Archive for ‘Taxes’ Category
How to Organize Yourself for a Stress-Free Tax Season

Nobody likes paying taxes, but if you’re organized, the discomfort can be limited to the money leaving your bank account and not all the work leading up to it. Preparing your tax returns (or getting the information to your tax preparer) doesn’t have to be annoying. To that end, every few years, I try to provide a Paper Doll primer on what you need to know and understand to make tax time bearable. This year, it has bonus pop culture to keep you entertained!
SET THE STAGE FOR PAYING THE TAX MAN

Photo by The New York Public Library on Unsplash
Tax prep is the homework of the adult world, but that doesn’t mean it can’t be easier (or more fun) than finding the area under a curve or remembering what cosin and tangent are.
Start by creating a comfortable work environment. Clear your desk of clutter and distractions. If that’s not possible (in the amount of time you have), consider moving to a new workspace just for doing your taxes. That might be the dining room table, the guest bedroom, or the conference room at work on a Saturday afternoon.
The key elements are ample workspace, a place to put (and if necessary, plug in) your computer, functional Wi-Fi, a pad of paper for taking notes, access to good lighting and a comfortable chair, and your tax prep documents (of which, more later).
More importantly, do what you can to eliminate interruptions, whether that means working when others are out of the house (or getting out of the house to do your work).
Create the right ambiance for your style. Some people need a window facing sunlight, while I prefer to have my chair face a blank wall to eliminate distractions. Some people need silence, while others prefer white noise. If you used to do your 9th grade math homework with your stereo blasting, try making a tax prep playlist using Hubpages’s 50 Best Songs for Tax Day.
Don’t feel like you have to get your taxes done all in one sitting. If your return is simple (one W-2 and few 1099s) and you’re filing online, you might wrap it all up in an hour. But if there’s a lot of complexity in your finances, plan multiple shorter stints. Find chunks of time to:
- gather (and if necessary, download and print) official documents
- isolate and review all types of income
- isolate and review deductible expenses reflected on forms
- locate deductible expenses reflected on receipts (tangible and digital)
- fill in online tax preparation software like TurboTax or TaxCut, but then walk away and come back later to check your work; or
- make an appointment to sit with a professional tax preparer
Take frequent breaks to keep your mind fresh. Stay hydrated and have light, healthy snacks. When you finally finish, celebrate with a small ritual to reward yourself for all that adulting.
While I’m not always happy with the way my tax dollars are spent, I often find that the filing (if not the paying) of them goes down better with a listen to Irving Berlin’s WWII-era I Paid My Income Taxes Today. (The only version I found with Berlin singing it himself was a bit too jingoistic, so I present singing cowboy Gene Autry.)
GATHER YOUR RESOURCES
One of the most common frustrations my clients have is that they don’t know where to start. The fear of mysterious forms and documents starts the buzz of anxiety. I encourage a few simple steps for making the experience easier to bear.
Time Travel to Last Year
The easiest way to estimate what forms you’ll need this year is to start by looking at what you dealt with to prepare your taxes last year. You should have a folder with everything you (or your tax preparer) used to support last year’s tax returns. Scanning through last year’s taxes and supporting documents will help you create a checklist of what you’ll need for your treasure hunt.

Photo courtesy of Chris Potter/CCPix at www.ccPixs.com under CC 2.0
First, there’s the income side of things. Did you have a job? You’ll be looking for a W-2. Were you freelancing? Find those 1099s! Did you get paid interest or dividends? There will be 1099s for those, too.
Then, on the flip side, there are your expenses. You’ll have some fancy forms, like 1098s for interest paid on mortgages or tuition costs, but you’ll also need to gather receipts.
But that’s generally it, just what did you earn and what did you spend? (Obviously, not everything you spend is tax-deductible. The cheeseburger and fries you eat on your way home from the gym? That receipt can go. The one from when you took your best client to lunch to propose extending a contract? Hold on to that receipt!)
Answer Mail Call
In general, employers and financial institutions are supposed to mail tax documents like most 1099s and 1098s by January 31st, so you should have them in hand already. (Got a pile of unopened mail on top of the fridge? Now’s the time to open it!) Other forms, like 1099-B, 1099-S, and 1099-MISC don’t have to go out until February, so watch your mail. And, annoyingly, Schedule K-1 forms (related to partnerships, LLCs, and S-corps) generally don’t get mailed until early-to-mid March!
Don’t just think in terms of U.S. postal mail. Be sure to check your email, too!
I have quite a few clients, particularly those over 80, who don’t dependably check their email, and don’t necessarily realize that institutions have stopped sending paper copies of essential forms. Instead, they send emails alerting you to the existence of your forms in online portals.
If your inbox is full of hundreds or thousands of unread emails, try using the search bar for terms like “tax forms,” “1099,” or the word “tax” and the name of some of the institutions that should be sending you tax documents.
Let Your Fingers Do the Walking
Waiting for the official mail can be frustrating, especially if you are hoping to get a tax refund and want to get your taxes prepared and your return filed as soon as possible. In many cases, you don’t have to wait — just head to your keyboard, log in, download, and print.
For example, a client was recently frustrated with herself because she suspected that, in a fit of tidying the paperwork from last fall for enrolling in a 2026 health insurance plan, she’d accidentally shredded her 1095-A, her Health Insurance Marketplace Statement. Frustration turned to delight, however, when we logged into her Healthcare.gov account and quickly downloaded another copy.
Starting with your list of all of the institutions that have sent you tax documents in the past, and then adding any that know about your income/outgo, log in and search for a menu title like “tax forms” or “documents.” For example, log in to your:
- Bank accounts for 1099s
- Brokerage/investment accounts for 1099s
- Lender sites for 1098s
- Social Security for SSA-1099
- Health Insurance Company for annual summaries of medical and pharmaceutical expenses
- Paypal, CashApp, Venmo, Square, and similar platforms (for 1099-K and other records of income and expenses)
Remember that you may also have receipts that came to you by email. (If you haven’t gotten into the habit creating a “receipt” folder in your email or printing receipts for potentially deductible expenses, this is this is the time to start.)
Further, if you need to access information that’s on your prior tax returns and you don’t have them accessible — for example, if you’ve been the victim of a natural disaster, or you and an ex haven’t been able to amicably share data — you can get tax records and transcripts directly from the IRS.
Once you file your taxes, make a list of all the forms you received this year (and how/where you acquired them), and tuck that list into your tickler file for next January. Check off each form as it arrives, and you’ll have a better sense of when you’ll be ready to start working on your 2026 taxes in 2027.
KNOW YOUR FORMS
Much of the fear associated with tax time comes from the fact that the language referring to the different types of forms seems like gibberish.
Here’s a reminder of what each of the most common forms related to income and deductible expenses represent.
Let’s start with income.
W-2 (Wage and Tax Statement)
Were you an employee in 2025? If so, your employer should have provided one W-2 to you and one to the IRS, reporting how much you were paid (in wages, salaries, and/or tips). If applicable, the W-2 should should also indicate how much money was withheld (from you) and paid to another entity.
Federal, state, and local taxes, FICA (Social Security and Medicare), unemployment insurance, and a few other withholdings are considered statutory payroll tax deductions, because they are governed by statues (AKA: laws).
Sometimes, courts rule that an employee’s wages can be garnished (which sadly has nothing to do with caviar or sprigs of parsley). In these cases, individuals who owe money from lawsuits or are behind on child support may have money removed directly from their earnings, before it ever gets to their paychecks, to ensure it goes directly to whomever is owed. A W-2 will reflect this.
A W-2 may also report voluntary payroll deductions, amounts withheld from paychecks with your permission. Examples include your portion of health and life insurance premiums, contributions to a 401(k) or other retirement fund, employee stock purchasing plans, one-time or ongoing donations to the United Way, union dues, etc.
In theory, a W-2 should be mailed to the address listed on your W-4. (The W-4, is the form that tells your boss how much to withhold based on your number of dependents you have.)
Smaller companies may just hand you your W-2 instead of mailing or emailing it, but if your W2 is missing, consider:
- Did you change employers last year? You should have received W-2s from each employer. (If you changed jobs at the same company, you’ll receive one W-2 from each employer, not one per position. If you changed companies within a larger corporation, though, you may get one for each.)
- Did you change addresses since you filled out your W-4? There’s only so much a former employer will do to track you down to give you your W-2. Keep the Madge in HR updated!
Don’t assume that if you don’t have your W-2, then nobody knows what you made. Remember, your employer sends the IRS a copy of your W-2. Since the IRS knows what you made, be sure you do, too! (If your former company went out of business or is otherwise not returning your calls, the IRS has a procedure to help you file your taxes in the absence of a W-2.)
Examine your W-2 it carefully. Do the numbers seem right? Compare them to the final pay stub you got for last year. Calendar years may end mid-week (or even mid-pay period), so the numbers won’t correspond perfectly, but they’ll be close enough for you to spot if something is seriously wrong. The sooner you call your employer’s attention to an error, the sooner you can prepare your return.
W-2G (Certain Gambling Winnings)

