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Tips & Tricks For Making Tax Season Less Painful

It’s that time of year that we all, especially us freelancers dread- tax season! Over the past few years, tax prep has become completely overwhelming to the point that it feels as if I take on an entirely new job. Most staff or salaried employees only receive one w2, but as a freelancer, everyone of my clients sends me a separate 1099 form. This mountain of paperwork, coupled with the need to save every receipt and document every single expenditure, as well as documenting each and every expenditure is mind boggling. And to add to the workload, Jason too is self employed. That’s double the receipts, double the 1099s, and double the bookkeeping!

Tips & Tricks For Making Tax Season Less Painful | Stroller In The CityKeeping our paperwork organized and running efficiently is critical to daily operations. Recently, while printing docs to send to the accountant, we realized that it was time for new printer. Our old machine liked to freeze up, or print partial pages due to clogged up inkjets, so we needed to make a change fast. After researching a few printers, we discovered the Canon MegaTank All-in-One Printer. As you know, I am a lover of all things Canon, so I was sold as soon as I learned some of its capabilities. Since Jason and I both work from home at times, we may need to print from multiple computers or devices. With that, Wireless printing is a must.

Tips & Tricks For Making Tax Season Less Painful | Stroller In The CityI am not a very tech savvy person by any means. When it came time to set up our printer, I am happy to report, I did it all by myself. This included filling up the refillable ink tanks. Since the MegaTank has integrated refillable ink tanks, you can print up to 30 times more ink compared to standard cartridge sets, allowing you to print larger quantities of documents for longer periods of time. With a Continuous Ink Supply System, the ink tanks are outfitted with multiple airtight tubes, delivering a continuous flow of ink that makes printing larger quantities more efficient and productive. Considering the way our last printer clogged up and printed partial pages, I was excited by this ink system.

Tips & Tricks For Making Tax Season Less Painful | Stroller In The CityThis Canon MegaTank can print up to 6,000 black text pages and 7,000 color pages, so what does this mean? It takes a lot for this bad boy to run out of ink. With printing everything from tax documents, to kids’ homework, to photos, there is no need to run to a copy shop to get it all done. Plus, with two full-size BONUS black ink bottles that come with the machine, you can print up to 18,000 black and white pages!

Tips & Tricks For Making Tax Season Less Painful | Stroller In The City

I even downloaded the Canon Print App, from the App Store, so I could print directly from my smartphone! This feature is key for me, since I usually multitask, working off my phone and computer throughout the day.

Another feature that wasn’t available on my previous printer was the auto document feeder, allowing me to scan, copy, or fax multi-page documents. This is major! After a package to our accountant went missing last year, I will never send anything off without having another copy on hand. Fortunately, that package surfaced. But if the documents got lost in the mail, starting from scratch would have been a disaster.

Tips & Tricks For Making Tax Season Less Painful | Stroller In The City

Through the years, we have found little tricks to make tax season less stressful. We review finances on a monthly basis. We also balance all bank and credit card statements as soon as they are generated. It’s tough to find this time each month. But I promised its much easier than trying to enter or reconcile 12 months of statements. 

Tips & Tricks For Making Tax Season Less Painful | Stroller In The City

Previously, I thought having my credit card statements were enough. An audit a few years ago taught me otherwise. I will tell you this: save all of your receipts, and keep a log of your business activities. This will help you determine what that meal in November was for, and why you took a $30 cab in June. 

Tips & Tricks For Making Tax Season Less Painful | Stroller In The City

Find an accountant who understands your business. I’ve been through several accountants over the years, and learned how important this can be. Some tax professionals specialize in certain field, and have a greater knowledge of your specific needs and business practices. 

Tips & Tricks For Making Tax Season Less Painful | Stroller In The City

And my final tip, get the Canon MegaTank All-in-One Printer. By allowing me to print so many tax documents at once, minus the paper jams and ink issues, it has saved us this tax season. And I’ve started printing out my favorite photos from our Paris trip. I cannot get over the quality of my new printer!

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Tips & Tricks For Making Tax Season Less Painful | Stroller In The City

photography: Lauren Kara 

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14 thoughts on “Tips & Tricks For Making Tax Season Less Painful”

  1. I love this! Anything I can do to make tax season easier and less like pure torture is always welcome. Doing taxes is the 9th circle of Hell.

  2. Canon products are wonderful and this seems like an asset for the home office. I’ve used the same tax preparer for 18 years, as she is very informed of how to handle taxes for the self employed. I dread this time of year and gathering up all the necessary documents.

  3. You have the right idea– get organized to make preparing taxes go much more smoothly. We have a special place we keep all financial statements, paystubs and past tax statements. It makes it a snap when it’s actually time to sit down and plug in the numbers when we’re ready to file. No looking, no searching, no headaches.

  4. Wow I love that you can print from your phone! It makes it so much easier than emailing a document to yourself, getting on your computer, downloading it, etc.

  5. Sounds like an awesome printer! I Just bought an Epson about a week ago; what a bummer as this one sounds awesome!

  6. Catherine Santiago Jose

    Wow, that was an awesome printer and I am glad that it has a feature that you can print from your phone. Canon really have a great products and I love them!

  7. For me, an accountant is definitely the way forward. I find it a headache and just prefer to set aside money to pay them this time each year!

  8. I know it’s a little late for this year–or even a lot late for freelances/payers who hire subcontractors. But for any entrepreneurs out there looking for cheap 1099 software for January tax prep, I recommend this software provider: https://www.1099-etc.com/

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