Your Guide to Leveraging Tax Write-Offs to Traverse the Windy City
Work-Life Balance isn’t just one thing, it looks different for everyone. Even if you’re not a full-time relief veterinarian, whether you live in Illinois or anywhere else in the country, work-life balance is always within reach. That’s why we’re launching our Work Hard Play Hard series to explore creative ways contract work can help you better take advantage of your free time (you’re gonna want to know these 1099 hacks).
As a proud Chicagoan, born and raised, I’m making an executive decision: We may be the Second City, but today, we’re up first. Chicago vet med, let’s rock!
Beat I-94 traffic with 1099 tax tricks (hear me out)
They say Chicago has two seasons: winter and construction season. My wife, who I dragged up into the icy north from California, doesn’t find this joke very funny. Lately, whatever they’re doing on the 94 has made commuting in and out of the city excruciating, and very often, that’s where the Roo relief shifts are.
But what if that commute was worth your while?
If you live out in the burbs, how often do you get into the city? Probably not as often as you’d like, and all the fun stuff is in the city. All the GREAT food, some of the top museums in the world, all the sports teams we love to watch lose — it’s all downtown! But if you’re like me, you simply never get downtown because you’re busy, because it’s far, and because it’s a pain to get to.
A single Chicago relief vet shift gives you an excuse to take that leap, AND you’ll get paid in more ways than one. A single shift downtown can pay out over $1000, and remember, you sat in traffic for work. There’s some tax write-offs coming your way.
1099 hacks for the veterinary commuter
That single shift in the city probably just put you over the $600 mark, allowing you to deduct business expenses as an independent contractor for the entire year. In fact, if you commuted at all to work your shift, there will be money waiting for you in April. Whether you’re working as a relief veterinarian in Illinois heading to or from Chicago or you’re commuting to any other metro area in the country, these tax tips are for you:
- All the mileage from your drive in and out of the city is now a tax write-off. Even if you decide to make an evening of it and spend the night downtown, you still had to get here for work and you still have to get home.
- Alternatively, you can write off your gas for the trip, but that gets a lot harder to calculate and the rates tend to not be as favorable.
- Any tolls you pass through on the way can be written off too! And we all know, in Illinois, there are plenty of those.
- Do you know how expensive parking is in Chicago?! It’s criminal, but guess what? You came here for work. Boom — tax write-off.
This one’s for every traveling relief veterinarian out there, whether you’re in Illinois or coming from out of state — if you commute more than 50 miles to get to your shift, the perks get even better:
- Lodging, such as an overnight hotel stay or an AirBnB rental, is a tax write-off too if you’re over 50 miles from home, and it doesn’t matter whether your hotel stay is before or after your shift. Stay downtown after your shift and make an evening of it, or book a hotel room the night before, spend a day downtown, and work your shift the next day — either way, that’s a write-off.
- Breakfast, lunch, and dinner — in fact, any meal (within reason) you have once you’ve commuted over 50 miles from home is a business expense you can write off. Coffee and snacks too. Coffee is very much a business expense.
For all of the above, just make sure it’s reasonable and well-documented. The Drake Hotel or Alinea might raise Uncle Sam’s eyebrows, but there are a plethora of great eats downtown.
Bring a few coworkers you just met during your shift, and guess what? Now, you’re networking, and your meal’s a write-off no matter how far you traveled. I highly recommend Hopleaf on Clark, which is literally just a few blocks down the street from Uptown Animal Hospital where you can pick up Roo shifts.
Or, if Belgian ales aren’t your thing, Hop Butcher for the World has the best hazy IPAs in the city, and that’s just a fifteen minute walk from Boulevard Veterinary Ravenswood, another Chicago hospital partner.
Join Roo today to see all the amazing Chicago hospitals we have to offer. With just a bit of strategic planning, there’s so much to take advantage of to make your trip into the city worthwhile.
1099 hacks for the city dwelling relief vet
Are you a Chicago vet or tech living downtown and just need to get around the city? Transportation to and from your shift is still very much a tax write-off.