Gambling Photo by Pavel Danilyuk on Pexels
The W-2G is the wild-and-wooly cousin of the W-2. While a W-2 is for money you make while working, the W-2G is what you get while playing. If you win more than $600 in any gambling session at a casino, the “house” should request your Tax ID (generally your Social Security number) and either prepare a W-2G on the spot or send it to you in January.
Casinos aren’t interested in keeping up with your losses, just your winnings, so they only tell the IRS about what they paid you. If you want to deduct losses to offset winnings, the IRS requires receipts, tickets, statements, or other records to support both your winnings and losses.
1099s
A 1099 is a form that basically says, “Hey, you weren’t an employee but we paid you money this year.” You get a copy; the IRS gets a copy. (Cue Oprah: “You get a copy! You get a copy! Everybody gets a copy!”)

There’s not just one type of 1099; actually, there are 22 different kinds of 1099s as of 2026! Don’t worry, you won’t be tested on this. But it helps to be familiar with some of the more common versions, like:
You may not have interest in 1099s, but 1099-INT reports the interest you receive — from interest-bearing savings and checking accounts, money market bank accounts, certificates of deposit, and other interest-paying. It also reports whether (U.S. or foreign) taxes were withheld and if there were any penalties assigned for early withdrawal from an interest-bearing account.
If you received less than $10 in interest, your bank may not send a 1099-INT.
Whether you’re TikTok’s viral man in finance, 6’5″, with blue eyes, and a trust fund or your grandma bought you one share of stock in Disney for your 10th birthday, you’ll get a 1099-DIV to indicate the dividends or capital gains you received as an investor. (Note: if you have a DRIP — a dividend re-investment plan — you many never see these dividends as checks sent to you. They’re literally re-invested in your portfolio.)
Again, if you didn’t earn at least $10 in dividends, you are unlikely to receive a 1099-DIV.
1099-G (Certain Government Payments)
This random-sounding form can cover everything from state unemployment compensation to tax refunds, credits, and offsets at the state and local level. It can also be used to report payment of taxable grants, agricultural payments, and other nifty things where a state or local government gives you money.
The 1099-K reflects payments to you from third-party settlement organizations (TPSO) like PayPal, Apple Pay, Venmo, or Zelle and platforms like Etsy or TikTok. This form was supposed to go into effect several years ago, but due to the pandemic, its use was delayed, and for several years, the threshold was $600, but has now been raised to $20,000 (and 200 transactions).
If you’re self-employed (a freelancer, an independent contractor, etc.), clients should send a 1099-NEC. However, although 1099-NEC came into use in 2021, some offices still send 1099-MISC by mistake. Just remember, whatever form you get, the IRS knows about it, so don’t try to hide that money.

Also remember that even if someone paid you for doing work as an independent contractor, they may not know they should be sending you a 1099-NEC or any form at all.
So, if you are self-employed or irregularly employed, it’s essential to keep track of your own incoming revenue. (Otherwise, if the person who paid you ever gets audited, it could trigger some messy situations for you, too.)
Now that the 1099-NEC covers income for freelances and independent contractors, this one is much more “miscellaneous.” As I’ve said before, it’s the junk drawer of tax forms!
1099-MISC is used to report payment of royalties, broker payments, certain rents, prizes and awards, fishing boat proceeds (yes, really!), crop insurance proceeds, and some payments to attorneys that wouldn’t be reported on a 1099-NEC, like if you received a settlement that required an attorney to get paid a portion contingent upon your winning.
If you get Social Security benefits, you should receive an SSA-1099. (Non-citizens living outside the US, like widows/widowers receiving spousal Social Security benefits, may get a SSA-1042.) The 1099-SSA tends to come on a weirdly long form, folded and sealed such that it makes its own envelope. Unfortunately, it looks like junk mail, so watch out for it and replace it, if necessary!
You Never Give Me Your Money, or Why Income Isn’t Always “Real” Money
A 1099 doesn’t always indicate that you were literally paid money. For example, remember how I said that you may get a 1099-DIV, even if you never actually got the dividend payment because it was re-invested?
Similarly, a 1099-C indicates that someone forgave a debt, like a student loan or a credit card balance. That forgiveness is a relief, but you may owe tax on forgiven debts, and the 1099-C alerts the IRS that since you didn’t pay money owed (and got to keep it), it’s as if you received money.
1099s May Be Hidden in Plain Sight
Sometimes, instead of sending a 1099 in a separate envelope, a bank or brokerage house may include a 1099 form in the same envelope — sometimes perforated at the bottom of a quarterly or end-of-year financial statement, or on the reverse side of a related form. Brokerage houses often send multiple forms as a “combined 1099,” scrolling across multiple pages.
Check all that boring-looking official mail!
Of course, income is only half of the equation. On the other side, you get to use forms and receipts to determine how much you can deduct or write off.
So, let’s look at expense documentation.
1098 (Mortgage Interest)
A 1098 is not a 1099 that’s been taking Ozempic. A vanilla, no-frills 1098 reflects the interest paid on a mortgage, which is generally deductible on federal taxes. Renters don’t pay interest, so they don’t get 1098s; neither do homeowners with paid-off mortgages.
Sub-types of 1098s reflect money you’ve paid for things other than interest on property loans:
- 1098-T shows tuition you paid; you’ll get this from a college or training school.
- 1098-E reflects you’ve paid interest on a student loan; it will come from your lender.
- 1098-C indicates the value of a donated car, boat or airplane. So, if you’re a fancy-pants, monocle-wearing Thurston Howell III or his wife, Lovey, you’ll get this from the agency or organization receiving the donation.
1095-A (Health Insurance Marketplace Statement), 1095-B, and 1095-C
You’ll get a 1095-A if you enrolled in health insurance coverage through a state or federal exchange.
1095-B (supplied by companies with fewer than 50 employees), details the the type of coverage you had through work, the period of coverage, and your number of dependents, so you can prove you had the Minimum Essential Coverage (MEC) required by law.
A 1095-C is similar, but for employers with more than 50 employees.
Schedule 1-A (Additional Deductions)
The Schedule 1-A, to be used with the 1040 return, the 1040-SR return (for seniors) and the 1040-NR (for non-resident aliens) is a new form for calculating some of the new deductions related tips, overtime, new purchases of cars manufactured in America and the enhanced deductions for seniors (see below).
Got all that?
IMPORTANT NEWS FOR THE 2026 TAX SEASON
Know Your 2026 Tax Deadlines
The federal tax deadline is Wednesday, April 15, 2026.
If you file a (valid) extension request, you have until October 15, 2026 to file your tax return. However, you still have to PAY what you (estimate that you) owe by April 15th to avoid a fine.
It’s true that if you won’t owe anything, there’s no penalty for filing late (without an extension), but then you’ll be delaying receiving a refund.
Age Has Its Advantages
Did you know that adults aged 65 and older may qualify for a new $6,000 deduction this year, in addition to existing standard deductions?
The deduction starts phasing out for single filers with incomes above $75,000 and for joint filers above $150,000. Once you hit the threshold, the deduction gets reduced by six cents on each dollar above the applicable threshold. Once your adjusted gross income hits $175,000 (for single filers) or $250,000 (for joint filers), the deduction is effectively reduced to zero.
This $6,000 deduction applies regardless of whether you take the standard deduction or choose to itemize. Also, it’s not permanent, applying only from this year through the 2028 tax year.)
Direct File Is No Longer An Option
A few years ago, I shared information about a government program that allowed people with simple returns (income solely from from employment, unemployment compensation, or Social Security, and only taking a standard deduction) to file directly with the government at no cost. The current administration has cancelled this program.
If you’re seeking a no-cost or low-cost way to file your taxes without working with a professional or filing through paid commercial software or online platforms, consider the following options for filing your 2025 returns:
- file out a paper form (often available in public libraries) or use IRS Free Fillable Forms
- see if you are eligible (depending on your adjusted gross income) to use IRS Free File and file through one of the eight online programs
- seek volunteer tax preparation programs like the Volunteer Income Tax Assistance VITA and Tax Counseling for the Elderly (TCE)
Don’t Procrastinate If You Plan to Mail Your Return
Filing tax returns at the last minute is a time-honored tradition. I’ve seen postal workers outside in the late hours, clad in reflective gear, taking possession of people’s returns.
Unfortunately, if you prefer to mail your tax return, filing on the last possible day may not be workable anymore.
At the end of last year, the US Postal Service announced that it was changing the methods for postmarking mail. They will still stamp the current day’s date on your tax return envelope, birthday card to your grandma, or care package to summer camp when they get to a USPS processing facility. The problem? It might take longer for your mail to get from where you give it to them to an actual facility.
Apparently the USPS is looking at ways to save money. One of those strategies includes reducing the frequency with which it picks up mail from local post offices. This means fewer trips from your drop-off point to a processing center, and THAT means it’s less likely that you’ll get a same-day postmark.
So, if you put your mail in your outside mailbox with the flag up, it could take a few days to get where it’s going. If you drop it in a blue maiilbox in front of a post office that isn’t a processing facility, it could take at least another day. Grandma may not care when an envelope is postmarked, but the IRS does. (And if you’ve got a deadline for mailing something for legal purposes, it definitely does.)
So, your mail may not get postmarked the same day you send it, even if you send it from a post office. That means that finishing your taxes at 11:30 p.m. and jumping in your car to head to the post office on the corner just isn’t going to cut it anymore.
Your best option is to file and pay your taxes online. But if you must mail your return, you may want to ask at your local post office if they are able to manually stamp and postmark your tax return.
While it will be more expensive, another option is to use a private shipper for your tax paperwork, like FedEx or UPS.
FINAL THOUGHTS
Paper Doll is a Certified Professional Organizer, not CPA or enrolled tax preparer. Always verify your questions with a tax specialist. If you receive a funky form and don’t know what to do with it, the IRS has a surprisingly easy Forms, Instructions and Publications Search.
Most importantly, remember that the sooner you get organized for tax time, the less likely you are to end up like Homer Simpson.
Organize Your Charitable Donation Strategy

