• I booked two separate flight itineraries on different airlines for a family trip to Ireland.
• I realized this was a mistake after the first airline diverted, and the second left without us.
• The fix cost my family nearly $3,000 in new tickets and a day's worth of touring.

I'm a veteran traveler who has booked more long-haul flights than I can count. But earlier this year, I made a very expensive rookie mistake.

While planning a trip, I came across a deal I couldn't pass up: a $317 one-way flight on Icelandair to Ireland with a multi-day layover in Reykjavik. It was essentially a way to take a trip within a trip without paying extra airfare.

The catch? The flight departed from New York, not our home airport in Florida. I'd be in New York a few days early, but my family would need to fly up to meet me. Booking separate itineraries was far from ideal, but I figured a five-hour buffer would be enough.

It wasn't.

A storm in New York canceled my family's JetBlue flight from Florida, and their replacement flight then couldn't land and was diverted to Virginia. Their Icelandair flight to Europe was automatically canceled after they were marked as no-shows.

On the night we were supposed to fly together to Iceland, my family was stuck states away, and I was scrambling to find a solution.

With my family's original flight gone, we had to spend nearly $3,000 to get them back on track and navigate the complicated credit card trip insurance process. Here are 4 lessons I learned the hard way.

Booking separate itineraries comes with a pricey risk

Arriving in the city of your next flight at least 24 hours before may feel a bit extreme, but it's the minimum safety net you need.

Being already in the right location for your flight can be a huge weight off your shoulders. It also allows sufficient time for rebooking should something go wrong with your flight.

My last-minute whim to visit a few friends upstate turned out to be key. Those extra two nights in New York meant I was able to make the flight to Iceland. If I had booked my family of three on a flight the day before our long-haul flight, they would have made it too.

My family made it to New York the next morning and ended up taking a replacement flight to Iceland that evening, getting in about 24 hours later than originally planned. I bought two basic economy tickets for $734 each, and one standard economy ticket with extra baggage allowance for $1,105. In total, I spent $2,573 on new tickets.

The costly mistake made me realize that although an extra hotel night is an added expense and may mean using more PTO, it's a cheap investment compared to the cost of new international flights — and the cost of missed events — if things don't go to plan.

This is especially worth it if you have definite plans right after your arrival, such as a cruise or a concert.

Neither airline has to help in my scenario

When you book connecting flights on a single itinerary, the airline is responsible for getting you to your destination. If you miss that connection through no fault of your own, then the airline will put you on another available flight at no additional cost.

When you book flights separately, you're responsible for making each connection — or buying new tickets if you miss one. And generally, regardless of reason, the airline operating your next flight isn't obligated to accommodate you if you miss it because of a problem with your previous airline.

Our tickets to New York and Iceland were separate, so despite numerous calls to each airline, none were responsible for the missed connection. If you do miss a connection on a single booking, look up alternatives yourself and discuss them with the agent. It's not guaranteed, but they may be able to accommodate you on a partner airline at a more convenient time.

And remember, it's not the staff's fault for the disruption. You get more bees with honey.

I should have read the fine print

I didn't book the cheapest fare, but I didn't read the fine print either.

When things started to go wrong, I was shocked to see there was a $250 change fee per person on my original flight and no refunds. Changing the tickets would have cost nearly as much as the original flight, plus the fare difference.

At the time, it was uncertain when my family would actually arrive in New York and feasibly be able to catch the next flight to Iceland, so we didn't change the tickets. Missing the first flight on this stopover itinerary meant my family was marked a no-show and their onward leg to Dublin was canceled, which is standard airline policy.

While there were other ways to get to Iceland, there were few nonstop flights from Iceland to Ireland — a one-stop meant at least four extra hours of travel — so the best option was to book a new stopover ticket with Icelandair.

When I started booking the new tickets, I noticed that almost every fare class had punitive cancellation and change policies — and this time I was sure to be familiar with the terms of my booking.

I need to better understand my credit card's trip protections

Premium credit cards can have your back when flight plans go wrong, but they don't cover everything.

We used the Chase Sapphire Reserve for Business' trip cancellation and interruption protection for the original Icelandair tickets and were reimbursed $952. The coverage typically reimburses covered unused, prepaid expenses — but not the cost of buying new airline tickets.

Trip delay coverage doesn't either, but it can cover other expenses for covered trips. However, credit card policies vary — and this is where I went wrong.

We booked the flights to New York on an American Express Business Platinum Card but used a different card for the return flights. That meant the Amex trip-delay protection did not apply: its terms require the full round-trip fare to be charged to the eligible card.

