The Best Way to File Taxes Online (+Step-by-Step Instructions)


Oh, hi tax season.  You sneak up on me every year, you little rascal. Even though I cover personal finance topics, I'll admit I'm still pretty clueless when it comes to filing taxes. I mean, I know I have to be organized and file them each year, but outside of this…that's about it. My money circumstances have changed a lot over the six years I've been running this blog and filing taxes: from broke administrative assistant in NYC, to freelancer, to full-time blogger, to back to full-time employee with a blog side hustle, but even those without such complicated finances can find tax-filing intimidating. No matter your own lifestyle, you may be wondering – what's the best way to file taxes online for my situation?

Below I provide the answer, and also list out step-by-step instructions for filing your taxes stress-free. You're welcome.

Step #1 – Preparation is CRITICAL

Really, tax prep should start Jan 1st, and I learned this the hard way when I first started working for myself.

First, save all of your receipts – for business, for work, and especially for any healthcare expenses. Save receipts when doing upgrades on your home (if you own a home.)When in doubt, just save it. I keep all of mine in this handy receipt catcher and then (attempt to) go through it quarterly. I track expenses for my blog/side business in a Google Spreadsheet monthly when I'm updating how much income I made. 

I keep online purchases (like when I pay contractors through Paypal, when I pay for web hosting, things like that) in a separate folder in my Gmail labeled 2017 – Expenses. This way, I can see monthly what I spent and at the end of the year download an archive into a dropbox for posterity. (I'm a keep a copy for my records kind of girl. #mawmaw)

Then when it comes time to file taxes, it's time to corral all of my documents together and I do it over the course of three weekends.

  • First weekend (Income + Extra Forms) – I double check how much I made, and make a list of all the W2's/W9's I'm set to receive. As they come in, I check them off the list. (this year, I put them in a file until I was ready to look through them.) I also go ahead and download any investment income, documents for my mortgage, and make sure I have health insurance verification.
  • Second weekend (Expenses) – I calculate up all of my expenses and things I want to deduct. I make sure my spreadsheets are accurate and that I have paper copies (in case of an audit) organized and in one place.
  • Third weekend (Final Review) – I put it all together and hunt for any missing pieces (if any.)

This is the way I've found it works best for me and I recommend doing it this way so it doesn't get overwhelming and you're not attempting to put it all together….all at once. How do you eat the tax elephant? One bite at a time! Even if you're filing at the last minute, the important thing to remember is that if you're organized all year long (hint: not throwing important documents around willy-nilly) you will be ahead of 80% of the population come tax time.

Related: How the New Tax Plan Affects Homebuyers


Step #2 – Choose How You'll File

You can choose any online filing service or hand over documents to an accountant. I like TurboTax, and spoiler alert: the content below is a tutorial of filing on the TurboTax platform. Here's why I like it:

I have used TurboTax before when I was out of college and in the working world with a straight-forward W-2 job, and TurboTax definitely made filing my taxes a seamless, pain-free process. The last few years, I’ve been using an accountant while working for myself and because I had several complicated state tax credits for the renovation of my historic home, now rental property.

With recent updates to the TurboTax software, I was excited to give it a try and see if it really makes doing your taxes easier. Easier than just handing off papers to an accountant? No, but the cost savings are pretty significant as you can file your taxes, even if you’re self-employed, for just $119 bucks, and I definitely felt this was worth the price and there wasn’t any hassle involved.

There’s a tutorial for you below + my tips and tricks for how to file your taxes with TurboTax.

Related: Nervous about Tax Season? Meet TurboTax Live

Step #3 – File. Here's the Best Way to File Your Taxes Online (Hint – It's TurboTax) + The Complete Tutorial

Step 1 – > Create an account

You can do that here.  

Select the plan you feel best fits your financial situation. If you're just doing a simple 1040, you can file your federal with TurboTax for free! The account below is skewed more toward those who are self-employed/work in the gig economy, but the steps for those with just one W2 and taking the standard deduction (you lucky ducks!) are much the same.

Step 2 -> Tell TurboTax about your tax situation

As you can see, TurboTax is stepping up their game quite a bit, and you can now select a variety of options. This is way more advanced than what they offered even just a few years ago, and I was excited there was a button for every scenario I encountered this year, between my multiple streams of business and rental income.

