24. The Upgrade | Weekly - The Paradox of Being a Female Leader in Travel

Why is an industry that is largely dominated by women led by so few of us?

🗝️ The Upgrade | Weekly by Anne Marie Brown

24. The Upgrade | Weekly – The Paradox of Being a Female Leader in Travel

Travelers,

I have held various leadership and board positions in the travel and hospitality industry over my career. Yet, agency owner may be the most challenging, perhaps due to the time in my life that collides with this position.

Today’s Upgrade addresses an innate paradox I’ve noticed: the industry is dominated by women, yet structurally makes it difficult for them to run it.

On the surface, the travel industry is an attractive career path. Travel advising, specifically, allows us to combine ambition with flexibility. We can ostensibly work from anywhere, set our own hours, and in some cases, be our own bosses. That flexibility is exactly why 80 percent of advisors and 70 percent of agencies are female-dominated. However, scaling past solo-advisor size requires being the 24/7 person who takes calls on the weekends and family trips, often being a content creator or at least the author of a newsletter, and steps away for “just a second” from dinner. This isn’t a trade off many of us are willing to make once we have children, and for those of us that do try to juggle it all, the stress and guilt are often overwhelming.

The Lobby Bar this week covers Rosewood Hong Kong's repeat win atop the World's 50 Best Hotels list, Ritz-Carlton Residences’ conversion in Brooklyn Heights, the posthumous opening of Dolly Parton's SongTeller Hotel in Nashville, a look at how new luxury hotels get built in Venice, and PURE Life Experiences wrapping its four-day run in Marrakech.

Happy Travels -

Anne Marie

Yours truly, with my two children in the Dolomites

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🗝️ Pre-Departure — Hospitality Hot Takes

The Paradox of Being a Female Leader in the Travel Industry

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I was 33 by the time I had our daughter, and 35 when my son arrived, following years of unsuccessful attempts to get pregnant. My doctor told me I needed less stress. I was traveling most of the year for work. My pregnancies and deliveries were difficult. None of it was easy, but I reminded myself that I had chosen this and longed for motherhood for years. I had quit my corporate career in luxury travel in order to be a mom.

Today, I am 41 with two incredible children, six and eight years old. I love them, but I’m faced with a constant tension between wanting to soak up every minute with them while also being completely obsessed with, and proud of, what I’m building.

Case in point: I missed my son’s birthday this week for a work trip that I very much wanted to go on. Facing his tears as I departed, I smoothed back his hair and told him that mommy had worked very hard to earn this opportunity, and that I would celebrate with him at his party that following weekend when I returned. I could feel my heart ripping out of my body as I ducked into my Uber.

The Trade Off

On this top-producer trip to Rosewood Mandarina, I’m surrounded by other millennial female agency founders who are also navigating motherhood and business ownership. These are some of the heavy hitters in our host agency, other affiliate agency owners who are putting up astronomical numbers and who have built travel businesses most agents won’t create in a lifetime.

At dinner on my final night, we discuss perimenopause, HRT (hormone replacement therapy), school sports schedules, and the push and pull of handling both parenthood and clients. It feels like someone always needs us. We answer client calls in the middle of the night, step away from family dinners, and work on every vacation. My daughter asks me why I’m on my phone on Labor Day weekend while we are at the lake. Under the dinner table at Rosewood Mandarina, I’m currently handling a client who was booked in a room category below what he thought he was getting.

Our dinner conversation turns to marriage. Some of us mention that our husbands aren’t happy with how much we travel and leave them to solo parent. I am reminded that my part-time job has quickly become a full-time obsession.

When we travel, we often operate as what Alex Barnes, another agency owner who has built a huge following on Instagram, calls “luxury backpackers.” We jump from hotel to hotel to squeeze in as many site inspections as possible. In between, we scramble to answer client emails and hop on calls with our teams to problem solve.

There is no “off” switch.

I look around the table and wonder, is it possible to be the primary parent, or even the equal parent, and run a luxury travel agency? Or are we just one step away from burnout, held together by duct tape and husbands who handle more than half the mental load?

