69 Comments

Wow. Taxes, TS Eliot, Ezra Pound AND Better than Ezra (which was a fantastically deep connection - damn) in the same few paragraphs! Love it. And for an artwork that captures perfectly the deadly tedium that is taxes and the IRS ... check out David Foster Wallace’s THE PALE KING. Painful in many ways, but worth it.

Expand full comment

I’ve read many of DFW’s essays, but I’ve never read his novels. At some point, I’m going to correct that. Should I read them in order, or could I start with The Pale King?

Expand full comment

I wouldn't start with The Pale King - it makes doing taxes look like fun. I only read it to the end because I'd read all of his other stuff - and as it was published incomplete and posthumously, I was curious. My favourite DFW are his essays, but he also has some really good short stories, too. As for the novels, if you're going to do it you need to dive straight into the deep end and read Infinite Jest. I read it when it was first published - my first DFW - in hardback/doorstop. It's tough going, but worth it. There's a reason it's compared to Gravity's Rainbow.

Expand full comment

Good to know, thanks! At some point, I'll jump into the deep end for DFW and Pynchon. But for now, I swim the shallow end with DFW essays and Pynchon's Inherent Vice (one of my favs).

Expand full comment

Inherent Vice is great (I also really like the film). And there's nothing wrong with the shallow end - as long as the water doesn't become too warm when the little kids swim by.

Expand full comment

I really enjoyed the film too. I know people kind of hated on it, but I thought it was a really strong adaptation. And yes, if I feel an abnormally warm water anywhere in the pool, I'm out!

Expand full comment

I need to read DFW’s tax novel as well

Expand full comment

😂😂😂

Expand full comment

1. The real reason I want to get famous is so that when I die and people go through all my stuff, they'll discover all the insane crap I wrote to myself over the years. Though I do wonder if they'd find me as charming and hilarious as I find myself in those musings. Probably not. Self-notes inevitably become inside jokes. With a very select audience. Of one. 😂

2. I used to work for myself as a personal chef and those tax years were brutal. Mainly because I'm too effing honest about everything. And I make (complex) systems. But the last two years I made approximately $0 as a writer, so my taxes have pretty much returned themselves! Easy peasy queasy. 🫠

3. April in New Hampshire is a crap shoot. Two days ago, it was sunny and 85 degrees outside. This week it will be dreary and in the 50s. April is unreliable.

4. Not answering the question so much here and showing my appreciation for your rewrite of The Waste Land's opening lines. And you didn't even need ChatFaceBot to help you write it. Human brains unite!

Expand full comment

Down with ChatFaceBot! As my old mom would say, "Shit or get off the pot!"

( Can I say that on Substack?)

Expand full comment

You can say all kinds of shit on my Substack.

Expand full comment

oh, goody.

Expand full comment

You can say ANYTHING on Substack! And I'm a big fan of profanity, so your mom is very cool in my book. I always heard it as "piss or get off the pot!" but the sentiment is the same. 😂

Expand full comment

Good to know. Thanks

Expand full comment

"There are lots of ways to estimate your quarterly revenue as a freelance writer, but some of my favorites include: wishful thinking..." Ha ha ha ! That would be me!

Expand full comment

Sharron, I just want to say thank you for going the extra mile and reading the footnotes! Not everyone does, but those who do get little easter egg jokes. Glad this one made you LOL.

Expand full comment

I read every Estrin word. Never know where you will find inspiration.

Expand full comment

❤️

Expand full comment

To answer your questions:

1. All the time. It usually means I needed to find a therapist for a patient or look up a book or supplement that a patient was telling me about. It also means that my notebook was not around at the time, although I have notes in there that I also do not understand.

2. We outsource our agony to a professional. I'm an employee while my spouse is self-employed. We need all the write-offs we can get. Unfortunately, last year, most of our write-offs were medical expenses because the US Healthcare system is a massive scam, and insurance companies are shady AF.

3. April is my birthday month, which I use as an excuse to buy myself presents all month. So, yes, I love April.

4. Taxman by The Beatles and Money by Pink Floyd.

Expand full comment

Sorry to hear about this year's medical deductions. It is bonkers how much of a scam healthcare in the U.S. is, and while it offers some relief to be able to write some things off, it also sorta feels like the healthcare mess is joining forces with the tax mess.

But let's focus on the positives, OK? Happy birthday month, Emily!

Expand full comment

May be stretching a bit, but one could argue Exile in Main St album was inspired by taxes (and other things).

Expand full comment

It’s a good stretch. Here are two more. It took George Carlin about 20 years of standup to pay off a big tax debt from his cocaine days. Also, Wesley Snipes post-prison was making films to pay the tax man.