Every day last week, your email inbox was filled with Black Friday and Cyber Monday notifications. But starting today and throughout the month, you’ll probably notice an influx of requests for charitable donations.
This starts with tomorrow’s Giving Tuesday, a unified movement that:
…unleashes the Power of Radical Generosity around the world. GivingTuesday reimagines a world built upon shared humanity and generosity.
Our global network collaborates year-round to inspire generosity around the world, with a common mission to build a world where generosity is part of everyday life.
Whether it’s making someone smile, helping a neighbor or stranger out, showing up for an issue or people we care about, or giving some of what we have to those who need our help, every act of generosity counts, and everyone has something to give.
The term “radical generosity” is defined as the concept that the suffering of others should be as intolerable to us as our own suffering. This may seem like an odd topic for an organizing blog, but I believe that organizing your efforts can allow radical generosity to reinvigorate the delight of giving.
THE UNIVERSALITY OF CHARITABLE GIVING
In Judaism, the concept of tikkun olam means “to repair the world,” and refers to the notion that people have a responsibility to improve the world through acts of kindness and social justice. Judaism also has the concept of tzedakah, commonly used to mean charity, but more fully is explained by the notion of making the world a more just place.
Though I am no expert on other faiths, I do know that charity is an important tenet throughout faith practices. In Christianity, it’s reflected in 2 Corinthians 9:7, “Each one must give as he has decided in his heart, not reluctantly or under compulsion, for God loves a cheerful giver.” Islam notes that the prophet Muhammad said, “Charity does not decrease wealth” to point out the value to the benefactor as well as to those who receive kindness.
In Hinduism, “There is none other who does greater good than the one who removes the hunger of those in a difficult situation, helpless, weak and disturbed.” And Sikhs believe in the concept of sewa, which means “selfless service,” helping others without expecting any reward or personal gain.
Of course, donating money (and goods) is not a concept specific to any one religion, or indeed any religion at all. Ideas such as charity and mutual aid (where a community shares and exchanges resources and services to help one other) can be found in every nation and at every income level. People make donations in their houses of worship and to their schools, to strangers on the street and to well-known non-profits.
Donating money (as well as volunteer time and skill) is a great way to model your values to your children and to others in your community. You could limit round-robin gift exchanges at work or among your extended family and work together to donate funds or effort to non-profits or causes that reflect your highest good.
So yes, thoughtful giving is good (and good for you), but the requests for giving can be overwhelming.
Just like how the clutter of too many possessions in a household can paralyze someone and prevent them from knowing what to do next, a mailbox or inbox cluttered with charitable donation requests can be problematic, particularly during the holiday season from Thanksgiving through the New Year, when everyone is focused on gratitude and lovingkindness.
But if you woke up to seventy-three charitable requests today, you might not be feeling very grateful, loving, or kind. I get it.
THE CHALLENGES OF CHARITABLE GIVING
There are a variety of obstacles people face when inundated with charitable requests.
Stress
- Being inundated by a flood of donation appeals — Non-profits know that you’re in a giving mood (or are feeling pressured to be in a giving mood). People are accustomed to donating at the end of the year, whether for religious, social, or tax reasons, so the donation campaigns behind mailers and emails and social media requests are part of the design.
- Pressure and guilt — It’s common to feel obligated to respond to every request with a donation or gift, even when it exceeds one’s budget or doesn’t align with one’s values. Nobody wants to feel selfish, but it’s important not to give more of yourself than you can afford.
Fears about security
- Increases in frauds, hoaxes, and scams — Sometimes, “charitable” requests come from bad guys using guilt trips and names just similar enough to real charities that it’s common to worry about whether your gift will get to anyone except a thief’s pockets.
- Validity of a charity — Even if a charity is “real,” even if it’s well-known, it doesn’t necessarily mean that a sizable portion of the funds raised will get to the expected recipients. Sometimes a shocking percentage of those donation funds go toward administration, chief executives, advertising, and anywhere but where you’d hope it would go.
Financial anxieties
- Budget constraints and unrealistic goals — At this time of year, our wallets pulled in different directions, like taffy. You’re likely to want to earmark funds for holiday gifts, meals, and travel, on top of regular expenses, but it can be tough to find the Benjamins for donations. Being overly ambitious with our charitable giving leads to the same kind of anxiety as when we’re overly ambitious about gift-giving to friends and family. It feels good in December, but when our January bank and credit card statements arrive? Ouch!

