Spooky Season: The Thrills and Chills of Shooting Your Shot as a Small Business Owner

side by side image of Dee from Lovecraft Country and Founder Leah


As October ushers in the delightful chills of the “spooky” season, memories of my childhood resurface—memories of a different approach to Halloween. Growing up, my brother and I were encouraged to embrace the whimsy of Winnie the Pooh, and Willy Wonka rather than the terror of frightful figures. In our household, there were no zombies, witches, ghosts, or masked murderers. Instead, our parents nurtured creativity and guided us to approach costumes from a more positive mindset.

Our Halloween traditions took a unique turn. While other children embraced fake blood and bone-chilling masks, my brother and I reimagined superheroes and the decades of our parents’ generation. Instead of dwelling on darkness and death, we leaned into the vibrancy of life. And my father, in an act of unwavering love and support, even took a sewing course to craft my very first Halloween costume—a magnificent tiger outfit that I proudly wore for two consecutive years.

As I reflect on those cherished memories, I realize that my upbringing has profoundly shaped my journey as a small business owner. It's a journey that mirrors the thrills and chills of the spooky season in more ways than one.

The Haunting Uncertainty of Small Business

Much like the uncertainty of Halloween night, the path of a small business owner can be equally unsettling. The unknown looms like a fog, casting shadows of doubt and apprehension. But just as my parents encouraged us to embrace creativity over fear, so too must we face the unknown with courage and resilience.

One recent, spine-tingling experience for me was stepping into the role of an in-kind sponsor for a virtual project management summit. As a small business owner, offering our products and services in such a capacity can be akin to venturing into a haunted house. The fear of the unknown—will it pay off, or will we be met with disappointment?—lingers like a ghostly presence.

The Ghoulish Delight of Collaboration

In the world of small business, collaboration is often the source of enchantment and opportunity. Recently, I had the spine-tingling pleasure of collaborating with likeminded content creators. These creators, with their unique voices and engaged audiences, offer a chance to showcase our pins in a whole new light.

But reaching out to content creators and pitching to publications can feel like summoning spirits from the beyond. The uncertainty of their response, the eerie feeling of vulnerability—it's a journey not for the faint of heart. Yet, in these moments of trepidation, we often discover the most thrilling surprises.

Embracing the Fear and the Fun

As small business owners, we must learn to embrace fear and creativity. Just as my childhood Halloween costumes were born from creativity and positivity, so too can our ventures thrive in the face of uncertainty. The path may be shadowy, but it's also where we find our greatest growth and fulfillment.

This Friday the 13th–in October no doubt–as we prepare to welcome Halloween with open arms, let's also welcome the shocks and surprises that come with running a small business. Embrace the fear, feel the adrenaline, and remember that every daring step you take is a chance to grow.

G’head. Join us on this spirited journey. Shoot your shot. Use this contact form to connect with us.

In the end, whether it's a Halloween costume or a small business venture, it's the spirit of creativity and community that illuminates our path and helps us overcome any darkness. So, let's keep shining our light, embracing the challenges, and making this spooky season—and every season—a time of thrilling adventure and growth.

- Leah

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