Sometimes you’ll miss (keep showing up anyway)

Lesson #30 of 40

As I approach 40, I’m embarking on a year-long project to reflect on the lessons I’ve learned in four decades of life. This is lesson #30. You can read the full series here.

Warning: I took a swing at a few sports metaphors. (Getty Images)

I’ve had a pretty good run lately. My first lesson of 2025, about getting in front of the camera, resonated with many of you. My thoughts on the ephemerality of life landed well, too. Readers left the loveliest, most thoughtful comments on another recent post, and I even posted a Note that gained surprising traction (whatever that’s worth).

Outside of Substack, I’ve had other wins. Just last week I got positive feedback from new clients, negotiated for more consistent pay, and delivered a well-received presentation. I’m making steady progress on my novel, waking up early, taking daily walks, and — after years of resisting — starting my days with Morning Pages. (I’m loving it, just like everyone said I would.)

It all feels great — except for the tiny, persistent voice in my head: This won’t last.

That voice is a real party pooper. Why ruin a good time? But it’s not wrong. Highs like these don’t last forever. And while I sincerely hope everything doesn’t come crashing down at once (universe, this is not an invitation!), I know I’m not going to maintain an unbroken streak of hit after hit. Especially not in the strange, fickle world of newsletters.

Here’s the hard truth: Sometimes you’ll miss.

I know from experience. I’ve written plenty of essays that didn’t connect with readers, sometimes because my ideas didn’t resonate, other times when I fumbled the framing. I’ve sent out posts I later regretted — either because the quality was subpar or my reasoning was too limited. And I’ve lost count of the times I poured my heart into an essay I expected to be a banger — a dazzling firework illuminating the dark sky! — only to watch it fizzle.

I’ve published essays I adored, then watched the unsubscribes roll in. Agonized over phrasing, only to receive emails pointing out how I got it wrong. Sent vulnerable appeals for paid subscribers that have been met with crickets.

I know this is part of the deal when you put yourself out there — the cost of creative, heart-centered work. And I know I’m lucky to have the readership I do. My positive interactions with readers far, far outweigh the negative ones. Still, publicly chasing a dream is hard. Especially if you’re a perfectionist.

And I am. I want everything to be, if not perfect, at least up to my high standards. I’m not great at cutting myself slack, half-assing things, knowing when to relax and let things go. (I would venture to guess this is true for most of us who are bold and silly enough to write newsletters.)

But the real struggle of perfectionism isn’t the impossibility of perfection — it’s the constant feeling of failure.

I’ve long lived as if there’s a silent critic in the corner, watching and grading me. Is my kitchen clean? Do my pants fit? Did I complete everything on my to-do list? Did I journal, meditate, exercise? Did I try hard enough? Did I make it all look effortless? The critic wields their clipboard, scribbling notes, mouth set firmly in a frown. No matter how much I do or what I achieve, I can never seem to please them. I’ll never earn that elusive gold star.

So why do I even try? Squaring the truth of this lesson — sometimes you’ll miss — with the ever-present fear of failure is a major challenge. It’s tempting to not hit publish. To remain quiet. To stay on the sidelines. Because if you don’t try, you can’t fail.

Except, it doesn’t quite work out that way. Not trying is the real failure.

By publicly committing to publishing 40 lessons in a year, I set myself up for the possibility of failure. I could burn out. Miss one too many weeks and fall off schedule. Write something so bad that all my subscribers run away.

But I didn’t. I haven’t. (Yet!) With just 10 lessons to go, I feel pretty good about my chances of hitting my goal by my 40th birthday in April. In the past, I’d let my inner critic keep me from writing. I’d scamper back to the bench whenever the doubts got too loud. This time, I’ve learned to tune them out and stay in the game.

And while not every lesson has been a hit (there have been a few whiffs for sure), I’m pretty happy with my batting average. I’m proud of how I’ve kept showing up, week after week.

As I get older — and farther from the environments that rewarded my perfectionist tendencies — I care less about that clipboard-wielding judge and more about the softer side of myself. The side that journals and meditates not to maintain an unbroken streak but because it creates a gentler start to my day. The side that writes because writing feels good, not because I’m climbing up some imaginary leaderboard. The side that knows I am enough, regardless of what I accomplish.

In other words: I care less about pleasing others and more about being kind to myself. Sometimes I’ll miss — and that’s okay. As long as I keep showing up, I’m winning.

They can’t all be hits. And that’s a good thing! The misses make the wins more exciting, for the people who are putting themselves out there and the folks cheering them on. What matters is the act of trying, especially when success isn’t guaranteed. Even knowing that you might miss. Because you will sometimes miss. Life is annoying and wonderful that way.

You can’t predict the outcome — of a baseball game, a newsletter post, or even a single day in your life. That’s the magic. The only way to find out what happens is to keep showing up.

xoxo
KHG

Speaking of showing up (a tiny postscript)

It can feel hard to do. Especially in the depths of winter. Especially when political and world events are so heavy, so dynamic, so distracting. Especially if you’ve been hit by a grief wave, like I have this week. (Hi! I’m over here doing my best to tread water alongside you.) One of the perks of the 40 Lessons series is not having to process things in real-time, but I worry that it can sometimes seem tone deaf. Times are tough right now. I know. If you’re having a particularly hard week, you’re not alone. ♥️