Update 2020: What You Need To Know About Filing Your Personal Taxes

Published by Angela Lim on

1040 Tax Illustration for Me and My PF Personal Finance Blog
1040 Tax Illustration for Me and My PF Personal Finance Blog

The spiel

I know taxes isn’t the funnest topic, but if you make money, you’ll most likely have to file your taxes every year. I won’t be walking you through how to do your taxes step-by-step as there are way too many options. However, this post will walk you through some of the tax basics, tax goals you should strive for, tips (See why 9/10 accountants hate me!), and FAQs. With taxes there’s a crazy amount of scenarios! So please, please, please do your own research and seek a tax professional if you have some kind of funky scenario. Most of you are probably pretty basic and don’t need a tax professional (I’m looking at you Non-married, childless, W2 employees, living and working in 1 state, and renting), but it’s always good to be cautious! 

Why do I need to pay taxes and how do they work?

Taxes are extremely important for all countries since tax money is used to help run the government. That government pays to build and maintain roads, schools, vital government programs, etc. We vote on the people who decide how money is being spent, so if you’re unhappy about it, PLEASE VOTE, not just for presidents but for local and state elected officials as well!

In the U.S. we have a multi tiered, progressive tax system. High level, the more you make, the more you’re taxed, but total income is not taxed at a single tax rate but actually, at multiple different rates that increase with your income! Learn more in my previous tax post!

Your Goals for Tax Season

Be accurate with your inputs! You’ll thank your future self if you ever get audited by the IRS, and you may miss out on potential credits if you aren’t thorough. Also, keep your tax returns in a safe space as losing that can be a huge headache and people can steal your Social security number! 

Take advantage of every legal opportunity to reduce your taxable income. The goal isn’t to get a bigger tax refund, the goal is to legally reduce the total amount of taxes you owe. A lower taxable income means more overall money for you! (More on this later)

File your taxes ON TIME or you’ll face penalties! This can be both financial and legal penalties! Remember Al Capone? They couldn’t get him on the murders but they got him on 3 counts of tax evasion and was sentenced to 11 years in prison and fined over $50K.

When’s the deadline to file for Taxes?

Typically the tax deadline is April 15th for the majority of people and under normal circumstances. However, due to COVID-19, the 2019 federal tax deadline has been pushed back to July 15th, 2020. Many states also pushed their deadlines back to July 15th, 2020, but you should double check just in case! As of March 18, 2020 California has announced that the state tax deadline has been extended to July 15th, 2020.

Is there a way to extend the deadline? Yes, you can get a 6 month extension that pushes your deadline out to October 15th by filing Form 4868. However, this DOES NOT excuse you from paying any taxes that are due by the original April 15th deadline (of July 15th for 2019 Taxes). You must estimate any taxes you owe, make the tax payment by the deadline, and file for the extension prior to the deadline.You can e-file Form 4868 for free – see here for more info: Link If you’re expecting a tax refund, you’ll want to file on time to get that tax refund asap though! 

Benefits of Tax extension:

  • Gives you more time to get tax documents prepared. This is an obvious benefit, but if you are struggling to get all the necessary documents, getting an extension gives you several more months!
  • Avoid paying late fee penalties. If you end up underpaying taxes, you’ll have to pay interest on that under payed amount but not that hefty penalty. 
  • Extends time to collect IRS tax refund. If you failed to do taxes in prior years but are owed a refund, you have 3 years from the original deadline to collect that refund. However, if you file for an extension you can extend that 3 year period by an additional 6 months. 
  • Extends time to fund a Self-Employment retirement account. While the retirement account (e.g. Solo 401K or SEP IRA) must be set up during the tax year (i.e. 2019),funding the account can happen as late as the tax extension deadline. So if you’re struggling to fully max out the contributions you can ask for an extension for several more months to do so.

Who needs to file taxes?

Go to page 2 of this IRS page or here for dependents. But even if you don’t need to file you probably still want to because you can’t get any tax refunds without filing! See the FAQ for info. 

