Could Santa Claus Have “Impostor Syndrome”? And What That Means for Small Business Owners
Hey there, fellow workplace wanderers. It’s your Millennial HR specialist here, taking a look at one of the busiest professionals of the season through a different lens.
We wouldn’t dream of questioning Santa’s existence, but when you look at the magnitude of his to-do list, it becomes clear why small business owners might see a bit of themselves in the man in red.
*NOTE: I’m not a business owner but I do sit and stare dead on at one *cough Tami* every day and see how navigating and carrying the daily work can cause questions. **NOTE 2: Like Santa, she is a legendary gift giver too.
Santa’s “Job Description” Is Huge and Very Real-Life
If we think about Santa’s work the way we think about any large organization, the parallels get surprisingly clear:
a massive team to coordinate
quality products to deliver on a strict timeline
reputation management
customer satisfaction
an annual deadline that does not budge
If he experienced the kinds of thoughts humans often do under pressure, he might occasionally wonder: Am I doing enough? Am I keeping up with expectations? What if I don’t get everything done exactly right?
Those are classic notes of impostor syndrome. Doubting your worth. Worrying someone will see the cracks. Attributing success to luck instead of skill. Many leaders know those feelings well.
From Santa to Small Business Owners: The Familiarities
Small business owners wear many hats on any given day. CEO, scheduler, customer service, HR, strategist, sometimes janitor. It’s a lot. And even highly capable entrepreneurs admit they sometimes feel like they’re winging it.
Research backs this up. A survey of more than 600 entrepreneurs found that 84 percent experience impostor syndrome at moderate, frequent, or intense levels. Many worry about being “found out” as lacking knowledge, even when their businesses are thriving. Others chalk up success to luck rather than their own work.Kajabi+1
If we apply that lens playfully to Santa’s operation, it’s easy to imagine similar themes. That constant mix of expectations, responsibility, and tradition could feel very familiar to anyone trying to keep a small business running well.
When Doubt Isn’t Always a Problem
Here’s the twist. Impostor syndrome doesn’t necessarily mean failure. In fact, those feelings often show up most in people who care deeply. Many small business owners are perfectionists or deeply invested in doing things right. They want to serve well, lead well, and build something worth being proud of. That concern can push people to prepare more thoroughly, learn more consistently, and deliver exceptional service.
In that sense, Santa’s “magic” might rely on a similar kind of care: the desire to get it right, the drive to give more than expected, and the commitment to consistency year after year. That’s not far from what keeps small businesses moving forward with heart and resilience.
When Impostor Syndrome Starts to Weigh Too Much
Of course, doubt has a downside. Impostor feelings can lead to stress, decision paralysis, reluctance to ask for help, or burnout. For entrepreneurs and founders, this can show up as hesitation to grow, avoidance of new opportunities, or a lack of recognition for the value they have already created.
That’s why it matters to acknowledge these feelings rather than pretending they don’t exist and instead reframe them as evidence of how invested you are in your work and your people.
The HR Takeaway: What This Teaches Us About Leadership and Kindness
If Santa were running a small business, he would need more than magic. He would need thoughtful systems, steady support, and reasonable expectations. HR professionals and small business owners alike can take a few lessons from that thought experiment:
Recognize that leaders often carry self-doubt under a very put-together exterior
Build support systems: peers, mentors, or trusted advisors who remind you that success comes from consistency, effort, and care
Encourage balance: overworking might feel productive in the moment but long-term success comes from rest and sustainable habits
Redefine “magic”: focus on reliability, kindness, authenticity, and follow-through
At the end of the day, maybe Santa did have a little doubt sometimes. Maybe he wondered if he deserved all the glory. But he still showed up.
That resilience, showing up again and again even when you feel like a fraud might just be the most powerful superpower a small business owner has.
Stay real. Stay kind. And keep delivering your kind of “holiday magic.”
— Sarah, Your Millennial HR Specialist
NOTE: We did not attempt to reach Santa for comment, for obvious reasons. It is peak season and we would never interrupt someone with that level of year-end operational responsibility. We simply tip our hats to his example and to every small business owner out there doing their own version of holiday magic.