If life is perfect for you all the time, nothing ever goes wrong, and everything is unicorns 🦄 and rainbows 🌈… this post isn’t for you.

But if you’ve ever had a mountain full of work on your desk and a kid who just upchucked on the kitchen floor while trying to get ready for school, let’s chat. (Note: puke is my personal Kryptonite.)

Basically, life is allll about the unexpected. And sometimes, that unexpected is not so appreciated, but sh*t happens. We’re here, we’re bosses, and we gotta deal with it, there’s really no other option.

4 Tips for Keeping Your Sanity During Tax Season

Tax time can be incredibly stressful, there’s no doubt about it. Whether you are totally on top of it or cramming a year’s worth of prep into the next few weeks… you have to prepare for the unexpected. Basically, you owe it to your sanity to think ahead. 

Here’s a perfect example of what I mean:

In 2014, we got a lot of snow in New York. Like not to be dramatic, but I was convinced the world was ending. And of course, every parent knows what lots of snow means (at least, before virtual learning was a thing)… MANY, MANY SNOWDAYS. ❄️❄️❄️

Awesome for my kids, stressful as hell for me. 

Tax deadlines were approaching quickly, but I had to split my time between being a bookkeeper, personal chef, entertainer, housekeeper, and snow shoveler. It was… not the best start to a new year I’ve had. In fact it was so bad I made this post in my local moms group over on the FB:

But the sorta silver lining from all of that is the pointers I created to help you stay on course next tax season, even when the universe dumps an apocalyptic amount of snow on your life.

What can you do to overcome obstacles and stay on track all season long? Here’s what I suggest:

1️⃣ Start early. This shouldn’t surprise you by now, but expanding your tax season to last all-year long really does alleviate an immense amount of stress. 

2️⃣ Build margins into your schedule. By anticipating that something unexpected will inevitably happen, you can give your schedule and yourself a little much-needed breathing room. A margin will give you that much needed wiggle room. 

3️⃣ Consider not onboarding new clients. Now, this one is completely personal preference, but my team typically does not onboard new clients in January since we always anticipate that month to be busier than usual.

4️⃣ Set up your EOY systems and processes NOW. While everything from this current tax season is still fresh in your mind, create systems and processes you can use to make life soooo much easier next year.

Why It’s Important to Learn from the Losing

I know, I know. This is all good advice in theory, but things happen even to the best of us. 

But when you eventually do come out the other side of a stressful situation, what are you doing to make sure that never happens again?

There’s a common phrase from Einstein, “Insanity is doing the same thing over and over and expecting different results.”

Well… that’s what kinda happens when you don’t sit down and try to learn from your mistakes and make a plan to avoid them in the future.

Conducting an After-Action Review 

So how do you learn from the losing? We use a formal tool called an After Action Review (AAR)

This is a suuuuper powerful tool that you can actually use in many different areas of your life. But for business, it’s great because it allows you to reflect on a bad (or good!) experience in your business soon after it’s happened.

With it still fresh in your mind, you and your team can dissect what went well, what went wrong, and how you can improve next time. Essentially, you’re taking the time to codify what you learned from this experience, so you can repeat successes and avoid failures in the future.

Why is this so freakin’ important? 

Mooooonths go by before you start gearing up for the next tax season. While you probably remember it was stressful, the details are fuzzy and any lessons learned have vanished.

🤔 “I know I said I’d never do this again… but I can’t remember what exactly I was talking about??”

🤔 “Last year, Justine taught me this awesome way to file 1099s electronically, now I can’t remember how to do it.”

🤔 “I can wait to start tax stuff til after the holidays, I don’t think it was THAT bad last year.” (Insert narrator’s voice: It was, indeed, very bad.) 

Soooo yeah. Let’s not do that to ourselves.


This year we’re going to do our best to expect the unexpected and learn from the losing, my friend. And, of course, document our wins so we can keep winning year after year!

Did you find these tax time tips helpful? If you’d like a much deeper dive into my yearlong process for making tax time easy breezy, you’ll want to access my Tax Time Training.

This is actually the first time I’m opening up access to my proprietary system. Why? Because it’s because proven to be tremendously helpful to my Bookkeeper Business Incubator students, and I want to make sure you have the resources you need to conquer tax season as well. 

To feeling prepared all year long,


P.S. Don’t forget to get your copy of my Tax Time Training! This is the PERFECT time to start building out new yearlong processes for tax season.