Running a creative business isn’t predictable. One month you feel like you’re on top of the world, and the next month you’re refreshing your banking app wondering how the numbers dropped that fast.
After nine years of running my photography and filmmaking business, I’ve learned one thing for sure:
Cash flow is everything.
And it’s also the one thing creative entrepreneurs rarely have under control.
That’s exactly why Square Loans — specifically Square Working Capital — have become such a big part of my journey. The strange part? Square offered me $12,000 even though my credit still wasn’t great.
I don’t see a lot of creators talking about this honestly, so I wanted to share what these loans actually are, how they work, and how they’ve helped (and honestly, hurt) my business over the years.
Why Square Loans Even Exist for Creatives
Traditional banks care about one thing above all else:
your credit score.
If your score isn’t high, you’re done before you even start.
But Square works differently. They already see your:
- sales
- transaction history
- clients
- overall business activity
So when they make loan offers, they’re not approving you.
They’re approving your sales volume.
That’s why I ended up staring at a $12,000 offer — despite my credit not being where I want it to be.
And honestly? The first time I saw that offer, it felt like a lifeline.
How Square Loan Fees Actually Work
Square Loans don’t charge interest.
They charge a fixed fee upfront.
Example (not exact numbers, but realistic):
- Loan: $12,000
- Fee: ~$1,200
- Total Payback: ~$13,200
The fee doesn’t change.
It doesn’t compound.
You know exactly what you’ll owe on day one.
Repayment happens automatically as Square takes a percentage of every sale you make until the loan is paid off. Some weeks they take a lot. Some weeks they take very little.
But here’s the kicker:
Even if business slows down, they still require you to pay a minimum amount every ~60–90 days.
That’s a detail a lot of people miss.
How Square Loans HELPED My Business
1. They’ve saved me during slow seasons
Creative income is not consistent.
My busy months have hit over $17,000.
But I’ve also had months as low as $7,500 — and that’s scary when you have a family.
Square loans have helped me:
- pay rent
- buy new equipment
- invest in bigger projects
- stay afloat when cash flow dipped
- take on opportunities instead of saying no
There have been times I genuinely don’t know what I would’ve done without them.
How Square Loans HURT My Business
This is the part nobody talks about.
1. Repayment hits you even when you’re broke
If I had a slow week?
Square still took their percentage.
And that’s when the loan can feel heavy.
2. You start relying on them too often
This is something I had to be honest with myself about.
When cash came easy, I sometimes didn’t hustle as hard.
Or I made purchases I shouldn’t have because I felt “safe.”
That’s on me — but it’s a common trap.
3. The next loan offer comes before the first is paid off
Once you’ve paid back ~75–80% of a loan, Square usually offers you another one.
It’s tempting.
It feels like a reward.
But it can become a cycle.
A cycle that keeps you afloat… but also keeps you in repayment mode forever.
So, Should You Take a Square Loan?
Here’s the honest truth:
Square Loans are not “good” or “bad.”
They are a tool.
If you:
- have steady sales
- need cash flow now
- know EXACTLY what you’re using it for
- have a slow season coming
- or you have a high-ROI purchase to make
…then it can genuinely help your business grow.
But if you:
- have inconsistent income
- don’t have a plan
- struggle with financial discipline
- or treat the loan like “extra money”
…it can hurt you more than help you.
Only you can decide which side you’re on.
Why I Still Talk About This Openly
I’m a creative.
I’ve made mistakes.
I’ve taken risks.
I’ve had months where I feel unstoppable and months where I feel like I’m barely hanging on.
I just don’t want other creators to feel ashamed or confused about their financial decisions — especially when we’re all out here trying to build something meaningful with our art.
Whether you take a Square Loan or not, I hope this helps you make a smarter decision than I did in my early 20s.
Keep creating,
Cole Connor
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