99% Invisible - I've Got 1099 Problems...

Episode Date: April 15, 2025

If you're one of the millions of Americans struggling with your tax forms today, you're not alone. Even Albert Einstein allegedly found income taxes to be "the hardest thing in the world to understand." But how did our tax system become so complicated?I've Got 1099 Problems... Subscribe to SiriusXM Podcasts+ to listen to new episodes of 99% Invisible ad-free and get exclusive access to bonus episodes. Start a free trial now on Apple Podcasts or by visiting siriusxm.com/podcastsplus.

This is 99% Invisible. I'm Roman Mars. On a hot summer day in 1799, French Army engineers in occupied northern Egypt were sifting through the rubble of a centuries-old abandoned fortress. These soldiers had been tasked by their general, Napoleon Bonaparte, heard of him? To repair the fort for proper use. And as they were laying the foundation for the walls and barracks, someone made a startling discovery. That's producer Vivian Ley. They stumbled upon the Rosetta Stone, possibly the most famous chunk of rock in human history.

The reason it's famous and the reason you can see it when you go to the British Museum is that there was text in three languages. That's Joel Slemrod, professor of economics at the University of Michigan. The text on the Rosetta Stone had been inscribed with the same message in three different scripts — Greek, Egyptian Demotic Scripts, and Ancient Egyptian Hieroglyphics. Which at the time no one could decipher. Based on the first two scripts, researchers were eventually able to crack the code for how to finally read hieroglyphics, a writing system that hadn't been used for about 1,400

years. Question, what was so important to write about? And the answer is, well, among other things, the Rosetta Stone describes a tax break given to the temple priests of ancient Egypt. So the Rosetta Stone helped us unlock the secret of hieroglyphics by talking about something in Texas. Taxes are essentially as old as human civilization, and they've been shaping it ever since. Historically, they've influenced everything from what our buildings look like, to what

kind of cars we drive, to who we elect as our president, to whether we revolt. History has shown that tax codes can reveal so much about a society. And if you're an American, the revelation is that filing our income taxes sucks. If you're listening to this episode on its release day, it is April 15th, aka tax day here in the United States. And we Americans tend to have a pretty fraught relationship with our tax system. The filing process has become so complicated that the average individual spends 13 hours

preparing their income taxes. And that can feel twice as long when you want to put your fist through the computer screen the entire time. 53% of Americans are very bothered by the complexity of our tax system. And one survey even reported that it makes one in three people, quote, want to cry. Even Albert Einstein allegedly once said, the hardest thing in the world is to understand the income tax. And he was famously smart. So on this the final day of tax season, we are sifting through nearly 250 years of US tax history to figure out

how things got so damn complicated. Being mad about taxes is a quintessentially American experience. In fact, tax rage is a large reason why this country was created. The Boston Tea Party, a formative event in the American Revolution. Most of us learned in middle school that the Boston Tea Party was an act of defiance over an increase in taxes on tea. But fun fact, that's totally wrong. Actually though, that isn't what happened.

Closer to the truth was that some tax on tea had been decreased. At the time, Britain had been taxing tea at such a high rate that nearly two-thirds of tea imported to the colonies was smuggled in illegally to get around the cost. In response, Parliament actually lowered taxes on legally imported tea to undercut this illicit tea trade. The new proposals from the British looked like they were going to deprive some prominent patriots of their livelihood through smuggling tea.

And it got a lot of people upset. That upset eventually led to the American Revolution and the founding of an entirely new country. Given that tax overreach was a huge contributing factor to the revolution, the early American government was very cautious when it came to taxation. It remained very low and extremely simple. And for many, many decades, federal revenue came mainly from things like excise taxes and tariffs.

For clarity, excise taxes are applied to certain goods and services, like fuel. And if you don't know what a tariff is, well then, bless your heart, you clearly haven't been looking at the news. In those early years of the republic, federal spending was low enough that the country could fund itself like this. Until suddenly it needed a lot more money. And fast. During the Civil War, like all wars, a lot of revenue was needed.