We all arrived at agency ownership by way of quitting demanding corporate jobs that we found unfulfilling, transitioning from law, finance, and sports management. Having reached the upper levels of our industries, we wondered if office life was all there was. We are the quintessential millennial overachievers who executed the playbook - straight A’s, college, graduate degrees, high-powered jobs, climbed the ladder.

None of us started out hoping to become full-time travel advisors. We quit the rat race vowing to fill our days with mahjong, tennis, and taking care of ourselves for once. I left to take care of my parents until they passed away and try to make a go of a writing career, oh and to have a family. I made it five years before I started feeling like I’d lost a piece of myself, my larger purpose in my days.

I'd already spent a decade in luxury travel before I tried to leave it the first time. I went back to work after my daughter was born, then built a travel tech platform with my husband that failed when Covid hit, then swore off the industry again, until a friend asked me to help expand her agency in 2025. It was supposed to be a part-time gig with a short timeline. I laugh at that now.

Is balance at scale possible?

Around the table at Rosewood Mandarina, the women all agree: our second careers seem to have blown up into behemoths once we attacked them with the same drive we brought to our previous jet-fueled jobs.

Most of us work out of home offices with little privacy. My children come home from school, completely ignoring the Ritz “Do Not Disturb” sign on my door, and rush into the middle of client calls. I scoop them up for a quick hug before shooing them off to another room. I work for two more hours, our nanny shuttling them to after-school activities, before I step away to help with dinner and bedtimes.

My commission this year covers our nanny’s pay, with a respectable cushion to spend on our travel budget. The irony of spending most of my income on childcare when I worked so hard to become a mother is not lost on me.

Surrounded by these other badass female founders, I finally feel like I have a place to talk about all this.

The Industry Runs on Women, But Leadership Trends More Male

This tension we are feeling is part of what drives the dearth of female leaders in the travel industry. Travel is a largely female dominated industry. Roughly 80 percent of U.S. travel advisors identify as female¹, and women own about 70 percent of the nation's agencies². However, that 70 percent is comprised mostly of solo operators or small teams working from a home office, like mine.

In the companies with scale, the numbers reverse. Women held 28.4 percent of board seats at publicly traded hospitality companies in 2025⁴, and, among Virtuoso's largest member and host agencies, the top job at only five of thirteen I checked (two of which now sit inside larger corporate parents). Executive committees are worse. AETHOS Consulting found female representation across hospitality leadership teams at 22 percent⁵, and a UK study of top FTSE 350 hospitality companies found only 4 percent had a woman as executive director⁶.

Women make up 74 percent of travel buyers and more than half of supplier and travel management company staff⁷. We're most of the industry's front line and its client base, and a minority of who runs it.

In Jacques Ledbetter’s Luxe Ledger: Private Edition and Forbes article about women in hospitality, he included the image above. “11 travel executives spanning hotels, airlines, casinos, cruise and online travel met the U.S. President in the Oval Office and stood shoulder to shoulder for a picture that’s been widely circulating across the travel and hospitality industries. There were no women among them.”

The person building your luxury travel itinerary is nearly always a woman.

The person who owns the company she works for, or the hotels she is booking, usually isn’t.

Why Is This Happening so Starkly in Travel and Hospitality?

Is it a matter of opting out of leadership roles once we realize what they will take in the travel industry? Or is that opportunities that are more likely to be provided to male counterparts because of the perception that we as women would prioritize families over executive demands?

I recall fighting for a VP position that, in my mind, I had earned at a previous company through two years of demonstrated growth and leadership. Surrounded by male peers who had been promoted to that level with lesser accomplishments, I asked for title change. I was told that I was “too assertive” for the executives to recommend me for the higher role. Many women in similar positions have received feedback about being too “assertive, direct, emotional, cold, or hard”. Among my male friends from business school, none of them had ever received that feedback.

I think the answer is: all of the above. Yes, I have been thwarted from advancement at various stages in my life, and I have pivoted due to personal choices, such as stepping back for a few years to take care of my parents and kids.

