02 July 2026
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“I want to move to the woods. Find a cabin, turn it into a hotel, and live like that for the rest of my life,” says my friend of twenty-plus years, with a not-so-subtle hint of exasperation. "I've been staring at spreadsheets all week, and my coworkers make me want to — "
I’ll end the quote there, with me chewing on my chocolate croissant, deciding whether to tell her my thoughts or keep my opinions to myself. As someone who speaks to hoteliers for my own job, not to mention someone who enjoys television, I know the dream she’s getting at. Schitt's Creek, Gilmore Girls and Newhart are three examples in three different decades that play with elements of an enduring fantasy: to move to a small town, open a little, character-rich inn, and escape the rat race into a world of antique hunting, fabric designs and human connection.
My friend looks at me with hopeful eyes.
“What do you think? You write about hotels for a living.”
The reality, of course, is that opening and running a hotel isn’t just a full-time job. In many cases, it becomes your life. The question then is simple: Is it worth it? I spun my rolodex and spoke to six hoteliers who made the move. Among them, they left careers as doctors, executives and wedding planners. I set out to find the truth.
That’s not what I budgeted
“Like every great project, the final cost was considerably higher than our initial estimate.” — Michela Mola, Singer Palace
Let’s start with the obvious. It takes serious, ballooning, cry-yourself-to-sleep investment to start a hotel from scratch. First, of time and effort. The hoteliers I spoke to for this story consistently described a never-off-the-clock feeling. But that’s a given. What I want to talk about first is cold, hard cash. Nearly everyone we spoke to agreed they ended up spending more — much more — than projected. One said she came to consider budget as purely theoretical, like the great philosophical writing of a Kant or Sartre, interesting to consider but impossible to implement. Another nearly went bankrupt in his first year.
The married couple behind the Rex, in a rural hamlet of America’s Poconos Mountains, bought an old motel and moved on property the day after closing, scavenging for used furniture to fill their own unit as they poured money into renovations. Of her time bringing the old Singer sewing machine headquarters back to life, Michela Mola notes, with a certain understatement, that “historic buildings have a way of revealing new opportunities — and new expenses.” For Caryn Hibbert, a former doctor-turned-hotelier at Thyme in the Cotswolds, the bulk of the cost was hidden in essential infrastructure systems like plumbing and electrical wiring.
Friorik Pálsson, once a CEO at one of Iceland's largest fish exporting companies before opening Hotel Ranga, reminds us that there’s another, and critical, pit in which to throw your money: marketing. He credits that particular strategy as saving his business in the wake of the pandemic.
Owning a hotel, no matter the scale, is much more business than romantic escape. Only one hotelier we interviewed came in on-time and on-budget. Her secret? A solid development partner scrupulous of every line item and a conservative contingency budget. Yes, even the dream job has that annoying coworker who won’t shut up (and is right).
From funky fabrics to septic tanks
“Far harder than we imagined.” — Maria Sole Cecchi, La Gemma in Florence
The Rex, the hotel in the woods of Pennsylvania mentioned above, has a creation story that is perhaps the quintessential hotel dream as imagined in pop culture. Brian Linton, who founded the 10-room hotel with his wife, Joanna, quit his job after the couple fell in love with their rental place in the forest nearby. In a flash, they had bought an old motel and taken the plunge. They began renovations the next week, and rushed day and night to get the place up to standards for a summer opening — a financial necessity. Looking back, you can hear disbelief in Linton’s reflection: “It was a little impulsive.”
Perhaps they should have bought a place more polished, instead of a rundown motel that was, to put it mildly, a bit of a fixer upper.
Here’s the thing: they’re all fixer uppers.
“When my husband first walked in…” says Mola of the Singer Palace, “it was empty, dusty and seemingly forgotten.”
Empty, dusty, forgotten, dirty, neglected, sad — these are the words hoteliers use to describe the spots they can actually afford for their dream projects. After purchase comes the admin work: securing permissions, working with building regulations, dealing with all the minor and major realities of hotel life. If what you’re running from is the ever-confusing world of technology, you won’t escape it by opening a hotel. In Rome, Mola continues learning the complex language of hotel management systems, revenue management tools, CRM platforms and channel managers.
But if what you’re running from is monotony, look at it this way: every day is a new challenge. Audrey Gelman, whose Six Bells Countryside Inn sits in a rural area of New York, says she’s now nearly fluent in the functionality of septic systems. Granted, the problems don’t always come with solutions. When David Leventhal opened his hotel, Playa Viva, he looked forward to marketing a space along a pristine strip of Mexican coastline. At one point, the media labeled it a narco warzone (today, Zihuatanejo is back in good standing — and Playa Viva has Two Keys).
Slowly or frantically, in bursts or with steady persistence, every successful hotelier can speak of the importance of keeping a final vision firmly in mind. Hibbert puts it succinctly: you have to just dive in and do it.
Do you really want to open a hotel with your brother?
“I'm easily sort of distracted by the next shiny object. And my wife is the one that actually keeps things on track.” — Brian Linton, The Rex
You’ll need partners. Likely, you’ll need many of them. And though I’ve learned through this process just how much even a tiny hotel runs on the same juice as any type of business, this is where the hotel game looks a little different. It’s extremely common for small hotel owners to start their project with family.
It’s an experience many — and we’ll keep them anonymous here — describe as tricky and confrontational, but not without its joy and motivations. It’s the aligned values and a deep sense of trust that make a family member the ideal partner in this business, as well as the fact that they’re likely used to years and years of seeing you at your worst.
The ability to forgive quickly is key: the five brothers and sisters running Hotel La Gemma in Florence have been practicing with one another from childhood. “Working together puts you face to face with each person's strengths and fragilities,” says Cecchi, adding that it helps to be direct.
And if you work with anyone else, pretend they’re family anyway. Several hoteliers cited surprise at just how much intuition their guests show. If something’s off in the behind-the-scenes dynamic, it affects the atmosphere of the hotel itself. If staff are happy and joyous, they feel that too.
Do it anyway.
“Be scared, but do it anyway.” — Audrey Gelman, Six Bells Countryside Inn
The challenges are many. The investment is higher, in time and money, than nearly any other career. And still, 100% of our interviewees say they’re unequivocally happier than they were in their former roles. Despite working more than ever before, despite the relentless thoughts of guests and budgets and system failures — each and every one says they would do it again in a heartbeat. And we believe them. The reward is that good. Like an artist, you’re creating something beautiful, guided only by your vision and the practical journey to turn it into reality. Mola calls the process the “most beautiful [of] adventures.”
Could you do it?
Established now and successful, the hoteliers here are already thinking about trying again, and they haven’t lost any ambition. Maria Sole Cecchi of La Gemma itches to try her hand at a seaside boutique in Sicily. Leventhal of Playa Viva is chomping at the bit to expand his regenerative hotel concept to a competitive market in Baja California Sur. Caryn Hibbert, of Thyme in the Cotswolds, dreams of a low-impact lodge in the African bush.
There’s something addictive about this lifestyle. That much is clear. Knowing the hardships, I can’t quite recommend it to my friend who inspired this piece. Not, at least, without a lot of caveats. And yet…
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Header Image: On the left, Playa Viva's founder David Leventhal. On the right, Audrey Gelman of Six Bells Countryside Inn, with designer Adam Greco. © Playa Viva, Six Bells
