingly hard to accept. It is, I suspect, a truth that we will spend a lifetime learning and living into.


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3 Comments Post a comment
  1. Ryan Siemens's avatar
    Ryan Siemens #

    Yup…Thanks.

    >

    August 27, 2025
  2. Andrew Dyck's avatar
    Andrew Dyck #

    Recently, I had the chance to speak on Psalm 23 at a funeral. I was struck (and stuck) by the second line: “I shall not want.” Without re-preaching that homily, I’ll note here that instead of joining culture’s chorus of “I am enough, ” this Psalm confronts us with “God is enough.” I’m endeavouring (trying?) to embrace that in my prayers since that funeral. Thanks for reminding us that “try harder” can be a ditch (on both “right” and “left” wings of the church).

    August 27, 2025
    • Ryan's avatar

      This is a crucial confrontation! I easily grow weary of the “I am enough” talk that is tethered to nothing more than the self.

      August 28, 2025

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