If you're in need of extra business deductions before the end of the year, one method is to prepay some of your business expenses for future years, such as business insurance, rent on offices and equipment, and lease payments on business vehicles. However, there are some tricky rules you need to be aware of to deduct such payments this year.
The general rule is that you can't prepay business expenses for a future year and deduct them from the current year's taxes. An expense you pay in advance can be deducted only in the year to which it applies. For example, if you pay a two-year lease in advance, you could only deduct the portion of the lease payment that applies to the current year.
However, there's an important exception called the 12-month rule. It lets you deduct a prepaid future expense in the current year if the expense is for a right or benefit that extends no longer than the earlier of:
You may use 12-month rule for business insurance premiums; business licenses, rents and leases; and payments to terminate business contracts. However, you may not use it for payments for interest, loans, and other financial interests; or purchases of furniture, equipment, and other long-term capital assets.
Example: You're a calendar-year taxpayer and you pay $1,000 per month in rent for your business office. On Monday, December 31, 2019, you mail a rent check to your landlord for $12,000 to cover all of your 2020 rent. Your landlord does not receive the payment in the mail until Wednesday, January 2, 2020. The 12-month rule applies. The benefit you've paid for — a business office — does not extend more than 12 months beyond January 1, 2020. Therefore, the full $12,000 is deductible in 2019. Also, your landlord need not pay tax on the $12,000 until 2020 since he didn't get the rent check until 2020.
Before you prepay expenses in this way let the payee — whether your landlord or other person or company — know what you're doing. Otherwise, they might not deposit your payment thinking it was sent by mistake. Most landlords and others are more than happy to accept payments in advance.
Also, make sure you can prove to the IRS when you sent the advance payment. Use U.S. Postal Service priority mail with tracking, or certified or registered mail. This way, you have proof of the date you mailed the check and proof when the payee received it.
Of course, whether prepaying expenses makes sense depends on your tax rate this year and in future years, as well as future changes in tax laws that might raise your taxes. If you expect your income to go up substantially next year, you could be better off not prepaying expenses and instead maximize your deductions for next year.
To learn more about making the most of your business deductions, see Nolo's Deduct It! by Stephen Fishman, J.D.