Expand full comment

you may want to add " tumbling dice"

to that album

Expand full comment

1. No. Are you Guy Pearce in Memento?

2. Neither. I approach it as a text-based game.

3. Except for pollen, I like April. I do my taxes in February and March (waiting stresses me out).

4. Taxman, Lennon/McCartney.

Expand full comment

As far as I know I’m not Guy Pearce in Memento, but like him I do try to take things one moment at a time.

Expand full comment

Sorry Michael - I’m having a grumpy old guy day

Expand full comment

No worries. You didn't offend me, so whatever grumpy old guy thing you got going, it's all good! Shine on, you grumpy old guy!

Expand full comment

Thanks. You reminded me of what my mom used to say: “You wanna be miserable, fine. As long as it makes you happy.”

Expand full comment

Past Me used to have a habit of writing then-Future Me notes that now-also-Past Me found to be cryptic and entirely unhelpful, other than inducing the kind of anxiety you so well described today. Then-Future-but-now-also-Past Me had an epiphany and made a solemn vow to all Future Mes ... “Dude, I gotta write clearer notes. Embrace elaboration ... anything less will leave Future Present You twisting in the wind.” Sometimes, Past Me even remembered the solemn vow. Sometimes.

I also embraced tax professionals (figuratively, as literally might be awkward for all parties involved) once I moved past the single-EZ phase of life. Having run afoul of the IRS in my college years after starting (and failing) a small business with a buddy, I developed a healthy terror of screwing up my taxes and decided anything more complicated than “you made X, so you pay Y” was better left in the hands of a professional. Marriage, kids, homeownership, and another small business make (doing) taxes (competently and comfortably) way out of my skill set. Expensive? A little. As the old credit card commercial went ... Peace of mind: Priceless.

As my dad used to say, we have four seasons around these parts: Winter, Mud Season, Black Fly Season, and August. April is the month that tries to throw all four options at once ... catch! Baseball begins for real in April and I’ve been coaching various levels for not quite 20 years ... everything from t-ball to high school. In the last few Aprils we’ve had rainouts, snow outs, 85° and sunburns (everybody forgot sunscreen??!), 39° in drizzle (three more layers ... if I only had on three more layers I’d be not-freezing ... I don’t even need to be warm ... just ... not ... [flashes a series of signs indicating a steal] freaking freezing) ... gorgeous 65° days with a cancellation because “they still have snow in left field” ... and everything in between. [Swats at black flies buzzing around my head.]. But, it’s great ... not late-September/early-October the-leaves-are-turning-the-air-is-crisp-baseball-playoffs-football-started-the-kids-are-excited-about-the-new-school-year great ... but, great all the same.

Taxman - The Beatles.

Expand full comment

Your comment reminds me of covering sports for my college newspaper. I mostly covered baseball and softball. As a Californian, I always thought of spring as a subtle change to longer days and zero chance of rain. But I went to college in New England. I covered games where we'd get a flurry of snow, then a game the next day where it would be 80 degrees. It was so weird to me, but everyone assured that this was normal.

Expand full comment

Big time. I’m in northern NH ... if we waited for perfect baseball weather the school year would be over. 😄

Expand full comment

I also did a small business and eventually got audited on taxes. The takeaway from that was they are not that scary if you have receipts. And even if they determine you messed up, you just have to pay the difference in taxes that you owe plus compounding. If it's not too huge, no penalties involved. You can also set up an installment plan like a car loan, except you're not allowed to miss payments on them.

Expand full comment

reading entrails and vision quests to determine quarterly tax payments has been around for centurys

and hypnosis im guessing CAN be written off

as a business expense but really just another perk if it can convince an April fan base like say the Arizona Diamondbacks

they have a legitimate shot at a wild card

and i dont give a damn if there are

12 in each conference

Expand full comment

It’ll take every ounce of magical thinking we can muster to convince the fans that the Diamondbacks have a chance.

Expand full comment

I studied 'The Waste Land' for my English A level when I was seventeen. Had it even TOUCHED on taxes and personal finance I would have considered myself way better financially educated than I actually ever became - I didn't learn to budget until I was 46 years old, and Eliot could have saved me DECADES of trauma had he ACTUALLY written about taxes!!! 🤣

Expand full comment

Haha! I wish the The Waste Land had actually taught some financial lessons. Or, maybe I just wish those lesson were taught somewhere during my teen years. That would’ve been great!

Expand full comment

Yeah, I missed out entirely on that kind of life learning too, sadly! I'm happy to say that the first Covid lockdown gave me the time and headspace to finally educate myself on personal finance matters - YouTube and budgeting bloggers taught me a tonne! Shame I left it so long, but better late than never. 😊

Expand full comment

Way to find a silver lining, though!

