This year marks 250 years of American independence, which also means two-and-a-half centuries of spirited debate over taxes. From the nation’s earliest days, revenue has been raised in inventive, controversial, and occasionally head-scratching ways, often followed closely by creative attempts to avoid it. To mark this anniversary, our annual tax quiz explores the lesser-known, stranger corners of U.S. tax history.
In the 1790s, the federal government imposed a tax that sparked armed resistance in western Pennsylvania. What was the tax actually on?
A. Horse ownership B. Whiskey distillation C. Imported tea D. Playing cards
B – The Whiskey Tax wasn’t aimed at casual drinkers but at distillers, many of whom were small frontier farmers turning grain into shelf-stable income. To them, the tax felt like a coastal money grab, and protests escalated into the Whiskey Rebellion. George Washington personally led troops to put it down, proving two things early on – the federal government would enforce tax laws, and Americans would complain loudly about them.
During the Civil War, Congress briefly experimented with a federal income tax. What was one unexpected thing taxpayers were allowed to deduct?
A. Bribes paid to avoid the draft B. The cost of hired farm labor C. Losses from shipwrecks D. Beard-grooming expenses
C – Shipwreck losses. In an era when commerce moved by sea and river, losing a shipment to a wreck was a real business risk. The government recognized this long before it figured out depreciation schedules or standardized forms. Sadly for the bearded, personal grooming never made the cut.
In the early nineteenth century, tariffs were the federal government’s main revenue source. Which item was once considered so politically dangerous to tax that it helped trigger a constitutional crisis?
A. Wool coats B. Iron nails C. Imported hats D. Cheap British textiles
D – Cheap British textiles. Protective tariffs raised prices on imported cloth to support American manufacturers, but Southern states relied heavily on imports and exports. The resulting tariff fights fueled the Nullification Crisis, where South Carolina flirted with ignoring federal law entirely. It turns out fabric can tear a nation, metaphorically and almost literally.
Before payroll withholding existed, how did many Americans pay their income taxes during World War II?
A. By mailing cash in envelopes B. Through quarterly visits from IRS agents C. In a single painful lump sum D. With war bonds only
C – One lump sum. Taxpayers were expected to save throughout the year and then pay all at once, which went about as well as you’d expect. Withholding was introduced partly to fund the war efficiently and partly to stop widespread shock, confusion, and strongly worded letters to Washington, D.C.
In 1895 the Supreme Court ruled a federal income tax was unconstitutional. What was the main reason?
A. It unfairly targeted farmers B. It violated states’ rights C. It wasn’t apportioned among the states D. Congress forgot to define income
C – Apportionment. The Constitution required certain taxes to be divided among states based on population, not income. The income tax didn’t do that, so it failed on technical grounds. The 16th Amendment later fixed this, proving that sometimes the solution to tax problems is more paperwork at the federal level.
At various points in U.S. history, Congress has taxed purely to change behavior rather than raise money. Which of these was explicitly intended to discourage its use?
A. Colored margarine B. Wooden houses C. Cheap paper D. Public theaters
A – Colored margarine. To protect dairy farmers, from the 1880s to 1950 Congress taxed margarine that was artificially colored to look like butter. The result was grayish margarine and widespread consumer resentment. Eventually, common sense – and better food science – prevailed.
How Did You Score?
5 – 6 correct: You could probably audit the 18th century. Historians salute you, accountants trust you, and the IRS would like to know your availability for consulting.
3 – 4 correct: You may not be ready to draft tax policy, but you’d absolutely survive a colonial tavern debate about whiskey taxes.
1 – 2 correct: Consider this your official introduction to the wonderfully strange world of U.S. tax history, and a reminder that some of these questions would have puzzled people in the actual centuries they happened.
Saving for retirement is not a one size fits all journey, as each stage of life comes with different priorities, pressures, and opportunities. No matter where you are in your journey, here are savings tips from established financial publications and organizations to consider for every age.
In Your Twenties – Building Early Habits
For many people, this decade is less about large balances and more about establishing patterns. Financial education outlets frequently emphasize the long runway available to younger savers. Investopedia.com discusses the long term impact of starting early and allowing time to work in your favor.