In 1862, President Lincoln signed into law an income tax to fund the war. This was actually the very first federal income tax in US history, and even led to the creation of the IRS, then called the Bureau of Internal Revenue. The income tax generated $55 million for the Union government, which was the equivalent of about $1.1 billion today. It was an innovative approach to raise federal funds. Maybe a little too innovative for its time.

Sure enough, when the war ended, I think, 1872, that income tax was eliminated. With the Civil War behind them, kind of, the Grant administration repealed most emergency taxes and reverted back to the old way of tax collection, excise taxes, with a special focus on what were called SIN taxes. 90% of all federal revenue came from taxes on liquor, beer, wine, and tobacco. Although the income tax was effective, leaders remained resistant to the idea.

Excise taxes seemed adequate to fund the government, plus they were a lot simpler to implement. They were simpler, but a lot of people thought they were very unfair. Excise taxes are regressive, meaning they place a higher burden on lower-income individuals. If someone who makes very little money is paying the same rate as someone who makes a lot of money, then they are paying a higher percentage of their income. And most people would view that as patently unfair. So years go on, and there were a lot of people who were not happy with the fact that most of the revenue is coming from taxes on liquor, beer, wine, tobacco, and probably the burden was felt heavily by lower income people.

So picking up in the 80s, that's the 1880s, and especially the 90s, there was a lot of political support for instituting an income tax and therefore reducing these other taxes. This was all taking place during the Gilded Age, an era of profound wealth inequality and exploitation of the labor class. The tax burden was mainly shouldered by the vast majority living in extreme poverty. Meanwhile, robber barons were living in luxury and rubbing elbows with Christine Boranski.

So in 1894, against the odds, Congress passed the Wilson-Gorman Tariff Act, which instituted the first-ever peacetime income tax. This tax specifically applied to the rich and only applied to anyone making over $4,000, which at the time was the highest earning 1% of the population. It also lowered tariffs on imports, making them cheaper. So the law was very popular with the pro-free trade wing of the Democratic Party. But unpopular with the Supreme Court.

The Supreme Court had ruled that an income tax was unconstitutional because, you know, richer states, the tax burden would be higher than poorer states. So on that basis, it was ruled unconstitutional, even though it wasn't clear during the Constitutional Convention what a direct tax was, and still isn't entirely clear what was meant. Okay, so it's unconstitutional. And so how do you make a federal income tax not unconstitutional? You change the constitution. The income tax slowly made its way through the ratification process until finally in

1913, it was solidified by the 16th Amendment. And the 16th Amendment basically says the federal government has the right to levy an income tax even though the revenues collected would not be proportional to population. The national income tax opened up the federal government to a whole new source of income and was a huge change for people filing an income tax for the first time. But barely anyone had to file one. The exemption level was so high that it was actually thought of as a class tax, not a mass tax, because it applied to so few people.

So in 1913, the exemption level was $3,000. Okay, that's about $90,000 in today's dollars, approximately. So in 1913, about 350,000 returns were filed. And that's in a country with a population just under 100 million. Not only did the income tax only impact a narrow fraction of the population, the paperwork involved was wonderfully uncomplicated. As a tax nerd, you won't be surprised to know I have a copy of the original tax form framed in my office.

The filing form of the new income tax was, and this is the form and the instructions, four pages long. Despite how sparse the four-page form was, by the following year, some were already decrying its complexity. At the annual conference on taxation, one speaker declared, It will hardly be denied that the federal income tax needs simplification.

Its complexity is its distinguishing characteristic. To begin with, the language in which the act is couched is involved, and its rhetoric bewildering. Its terminology is confusing. But of course, in terms of complexity, it was only uphill from there. And just a few decades later, the U.S. reached an inflection point that changed the income tax for good. Yesterday, December 7th, 1941, a date which will live in infamy. So as we're talking, it's clear that wars play a big part in the story of taxation. It changed very precipitously in World War II.

The sheer scale of the war meant that Americans would be taxed like never before. For one, the exemption level for filing taxes was lowered way down, meaning a lot more of the population actually had to deal with it. In 1939, 7.7 million returns were filed, okay? Six years later, 49.9 million. So that's an increase of more than six times. So that was the big change.

