The contractor insurance mistakes I keep seeing.

Buying policies instead of coverage

This is the one I know from the inside. Before insurance was my job, my own business got sued — by a job applicant I never hired — and I'd bought every policy my agent recommended. The one I needed wasn't in the stack. A list of policy names on a proposal is not protection; what's inside them is. The question isn't “do I have general liability?” — it's “what happens to my business in the five worst scenarios I can name, and which policy answers each one?”

Stopping at the contract minimums

The limits a GC, a landlord, or a bank requires are what protects them, not what protects you. Meeting the requirement gets you on the job site; it says nothing about whether a real claim would sink you. Set your limits off your downside, not off somebody else's paperwork.

1099-ing the crew because everyone does

The label isn't yours to pick — who controls the work decides, and if a “1099 guy” gets hurt and turns out to be an employee, you're personally on the hook. This one's expensive enough that it has its own guide.

Paying a sub before their certificate shows up

At audit, payments to subs with no certificate on file get charged as your payroll, at your rates, with your mod. No certificate, no check — make it a rule before your first job, because it's much harder to start later.

Shopping the cheapest number

Two policies with the same price can be worlds apart in the exclusions — that's where cheap policies hide their cheapness. And compare the all-in total cost, never the premium line alone; on plenty of contractor policies the fees are real money.

Running the books yourself until an audit forces the issue

A bookkeeper who tracks payroll by class of work, collects sub certificates, and keeps job costs clean pays for themselves at audit time — and I say that as the guy selling the insurance, not the bookkeeping. It's step one in the new-contractor guide for a reason.

Letting a policy lapse

Your insurance history follows you — lapses, cancellations for non-pay, gaps — and companies price what they see. A payment problem is a text-me-today problem; a lapse discovered at renewal is a pay-more-for-years problem.

Never re-reading anything as the business changes

New trucks, a new trade, bigger jobs, your first employee, work across the state line — every one of those changes what your insurance needs to say, and none of them update it automatically. Once a year, or at any big change: a review. Mine are free and I do the reading.

Scattering policies across agents

Work comp here, the auto somewhere else, the shop policy wherever the landlord's guy was — nobody sees the whole stack, so gaps hide between agents and nobody's accountable for the seams. One person reading everything is how the seams get found.