- Unplanned donations — There’s a reason you hear financial advisors talking about planned giving. Planning is organized, and when you are organized, you feel in control. When unexpectedly faced with an in-person appeal for a donation, the emotion of the experience combined with social pressure (on top of financial pressure) can prompt you to spend more than you can comfortably do.
Emotional kerfuffles
- Family disagreements — You thought the political arguments at the Thanksgiving table were stressful? Imagine trying to come up with a plan for family giving when the members of the family are of two minds regarding who is “deserving” of family donations. If one person wants to give to the NRA and another to support of LGBTQ+ teens, but the funds need to come from one couple-owned or family-managed source, sparks may fly.
- Decision fatigue — The sheer volume of need can be overwhelming. Everyone wants your money, and so many charities and worthy causes requesting donations, it’s often difficult to decide which ones to support.
- Charitable burnout — People who donate regularly may feel resentful from the ever-increasing demands during the holiday season.
- Compassion fatigue — Let’s face it. We’re human. Constant reminders of those who are hungry, abused or victimized, troubled, or struggling can become wearying, especially for those who already struggle with some of the harder emotions of the holiday season. While such requests often remind us to feel grateful for what we have, it’s not unusual to feel guilty for not feeling quite so grateful about our own struggles.
OVERWHELM COMES FROM LACK OF PRIORITIZING, PLANNING, AND ORGANIZATION
Over the past 23 years I’ve worked as a professional organizer, one of the constant holiday-time struggles my clients face is what to do about all of the charitable donation requests. Several years ago, I worked with a client on her backlog of important documents and papers. We were making great progress until I arrived one day to find her agitated. She admitted that she’d been “hiding” some papers because they were so stressful for her to think about.
In a room we’d never entered, there were desks, tables, chairs, and a bed, and a variety of other horizontal surfaces covered in envelopes — most of which had never been opened — all seeking donations! There were multiple years of requests!
At first, this sweet woman had just given a few dollars to everyone who asked, but that just led to more and more requests. (I’m not saying that non-profits sell their mailing lists, but yes, some non-profits sell, or at least “rent” their mailing lists. It’s ethically questionable, so before you give, you may want to read a charity’s privacy policy regarding whether they will share donor information without prior consent.)
The client and I started by eliminating all requests from prior giving seasons, then deleted duplicates (and triplicates). Then we developed a strategy that works for most people.
START WITH YOUR BUDGET
Just as some people prefer to say they are on an “eating plan” rather than a “diet,” feel free to think of this as a giving plan, rather than a budget. The idea is to set boundaries you can live with, as it makes no sense to donate so much to end hunger that you will be eating ramen noodles every day to make up for your economic shortfall!
Consider these factors:
- How much can you reasonably afford to give? This requires first having a handle on all of your fixed and variable expenses.
- Would you like to allocate a percentage of your monthly budget for donations? Do you prefer to tithe, set aside a fixed dollar amount per month, or pick some other percentage approach?
- Do you prefer to give an annual gift or arrange monthly contributions?
- If you choose monthly donations, do you want to donate to the same charity every month, or multiple charities but during different months?
- Do you want to set aside extra money (in monthly petty cash) for unexpected, ad hoc requests by organizations or individuals? (You might choose to keep a stash of gift cards for grocery stores or restaurants to give to unhoused or struggling folks you come across, rather than giving cash, to prevent them from becoming victimized by thieves.)
- Does your company offer an annual charitable donation match? If so, taking advantage can stretch your donation dollars!
FOLLOW THE MONEY
You will want to track your donations to make it easier to file your taxes and take all possible deductions.
If you respond to mailed requests for donations, you can write a note on the donation letter, stating how much you donated, on what date, by what method (check number or which credit card). Put that in your tax prep folder for the current year. When/if you get an official letter from the charity thanking you for your donation, match it to the corresponding note and staple it.
If you tend to make donations online, be sure to print a copy of your receipt as a PDF (if you want to keep records electronically) and maintain a donation folder on your computer or in your cloud storage. (You could also print receipts on paper and put them in your tax prep folder; just don’t double-count donations that appear in digital and print form.)
Of course, you can also use financial apps, budgeting software, or spreadsheets to track your charitable contributions. The more money you donate, or the more complex and numerous your donations, the more cautious you will want to be to keep these records for tax purposes. But tracking your donations is about more than just taxes.
In the heyday of magazines, as soon as you’d renew a subscription, you’d start getting reminders to renew again. The more subscriptions, the harder it would be to realize you were being prompted so often that you were subscribing more than once every twelve months. Well, with charities it can be much the same thing. Keep a written record of when you’ve donated to make sure you’re not donating more often than you planned.
CHOOSE YOUR CHARITIES, DON’T LET THEM CHOOSE YOU
Professional organizers often talk with clients about the dangerous power of advertising and in-store displays. We can be going along, thinking we’re doing great with our spending plans and then all-of-a-sudden we are sucker-punched by an enticing commercial or a product display. We didn’t plan to buy it. We didn’t need it. But oops, we got it.
Those donation emails and envelopes may as well be shouting: “This offer is available for a limited time only. Operators are standing by!” but the truth is that non-profits are always in need of money. You may get dozens of requests for donations in December, but your contributions will be no less valuable, life-saving, or appreciated if sent three or six months down the line. Unless you have a very specific need for making a very specific dollar amount of donations before the end of the calendar year, don’t let yourself feel pressured.
Decide on your giving goals in advance. Make this a giving plan.
Prioritize Your Values First
When you try to downsize a closet on your own, you might pick up one article of clothing and ask yourself “keep or set free?” (whether “set free” means toss or consign or donate or use as a rag). A straight-up yes/no choice can be difficult. But if a professional organizer asks you to first pick your ten favorite pieces from your closet and set them aside, it will be much easier to start evaluating your less-loved pieces.
Similarly, if you’re facing a mountain of charitable giving requests, choosing yes or no may feel like you are saving or damning the recipients of each non-profit. No wonder you’re stressed!
So, start by prioritizing the causes that align most closely with your values. For example, those might be:
- education
- the arts
- health/medical
- hunger
- animals
- children
- the environment
- faith communities
- disaster relief
- international relief
- social causes
- political causes
- at-risk communities
- marginalized communities
Once you’ve identified a general cause area that matters to you, you can narrow your focus. You can determine whether you want to donate locally to keep funds in your community or donate to a national effort with a more powerful network of resources.
Research Potential Charities
You do not have to reinvent the wheel. There are some excellent resources for evaluating non-profits and explaining how they rank on transparency, impact, and mission alignment. Consider:
Charity Navigator

Charity Navigator has been around for almost 25 years, and has rated 225,000 charities. Their ratings focus on the “cost-effectiveness and overall health of a charity’s programs, including measures of stability, efficiency, and sustainability.”
GuideStar

Candid’s GuideStar focuses on non-profits in the United States. Search to verify a charity’s legitimacy, learn whether contribution will be tax deductible, view up to three years of a non-profit’s IRS Form 990, read revenue and expense data for the current fiscal year, and learn about a charity’s CEO, Board Chair, and Board of Directors.
BBB Wise Giving Alliance

Give.org, the Better Business Bureau’s Wise Giving Alliance, generates reports that address all of the issues a donor might want to consider, including governance, finances, results reporting, transparency, and appeal accuracy
Charity Watch

Charity Watch, originally founded in 1992 as the American Institute of Philanthropy (AIP) claims to be the only independent charity watchdog in the United States. Charity watch notes that they “dive deep into charity audited financial statements, tax filings, state solicitation filings, and other information so we can let you know how efficiently a charity will use your donations to fund the programs you want to support. CharityWatch exposes nonprofit abuses and advocates for your interests as a donor.”
GiveWell

