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For freelancers and anyone with 1099 income, you will need to keep track of your business-related mileage. For 2019 tax filings due in 2020, you can claim a 58-cent deduction per business mile driven. The self-employed can deduct the cost of your healthcare on your taxes. You cannot deduct any expenses that relate to the operation of your vehicle (gas, maintenance, etc.), but you still can deduct parking and toll expenses. You can also deduct your commute to and from your office.