Less Than a Month Left to File Your Taxes: An Attack Plan

You may be down to the wire, but follow our attack plan to finish your taxes on time and you’ll be finished faster than you can say, “Uncle Sam!”

Taxes are due April 15 — less than a month away. What’s that, you say? You haven’t even….um….started?

Take a deep breath. Everything is going to be ok. At least you didn’t wait until 11:53pm on the 15th, right? As I’m writing this article, you have 28 days, 672 hours, 40,320 minutes, or 24,19,200 seconds to finish your taxes. That’s puh-lenty of time!

You may be down to the wire, but follow our small business tax attack plan and ensure your taxes are finished faster than you can say “Uncle Sam!”

1. Create a schedule

Okay, you only have a few weeks to finish your taxes. But you still have a life to live and a business to run. You’re not going to spend 24/7 on your taxes, so how much time will you have to spend?

Create a schedule for the next month and stick to it. You might only need to spend 15 minutes a day to finish on time, or you might need to spend 2 hours per day. Take stock of what’s in store for you, tax-wise, and commit to spending the appropriate amount of time each day getting the job done.

Keep in mind that you’ll stay motivated if you schedule frequent, short intervals as opposed to setting aside an entire weekend for a tax marathon!

2. Get everything online

First thing’s first: get everything in one place.  That may mean collecting hard copy stacks of bank statements and receipts from the glove compartment of your car, and piling them in front of your scanner or stuffing them in a Magic Envelope.

It may just mean making sure that all digital documents have been sent to your Shoeboxed account.

No matter what stage of the game you’re in, the goal should be to get all tax documents – paper or digital – into a single location where they’re easy to view, edit and organize.

Scan hard copies, snap photos of receipts using the Shoeboxed Receipt and Mileage Tracker, and get everything where you can see it.

3. Catch up on categories

Every receipt and document needs to be labeled with a category. This will create an accurate picture of your small business write-offs as well as your income.

Go through your Shoeboxed account and search for any receipts or documents that are marked “uncategorized.” Assign them an appropriate category to make sure you haven’t missed any important deductions, then move on to step 4.

4. Create reports

As a small business owner, you have a lot of different tax areas to consider, including write-offs, your employee salaries, 1099s, your business revenue and all sorts of other financial details that need to be accounted for.

Use Shoeboxed to generate easy reports in the format of your choice that you can share with your tax professional. The PDF report will include a table of expenses with date, total, payment type and category information, along with the digital images of your receipts.

These reports can then be emailed to your tax professional instead of sending him or her envelopes packed with paper receipts (and besides, you don’t have time to mail stuff – we’re down to the wire here!).

5. Check for extras

Did you track expenses anywhere else besides your Shoeboxed account? You might have saved certain emails, created reminder lists for yourself, or have a desktop folder labeled “taxes” that needs to be sorted. Check these additional sources and see if there is anything not accounted for on your report.

You can also download a copy of your bank statements from each month of the year, and go through each one line by line. Seeing your bank statements will remind you of expenses you may have forgotten about, as will reviewing credit card statements and emailed receipts.

6. Submit your report

Submit your completed reports to your tax professional, and be sure to respond to all subsequent emails promptly. Your only job now is to answer any questions that may arise, and provide receipts if necessary. Remember that you can easily search for individual receipts in your Shoeboxed account to find the exact receipt you need.

Sha-zam! Your taxes are as good as done. Now go have a latte or take a nap.

What’s your insider secret for finishing taxes fast?

Tax Filing 101: Choosing the Right Filing Method

While there is no “one size fits all” solution when it comes to tax filing, being equipped with an arsenal of facts may steer you in the right direction. Check out this helpful guide from our friends at Bench to get started.

This guest post is brought to you by Bench, the online accountants that use your Shoeboxed receipts to build you tax-ready financial statements.

Tax season is fast approaching and many small business owners are facing the same dilemma – what’s the best way to file taxes? While there is no “one size fits all” solution, being equipped with an arsenal of facts may steer you in the right direction.

Option One: DIY

This is ostensibly the cheap and dirty method, but what does filing on your own really cost?

Cost (Not Including Bookkeeping)

Assuming that you pay yourself a wage of $20.00/hour, the cost of filing business taxes on your own adds up very quickly. Based on IRS estimates of time spent filing tax returns, these are the prices you’re actually paying to file yourself:

Form 1040, Schedule C (sole proprietors):  $200.00 1
Form 1065 (partnerships): $640.00 2
Form 1120/1120S (corporations): $1,540 3


One of the most important aspects of filing taxes is accuracy – both to ensure that you get the maximum available refund and to avoid the steep penalties charged for filing errors. To put this into sharp perspective, it is estimated that Americans miss $1 billion in available deductions by attempting to file taxes unassisted – that’s $460.00 per person!4 In addition to that, in the event of an error with your tax return, you will be personally liable for any associated penalties and interest charged. Oh, and just because they can, the IRS accrues interest on outstanding payments and penalties daily.


