March Learning: Doing Taxes in Retirement: Can’t We Ask Siri?

Photo by Nataliya Vaitkevich:

AI Apps can do everything! Why not do our taxes?

AI Apps are all the rage these days. They can even write poetry!

But you know what they can’t do? Our taxes!

Why, in this day and age, do we not have an app to do our taxes? Yeah, I know about Turbo tax and all the other software out there, but even using the tools, taxes are so unbelievably complicated! At least for me.

This month, my goal was to learn more about managing my money in retirement. My “deliverable” was to do my own taxes.

When I retired a few years ago, I was very intentional about only wanting to spend time on activities that brought me joy. Doing my taxes does NOT bring me joy, so I had been continuing to delegate that task to my accountant.

However, I have plenty of time now and this year my theme is continuous learning. March 2023 would be dedicated to learning more about money and by the end of the month I’d have my taxes done.

Learning about taxes in retirement

Even though doing my own taxes this year was very frustrating, I’m glad I persevered. Here are some of the benefits and things that worked well about doing my taxes myself:

  • Now I am much more aware of what deductions I can make so I will do better at record-keeping and should be able to lower my tax bill going forward.
  • I’ll save the money I was spending on an accountant.
  • I was able to exercise my brain (something that I need more of, now that I’m retired.)
  • I ended up using Turbo Tax because the service included access to accountants who could step me through the tricky questions and double-check things for me. It was nice to have that service, but I don’t think I’ll need it for future years.
  • I also went to a seminar at the library and learned more about Social Security and Medicare benefits and how those would be affected by taxes. (I just turned 63 and I’m not collecting Social Security yet, but trying to understand all the tax implications now.)

Playing with AI is more fun than doing taxes in retirement

What did NOT work well for me about doing my taxes is that I really procrastinated working on them. I also did not spend nearly the amount of time learning about money management that I wanted to this month.

There are plenty of resources – podcasts, books, Websites, courses, etc. that are available to help us manage our money in retirement. I was planning on really digging in, but I did the bare minimum to get my taxes done.

One of my distractions was all these new tools and apps that use AI. They are super-cool and impressive! I couldn’t believe that the tools could write blog posts and poems in just a few seconds! It was amazing and also… sort of depressing. Blogging and poetry are two of my only creative outlets.

Experimenting with AI – Poems about Doing Taxes

When I was procrastinating with doing my taxes and experimenting with AI, I asked an app called “Chatster” and Google’s “Bard”, to “Write a poem about doing taxes.” Though they aren’t too bad, I think I could do better.. but I’ll save that for another day.

This is what they came up with:

Chatster poem:

Taxes, oh taxes, a dreaded chore

A task that I cannot ignore.

With forms and receipts, I must prepare,

To ensure that I pay my fair share.

I gather all my documents.

And sort through every cent,

Calculating what I owe,

And what I may get back, you know.

I enter numbers line by line,

And hope that I don’t make a mistake this time.

For the IRS is ever watchful,

And mistakes can be quite costly, so I’m mindful.

But as I finally hit submit,

A sense of relief begins to hit.

For though it may have been a pain

I know that I have done my duty as a citizen.

Bard poem:

Taxes, oh taxes,

How I hate thee!

Let me count the ways.

I hate the way you make me feel,

Like I’m being robbed of my hard-earned money.

I hate the way you make me spend hours filling out forms,

When I could be doing something more productive.

I hate the way you make me feel like I’m always being watched,

Like I’m never free from the government’s grasp.

But most of all, I hate the way you make me feel like I’m not good enough,

Like I’m not contributing my fair share.

But even though I hate you, taxes,

I know I need you.

You’re the price we pay for living in a proper society.

So I’ll do my taxes,

And I’ll grumble about them,

But I’ll know that they’re necessary.

And maybe, just maybe,

One day I’ll even learn to love you.

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