Expand full comment

For a while, we had a tax person do our taxes. Audited only once, and it was the IRS’ mistake. Then I figured I get the same headache whether I answer a tax person’s questions or do it myself, and so started an annual TurboTax addiction. Fortunately California has caught TT’s mistakes and returned more money to me. I do pay a bookkeeper a monthly fee just so I don’t have to deal with Quickbooks or balance business accounts myself. This year taxes were easier by ditching TT for FreeTaxUSA or whatever the IRS recommended. Maybe I should ask our governor to have California do our state returns, since they already know, too?

Expand full comment

It must've felt gratifying for an audit to reveal that it was the IRS that made the mistake. Did you celebrate, or just move on with your life?

Expand full comment

I cashed that check so fast, I scared the zeroes.

Expand full comment

YES!

Expand full comment

Friday Jen once left a note for Monday Jen to “call Judy,” only Monday Jen didn’t know who Judy was or why to call her. 🤦‍♀️

Expand full comment

What did Monday Jen do?

Expand full comment

I did nothing! What could I do? I literally had no idea. Judy wasn't a client or a friend, and I couldn't think of anything else. And in the future, I never heard from Judy and nobody I worked with ever mentioned a Judy. Maybe Friday Jen already had too much wine when she wrote the note? From that point on I added more details to my notes because Dementia Jen is scary.

Expand full comment

The added details seem like a good strategy. But I'm still hoping that one day Judy comes out of the word work and says, "Why didn't any of these Jens call me?" If she does, please let me know so we can close the loop on this note!

Expand full comment

I believe tax returns are not due this year until October. They extended it this year. (I did mine 6 weeks ago.)

Expand full comment

That's correct! There's an automatic extension for Californians because of this year's flooding, and I think some other states are automatically extended too for different reasons. But I'm just happy to have them over with for this year.

Expand full comment

The notes I don't understand were usually punchlines I'd written down and couldn't remember the setup. Outsourced tax stuff is still agonizing. And it has the additional agony of having to pay for it in addition to whatever the government wants. BTW, I looked online and the $600 is only for certain kinds of 1099 forms. Some types are issued for any amount. https://blog.tax1099.com/1099-reporting-requirements/ I'm waiting for some politician to run on a platform of a flat 10% tax. "Tithing -- If it's good enough for God, It's good enough for the government."

Expand full comment

That platform would be pretty popular. There's always a flat tax candidate in the primaries, but I'm kinda surprised we haven't seen one of them link it to tithing. That's a messaging strategy that could work.

Expand full comment

1. Forget the notes, I can’t read my handwriting. I have an essential tremor in my right hand. It truly sucks when I put on makeup. Glad I have a steady left hand. I should have been a doctor. I’d write unreadable prescriptions with the best of them.

2. We outsource but it’s still agony.

3. Passover and my sister’s and kids’ birthday. April is otherwise glorious.

4. I first wrote 44. This is what happens when I text with ET. There needs to be more Rom Coms with a sexy scene of a couple doing their taxes. Together they have a big deduction.

Expand full comment

Honestly, I'm surprised we haven't seen a rom com about two people getting married for tax reasons, then getting audited, then falling in love for real. It's silly, but given the way our tax code generally favors marriage, I'm sure there are couples that might've gone either way on marriage, but then looked at their taxes and figured, why not? So yeah, there really needs to be a tax-driven rom com.

Expand full comment

"Green Card" meets "The Proposal" but with taxes. And a creepy IRS guy is the antagonist.

Expand full comment

Yes!

Expand full comment

As long as nobody from the IRS is reading this, my method is to start looking for 1099s and my lonely W2 in February. I also buy TurboTax as soon as I find it on sale which Intuit has figured out, so they have small sales earlier and earlier each year. As soon as I can, I do the first pass with whatever paperwork I have on hand. This number usually shocks me and sends me into the pit of anxiety. Then in early April (which I define as the night of the 14th), I scramble around to enter the late paperwork and file. In the old days, I’d mail a check, safe in the knowledge that it would take weeks for it to get back to my bank. Nowadays, they just grab the money immediately out of my account which always hurts.

Obviously, my goal is to owe just enough that there isn’t a penalty so that I can keep MY money as long as possible. I never want a refund because that means I gave them too much during the year.

Don’t forget, the IRS is only doing what Congress and the President tells them to do in the least efficient manner possible. Vote the bastards out!

Expand full comment

Good reminder re: Congress and the President. Taxes, and especially tax administration, is a mess of our own making.

Expand full comment