What if I just didn’t file taxes?

It’s mostly a financial penalty that’s calculated using this not so straightforward calculation. It’s rare, but if you egregiously fail to pay taxes you can face jail time, like Al Capone. If you failed to pay taxes for multiple years, the best time to figure it out is as soon as possible! Most likely you’ll probably want to talk with a tax professional to help you through everything. 

What type of filer am I?

You were not legally married on the last day of the year and do not qualify as any other status.

You were legally married on the last day of the year and you and your spouse are submitting one, joint tax return 

Jointly filed means jointly liable - There should be a high level of trust when you’re married and finances aren’t an exception! You need to trust that your spouse withholds enough taxes and is truthful about ALL income sources. It doesn’t matter if you are owed a $2K refund and your spouse owes $10K. You and your spouse JOINTLY owe the IRS $8K.

You were legally married on the last day of the year but you and your spouse want to file 2 separate tax returns. For the majority of married couples, this is not the move because it usually means higher overall taxes and no longer qualifying for certain tax credits or deductions. 

Sooo… why would you?:

Huge Medical Bill - For 2019, the IRS only lets you deduct out-of-pocket medical costs that are above 7.5% of your adjusted gross income. This limit might be hard to reach on a joint income. 

Separate tax liability - Since you’re filing separately, you are only liable for your taxes, not your spouse’s. If you don’t trust your spouse to be accurate with their income information or you just don’t want to risk being liable for their taxes this is a good option. 

Divorce - Maybe you’re going through a divorce and don’t want your significant other getting up in your business anymore or associating with them tax wise.

*CURVEBALL: If you live in one of these 9 community property states (as of 2019): Arizona, California, Idaho, Louisiana, Nevada, New Mexico, Texas, Washington, and Wisconsin and want to file separately, you need to still include any community income and community property in your tax returns. I’m not going into too much detail because only 2% of people file married filing separately, and less in a community property state. You can read more about it here: Link.

If you’re considered “unmarried” you may be able to qualify as Head of household which can result in lower taxes than being “Single.” You need to meet these conditions to qualify:

Unmarried or considered unmarried on the last day of the year

You paid more than 50% of the cost of keeping up a household for a year which includes rent/mortgage, utility bills, insurance, property taxes, groceries, home repairs, and other home related expenses. 

A qualifying person lived with you in the home for more than half the year (except for temporary absences, such as school). However, if the qualifying person is your dependent parent, he or she doesn't have to live with you. See Special rule for parent, later, under Qualifying Person.

If your spouse died in 2019, you can file as Married filed jointly with your deceased spouse for the last time with the 2019 tax return or file as a qualifying widower. You can then be eligible to file as a Qualifying widower for the 2 years after the death of your spouse if you don’t remarry. The biggest benefit would be that you can still use the highest standard deduction (reserved for Married filing jointly couples) for 2 more years which can save you a lot of $.

Typically, if you’re a single, child who is largely supported by someone else, you are considered a dependent and can be “claimed” by whoever is taking care of you (i.e. parent, family member, foster parent, older sibling, etc.) so that they can get some tax credits. Other relatives can be considered a dependent (i.e. parents or grandparents) if they meet certain criteria. Instead of attempting to write out every scenario it’s easier if you take the IRS’ “Who May I Claim as a Dependent” quiz.

How do I maximize my tax returns?

Trick question! Contrary to popular belief, your goal should definitely not be to maximize your tax returns, as doing so means you’re overpaying for taxes, and basically giving the US government an interest free loan. Instead, you should aim to pay the correct amount of taxes! Going from overpaying taxes throughout the year to paying the correct amount, increases your net pay (aka the money that actually hits your bank account), which can be used to pay down debt, invest, save, or spend throughout the year. 

