Running a small business is serious work, but that doesn’t mean you can’t laugh about it. From dealing with demanding customers to juggling endless tasks, every entrepreneur faces moments that are simultaneously frustrating and hilarious. Sometimes the best medicine for business stress is a good laugh—especially when you realize other business owners are going through the exact same struggles.
The Customer Service Chronicles
Small business owners know that customers can be… interesting. Here are some gems that’ll make you nod in recognition:
The Time Traveler
Customer: “I need this rush order completed yesterday.”
You: “Our turnaround time is typically 3-5 business days.”
Customer: “But I have an event tomorrow that I just found out about six months ago.”
The Math Wizard
Customer: “Your competitor charges $50 for the same service.”
You: “That’s interesting—we charge $75 because we include X, Y, and Z.”
Customer: “Can you match their price and keep all your extras?”
You: “That’s not how business works.”
Customer: “But it’s just this once!”
The Negotiation Expert
“I’ll pay you in exposure! I have 47 followers on Instagram, and my aunt shares everything I post.”
The Daily Juggling Act
Running a small business means wearing approximately 847 different hats. Here’s what that looks like:
Monday Morning Reality
9 AM: CEO making strategic decisions
9:15 AM: IT department fixing the printer
9:30 AM: HR department mediating a dispute about the coffee pot
9:45 AM: Janitor cleaning up said coffee pot dispute
10 AM: Marketing guru updating social media
10:15 AM: Accountant wondering where all the money went
The Multitasking Master
You know you’re a small business owner when you’re simultaneously:
On a conference call discussing quarterly projections
Signing for a delivery at the door
Texting your spouse about picking up milk
Wondering if you remembered to eat lunch
Planning tomorrow’s social media post in your head
Financial Comedy Gold
Money matters can be stressful, but they’re also prime comedy material:
The Profit Paradox
Month 1: “We made $10,000 in revenue! We’re rich!”
Month 1 (after expenses): “We have $3.47 left. Anyone know how to make ramen exciting?”
The Invoice Dance
Day 1: Send invoice with 30-day terms
Day 45: Send friendly reminder
Day 60: Send “just checking in” email
Day 75: Send passive-aggressive follow-up
Day 90: Consider becoming a debt collector
Day 91: Payment arrives with note: “Sorry, just saw this!”
Bank Account Philosophy
Small business bank account balance: Schrödinger’s money—it’s simultaneously there and not there until you check it, and checking it changes the outcome.
Technology Troubles
Every small business owner has a love-hate relationship with technology:
The Website Warriors
“Our website is down!”
“Did you try turning it off and on again?”
“It’s a website, not a microwave!”
“Did you try it anyway?”
Website magically starts working
Social Media Struggles
Posted a professional business update at 2 PM: 3 likes
Accidentally posted a blurry photo of your lunch at 11 PM: 47 likes, 12 comments, 2 shares
Email Archaeology
“I know I have that important email somewhere…”
Three hours later, found buried under 2,847 newsletters you never signed up for
Staff And Solo Adventures
Whether you’re flying solo or managing a team, there’s humor everywhere:
The One-Person Show
Boss: “We need to have a team meeting.”
Employee: “It’s just you.”
Boss: “I know. I called this meeting to discuss my performance.”
Employee: “You’re talking to yourself again.”
Boss: “And I have some concerns about my attitude.”
Hiring Hilarity
Job posting: “Entry-level position, competitive salary”
Applicant expectations: “I want to work remotely, set my own hours, and earn six figures while learning everything on the job.”
Finding Humor In The Hustle
So the next time a customer asks for the impossible, your website crashes at the worst moment, or you find yourself having a serious conversation with your office plant, remember: somewhere out there, another small business owner is going through the exact same thing and probably laughing about it.
Quikstone Capital Solutions has officially reached its 20-year anniversary, a moment that reflects two decades of dedication to supporting small businesses across the country. If you need cash for your business, contact us today. We have only one goal: to help your business succeed.