Rather than focuses only on financials, GiveWell conducts “in-depth research to determine how much good a given program accomplishes (in terms of lives saved, lives improved, etc.) per dollar spent.”
If you decide you want to focus on local charities, you’ll need to do more of your own legwork. For example, if you want to support a local shelter, food bank, or other community initiative, read the website, research who sits on the board of directors, and see where local news media has covered the impact of these charities.
Concentrate on local efforts that focus on long-term community solutions and have a record of efficient use of funds and a history of measurable results.
DEVELOP A DONATION STRATEGY
Once you know which causes are meaningful to you, you can delete or discard donation requests from causes that aren’t high on your list of values.
Yes, really.
Charitable causes are important, but not all causes have to be equally important to you, just as they need not be equally important to all individuals. You get to pick what you value.
Once you identify the causes you value, you can research the specific charities in each.
Let’s say eliminating hunger is important to you. It’s possible you’ll get requests from Feeding America (a nationwide network of more than 200 food banks), the World Food Programme (an international organization within the United Nations that provides food assistance worldwide), No Kid Hungry (providing grants to schools and partners to end child hunger), Meals on Wheels (working to end hunger and loneliness among the elderly), etc.
- Collect all the requests that come in via mail or email in a “holding area” until you’re ready to research them.
- Research the charities to see which appeal to you the most.
- Decide the number of charities to which you will give.
- Pick the frequency of your donations: one time or recurring?
- Divide your giving budget by the number of donations.
- Donate in a way that works for you.
- Record and track your donations for tax purposes. (Save receipts and acknowledgment letters in your paper or digital files)
- Evaluate amounts and charities annually.
For example, might decide to give to one national charity, once per year, in an amount that feels generous to you. Conversely, you might pick four of these charities and give once per quarter.
Alternatively, you could set up a monthly payment to one (or more charities) on your credit card, but you’ll want to revisit that plan annually to make sure the charity still fits your values.
Or, this process of reviewing your values may make you turn your attention to local concerns. You could still give small donations to one or more of the charities that fits you criteria, but then you could contact a local elementary school and offer to pay all outstanding meal fees. In many school districts, children whose families are behind on their lunch fees are unable to get hot lunches and are given cold lunches that make them a target of bullying. In other districts, they simply get no lunch at all. Hungry children cannot learn.
You could pick an amount to pay toward students’ outstanding lunch debt each month, or pool resources with your colleagues or neighbors to pay off those debts once or twice per year.
This is merely one example. You can make lots of donations in December to lots of charities, and then skip the rest of the year. You can pick twelve charities and give equal amounts, one per month, all year, and revisit the charities you’ll choose each year. Or you can mix-and-match local and national donations as you see fit.
The key is to mindfully research, plan, and track your giving so that it allows you to feel generous (and lucky to be able to help) rather than overwhelmed by charitable request clutter and anxious about the entire experience.
LIMIT DONATION ANXIETY
Creating a giving plan and sticking to it (at least for one year) will allow you to eliminate the excess requests before they pile up, but there are additional things you can to do keep from feeling like a Grinch.
Limit the solicitations that come your way.
If you are getting too much donation request mail or email — which, again, is really just (earnest) advertising, it’s OK to click to unsubscribe from the email or call to opt-out of the mailing lists.
Alternatively, you can use a dedicated email address (like PaperDollDonations@gmail.com) whenever you make donations. That way, you only need to check that address when you’re looking for donation confirmations for tax purposes, or when you’re in the mood to actually look at the plethora of mail sent your way. But it never has to hit your main inbox.
Let Go of the Guilt
Just because you receive address labels does not obligate you to make a donation to a charity, just as receiving a holiday card from a distant acquaintance does not obligate you add the individual to your card list. Don’t let them turn advertising techniques into a free ticket on the Guilt Trip Express. Use your brain — then give from the heart.
Learn to say “No” gracefully. Just as you cannot keep everything you ever bought or were gifted, you cannot donate to ever cause that asks.
To increase your comfort with saying no, prepare a mental (or written) script for declining requests.
Remind yourself (and if you wish, explain to others) that you have a planned giving strategy. You have organized your giving to ensure that your efforts are mindful and value-driven. You can, if you wish, give an ad hoc donation, but you can also just say you’ll be happy (if you will be) to consider a donation in your next giving cycle in 2026.
Finally, remember that you need not always give money. Donating your possessions, time, and service to non-profits can be even more valuable than the amount of money you could afford to donate.
Speaking of volunteering, we are sometimes asked to donate our time and effort to worthy causes at the holidays when our schedules least allow us to help. (Also, many popular volunteering activities, like serving meals at shelters, are booked quickly during the holidays.) But guess what? Shelters and food kitchens need volunteers year-round! Just as money is needed just as much on July 25th as on December 25th, our support of our neighbors, in our schools, in faith communities, and in standing up for others is always needed, no matter the season.
Happy Giving Tuesday (and Giving Season). Intentional and organized giving is rewarding. Build a sustainable, organized habit of giving and you will feel more in control of your finances, less stymied by paper and digital clutter, and less likely to feel burned out.
Keep the spirit of giving alive in a way that uplifts you.
Paper Doll Shares How To Select a Shredder, Shred Responsibly, and Save

Much of the following post originally appeared in 2021 and has been updated for 2024 with current product links and shredding discounts.
Klop. KaKLOP! Klunkety klunkety. KaKLOP! Grrrrrr uggggggg. KaKLOP!
No, unlike the officer at U.S. Strategic Command (STRATCOM), I haven’t let a tiny human take over my keyboard. The above is a close approximation of the sound my shredder made last weekend when, after two decades of faithful service and about halfway through shredding documents no longer necessary for tax time, it gave up the ghost.
At first, I thought I might have just fed one too many staples into the grinding teeth of my little document destruction devil. But, when I lifted the shredder from the bin and turned it over, nothing was stuck in the teeth. However, as I shifted the up-ended shredder motor from my left hand to my right, I could hear something sliding back and forth within. Ruh-roh!
Far more curious than mechanically inclined, I took a screwdriver to the whole housing unit, wondering if I might be able to just stick something back in place. (Yeah, go ahead and laugh.) Sadly, I found that a large octagonal metal washer (for want of a better description) had broken completely in half. The wheels on this bus were NOT going to go round and round any longer. I had to buy a new shredder.
DIY SHREDDER ESSENTIALS
Although I haven’t had to purchase a shredder in a long time, this is not my first shredding rodeo. Many of my clients find themselves either buying a first or replacement shredder as part of our work when we’re organizing and purging paper. So at least I knew what I needed to consider.
I hate to be crude, but size matters: the size of your shredder unit, the size of your “shreds,” and the size of the pile (or capacity) you can shred at one time.
Shredder Unit Size
There are three general sizes/types of shredder units: mini, medium, and heavy-duty.
Don’t buy a mini.
Yes, I know, regular readers of this blog recognize that I rarely invoke absolutes; the world is far more grey than black-and-white. However, unless you are buying a shredder for a child, I want to discourage you from buying a mini, or desktop, shredder.
Paper Doll’s Ultimate Guide to Tax-Smart Organizing: 2024

Every few years, I share a series of tax-related organizing tips for readers. Recently I’ve received inquiries from first-time filers asking for how to even begin the process. So, today’s post mixes tax-related news with a larger baseline of how to accomplish preparing and submitting your 2023 tax return.
Note: I’m neither an accountant nor a tax preparer. I don’t even play one on television. But I do help my clients find, organize, and make sense of the documents they need in order to prepare their tax returns.
ESSENTIAL TAX INFO TO KEEP ORGANIZED
Tax Deadlines
The federal Tax Day is April 15, 2024 (unless you live in Maine or Massachusetts, where it’s April 17, 2024).
If you file a (valid) extension request, you must file your tax return by October 15, 2024. Note, you still have to PAY what you (estimate that you) owe by April 15th to avoid a fine. However, if you strongly believe you’re not going to owe anything, you may file late (without filing for an extension) and there’s no penalty fee. But then you’ll also be delaying getting a refund if you’re owed one, so Paper Doll advises against procrastinating.

