I’m a Supercommuter. Here’s What It’s Really Like.

Sometimes I sleep in a different New York City hotel room every night.

On a recent Monday, it was a Midtown Manhattan Hampton Inn. The next night, a budget hotel downtown. Then I moved to a Hyatt in Queens, near John F. Kennedy International Airport, where I waited to check in behind a group of pilots and flight attendants.

The reason for this madness: My job is in New York, but my apartment is in Columbus, Ohio. When hotel prices are high, I property-surf to find a lower rate.

For more than a year, to the bafflement of family, friends and colleagues, I have attempted to live and work as a supercommuter. What began as a postpandemic experiment of flying to and from New York each week has turned into what I am hesitant to call a lifestyle.

Like many, I moved out of the city early in the pandemic, relocating near family in the Midwest. When it came time to return in 2022, I was underwhelmed at the housing options in my price range. I toured one-room studios facing brick walls and climbed crumbling staircases to reach dank apartments with ancient fixtures. I also had grown accustomed to midweek evening walks with my sister in Ohio, and a short drive to see my parents. I didn’t want to fully give that up.

Using back-of-the-envelope math, I thought I could keep my expenses—rent in Ohio, plus travel costs—at or below the price of a nice New York studio, or roughly $3,200 a month. The Wall Street Journal requires office attendance at least three days a week and, since I commute by choice, I pay all my travel expenses.

Luxury suites and room service

The challenge felt oddly thrilling. If anybody could find a way to subvert high New York real-estate costs, while remaining close to family, I thought it might be me. For years, I’ve been an on-call travel guru to friends and co-workers, coaching people on how to navigate flight cancellations and play the credit-card bonus games. I memorise aircraft configurations and spend hours reading mileage blogs and industry sites like Airliners.net.

Before mileage runs became useless, I obsessed over reaching top-tier airline status by spending as little as possible. (Family members still roll their eyes at the six hours I spent in Anchorage one December afternoon to requalify for Delta’s Diamond tier.) When a flight is oversold, I am quick to volunteer my seat in exchange for a voucher. (My best-ever haul: $2,000 after giving up my seat on multiple oversold flights one Saturday in San Francisco.)

Nerding out about this stuff has allowed me to travel farther and in more rarefied air than I could otherwise afford.

Entering my supercommuter era, I had visions of flying to New York on a weekday morning (8,500 points one way on American Airlines), spending the day meeting sources and filing stories, and retiring to one of my favourite points hotels—the Beekman. Mornings would begin with a free breakfast thanks to my Hyatt status, before a short subway ride to the office. After two nights, I’d return to Columbus and my roomy apartment, half the price of a Manhattan studio.

Shocking no one, that fantasy soon came crashing down.

Burning points on fancy hotel rooms was the first problem. The life of a journalist is hard to predict. I repeatedly found myself on deadline and having to rebook flights or stay an extra night, costing me money or miles.

Once I was back in the city, it also got harder to say no. Stay an extra night to attend a friend’s birthday party or meet a CEO in town just for the day? Sign me up. I didn’t want my living situation to strain relationships or interfere with my job, which I love.

To conserve hotel points, I swapped the Beekman’s elegant rooms in lower Manhattan for a Hyatt attached to a casino in Jamaica, Queens. My rooms overlooked a sea of empty parking spaces, but required half as many points as Manhattan alternatives.

Flight delays and blown budgets

By summer, with my miles dwindling and New York hotel rates rising, I reluctantly began to rely on the kindness of those around me. Hearing I might need a place, one friend mailed me the keys to her family’s unoccupied apartment in New Jersey. Another let me stay in her smartly designed Brooklyn one-bedroom for weeks as she traveled. A cherished deskmate, known for her tell-it-like-it-is demeanour, repeatedly offered a bedroom in her Chelsea loft, handing over the keys with a sometimes expletive-tinged reminder to: “Get a f—ing apartment.”

I watered plants, walked friends’ dogs and fed their cats while they were away. Still, working in a city without a permanent home took a toll. I came to dread the go-to question asked at parties and work events in New York: “So where do you live?”

After house sitting for friends, I fell in love with some of their pets, including my friend Vanessa’s Border Collie mix, Ivy. But when in hotels without a refrigerator or stove, uninspiring meals abounded; a late-night dinner of yogurt and fruit.
CHIP CUTTER/THE WALL STREET JOURNAL

If I admitted, “it’s kind of complicated,” I got sucked into explaining my life as a supercommuter. Sometimes, I’d just tell people the location of that evening’s hotel. (Chelsea!)

Costs mounted in the fall, New York’s prime tourist and business-travel season. Friends teased me for embracing a life of chaos. They weren’t wrong. Without a refrigerator or stove, late-night dinners often consisted of yogurt and fruit purchased from a 24-hour CVS. Needing to pack light, I stored shoes under my desk and left spare outfits on an office coat rack.

