Things That Go Bump in the Night
Fun fact: I love a theme. And lucky for me, Maura, our Administrative Extraordinaire, embraces every theme I throw her way for our monthly newsletter. I also love Halloween because… candy. You should see my desk. (The wrappers tell the story.)
So, in the spirit of the season, I thought I’d share a few of the things that scare me most as a small business owner. Cue the spooky music.
Fear #1: The “What If Something Happens to Me?” Monster
As a small (super small) business, much of WindsorTurner’s work is still handled by me, myself, and I. This isn’t a complaint, it’s just reality. I love what I do: building spreadsheets that make sense, crafting realistic project timelines, finding that elusive last piece of a funding stack. Even writing self-promotional blog posts like this one.
But the thought that something could happen to me—that I couldn’t do all those things—haunts me. Who would pick up the spreadsheets, manage the projects, or finish the applications? This question has kept me up a few nights and reminded me of the value of building true partnerships. Yes, collaboration divides the profits, but peace of mind is worth a piece of the pie.
Fear #2: Health Insurance Horror
Health insurance is the thing that truly goes bump in the night. Not just for me, but for my team. Costs have become ghoulishly untenable. My most recent letter from our carrier proposed that our premium would almost double—on top of an already high-deductible plan we only carry to keep costs “manageable.”
I doubt I’m the first small business owner terrified by this. We can’t simply pass those costs along to our nonprofit clients, and yet while insurer profits soar into the billions, small businesses like mine feel the hit in the thousands. If we want a thriving small business ecosystem, this is a problem that demands real attention. These are answers that I do not have – but putting out to the universe for someone smarter than me.
Fear #3: The AI Unknown
I’ve always embraced technology. In graduate school, I spent more time on the Solow growth model than anyone should (yes, I’m that kind of nerd). But artificial intelligence? It has me… uneasy.
We’re living in the wild west of AI, and I often wonder: What tools should WindsorTurner actually use? How do we safeguard client information? And what level of accuracy can we realistically trust? More than anything, I’m wary of future costs. Remember the iPhone? It started out nearly free, and now you can’t leave the Apple Store for under $1,000. WindsorTurner recently evaluated a $5.9 billion data center project—and I can’t help but think my $29.95 ChatGPT subscription won’t stay that way forever once the tech world decides we’ve all “adopted.”
Okay—maybe this post sounds a little dark for a Halloween blog. But here’s the light: every day, I’m grateful to chart my own course. I’m not frightened by the people, projects, or places that come across my desk. So while I may have the occasional sleepless night, most nights I rest easy—candy wrappers and all.
Happy Halloween. Stay out of the candy bowl.