Self-Employed? How to Keep Track of Your Taxes

Let's face it… filing your taxes when you're self-employed can be a little tricky.

There are several benefits of being your own boss, either as a business owner or a freelance worker. One of these is the flexibility when it comes to your work hours, as well as taking trips, the ability to work from home, and having more control in how much you make.

Another pro to being self-employed is the legal tax advantages afforded to you. Which is what we will discuss today some of these self-employed tax tips:

  • How to file taxes quarterly (and why)
  • Ways to keep organized
  • Tax deductions & benefits

Self-Employed Quarterly Filing

Along with the tax perks of being self-employed, there are some challenges, which include the need to file your taxes promptly to avoid big end of year tax payments. This means that you should file your income taxes quarterly as much as possible.

One of the primary things that you need to remember if you are self-employed is to settle your tax dues quarterly. In this case, you have to take note of when quarterly taxes are due, which are consistent during the 15th of April, June, September, and January. However, these dates may be subjected to change, particularly during unforeseen situations such as a global pandemic, such as COVID.

Rest assured that you will be able to leverage a form from the IRS to find your adjusted gross income and, from there, calculate the tax dues that you owe. Since your income will most likely be inconsistent and vary from time to time, you are protected from penalties by the safe harbor method.

To make sure that you can keep track of your taxes when you are self-employed, you can refer to the two commons but often overlooked tips below.

1. Organize Receipts

One of the primary things that you can do to make sure that you are on top of your tax dues is to organize your receipts. A good practice is to take photos of your receipts so that you will be able to store them digitally. Apart from physical receipts, this includes the receipts that you receive through email.

Make sure that you have a copy of your receipts in a backup storage device such as a cloud server to ensure that you don’t lose any of your copies. As much as possible, organize your receipts by date, too, as well as by type or what you purchased with those receipts. Make sure that you keep your receipts for at least three years because this will serve as your proof and reference in case you are audited.

Tips to keeping receipts organized for tax purposes:

  • I keep an expandable file that has different categories (Travel, Business Meals, Supplies) and each physical receipt goes into a category
  • I print out my credit card statements each month and highlight using different colors (I recommend using one card for all business items)
  • Some tax accounting apps allow you to photograph receipt and store digitally

Leverage a Spreadsheet

Another thing that you can do to keep track of your taxes is to leverage a spreadsheet that will allow you to record your income as well as your expenses properly.

At a single glance, you will be able to know whether your income exceeds your costs or the other way around, as well as the amount of taxes you need to settle based on your generated income. In terms of the latter, you can begin by generating four columns, namely item, cost, date, and receipt. You can even add some notes in another column indicating where your receipts are stored.

When you keep a record of your transactions and receipts, you will find it easier to file for your quarterly taxes. But aside from spreadsheets, you can also explore other contemporary tools that provide more features.

Just remember that as your business grows to scale, or as you employ more people to work with you for your business or freelance works, you may need more assistance when it comes to your taxes.

>> Note: I have freelance writers and virtual assistants help me with my marketing company & Money Life Wax. This means I have to pay them. PayPal invoicing and TransferWise are great for keeping track of writers and payments!

Tax Deductions and Benefits

It can prove to be quite difficult to file your income tax as a self-employed individual if you don’t have a good idea of the tax deductions and benefits that you are eligible for.

In this case, below are some of the receipts that you should keep because these are the expenses that are commonly exempted.

Internet and Phone Bills

Make sure that you keep your internet and phone bill receipts because these are the expenses that are eligible for a tax deduction. However, you need to ensure that you are only deducting business-related expenses. Thus, it is a good idea if you get a separate internet connection for your business, as well as a business phone to ensure that personal internet and phone bills are not included in the expenses that you deduct.

If you don't have a separate account, most of the time talk to a professional, but you can write off a percentage of your internet. For example, 80% of my internet is used for business purposes.

Health Insurance Premiums

Another type of expense that you can deduct from your tax dues is the amount of money that you have paid for your health insurance premiums. However, this is only applicable if you are not covered by the health insurance premium of your spouse. Nevertheless, you can also deduct the amount of money that you have spent to pay for the premiums of your dependents.


Meal expenses are also deductible from your tax dues, provided these are business-related, such as when you travel for a business meeting or when you are entertaining a client. But remember that the meal should not be lavish and that you can only deduct 50% of its overall cost. The normal lunches that you take on a regular day are not included in the expenses that you can deduct under this category.


You can also deduct your travel expenses from your tax dues, but like with meals, you can only do so if your travels are business-related. One criterion that you need to fulfill in this case is that your business travel should at least last longer than an ordinary workday, requiring you to rest in a place away from the general area of your home. You must also have a specific business purpose for the trip and present proof that you indeed engaged in business-related activities.

Some of the deductible expenses when it comes to this category includes your transportation costs, lodging, and meals. This is the reason why you need to be keen on keeping all of your receipts that are in line with these expenses.

The process of income tax filing of self-employed individuals proves to be different from the process that regularly employed individuals have to take. While the former may be more challenging, just adhere to the fact that there are several benefits to being your own boss. All you need is to be committed and diligent in filing your taxes promptly and accurately to avoid any penalties.

Augusta Rule

This isn't something commonly known about, and it depends on how your self-employment business is structured and the nature of your business, but there are tax advantages like the Augusta Rule – tax free rent – that you can leverage.

I share this only because often times, while business ownership isn't easy (90% fail year one), there are interesting tax codes for those who are self-employed. In this case, the Augusta Rule allows homeowners to rent out their home for up to 14 days per year without needing to report the rental income on their individual tax return.

Talk about tax advantages…!

Final word –

Everyone has heard the catchy phrase, “The rich get richer.” By in large this is true, and what most are referencing is what is called the “Matthew Effect” of economics.

With more income comes more opportunity, and with more opportunity comes the ability to create more income (in most cases). This is why the self-employed route is so lucrative when done correctly and so appealing.

The legal tax advantages of self-employment are simply not available if you work a standard 9-5. While tax advantages or legal tax write-offs have to be centered around the self-employed taxes you're filling for, the fact of that matter is there is simply more you can do.

That being said – you need to be organized, diligent, and thorough. Not to mention, like any tax advice this is not a guide nor a how-to. Simply put, these are just some of the tax ideas to consider before filing self-employed taxes.

When it comes to anything on the internet or tax advice for that matter, always consult with a professional in that industry!