It officially went from being a class tax to a mass tax. And the Department of Treasury plugged it as our patriotic duty to the war effort to file our taxes. They even commissioned Irving Berlin to compose a jaunty little number about it. I'm squared up with the USA. You see those bombers in the sky. Rockefeller helped to build them, so did I. I paid my income tax today.

I paid my income tax today. And it wasn't just the tax base that evolved during this time. The way we collected them changed as well. Before 1943, individuals filed once a year for the one lump sum that they owed. Ideally, taxpayers would plan ahead and save enough all year in order to file and pay their taxes in the spring. But 1943, the federal government changed the rules. It said, no, now the employers have to be sending money to the government while you're earning it.

If you earn a living as an employee of a business or a corporation or a government agency, you know, you report to the man, then you are already fully aware of employer withholding. Your employer is required by law to withhold a portion of your wages to pay into taxes you owe. That was a major change in how the income tax system worked. This modernized tax collection in some very important ways. For one, most citizens stopped being slammed by a larger tax bill once a year, since they were already paying into it incrementally through their paychecks. Also, there were fewer people to shake down.

It makes the administrative burden and the burden on the IRS much lower. They don't have to track down all the employees. But history shows that this has been the biggest innovation in how tax systems work. Almost every country of the world with an income tax does this. When World War II ended and government spending declined, you might have expected the income tax to be abolished once again, like what happened after the Civil War. But instead, it just stuck around. The level of tax didn't decline precipitously after World War II, sometimes called the ratchet

effect. And, you know, why that happened is not entirely known. You know, one story is that people had become familiar with it. The government had gotten good at it during World War II, and so it stuck around and has stuck around since then. During the war, the role of the federal government had permanently expanded in a way that made going back to the old tax structure impossible. Government spending had ramped up from increased Social Security to the GI bill to defense

spending. So it's just been a huge increase in the amount of money collected and spent. After World War II, up to the 50s and early 60s, the top rate of income tax in the US and in the UK was over 90%. Vivian, I don't know if you're a fan of popular music, but the Beatles had a song, The Taxman, right? It's one for you, 19 for me, I'm the taxman. So that's a 95% rate. World War II made filing income taxes nearly every American's problem.

But there were two big reasons why filing taxes became a much more complicated problem. One reason is that after World War II, policymakers more and more started using the tax code to socially engineer taxpayer behavior. There's no question that the tax system can affect behavior, and legislators have noticed this, and there's a lot of things in the tax system,

which are there not particularly to make the tax system fairer, but to change people's behavior. Using tax law to drive behavior was not new or unique to the United States. In fact, historically, it's been used in some kind of bizarre ways. In Russia, Peter the Great, when he was modernizing Russia to look more like Western Europe, he noticed that the nobility in Russia had these full beards in Western Europe. That was kind of out.

And so what did he do? He could have banned beards, you know, having a beard, but instead he cleverly had a tax on beards. So if you were out in public with a beard, you had to have a little medallion that was proof that you'd paid your beard tax. In post-World War II America, the income tax now applied to so many more people that it became a useful tool for lawmakers to nudge the masses into certain socially beneficial behaviors. Tax credits can encourage you to save for retirement, or discourage you from buying a gas-powered vehicle, or encourage you to renovate a historic building, or discourage you from buying a gas powered vehicle or encourage you to renovate a historic building or discourage you from buying tobacco and alcohol.

Another big reason why the income tax code has become so complex is ironically for a very simple reason because we want it to be fair. Our tax system, any tax system could be made much simpler, but the issues in deciding how much simpler, I think, are best illustrated by talking about what's the simplest tax system you can think of. The simplest tax system I can think of is what economists call a lump sum tax. A lump sum tax is basically the same flat monetary amount owed by every person, regardless of how much they make. It would be darn simple. Why would this never happen?

Because most people would find that to be completely unfair that the richest person in America owes exactly the same tax as a single mother struggling to get by. We do not have a lump sum tax here in the United States. We have a progressive tax where our tax rate increases alongside our income. But even that doesn't truly account for fairness. Somebody says, well, that's not enough. Somebody with the same income as somebody else but with a lot of medical expenses, they're not really as well off.