- Any sort of public transportation you take to get to your shift, whether by Metro train, ‘L’ train, bus, taxi, Lyft, or Uber — all a write-off, and you get to pick.
- Want to ride to work in style? Hop on a public Divvy Bike, and as long as you’re on your way to or from your shift, that’s a tax write-off and your exercise for the day. Take the scenic route, bike along the lake. Chicago is one of the most bike-friendly cities in the world, and if the weather’s nice, this mode of transportation can’t be beat. You’ll have to hurry though, because that’s a big “if” this time of year.
- You can even write-off a rental scooter if that’s how you’re getting to your relief shift today.
All upside with epic FREE Chicago entertainment
I know what you’re thinking: If I spend all this money downtown, I’m going to end up losing money. Think again – Chicago is absolutely filled with free activities.
First off, the Lincoln Park Zoo is one of only nine free zoos in the country, and it’s absolutely fantastic. We know you love animals, so this is really a can’t-miss. Enjoy the zoo itself or, in my opinion, the even more beautiful nature boardwalk nearby (pictured above), a nature preserve in the heart of Chicago. Pets First Veterinary Clinic is just a mile away from the boardwalk; that’s definitely walkable.
As I teased earlier, Chicago has several of the best museums in the world and guess what? Almost every single one of them offers Free Museum Days, which are usually on weekdays so they nicely coincide with most shifts. Plan your shift on one of these days and swing through the museum of your choice. Partner’s Animal Hospital South Loop is just steps away from Grant Park, the Art Institute, and the museum campus, where you can pick up a shift for the day and visit your museum of choice.
It doesn’t matter if you only get an hour or two in because it was free! Meet Sue at the Field Museum, the largest and most complete T-Rex skeleton ever discovered on October 10, 17, 24, or 31st for free! Worried about your shift running too late? The Adler Planetarium is free every Wednesday for Illinois residents until 10:00 PM — relief veterinarian by day, by night, blast off to outer space!
The Art Institute of Chicago, perhaps one of the best art museums in the world, is free for Illinois residents every Thursday evening from 5:00 – 8:00pm, perfect post-shift timing. You’ll have to reserve tickets in advance, but you’ll also have to request your shift in advance so a bit of strategic planning goes a long way here.
Here’s my favorite Chicago pro-tip of all time: There’s no need to pay to go to the top of the John Hancock. There’s a cocktail lounge on the 95th floor – a floor higher than the observation deck – with full 360 degree views of the city that’s free to go to! They just require you buy an overpriced drink. They’re open until 11:00pm and just a short walk from Companion Animal Hospital River North, another Roo hospital you can grab shifts at! Bring a new friend you made that day during your shift and write-off that cocktail.
Who could forget all of Chicago’s excellent outdoor activities, which are spectacular about 60% of the year and terrible frigid torture about 20% of the time. There’s miles upon miles of lakefront beaches, riverwalk, outdoor parks, and so much more to explore downtown even for just an hour or less before or after your shift.
Turn your shift into something more
A simple Roo relief shift doesn’t have to be just another day at the clinic. Take advantage of this unique opportunity to turn it into something more. These tips aren’t just for vets in Chicago or even Illinois, any relief veterinarian or technician can take advantage of these 1099 hacks to save money on transportation, meals, and possibly even lodging wherever Roo has relief shifts.
For even more great tips on perfecting the art of work-life balance, check out the Roo work-life balance guide.
No matter where your Roo shift takes you, there’s so much more to explore. Take a beat, slow down, make a day of it. Enjoy a new experience.
Sources & disclaimer
These great tax tips are brought to you through our partnership with Fit Money CPA, who have been tremendously helpful supporting our Roo relief veterinarians and technicians to manage their taxes as independent contractors.
Roo is unable to provide tax advice as each situation is unique. The tax tips provided here are for informational purposes only, and we highly recommend consulting a certified tax professional before filing your 2023 taxes for the most up-to-date information that applies specifically to you.