The Spring Everything Went Wrong (and Why I'd Do It Again)

A security officer is standing in the Delhi airport holding my period underwear in the air for the whole world to see. A random Indian man is hovering over my shoulder, peeking into my suitcase.

“Do you MIND?” I snap at him?

Behind him, a second officer is going through my open suitcase on camera — narrating, apparently, for posterity. They've already taken my travel clothesline. They've confiscated my massage ball. They dumped out my flask for reasons no one will explain, pocketed my batteries, and are now eyeing my headlamp like it's contraband. I am filming none of this, because I am the one being filmed.

And here's the thing: this wasn't even the worst day of the trip.

This was spring 2026. Two months, four countries (India, Kenya, Egypt, and Morocco), four group trips, and a run of catastrophe so relentless it stopped being stressful and started being almost funny. Almost.

There's a name for this, and if you've traveled with me, you already know it: it’s called Type 2 Fun, and it's the whole reason my company is rebranding to Type 2 Travel™.

Type 1 Fun is fun while it's happening — the beach, the wine, the massage. It’s nice. It’s also predictable.

Type 2 Fun is miserable in the moment and legendary forever. It's the stuff you'd never sign up for and also would never trade. This spring was the most Type 2 Fun I've had in years. Let me tell you about it.

Our India crew after our second Holi celebration

The trip that broke before it began

Things started falling apart before I ever left my hometown of Eau Claire, Wisconsin. It’d been a rough 6 months, between traveling nonstop in the fall, the passing of my last remaining dog, buying and selling a house, and moving 8 years of my life with no time to unpack.

Prepping for four back-to-back groups is no easy feat, and TBH, it damn near killed me. If you want the tea on all the things, listen to my viral episode of Type 2 Travel Podcast: Under Construction.

It was a chaotic time, but I had to go. There was no calling in sick for this one. So I packed two months of travel into a couple suitcases the night before I left (as I do), put on my big girl panties, and hoped for the best. 

The morning of my departure, I sat on the plane, getting ready for takeoff. We had already been delayed for an hour, but I was still going to make my connection as long as we took off soon.

But then a guy stood up and loudly threw a tantrum about wanting to get off the plane since he was going to miss his connection.

“There is no freaking way they are letting him off the plane–we’ll all miss our connections,” I whispered to the girl next to me.

She shook her head in disbelief.

But low and behold, the flight attended got the pilot to come out of the cockpit, and they gave everyone on the plane one opportunity to get off. 

This snowballed into a whole shit-show of additional delays, as they had to update the flight manifesto and get the luggage off the plane for all eight people who got off the flight. We were delayed an additional 45 minutes because of one selfish guy who could only think of how this impacted him.

To say I was pissed is an understatement.

I ran through O’Hare upon landing but still missed my connection, and according to the customer service line I had to call, there were no flights to India until the next day. I lead group trips, and I needed to be in Delhi before my group, no exceptions.

So I went full-on Karen, found a manager, gave him my best I-travel-for-work-please-have-pity-on-me speech, and got immediately rerouted through London.

My luggage apparently did not get the memo, despite the manager ensuring he had it handled. None of it showed up in Delhi. And just to put the icing on the cake, I’d also given the gate agent in Eau Claire my carry-on bag to check at the last minute because I knew they’d be gate checking it and it would cause me extra time to wait for it on the jet bridge when we landed.

I checked into my hotel with the clothes on my back and zero backup. No laptop charger. Not even a toothbrush.

I know better.

And then — because the Universe sometimes has a cruel sense of timing — my one and only employee called me and resigned out of the blue and gave her two weeks notice. On day one. Of a two-month trip.

Talk about kicking someone when they’re already down.

I spent the next two days locked in a hotel room crying in my bed, rationing the single outfit I owned and washing what I could in the sink. When my group arrived and the welcome dinner rolled around, I walked in wearing the exact same clothes I'd landed in, smiling like a woman who absolutely had it together (I, in fact, did not have it together. I want to be very clear about that).

I've written the full, unfiltered, crying-in-a-bathrobe version of that India leg in no mud, no lotus — go there if you want the tears. But at some point the tears run out and something else takes over. 

Call it delirium. Call it professional obligation. I had groups coming and a job to do.

When the world literally caught fire

Things were going smoothly on my India group trip, aside from the chaos happening behind the scenes for me as I was prepping to lose my only employee.

A few days in, we were notified that the U.S. was bombing Iran, because…well, America. 🇺🇸

My connection to Nairobi after my India tour concluded ran through Dubai. Emirates wouldn't give me a cancellation option because they were playing chicken with their customers, so I had to either be a psychic and guess when flights would be canceled or leave it to rebooking last minute and risk not having a flight at all.

I decided to play it safe, assuming my flight would get canceled last minute with no notice (it eventually did), and I booked a new flight through Mumbai. Both of my Kenya groups had to rebook their connections too, causing me to have to rearrange airport pickups for over 20 people.

Somewhere in the middle of all that, Trump announced that Ecuador and Cuba were "next" on his list — two of my upcoming destinations, naturally.

