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A Taxing Discussion

Taxes are annoying and confusing, aren’t they? Turns out they were also confusing way back when they were first introduced, too. Let’s talk about the 1040.

By Ernie SmithApril 18, 2026
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#taxes #tax forms #irs #internal revenue service #form 1040 #war revenue act #pay as you go #income tax #e-file #turbotax
Today in Tedium: There's a common motif that often appears in Tedium pieces, the idea that the advent of World War II helped to forge something new and important. Whether it was walkie-talkies, instant mashed potatoes, transistors, or magnetic tape, it was a turning point for numerous industries. It also was the genesis for the most annoying thing many Americans have to do each year: their taxes. As the federal government needed additional revenue, millions of people found themselves paying income taxes for the first time, an example of a practice for rich people trickling down to the masses. What did that feel like? It was a question that came to mind after I found a particularly interesting guide from the period. Today's Tedium ponders the moment when the 1040 entered our lives. — Ernie @ Tedium

Today’s GIF comes from “The New Spirit,” a 1942 propaganda film by Disney to encourage people to pay their income taxes. It starred Donald Duck, who avoided the tax evasion charges that led to Daffy Duck’s arrest.

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“The Congress shall have power to lay and collect taxes on incomes, from whatever source derived, without apportionment among the several States, and without regard to any census or enumeration.”

— The text of the Sixteenth Amendment, which gives the U.S. government the right to collect income tax. It was passed into law in 1909, with the amendment taking effect in 1913—which happens to be the first year of Form 1040. However, in practice, most people did not have to pay initially, because of minimum-income rules that ensured taxes largely targeted business owners and those with large incomes. The regular-person tax bills came later.

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The very first Form 1040, dating to 1913. A variation of this is still available on the IRS website, in case you have any unpaid taxes from 113 years ago. (via National Archives)

What was it like filing your taxes in 1914?

No surprise, I know, but it’s worth noting that the U.S. has a complicated tax history, befitting its start as a war-length complaint about taxes. Initially introduced to help fund the U.S. Civil War, it charged everyone who made more than $600 (roughly $20,000 in today’s money) a tax. The problem was, the U.S. government introduced this income tax without having jurisdiction under the U.S. constitution to do so.

That proved a problem in 1895, when a Supreme Court ruling, Pollock v. Farmers’ Loan and Trust Company, found direct taxes unconstitutional using some pretty harsh language (my emphasis added):

A tax upon income derived from the interest of bonds issued by a municipal corporation is a tax upon the power of the State and its instrumentalities to borrow money, and is consequently repugnant to the Constitution of the United States.

In that case, Charles Pollock sued the company, which he owned a handful of shares in, to prevent them from paying corporate taxes, as required by the Wilson–Gorman Tariff Act, passed the prior year. The case effectively prevented the U.S. government from taxing individuals for nearly 20 years, the amount of time it took to pass the Sixteenth Amendment.

Soon after, the federal government brought back the income tax, this time with the Form 1040. So, in January 1914, you’d be forgiven if you were a well-off professional and were suddenly paying taxes on your income for the first time in your adult life. On top of everything else, it was simply a confusing task.

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One might argue that the reason we have Forbes today is that the income tax suddenly made B.C. Forbes’ job really important, enough so that he launched his own magazine.

You could sense the dread dripping from newspapers and magazines throughout the U.S. as journalists got their first look at the form that would frustrate millions in the years to come. In a 1913 edition of Hearst’s New York American, financial editor B.C. Forbes (who would go on to found a well-known magazine four years later) emphasized how critical it was to get this form and fill it out. But he also emphasized what might happen if you decided to get lazy:

But, for any sake, do not try to hide anything. Don’t do it! If you are not moved by patriotism or a law-abiding spirit to pay your just share towards the support of the Government, be moved by fear!

But don’t pay one cent the Government is not absolutely entitled to. It is as immoral to cheat yourself as to cheat the government. And once you pay, you stand little chance of getting anything back. “Possession is nine-tenths of the law,” you know. The penalties for not complying with the law range from a $20 fine to a $1,000 fine and a year’s imprisonment plus the costs of prosecution. So beware!

