Hey! A Celebration Here and There Won’t Ruin Your Tolerance for Struggle

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Title graphic for Hillary Weiss blog post titled Hey! A Celebration Here and There Won’t Ruin Your Tolerance for Struggle.

The first time I was asked “How are you celebrating?“, I was being congratulated on my first successful course launch, while waiting to walk onto a conference stage to speak.

I stared blankly at the asker.


After I gave my talk, I’d have to sit in the back of the room and finish the post-conference sales emails. And after that, I’d need to retreat to my hotel room to finish another client’s sales page.

“How will I celebrate?” I replied, visibly confused and exhausted. “Uh… sleep?”

Celebration IS a Strategy

The asker said nothing, but cocked an eyebrow as if to say: “Well that doesn’t seem good enough…

*”*He was right. And I never forgot how I froze. How stumped I felt when he asked.

I was making huge strides, but treating them ALL like nothing. And I promised myself: it wouldn’t be that way forever.

That’s why, years later, I consider celebration a core piece of my strategy.

Succeed or fail, I reward myself for my effort with things and experiences that delight me. The only thing that may change is the budget.

“But surely we can’t celebrate ALL the time, right?

Celebrating ourselves for every tiny little thing seems… risky.”

Go Ahead – Be a Celebration Hoe

It’s a concern that’s shared with me often.

Especially when I’m up on my soapbox about the importance of entrepreneurs rewarding themselves, and relishing the top of the mountain for a while… instead of jumping straight to the next one to climb.

Especially when I (half) jokingly call myself a “celebration hoe”.

And truly: what if INDEED?

What if we DID find ourselves in a constant, shameless state of celebration?

What if we danced every morning just because we poured just the right amount of cream in our coffee (and even if we didn’t)?

What if we rewarded ourselves lavishly for simply existing in the world?

What if we celebrated every win, big and small, so outrageously and often that sequins and confetti and champagne become a part of our daily routine?

And my first reaction is always:

“Uhhh that sounds fucking awesome.

Why DON’T we do that?!”

But I do understand the question.

Stop Rationing Your Rewards

Celebration is intended as reward. As something we must earn.

The fear seems to be that a perpetual state of celebration would at best blunt its effects and create complacency, and at worst blind us to the ills of the world.

Which is a truly fascinating concern.

Creative entrepreneurs are OBSESSED with discussing and studying the horrors of our work — contemplating our sweat, our stress, our imposter syndrome, and our burn out.

Even if we’re anti-hustle, even if we consider joy a birthright… we still carefully train ourselves to expect pain, process it, and learn from it.

All the while, we ration celebration by the teaspoon, like sugar. As if too much will erase everything — instantly ruining our appetites, and rotting our teeth.

And as we lean into pain, we tell ourselves we can only celebrate if we stick the landing perfectly.

Why a Little Reward Won’t Ruin Your Tolerance for Struggle

But even when we do? We rush the joy part, too. (Or “reward” ourselves with something practical. Lest we spoil ourselves.)

However, I can personally promise you: lowering your barrier to celebration will NOT ruin your tolerance for struggle.

The first time I forced myself to celebrate DESPITE what was technically a failure (missing a sales goal), I expected to feel like a fool. An imposter. But I didn’t.

Prior to that I would’ve curled up in my bed to stare at the wall, the shame of it all threatening to drown me.

Instead, I treated myself to a beautiful meal, and a piece of jewelry, for taking my best swing and taking the good with the bad.

And it felt like giving myself a warm hug. Like supporting myself completely.

Intentional Celebration Does Not Equal Avoidance

It grounded me in reality that this business ride is wild, but I didn’t need to wait to be perfect to find the good — even in the flops.

It reminded me that this is supposed to be fun. Should be, actually. If we let it.

That’s why I’m here, friend, to encourage you to celebrate yourself. Today. For any reason.

Not to hide from the ills of the world, or numb out with treats and gifts. But to actively demonstrate your worthiness to YOURSELF first. To refuse to dangle the promise of reward just ahead like a dog treat, and instead intentionally build reward in.

Because then, the fear of failure loses juuust a bit of its bite — and you stop trading 10 pounds of pain for a teaspoon of joy.

And who knows? Someday, you might just call yourself a celebration hoe too.


Photo by Amy Shamblen on Unsplash

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