My Top Tips for How to Stop Procrastination This Tax Season

This is a sponsored conversation written by me on behalf of TurboTax. The opinions and text are all mine.

Throughout my life, one of my most tenacious bad habits has been procrastination. In high school, I always left assignments ’til the last minute, often waiting until the day before a project was due to begin it. In college, my middle name might as well have been ‘Extension’, since I consistently found myself writing term papers even after I’d already left campus for the holiday break! And in my adult life, the prices I’ve paid for my procrastination have run the gamut from thousands of dollars in fines for unpaid parking tickets, to the crippling emotional anguish of carrying a giant monkey on my back. Plus my middle name still may as well be ‘Extension’, because I have literally never once filed my taxes without needing one! But in the past year, I’ve been slowly yet surely winnowing away at my procrastination tendencies using a few mental tricks that get to the heart of why I leave things to the last minute. The changes have been small but impactful, so this tax season I’m applying the same tricks to the filing process so that I can actually complete my return early this year—and TurboTax is the perfect partner in tackling the tax procrastination habit once and for all!

Trick #1: Chip the Iceberg into Ice Cubes. My ability to see the big picture serves me well in my job—its essential in the formulation of a holistic decor vision, for example—but it also leads to a sense of overwhelm when I embark upon a new project and stare in horror at the massive undertaking that awaits me. But as my ex-mother-in-law used to say, “Little by little by little by little by little, big things get done!” So now, when I start a new design project, I have a template for my process. Kick-off call with the client? Check! Pull inspiration images? Check! Draw up floor plan and source pieces that fit the aesthetic and required dimensions? Double check! Breaking my taxes down into similarly manageable chunks (tally receipts! locate last year’s return! track down W-9’s from all my subcontractors) is essential to making them feel approachable. Fortunately, TurboTax is set up exactly for that type of stop-and-go workflow, since the software prompts you through the whole process with bite-sized questions. You can save your progress and return to it at any time, which is where my second trick comes into play…

Trick #2: Just. Spend. Five. Minutes. Almost always, doing the thing I’m avoiding is never as bad as the stress of anticipating doing it. I have an active imagination—again, a valuable trait in my profession!—that magically transforms the simplest endeavor into one of epic proportions. Practicing the piano isn’t just practicing the piano, it’s Mastering the World’s Great Compositions. Doing my taxes isn’t just doing my taxes, it’s Assessing My Worth As a Human. But if I’ve completed Trick #1, then I have a series of tiny, impersonal tasks that I can tackle in just five minutes apiece—and I dive into them by reminding myself that five minutes out of life is nothing. “Just set your timer for five minutes and play the C major scale, Anne. You don’t have to do anything more than that if you don’t feel like it. What’s five minutes out of your day, really?” Or, in the case of the TurboTax returns filing system, “Just answer tax questions for five minutes. They’re in plain English. You barely have to think about them. What’s five minutes of mindless scrolling? You do it on Instagram all the time!” The TurboTax app makes it even easier to check those questions off, since picking up the phone and tapping at our screens has become a second-nature activity for most of us! The secret here, of course, is that once I get started, I realize how easy and satisfying the task at hand is, and I end up plowing through more than just the five minutes I promised myself I’d do!

Trick #3: Enlist support. This one has been the hardest for me to learn, but also the one that’s made the biggest difference in ending my procrastination habit. Because I’m a perfectionist, I get bogged down in the many decisions and unknowns that are inherent to any new project—and I tell myself that the only “right” way to address them is to do it myself. Then, I get so caught up in each detail that I make zero progress at all, which is definitely the worst possible (non)outcome! So wherever I can these days, I delegate. That inspiration Pinterest board for a new design project? I have the client start it and then I jump in and flesh it out! Setting the timer to practice piano for five minutes? I ask Ivan to set his timer, then hold me accountable to sit down and play for the duration. As for my taxes, I found a virtual assistant who I paid a small hourly wage to sort my expense receipts and enter them into a spreadsheet (best $50 I ever spent!). Plus with the new TurboTax Live feature, I can do my taxes using TurboTax before having a one-on-one review with a TurboTax CPA or EA before I file! Even better they, can sign and file for you if you choose. I get live, on-demand tax advice from an experienced tax expert, one who can handle even complex situations like self-employment or multiple businesses. With the screen sharing feature they can view my unique situation as I’m seeing it, and they can catch any write-offs or deductions I may have missed so that I can get my maximum return. It’s just like having your very own tax hero! Oh, and I can do it from home in my PJ’s—which means that deciding what to wear when I leave the house is one less thing I have to worry about! Ha!

My anti-procrastination tricks definitely are not a foolproof system. As I mentioned, my tendency to leave things to the last minute is an ongoing battle. But it is nice to have doable, concrete techniques for eroding the habit away one day at a time; and the more I do these behaviors, the more they self-reinforce so I want to keep doing them. I can only imagine how empowering it will be this year not to have to file for a tax extension! And moving forward, I’ll be using TurboTax Self-Employed, which proactively uncovers business expenses by securely gathering and automatically scanning bank accounts and credit card transactions and recommending potential deductible business expenses. (Imagine that, procrastination prevention!) The thought of spending the next six months not worrying about an impending tax deadline is enough to inspire me to set my timer for five minutes and dive into my tax season to-do’s right now! Just after I make a cup of tea, do the dishes, and scroll through Instagram, that is. 😉

Photos: Eslee.