A Spooky Season Letter About Letting Go, Ghosts, Pumpkins & the Dark

Every fall, trees perform one of the most dramatic acts of letting go imaginable. They spend months growing beautiful leaves, nourishing them, showing them off — and then basically say, “Well, your season here is complete,” and drop them all over our lawns.

No guilt. No twelve-paragraph explanation. No keeping one dead leaf around because “we’ve been through so much together.”

Meanwhile, humans will cling to an outdated belief, habit, expectation, relationship dynamic, or version of themselves for YEARS because letting go feels like admitting it never mattered.

But letting go does not mean something was meaningless. Sometimes it means it mattered exactly as long as it was supposed to.

One of the questions I love in coaching is: What are you carrying simply because you’ve gotten used to carrying it?

Maybe it’s the belief that you have to make everyone happy. Maybe it’s a goal you chose five years ago that no longer fits who you are (or that you just don’t give a damn about anymore). Maybe it’s the expectation that by this age you were supposed to have everything figured out. (Spoiler: apparently nobody received that instruction manual.)

Fall gives us a visual reminder that release can be healthy, necessary, and even beautiful.

You are allowed to outgrow things without turning them into villains first.

You can appreciate what something — wait for it… or someone — gave you and still decide it doesn’t belong in your next season.

The trees certainly aren’t scheduling closure meetings with every leaf.

Spooky season loves a good ghost story. But some of the most persistent ghosts are considerably less exciting than the ones haunting Victorian mansions.

They sound more like:

Ah yes. The ghosts of criticism, rejection, embarrassment, old mistakes, and Former You. These ghosts are sneaky because they often disguise themselves as facts. Something happened once, and your brain — ever the overachieving safety officer — decided it should create a permanent policy around it.

You failed at something, so now you’re “bad at it.” Someone rejected you, so now you’re “not enough.” You made a decision you regret, so now you “can’t trust yourself.”

That isn’t always truth. Sometimes it’s just an old story with excellent special effects.

Personal growth doesn’t require pretending the past didn’t happen. It means learning to notice when yesterday is trying to make today’s decisions. Your past does get a seat at the table. It can provide information. It can share lessons.

It does NOT automatically get the deciding vote.

Just because a ghost from your past comes knocking doesn’t mean you have to let it move in rent-free. Sister, this isn’t a haunted Airbnb!

Okay, next let’s talk pumpkins.

Nobody walks into a pumpkin patch, selects a pumpkin, brings it home, places it on the kitchen table and screams, “WHY AREN’T YOU A JACK-O’-LANTERN YET?”

We understand there is a process. You choose what you want. You make a plan. You cut into it. You scoop out an alarming amount of goo. Things get messy. You question your artistic ability. You spill a little wine. Sometimes you cry a little. You might even cut yourself. Eventually, something begins to take shape.

Life is weirdly similar. We often say we want change while continuing to build our lives around everything except what matters most to us. We want more peace but keep saying yes to things we resent. We want confidence but wait until we feel completely fearless before taking action. We want time for ourselves but somehow everyone else gets first dibs on the calendar. We want a different life but we keep protecting the exact routines that created the current one.

Intentional living requires asking a slightly uncomfortable question: Does the way I spend my time, energy, attention, and resources actually match what I say matters to me?

That question can sting a little. Good. Pumpkins don’t become jack-o’-lanterns without a little carving.

You don’t need to redesign your entire life this weekend. Start small. One boundary. One habit. One honest conversation. One hour reclaimed. One decision that sounds more like you.

Transformation is often less dramatic than we imagine. It’s usually a collection of tiny choices that eventually become a very different life.

Fall changes the light. The evenings arrive earlier. Shadows stretch longer. The bright, endless feeling of summer gives way to something quieter.

And culturally, we’re not exactly subtle about our relationship with darkness. Darkness is scary. Light is good. We want clarity, certainty, answers, five-year plans, and preferably a brightly illuminated sign saying, “YES, THIS IS DEFINITELY THE CORRECT DECISION.”

Unfortunately, personal growth rarely provides airport runway lighting. Sometimes you don’t know. You don’t know whether the new path will work. You don’t know whether you’ll succeed. You don’t know exactly who you’ll become. You don’t know what happens three turns from now.

And that uncertainty can make us freeze. But self-trust isn’t believing you can predict everything that will happen. It’s believing you can meet yourself there when it does. That distinction changes everything.

You don’t need enough light to see the entire road. You need enough to see the next step — and enough trust in yourself to believe you can figure out the step after that when you arrive.

Maybe courage isn’t finding the light switch.

Maybe courage is realizing you’ve become someone who can carry a candle.

And maybe, if we really get lucky, the lighthouse beacon for others.