The IRS website? Google? Filing taxes unassisted is just that – unassisted. And if you happen to get audited, you will also have to represent yourself in front of the IRS or pay for professional representation.

Option Two: Invest in Software

As with almost everything else in life, filing taxes is moving into the online realm, with nearly 30% of Americans choosing this method.

Cost (Not Including Bookkeeping)

Like filing unassisted, the real cost to calculate when considering this option is the time you spend using the software, which will vary considerably depending on your familiarity with the program and the complexity of your tax return. The following prices are for TurboTax Federal & State filing, plus a conservative estimate of your time invested.

Form 1040, Schedule C (sole proprietors): $150.00 – $190.00
Form 1065 (partnerships): $300.00 – $500.00
Form 1120/1120S (corporations): $490.00 – $720.00


All tax filing software comes with a “maximum refund guarantee,” which entitles you to a refund on the price of the software if you can get a larger refund using another filing method. Just keep in mind that you would have to actually file your taxes by another method to claim this refund – and absorb the additional cost of doing so.  In the event that you are slapped with any filing penalties, you will be reimbursed only if the offending error was caused by a software miscalculation – not a user error.


All software programs have built in support features like live chat and telephone assistance – though you will likely speak to a different person with every issue.

Option Three: Use a Retail Tax Service

If software just isn’t cutting it, but you’re not ready to invest the time and money to find a qualified CPA, you may consider a walk-in service.

Cost (Not Including Bookkeeping)

Retail tax preparers, like H&R Block and Liberty Tax Service, generally charge per form. While the best way to know for sure is to receive a quote, the following are the average prices you’re looking at:

Form 1040, Schedule C (sole proprietors): $200.00 – $250.00
Form 1065 (partnerships): $500.00 – $700.00
Form 1120/1120S (corporations): $750.00 – $850.00


Retail tax preparers are backed by a guarantee policy that covers you for both penalties and missed deductions; however, as with the software guarantee, you would have to catch the missed deduction in order to claim the refund. One other important thing to note about accuracy is that registered tax preparers are not required to have any education in taxation and do not have to pass any competency exams – though the IRS is attempting to change this.


Your tax preparer will be able to answer questions throughout the process of filing your return, but year-round support is limited as the retail tax industry is extremely seasonal and the vast majority of employees are only employed from January – April. In the event of an audit, tax preparers are not licensed to represent you in front of the IRS.

Option Four: Call in the Pros

This option will cost you the most up-front, but it will also save you the most in the long run – much like paying for regular car maintenance to preserve the life of your vehicle.


Most CPAs and EAs charge by the hour, so the easiest way to reduce your tax bill is to ensure that your books are well maintained and that you have all the required documentation ahead of time. The following are the average price ranges for professional tax preparation, though price varies considerably by situation, location, and experience.

Form 1040, Schedule C (sole proprietors): $250.00 – $500.00
Form 1065 (partnerships): $500.00 – $1,000.00
Form 1120/1120S (corporations): $1,000 – $2,500.00


Both CPAs and EAs have significant education and experience in taxation. In addition, they’re required to undertake continuing education to stay up to date on changes to tax law. Not only will a CPA or EA get you the maximum available refund when your taxes are due, they will also work with you to create a customized business plan that minimizes your tax bill over time.


Personalized year-round support is the greatest benefit of using a qualified CPA or EA. While other tax preparation options may be able to provide a comparable tax refund in April, only a CPA or EA can advise you on how to significantly reduce your tax bill over time through calculated tax planning and business structuring. Finally, in the event of an audit, both CPAs and EAs have unlimited ability to represent clients in front of the IRS.

Bottom Line?

There are a whole host of factors to consider when choosing a method to file taxes, so you really have to take the time to find the option that works best for you.

If there is one thing that holds true for any method, it’s that good bookkeeping and solid preparation are the easiest ways to reduce both time and expense in April (or March for corporate returns)!

To get a head start this year, learn “How to File Your Taxes in 5 Minutes per Day!

This post is brought to you by Bench. Bench is the modern bookkeeping service that provides audit-proof financial statements from online accountants at an affordable fixed price. Not in the software business or the accounting business, Bench is in the business of solving accounting problems and letting clients spend more time doing what they love.