The Independent Contractor’s Back-to-School Checklist

All the must-do items leading up to fall for any freelancer or gig worker, whether or not you’re a student

Just when you get into the swing of summer, it starts to wind down, and the hustle of the rest of the year looms large. August and September mean back-to-school for many folks. Maybe you’ve got kids returning to the classroom—or you’re on your way there yourself for college or continuing education. Or maybe none of those apply but you’re back to the grind after a much-needed vacation. The next several months might be your busiest of the year with the holiday bustle to follow. Our back-to-school checklist is meant for any indie contractor or gig worker, regardless of whether class schedules are actually involved.

Supply and gear assessment

Back-to-school time sounds the signal to buy supplies. Anyone heading to school obviously has to load up on the requisite notebooks and highlighters. But freelancers and gig workers need gear too. Have you been in the market for a new laptop or tablet? Do you need to upgrade your software? How’s that car you use for rideshare? Does it need new floor mats? What about the kit you use for in-home healthcare? Could it be restocked? Does your home office beg a new desk chair with better back support? You get the idea. Take an inventory of your work tools and see what might help you do your job even better. The great thing about buying during back-to-school time is that a lot of stuff is on sale.

Healthcare assessment

Kids going back to school often need physicals for their sports activities and certain immunizations. Now’s the time check in with yourself, as well. Unfortunately, independent contractors don’t get paid sick leave, so it’s always in your best interest to take preventive measures. Have you been suffering from eye strain? Maybe an exam is in order for updating your glasses prescription. Have you had your annual checkup? Fall is a great time to schedule one so that you can also get your flu shot.

Be sure to renew any medication prescriptions so you don’t have to worry about it when you’re slammed with work. The fall allergy season will ramp up soon, so stock up on any items that will help you snuff out the sniffles or relieve itchy, watery eyes. Check your medicine cabinet and refill any essentials that are lacking, like over-the-counter pain relievers, cough medicine, antacids, etc. The worst time to have to go to the store for meds is when you really need them.

Schedule assessment

Your schedule might change with the season. If you had the kids at home during the summer but now they’re heading back to school, that might free up daytime hours for work. Likewise, if you were working during the summer as an independent contractor but now you’re heading back to college, you might have to fit work around your class schedule. If school isn’t on the horizon for either you or your family members, then fall can still be a great time to check in with your schedule. Figure out your fall work hours. Plan ahead for any time you plan to take off, like for holidays or when the kids are on break. Look for periods in your schedule when you can also work extra to earn more income. Is there anything about your summer schedule that drove you bonkers? Changes things up for the months ahead.

Personal assessment

One fun part of back-to-school shopping is buying a few pieces for your wardrobe or getting a new haircut. Perhaps you need to upgrade your cool-weather coat. Or maybe you want a new item of clothing to wear for face-to-face client meetings. More supportive shoes might be in order if you’re on your feet all day. Take stock of anything you wear for work that needs to be replaced, like the requisite black pants and white shirts often donned in the restaurant industry. Then schedule that haircut or whatever else you might need, whether for fun or for a special fall event.