The Last-minute Tax Extension Decision: Stop Worrying & Talk to a Tax Expert


As the April 15th tax filing deadline rapidly approaches, for most small business owners  who haven’t filed there are two options:  either finish your tax return, or consider an extension.

Small business owners and freelancers should consider speaking to a tax preparer regarding their situation to decide if there’s enough time to make a last-minute dash to submit your return.  Otherwise, the preparer will be able to file an extension, which will give the taxpayer an additional six months of breathing room.

But there’s a catch:  this only applies to the paperwork, and you are still responsible for estimating and submitting payment for your taxes. If the IRS considers your payment estimate to be incorrect, it’s possible that the IRS will assess a late penalty.  The IRS charges an interest of 0.5%/month on any portion of your taxes not paid by April 15th.

According to, an online tax preparation website, most of their customers requiring an extension often complain about not being organized enough to submit their small business returns—generally overwhelmed by the amount of tax paperwork that needs to be found and organized before meeting with an accountant.

In order to get everything squared away properly, Teaspiller recommends sites like Shoeboxed to help organize business receipts.  This makes it easier once tax season approaches for the customer, and also makes it easy to automatically upload all of the information directly into Teaspiller and share with your selected tax preparer.

Teaspiller’s certified experts (CPAs and IRS Enrolled Agents) can then help a Shoeboxed customer decide if an extension is needed, and whether or not you need to make a payment to the IRS–helping small business owners get the reassurance they need before making an extension decision.

Author: Sonny Byrd

Sonny is a former rock star who has served as Shoeboxed's Head of Marketing since 2009. After touring the US with his band of 3 years, he left the spotlight to focus on building Shoeboxed's marketing channels and growing the big blue Shoeboxed brand. He loves to write, cook, produce beats and electronic music, and most of all, to introduce unorganized independent business folks to Shoeboxed, the easiest and most cost effective organizational business tool in the world.