All right, so let's have a deduction for medical expenses. More complicated and dot dot dot. The more we try to fine tune the fairness of the tax system, that inevitably makes it more complicated. This opens the door to a lot of questions like, doesn't a single mother of three deserve a larger tax refund than a single person with no children? Or can you deduct a ransom payment? Or why should a whaling ship captain have to pay the same amount as a sailing hobbyist when it's a business expense?

Whether or not our tax system is actually fair is a whole other story. But we are constantly tinkering with it to account for these unique questions and circumstances It is the eternal struggle for fairness and the resulting credits and deductions and exemptions That has ratcheted our tax code into a labyrinthian experience the form 1040 which started out as four pages in 1913 has become a whopping 106 page document in 2025. Well, I think it could and should be simpler. I think the tendency is too much to try to fine tune the tax system for fairness and

to use the tax system to change behavior and incentivize various things. I think we've gone a little bit too far. So I would take seriously making the tax system simpler than it is now. There have been plenty of attempts to reform our tax code with varying levels of success and policymakers will continue fighting over the best ways to do it until the end of time. The United States has a complex economy that, for the most part, requires complicated tax law.

But just because we have a convoluted tax code doesn't necessarily mean that average Americans need to suffer while navigating it. The government could make the income tax filing process a lot simpler, and in a lot of other countries, that's exactly what happens. So in a lot of countries, most households don't have to file tax returns. Thirty-six countries, including the UK, Spain, Denmark, and Estonia, all have a variation of a system called return-free filing. What happens is, come January or February after the tax year, they get an email from the government and it says,

hey, we've gotten information from your employer and your bank, etc. And based on what we know, here's what your tax return looks like, and here's what you owe. So all we ask you to do is look it over. If we got it all right, you know, click this box and you're done. Of course, the tax code in the United States is long, winding and complex. But there are plenty of other countries with complicated tax codes that have made filing easier and free for taxpayers. In the U.S., the IRS already has a lot of the information needed to prepopulate our tax forms for us, which could save us a ton of time and money. That sounds like a pretty important simplification in the tax filing system.

And you can guess who doesn't think it's a good idea. It's the makers of tax software. Tax software providers and related special interest groups have a vested interest in keeping tax forms as intricate and intimidating as possible. Filing an income tax without the help of a professional is daunting. A 2024 survey indicated that 44 percent of Americans plan to use tax software provided by companies like H&R Block or TurboTax in order to cut through that confusion. The companies that sell tax software do better when the tax system

is complicated because if as it gets complicated you worry you're not doing it right and you worry you're not getting every all the credits and deductions you deserve. ProPublica reported that for decades Intuit, the parent company of TurboTax, has spent tens of millions of dollars lobbying against new tax systems that would have made filing free and easy for average Americans. There's also another cost outside of time and money when it comes to this issue. Filing an income tax return is one of the most common ways that the average American

directly interacts with the federal government. When that interaction is a perpetually bad experience, people lose trust in the government. Despite the resistance, there have been some major moves over the past few years to transform the taxpayer experience. One development in particular has been especially promising. And a new tool is available to make filing your own taxes easier starting this year. Taxpayers have access to something called the IRS Direct File Tool. It's free, user-friendly, the online service allows eligible...

In 2024, the IRS rolled out a direct file pilot program in 12 states, which allowed qualifying taxpayers to file returns electronically for free without the use of commercial tax prep software. Participants were able to file in as little as 30 minutes, and 86% of respondents reported that direct file increased their trust in the IRS. The program has been widely seen as a good start for making taxes a lot simpler and a lot cheaper for a wide swath of Americans.

