What Your Accountant Wishes You Knew Before You Walked In

We asked a few accountants to tell us what they wish you would learn before you walk into the office next time. Here are some of the surprising answers!

We treat our accountants like miracle workers. We walk in with a big pile of papers with a panicked look on our faces. They sigh, collect the pile, and sometime later everything is magically fixed and your money isn’t in jeopardy anymore.

If only you would take the time to learn a few things before you walked in, the whole process would actually be much smoother. Not only that, but you could participate in the growth and health of your finances and make your business that much stronger.

We asked a few accountants to tell us what they wish you would learn before you walk into the office next time. Here are some of the surprising answers!

There are No Dumb Questions

Your accountant understands that there are concepts you don’t “get.” If you did, you might not have an accountant. There will always be some new law, or rule, or other regulation that comes up and throws you for a loop. It’s going to happen.

The worst thing you can do in this situation is to simply nod your head and pretend you understand. If you don’t get it, don’t be embarrassed. There are no dumb questions!

“Give me a call if you have a question,” says Chris Peden of The Accounting Scribe, “no matter how insignificant the matter may seem. I would rather have them ask me what they think is a stupid question, than not ask and have something that should have been reported go unreported.”

George Sleeman of Tax Man to You advises, “Not all spending is deductible.” This might seem like a simple concept, but you might not realize it until you ask. “Also, you cannot expense everyday clothing because you wear a suit to work.” How would you have known that if you didn’t ask?


“Spending the time to review your business operations on an annual basis can be a time to create opportunities for tax savings or keep your compliance in check,” says Lauren Stinson from Windward Tax. “We are here to help you.”

Basically, if you’re not active in your finances, you’re limiting what your money can do. Your accountant can only do so much – they’re going to organize your money in a way they know best. If you have other ideas, though, on how you want your business to move forward, you have to be there to advise.

“I cannot get your return done without all the information I ask for,” Sleeman continues. Without your help, your accountant is only getting half the story. Help them out by participating in the discussion and staying informed.

Set Realistic Expectations

You probably know by now not to rush into your accountant’s office on April 14th with a giant stack of papers for them to help you with. However, you’re probably recreating this same stressful situation throughout the year and not even knowing it.

“I cannot get your return done in an hour,” Sleeman bluntly states. No matter the form or paperwork you want them to help you with, expecting them to literally pull off a miracle is unfair and unprofessional on your end.

On top of that, the more you rush your account the more likely there will be an error. Just make sure you get all your ducks in a row quickly so you have time to calmly explain what you need as well as ask questions when you’re confused.

Accountants are our friends. They keep our feet out of the fire and the taxman from our door. We hope these tidbits from real accountants will help your relationship with your own financial pro run more smoothly!

Zach Olson is the Founder & CEO of TaxAlli.com. At Tax Alli, we pair you with real life accountants and use cloud software to make small business accounting awesome. So you can do what you love while we handle the rest.

Self Employed Tax Deductions: How to Turn Procrastination into Motivation!

When you woke up this morning, your first thought (after thinking “Nice. The world didn’t end.”) was probably something like “Dang. The world didn’t end. Now I have to deal with my self employed tax deductions.”

Whether it’s deductions, taxes in general, or scrambling to gather slips of paper and receipts that have been collecting dust for 12 months, the end of the year can be a seriously stressful time for small business owners, freelancers and the self-employed.

With a mere 10 days left in the calendar year, and a quarterly tax due date just around the corner (that’d be January 15, 2013, in case you’re interested), even the most diehard procrastinators are beginning to admit that the time has come. Though shalt do thy taxes.

If a post-apocalyptic countdown isn’t enough to get you geared up, check out our completely non-businessy list of ways to motivate yourself to move those self employed tax deductions from the to-do list to the DONE list!


Finishing your taxes can be a massive task, especially if you’re a solopreneur running a one-woman or one-man show when it comes to your business. If no one is going to do your taxes but you, and you’ve waited until now to start getting organized, you may be facing a project as big as those stones the Mayans used to predict our December 21st expiration date.

In order to get motivated to dive in to your taxes, bribe yourself with a treat that is more enticing than the dread surrounding your deductions. This is not the time to splurge on a chocolate bar or a new iTunes download. We’re talking about some serious carrot dangling here. Spoil yourself with something along the lines of:

  • A massage. A 90-minute massage.
  • A long weekend at the most exotic location you can reach by car in 5 hours or less.
  • An entire day (24 full hours!) with the phone and computer turned off, the guilty pleasure marathon of your choice on TV, and a tube of cookie dough for dinner.


After reading the Shoeboxed blog all year, you’re obviously armed with a crazy amount knowledge as to what qualifies as self employed tax deductions. After all that learning, it’s time to cash in! Grab your virtual assistant, your significant other or your best friend, and place bets as to the grand total of qualified write-offs you have for 2012. You can even get fancy and bet on specific categories: travel, office supplies, health insurance premium payments, the sky’s the limit!

The winner of the bet gets the prize of their choice from the “Bribe yourself” section above!


If you use FreshBooks for your accounting, a lot of your procrastination pain will be relieved come tax time. Besides providing you with year-end invoicing totals and helping you calculate expenses, FreshBooks creates nifty graphs and charts that let you see how much you’ve earned and spent throughout the year.

These charts are seriously motivating! Set goals and see if you can beat your own best record. The faster you get your taxes done, the faster you’ll be able to hang up your graph on the fridge!

FreshBooks Chart


You, your other self employed buddies, and a pitcher or two of margaritas. Oh, and you’re doing your taxes. What could be more fun than that? Host an end-of-the-year tax party with all the fixings. You’ll be able to swap war stories, share tips and tricks, help each other with accounting, and answer each others’ questions about whether or not that trip to Cabo counts as a write-off.

How do you get motivated to do your taxes?

photo credits: valleydalemassage.com, freshbooks.com

The Shoeboxed Weekly Recap: Building Wealth with Business Tax Deductions, Timeless Human Etiquette for a Digital World and More

This week was a busy one at Shoeboxed HQ! As we cruise through November the Shoeboxed team is gearing up to make this holiday season the most organized one yet.  In case you didn’t have a chance to check in with us this week, here is a quick recap of what you missed on the Shoeboxed blog:

1. Are you maximizing your business tax deductions? We want to make sure you are. So on Monday we explored how to build wealth with your business tax deductions.

2. On Tuesday we unveiled a brand new feature to help you keep your Shoeboxed account clean and organized! If you haven’t already, login now and try Receipts Needing Attention.

3. It’s a Brave New (Digital) World we live in. On Wednesday we took a step away from the computer to explore Timeless Human Etiquette for a Digital World.

4. The IRS doesn’t have a reputation for being concise in their documentation, nor for making things particularly straightforward for the taxpayer. For this reason we spent some time decoding IRS jargon on business tax deductions.

5. In this week’s edition of Organized Fridays we answered a question that CPAs and bookkeepers ask us often: “How can I help my clients get organized?”

Stay organized this weekend,