How do I make sure the correct amount of taxes are taken out of my paycheck? Whenever you get a new job or some tax related event occurs (e.g change your tax filing status, have a baby, get a second job, etc.) make sure you give your employer a W4/updated W4 (which employers have to give you during your on boarding process). Starting 2020, the IRS got rid of the choice to get rid of tax allowances which made filling out W4s easier. Usually, you just have to put down personal information, filing status, and number of dependents. However, if you have multiple jobs or other sources of income (like rental income), you will probably want to hold back more for taxes so you don’t end up with a large tax bill. Luckily, the IRS provides us with a free tax withholding estimator for whatever scenario.

How can I reduce my tax bill?

This is different from simply trying to maximize your tax return. Getting a large tax return means you overpaid taxes throughout the year, while reducing your taxes means just that, you paid less taxes overall.

What can you do in 2020 to reduce your 2019 taxes?:

Contributing to your 2019 Traditional IRA (max of $6K or $7K if you’re 50+ yrs old) – Contributing to your Traditional IRA can reduce your taxable income dollar for dollar, if you’re within a certain income bracket. For example, say you’re a “Single” wage earner who made less than $65,000 in 2019, if you contributed $6,000 to your traditional IRA your taxable income would decrease to $59,000 ($65,000 – $6,000). Unlike a 401K, you can contribute to your IRA up until the Tax deadline, which again, is typically April 15th. But due to COVID-19 has been extended to July 15, 2020. If you contribute for 2019 in 2020, make sure that you correctly contribute to the 2019 IRA and NOT for 2020. Check the IRS website or my IRA Post to learn more and make sure you qualify for the taxable deduction!

  • Bonus: If Self-Employed, you can contribute additional money to a SEP IRA or Solo 401K. Note that Solo 401ks must have already been established by December 31st, 2019 for 2019 but contributions can be made until the tax deadline. So if you haven’t already opened a Solo 401k in 2019 and elected to make a contribution, go with the SEP IRA. 

Contributing to a 2019 Health Savings Account aka the HSA – Did you have a high deductible health plan AKA HDHP << For those on individual HDHPs that means your health plan has a deductible of at least $1,350 and for those with family HDHPs, a deductible of $2,700. >> in 2019 and meet the following criteria?:

  • Have no additional health coverage (i.e. have coverage under more than 1 health plan)
  • Not enrolled in Medicare
  • Can’t be claimed as a dependent on someone else’s 2019 tax return
  • For family HDHP, you must meet the deductible qualification, the above 3 criteria, and have at least one other individual covered as well. 

If so, you can reduce your tax bill by contributing to a 2019 HSA up until the Tax deadline, which is typically April 15th, 2020 but has been extended to July 15, 2020. For 2019, individuals can contribute up to $3,500 ($4,500 if you’re 55+ yrs old) and those with a family HDHP can contribute up to a combined family total of $7,000. 

Note: You cannot open a joint HSA where there’s more than one account holder. So if you’re married and both you and your spouse want to contribute to HSAs, make sure you both qualify and the combined total contributions are no more than $7,000 for 2019. The contributions don’t have to be equal, it can be $6,000 and $1,000 or whatever other combination, but it must be a MAX amount of $7,000. 

Note II: Technically if you were HSA qualified as of December 1, 2019 you can make a full 2019 contribution by the 2019 Tax deadline. However, you can be tax liable for some/most of the contribution amount + owe a 10% penalty fee if you fail to remain HSA qualified until December 1, 2020. More info here. So if you want to play it safe I recommend only contributing up to what you’re already qualified for. For example, if you were individually HSA qualified from July 1, 2019 – December 31, 2019 that means you were HSA qualified for 6 out of 12 months in 2019. You can contribute up to $1,750 for 2019 (6/12 * $3,500 = $1,750) without having to worry about being liable for any taxes or penalties.

How do I actually file taxes?