Take the matter in hand the minute you read this. There is no time to lose.

One might argue that this tension was good for media outlets who suddenly were in a position to explain all this stuff for normies. For example, The New York Times (see my NYT policy) shared a giant reader Q&A with questions about the new form. It leaned into the significant confusion caused by the new form, which only covered taxation after March 1, 1913—about a month after the Sixteenth Amendment was ratified—but still included blanks for January and February.

“What many critics are unable to understand is why blanks for this year should not have been prepared with the correct amounts, in order to save perplexity to those who attempt to fill them out on only a casual examination,” the paper wrote.

(The initial form was reused in 1914 and 1915—something I learned when I scoured the IRS website and found tax forms dating to 1913—but in future years, the form got updated annually.)

Not helping was that the Treasury Department kept changing its mind on the rules, which made the accounting difficult to manage. From reading the many answers the Times gave to curious readers, it’s clear that the IRS left a lot of people out on the deep end.

However, it did not leave everyone, as initial rules only required people who made more than $3,000 to actually file taxes, an amount equivalent to about $100,000 today. Which meant that most people weren’t affected by income taxes at first. But the people who were taxed, especially at the high end, soon found themselves giving most of their money to the government.

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The New Man on the Job, an editorial cartoon by John Scott Chubb from 1913, which only picked up relevance as World War I briefly pushed tax rates for the ultra-wealthy above 75%. (Library of Congress/public domain)

In the midst of World War I, tax rates for people who made over $300,000 in 1917 ($8.4 million today) crossed the 50% mark, while people who made more than $1 million in 1918 ($23 million today) were taxed at a downright epic 77%. Things didn’t truly ease up until the mid-1920s, when taxes were capped at 25% for people making over $100,000 ($1.9 million today). Critics of taxes, such as the Koch-affiliated Foundation for Economic Education, often point to this period to highlight the folly of increasing taxes on the rich.

For critics of the American taxation system (think your average Ron Paul acolyte), this era offers so much fodder to dig into, because it offers examples of many of their complaints. (Though they’re kind of stuck with the Sixteenth Amendment.) You say, “we should increase taxes on the rich,” and they can say, “well, we did that, and it didn’t work.”

But one thing we didn’t try back then was taxing regular people who made normal salaries. That came later.

“I guess you will have to go to jail. If that is the result of not understanding the income tax law, I shall meet you there. We will have a merry, merry time, for all of our friends will be there. It will be an intellectual center, for no one understands the income tax law except persons who have not sufficient intelligence to understand the questions that arise under it.”

— Elihu Root, a senator and former Secretary of State, stating to a friend what he thought of the then-emerging taxation system ahead of the Form 1040’s debut. Root’s comments, highlighted during a 1955 presentation on taxation at William and Mary and repeated numerous times by taxation critics in the years since, point at the tension that taxes have always had. They’re confusing and easy to screw up, yet we have to do them anyway.

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An example of an IRS TeleFile worksheet from 1992. As complex as taxes are, could you imagine trying to do this over the phone? (Internet Archive)

