I believe that every person in the tax policy game—from members of the tax-writing committees to research assistants at the Tax Policy Center—should compute their own taxes. How better to understand the law and taxpayers’ experiences and have fun too! I have done my own taxes since I received my first W-2. But for the first time, my travails this year made me wonder if I should buy tax preparation software.

I didn’t and I won’t, but I faced the perfect storm this filing season. The federal tax law changed, DC law followed, the income tax forms were “simplified,” and I received an unplanned but very welcome infusion of money at the very end of 2018.

As in recent years, I used the Free File Fillable Forms available on the IRS website. Unlike its sibling “Free File,” the software does not calculate your taxes, but it does the math and allows you to file electronically at no cost.

Note to reader: The rest of this blog is full of self-pity about first-world problems. I am ashamed.

Let’s start with the impact of the Tax Cuts and Jobs Act (TCJA), 2017’s tax overhaul. TCJA increased the standard deduction for federal income tax purposes and DC followed suit. That was a great step for tax simplification. Except for people like me. You see, I had just enough in local taxes and charitable contributions that I could not know if I should itemize or take the standard deduction until I actually computed my federal and DC taxes.

So on Oscar Sunday (the traditional start of my filing season), I began compiling my records — thank you notes from charities and DC tax documents. A few weeks later, I was done. Itemizing had the financial advantage—by a few hundred dollars. Nothing to sneeze at, but perhaps I could have used those hours in better ways.

This year I will reach a certain age, and my standard deduction will rise. Unless I increase my contributions to charities (which I should) or incur large medical bills, I probably am done with itemizing deductions. But what else will I do during the Oscars?

Then there was the new postcard form 1040. As others have noted, it is no postcard at all. The IRS just moved lines to new forms. Because it removed the capital gains line from the new Form 1040, I initially forgot to include my gains (now on Form 1). The changes also required me to copy information from schedules to the forms and finally to the 1040. This was annoying.

My biggest complaint about the new “postcard”? After taking all the trouble to move lines off the 1040, why did the form-writers keep the font still so small?

There was more. I did not have a long-standing plan to retire from the federal government last year and join the Tax Policy Center. If I had, I might have given more thought to the consequences of getting a check for more than three months of unused vacation time.

That money funded plenty of good meals, gifts to family members, last-minute charitable donations, and savings for my real retirement someday. But it also catapulted me into the income range where various surtaxes kick in.

And, here, commercial software could have made a difference. The brain works in mysterious ways. Even though my career is based on my knowledge of tax policy, my self-image has not caught up with my income—and it never occurred to me that I’d be subject to those surtaxes.

What woke me up? I participated in the beta testing of  TPC’s tax calculator. When it computed a higher tax bill for me, I thought I had found a bug. Nope. The details told me what I had ignored: I owed both the net investment income tax and the additional Medicare tax. But here’s another annoyance–when I checked out the IRS publication on the net investment income tax, I found the Service had not updated it to reflect the TCJA. More confusion! More frustration!

And yet…despite my misery this filing season, I still believe that those of us who influence the tax lives of others—through our jobs and our writing—should do our own taxes without the assistance of a preparer or software. What doesn’t kill you makes you stronger, after all, and I learned new things about the tax code, the cognitive process of taxpayers, and my own arrogance.  I also learned I should take more vacations—those days are tax free, but their monetary value is not!

Besides, commercial software probably wouldn’t save me any time. I know me—I would double check every line.