I selected “Single”, “Own a Home”, “Own a rental property,” “Maximize Deductions” and “Own my own business/independent contractor.” PHEW!

Step 3 -> Select Your Plan

Based on what you’ve told them about yourself and your filing status, TurboTax will make a recommendation on the type of product you should use. I selected the “Self Employed” product for just $89.99.

Step 4 -> Tell them More About Yourself & Your Financial Picture


You can already see how easy and self-guided this is.

On the next two screens you’ll answer questions about marital status, and the kinds of financial transactions you engaged in over the course of 2016. One important thing to note is that if you are self-employed and did not work with a company as a contractor, you won’t select the “I Had a Job” button.

Pro Tip: If you had one of those years where you worked a job at a company and then left to work for yourself, you’ll select the “Had a job” button, and be prompted to enter in W2 information later on in the “Personal” section.

Step 5 –> Enter in self-employment information.

At this point they’ll do a “check-in” and it looks like this. If all looks good, continue. (But don’t worry, you can change it later if you need to!)

P.S. I’m really loving all the gamification TurboTax has done to their software. It makes doing my taxes fun!

Step 6 -> Finish entering in your personal information.

When you’re finished, TurboTax will recommend a filing status for you and do a summary of all your personal information. If all looks good, click continue!

Step 7 -> Choose How You’d Like to Enter in Your Information

Okay, here’s where you get to pick and choose. In one option, you can have TurboTax self-guide you, or you can choose what you want to work on. There’s no “bad” choice!

Which one you choose really depends on if you’re the type that sits down, files their taxes, and has all the paperwork organized and ready to go so you can answer the questions. If you’re working on your taxes little by little, you can choose your own sections to work on as the information becomes available to you.

Pro Tip: For convenience sake, I recommend selecting the “walk me through everything” button and if you don’t know something you can come back to it later.

Over the next few pages you’ll confirm your business name and address, and if you paid any wages. Wages apply if you have full time employees you pay with a W-2, or if you pay contractors (they’ll need a 1099.) TurboTax has the option to create these for your staff if you haven’t already done so.

Pro Tip: If you’re unsure of something, TurboTax has a lot of links to click on with thorough answers to your questions. See the “What paperwork do I need?” link above. Each step of the process has links like this on the page so you can proceed with confidence!

Step 8 -> Enter your EIN, Lookup Your Business Code, and Answer Questions About Your Accounting Method.


Keep going until you hit the business summary page. It will outline for you all the sections you still need to work on!

Step 9 -> Enter in Business Income

So, here’s where it gets a little more involved, but TurboTax still makes it super easy. If you’re a business owner, you should keep a simple Profit + Loss sheet totaling up how much you make and how much you spent on the business for each month of the calendar year.

Pro Tip: I know it can get a bit tricky, especially if you freelance or own a blog business. For myself, I entered in all of the income I got a 1099 for, and then subtracted that from what I earned and claimed the other as “General Income.”

Step 10 -> Enter in if you have any inventory.


Step 11 –> Enter in business expenses you’ll be claiming.


They’ve listed all of their “common” business deductions so you don’t have to worry about remembering them all. TurboTax will walk you through both mileage and home office deductions with ease.

Step 12 –> Enter information about your business assets.

Step 13 –> Continue to Personal Information, State Taxes, and Review.

Step 14 -> Now You’re Ready to File!

Pro Tip: TurboTax really does make filing your self-employed taxes a snap, but the process will go a lot smoother if you organize your records: The P+L, the receipts, and the 1099’s (if any) in one place before you get started.

Cheers to saving money and leveraging technology to make running a business easier in 2017! Were you surprised by how easy this process is?

Click here to file your taxes with TurboTax.

*thanks to TurboTax for sponsoring this post.

Tax time is here, and we all know what that means! Confusion, anger, and frustration. But it doesn't have to be that way! See how to file your taxes with TurboTax, even if you work for yourself!

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  • Erica Holland | ModMoney
    February 16, 2017 at 5:43 am

    This is a great tutorial! I started using TurboTax 4 years ago, and my taxes have been so easy every since. Is it weird that I actually look forward to them now?

    • Lauren Bowling
      February 19, 2017 at 9:28 pm

      Not weird. Especially since it’s almost like a computer game to go through 🙂