What is not deductible

Three categories cover most of what freelancers wrongly claim: commuting, clothing you could wear anywhere, and space that is not used exclusively for work.

Knowing this list is worth more than knowing the deductible one, because a wrong claim costs interest and attention while a missed deduction only costs money.

Commuting

Travel between home and a regular place of work is personal, not business. That holds however far it is and whoever you are working for.

What is deductible is travel between work locations — from a client site to another client site, or from a qualifying home office to a client.

This is also why the home office matters beyond its own deduction: a qualifying home office makes your home the starting point, which converts trips that would have been commuting.

Clothing you could wear anywhere

The test is not “did I buy it for work”. It is whether the item is suitable for everyday wear.

A suit bought specifically for client meetings is not deductible, because a suit is ordinary clothing. Branded uniforms, protective gear and costumes are, because they are not.

Dry cleaning follows the same rule as the garment.

Space that is not exclusively business

The home office deduction requires regular and exclusive use of the space for business. irs.gov

Exclusive is the word that disqualifies most claims. A desk in the corner of a bedroom is not exclusive use of the bedroom, and the deduction is not proportional to how much of the time it is a desk.

A spare room used only for work qualifies. The same room with a guest bed in it, used twice a year, does not.

The rest of the common list

Claimed	Reality
Your own salary	You cannot pay yourself a deductible wage as a sole proprietor. Draws are not expenses.
Your own health insurance	Deductible, but as an adjustment to income rather than a business expense — it does not reduce self-employment tax.
Life insurance on yourself	Not deductible.
Political and lobbying contributions	Not deductible.
Fines and penalties	Not deductible, including the underpayment interest on your own estimated taxes.
Personal phone line	Only the business share, and only if you can substantiate it. A second line is cleaner.
Meals with no business purpose	Meals require a business purpose and a person present. A solo lunch while working is not deductible.
Client entertainment	Concerts, sporting events and green fees have not been deductible since 2018.
The cost of getting your first client	Startup costs are amortised rather than deducted immediately, above a threshold.
Commuting mileage	See above. It is the single most-claimed non-deduction.

The thing that is actually risky

None of the items above will hurt you much if you claim one by mistake and correct it. What draws attention is a pattern: consistent losses year after year, a vehicle claimed as entirely business use, or a home office equal to half the house.

The IRS is not looking for one wrongly claimed dinner. It is looking for a business that never makes money, which raises the question of whether it is a business at all rather than a hobby with expenses attached.

What to do about the greyer half

Where the personal share is genuinely arguable, the answer is documentation rather than a stricter rule. A mileage log with dates and purposes, a note of who a meal was with and why, a photograph of the room. Not because the IRS will ask — they usually will not — but because reconstructing it two years later is the part that actually costs you.

And for anything with a real personal component — a car used both ways, a trip with a holiday attached — that is a preparer’s conversation. Those are decided on facts, and facts are what you have and I do not.