Most business owners choose a higher deductible to save money.
On paper, it makes sense.
Lower premium.
More control.
“Self-insure the small stuff.”
But here’s the part most people don’t think through:
A deductible is not just a number.
It’s a cash flow decision.
I’ve seen businesses carry $25,000… $50,000… even $100,000 deductibles.
Not because they planned for it.
Because it reduced the premium.
Then a claim hits.
And suddenly that deductible isn’t a strategy—
It’s a problem.
One business owner told me:
“We’ll just absorb it if something happens.”
Something did happen.
A property loss.
The deductible alone forced them to delay payroll and tap into reserves they weren’t prepared to use.
The coverage worked.
But the structure didn’t.
A deductible should match your ability to absorb loss without disruption.
Most don’t.
Here’s where it breaks:
• Deductible chosen to lower premium, not based on cash reserves
• No plan for funding the deductible
• Multiple claims in a short period
• Deductibles stacked across policies
Individually, they seem manageable.
Together, they can strain a business fast.
The Real Question
If a claim happened tomorrow…
Could you write the check without it affecting operations?
If the answer isn’t clear, the deductible is wrong.
Inside Protection Circle Insider
Inside Protection Circle Insider, I break down how to structure coverage, so it actually works when it matters:
• How to align deductibles with real cash flow
• Where businesses overexpose themselves without realizing it
• How to balance premium savings with financial stability
• What to adjust before a claim forces the issue
—
Most people don’t think about this until they have to.
👉 Join the Protection Circle Insider
https://www.theprotectioncircle.com/upgrade
(Founder access is currently $29/month)