14 min read
Being a freelancer is challenging. By the time you figure out how to market yourself, secure clients, accept payments, pay contractors, and deliver work, you’ve done a year’s worth of work for five people! Then there’s another thing you have to do: your taxes.
There’s a lot of fear that circulates around taxes. Between the filing and the actual paying of your taxes, you might lose a bit of sleep while you make sure you’ve kept track of all your deductions, gathered all your 1099’s or K-1’s, and hit that deadline.
Let’s get rid of that anxiety you’ve been holding on to around bookkeeping and taxes. After reading this article, you’ll be in solid shape for your tax prep and staying on top of your monthly financials.
These steps I’m about to share with you are the basics for sole-proprietors or single-member LLC owners and will give you the best practices to understand and navigate tax time whether you do them yourself or hire a professional.
You’ll find this particularly helpful if you’re already paperless and web-friendly, which is probably a safe bet considering you’re on the ConvertKit blog. Let’s dive in.
You started a few side projects and now you're starting to accumulate real income and the expenses associated with these gigs. In the beginning, opening a separate “business” bank account seemed like a joke and a tedious task, but now it's time to do your taxes and you have no idea how much you made or spent. The best way to avoid this is to open a separate bank account from the beginning.
Assuming you didn't do that, the best way to get up to date is to open a separate business account today. This account will be where you deposit all your checks—or connect to your Stripe account—and will be the credit/debit card you attach to all your subscription software services and even pay for business lunches with.
Going further, if you open a separate savings account to deposit your estimated income tax (Step Three: Quarterly Taxes) you anticipate owing as you go along, you won't have to worry about keeping a certain balance in that main operating account.
Do you sell taxable goods or services? You'll need to collect and remit sales taxes. Having a separate savings account to deposit all the sales tax collected is a great way to avoid spending money that's not yours. The amount shown on your “sales tax payable” ledger in your bookkeeping will match what's in this account. Having this setup means you won’t worry about spending that money accidentally out of your operating checking account.
If you prefer to pay for things with credit (yay air miles!), then make sure you set aside one card for business only. Keeping these transactions separate will save you time at year end, and likely save you money if you pay someone else to file your taxes.
Action Item: Open a separate checking account for your business today.
If you're taking your freelancing seriously and considering going full time (if you’re not already), you'll want to know where you're making and spending money. This enables you to get a view into where to focus your time and attention for the most profit. This doesn't mean you have to quit doing your favorite gigs, but it may mean you need to have a conversation with your clients about your rate. For example, perhaps project-based billing rather than hourly would help?
Generally, you have two options when it comes to bookkeeping– DIY or hire out.
As you expected, hiring will almost always cost you more per month than doing it yourself, but consider some additional costs other than your cash per month. How much is your time worth and how long will it take you to do your bookkeeping? Are you competent or willing to become competent at bookkeeping?
Every freelancer makes their own choices about where to engage a pro and this is no different. If you'd like to do your own bookkeeping, a Google doc can actually be great. If your needs are bigger, you may consider Freshbooks if you also need invoicing or Xero if you need more robust reporting.
Do you just need a basic income statement and balance sheet? Or do you need invoicing, bill pay, and financial planning? The range is vast and making sure you know what you need before making a purchasing decision is crucial because the cost of a simple system can be less than half of a full-service one.
Bench.co or a trusted referral are great options to get your books done for you. Remember, just because someone is doing your books, doesn't mean you don't need to provide input or spend time working with your bookkeeper!
Action Item: Set up a bookkeeping system.
Our income tax system is a “pay-as-you-go” system. When you are an employee, these taxes are collected and remitted for you. When you’re self-employed, this is up to you. Be proactive and avoid having to go into payment plans with the IRS. It’s difficult to dig yourself out of a hole like that and continue making current estimated tax payments.
Avoid tax prep time surprises, especially if it's your first year or the first year making a significant amount of income by staying current with your quarterly state and federal income tax payments.
A general estimate is to save about 30% of your net income (revenue less expenses) for income tax (remember that savings account you opened in lesson 1? This is where it comes in handy). This will vary widely depending on:
You can use your vouchers from your prior year return if you were self-employed last year. Remember, owner draws are not an expense as a sole proprietor.
You can pay your federal “Estimated Tax” online or send in a check with a voucher from your prior year return. Your state probably has an online payment system as well. These usually cost an extra 2.5%. If you have vouchers from your prior year return, the instructions are listed there. Alternatively, you can simply google “How do I pay my income taxes for (your state)”.