But unfortunately, it does face an uphill battle. The latest casualties of Elon Musk chainsaw thousands of IRS workers. The layoffs hit roughly 7% of the agency's 100,000-person workforce this week, just as millions of Americans prepare to file their taxes. Although the Treasury Secretary committed to keeping and even expanding the direct file program through the 2025 tax deadline, its long-term future is uncertain. Congressional Republicans and private tax firms have criticized the program as unnecessary

and unsustainable. Elon Musk even posted that he had already, quote, deleted the government agency that worked on the program. So who the hell knows what will happen. And until we know what the hell will happen, every April 15, filing an income tax will continue making me want to cry alongside a third of Americans and Albert Einstein. We're supposed to be doing our taxes right now. Do you have any tips for people who have not done their taxes just yet?

No, I don't. As I said, I'm not a lawyer. I'm an economist. So I guess I don't have any tips for you. Joel Slimrod is a professor of economics at the University of Michigan and the co-author of the book Rebellion Rascals and Revenue Tax Follies and Wisdom Through the Ages. If you're a 99PI fan, I highly suggest you check it out because it is right up your alley. When we come back from the break, Kurt Kohlstedt gives an architectural digest tour of how taxes have shaped the world's buildings. Stay with us. So one of the things we mentioned briefly in Vivian's piece about tax code was that taxation influenced what our buildings look like.

And so I'm here with 99PI's own Kirk Kolstad to talk about that, how the built environment around us was shaped by taxation. Yeah, that's right, Roman. And we tend to think of buildings as being the product of regional styles and architectural designers, and maybe on the more mundane side, things like the availability and cost of certain materials

or of course building codes, but tax code can leave incredible marks on buildings that last for centuries. Okay, give us an example. Well, after the Revolutionary War, Britain was massively in debt. So King George III introduced the British brick tax in 1784 to like raise revenue and pay off those bills,

and of course brick makers, they learned of this, and they saw that they'd be taxed on a per brick basis. And so they responded by simply making bigger bricks. Right. And so with bigger bricks, you can make as big a wall with fewer bricks. And therefore you're sort of, you're paying the same, you know, per unit tax, but you get, you know, a bigger building. More material. Yeah, exactly. Yeah. Yeah. Yeah. That's the idea. But of course, the Crown caught on to this and responded both by increasing the taxes per brick, but also adding a tax

for bricks above a certain size. And this move actually caused some businesses to go under because they couldn't afford the higher taxes. They had all this larger stock on hand and they just couldn't pay that. But a lot of those larger bricks made during that era, made it out into the world and can be seen on buildings to this day. And in some cases, you can even see both the pre-tax

and the post-tax bricks on a single wall. So I just shared you this photo of a high street in England. And maybe you can just describe what you're seeing. Sure. So there's the sign high street. It's a brick wall. And there's a vertical line dividing two parts of the wall. And on one side, the bricks are quite a bit larger

than the other side, the smaller side. There's kind of a mosaic side and the kind of big brick side. Yeah, yeah, totally. And so you can imagine like a historian can literally just look at this and understand that like this part of the wall dates back to this era and this part of the wall,

you know, it dates back to a different era just from looking at the brick sizes. That's so cool. Okay, what else do you have for us? Well, a few years later, British lawmakers introduced a per window tax. Yeah, and if this follows the same logic of the brick tax, you would just have like really big windows,

which I don't think I've seen. No, no, alas no. I imagine that would have been super expensive. And so instead people actually just started boarding or even bricking up the windows that they considered like less important. And even though that tax has like long since been repealed, you can still see windows around the country

that were bricked up in that era. Yeah, because that's something that's easy to do, but that's kind of hard to undo. Right, right. Because then you have to install a window, right? Exactly. Yeah, yeah. And so I imagine that's part of it.

And then in some cases, I could see people just getting used to it, right? Like those areas have become walls over the centuries, and so they've just taken on a completely different use. And those were deemed the least important windows, so that would make sense. Now we've been talking a lot about Britain, but in some places, like Amsterdam,

taxation has really fundamentally shaped the entire character of the city, and I'm specifically referring to those really prominent canal houses for which Amsterdam is really well known. Yeah, these are beautiful. They're like these super thin buildings. They're usually like four,

maybe five stories tall, give or take. And they sit, you know, side by side, like wall to wall along a lot of blocks in canals. And between their narrowness and their crowdedness, I mean, I find them like delightful, like storybook, beautiful. Absolutely. They look like something out of a fairy tale.