The other female founders at the Rosewood Mandarina event and I discussed whether it’s possible to create boundaries with clients around work and personal time. The consensus was that it’s possible if you have a team of employees and perhaps pay for an after-hours service, but that almost inevitably, the buck stops with us. If we book using a DMC (destination management company), the client has an in-country contact during their trip, which adds a layer of protection. Yet we still receive the escalations.

Whitney Haldeman, founder of Blonde Atlas, Atlas Adventures, and The Heart of Travel, and I sat down together when I was in London this summer where she allowed me to pick her brain about how she is handling agency ownership. I’ve been a fan of her Substack for a while, and wanted to hear her perspective on this topic.

Her full interview will be published as Master Key piece later this week, gifted to everyone, not just paid subscribers.

At a certain level, the travel industry is a 24/7 job, but we trying to manage it better

Yes, this job comes with great flexibility, and we can do it from anywhere. I worked from a pool last week. Alex Barnes is working from Switzerland this week. Whitney just got back from Morocco. The downside is that our work also follows us everywhere. My screen time is 11 hours a day, and my brain is half present at the best of times. It’s difficult to schedule time with friends because I’m often out of town, and many of my friends are my clients (which I greatly appreciate).

That leads to the next thing the group of leaders at Rosewood Mandarina kept coming back to, which is mental health. Most of us mentioned having a therapist (marriage or personal) and making specific time to exercise or take a daily walk at minimum.

In our former corporate lives, we had finance, accounting, marketing, legal, and support teams behind us. Now, we handle every stage of the booking and operations process, plus every business management and ownership role. We may outsource bookkeeping and social media, or have an offshore VA (virtual assistant), but even the most successful among us are handling many more facets of our businesses than we did in our previous roles.

I, personally, feel pulled nonstop in all directions, like there’s never enough time in the day. I wake up every night between 2 and 4 am, my brain going a million miles an hour. I used to answer emails in those hours, but now I use the time to write these Substack articles, which feels better for my mental health.

I’m trying to become more intentional about setting my out-of-office replies, blocking my calendar when my kids come home, and pushing clients from text messages to emails during work hours. I’ve begun using Calendly to schedule calls because that way I’m less likely to book them over my “dedicated” family time.

It's difficult to disconnect on evenings and weekends because travel planning at this level is personal, and clients make buying decisions over margaritas with friends on a Saturday night. When I am the brand they're buying, they want access to my brain exactly when I'm supposed to be at the dinner table. Rates change hourly, inventory disappears over a weekend, and something always goes wrong, a flight delay, a human error, somewhere in a hundred moving pieces.

One of the other agency owners, who doesn’t have kids, wondered aloud whether she could dedicate more time to clients than those of us who are moms. Kylee Glaser, my business partner at Alpenglow, and I answered that while we are intentional about our work time and home time, we don’t let our kids’ schedules affect our client service. We are, perhaps, more efficient with our time because we know it is limited. Bedtimes are sacred in our house. I go to sleep early, right after tucking in my kids, knowing I’ll wake up in the middle of the night.

I still have to justify the tradeoff to myself.

On the positive side, my children see me doing something I love. If I need to, I can block time for a mid-day school meeting or Halloween party in the classroom. I’m not beholden to PTO restrictions. I tell my kids, Mommy doesn’t have to work. She chooses to work.

The second benefit of this career that I like to highlight is that my kids benefit directly from my work. When I held a corporate role, my home life and work life were quite separate. Had I stayed, I’m not sure how much my kids would have connected the work I did to anything in their own lives. As an agency owner, I tell my kids that the reason we get to travel as much as we do is because mommy works hard planning travel for clients. If they want to go back to Paris for their next birthday, mommy has to sell more travel.

Kylee put it this way: it’s important for her to expose her kids to what’s possible in luxury travel, and she hopes it inspires them to work hard and strive for a life where they can reach that same level.

I am raising tiny luxury travelers. My daughter accompanies me on site inspections if I meet with a hotel sales team on a family trip. My kids, the original Bougie Bunnies (check old posts on my substack for this cartoon series I created), have stayed in more five-star hotels than most adults will in their lifetimes. They have opinions on caviar and hotel check-in processes. Traveling with them for work also leads to interesting conversations, like why they see more cigarettes in Paris than at home in Colorado.

