Three simple ways to save time on tax day

Saved you some time.
Saved you some time.
Image: Reuters/Tim Wimborne
We may earn a commission from links on this page.

The tax man cometh. For millions of Americans, this means gathering the alphabet soup of W-2s, 1099s (MISC, INT, and DIV), K-1s, and charitable contributions. It also means many encounters with a major digital buzzkill: the pain of remembering (or digging up, or resetting) seldom-used passwords.

Yes, this annual ritual will require you to log into dormant bank accounts, jump through user name and password resets, SMS authentications, and ridiculous security questions (“Which actor/actress do you most resemble?”) only to create another immutable login credential that you will unquestionably forget by next tax season.

Adding insult to injury, the big day exposes other breakdowns in our workflow. For example, how do you digitally organize loose sheets of paper? (Sorry, your tax planner probably won’t accept an iPhoto of your W-2.) And how come, despite knowing about this deadline a year in advance, it always seems to catch you off guard?

Despite the 85% chance that you will either owe nothing or will get a refund, we all tend to fear this day, often for its logistical challenges alone.

Here are three tips to help you save time, streamline your workflow, and savor the process of collecting your refund should one be awaiting you.

1. Just get a password manager already

This isn’t the place to lecture you about the dangers of using dumb passwords, or reusing the same password on every account. Instead, I’ll pull on your productivity heartstrings and appeal to one of the gurus of management efficiency. In his book High Output Management, Andy Grove, the founder and former CEO of Intel, directs managers to look for “the most difficult, sensitive, or expensive task” or ”limiting step” in your production flow. For many of us, the inability to keep track of all our logins is a limiting step. While managing logins might not be intellectually difficult or financially expensive, I can tell you, as someone who has 116 logins, it is a cognitively difficult task that’s costly in terms of your time and sanity. 

In an era where even seemingly innocuous security measures can lead to liquidated bank accounts, eradicating this limiting step while safeguarding your financial assets is a win-win. There are a variety of password managers to choose from, like Dashlane, Lastpass, Keeper, and 1Password. They aren’t the easiest to set up, but when you get frustrated, just remember the promised nirvana of never needing to reset a password again!

2. Digitize the paper trail

I’ve tried sending my accountant photos of my W-2s. It doesn’t work. He always responds by asking for a PDF. You might not have known that the free version of Dropbox has a built-in scanner that uses your camera to capture any document. But there’s more—it also will automatically adjust the lighting, margins, and text to “convert” it into a document equivalent and then save it as a PDF (in your Dropbox, obviously). A bonus feature is its ability to aggregate multiple scans into one PDF, so that you can send or upload all your tax documents as one large file.

Don’t dismay, once the fun of Tax Day is gone, you can still continue to use these tricks to capture and store images from notebooks, photos, and whiteboards.

3. Learn to manage projects with really long deadlines

Taxes and to-do lists don’t jive. You’d think that given the long lead time and predictable timing they’d be the poster child for project management. But picture this scenario: On April 15, when you mark the task “File Taxes” as done, a new instance of that task immediately shows up (and nags you for the next 364 days). No thanks. (Note: the deadline for filing in 2018 for 2017 calendar-year earnings is actually April 17, because April 15 is a Sunday and April 16 is a holiday in Washington DC. Still, the same to-do list problem applies.)

A nice, yet surprisingly rare to-do list feature is having a “start date” for tasks, so that long-dated tasks, such as making an appointment for your annual physical or starting preparations for a birthday party, don’t clog up your workflow. Omnifocus (iOS) and 2Do (Android and iOS) are two apps that allow for this.

Another challenge in the tax preparation are tasks which don’t have due dates yet require some kind of accountability. An example of this would be donating used clothes for which you might take a charitable deduction. This task falls through the cracks of not needing a due date (well, technically your deadline is tax day itself, but if you’ve waited until then to start going through your closet, it’s probably too late). What you need instead is a periodic reminder. In the productivity tome Getting Things Done: The Art of Stress-Free Productivity, David Allen recommends checking in on tasks like these as part of a regular “review process.” My longtime favorite productivity app Omnifocus has a built-in feature that helps with this. You get a periodic reminder of “important but not urgent” tasks instead of incessant reminders that become easy to tune out.

Who knew that April 15th (or April 17th as the case may be) could serve as the perfect catalyst for fine-tuning your workflow? In the long run, it might be worth even more than that upcoming tax refund.