And one could argue that they're like the most defining physical feature of Amsterdam. And somebody visiting the city could look around, see like how consistent they are in a certain way, and maybe imagine that there was a master plan to build the whole city like this. Or maybe there are just building codes that say, you have to have this kind of shape or whatever.

But no, it was taxes. Amsterdam chose to tax buildings based on the width of a building's front facade. Wow. And once you know that, it all makes sense because that one tax encouraged people to build exactly what we see today. Really skinny buildings,

pretty tall for a residential place, you know, quite a few stories, and, you know, they're really deep, they go back as far as possible to get the maximum space they can, but with minimum width, so therefore reducing their taxes. Exactly, it's all about the bottom line. And then as a result of this thinness, the interior staircases became really narrow too. And that made it difficult, if not impossible in some cases, to bring furniture up or carry up goods to be like stored on higher levels. So another iconic feature of these buildings

are these hoist and pulley systems that stick out over the sidewalks. And they sit right below like the gabled roof at the very top. And they're very prominent. Right, and these are because, say you got this gigantic couch to move, or a heavy sack of grain or whatever, I don't know. But you just hook a rope on it, and you pull it up,

and then you swing it into an upper know, like into an upper story window. Yeah, yeah, exactly. And some of those have been removed to, you know, in the intervening centuries, but a lot of them are still around and some are purely decorative, but others are still very much in use because it's not like the constraints have changed, right?

They still have these really narrow staircases and people still really need furniture. And if I lived in one of those buildings, I would totally keep the hoist in working order. Oh yeah. I mean, it's really like, it's a kind of iconic part of the building. It's as iconic as the narrowness of the building.

Yeah, and that's what's wild about all of this to me because you've got this beautiful canal city and it draws tourists for this amazing architecture. And you know, it would be easy to imagine that it was planned down to every detail. Like they intended to have these narrow buildings and they intended to have these hoist systems. But like so much of it, like it's all driven by taxation.

Right, and these types of stories like excite you. We have a whole book full of them. It's called 99% Invisible City that Kurt and I co-authored about five years ago at this point. It's like the five-year anniversary. Yeah, it's coming up on that five-year anniversary. And we're going to have some special content around that too, but I'm going to keep that piece a surprise.

Excellent. But in the meantime, you can go check out the 99% Invisible City or just keep listening to the show. We'll talk about this stuff again. As always, we'll keep nerding out about this. 99% Invisible was produced this week by Vivian Ley and edited by Delaney Hall, mixed by Martin Gonzalez, music by Swan Real and APM. Fact-checking by Graham Hayesha. Again, Joel Slemrod's book is called Rebellion Rascals and Revenue Tax Follies and Wisdom Through the Ages. There's a ton of really fun, very 99PI tax stories in there that we didn't get to that

we know you'll love. Oh, this is really important. 99% Invisible is up for three Webby Awards this year, and I'm really feeling the need to win them. We're up for Best Arts and Culture Podcast for the Power Brokers series, Best Arts and Culture episode for Rocketman that was produced by Chris Perube, and Best Limited Series for the Power Brokers series, best arts and culture episode for Rocket Man that was produced by Chris Berube, and best limited series for the Power Brokers series. We'll have a link in the show notes to the Webby Awards, or you can just search for Webby Awards and then search for 99 to get to our categories.

Thank you so much. Kathie Tu is our executive producer, Kurt Kohlstedt is the digital director, the rest of the team includes Chris Berube, Jason DeLeon, Emmett Fitzgerald, Christopher Johnson, Lashma Don, Joe Rosenberg, Kelly Prime, Jacob Medina Gleason, and me, Roman Mars. The 99% visible logo was created by Stefan Lawrence. We are part of the SiriusXM podcast family now headquartered six blocks north in the Pandora building. InBeautiful, Uptown, Oakland, California. You can find us all on Blue Sky as well as our own Discord server, there's a link to that as well as every past episode of 99PI at 99PI.org.