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How to Finish December Strong: A Whimsical Entrepreneur's Self-Help Guide

Ah, December. The month that sneaks in like a quiet guest and suddenly throws a confetti-filled farewell party for the entire year. Fennel Hudson said it best: "December, being the last month of the year, cannot help but make us think of what is to come." So, dear entrepreneurs and business owners, why not embrace the chaos and magic of December with a self-help guide as zany and unconventional as the business world itself?

Small Business Christmas Party

Here are three utterly silly but possibly life-changing strategies to close out the year with entrepreneurial panache:

1. Host an Annual Board Meeting—With Your Future Self

Why wait for the New Year to start strategizing when you can consult Future You right now? Set up a cozy chair for yourself and an extra (possibly swivel) chair for your future self. Grab a cup of hot cocoa or eggnog, and have an earnest heart-to-heart.

Ask Future You:

  • What genius business idea did we conquer this year?

  • Which mistake became the plot twist in our success story?

  • What’s the one thing we didn’t do that we’re now very smug about not doing?

Sure, your team may think you’ve lost it, but what’s a little eccentricity in the name of visionary business planning? Bonus points if you wear a wizard hat while doing this.

2. Marie Kondo Your Business Goals—With a Holiday Twist

Does your 2023 business plan still spark joy? If not, turn it into snowflakes! Literally. Grab your outdated goals and cut them into festive shapes to hang around your workspace.

Pro Tip for Entrepreneurs:

  • Use this as an opportunity to declutter your mindset. Let go of old, stale ideas and open up brain space for fresh, creative solutions.

  • Celebrate with cookies shaped like dollar signs.

After all, nothing says "I’m ready for next year" like a metaphorical (and slightly glittery) clean slate.

3. Declare a National (or Personal) Holiday: “Almost New Year’s Day”

Why wait until January 1st to reinvent your entrepreneurial wheel? On a random December day—preferably when everyone else is panicking about shipping deadlines—declare “Almost New Year’s Day.”

How to Celebrate:

  • Write down your boldest goals for the coming year, then shout them from the rooftops (or the breakroom).

  • Gift yourself one thing your business truly needs: a new tool, an upgraded coffee maker, or simply a guilt-free nap.

  • End the day with a dramatic countdown to... tomorrow.

Because who needs an official date to declare their brilliance?


December is a time of reflection, reinvention, and just enough whimsy to keep us going. So, dear business owner, take a moment this month to embrace the silliness of life, the outrageousness of your own ideas, and the exciting potential of the year ahead. After all, in the words of every visionary entrepreneur: "Why not?"


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