Getting to Dubai — The Hard Way
Sometimes the journey is the content.
I was supposed to fly Pittsburgh → Chicago → Dubai. Simple. Direct-ish. I’d done this math before — leave Thursday afternoon, land in Dubai Friday night, get settled Saturday, tee off Sunday. Clean.
The universe had other plans. Again.
Here We Go Again
If you followed last year’s Skillest trip, you know how this goes. In 2025, United sent my clubs to Minneapolis. I played the entire Pro-Am in Dubai without my own sticks — borrowed clubs, unfamiliar feels, completely in my head before the first tee. It wrecked me mentally. I had this perfect picture in my mind of how the trip would go, and when reality didn’t match, I couldn’t adapt.
I promised myself this year would be different. Not just the logistics — the mindset. I was going to be prepared for things to go wrong. I was going to stay loose, stay positive, and handle whatever came.
I just didn’t expect the test to start at the Pittsburgh airport.
Flight 1: The Malfunction
Sitting at the gate in Pittsburgh, bags checked, clubs checked, mentally already on the plane. Alone — none of the other event golfers were flying out of PGH. Just me and my Caddy Daddy bag somewhere in the belly of the airport.
Then the announcement: maintenance issue after de-icing. Back to the gate. Delay after delay — 2pm became 4, then 4:30, then 5. The plane hadn’t even left Chicago yet.
My connection to Dubai? Gone.
The feeling was overwhelming. How could this happen two years in a row? What are the odds? I stood there at the gate watching the board flip from DELAYED to CANCELLED and my first thought was dark: Something’s going to happen to my clubs again.
I caught myself. Stay positive. This is exactly what you trained for.
Flight 2: The System Failure
The United agent was genuinely trying to help. Nice guy. He found a route through Boston — Pittsburgh to Boston, then Emirates straight to Dubai. Perfect backup.
Then the ticketing system crashed. Couldn’t issue the ticket. Just… couldn’t.
So there I am. Two plans down. Standing at the counter at Pittsburgh International with a suitcase and a set of golf clubs, watching my trip evaporate.
Flight 3: Send Me Anywhere
I said it exactly like that: “Send me anywhere in the world, as long as I get to Dubai.”
Here’s where last year’s version of me and this year’s version diverge. Last year, I would have stood in line, waited my turn, hoped someone figured it out for me. This year? I overheard an agent directing people to terminal 12 and was the first to get rebooked. I advocated for myself at every counter. I didn’t wait for solutions — I went and found them.
The agent found a British Airways flight to London Heathrow, leaving at 9pm. From London, I could catch a connection to Dubai. It would work — barely. I’d have about two and a half hours in Heathrow to collect my bags, clear security again, and make the gate.
But there was a catch. Since I was switching airlines entirely, I had to go back through the gate, physically retrieve my checked bags from United, and re-check everything with British Airways. Including my golf clubs.
I personally walked those bags from United to BA. No one was going to lose my clubs this year.
The oversized luggage guy at BA didn’t love that. “Why’d you bring this here?” he asked, looking at the Caddy Daddy bag like I’d rolled a kayak up to his counter.
I told him BA sent me. He grumbled and said he’d “talk to them about it.”
Last year, that interaction would’ve sent me spiraling. They’re going to lose my clubs. It’s happening again. This year, I texted Andy a quick update, called my wife to tell her I was rerouted but on my way, and let it go. Stay positive. Keep moving.
My Caddy Daddy travel bag. This thing went through three airlines, two continents, and an oversized luggage guy who didn’t want it. It showed up in Dubai without a scratch.
The Overnight
Seven hours to London. I slept maybe five — as much as you can sleep upright in economy.
Landed at Heathrow at 8am London time with a few hours to kill before the Dubai connection. Grabbed coffee, walked the terminal, and — I’m not making this up — I vibe coded. Sat down with my laptop and started building this website. The one you’re reading right now. Something about being stranded in an airport between continents makes you want to create things.
Oddly enough, I think the layover helped with the jet lag. My body was confused enough that it just… reset.
On the second leg, flying over Florence, I had a moment. We went there last August — my wife and kids, the whole family. Seeing it from 35,000 feet hit different. Time flies. It’s hard sometimes to appreciate things in the moment — to actually be present instead of rushing to the next thing.
Going to Dubai is a blessing. No matter how I play. No matter how many flights get cancelled. The fact that I’m doing this at all — playing golf in the desert with people from around the world — that’s not something to take for granted.
This is where the adventure really started.
The Landing
I touched down in Dubai just after 9pm Saturday — only a couple hours later than my original itinerary would have had me there. Took a cab straight to the hotel. It was 2am local time by the time I got to the room. I went straight to bed.
The bags made it. The clubs made it. I made it.
Net result? Pretty good, actually. I’m still on schedule. The trip is unaffected. And I have a story worth telling.
Year 1 vs. Year 2
Last year, I showed up in Dubai without my clubs and with a picture-perfect expectation that could never deliver. When things went wrong, I didn’t have the tools to handle it. I was reactive, frustrated, and mentally defeated before I hit a single shot.
This year? Chaos again — but different.
I was proactive. I overheard an agent and moved first. I advocated for myself at every counter. I personally walked my bags between airlines. I texted my wife and my coach, not in panic, but in update mode. I built a website in a London airport because I had the headspace to create instead of catastrophize.
I came into this trip knowing it wouldn’t be perfect. Knowing there’d be ups and downs. Knowing that the growth isn’t in the scorecard — it’s in how you handle the stuff that goes wrong.
Stronger. Better. More present.
Bring it.
Travel Tip: The Caddy Daddy
Shoutout to my Caddy Daddy travel bag. This thing survived being rerouted across three airlines, handled by at least six different baggage crews, and sat in oversized luggage purgatory in Pittsburgh. Clubs arrived in Dubai in perfect condition.
If you’re flying with clubs internationally, get a proper travel bag. It’s not optional — it’s insurance.
This is Day 0 of the Desert Grind: 7 in 7 — seven courses across Dubai and Abu Dhabi in seven days at the 2026 Skillest Pro-Am. Follow along.
Next up: Day 1 — Arabian Ranches →