Common themes during this stage include:
Developing a regular saving habit, even in small amounts
Exploring employer sponsored retirement plans, when available
Learning basic investment concepts over time
Treating retirement contributions as part of monthly expenses
Expanding skills and experience that may increase earning potential
In Your Thirties – Adding Structure
As careers and family responsibilities grow, retirement planning often becomes more deliberate. For example, Charles Schwab provides a decade-by-decade overview of how retirement priorities may shift during this phase of life.
Conversations during this decade often revolve around:
Reviewing contribution levels as income changes
Understanding how employer matching programs work
Paying attention to debt and interest costs
Considering how lifestyle decisions shape long term finances
Evaluating career growth or additional income opportunities
In Your Forties – Taking Inventory
Mid-career can be a natural time to assess progress and revisit long term projections. Many financial institutions have programs that address these topics.
Topics frequently discussed include:
Reviewing current balances alongside projected needs
Understanding how high interest debt may affect cash flow
Identifying gaps between current savings and future income goals
Revisiting contribution levels and investment allocations
Checking Social Security earnings records for accuracy
Considering whether new income streams may strengthen retirement readiness
In Your Fifties and Sixties – Focus on the Finish Line
As retirement moves closer, planning conversations often shift toward income timing and lifestyle expectations. AARP maintains a retirement resource center that covers considerations commonly discussed in the years leading up to retirement.
Areas that frequently come into focus include:
Continuing to save where possible
Eliminating or reducing outstanding debt
Thinking through retirement timelines and income sources
Factoring healthcare and lifestyle preferences into cost expectations
Clarifying what retirement may look like day to day
Timeless Principles That Apply at Any Age
No matter where you fall on the timeline, a few core ideas always support progress.
Automate savings to remove decision fatigue
Avoid comparing your progress to others with different circumstances
Revisit your plan occasionally rather than ignoring it entirely
Focus on what you can control today
The Bottom Line – Start Where You Are
Retirement planning is not about catching up to someone else’s path. It is about making the best decisions you can with the resources you have right now. Wherever you are starting from, taking action today creates options for tomorrow.
With the individual tax-filing deadline on Wednesday, April 15th, now is the time to complete all filing arrangements and payments.
What follows is information typically provided in our filling instructions to you when the tax return is completed.
However, upon review, it makes sense to provide this information to everyone, whether you have filed or not. It is good information to know, so if you have not already done so, ask yourself these questions:
Did you sign your e-file authorization form? IRS Form 8879 needs to be signed by you before your taxes can be e-filed. If filing jointly, your spouse needs to sign as well. If you haven’t already, please return the signed form ASAP to ensure that your taxes can be e-filed on time. But don’t sign it before reviewing the tax return. Remember, this signature means you agree with the accuracy of the tax return.
Do you need more time to file? If you are not ready to file your taxes before the initial April 15th deadline, you can file for a six-month extension. Be aware that it is only an extension of time to file – not an extension of time to pay taxes you owe. You still need to pay all taxes by April 15th!
Do you owe money? If yes, make your tax payment now! The IRS has several payment options on their website. If mailing a payment, include Form 1040-V and ensure the mail is postmarked on or before April 15th. Sending the payment by certified mail will ensure you have proof of a timely payment. Late payments, even by one day, are subject to IRS penalties and interest.
Do you need to deposit funds in your IRA or HSA? Did you claim an IRA or HSA contribution on your tax return? In order for the deduction to be valid for 2025, all deposits to those accounts need to be made by April 15th. Once completed, save proof of the contribution with your 2025 tax files.
Do you need to make an estimated tax payment? The first quarter estimated tax payment for 2026 is also due by April 15th. If you owe taxes for 2025, making 2026 estimated payments might make sense for you. A quick way to calculate a first quarter payment is to divide the taxes you paid in 2025 by four, then adjust this number for any paycheck withholdings. Send your payment along with Form 1040-ES to the IRS by April 15th. Then schedule a tax-planning meeting to determine the best approach for the remainder of the year.
If you do miss a deadline, file your return and pay the taxes as soon as you can to stop the accruing of interest and penalties.
