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 favorite 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.

As tech leaders race to bring Windows systems back online after Friday’s software update by cybersecurity company CrowdStrike crashed around 8.5 million machines worldwide, experts share with CIO Journal their takeaways for preparing for the next major information technology outage.

Be familiar with how vendors develop, test and release their software

IT leaders should hold vendors deeply integrated within IT systems, such as CrowdStrike , to a “very high standard” of development, release quality and assurance, said Neil MacDonald , a Gartner vice president.

“Any security vendor has a responsibility to do extensive regression testing on all versions of Windows before an update is rolled out,” he said.

That involves asking existing vendors to explain how they write software, what testing they do and whether customers may choose how quickly to roll out an update.

“Incidents like this remind all of us in the CIO community of the importance of ensuring availability, reliability and security by prioritizing guardrails such as deployment and testing procedures and practices,” said Amy Farrow, chief information officer of IT automation and security company Infoblox.

Re-evaluate how your firm accepts software updates from ‘trusted’ vendors

While automatically accepting software updates has become the norm—and a recommended security practice—the CrowdStrike outage is a reminder to take a pause, some CIOs said.

“We still should be doing the full testing of packages and upgrades and new features,” said Paul Davis, a field chief information security officer at software development platform maker JFrog . undefined undefined Though it’s not feasible to test every update, especially for as many as hundreds of software vendors, Davis said he makes it a priority to test software patches according to their potential severity and size.

Automation, and maybe even artificial intelligence-based IT tools, can help.

“Humans are not very good at catching errors in thousands of lines of code,” said Jack Hidary, chief executive of AI and quantum company SandboxAQ. “We need AI trained to look for the interdependence of new software updates with the existing stack of software.”

Develop a disaster recovery plan

An incident rendering Windows computers unusable is similar to a natural disaster with systems knocked offline, said Gartner’s MacDonald. That’s why businesses should consider natural disaster recovery plans for maintaining the resiliency of their operations.

One way to do that is to set up a “clean room,” or an environment isolated from other systems, to use to bring critical systems back online, according to Chirag Mehta, a cybersecurity analyst at Constellation Research.

Businesses should also hold tabletop exercises to simulate risk scenarios, including IT outages and potential cyber threats, Mehta said.

Companies that back up data regularly were likely less impacted by the CrowdStrike outage, according to Victor Zyamzin, chief business officer of security company Qrator Labs. “Another suggestion for companies, and we’ve been saying that again and again for decades, is that you should have some backup procedure applied, running and regularly tested,” he said.

Review vendor and insurance contracts

For any vendor with a significant impact on company operations , MacDonald said companies can review their contracts and look for clauses indicating the vendors must provide reliable and stable software.

“That’s where you may have an advantage to say, if an update causes an outage, is there a clause in the contract that would cover that?” he said.

If it doesn’t, tech leaders can aim to negotiate a discount serving as a form of compensation at renewal time, MacDonald added.

The outage also highlights the importance of insurance in providing companies with bottom-line protection against cyber risks, said Peter Halprin, a partner with law firm Haynes Boone focused on cyber insurance.

This coverage can include protection against business income losses, such as those associated with an outage, whether caused by the insured company or a service provider, Halprin said.

Weigh the advantages and disadvantages of the various platforms

The CrowdStrike update affected only devices running Microsoft Windows-based systems , prompting fresh questions over whether enterprises should rely on Windows computers.

CrowdStrike runs on Windows devices through access to the kernel, the part of an operating system containing a computer’s core functions. That’s not the same for Apple ’s Mac operating system and Linux, which don’t allow the same level of access, said Mehta.

Some businesses have converted to Chromebooks , simple laptops developed by Alphabet -owned Google that run on the Chrome operating system . “Not all of them require deeper access to things,” Mehta said. “What are you doing on your laptop that actually requires Windows?”