At the same time, they know that I gave up time with them after school to bring them to those places. I make sure they connect the two. If I have to bring my phone to the playground, I make sure to explain why to them. I’m not on my phone because I’d rather be scrolling Instagram than spending time with them. I’m answering emails because people are counting on me. I tell them about my clients’ trips, what those families are celebrating, and what I’ve built for them.

I must be doing something right, even if I feel like I’m dropping balls all over the place, because my daughter said recently that she wants to take over my business one day. As a kid who grew up wanting to be the CEO of my family’s hotel company, but never made it to that leadership position before we sold it, my little heart burst with pride realizing I’m building a company my daughter is proud of too.

TLDR:

Thank god for my husband, who is picking up the pieces as I try to hold it all together with duct tape and hope.

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🗝️The Lobby Bar

Hospitality updates, promotions, gossip, and the occasional pun

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"What job did the frog have at the hotel?" "Bellhop."

• Rosewood Hong Kong topped the World’s 50 Best Hotels list for a second year running. I have lots of big feelings about “Best Of” awards, and am working on article about the awards business in general. The TLDR for the lobby bar is that Capella Bangkok and Four Seasons Bangkok at Chao Phraya River took second and third, and fourteen properties are new to the list this year. Lots of city hotels. Some weird rankings.

• Marriott is turning a Brooklyn Heights landmark into residences. Because branded residences are all the rage, Marriott and developer SomeraRoad plan to convert the former Hotel Bossert into a standalone Ritz-Carlton Residences property, with completion targeted for 2029.

• Dolly Parton’s SongTeller Hotel opens September 29 in Nashville. RIP to the queen of Nashville, and one of my all-time inspirations. I grew up going to Dollywood and am absolutely going to visit this hotel. The property, built around her songwriting catalog through Herschend Family Entertainment, now debuts a month after her death on August 25.

• Every piece of furniture in a new Venetian hotel arrives by boat. Ok so this isn’t really news, but I think it’s a cool take on all the luxury hotels opening in Venice this year and how they came to be renovated. AFAR toured three new luxury openings, Airelles Palladio, the reopened Danieli under Four Seasons, and Orient Express Venezia, tracing how marble tables get lifted through windows by crane on a city with no roads to build on. (Laura Rysman, AFAR)

• PURE Life Experiences wrapped its four-day run in Marrakech. The invitation-only experiential travel show ran September 7 through 10, pairing roughly 1,800 travel designers and specialist operators through custom diaries of up to 45 one-to-one meetings each. I have not yet scored an invitation, because The Upgrade has 1,100 of you wonderful readers and is not yet an industry-wide phenomenon. A girl can hope.

Sources

1. Host Agency Reviews, “2021 Travel Advisor Demographic Report.” https://hostagencyreviews.com/blog/2021-travel-advisor-demographic-report

2. American Society of Travel Advisors (ASTA), International Women’s Day post, via LinkedIn. https://www.linkedin.com/company/american-society-of-travel-advisors

3. Rachel Louise Ensign and Chelsey Dulaney, “The Rise of the Unstoppable American Tourist,” The Wall Street Journal. [ADD LINK]

4. Penn State School of Hospitality Management, 2025 hospitality leadership report, via Hertelier. https://www.hertelier.com/post/women-hotel-leadership-stalled-2025-penn-state

5. AETHOS Consulting Group, “Women’s Presence Growing in Hotel Boardrooms,” via Hotel Management. https://www.hotelmanagement.net/operate/aethos-report-shows-women-s-presence-hotel-boardrooms-up-but-not-enough

6. GBTA Foundation and WINiT (Women in Travel), October 2025 study, via Meeting Spotlight. https://www.meetingspotlight.com/research/gbta-study-shows-ongoing-barriers-womens-advancement-business-travel

7. Jacques Ledbetter, “The Women Hospitality Leaders Who Should’ve Been In The Room,” Forbes, September 8, 2026. https://www.forbes.com/sites/jacquesledbetter/2026/09/08/the-women-that-shouldve-been-in-the-room/