I recently had the pleasure of being asked by Hustle & Co to contribute to their blog post on common mistakes that freelancers and the self-employed tend to make regarding taxes.  My quotes in their article came from a longer version intended for my blog — and lucky day: you can now read the full version here.

What are common mistakes that freelancers or self-employed people tend to make when preparing for or filing taxes, and how can these mistakes be avoided?

The biggest mistake that self-employed people tend to make when preparing for taxes is that they don’t seek professional help. (I’m not saying this just because I’m a CPA; I’m saying it because I see the results of this mistake regularly.) To clarify, by “professional help”, I’m not suggesting you go to a big tax prep chain and hand in your shoebox of receipts at tax-time; I’m saying that involving an accountant in your business should be one of the first steps a freelancer takes, well before taxes are due. This doesn’t mean you can’t file your own taxes… but if you take the time to consult with an expert first, you’ll make way fewer mistakes when you do. A qualified accountant who specializes in your industry can help you with so many of the key issues that otherwise might come back to haunt you at tax-time:

1) Selection of the right type of entity: sole proprietor, single-member LLC, partnership, multi-member LLC, S-Corp, C-Corp, cooperative, not-for-profit, etc.
2) How to fund your business without tapping into retirement funds and paying a major tax-time penalty.
3) Setting up accounting software and tracking income and expenses properly.
4) Deciding whether to file taxes on the cash basis or accrual basis.
5) Understanding the home office deduction rules.
6) Sorting through the complexities of health insurance: what’s deductible and where; do you qualify for exemptions; how to minimize any penalty for lack of coverage.
7) Explaining the rules for what is deductible, and helping to identify commonly missed deductions such as travel, equipment, cell phone, meals & entertainment, dues & subscriptions, and mileage.
8) Demystifying and debunking what your “uncle’s friend’s lawyer” said you should do to save on your tax bill.

In other words, find an accountant who you feel comfortable with, ask them a million questions, and develop a relationship with them, involving them on your team.

The second-biggest mistake that self-employed people tend to make when preparing for taxes? Looking for an accountant during tax season. By that time, we’re all knee-deep in our existing clients’ needs, and most of us don’t have time to help you convert to QuickBooks or organize your receipts. If you haven’t found someone by tax time, then it might make sense to approach potential accountants with the suggestion that you’d like them to help you file an extension and get organized after tax season is over; you’re more likely to have good luck getting them to work with you.

As for mistakes that I see on a lot of prior-year tax returns that new clients bring me, here are some of the most common:
1) All income is taxable — not just the income that is reported on your 1099-MISC forms.
2) Speaking of 1099-MISC forms… double-check yours the moment they arrive and request corrections immediately. Don’t wait until April.
3) Keep a mileage log or recreate your mileage log from the last tax year based on calendar entries. The IRS does not allow vehicle mileage deductions without one.
4) Speaking of mileage — commuting is not deductible.
5) If you have inventory, count it at 12/31 or as close to it as you can. Even cash-basis taxpayers have to report inventory and cannot include it as a cost of sales.
6) Be careful deducting educational expenses. The IRS will not allow a deduction for education a) to meet minimum requirements of a job, nor b) that qualifies you for a new trade or business. They do, however, allow a deduction for education to “maintain or improve skills”.
7) Gifts to business clients, vendors and the like are only deductible up to $25 per person, per year. (Seriously — it was never indexed for inflation.)
8) Understand the rules of the entity type you chose. (For example, if you’re an S-Corp, pay yourself “reasonable compensation” via payroll; it’s the law.)
9) Depreciable basis on property does not include land. Ever. (If you own your own home and are claiming a home office deduction without using the safe harbor, this means you.)
10) Speaking of depreciation — it’s not optional. You can’t decide not to depreciate something just because you feel it’s too complicated. If the IRS audits you, they will reduce the basis of your property by the amount of the depreciation you should have taken, and you’ll pay gain on the disposal of your property without having had the benefit of the deduction. Sound complicated? (It is. Hire a professional.)