Five key moments in the history of taxes

  1. The IRS introduced the charitable deduction early in the 1040’s history. One positive of the era when the government was taxing millionaires three-quarters of their salary was that it gave rise to the charitable deduction, which led to a huge culture of philanthropy. First introduced as an amendment to the War Revenue Act of 1917 by New Hampshire Sen. Henry F. Hollis, the bill was essentially a way to support civil society. As Travis LaCouter wrote in Philanthropy Daily in 2017, this helped support organizations like the Red Cross, which grew in public prominence during this period.
  2. The IRS was early to database-based tech—but updating was impossible. The creation of the Individual Master File, the electronic backend system used by the IRS for more than 50 years, was an important step for the IRS, but one it’s struggled to improve on. Built on COBOL and assembly language, this system has proven surprisingly difficult to kill, even as attempts were made to modernize it starting in the early 2000s. A 2023 Government Accountability Office report found that the IRS may not be able to fully upgrade it until 2030. For now, it remains a giant security risk.
  3. The IRS was testing electronic filing as early as 1986. Early pilots of the e-file program, which initially emphasized tax professionals, launched in 1986 and expanded nationally by 1990. By the late ’90s, the e-file program became an option for regular consumers too, but before that they also had a more novel option: TeleFile, a file-by-phone program the IRS offered starting in 1992.
  4. The IRS helped popularize the PDF. As noted in our piece on the history of the portable document format, one of the first major users of Adobe’s ubiquitous tool was the Internal Revenue Service. The IRS saw an opportunity to cut down on the hundreds of millions of forms it sent to taxpayers. It was already distributing tax forms using the technology as early as 1994. The IRS is very serious about its PDFs, as proven by the fact that you can find 1040s on its website dating all the way back to 1913.
  5. The IRS is now an electronic-only payment platform. It’s been possible to get refunds from the government electronically for decades, but now it’s mandatory in nearly all cases. Last year, the Trump administration introduced Executive Order 14247, “Modernizing Payments to and From America’s Bank Account,” which requires the service to pay people through electronic means such as ACH, rather than with paper checks.
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If you were doing taxes for the first time in the 1940s, odds are you ran into a guide like this.

World War I briefly led to huge taxes for rich people. World War II forced regular people to do taxes, too.

I became interested in this discussion on income taxes because of a magazine-length guide I found in a junk store. It explained in great detail how tax forms worked, considerations for families and the public alike, even showing tax forms and offering basic accounting advice.

It promised 500 questions and answers, and seemed designed to take one of the most confusing things that normal people do and make it accessible. It included workbooks designed to make it easier to track your monthly income.

(It also smelled pretty bad, but we can overlook that.)

This was one of the most well-known guides of its kind at the time, originally written by Rodman L. Modra, who served as deputy collector of internal revenue in New York City earlier in his career. His guide was widely promoted in newspapers around the country; you could call it the For Dummies or even the Turbotax of its day.

Modra found quick success with this model, but he didn’t live to see his good idea blossom into an empire. Just as the income tax was expanding its footprint in 1943, Modra died (yes, another NYT link, same policy applies). He was 61, and presumably, he had more steam in the engine. Alas.

So yes, the guide outlived him, at least for a while. But it didn’t last as long as the income tax system it was chronicling for regular people. Other companies would eventually exploit our required annual stress-out session.

Again, Disney made a cartoon in 1942 to convince people to pay their taxes.

So, what made a guide like this particularly relevant in the mid-1940s? Well, in 1942, Congress passed a new tax law, the Revenue Act of 1942, that essentially lowered the tax brackets a rung. Now regular people had to file a 1040, too.

This was necessary, after all. World Wars are expensive, and someone needed to pay for it, so why not the middle class?

And as more people needed to file their taxes, the Internal Revenue Service needed a new way to take a little off the top. In the past, people paid either quarterly or annually, which worked when everyone was well-off, but not so much for the middle class. As tax historian Joseph Thorndike wrote in 2022: “This system functioned well enough when income taxes were paid only by the rich, who tended to be well organized and financially sophisticated. But tax experts worried that it would falter once the levy was expanded to include millions of new taxpayers.”

The solution to this situation wasn’t necessarily clear. Businesses pushed for a national sales tax; the Treasury Department really didn’t want that.

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Beardsley Ruml, the man who convinced Congress to let the federal government take money from your paycheck. Blame him, or credit him, up to you. (Rockefeller Archive Center)

The guy most responsible for helping us find a path forward was Macy’s executive and economist Beardsley Ruml. His plan: Make the system “pay as you go.” Rather than having to save your income ahead of time and paying after the fact—or worse, get stuck in a repayment plan with the Internal Revenue Service—Ruml instead proposed closing the loop entirely.

“Nothing can stop the march of the days and when the due date comes, they must pay the tax they owe in the income they have already had,” Ruml explained in an article to the Dartmouth alumni magazine.

In a 1943 interview with CBS News, he characterized the back-taxes issue as something of a failure of vision.

