Keeping Your Job, But Transitioning Into Remote Employment

by Meryl Williams

Earlier this year, I was lucky enough to convince my Chicago company to keep me on remotely so I could move to Portland. This was great news for many reasons: I love my job, but I didn’t want to live in Chicago anymore. I also didn’t want to try to find a new job, and risk getting one I didn’t like as much — or worse, risk draining my savings on being unemployed.

My excellent boss went to bat for me, and our company agreed to let me stay on as a remote employee. While it was a strange transition, it’s been great overall. My boss is also a remote worker, so our dynamic hasn’t changed despite my move — we use tools like OoVoo video chat and GoToMeeting to keep in contact throughout the day. Plus, now we’re at least in the same time zone.

Recently I sat down to assess which has been more financially beneficial: Working at our Chicago office, or working from home (mostly) in Portland.


In Chicago, I lived 21 miles from my suburban office, meaning I had a 42-mile commute every day. I filled up the tank of my Cavalier once a week, and additionally spent around $20 each month on Illinois state highway tolls to get to the suburbs. I also used to get, ahem, a few parking tickets.

Now that I’m in Portland, I barely use my car. I’m saving an estimated $90-$120 per month on gas, plus that $20 each month on tolls. I’m also saving time — I’m not in my car for 2–3 hours each day like I was, which has been a huge sanity-saver. The only downside is that I have less time to listen to podcasts and maybe I’m a little rusty on my Top 40 music knowledge these days. I’ll take it.

Office Costs

Now that I’m a remote worker, my company pays for my internet. This saves me about $60 each month. However, I am spending money on a coworking space in Portland, which costs $250 monthly. This is actually a competitive rate for a great service — it’s just not one I’ve ever felt comfortable asking my employer to cover, since their expectation is for me to operate out of my home. I consider myself lucky that no one minds that I go to this space a couple times each week.

The coworking space is a worthwhile expense to me at this time — being around other remote workers gives me a sense of community and normalcy I sometimes miss when I’m working by myself in my apartment. It was also an amazing way to meet new people when I first moved to Portland. Our space offers plenty of after-hours activities and networking events, plus it gives me a group to eat lunch with.


When I was in Chicago, I was pretty good about packing my lunch. Going out for food near my office meant a minimum additional 20 minutes spent in my car, the inside of which I was pretty tired of seeing, thanks to my commute. I packed salads from home and made the occasional Trader Joe’s snack run, but my food budget was pretty well under control.

Now that I’m in Portland, I’ve developed some rough habits around eating. When I work from home, I sometimes forget to eat. That usually results in an early evening poor choice, like ordering Thai from GrubHub or grabbing nachos from the place down the block. On the days I go to the coworking space, I almost always grab a bagel on my way down. At lunch, we often frequent one of Portland’s amazing (but sometimes pricey) food cart pods. I like having people to grab lunch with, but the cost adds up in a way it didn’t when I worked in my old office.

State Taxes

I try so hard not to complain about taxes — they are why we have cool things like roads and public services! That said, I could not help but notice that an additional ~$50 of my bi weekly take-home pay vanished after I moved. Illinois’s state tax rate is 3.75 percent and Oregon’s ranges from between 5–9.9 percent. But for what it’s worth, Oregon doesn’t have sales tax, while Illinois’s rates range from 6.25–9.75 percent. That makes Oregon not such a bad place to buy a big-ticket item, like a new laptop or TV.

Overall, working from home in Portland costs me about the same as it did to work in our Chicago office. However, gaining those 2–3 hours each day I used to spend commuting has been priceless. I miss being in my old office, but luckily my company flies me back to Chicago for a week each quarter. They pay for my flight, hotel, and rental car, and I am usually able to extend my visit into the weekend to see my old Chicago friends. Other than missing out on the in-office events that take place throughout the year, it’s mostly like I never left.

Meryl Williams is a Chicago journalist who recently moved to Portland. She loves roller derby, upbeat music with depressing lyrics, and shamelessly ordering the Kids Pack-size popcorn at the movies. Sign up for her awesome TinyLetter.

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