Adventure Tax

(Englishman’s Bay, Tobago where I rested after my first Naked and Afraid Challenge)

I just finished filming my first Naked and Afraid Challenge where I ate burnt grubs so, 'm not above eating questionable street food in a third-world country. I love it, and when you're stuck at an airport all day it's better than overpriced foreign imitations of Pita Pit and KFC. I never understood people who go to foreign countries only to eat and drink the staples of America.


Welcome to India!

I'll have a bud light, please.

Really, bro?


A few hours north of where my plane was meant to land, Hurricane Ian hits Florida like milk and time hits shredded mini wheats. Drenched, destroyed, gross.

Three weeks ago I touched down in this very spot for the adventure of a lifetime. I was greeted, fed, driven around like a rockstar, and put up in a cute hotel so I could be filmed doing what I love for TV. Today I've been ghosted by ticket agents, left with heavy bags, and now sit on a dirty sidewalk eating doubles (the go-to street food of Trinidad and Tobago, pictured below) with flies and litter as my company. I've been wearing these pants for two days cause that's how long the flight delay has been. So far.

As miserable as it sounds, I'm OK with it. I'm from an idyllic town in Hawaii and have seen a good chunk of the world so I know even the most beautiful places have grime.

I know even the best adventures have downsides and inevitable hiccups. I call it adventure tax. It's par for the course and I've had worse.

The hours tick by in this tiny international airport. I play dress-up with career pivots as the 2-day flight delay at the end of a two-month tour beats me down minute by minute. I pretend I'm a writer, a speaker, a TV personality, a YouTuber, a filmmaker, a wilderness guide, and a millionaire who doesn't need to work or worry about flight delays. I pretend I'm home. I pretend the wifi here doesn't cut out every 5 minutes. I pretend I'm not concerned by the smell of my clothes. I pretend I'm not stuck here alone and tired.


But reality is persistent and I'm reminded that what I truly am is a hungry foreigner wondering how soon it's appropriate to get a drink and whether or not I'll be stuck here another night. I take a deep breath, then another. The flight is delayed another three hours. I guess after 43 hours and a barrage of urgent cab rides and hotel bookings, what's another three? Here I am.


Here. First Tobago, now Trinidad. The home of the steel pan and calypso music. It's at the end of the Caribbean and the beginning of my long journey home.

It's been months on the road, yet these two extra days make my heart shrivel. If all goes well I'll be in Miami by midnight, and Boston by 3 pm tomorrow, making me three days late in total. But when things aren't going well they tend not to continue not going well so I hydrate, eat another double, and prepare myself for another day of delay. At least these doubles have tamarind sauce. Gosh darn, I love street food.


I signed up for this. I signed up for this tour last winter when contracts came in. I signed up for a life on the road a decade ago when I started touring my one-person show. I get to travel the world for only the cost of performing my best jokes and tricks and dealing with so much jet lag that I've become a time traveler. I signed up for this when I said yes to the challenge of a lifetime that brought me here.

I wouldn't trade any of it for the world, but I might trade it for a flight that’s on time.

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The Biggest Lil’ Adventure