Get ready for tax time: I wish this were fun

February 9, 2015

Sigh. Tax time. W-2s, gathering paperwork, financial advisers, time away from work to meet with these people and talk about boring things. None of this is real sexy. All of it’s necessary, right?

You need a plan for the onslaught of tax documents that are hitting your mailbox now. This is the stuff you’ll need handy when you either go see your tax guy (or girl) or you do your own taxes.

Here’s how I handle this:

  1. In the last week of the December of each year, I organize and file all of that past year’s financial documents and store them in my fire-safe file box.
  2. Once that’s done, I label a new folder “Tax Docs {fill in current year}” and put it at the front of my file box that houses my current year’s financial documents (where I file my daily mail, etc.)
  3. As the tax documents come in (those W2s, 1098s, 1099-Gs, etc.), I simply slip them into that handy folder.
  4. When I’m ready to go see Tax Guy, I grab and go.

Penelope Tip: use this as an excuse to buy some zotchy new file folders. Doesn’t hurt to have your tax documents looking pretty.

See Jane Work File Folders

Marci over at Overcoming Busy also did a nice post on Tax Time Tips. You should check out what she’s got to say about it, too.

Sexy? No. Simple? Yes. And with taxes, that’s about as good as it gets.

Originally posted January 21, 2010.


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{ 18 comments… read them below or add one }

Marci@OvercomingBusy January 21, 2010 at 5:43 am

We are sharing a brain!! I would be very frightened if I were you!! :)

Kimberly January 21, 2010 at 10:53 am

I feel fortunate because my dh handles all of our finances; well, except for our investments. I take care of that for the most part. Your method is exactly what he does minus the darling folder. I should tell him that a darling husband should have a darling folder. So–when my friends are belly-aching about their tax preparation–I nod and listen all while being grateful that I don’t have to worry about it.

Jennifer Tankersley January 21, 2010 at 11:15 am

Death & Taxes. While both are inevitable, one you should try to avoid and the other you might as well hit head on (this one is taxes – let there be no confusion :-) I have already been hard at work this month get my bookkeeping in order and adjusting my financial goals and budget for 2010.

carlee January 21, 2010 at 11:16 am

Usually taxes are a breeze for me, I do them online! BUT, last year I worked in 2 different states which makes it a pain! I better get on mine soon! thanks for the reminder!

Amanda @ Serenity Now January 21, 2010 at 1:18 pm

I. Hate. Tax. Time. We have a guy do ours, but I still have to get all the paperwork ready, make copies, etc. Ick. No fun!

Samantha January 21, 2010 at 5:08 pm

Great tips! I’m shuddering at the thought of taxes.

Deren Monday January 21, 2010 at 9:53 pm

I’m amazed each year by the simplicity and power of TaxCut (or TurboTax, I can never remember…)

Year after year I think that my finances will have become too odd to use such simple software, but yer after year I am proven incorrect. Rental properties, S-corps, investment income and expenses, all of it can be accounted for.

On the other hand, being a bit of a financial nerd, I can totally understand hiring this out. But if you want to give it a shot…

Anyone out there had any luck with the purely on-line versions of this software?

Jessica at Lavender and Lilies January 22, 2010 at 3:39 am

Great ideas. I always struggle with keeping up with donations, mileage for work, blah blah so you inspire me to be much more organized.

On another subject, thank you so much for your sweet note and for picking me as one of your favorite blogs! Your note made me feel so great. I try to let my personality come through my blog so that made me feel great. I also do worry that my blog is a “mish mash” so this really increased my confidence about what I blog about. You are awesome and so so sweet!

Meredith Meredith January 22, 2010 at 8:12 am

@Deren: I used TurboTax one year after looking at the software my tax guy used and thinking “it’s basically TurboTax, and I’m paying him $300 for this?”. So, I used TT to prepare and file our taxes myself. And I was careful, and thorough. And I’m kind of not stupid.

And I made an error. One of my investments hadn’t sent me my paperwork on time (it arrived in late April!) and I didn’t know enough to look into it. Total ignorance on my part. I didn’t know that particular investment had tax ramifications.

So we got a scary letter from the IRS and I about peed my pants. Luckily, the problem was easily fixed and involved a very, very small sum of money, but it scared me enough to use my tax guy from now on.

That said, I know a lot of people who swear by TT and do very well with it. I’m just too nervous!

Erin January 22, 2010 at 8:22 am

Last year I purchased beautiful folders from RedStamp ( and it really did make me more excited about filing. I do a lot less filing, however, as I purchased a ScanSnap and use NeatOffice software to make everything digital (the IRS accepts digital copies of receipts). We have always used Turbo Tax, but then last year for the first time, we used an accountant. Heaven!! We saved more than we had with Turbo Tax, and it actually got done! Our goal is to get them everything by the first week of February and check “taxes” off our list.

Meredith Meredith January 22, 2010 at 3:32 pm

@Erin: you are full of the best ideas, my blogging friend. I’m now magnetically glued (is that possible?) to Red Stamp!

Jules January 22, 2010 at 5:47 pm

Oh, I’m dreading taxes this year. This year is the first year we are doing K1s (my business partner and I) and the first year is always the hardest, especially when most tax preparers aren’t accustomed to working with creative businesses.

Jesse January 22, 2010 at 7:13 pm

I am excited to say that we have our taxes finished already. But my husband and I are both self employed so that helps us get them in early. I was just told by a friend that there is an app for logging mileage. I am going to check it out!

Allyson January 23, 2014 at 2:36 pm

Oooooh. Those folders are gorgeous.

I really need to get on top of my paperwork game. Those folders are gonna be my inspiration.

Ana January 24, 2014 at 11:31 am

I do the same thing (“Tax Documents 2014″ is currently in use)…but yet my husband and I procrastinate later and later each year on actually sitting down and plugging the numbers into turbo tax. Once we do it, we realize how simple it was, it only takes a couple of hours, we both have one source of income that is handily dealt with on the W2 and a few small investments that I’ve already got the forms on. Last year we did it April 12th, which is cutting it REAL close for me, I am not a last-minute kind of gal!

Meredith Meredith January 24, 2014 at 11:35 am

Oh, Ana, do I understand! I absolutely hate anything related to taxes. I’m more likely to procrastinate on this than anything else.

Karen (Scotland) June 7, 2014 at 2:13 pm

Ok, this was all double-Dutch to me. :-)
Most tax in this country is dealt with through PAYE (Pay as you Earn) unless one does Self-Assessment (which I do due to rental income). Our tax year runs 6th April – 5th April. Ideally, I would hand in my Self-Assessment 7th April, but we always have to wait for interest and tax statements from banks, which sometimes don’t come out until July. JULY!! How can it take them three months to produce a sheet of paper saying how much interest I earned and how much tax I paid?!

The first couple of years I did self-assessment, I left it all until the April and just put all the paperwork in one folder then sorted it all out. Now, I number receipts, enter them on my spreadsheet and file them in the correct “box” for the form.

I don’t earn enough to pay tax but I figure it’s good practice to do the paperwork thoroughly in case I ever do.

Jolene Rae Harrington February 9, 2015 at 11:41 am

With all the wonderful online tools available, I confess to being obsessed with paper copies of everything. I print out (using recycled paper!) all my online receipts, so I can have the joy (control?) of sorting them manually, making my red check-marks that mean the amount has been added to the correct tax category, and then re-sorting them back in their very pretty file folders. And yes, that means I have plastic crate in the attic that holds all my tax prep info and supporting documents. But I just feel better this way!

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