I had split the flights across cards to preserve Chase's bag-delay protection, but I didn't realize I was giving up the Amex protection in the process, so the $103 spent on dinner after the diversion wasn't covered. For future trips, I'll use only one credit card with good travel protections for all my trip expenses to reduce complications.

Airlines may also provide some compensation for flight disruptions. In our case, my family was reimbursed for a hotel stay ($185) on the night they were diverted. When delayed, I always keep receipts of all my added expenses to submit to the appropriate parties.

Overall, although our vacation had a rocky start and cost more than we planned, we had a great trip and are glad we pushed through it.

Missing a flight always seems avoidable in hindsight, and some things are beyond anyone's control, but with a few precautions, we can travel more confidently. Next time, I'm booking the extra hotel night.

After 20 years of balancing her corporate leadership roles with motherhood, Trisha Daab was ready for a break.

"Life had felt like sprinting a marathon for as long as I could remember," Daab, 47, told Business Insider. "I had no idea how tired I was until I stopped working."

In her year off, she tap danced, volunteered at a food bank, traveled to Disneyland and Alaska, and spent more time with her kids. By the end, she had decided she couldn't go back to her old life.

"My job often demanded that it came first — never-ending to-do lists, urgent emails, travel, and always chasing the next promotion," Daab, who's now a travel writer and substitute teacher, said. "Stepping away helped me realize my priorities had shifted."

Now in their 30s and 40s, many millennial women are skeptical of corporate and instead becoming business owners, content creators, and mothers, prioritizing more flexible work schedules. Instead of striving to get to the top, they're inverting Sheryl Sandberg's mantra of the 2010s — and leaning out.

Sandberg, Meta's former COO, told Business Insider that the corporate exodus is due to women feeling undervalued at work.

"This is not the women who are saying, 'I don't want to do it,'" Sandberg, 57, said. "It's the women saying, 'I don't want to do it because I'm not wanted, I'm not getting the same opportunities and the same support, and I face an unfair burden at home.'"

Even Lean In, the organization founded by Sandberg and named after her 2013 bestselling book, is noticing a recent shift in women's ambitions in the workforce.

According to the organization's 2025 Women in the Workplace report, published in December 2025, which surveyed 9,500 US employees across 124 organizations, women were less likely to say they wanted a promotion compared to men. This was true when filtered to include only millennials, who made up roughly one-third of participants.

When asked why, over 28% of millennial women said "personal obligations" made it hard for them to take on more — compared to 17% of millennial men.

Annie Wright, a licensed psychotherapist who works with Silicon Valley leaders, has also observed more of her millennial female patients shifting their ideas about what constitutes a fulfilling career.

"I'm watching them make more person-centered choices than necessarily career-only-driven choices," she told Business Insider. "I don't think many millennial women are becoming less ambitious. I think they're just becoming less willing to confuse ambition with self-erasure."

The rise and fall of the have-it-all girlboss

Let's, for a moment, remember what is now referred to as the "girlboss era" of the 2010s.

It was a time of She-E-O-led startups, of crushed velvet sofas and the words "I Want It All" aglow in cursive neon lettering. Of earnest enjoyment of "Fight Song" and T-shirts with earnest phrases like "feminist" and "woman up."

Of a future that was female, tinged millennial pink — until a series of public reckonings punctured the fantasy. Leaders of several companies stepped down amid allegations of toxic workplace cultures, exposing the facade of the girlboss promise.

Then came the remote work culture of 2020. Suddenly, many women had time to breathe, whether that meant not rushing to day care pickup, having more time to work out or see friends, or simply not being "on" all the time.

For some, the slowly creeping requirement to return to the office dealt the final blow.

Misty Heggeness, a professor at the University of Kansas specializing in gender economics, described the influx of new RTO policies by some companies as having a "chilling effect."

"That does disproportionately disadvantage women in general," Heggeness told Business Insider, "just because women are more likely to carry an invisible load of work within families."

The working mom paradox

After the birth of her first child, Kendra Rothermel switched from full-time to part-time work as an office manager while her husband remained at his full-time job. "As we grew our family, it made sense for me to have a more flexible schedule," Rothermel, 34, told Business Insider.

When she had her third baby, his clubfoot diagnosis meant frequent orthopedic appointments. Even part-time work wasn't flexible enough, so she eventually started her own venture helping small businesses with operations and marketing.

Rothermel said she was partly inspired by watching other working moms do the same.