There are several free and paid options when it comes to filing taxes. If your taxes are generally pretty simple (e.g. you’re a W2 employee with a single job with no large tax events), you can probably do your taxes without any paid software, but not going to lie, it’s nice to have everything auto calculated, and in some cases these tax software are free. But if you want to, you can file for free online or by manually filling out the tax form and mailing it if you really want (this isn’t recommended since it takes much longer to process and mail can get lost). Otherwise, here are some tax software options to help you out:

1. If your 2019 income was $69,000 or less you can qualify for one or more free Federal/state file options shown here.

2. Redditors highly recommend Free Tax USA. The tax software is fairly easy to use and BEST OF ALL, is FREE for federal taxes and only $12 for each state tax return! I’ve actually been using my dad’s CPA to do my taxes the last few years, but I used freetaxusa.com to double check my outcome with his and lo-and-behold I found out that the CPA actually mischaracterized my HSA contributions and I’m actually owed more money back! Other than that, my results were the same as the CPA’s.

3. Another very popular option is of course, Turbo Tax. But it is more expensive than freetaxusa.com, and if you’re not the typical W-2 employee, then it can quickly get a bit pricey. 

4. If you have a somewhat complicated tax return or would really love to have a professional explain things to you, you may want to look into getting a certified CPA. Some more complicated tax events could be: selling a house, working abroad, an inheritance, being self-employed, having large medical events, etc. Depending on the situation hiring a CPA can cost anywhere for $100 – $300+. You should first ask your friends if they know a good CPA! 

5. If you’re super confident with yourself, you can just e-file or mail in your tax return for free! I recommend e-filing as your tax return can get lost via physical mail and takes significantly more time. Here’s the link to e-file directly. I recommend double checking your work with a tax software just in case (you can fill out all the info and just not file through the tax software) as amending taxes is annoying.

Amended Tax Returns to fix prior mistakes

First off, if your mistake means you should be owed a larger tax return, then you have up to three years to file a tax amendment to receive your updated tax refund, and you will not be penalized. I know you may be eager to get that tax refund, but wait until the IRS has fully processed your originally filed tax return as there’s a chance the IRS already caught the mistake on their end. But if they didn’t, first use the IRS’ tool to double check that completing a tax amendment is the right move. If so, you’ll have to physically mail the tax amendment, e-filing is unfortunately not an option. It takes the IRS up to 16 weeks to process tax amendments. 

If your mistake means you actually owe more taxes than previously thought, the IRS might catch your mistake and simply send you instructions to follow, which may exempt you from actually having to mail in a tax amendment. If the IRS processed your taxes and did NOT catch your mistake then mail in that tax amendment asap and most importantly, pay that additional tax amount ASAP to avoid penalties/larger penalties. Just an FYI, not paying taxes is technically considered a misdemeanor and if the taxes owed is egregious, ignoring to pay them can mean you could potentially go to jail! Yikes. 

Frequently Asked Questions (FAQ)

“Getting a raise can put in a higher income bracket and result in a lower overall income” - this is only a half truth! Yes, getting a raise can push you to a higher income bracket which means you will pay more in taxes overall. HOWEVER, the U.S. federal tax system is based on a progressive, tiered system and bottomline, you’ll make more money from a raise every time, trust me! Check out the examples in my previous tax post!

Most likely, yes! If you worked a part time job or summer internship, most likely, the company withheld taxes from every paycheck. As you should know from my previous tax post, for Single filers, at minimum, your first $12,200 (for 2019)  in income is not taxable due to the standard deduction. So, if you made less than $12,200, you are most likely owed all the taxes that were withheld for federal taxes! You can also be eligible for a tax refund from your state as well! And your taxes should be fairly simple to do so ask your parents about it! 

Congrats and goodluck! Your very first step is to talk to your parents/guardians on whether you should stop being claimed as a dependent. There are many instances where this discussion isn’t made early on, and causes trouble come filing time. If you just graduated/or about to, but won’t start your job until late in the year and will still be relying mainly on your parents to live, you’ll probably be considered a dependent. However, if you’re going to start working soon and will be moving or making those life payments right away, you probably want to discuss the possibility of filing as an independent filer starting this year.

