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Orlando, USA · April 2024
Orlando Again in April
One night at the Hyatt Regency Orlando. Quick in-and-out. The Hyatt Regency is connected to the Orange County Convention Center by a skybridge, which means you never have to go outside, which in April in Orlando is a feature. The hotel is massive....
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One night at the Hyatt Regency Orlando. Quick in-and-out. The Hyatt Regency is connected to the Orange County Convention Center by a skybridge, which means you never have to go outside, which in April in Orlando is a feature. The hotel is massive. The atrium lobby goes up about eight floors with enough marble to tile a Roman bath. Everything about it is designed for volume: wide hallways, multiple elevator banks, restaurants that seat 200.
I checked in around 2 PM, dropped my bag, walked the skybridge to the convention center. The skybridge is its own experience. About a five-minute walk through a covered glass corridor that connects you directly to the convention floor. You pass over the street below and for a moment you're suspended between the hotel world and the conference world, which is about as poetic as a skybridge gets.
The conference was a different crowd than January. Smaller, more focused, fewer first-timers and more people who'd been in the industry long enough to skip the intro sessions and go straight to the advanced ones. The convention center itself is a massive building that manages to feel both impressive and soulless at the same time. Concrete floors, high ceilings, fluorescent lighting that makes everyone look slightly ill. But it works. The breakout rooms are well-organized, the Wi-Fi holds up under load (which is not a given at conferences), and the signage is clear enough that you can find your session without stopping to check your phone every 30 seconds.
I spoke on a panel in the afternoon and the room was about two-thirds full, which for a 3 PM slot on a Thursday is respectable. The other panelists were good. One of them made a point about how most people are optimizing for attention when they should be optimizing for trust, and the room got quiet the way a room gets quiet when someone says something true that nobody wants to be the first to agree with. A guy in the front row nodded so hard I thought his neck might give out. After the panel, three people came up to continue the conversation, which turned into a standing cluster near the exit that lasted 20 minutes and probably annoyed the next session's tech team trying to set up.
The evening was unhurried in a way that one-night conference trips usually aren't. Instead of rushing to the airport, I had dinner at the hotel bar with a couple of people I'd met at a different conference six months earlier. This is what happens when you do the circuit long enough: the same faces appear in different cities, at different events, and the conversations pick up where they left off without anyone acknowledging the gap. We talked about their new product launch over mediocre nachos and decent whiskey. The nachos were not the point. The relationship was. One of them had just left her corporate job to go independent, and the mix of terror and excitement on her face when she talked about it was familiar. I'd seen it in the mirror a few years ago. I told her the first six months are the hardest and then you can't imagine going back. She ordered another whiskey.
I walked around the convention center area after dinner, just to walk. April in Orlando is warmer than January but the evenings cool down enough to make it pleasant. The area around the convention center is not designed for walking. It's designed for cars. But there's a stretch along the canal near the Rosen hotels that has a path, and I walked it for about 30 minutes, listening to nothing, thinking about the panel and the conversations and whether I'd said anything useful or just filled time. That's the internal monologue after every speaking gig. You never fully know until someone emails you three months later and says "that thing you said stuck with me."
The Hyatt room was fine. Updated Hyatt standard: comfortable bed, good lighting, a desk that works. I set an alarm for 6:30 and woke up at 6:15, which is what happens when you're speaking in the morning: your body decides sleep is over before the alarm confirms it. I got a coffee from the lobby Starbucks (there is always a lobby Starbucks, at every Hyatt, in every city, and the line is always six people deep at 7 AM) and sat in the atrium for 30 minutes going over my notes. Not because I needed to rehearse, but because the ritual of reviewing calms something down. The atrium at that hour was mostly empty except for a few other speakers doing the same thing: laptops open, coffee in hand, the particular focused energy of people about to talk to a room full of strangers.
I spoke again at 9 AM to a smaller room. Morning slots are always lighter because half the attendees are still at the breakfast buffet working through their second plate of scrambled eggs. The people who show up to a 9 AM session at a conference are the people who actually care about the content, which makes them the best audience. Smaller, but leaned in. I liked the morning crowd better than the afternoon one.
Packed, checked out, and was at MCO by noon. The Uber to the airport took 20 minutes, which is about as frictionless as Orlando gets. The airport has a new terminal, Terminal C, that opened in 2022 and has more natural light and better food than the old terminals. I ate a mediocre sandwich at a gate restaurant and thought about the woman who'd just left her corporate job and ordered a second whiskey. I hope she's doing well. I think she is.
Some trips are transactions. You fly in, you deliver, you fly out. The value isn't in the destination. It's in the three people you talked to and the two ideas you brought home.
Travel Tips
Best TimeOctober to April
MoneyThe United States Dollar (USD) is the currency, and credit/debit cards are widely accepted everywhere, so you won't need to carry large amounts of cash.
LanguageEnglish is the primary language spoken, but you will hear Spanish frequently as well.
What to Pack
Lightweight rain jacketComfortable walking shoesSunscreenReusable water bottleSwimsuitBreathable clothingPortable phone chargerA hat or sunglasses
Tips We Wish We Knew
Arrive at Parks Early
Plan for Afternoon Showers
Book Dining Reservations Ahead
Take Midday Breaks
Stay Hydrated
Trip Cost Breakdown
Business class, upgraded rooms, fine dining, and private transfers.
Est. Total Per Person$900
2 Days · Per Day$450
Hotels$400
Food & Drink$300
Local Transport$200
Estimates per person based on our experience. Prices may vary by season and availability.
Day by Day
2:00 PM
StayChecked into the Hyatt Regency Orlando.
3:00 PM
DoSpoke on a panel at the conference.
7:30 PM
EatDinner and drinks at the hotel bar.