A recent analysis of job-market data by Matthew Nestler, a senior economist at KPMG, found that labor force participation between December 2023 and May 2026 decreased among college-educated women with children under 5. Meanwhile, participation increased for women without children and most groups of men, including fathers.

Because millennials are generally having kids later than previous generations did, Heggeness said parents, moms in particular, are more likely to be parenting young children just as their work responsibilities are ramping up.

"If they were going to lean out, now would be the time," she said, whether it's to save on childcare costs or introduce more flexibility.

Add to the list aging parents. The costs of childcare and eldercare, sometimes unaffordable even with the intense work commitments required to afford them, have prompted some women to leave their full-time jobs for more flexible or minimum-wage work.

To Sandberg, it's a sign that companies are not adequately adjusting to meet women where they are, whether that's offering more flexible hours, longer parental or bereavement leave options, or better healthcare coverage.

"We're at a critical moment in time for women, because what a lot of women are seeing is that commitment to them in leadership pulling back," Sandberg said. "Then what's happening to them is their ambition is pulling back. And that's a loss. It's a loss for our economy. It's a loss for our companies. It's a loss for our children."

The allure of going at it alone

Not all women who are leaning out are doing so because they are overworked. Some, like Heigi Jeong, 30, have dreams beyond corporate America.

"While I wouldn't say I loved the work, I liked it," Jeong, who made $173,000 working in product design, told Business Insider. "It was my dream job as an immigrant, and it was sustainable."

Still, Jeong was pulled toward her other ambitions: writing a book and being a content creator. She was also intrigued by the idea of being her own boss.

"When I'm working for myself, I entirely choose the role I will play," Jeong said. "I wanted to experience it myself and have my own take rather than constantly wondering 'What if I quit?'"

Three months after quitting, she enjoys not feeling as rushed as she used to, even if the price is an inconsistent income.

Both Heggeness and Wright have noted a growing interest in entrepreneurship and self-employment among women. A 2024 Census working paper found that the share of women business owners under 45 rose between 2012 and 2020, with the biggest increase among women ages 25 to 34. It also found that newer women-owned employer businesses were disproportionately owned by women under 35.

The creator economy opened another path. More than 200 million people worldwide now identify as content creators, though that broad figure includes far more than full-time influencers. Some Gen Z and millennial consultants are even leaving MBB and Big Four firms to build audiences and businesses online — trading the girlboss crown for a bubble headband.

In a 2023 Vogue article, writer Daisy Jones wrote that the newest iteration of girlboss swaps grind culture with the similarly perfectionistic "soft life" defined by travel and lucrative brand deals. Pantsuits were exchanged for sweatpants; speaking engagements and spread-thin multitasking gave way to self-care and supplement stacks.

"In some ways, the career woman appears to have been replaced by the health-conscious woman," Jones wrote, "the one who prioritizes her vitamin intake, hydration, and sleep cycle over endless meetings and salary increases."

Content creation doesn't come without its own costs. Plenty of influencers report feeling financially insecure or overworked, unable to take a day off without losing money.

Still, if they're going to burn out or worry about their job security, some figure they might as well enjoy their autonomy to create their own schedules.

"For some women, there's been a paradigm shift in values," Wright said. "Promotion or success now looks like more availability, presence, and freedom."

When everyone leans out

Sandberg, who herself stepped down as Meta's COO in 2022 to pursue philanthropy and early-stage investing ventures, said she supports women's career choices, whatever they may be.

"I think being at home with your children is great," she said. "Going back to school, great. Starting a company, great. Going part-time, great. Anything you want to do is great."

Part of the issue, she said, is that without female leaders, there are simply fewer people to advocate for the very policies that make other women more excited to move up in a company, be it egg-freezing coverage, lactation rooms, or more competitive maternity leave options.

It's why she feels companies need to do more work to assess why women are leaning out enough to jump ship entirely. "It's easy to overly characterize the words 'lean in,'" she said. "What I mean by them is very clear: I think women should make decisions based on believing in their own abilities, based on believing that they should and can have the same opportunities as men."

It's just a shame, she continued, if the decision stems from not feeling valued enough in the corporate world.

"I just hope that enough women want those senior leadership roles," she said, "that we get the environment for women that they deserve."

• I flew on a "boutique" Taiwanese airline called Starlux, and it blew me away.
• The seat was like a private pod, and the food was some of the best I've ever had.
• The crew seemed rushed during boarding, but were impeccable inflight.

I'm a regular business-class traveler, having flown on dozens of airlines and hundreds of thousands of miles over the years.

I often get asked the same question: What's the best business-class seat you've ever flown in?