How To Prepare and File Your Taxes
You have a variety of options for how you prepare and file your federal taxes:
- Prepare your taxes yourself on paper forms. Like a caveman. And you’ll have to do your own math.
- Hire an accountant or CPA firm. You still have to gather all of your forms and your receipts and tell your tax preparer all the wiggly little oddities in your life last year, but you won’t have to do math. The complexity of your return (and how well you organized your supporting document) will determine the cost of the service.
- Visit a tax preparation service like H&R Block or Jackson Hewitt. Find them in independent storefronts or at desks inside big box stores, like Walmart. However, you may want to reconsider this option.
Color Of Change, in collaboration with Better IRS, just released a report called Preying Preparers: How Storefront Tax Preparation Companies Target Low-Income Black and Brown Communities. In it, they cite that many of these companies are unqualified, hiring non-accountant “unenrolled tax preparers,” who are neither credentialed nor certified in tax policy and regulations, and who do not adhere to continuing education requirements — and in 43 states aren’t even obliged to meet basic standards!
As such, many of these unenrolled preparers have been found to have made excessive errors; indeed, one study by the U.S. Government Accountability Office (GAO) found that only 10% of preparers at large tax prep chains calculated tax refunds correctly! Additionally, many of these companies are preying on low-income and minority taxpayers by charging for advances on refund checks, and promoting unnecessary tax products and high-interest refund anticipation loans.
- Use online tax preparation software, like TurboTax, H&R Block Online, TaxAct, Cash App Taxes, and Free Tax USA. They’ll hold your hand through prompting questions and you won’t have to do the math, but you’re ultimately responsible if you misunderstand a question or make an error. And it can be pricey!
The IRS already receives copies of our income information directly from employers, banks, investment companies, etc., so why do we have to do all of this? And why is it so expensive, especially for those who don’t even owe? Because these companies lobby and bribe — ahem, sorry, contribute — to congressional representatives’ election campaigns to prevent the federal government from creating a free option for all!
More Affordable Filing Options
The IRS estimates that Americans spend an average of $250 to prepare and file their taxes, but there are options for lessening that burden.
- If you are age 60 or older, make $64,000/year or less, are disabled, or need language support, you can get free help from IRS-certified volunteers in the Volunteer Income Tax Assistance (VITA) or Tax Counseling for the Elderly (TCE) programs.
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- Find VITA and TCE program locations at the IRS locator page.
- Seek related help from the AARP Tax-Aide Service.
- The United Way can connect you to preparation and filing assistance via MyFreeTaxes.
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- If you’re a member of the military (or a military family), you can prepare and file a federal return and up to three state returns, for free, through MilTax. Eligibility requires that you are:
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- An active-duty service member, and/or their spouse and dependent child(ren).
- A member of the National Guard and National Guard Reserve (no matter your activation status).
- Survivors of deceased active-duty service members, National Guard, or National Guard Reserve members (without regard to activation status or conflict).
- Honorably discharged, retired service members from all branches, including the Coast Guard, if you’ve been discharged within the past 365 days.
- Designated family members of service personnel who’ve been authorized to manage the eligible member’s financial affairs during deployment. Similarly, any designated family member of a service member deemed “severely injured” and not capable of handing their own financial affairs.
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- If your 2023 adjusted gross income (AGI) was $79,000 or less in 2023, you can use the government’s Free File program. Here, the IRS partners with online tax preparers each year and eligible users (for 2023 filing, that means those with an adjusted gross income (AGI) of $79,000 or less) can file federal taxes with no fee. (State tax costs vary.)
However, the contracted companies change year-to-year, so if you prefer to maintain your data in your account, making it easier to do year-to-year comparisons and be prompted to recall charitable recipients and sources of W2s, 1099s, etc., next year you may have to decide between switching to a new program partner or paying for what was once free.
Some past participating partners in the Free File program have been problematic. The Federal Trade Commission (FTC) found that TurboTax engaged in deceptive advertising (forcing up-selling), and investigated H&R Block for improperly handling and deleting customer data (as well as for deceptive advertising).
Unsurprisingly, both companies have supported legislation to ban the IRS from offering free tax filing services.
- If you qualify, try the US government’s new Direct File trial program. Only 12 states (Arizona, California, Florida, New Hampshire, New York, Nevada, Massachusetts, South Dakota, Tennessee, Texas, Washington, and Wyoming) are participating in this trial effort.
Direct File eligibility is limited to those with income from employment (reported via W2), unemployment compensation, or from Social Security, so self-employed individuals, gig workers, and those with pensions can’t use it. To try Direct File, you have to take the Standard Deduction and can’t itemize. (You can have up to $1500 in interest or savings bond income, but not earnings through payment apps, rent, or prizes. Wages are limited to $200,000, or $125,000 if you are filing Married Filing Separately.)
Unfortunately, Direct File’s future is uncertain. The Biden administration allocated $15 million from the Inflation Reduction Act for IRS to evaluate the viability of a a free online tax preparation and filing service, with $80 billion apportioned for over the next decade. However, Congress’ debt ceiling agreement “clawed back” some of those funds.
Special K: It’s Not Just for Breakfast Anymore
Do you have an online platform on Etsy or eBay, or use a payment platform to sell through your website? Then you may have heard rumblings about the 1099-K form finally getting the $600 rule up and running. Well, it’s been delayed again.
The rule is designed so that anyone who receives money from a third-party network like Venmo, Cash App, PayPal, Square, or Stripe for having made $600 or more in sales for either goods or services would receive a Form 1099-K by late January or early February (when we’re supposed to get all of our 1099s). But the IRS has repeatedly delayed implementing the rule, so some people have received 1099-Ks and others haven’t, causing confusion.
So, if you got a 1099-K, check to make sure the numbers match the income you believe you received. (If there’s a mismatch between your records and the form, contact your financial network and correct it before you file your return.)
If you didn’t get a 1099-K, that doesn’t mean that you can fib to the IRS! You must report all taxable income, even if someone who was supposed to send you a form didn’t do their job.

Photo courtesy of Chris Potter/CCPix at www.ccPixs.com under CC 2.0
START THE TREASURE HUNT
Know What You Spent
Start by gathering expense information, like:
- receipts for tax-deductible purchases — check paper receipts as well as email confirmations of purchases
- statements or summaries from ongoing accounts. (On Amazon, select the year from the drop-down under Your Orders in your account. Don’t forget to check the tab for digital orders, too!)
- online financial dashboards — Mint closed in March, so plan to find a new dashboard like Quicken Simplifi, Empower, or YNAB.
Gather tangible information in a folder labeled Tax Prep 2023, or use something like the Smead All-In-One Income Tax Organizer. Just having it all together will be the first step toward tabulating the correct amounts.

Gather Ye Forms
Most of the essential data you’ll enter into your tax return will come as supporting documents called information returns. These are sent to you by others — employers, banks, brokerage houses, schools, casinos, etc. — and they’re required to mail them by January 31st! That scary-but-official mail you threw on top of the microwave the week before Valentine’s Day? Move the oven mitts and get looking!
The rest of this post is an update of past year’s posts, laying out the different kinds of forms you might need.
MONEY YOU RECEIVED
W-2 (Wage and Tax Statement)
If you were an employee at any point in 2023, your employer should have sent one W2 copy to you and one to the IRS, reporting how much you were paid (in wages, salaries, and/or tips). If applicable, it should also indicate how much money was withheld from you and paid to federal and/or state governments for taxes and FICA (Social Security and Medicare).
Federal, state, and local taxes, FICA, unemployment insurance, and a few other withholdings are considered statutory payroll tax deductions. Statutes (that is, laws) require them, so your employer can’t just blow off withholding this money and sending it to the right agencies.
Sometimes, a court might rule that an an employee’s wages may be garnished, but this has nothing to do with sprigs of parsley. People behind on child support payments or who owe money in lawsuits may have money removed from their earnings, before it ever gets to their paychecks, to ensure it goes directly to whomever is owed.
Your W-2 may also report voluntary payroll deductions. These are amounts withheld from your paycheck because you’ve granted permission. These may include your portion of health and life insurance premiums, contributions to your 401(k) or other retirement fund, employee stock purchasing plans, one-time or ongoing donations to the United Way, union dues, etc.