Most likely yes! If you made less than $400 and made no other income, then you most likely don’t have to even file taxes. Otherwise, legally you must include the self-employment income. If you’re a contractor or worked via ridesharing or Airbnb, you’ll be issued a 1099 which states how much you earned (always double check the numbers). If you’ve got a simple operation, there’s no need to set up a Corporation or even an LLC, you can simply fill out Schedule C and include the income in the proper section of your personal tax return. Self-employed folks are responsible for not only regular taxes, but also self-employment taxes which is a cost that’s shared with your employer if you’re a W-2 employee. But you can also deduct eligible business expenses as well (which W2 employees usually can’t do) which can significantly cut down on taxes! Learn more at the IRS’ Self-Employment Tax Center.

Your employer must give you or mail you your W2 by January 31st, so if you haven’t received it by mid-February you should definitely start with contacting them. If your employer is non-responsive, you can call the IRS to complain as this is a big no-no for employers to do. You can read more about this here.

Register for an IRS account! Everyone should do it. It takes < 15 min to do. Just go to the Get Transcript account registration site. On the top left you'll see "Return Transcript", the years underneath indicate that taxes were filed for those years (up to the last 4 years). You can check the details by clicking on the years. The wage info (bottom right) goes further back. If you need a physical copy of the tax return, it costs $50 and you can get it for the current year and 6 years back by mailing in Form 4506.

Bonus: COVID-19 Related REsources

I got laid off/had my work hours reduced. What should I do?

  • File for unemployment ASAP.  Due to the number of people filing for unemployment the wait times are long and it can seem impossible to get anyone on the phone, but don’t give up! It can be a HUGE help. Also, with the CARES Act that passed, those who qualify for unemployment benefits will receive an additional +$600/week on top of the typical unemployment payout. Check out your states unemployment portal for more info!  Here’s the link for California’s.
  • Have Federal student loans? Good news, they’re on temporary forbearance from March 13th, 2020 – September 30, 2020! Make sure that it shows that payments have been temporarily suspended, if not talk to the lender and let them know. If you can comfortably pay for them you should, but if you need a breather take it! 
  • Struggling to pay the mortgage? Good news, you should be able to defer your mortgage for 3-6 months! In many cases you’ll be able to apply for a COVID-19 hardship through your lender’s website, but if you can’t give them a call. Also ask the lender what deferment means for you. It may mean that the interest still accumulates or that you can just extend the life of your loan. 
  • Look for ways to cut out unnecessary spend! Gym membership, eating out, shopping, etc. Try to cut down unnecessary spent as much as possible!   
I should’ve gotten the stimulus check, but I still haven’t gotten a deposit or check!
  • Go to Get My Payment on the IRS website to get updates and read the FAQs. Unfortunately you may have to check in several times if there’s no update the first time. I helped my sister do this and she just got her Stimulus check.

TL;DR - But you should at least check out the FAQs

  • The tax deadline is typically April 15th, but due to COVID-19 the 2019 tax deadline has been pushed to July 15th, 2020.
  •  Even if you don’t have to file taxes, it’s most likely beneficial to do so! This is because you can only get a tax refund if you file. The IRS will not give you a tax refund otherwise.
  •  Your tax goal should be to minimize your overall taxes owed, not to get a large tax refund. Getting a large tax refund means you’re over paying in taxes and giving the government an interest free loan! You can minimize your taxes by contributing to tax advantaged accounts (e.g. 401k, traditional IRA, & HSA) and by making sure you’re W4 information is correct. 
  • Turbo Tax is not the only tax software option! if you make $69,000 and less, there are a ton of free options. Also, Freetaxusa.com offers FREE federal tax filing for everyone and $12 state filings.
  • You don’t have to be laid off to qualify for unemployment! If you’ve had your work hours cut down, you may qualify too! With the CARES you get an additional +$600/week on top of regular unemployment payouts until July 31st. 


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