The Hardest Month: Choosing Joy Over Fear This October

If I had to choose the superior month, it would be October, but not for the reasons you may think.

Yes, it brings beautiful colors. The tree outside my office is turning bright yellow right now—it could rival the sun.
Yes, Trader Joe’s is filled with fun fall flavors and the most beautiful autumnal flowers.
Yes, the air is getting crisper, and as a certified jacket lover who lives in the South, I rejoice.

But October, for me, is the best month because it is the hardest month.
October is the month of change, of shedding, of letting go.
Just like trees outside, October asks you to loosen your grip on what no longer fits and trust that something new is coming.

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On October 14, 2012, I posted this oversaturated photo of a bag of coffee I purchased from T.J. Maxx to Instagram. I bought it for this one simple quote:

I hope to be happier next fall than I am at present, and this hope makes me happier now than I should be without it.

I was 19.

I can’t remember what was happening in my life then, only that I kept that bag on my shelf for years because of that one line.

At 32, I still think about that quote every October.

October has always been that invitation to let go and trust the becoming.

It is the belief that if I can find happiness now — in the uncertainty, in the waiting — maybe there’s even more joy waiting on the other side of release. And if I’m not happy right now, maybe letting go is what creates the space for something better to grow.

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In October 2016, I lived through the loneliest season of my life.
In a foreign country, with no friends or family nearby, I struggled to find my footing. But I worked through the quiet darkness of winter and emerged in spring feeling lighter and steadier. The loneliness faded to just a reminder, a moment of growth.

In October 2017, I said goodbye to my dream of living in Scotland.
The disappointment was bitter — it sat in the back of my throat — but leaving also gave me something more: the space to see what else could belong to me.

In October 2018, I left a toxic job in Boston. Two years later, I said yes to working freelance for a boss who taught me how leadership could look different — someone who made work feel lighter again. And just two years after that, in October 2022, I walked away for a new opportunity — the same one I would eventually be laid off from.

Apparently, October has a way of pruning my life back to what’s real.

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Now, it’s October 2025. And once again, I can feel that familiar ache of change. That quiet knowing that something needs to be released.

Only this time, it isn’t a job, a place, or a person. It’s fear.

Fear is seductive, in a way. It warps your mind. It’s like a warm scarf meant to keep the cold out — but worn too tight, it chokes you.

This October, I don’t want to wear scarves anymore.

If you were to ask about my plans — for work, for life, for love — I’d get defensive because I am afraid.

I fear being judged.
I fear being perceived.
I fear not having enough — money, safety, purpose.
I fear looking foolish, or worse, not being good enough.

Fear has warped my mind so much that even when I can name the lies — that people aren’t judging me, that “good enough” is a myth — fear still whispers louder than reason.

But the truth is, this fear is stealing the joy out of my life. Because when I’m afraid, I hesitate. I overthink. I postpone the very things that make life feel alive.

But joy — joy only exists when you’re willing to try. When you try to create, to connect, to live with intention — even when you don’t have it all figured out.

And maybe that’s the real definition of “good enough.”
Not perfect, not certain, but brave enough to keep reaching for joy.

If joy leads to a creative, expanded, contented life, then this October, I’m choosing joy over fear. I’m choosing to shed what chokes and reach for what softens.

Because “good enough” for me isn’t about achievement anymore. It’s about living a life rooted in joy, not postponement.

So this is me trying.
This is me practicing the letting go.
This is me choosing joy.

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Here’s how I plan to find it this fall (and maybe you can too):

1. Do something new—just for the joy of it.
   I’m finally signing up for a pottery class. Not for a portfolio, not for productivity — just to play again.

2. Plan a solo weekend away.
   Go somewhere that feels inspiring. Bring your favorite book, take yourself to dinner, wander without a plan. There’s something freeing about remembering you’re good company.

3. Make yourself a bouquet.
   Buy grocery store flowers, mix in wild stems, and create something beautiful for no reason at all.

4. Buy the London Fog tea.
   Small luxuries remind you that joy can live in ordinary moments. Brew a cup, light a candle, exhale.

5. Find a way to volunteer in your community.
   Whether sorting donations, helping at a garden, or reading to kids, connection reminds you that joy is shared energy.

6. Tend to something that grows.
   Replant a tired houseplant, add bulbs to your garden, or start herbs on your windowsill. Watching something thrive because of your care is its own quiet rebellion.

7. Unplug for one whole day.
   No scrolling, no checking. Let your attention return to your actual life, the one unfolding around you.

8. Revisit something you loved as a kid.
   Reread the book that shaped you, draw with crayons, make a playlist from your teenage years. Joy lives in familiarity, too.

9. Say no, kindly and completely.
   Protecting your energy is a soft act of rebellion. “No” can sound like freedom when it’s rooted in self-trust.

10. Write yourself a letter from next October.
    Tell yourself what you hope to have let go of and what you hope to have found. Then tuck it somewhere safe.

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