Bracketology and Taxology: Why Filing an Extension May Be Your Best Tax Strategy as a Small Business Owner

 Mark J. Kohler for paysimple.com writes: Finding your best tax strategy can seem as complex as picking a winning NCAA bracket. In fact, ESPN experts and their “bracketology” oftentimes claim that the unconventional wisdom can be the secret to success and saving your precious $5 entry fee into your office pool.

But what about your tax strategy this March and saving thousands on your tax return? What’s your “Taxology” for super savings?

Now let’s be honest. We all know that tax planning takes place in November and December.

So instead of me writing an article on a bunch of last minute pseudo tax tips that are simply a feeble attempt at making us feel better for putting off what we should have done last year, let’s call a spade a spade.

You know what I’m talking about: filing an extension

Now here’s why I think filing an extension could be your sleeper ‘Taxology’ strategy to winning on your tax return.

First, by filing an extension, it’s equivalent to taking a timeout right before the final shot of a game. It gives you a chance to dig up all the expenses you can and reevaluate how aggressive you want to be on your tax return. 

I’m not suggesting being too aggressive and “taking a bad shot” or risking an audit, but giving yourself the chance to uncover real write-offs you’re probably missing out on.  Let’s face it, many CPAs and taxpayers are far too conservative and leave legitimate tax deductions you are entitled to on the table and cost you thousands.

Second, filing an extension is as easy as raising your hands in a game and waving to the referee. By filing the extension, you buy time until October 15^th to send in your final tax return. In order to make it happen, you simply file Form 4868 electronically or mail it in.  (However, keep in mind, it’s important you estimate how much you think you might owe in tax and send it in with your extension. You can always get a refund later and it will prevent any penalties or interest). Download the form here.

Third, don’t be afraid to file an extension. Millions of American file extensions every year and there is nothing wrong with it. In fact, various statistics over the years have shown that you actually reduce your chances of an audit by extending; simply because the IRS is assigning their audit teams to the already filed returns.  Now maybe this is an urban legend, but hey, if there’s any truth to it all…why not? 

Finally, let me give you the “why” and get your juices flowing. Just as in a basketball game with seconds to go, let’s pull out a clip board and think of all the different strategies or write-offs we could be missing if we rush into filing. Here’s just a few to consider:

Travel-related expenses. In my opinion, this is one of the most underutilized tax deductions by small business owners today. Unlike meals and entertainment that are limited by 50%, travel expenses are 100% deductible. These include airfare, hotel, rental cars, valet, taxi, trains, tolls, etc…  Consider all of your travels last year that may have involved a meeting with a client, a vendor,  or a training meeting, a tour of a competitor’s facility or store, your annual board of directors, shareholder, manager or member meeting, a conference retreat with a partner (the list goes on and on).

Auto Deductions. Remember this isn’t travel, but expenses for your car or truck used in your business. There are two main options: mileage or actual expenses. Statistics show that 90% of small business owners actually utilize the mileage method. For 2012, this was 55.5 cents per mile. Surprisingly, again I see many taxpayers shy away from claiming their true mileage because they are afraid of an audit. True, you should do your best to keep a written record, but if you haven’t been extremely detailed, still utilize an estimate and take the deduction. 

 Dining and Entertainment. Again, a highly underutilized expense by small business owners and should be a healthy line item on your tax return.  Please make sure you consider all of your meals last year where you discussed business with a partner, or a potential client, vendor or strategic alliance.

Office Supplies and Technology. Every small business owner is regularly buying supplies and upgrading their phone, computers, and digital reading devices. Don’t forget that when you have a small business, the majority of these items can be fully expensed. 

Technology and Telephone. Many don’t know that recent case law and IRS rulings allow business owners to write-off 100% of their cell phone expenses, so long as they have at least one dedicated home phone line. Moreover, make sure to include the cell phones of your family members that work in the business alongside you and need a cell phone for their legitimate role in the business.

If you have to, consider a SEP contribution before filing. I say this in a negative way, because a 401k is FAR better for the small business owner and the SEP should really only be considered if you failed to implement the 401k back in December. However, by filing an extension you ‘buy time’ to consider a contribution and then make the contribution. The contribution amount is 25% of your net income or up to $50,000, whichever is less. 

Bottom line: be confident if and when you file an extension. Take that ‘hail mary’ shot from half-court! If you have a reasonable argument for taking a deduction and miss, the worse the IRS will do is disallow it. Take the time to dig up those expenses on credit card statements, bank statements, receipts, or anything you can find. Don’t shy away from throwing them on your return.