A Financial Tool For Self-Employed Wearers Of Many Hats

Fellow freelancers and self-employed women, take note, and take charge.
Photography: Leah Pellegrini

Photography: Leah Pellegrini

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“What do you do?”

Like many in the self-employed space, I wear many hats. Sometimes, I mean this literally: as a traveling organic farmer, my mornings often find me out in a field somewhere, a baseball cap shading my face from the sun while I tug carrots from the soil or weed around tomato plants. Other times, the hats are a lot less literal: by evening, I may be sitting inside at my computer, writing or editing articles, emails, or communications and copywriting plans for clients. On different days, I’m completely captured behind the lens of my camera, photographing portraits or events. And when I’m not wearing one of these various freelancer hats, I’m honing my own artistic practice, either working on my photo- and illustration-oriented product line or writing bits of creative nonfiction.


So, what do I do? There are connective threads that knit all of these different pieces of my multi-hyphenate career together — in short, I’m interested in honest, heartfelt storytelling about the below-the-surface complexities integral to both earthly nature and human nature — but still, I wear more hats stacked on my head than even I can count sometimes. I’m like that salesman in Caps for Sale, which was one of my favorite picture books as a kid. Perhaps this was some sort of foreshadowing. And perhaps the plot line should have been a warning. When the main character, the cap peddler, settles for a nap one day, a bunch of monkeys manage to steal all of his hats from his head and scatter off to separate tree branches, taunting and imitating him as he demands they give the wares back. Eventually, the man throws his one remaining cap down on the ground in a moment of exasperation, and the monkeys thankfully follow his lead, tossing the squandered hats down at his feet and thus enabling him to return to work.

In other words, those of us walking with many hats stacked on our heads have to stay diligent and conscientious. If we’re not paying attention, we’ll lose some of our most valuable resources. And if we don’t maintain a sense of balance and track our steps carefully while we’re in motion, our caps can begin to teeter and topple.


Lately, my favorite resource to keep me on course is QuickBooks Self-Employed, designed specifically for those who wear tall towers of hats, too. The different tools included within the app make it fast and easy to keep tabs on the nitty-gritty details of my day-to-day operations and on the different aspects of my personal business. 

Perhaps most usefully, I’ve been using QuickBooks Self-Employed to track expenses that might otherwise slip through the cracks. The app automatically connects to my bank account and my credit card for business purchases, so I can record everything from coffee meetings with clients to payments for website hosting, and then submit it all for tax deductions. (There’s also a function for snapping photos of paper receipts, so cash purchases can be imported, too.)

Since my work takes me traveling across the United States and beyond, I should be monitoring the miles I drive from job to job to deduct as well — but this has always seemed too complicated, so I’ve neglected to make the effort in the past. Now that I’m signed up with QuickBooks, I can stop pleading naive and forfeiting those potential deduction dollars. The app can automatically record a car’s odometer readings, or they can be plugged in manually.

After all of this record-keeping made simple, there’s still one final step, and it’s the one most self-employed people truly dread, because it can’t be dodged or left half-done: actually completing and submitting taxes. The addition of the TurboTax Self-Employed program (combined with the QuickBooks tools) offers individualized, one-on-one support, with the option to speak directly with a credentialed tax expert who’s fully versed in the specifics of self-employment taxes. With just one week left until the filing deadline and a few lingering questions about my personal expenses and deductions, it seems wisest (and, honestly, just easiest) to turn to a professional right now — someone who can ensure that I’m truly squared away. Particularly since I work remotely and am eternally in transit, I appreciate the access to true human help via my laptop (all tackled via screen-sharing, so this pro can circle and highlight any final steps I might need to take, and at no additional cost).

All of this record-keeping and extra guidance adds up. According to the company, QuickBooks Self-Employed users typically find an average of $4,340 in potential tax savings per year and more than $18,000 in deductions. These numbers matter. These are the resources we need, as self-employed people, to continue to do our best jobs. They are the numbers that enable us to turn our quirky passions into sustainable careers. 


Those of us who consider ourselves “creatives” can resist the concept of regimented systems and logistics — the practical things that seem to box us in or simply bore us, when we’d rather be daydreaming. But without some sense of logic and structure, nothing works. We have to act as our own managers and HR departments; we have to track our progress; we have to keep ourselves on course and avoid squandering or overturning our hats unconsciously. Sometimes, we have to slip up and find ourselves frustrated — like the cap salesman, chucking his one last hat at the ground — before we finally choose to get smart and serious, and before we realize that the option for guidance we’ve needed has been there all along. 

That’s where I’m at now: learning to take more control over my tax deductions so I can actually get the full benefits of working for myself. I’m empowering myself with modern tools and technologies, instead of dodging money management like some sort of scary and unwanted responsibility. I’m keeping my finances organized and better distinguishing my business from my personal life, however intertwined the two might sometimes feel. And I’m re-stacking my many hats with more structure and balance. 




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