Getting out of Mumbai was its own event. On the way to the airport, we found out Nairobi had just flooded, causing additional anxiety for my travelers reading headlines at home. At security, they pulled me aside over my water bottle and made me take one — one — sip to prove it wouldn't kill anyone. Our flight was delayed, so we waited in the lounge (which is precisely what a lounge is for) and then headed to the gate. When we got there, the gate agent yelled at us for “being late and spending too much time in the lounge” (he could see the lounge stamp on our boarding pass), even though we boarded on time. On the flight, there was no overhead space for a single bag, so rather than having people gate check their bags before boarding, the aisle turned into a luggage graveyard and we climbed over strangers' suitcases to reach our seats.

I am exaggerating about none of this. This is the part of travel nobody puts on the brochure. It's also, weirdly, the part I've come to love — because I know exactly what's on the other side of it.

Type 2 Fun, safari style

Kenya is where Type 2 fun goes to show off.

My friend Krystina and I arrived to Kenya a few days early after being in India together since the bombings had canceled her flight to Dubai. We decided to do a self care day and went in for a lash fill and walked out five and a half hours later, having gotten our nails, toes, lashes, and brows done by four deeply committed Kenyan men — one of whom then drove us home blasting Frank Sinatra’s “Fly Me to the Moon” while he drove approximately 15 miles per hour.

It was a…memorable experience.

After my first group arrived, we started the overlanding portion of our trip. Early on in the trip, our camp got raided by more than 50 baboons. We were literally surrounded by them on all sides. And baboons, my friends—they may look cute, but they are vicious.

A few days later, our overlanding truck broke down after a heavy storm in Maasai Mara, and the whole group stood in the rain singing Hakuna Matata for moral support. Eventually, a vehicle came to move us to a campsite in the middle of nowhere with no electricity, approximately one outdoor bathroom for 15 people, and a lion pride sighting nearby.

Our truck, stuck in the mud on the side of the road

“Don’t worry—there’s a guard and he has a gun,” said our local guide.

I politely declined the invitation to stay and firmly pushed for our group to be relocated somewhere with meaningfully fewer lions, electricity, and running water.

This is why I scout group trips to make sure there are no surprises like this.

One particular safari day with my second Kenya group deserves its own blog, which I will get to someday. But in short, in a single afternoon, we screamed at a bird to get it to fly for our photographer, watched a hyena eat an injured topi (I cried and am still traumatized), found a pride of female lions, got chased down by park rangers that we had to bribe for our freedom, and broke down in front of a lion sleeping under a tree. Just to top things off, I accidentally peed all over myself using my she wee because my photographer rushed me to get back in the car in fear of the nearby lions snacking on me mid-pee. 

Lions—it’s cute until your vehicle breaks down next to them

Then we spotted a leopard—my first sighting in my 3 safaris to Kenya, and the official conclusion of finally seeing the Big Five. One of our safari vehicles got stuck trying to help another safari vehicle out of the mud, all while the leopard was slinking between our vehicles. That night, a baboon stole the soap from camp, to wrap up the wildest safari day ever.

My first leopard sighting

When I finally made it out of Kenya toward Egypt, they told me at check-in that because I spent over a month in Kenya, I now needed to show a physical yellow fever card to get to Egypt (which I had but did not have on me because it wasn’t required for Kenya). So I left my bags with a random gate agent, sprinted across the entire airport parking lot, paid $20 for a brand-new card, ran back to the departures area where a long line had since formed, and bribed a guard I'd befriended earlier with a vape to skip the line. He was eying it up in my hand, and I said, it’s yours — if you get me through this line.

I have never in my life seen a man make things happen faster in my life.

If you think that sounds like a lot to pack for, you're right — the Kenyan safari packing list exists for a reason, and "clothesline the Delhi airport will likely confiscate from your carry on" is on it.

The stories you keep

Here's what two months of everything-going-wrong taught me — or re-taught me, because I clearly needed the refresher:

The best stories you own are just disasters that didn't get the last word.

Nobody comes home and tells the tale of the vacation where everything went perfectly. They tell you about the flood, the baboons, peeing your pants escaping lions, and the Kenyan men in the salon.

Type 1 fun makes a nice photo. Type 2 fun makes you someone worth sitting next to at dinner. (It's the same reason I keep telling people that the travel disasters are what actually make you who you are — and why my whole podcast episode with Tom Williams is basically a love letter to the power of discomfort.)

Maybe you're eyeing a trip and waiting for the timing to be perfect. Maybe you're telling yourself you'll go once work slows down, once you've got a buffer, once nothing could possibly go wrong.

Let me save you some time: something will always go wrong. The flight will get canceled at some point — ask my partner, Erik, who en route to visit me in Egypt, watched his get delayed and canceled four times before he waited six hours in the airport just to go back home. Another of my flights got canceled while in Egypt too. 

Shit happens, friends. And you can’t avoid it.

The flood will come. The suitcase will get raided. Your plans might get ruined.

And you will be so glad you went anyway.

That's the entire idea behind Type 2 Travel. Not that nothing goes wrong — I can't promise you that, and you wouldn't believe me if I did.

What I can promise is that when it does go sideways, you won't be handling it alone in a hotel bathrobe. You'll be handling it in a truck full of people who are about to become the ones you tell this story with for the rest of your life.

You show up. We handle the rest — even when "the rest" is a flooded road and 50 baboons.

So if you want this type of adventure with a vetted local team, a leader who has personally survived the worst-case scenario, and a group that sings in the rain instead of spiraling — come find your people. Georgia, Colombia, Egypt, and the rest are waiting for you.

Type 2 fun. It's the only kind worth writing home about.