Of all the complexities I have encountered during my journey through widowhood, none have been more daunting or intimidating than filing taxes…

Let me be perfectly clear, widowhood as a whole is quite simply like being waterboarded with gasoline on a regular basis, but filing taxes as a widow is just another circle of hell…at least for me.

I’ve never been good with numbers, math was always the toughest school subject for me. I’m not exactly sure why, but all I know is that numbers have a tendency to get all wibbily and mixed up when I try to read them. So understandably, filing my own taxes has always been a scary concept.

luckily for me, when time came to file my own taxes, I was in college and they offered free filing services for students. The universal timing of my marriage just happened to coincide with tax season in such a way that the next time I had to file, Craig was there and offered to do it for me. From that point on, he just assumed the role of “tax preparer” for our household. I would track the various mailings, and ensure he had all the documents on his checklist to do our filing, but beyond that, he happily managed that task.

All of that came crashing to an abrupt end when Craig died. Not only did I have to assume the responsibility of filing taxes, but I had very little lead time to prepare for this new and daunting task. Craig passed the end of November, December was a blur, and by time January rolled around, I was becoming increasingly aware of the lack of income, so I logged into his Turbo Tax account and gave it a shot.

At first glance, all seemed to go fairly smoothly, I followed the prompts and discovered that I’d still be filing as “Married filing jointly”. COOL! that meant I could import a lot of info from the previous year and after about 30 minutes I submitted the return feeling triumphant.

Fast forward to the next tax year. I felt confident having one year of filing under my belt, so I opened Turbo Tax once again and proceeded to start my return. This is where the struggle began. The questions were different, My filing status changed, There was required documentation I couldn’t find… I quickly became overwhelmed and full of grief stricken rage. I shouldn’t have to do this, Craig was supposed to be here!

I hit the pause on filing myself and started doing some research and ultimately ended up paying for the expert filing feature from Turbo Tax.

Boy, was that a mistake.

I’m sure for most situations, it’s a perfectly viable option, but for me, it was a nightmare. I had a change in status, change in income, change in job, had bought a property, sold 2 cars, rolled over a 401k to an IRA, as well as a few other things that extremely complicated things. Then to top things off, I got audited.

(What I didn’t know, about the Turbo Tax pro was that they had multiple tiers to choose from, some of which included audit protection…. the one I was sold did not).

I spent several months working to sort things out, and come June, I FINALLY received a return. The following year rolls around and I decided from the start to pay for the pro version, because I didn’t want a repeat of the previous year. Everything seemed pretty straight forward and I felt a relief, maybe I had finally found a groove with this whole tax nonsense. About half way through the filing, I received a tax document for Craig that had the previous tax year stamped on it. Confused, I scan it into the pro and ask what it is. They aren’t sure but include it in the return they filed for me. Bing, Bang, Boom… we were done! Or so I thought. I received part of my return about 6 weeks later, only to receive a tax bill for double the return 3 months after that!

Long story long, fast forward to this year… I was late filing and panicking about the complexity of being a new business on top of the experience I had already had with taxes, so I made the decision to hire an actual CPA. Come to learn, The tax bill is because the life insurance I received from Craig’s employer.

Now, I know what you’re thinking, “Life insurance isn’t taxable”, to which I say, you’re correct! However, the way this check was disbursed and the associated tax document (which I received a year late) were documented in such a way that it was reported as “additional miscellaneous income”. So now the IRS thinks I misreported my income for my return 2 years ago!

It’s a huge mess I’m working to clean up.

But I think the real surprise to me was, that after 3 years, there’s still “bereavement” pieces to be dealt with.

So how do you avoid the headache that I’m enduring?

Understanding Your Filing Status

The first step in filing taxes as a widow is determining your filing status for the tax year. Most widows will file as either "Single" or "Qualifying Widow(er) with Dependent Child." The latter status is available for the two years following the year of your spouse's death if you have a dependent child and meet certain criteria. Choosing the correct filing status is crucial, as it can impact your tax liability and eligibility for certain credits and deductions.

Gathering Necessary Documents

Before you begin the tax filing process, gather all relevant documents, including:

W-2 Forms: If you are employed, you will receive a W-2 form from each employer, detailing your earnings and taxes withheld.
1099 Forms: If you received income from sources such as freelance work or investments, you will receive 1099 forms documenting this income.
Social Security Statements: If you receive Social Security benefits, you will need your annual benefit statement, which outlines the total benefits received.
Documentation of Deductions and Credits: Keep records of any deductible expenses, such as medical expenses, charitable contributions, and education expenses, as well as documentation for any eligible tax credits.

Understanding Tax Benefits for Widows

As a widow, you may be eligible for certain tax benefits and deductions, including:

Survivor Benefits: Social Security survivor benefits may be taxable depending on your total income. Understanding the taxability of these benefits can help you plan accordingly.
Filing as Head of Household: If you have a dependent child and meet certain criteria, you may qualify for the Head of Household filing status, which offers lower tax rates and a higher standard deduction than filing as Single.
Estate Tax Considerations: Depending on the value of your spouse's estate, you may need to address estate tax implications. Consulting with an estate planning attorney or tax professional can help you navigate this complex area.

Seeking Professional Assistance

Given the complexities of tax laws and regulations, many widows benefit from seeking professional assistance from a tax preparer or financial advisor. An experienced professional can provide personalized guidance based on your individual circumstances, ensuring you maximize tax savings and avoid costly mistakes.

Planning for the Future

In addition to fulfilling your current tax obligations, it's essential to consider long-term financial planning as a widow. This may include updating your estate plan, reviewing beneficiary designations, and exploring investment and retirement planning strategies. Working with a financial advisor can help you develop a comprehensive plan that aligns with your goals and priorities.

Filing taxes as a widow can be overwhelming, but with proper guidance and preparation, you can navigate the process with confidence. By understanding your unique circumstances, you can ensure compliance with tax laws while maximizing financial security for yourself and your loved ones.

Remember! you don't have to navigate this journey alone— Something I wish I had figured out much sooner! A common misconception is that filing yourself or using self-serve software will be a cheaper alternative, but the fact of the matter is, you get what you pay for and many CPA rates are actually comparable to places like H&R block or Jackson Hewitt .Reach out to trusted and licensed professionals for support and guidance.

“Of life’s two certainties, the only one for which you can get an automatic extension, is taxes”

Death and Taxes: tackling life's only guarantees when they intersect