Half of first-year business owners say their biggest regret is not understanding what insurance they needed, according to an ERGO NEXT survey of 501 owners reported by Stacker on September 30, 2026. The finding points to a gap that hits solo operators especially hard, since they carry every risk themselves.
For freelancers and one-person shops, insurance is easy to postpone while you chase clients. The survey suggests that delay is one of the most common things new owners wish they could undo.
What The Survey Actually Found
Not understanding insurance topped the list at 50% of new owners. Another 40% wish they had built stronger financial reserves, and 35% regret not seeking expert advice sooner.
Smaller shares pointed to process and timing. About 29% wish they had set up formal risk management, and 20% said they would have bought more coverage or bought it sooner.
Nearly one in five first-year owners, or 18%, skipped insurance entirely and put their attention on marketing and refining their product. Among the 82% who did have coverage, 14% said they were unsure which risks their policies covered.
Why This Matters For Self-Employed Owners
When you work for yourself, there is no employer policy standing behind you. A client dispute, a damaged piece of equipment, or an injury that keeps you from working can land directly on your personal finances.
The uncertainty figure is the quiet warning in this data. Owning a policy is not the same as knowing what it pays for, and a gap between the two can surface at the worst possible moment, such as when you file a claim.
The reserves finding belongs in the same conversation. Savings and insurance work together, because a cash cushion covers the deductible and the weeks when income stalls.
What Self-Employed Owners Should Do Next
Start by listing the risks in your own business, such as professional errors, property damage, cyber incidents, and lost income. Then read your current policies, or request quotes, with that list beside you so you can see what is covered and what is not.
Ask an independent adviser or broker to walk through any exclusions in plain language. If you have been skipping coverage because of cost, compare a few basic options and ask about bundled policies before deciding you cannot afford any protection.
Finally, set a target for cash reserves, even a modest one, and add a small automatic transfer each month.
What To Watch Next
Surveys like this one come from an insurer, so read the results as a signal rather than proof, and look for similar research from independent groups. Insurers and brokers are likely to push more education and simpler products aimed at first-time owners.
Our guide to new freelance business insurance options is a useful starting point if you are comparing coverage. Watch also for changes in health coverage costs, since those can strain the same reserves the survey says owners wish they had.
