If you're self-employed for the first time in your life, it would be very easy to forget to store receipts for 1099 deductible business expenses until tax time rolls around.
The IRS, however, will not be so forgiving. They expect that at the end of each tax year you will be adequately prepared with a full set of tax records. Worse, if you're used to a traditional job and getting a tax return at the end of the season, you might be in for a nasty surprise when you're stuck with a hefty tax bill instead. Invest in a tax receipt organizer or you had better hope you have a financial backup plan.
Why is it so important to have a tax document filing system?
Before we can answer that, we first have to address a common myth. It's a well-established and erroneous idea that the concept of business receipt organization is best visualized in a madhouse of paper clutter. Whole reams of paper receipt stubs held together with staples.
Having to categorize different types of receipts among various dividers and stuff them all into a comically oversized accordion file folder. If you subscribe to this myth, I bet video footage of your home office will resemble a DIY episode of Hoarders (all in the name of record-keeping for tax purposes!).
This is a picture you won't forget. It is also complete and utter nonsense, peddled by those who want you to overpay on taxes year after year. This is the story told to you by those who would have you take the standard deduction, then sit back and eat the losses. I'm banging on about this for so long because it is extremely important. For any serious professional in the modern-day, the standard deduction is a pitiful amount of money.
Unless you want to lose thousands - if not tens of thousands - of dollars in unnecessary tax bills, you must always be organizing receipts. But all this bookkeeping sounds like an awful lot of work, doesn't it?
Introducing Keeper: The receipt organizer for freelancers and small business owners
Thankfully, taking care of your taxes in the modern-day as a self-employed worker doesn't have to be a huge hassle. In reality, with the right technology, very much of it is just about automatic. This is where Keeper comes in.
Keeper is a mobile app that can be installed on your android or iOS mobile device. It connects to your financial institutions and acts as a receipt scanner. It scans your credit card and bank statements for digital receipts, then asks you whether your purchases were made for business purposes. All you have to do is reply to texts, and it will ensure that you get an appropriate reimbursement for your business expenses at tax time.
Gone are the days of being forced to keep physical copies of any printable receipts. No longer must you keep a constantly-updated excel spreadsheet of your expenses to tell the business purchases from the rest. These are the days when you can declutter in pieces. Free yourself from the tyranny of keeping paper receipts for taxes.
The Keeper advantage
Now you know what Keeper does, but why is it so special? What sets it apart from other software such as Quickbooks? For a start, it pairs you with a real person: a tax assistant who will go over the records of your purchases and make suggestions of potential tax write-offs that you would otherwise never have thought of. It doesn't matter if you are filing Postmates 1099 taxes or Lyft. You can benefit from this app.
These might include all kinds of things.
- An office chair that you ordered on Amazon to replace an old one that outlived its warranty
- Gas for a car that you use to travel for work
- Food if you're having a meeting with a client to discuss business over dinner
- Rent or property tax if you work from a home office
- A charger cable for a gadget you need for your business
- Your Wi-Fi bill if you operate your business online
- A replacement for the burnt-out hard drive on your office computer
And many, many more. In this way, it allows the tax illiterate to benefit from write-offs that they could not have possibly known about without such specialized education. Not to mention, they have a ton of free tools like their self-employment tax calculator to help make planning your 1099 taxes a breeze.
What if I still make some purchases with cash?
No problem! While electronic payments are still easier to track if you've got a cash purchase that might be tax-deductible the process to track it is simple. Just take a picture of the receipt and text it to your tax assistant, and they'll do the rest.
But there must be some risks, right?
You would think so, but Keeper is very generous in keeping you covered. For a start, the connections to your financial institutions are made through Plaid, a Visa service that transmits only the transaction data and does not put your sensitive credentials at risk.
In addition, it features a free trial. You can try out the service and its features for two whole weeks and see if it's for you. You will of course need to provide a viable payment method to qualify for the free trial, but you can cancel any time. Equally important over time is that it costs less on a month-to-month basis than other receipt apps on the market, saving you yet more precious money.
How do I get all this setup
Thankfully, both setting up your initial 1099 expense tracking and filing your actual taxes (more on the latter in a bit) are handled through simple questionnaires specifically designed to be easier for those of us without a background in tax law to understand.
Answering questions about every purchase still sounds like a grind
Don't worry! Keeper will maintain a backlog of your responses, and over time it will learn your preferences. As it becomes clear that certain types of purchases are consistently either personal or business-related, some transactions will be categorized automatically and you will have to answer questions less and less often over time.
Filing taxes with Keeper
Now you know everything there is to know about Keeper's lightweight yet robust offerings on the front of day-to-day expense tracking. But what does it have to offer when it comes time to actually file your taxes?
The simplest solution is to file through Keeper itself. For a reasonable fee, you can do your taxes all in the same place where your expenses have been tracked - saving you time and mental energy compared to hunting down another tax filing method. Even if you're late to the party, it can go back through your statements from earlier in the year and quickly put together reports on expenses that may be deducted.
What if I want to file my taxes elsewhere?
If you already have a preferred method of filing your taxes, you can still benefit from Keeper. For an even smaller fee than filing with Keeper, you can export your records - neatly organized and all - in the form of just one document.
In so doing, you will get all the advantages of having tracked your expenses with Keeper: all of the categorized expenses, all of the business deductions you would otherwise have overlooked. This document can then be used to easily file your taxes by whatever other method you like.
The lesser-known benefits of Keeper
Now you know about the advantages you will have as an avid user of Keeper, but what if there was even more? You'll be pleased to know that the team behind Keeper has your success in mind well beyond the scope of your direct interaction with the app. They are constantly researching and creating new tools and content to make sure you get the absolute most out of your career as an independent contractor.
Some of this content includes, but is not limited to:
- Specialized guides for potential business deductions in many different freelancing industries
- Free calculators to help you estimate your tax burden in a number of ways ahead of time
- Simplified tax education to help freelancers and small business owners understand taxes
- A variety of articles aimed at helping you learn more about your taxes and the gig economy
- Tools, tips, and other tidbits to maximize your freelancing experience
And much more, all free of charge whether you use the Keeper app or not!
Hopefully, this will have provided you with all the information you need to make an informed decision about whether Keeper is right for you. If not, check out all of these other Keeper reviews. The Keeper team works day in and day out to do everything they can to make sure we have the best tax app around for independent contractors. This is an ever-shifting goal-post, and their efforts are always bearing new fruit. Do you still have more questions? Feel free to check the Free Resources for more details.
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At Keeper, we’re on a mission to help people overcome the complexity of taxes. We’ve provided this information for educational purposes, and it does not constitute tax, legal, or accounting advice. If you would like a tax expert to clarify it for you, feel free to sign up for Keeper. You may also email firstname.lastname@example.org with your questions.