Photo by The New York Public Library on Unsplash
Did you get multiple copies of the same W-2? Employers submit copy A directly to the Social Security Administration for FICA and keep copy D for their own records. Copies B and C are for you (the employee) – you send one to the IRS with your federal tax return and keep one for your own records. Then, they provide copies 1 and 2 to file with applicable state or local tax authorities. (I’ve never figured out why W-2 copies 1 and 2 aren’t called E and F. Did the same person who came up with this decide that bras should be sized as A, B, C, D, DD, DDD, F, FF, and G, skipping E entirely?)
I've never figured out why W-2 copies 1 and 2 aren't called E and F. Did the same person who came up with this decide that bras should be sized as A, B, C, D, DD, DDD, F, and G, skipping E entirely? Share on XIn theory, a W-2 should be mailed to the address listed on your W-4. (Don’t be confused. The W-4, is the form that tells your boss how much to withhold based on your number of dependents you have.)
Smaller companies may just hand you your W-2 instead of mailing it, but if your W2 is missing, consider:
- Did you change employers last year? You should have received W-2s from each employer. (If you changed jobs at the same company, you’ll receive one W-2 from each employer, not one per position. If you changed companies within a larger corporation, though, you may get one for each.)
- Did you change addresses since you filled out your W-4? There’s only so much a former employer will do to track you down to give you your W-2. Keep the Madge in HR updated!
Don’t assume that if you don’t have your W-2, then nobody knows what you made. Remember, the IRS got Copy A. The IRS knows what you made, so be sure you do, too! (If your former company went out of business or is otherwise not returning your calls, the IRS has a procedure to allow you to file your taxes in the absence of a W-2.)
Examine your W-2 it carefully. Do the numbers seem right? Compare them to the final pay stub you got for last year. Calendar years may end mid-week (or even mid-pay period), so the numbers won’t correspond perfectly, but they’ll be close enough for you to spot if something is seriously wrong. The sooner you call your employer’s attention to an error, the sooner you can prepare your return.
W-2G (Certain Gambling Winnings)

Gambling Photo by Aidan Howe on Unsplash
The W2G is the freewheeling cousin of the W-2. While a W-2 is for money you make while working, the W-2G is what you get while playing. If you win more than $600 in any gambling session at a casino – whoohoo! – the “house” should request your Tax ID (generally your Social Security number) and either prepare a W-2G on the spot or send it to you in January.
Casinos aren’t interested in keeping up with your losses, just your winnings, so they only tell the IRS about what they paid you. If you gamble and want to deduct losses, the IRS requires you have provide receipts, tickets, statements, or other records to support both your winnings and losses.
1099s (Income)
A 1099 is a form that basically says, “Hey, we paid you some money for something, but you weren’t an employee.” You get a copy; the IRS gets a copy. Easy-peasy.

There’s not just one type of 1099; actually, there are 22 different kinds of 1099s. Some of the more common are:
This form reflects the interest income you receive from interest-bearing savings and checking accounts, money market bank accounts, certificates of deposit, and other accounts that pay interest. It also notes whether foreign or U.S. taxes were withheld and if there were any penalties assigned for early withdrawal from an interest-bearing account.
Internet-only banks may require you to log into your account to get your 1099-INT, so don’t count on it coming by mail. If you received less than $10 in interest, your bank may not send a 1099-INT.
Do you own stock or other taxable investments? This form indicates the dividends or capital gains you received as an investor. Your broker, plan services company, mutual fund company or other type of investment company will send this form. Not all dividends are created equal; ask your tax professional if you have any that seem unusual or complicated. Whether you receive dividend checks or your dividends are held in a DRIP (a direct re-investment plan), if you didn’t earn at least $10 in dividends, you are unlikely to receive a 1099-DIV.
This random form is subtitled “Certain Government Payments” and can cover everything from state unemployment compensation to tax refunds, credits, and offsets at the state and local level. It can also be used to report payment of taxable grants, agricultural payments, and other nifty things where a state or local government gives you money.
This new(ish) form replaces some uses of the 1099-MISC. If you’re self-employed (a freelancer, an independent contractor, etc.), you should get a 1099-NEC. However, 1099-NEC just started in 2021, so people unfamiliar with it may send you a 1099-MISC by mistake.

Another problem is that even if someone paid you for doing work as an independent contractor, they may not know they should be sending you a 1099-NEC. So, if you are self-employed or irregularly employed, it’s essential to keep track of your own incoming revenue. Otherwise, if the person who paid you ever gets audited, it could trigger some messy situations for you, too.
Now that this form no longer covers income for freelances and independent contractors, it’s truly more “miscellaneous.” Seriously, it’s the junk drawer of tax forms!
It’s used to report payment of royalties, broker payments, certain rents, prizes and awards, fishing boat proceeds (yes, really!), crop insurance proceeds, and some payments to attorneys that wouldn’t be reported on a 1099-NEC, like if you received a settlement and had to pay an attorney a portion of it. In general, once people get used to the 1099-NEC, you’ll only get this miscellaneous form to report truly miscellaneous payments.
SSA-1099 (Nobody knows why the numbers and letters are reversed on this one form! It must be done by the same people who label the copies of W-2s and bra sizes!)
If you receive Social Security benefits, you should receive an SSA-1099. (Non-citizens living outside the US, like widows/widowers receiving spousal Social Security benefits, may get a SSA-1042.) The 1099-SSA tends to come on a long form, folded and sealed such that it makes its own envelope. It may look like junk mail, so watch out and replace it, if necessary!
A 1099 doesn’t always indicate that you were literally paid money. For example, a 1099-C indicates that someone forgave a debt, like a mortgage or a credit card balance. You may owe tax on forgiven debts, and the 1099-C alerts the IRS that since you didn’t pay money owed, and got to keep it in your pocket, it’s as if you received money.
1099s sometimes hide in plain sight. Sometimes, instead of sending a 1099 in a separate envelope, a bank or brokerage house may include a 1099 form in the same envelope — sometimes perforated at the bottom of a quarterly or end-of-year financial statement. Be sure to check all that boring-looking official mail. Brokerage houses often sent multiple forms as a “combined 1099,” scrolling across multiple pages. Check the reverse sides of forms, in case you’re missing one.
MONEY YOU PAID
1098 (Mortgage Interest)
A 1098 is not a 1099 with low-self-esteem. The vanilla, no-frills 1098 reflects the interest you paid on your mortgage, which is generally deductible on your federal taxes. Renters don’t get 1098s; neither do homeowners who’ve paid off their mortgages.
There are also sub-types of 1098s for things other than interest on property loans:
- 1098-T indicates tuition you paid; you’ll get this from a college or training school.
- 1098-E shows you’ve paid interest on a student loan and will come from your lender.
- 1098-C indicates the donation value of a car, boat or airplane by fancy-pants, monocle-wearing Mr. and Mrs. Thurston Howell.