To get to the office on time, I set my alarm in Columbus for 4:15 a.m. and hustled to the airport for 6 a.m. flights. When everything went according to plan, I made it door-to-door in three hours. If delays occurred, I scrambled to rebook on other flights.

My obsessive tracking of New York hotel prices taught me that dynamic pricing isn’t reserved for airlines. Hotel costs can fluctuate half a dozen times on the check-in date, so instead of booking in advance, I’d wait to pull the trigger until 10 p.m. some days after the rates fell.

In the end, the math didn’t work. I blew my budget by 15% and drained my miles balance. But I flew so much and stayed in so many hotels that I kept my elite status with Hyatt and American.

I still enjoy having one foot in the Midwest and one on the East Coast, though I’m not sure how long I can keep it up. I’m writing this from Columbus, where I overlook a beautiful park outside my picture window. My lease is up, but hotel rates in Manhattan this winter have plunged now that the holidays are over. Maybe that New York apartment search can be put off a little longer.

Every year, thousands of Australians make the decision to pack up life overseas and come home.

After years, sometimes decades, building careers, accumulating assets, and growing families in places like Dubai, London, Singapore, or Hong Kong, the pull back is understandable.

What most don’t appreciate until it’s too late is that the return journey is often far more financially complex than the departure.

Leaving Australia is, financially speaking, a relatively clean event.

You depart, you potentially become a non-resident for tax purposes, and a new set of rules applies.

Coming back, however, means reconciling everything you’ve accumulated offshore with an Australian tax system that hasn’t been standing still waiting for you.

The Tax Residency Trap

The first and most costly mistake is misunderstanding when Australian tax residency resumes.

Many returning expats assume residency only kicks in once they’ve formally re-established themselves, signed a lease, updated their address, started a job. The ATO doesn’t see it that way.

Under Australian tax law, residency can recommence the moment you land with the intention of remaining. That means any taxable events, investment income, asset disposals, foreign account distributions that occur after that point are potentially assessable in Australia, even if they’re sitting in offshore accounts you haven’t touched.

Superannuation: The Clock Doesn’t Stop

One of the most underappreciated issues for returning expats is what’s been happening inside their superannuation fund while they’ve been away.

Contributions may have paused, but fees, insurance premiums, and investment volatility haven’t. Some returning clients are genuinely shocked by how much ground their super has lost to fees during periods of lower balances or inappropriate investment settings.

The more strategic issue is what to do on the way back. If you hold foreign pension arrangements, a UK SIPP or QROPS, a 401(k), and international savings schemes, the question of whether and how to repatriate those funds requires careful planning before you return.

Once you’re a tax resident again, distributions from certain foreign structures can be assessable as ordinary income, and the window to manage that exposure closes.

Offshore Investments Don’t Disappear

Returning to Australia doesn’t sever your obligations in the countries where you’ve been living.

Foreign-held shares, managed funds, or investment accounts will be picked up by Australian tax reporting requirements from the moment residency resumes.

The Foreign Investment Fund rules, transferor trust provisions, and the reporting obligations under Australia’s tax information exchange agreements mean these holdings need to be declared and, in some cases, restructured.

Leaving investments sitting offshore in structures that made sense as a non-resident but create compliance headaches as a resident is one of the most common and expensive mistakes we see.

The restructuring cost, if it’s even possible post-return, typically dwarfs what it would have cost to plan properly in advance.

Property: Both Sides of the Balance Sheet

There are two distinct property problems for returning expats.

The first is what they’ve held while away, an Australian property rented out during the absence.

Depending on how long the property was the main residence and how it was treated during the rental period, the CGT calculation on eventual sale can be complex.

The six-year absence rule provides some relief, but it’s not automatic and has conditions that are frequently misunderstood.

The second is re-entry into the Australian property market.

After years of asset accumulation offshore, many returnees assume they’re well-positioned to buy.

The challenge is that their financial picture, including foreign income history, offshore assets and currency, doesn’t translate neatly into Australian mortgage serviceability.

Lenders read foreign income conservatively, and what looks like a strong balance sheet can create unexpected borrowing capacity issues.

The Fix: Plan Before You Land

The single most effective thing an expat can do is start planning the return 12 to 18 months before departure.

That timeline allows for managed asset disposals under non-resident rules where advantageous, superannuation catch-up strategies, foreign structure rationalisation, and property decisions that aren’t being made under time pressure.

The irony is that most Australians sought financial advice before they left on how to exit cleanly.

Far fewer seek the same rigour on the way back in. Given the complexity involved, that’s an expensive oversight.

Coming home should be a financial clean slate. With the right planning, it can be. Without it, you’ll spend the first few years back unwinding decisions that didn’t have to be problems at all.

Brett Evans is the founder of Atlas Wealth and the author of The Expat’s Handbook.