Deductions
“I pay for my own expensive health insurance as a sole proprietor, where exactly does the self-employed health insurance deduction go on my return?”
For a sole proprietor paying personal health insurance premiums, the reporting location often depends on how the business return is filed and how the premium arrangement is documented. In many cases, the deduction is reflected on the individual return rather than directly on the business schedule, with the treatment shaped by the ownership structure, whether the policy is in the taxpayer’s name, and whether there was enough self-employment income to support the deduction. The return can also be affected by any premium amounts already handled through another tax-favored arrangement, so the exact placement is usually tied to the full filing picture. A targeted review with a CPA can turn the uncertainty into a clear next step.
In your 30-minute session, the KGOB advisor handling it will:
- Read your exact situation and tell you, in plain English, what’s actually going on.
- Lay out your options and the trade-offs — no jargon, no judgment.
- Give you a clear next step you can act on, whether that’s with us or on your own.
“I incurred massive personal credit card debt to fund my struggling business, is the crippling interest I pay on those cards tax deductible?”
“I use my personal cell phone extensively for my freelance work, what exact percentage of my monthly phone bill is safe to write off?”
“I run a failing e-commerce business and have obsolete inventory sitting in my garage, can I completely write off the cost of unsold goods?”
“I bought a new high-end laptop exclusively for my side hustle, what specific receipts or logs do I need to keep to prove this to an IRS auditor?”
This page is a prompt to start a conversation, not tax or legal advice, and states no tax-law specifics as fact. A consult session does not by itself create an ongoing engagement. We do not promise specific outcomes or savings. Kohari Gonzalez Oneyear & Brown PLLC — Charlotte, NC.
Back to the full library