Question: What is one thing I should do this year to make dealing with my taxes less of a hassle?
Keep Great Records
"Make sure to keep records of anything that could have a tax impact. It takes a few extra minutes each day to save emailed documents or scanned paper documents, but having that information readily available for your bookkeeper and tax accountant will save a lot of time and money come tax time."
Separate Your Business and Personal Finances
"To simplify tax season, separate your personal finances from your business finances. So many startups mix up the two and find themselves in a mess. You must have separate accounts, keep costs separate and maintain separate income statements and balance sheets. When you blur the lines, you create major hassles, which can lead to serious expenses, legal issues and additional taxes."
Hire a Dedicated Bookkeeper
"Whether outsourced or in-house, make sure someone is 100 percent on top of the books at all times. I make sure to maintain our company books on a daily basis, and when tax time comes around, I spend no more than 15 to 20 minutes getting everything ready to send to the accountant."
"Shoeboxed is a tool I can't live without in my business. All my receipts get mailed or emailed to it, and it scans and sorts them for me. I can see all my receipts organized within its interface, and then my accountant can export the expenses to QuickBooks. It's an affordable service that has saved us so much time and money."
"File your receipts as they arrive according to the particular deduction they pertain to in an organized filing system or via a document storage service for electronic invoices."
Keep Receipts on the Cloud
"Staying organized all year might sound cliché, but it's a mantra because it's true. Be sure to keep receipts organized. In particular, create a set of file storage on the cloud, so you can keep your accountant updated throughout the year. Set a date each month to take care of this type of work so that staying organized and keeping your paperwork accessible won't be a cumbersome process."
Ask Your Tax Professional for a Planning Session
"If you can sit down with your accountant or tax preparer (perhaps after this year's tax season ends), you can discuss how to improve your tax situation in the coming year. You can also discuss what strategies they would recommend for making tax preparations easier next spring."
Make It a Game
"From Easter egg hunts to Halloween as kids, we are triggered to discover and collect things. I make a game of collecting all of my bank statements and paperwork for tax season. When I collect all of the "pieces" and the basket is "full," I reward myself with something fun like a nice bottle of wine or a massage. Nothing helps me stay more organized or more aggressive in collecting my paperwork."