Photo by Diego F. Parra from Pexels
1095-A (Health Insurance Statement)
The 1095-A is also called the Health Insurance Marketplace Statement. If you purchased coverage through a state or federal exchange, this helps you determine whether you are able to receive an additional premium tax credit or have to pay some back.
Related forms include the 1095-B (supplied by companies with fewer than 50 employees), detailing the the type of coverage you had, the period of coverage, and your number of dependents, so you can prove you had the Minimum Essential Coverage (MEC) required by law. A 1095-C is similar, but for employers with more than 50 employees.
SPECIAL 1040 FORM FOR SENIORS
Are you a senior? If you are over 65, instead of filing the standard 1040 form, you can file the 1040-SR. The main benefit is that this form, when printed, uses a larger font and provides easier readability.
FINAL THOUGHTS
If you receive a mysterious form, or have questions about how to use a form, the IRS has a surprisingly easy Forms, Instructions and Publications Search. Again, I am a Certified Professional Organizer, not an accountant, so please address any concerns to a tax specialist.
Making sure you have all of the necessary forms in hand will make it much easier to prepare your tax return. Once you file your taxes, make a list of all the forms you received this year, and tuck that list into your tickler file for next January. Check off each form as it arrives, and you’ll have a better sense of when you’ll be ready to start working on your 2024 taxes in 2025.
24 Smart Ways to Get More Organized and Productive in 2024

Happy New Year! Happy GO Month!
January is Get Organized & Be Productive (GO) Month, an annual initiative sponsored by the National Association of Productivity & Organizing Professionals (NAPO). We professional organizers and productivity experts celebrate how NAPO members work to improve the lives of our clients and audiences by helping create environments that support productivity, health, and well-being. What better way to start the year than creating systems and skills, spaces and attitudes — all to foster a better way of living?!

To start GO Month, today’s I’m echoing Gretchen Rubin’s 24 for ’24 theme that I mentioned recently, and offering you 24 ways to move yourself toward a more organized and productive life in 2024. There are 23 weekdays in January this year, so if you’re feeling aspirational and want to conquer all of these, you can even take the weekends off as the last item is a thinking task rather than a doing task.
I broke these organizing and productivity achievements down by category, but there’s no particular order in which you need to approach them, and certainly you don’t need to accomplish every one on the list, in January or even all year. Jump in and get started — some only take a few minutes.
PUT LAST YEAR AWAY
1) Make many happy returns!
Did you know that shoppers will return $173 billion in merchandise by the end of January? Chances are good that you (or someone for whom you oversee such things) got gifts that need to be returned.
Don’t put it off. The longer you wait, the more clutter will build up in your space, and the more likely you will be to suffer clutter-blindness until the return period has expired. Most stores have extended return policies during the holidays, but they can range upward from 30, depending on whether you have a gift receipt.
The Krazy Coupon Lady blog reviews the 2024 return deadlines for major retailers. She notes that you’ll get your refunds faster by returning items to the brick & mortar stores rather than shipping them back. You’ll also save money, because some online retailers charge a restocking fee.
2) Purge your holiday cards.
While tangible greeting are getting fewer and farther between, you probably still got a stack. Reread them one last time, and then LET THEM GO.

Did Hallmark or American Greetings do the heavy lifting, and the senders just signed their names? Toss them into the recycling bin. Paper Doll‘s grants you permission to only save cards with messages that are personal or resonant.
If they don’t make you cry, laugh, or go, “Ohhhhh,” don’t let them turn into the clutter you and your professional organizer will have to toss out years from now when you’re trying to downsize to a smaller home! It’s a holiday message, not a historical document; you don’t transcribe your holiday phone conversations and keep them forever, right?
The same goes for photos of other people’s families. You don’t have to be the curator of the museum of other people’s family history; let them do that.
3) Update your contacts.
Before you toss those cards, check the return addresses on the envelopes and update the information in your own contacts app, spreadsheet, or address book.
Next, delete the entries for people you’ll never contact again — that ex (who belongs in the past), that boss who used to call you about work stuff on weekends (ditto), people who are no longer in your life, and those who are no longer on this mortal coil.
If you don’t recognize the name of someone in your contacts, Google them or check LinkedIn (is it your mom’s doctor? your mechanic?) and if you still don’t know who it is, you’re obviously not going to be calling or texting them. Worst case scenario, if they text you, you can type back, “New phone, who dis?”
BOX UP YOUR INBOXES
4) Delete (most of) your old voicemails.
How often do you return a call only to hear, “The voicemail box is full and is not accepting messages. Please try again later.” When someone calls you and requests you call them back but their voicemail is full, it’s frustrating because it makes more labor for you.
Do you assume that it’s a cell phone and text them? (I believe texting strangers without permission is a breach of etiquette.) Plan to call back later? Assume that they’ll see the missed call and get back to you, starting another round of phone tag? ARGH!
Dial in to your voicemail and start deleting. Save phone numbers for anyone you’ll need to contact and log anything you may need to follow up on. But unless you’re saving a voicemail for legal purposes or because you can see yourself sitting in an airport, listening to a loved one’s message over and over (cue sappy rom-com music), delete old voicemails.
If you’ve got a landline, clear that voicemail. If you’ve still got an answering machine, how’s the weather in 1997? Yeah, delete old messages.
Smith.ai has a great blog post on how to download important voicemails (from a wide variety of phone platforms) to an audio file. Stop cluttering your voicemail inbox!
5) Clear Your Email Inboxes
Start by sorting your inbox by sender and deleting anything that’s advertising or old newsletters. If you haven’t acted on it by now, free yourself from inbox clutter! Delete! Then conquer email threads, like about picking meeting times (especially if those meetings were in the past).

Take a few minutes at the end of each day to delete a chunk of old emails. To try a bolder approach, check out a classic Paper Doll post from 2009, A Different Kind of Bankruptcy, on how to declare email bankruptcy.
6) Purge all of your other tangible and digital inboxes.
Evernote has a default inbox; if you don’t designate into which folder a saved note should go, your note goes somewhere like Paper Doll‘s Default Folder. Lots of your note-taking and other project apps have default storage that serves as holding pens. Read through what you’ve collected — sort by date and focus on the recent items first — and either file in the right folders or hit delete!
Walk around your house or office and find all the places you tend to plop paper down. Get it in one pile. (Set aside anything you’ll absolutely need in the next few days to safeguard it.) Take 10 minutes a day to purge, sort, and file away those random pieces of paper so that you always know where they are.
HIT THE PAPER TRAIL
7) Embrace being a VIP about your VIPs.
You need your Very Important Papers for all sorts of Very Important Reasons. If the last few years have proven anything, it’s that life is unpredictable, so we need to find ways to make things as predictable and dependable as possible.
Yes, putting together essential paperwork isn’t fun. It’s boring. But you want it to be boring. The more boring your vital documents are, the more it means there will be no surprises for your loved ones in troubling times (like during and after an illness, after a death, while recovering possessions after a natural disaster) or even when you’re just trying to accomplish something like getting on an airplane.
Start with these posts, then make a list of any document you already have (and where it is), and another list of what you need to create, and plan meetings with your family and a trusted advisor to set things in motion.
How to Replace and Organize 7 Essential Government Documents
How to Create, Organize, and Safeguard 5 Essential Legal and Estate Documents
The Professor and Mary Ann: 8 Other Essential Documents You Need To Create
Paper Doll’s Ultimate Guide to Getting a Document Notarized
Paper Doll’s Ultimate Guide to Legally Changing Your Name
A New VIP: A Form You Didn’t Know You Needed
8) Create your tax prep folder now so you’ll be ready for April 15th.
Do you toss non-urgent mail on top of the microwave? Might those important 1099s and 1098s and 1095-A and W-2s get lost? Don’t lose deductions, pay more taxes, or get in trouble with the IRS!
By the end of January, you’ll start getting tax documents in the mail. Pop them in a folder in your financial files or in a dedicated holder like the Smead All-in-One Income Tax Organizer.




















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