You may be subject to additional quarterly or annual taxes on top of income tax. These could include a gross receipts tax, sales tax, or an LLC “pleasure of doing business” tax. If you want to find out more about your state, research “(Your state) Department of Revenue” or give us a call.
Action Item: Set up calendar appointments or reminders for your quarterly tax payments.
Generally speaking, the IRS allows business deductions that are ordinary and necessary. This is why it’s difficult to list an exhaustive list of deductions for all self-employed people. It’s important to note that deductions generally come down to a facts and circumstances judgement.
Some expenses may be ordinary and necessary for one business, but completely illegitimate for another. An ice cream maker will be able to deduct sugar and cream, but this is unlikely for a marketing consultant. This is why it’s good to get the advice of an experienced tax professional. Don’t defer to tax software to make this decision.
Approach deductions with caution– just because you can, doesn’t mean you should. The better your records, the better your chances of maintaining a deduction under audit. As a self-employed person, your situation is grayer than a separate corporation.
You are an individual and a business. It’s easy to slip into thinking that your regular personal expense are deductible. There are many personal deductions allowed, but we’re going to focus on your business expenses only here.
Also, it’s important to note that your net income according to your books won’t likely match that of your income tax return. There are some items you can choose to pay for out of your business, but the IRS will treat them differently. Generally, they allow fewer deductions, with few exceptions.
There are many misconceptions about what’s ordinary and necessary as a deduction. The key is to remember that the deduction is supposed to be ordinary and necessary for your business. That means a new shirt, lunch, or coffee may be personally necessary, but not deductible for your business.
The most common illegitimate expenses we see are:
You are entitled to legitimate business deductions. Make sure you know the difference, or hire a professional who can help.
Action Item: Save your business meal, entertainment, and travel receipts and document who you were with and what the business purpose was.
Now, let’s talk about mileage for auto deductions.
Do you drive to projects or sites for gigs? Maybe you use your vehicle for business “most of the time”. Are you entitled to a deduction? The short answer is yes.
To qualify for the standard mileage deduction or actual expenses, you need to track all your miles on each vehicle you use. That means your tax accountant, or software, will ask you how many total and business miles you traveled in your car.
If you have a full listing of expenses related to operating your car, you can then take that business/total ratio and multiply by the expenses. Then, you take the most beneficial deduction. There are some additional specific rules about which method you can use.
Remember, commuting is not considered business mileage. Most people don't track their miles. Don't be most people. If you're audited, this will almost surely come back to bite you. Depreciation and purchasing a vehicle is beyond the scope of this guide. The main takeaway is to track your miles. Consider using MileIQ or Expensify's mileage tracking feature, or perhaps you have a moleskin lying around waiting to be helpful?
Action Item: Track all your miles, business and personal.
Here is the sixth and final point.
Whether you have neat and tidy Dropbox or file folders with all your business documents, receipts, and statements, here are some tips to get you started or help save some time.
Mostly importantly– You should save your tax return for seven years, receipts and bank statements for three years, and your business setup documents forever (LLC formation, business licenses).
Dropbox and Google Drive are great and have apps for your phone which make sharing and saving files with your accountant, banker, or contractor easy. Dropbox also has a secure and seamless way to request files from people and be notified when they are uploaded.
For receipts, you can use your bookkeeping system (Xero, Freshbooks, Bench, and Expensify all have built in receipt saving features). You can also use Receipt Bank if you need to manage invoices and payables as well.
Save your bank statements. This will keep you from having to pay $5 or $10 once your bank decides to no longer keep your statements on file. Each bank is different, but many purge their files in three, six, or 12 months. Use Hubdoc or FileThis to connect your bank and credit card statements to save automatically.
Better yet, connect these accounts to your Dropbox or Google Drive, and you'll never have to worry about finding your old statements again. Just make sure you reconnect the account if it breaks (software isn't perfect…).
Action Item: Set up a filing system on Dropbox or Google Drive. Use Hubdoc or FileThis to automate collection.
Bonus: Download these folders to help you stay organized all year long!
Here’s a quick look at everything we covered today:
If you can keep up with those five steps, you'll be in good shape for tax time, loan applications, or audits. A system’s strength really lies in its consistent application. If you have another idea, great! Stick with it. The key is to find a way that works for you to stay on top of this stuff.
If you’re looking for more on entities, what you can deduct, or how to pay your quarterly taxes, head over to timbertax.co/light-reading.
Download this issue of Tradecraft as a PDF to read and reference at your own pace.