Pain-free Preparation for Tax Season

I am not a tax professional. I can’t help you file your taxes.

I can, however, help you set up a system that puts the necessary information at your fingertips when it comes time to either file them yourself or take them to your tax professional. It involves a little effort as the year goes along, but if you do it right, it shouldn’t take more than a few minutes here and there to avoid panic, frustration, and overwhelm come tax time.


Step 1: Make folders

  • A physical folder to hold your paperwork (cheap paper thing bought on back-to-school clearance works great.)
  • Electronic folders on your computer (I have a folder marked TEMPLATE, with sub-folders for charitable donation receipts, HCRA receipts, and business receipts; each year I make a copy of the root folder, change the folder name to the year, and have everything set to go with minimum effort.)
  • An envelope for receipts (I realize it’s not technically a folder, but it serves a similar purpose.)


Step 2: Make a recurring list of forms to collect/actions to take

I do this in Toodledo because Toodledo saves my brain. I set each form/action as a task, due January 15th, repeat yearly from completion date, and in the notes section I list the URL I need to visit to get the form (along with instructions if the site is difficult to navigate).

My list looks like this:

  • Taxes – mortgage
  • Taxes – student loan
  • Taxes – W-2 (company name – separate task for each)
  • Taxes – 1109 (company name – separate task for each)
  • Taxes – proof of child residency
  • Taxes – proof of insurance
  • Taxes – calculate business deductions

Yours may or may not look vastly different, but you can look through last year’s forms to figure out what you need.

You could do the same with a sheet of paper in your tax folder or a .txt file in your TEMPLATE folder, if that’s more your style.


Step 4: Stay on top of it

Here’s where the maintenance comes in, but I’ve made all this part of my routine and barely notice the time it takes.

  • When you get a receipt you need to keep, mark it clearly before you leave the store. I have a highlighter/pen combo in my purse for this, and it only takes a few seconds to scribble a category at the top, highlight the relevant bits, and stuff it in the envelope I mentioned above.
  • If you have recurring payments on your credit card (charitable donations, web hosting fees, etc.) make it part of your monthly bill-paying routine to check your statement for these and obtain an electronic receipt. (You could even make a Toodledo task for it!)
  • Start an Excel spreadsheet, and note deductions monthly. List date, amount, store, description, and category (postage, legal fee, etc.)
  • Note any mileage driven for business purposes. My tax specialist wants total miles driven, mileage on December 31, and total business miles driven. I set up a simple formula on my sheet to calculate it for me.
  • If you need proof of child residency, keep an eye out for something useful as the year goes by that has your child’s name and your address. I used an appointment reminder postcard from the dentist.
  • Likewise, anything else relevant to your situation. As soon as you have it, catalog it.
  • BONUS: If you drive somewhere to have your taxes done, keep a copy of the driving directions in your tax folder so you don’t have to look them up every year.


Step 5: Find a tax professional you love

I know many people who file their own taxes with confidence. If that’s you, great! I will admit that while I’m clever with money, tax laws change so often that I am not one of those people. I’ve taken my taxes to Fox Tax for years and have only excellent things to say about them. They put out a brilliant tax organizer .pdf every year that is a breeze to fill in with the data I’ve kept organized. They let me work with them over e-mail (files transferred through a secure online portal), which is awesome because I’m not taking up a time slot someone else needs, it saves on gas, I don’t have to arrange child care, they can work on my stuff when they have an open spot, and I don’t have to get out of my pajamas.


Do you have any tips or tricks you use to make your tax preparations easier? Let me know in the comments!

For the Love of Lists: the Wonders of Toodledo


I’d like to talk about the one thing that makes parenting, household management – and indeed, my very sanity (what remains of it) – possible: lists.

I love lists. Grocery lists, errand lists, project lists, sub-lists of the steps for various projects on various lists. When a day is extra frazzled, lists keep me centered, and there’s no feeling quite like getting to scratch a line through a task. (Hands up if you’ve ever written something on a list just to cross it off. I know I have, and it absolutely counts!)

Maybe you have the same problems I do, though. Lists wander off. They get so many items scratched off (if you’re lucky!) that it’s hard to parse them at a glance. They don’t get finished, so you have to make a new one for tomorrow. It isn’t hard for lists to become a time sink, even if they’re a necessary one.

Enter Toodledo.

I’ve tried a few online list apps, but Toodledo won my heart (and brain). Here’s why:

  1. It’s Free
    Let’s face it, free is the perfect price for most of us. Yes, there’s a paid version that is more robust, and perhaps you’ll find it’s worth it, but for my needs the free version works great.
  2. Notes Section
    Every task you enter has a section for notes. It’s a great place for grocery lists, phone numbers, directions to a party, or any other relevant info.
  3. Scheduling
    You can set due dates on things, even if what you mean by “due” is “I really hope I get to this today.” If you don’t, it’s easy to change the due date to the next most likely opportunity.
  4. Recurring Tasks
    This is the one that really won me. There are so many adult tasks that are important but only happen occasionally: change the furnace filter, schedule the kid’s well child appointment with the pediatrician, dust the ceiling fan, order heartworm medicine for the cats, etc. Every time I do something of that sort, I enter it as a task, set the recurrence frequency, and release it from that cloud of thoughts that ambushes me at one in the morning when I’m trying to sleep. The options go from as simple as daily/monthly/quarterly/etc. to things like “every weekday” or “every Tuesday and Thursday.”
  5. Sorting
    Toodledo lets you create and assign folders. Characters To Level Up, Projects, Responsible Adult Crap… whatever covers it for you. You can also define/sort by context, location, and several other fields. I mostly use folders, but I’m sure others would find the additional fields insanely handy.
  6. Add Multiple Tasks
    If you have several tasks that need to be entered with the same folder, due date, etc., there’s an option to add multiple tasks at once. I’ve found this especially handy when listing component parts of a project.

The really great thing about this, though, is that with a little creativity you can make anything part of it.

For example, I have a folder for birthdays and other important dates (*cough* release date of the next Star Wars movie *cough*). For gift-giving occasions, I have a separate task set a week or two ahead to remind me to shop for a present. I keep a list of gifts given and ideas for the future in the notes section. This is especially handy if you, like I, like giving books but can never recall what you’ve given to whom.

Also, I have a folder for tasks related to performing at the Minnesota Renaissance Festival. I have several tasks set to weekly (wash garb, pack garb, pack food, etc.), some set to yearly (pack med kit, pack bug spray/sunscreen, condition boots at the end of the run…), and one for the expiration year for my ID badge so I know when I need to send a fresh picture to The Powers That Be. It’s also a great place to note any costume repairs or necessary accessory replacements/additions so there are no rude surprises the night before Opening Day. I haven’t gotten involved in the convention scene, but I imagine something similar might be useful for those.

It does take about a year to get it to auto-pilot status, but that’s more a function of writing tasks down as you encounter them rather than any issue with the software itself. If you have a calendar or planner with tasks that you copy from one year to the next, your setup could be significantly faster than mine was.

So, there you have it: my secret thing that makes all things possible. I hope it helps you as much as it helps me!