When the federal income tax bill was passed in this country in 1913, it had an important defect which was that a citizen was required to pay in the year 1914 a tax on his 1913 income. In this way, we got started on a vicious practice of paying out of one year’s income a tax on the year that had already gone. As a result and in consequence of increasing rates, the debt which people owe to the federal government for income tax has become a national danger. The present system is a bad system for all of us and should and can be corrected. It is clear that the government cannot continue for long to be the creditor of some 27,000,000 taxpayers and their families, in debt for income tax as they are today, particularly when there is no substantial question of revenue involved in changing the basis of assessment and getting the whole country on a current pay as you go basis.

In this light, paying as you go made sense. You could pay as you go with payroll taxes, or you could give a penny or two to the federal government every time you bought something. A wire story about the debate over this issue in the House Ways and Means Committee put it like this: “Shall the average American help pay for the war by taxes on what he earns or on what he spends?”

Ultimately, after a whole bunch of back and forth, collected in this PDF, we went with the payroll taxes, with Congress passing the Current Tax Payment Act in 1943. (Easing the pain, per Tax Notes: The first year of the payroll tax transition, the federal government cut everyone’s taxes by 75% for the first year, like you were signing up for an introductory plan on a steak-of-the-month club. Not that people who just saw a huge chunk of their income disappear were buying steak.)

If you’re a freelancer, odds are good you might still be doing quarterly or annual payments, minus whatever deductions you can scrounge. But hey, it covered most people, as it does today.

The tax model is confusing and unpopular, but pay-as-you-go taxation at least made it more user-friendly.

Going back to this weird tax book I found, of the many things it covers, perhaps the one that stuck with me the most is the emphasis that yes, it is possible to do this yourself:

Even if you are not used to working with figures, there is nothing really difficult about preparing your income tax blank. If you know how to add, subtract and multiply and have just enough patience to stick to the job for the short time it takes—you will be surprised to find how easy it actually is. The new 1944 return is much simpler than last year’s and no one should hesitate to fill out his own tax blank.

This book describes the specific tax policies that people working in various lines of work need to know. Actors are included. So are clergymen. And mechanics. It’s having to cover a lot of bases, but it’s covering them without being too judgmental about your lack of tax knowledge.

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Ever wonder what an income tax form looked like in 1944? Here you go. (Would you be able to fill one out with pen and paper today?)

That is a different vibe than what we’ve come to expect from the modern tax apparatus, which tends to emphasize that you need additional tools to complete your taxes. TurboTax and H&R Block exist because someone needs to ensure you’re not screwing this up. This book doesn’t have any tech behind it. It just has the insights of a knowledgeable tax expert (or at least the team of people who succeeded him).

Even with gradual changes over time—deductions are pretty nuanced these days—this book still describes something recognizable. That said, the odds that people are completing their taxes with paper and pen have declined significantly over the past 30 years or so.

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TurboTax: You’ll never be rid of us. (Focal Foto/Flickr)

If you were presented the worksheets for doing your taxes by hand in 2026, could you do it? Would you give up? And would you be more likely to screw it up with your grubby scribbles all over the page, versus the never-ending forms of TurboTax?

In recent years, ProPublica has done an impressive job of publicly embarrassing TurboTax for essentially tricking people into thinking the service is free, when it’s not. It may be one of the best reporting campaigns against a single company in the history of journalism. And it likely created momentum for a direct-file process that could be completed for absolutely free.

Intuit and H&R Block have better lobbyists, however, and they were able to end the program soon after Trump took office. Elizabeth Warren’s attempt to revive the initiative in Congress tanked this week.

But there was once a time when the federal government attempted to make taxes easier to do, not harder, and that came in the form of the “pay as you go” plan. Beardsley Ruml was onto something.

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Find this one an interesting read? Share it with a pal! And may this be the last bit of tax-related content you see this year.

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Ernie Smith Your time was wasted by … Ernie Smith Ernie Smith is the editor of Tedium, and an active internet snarker. Between his many internet side projects, he finds time to hang out with his wife Cat, who's funnier than he is.