It's not the usual fan favorites of Singapore Airlines or Emirates. It's Starlux Airlines, a Taiwanese carrier many Americans have never heard of.

Starlux first flew in January 2020 and bills itself as a "boutique" international airline that operates nonstop flights from Taipei to several US cities, including Los Angeles, San Francisco, and Seattle.

My flight was on an Airbus A350-900 from Taipei to San Francisco, a nearly 12-hour overnight flight. It was the second leg of a trip that started in Kuala Lumpur, and the entire itinerary cost 85,000 Alaska Airlines miles.

The cash fare on this route ranges from $2,600 to over $5,000, depending on the season, so the points redemption — Alaska is a Starlux partner — was a very good deal. And the experience blew me away.

The whole idea from the beginning was to build a luxury airline from nothing with meticulous attention to detail and an emphasis on the small stuff.

After flying Starlux, those minor details made all the difference. Here's what my flight was like and why I'd easily book again.

The seat felt like a private suite

Every seat in Starlux's business class opens straight into the aisle, and every one has a sliding door. The cabin is decorated with faux marble finishes and shiny black panels. It honestly looks more like a boutique hotel lobby than the inside a plane.

This extreme attention to detail is what sold me most.

My favorite example: there's a little gap under the storage cabinet door, so you can leave a charging cable running out of it with the door closed. Exploring the seat illuminated several thoughtful design choices. The pod felt deliberate in a way some brand-new airline seats just aren't.

Some people call business class doors a gimmick, mostly because they don't go all the way up. I loved mine anyway. Once the seat was flat and the door was shut, it felt like my own little room, further emphasized by the warm mood lighting, pristine leather accents, and large seat walls.

A flight attendant handed me pajamas before we'd even pushed back, so I changed right away.

After dinner, the crew made up my bed with a thick mattress pad and one of the softest blankets I've ever been given on a plane.

The footwell angles inward slightly, which makes it feel a bit tight when you're lying flat, but I slept well regardless. On an overnight flight this long, that's what matters most.

The food was some of the best I've had in the air

Dinner is where Starlux left every other business-class flight behind.

It started with warm, fluffy garlic bread, which felt out of place alongside the Asian meal, but I was thrilled to see it. When the flight attendant came to clear my appetizer, she asked if I'd like more bread, to which I obviously said yes.

Then a creamy miso mushroom soup showed up, and I'm not exaggerating when I say it's one of the best things I've eaten on a plane. It was rich and savory, the kind of thing I can still taste if I think about it today.

The main was beef with fried rice, which was flavorful and cooked to perfection.

Dessert was Italian gelato that was actually soft enough to eat straight away, which basically never happens with ice cream at 38,000 feet.

Breakfast before landing: waffles with figs were also notable. One of the few airline breakfasts I'd happily order again.

All of the food served looked as good as it tasted. Every course was properly plated, the flight attendant talked me through each dish, and she reset my table between courses without me noticing.

The crew truly elevated the experience

Starlux isn't perfect, and the first 20 minutes of my flight proved it. Pre-flight service felt as if the crew was simply going through the motions rather than trying to create a good experience.

But when the meal service started, it was like a switch flipped.

One flight attendant greeted me by name and knelt down next to my seat to take my order. At one point, my seatbelt locked up while I was reaching for my amenity kit; she saw it happen and handed me the kit before I'd said a word.

My main course came out a few minutes late, and she apologized profusely for it, which she really didn't need to do, but it tells you what standard this crew holds itself to.

By the time dinner was over, even the crew members who'd seemed checked out at first were warm and attentive. When I woke up and asked for tea, it was there almost immediately, with lemon and sugar on the side.

I love how fun Starlux is

The other thing I love about Starlux is that it doesn't take itself too seriously.

There's a space theme running through the whole airline, from the Galactic Lounge in Taipei to the COSMILE loyalty program. Since 2024, it's been working with Peanuts, so Snoopy turns up on themed flights and merch.

On my flight, the entertainment screen displayed a Snoopy welcome for me, and I still carry my things in a Starlux Snoopy tote bag.

Even the toilet paper is custom printed with a runway design. All of these things make the airline feel like it's enjoying itself.

Starlux got the three things that actually matter right: the seat, the food, and the crew. And it did it with a sense of fun that a lot of the big-name carriers have somehow lost along the way.

I've flown business class on dozens of airlines, including some of the world's most famous seats. If you're flying between the West Coast and Asia, I'd book Starlux.

Starlux did not respond to a request for comment from Business Insider.