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I Brought 20 Hookers to Central America on Business.

In: Confidence,

I sloshed on yet another layer of gloss, steering frantically with one hand while trying not to rear end a truck full of cows. I mean, what would I tell the Life Hooky group?

“We didn’t pick you up at the airport in San Jose because, see, there were these cowsssssss.”

Even I would think I was making it up. And the only time I make anything up is when the chicken is overcooked, because what kind of person actually calls another person out on overcooked chicken?

But that’s enough about farm animals. Stop making me talk about farm animals, okay? Did Susquehanna County put you up to this? Sometimes I feel like I’m the star of Sweet Home, Alabama, except then I remember I’m not Reese Witherspoon. And then I say fuck really loud.

Anyway, so I’m barreling down a Costa Rican highway, with one of my creatives, Jess, by my side the entire twenty-three-point-wrong-turn minutes from the hotel to the airport, unsure of what to expect. At one point we actually did that thing where we looked at one another (YES, while driving) and said,

“You realize we just brought twenty strangers to Central America, right? Strangers. Who we’ve never met before. To Central America. And we’re responsible for THEIR LIVES.”

Which is a funny thing, really, because as someone who’s never had kids, the most I’ve ever had to worry about is dropping an Apple product in the toilet. You pretty much know what kind of day you’re going to have if you punt an $800 gadget into a pool of human waste water.

So while on one level we knew exactly what we were doing—the Life Hooky event was, after all, carefully planned through every last detail—on another level, the fact that these twenty strangers had actually arrived hadn’t even sunk in yet. For months we’d been so busy going through the motions, planning the perfect gift boxes, writing the world’s funniest slang section to include in our welcome guide, Googling “sloth bite remedy,” and going over Operation: Participant Thrown In Jail, that when the moment came to enjoy the fruits of our labor, it felt more like we were going into labor.

I’ll spare you the ubiquitous birthing metaphor (surprise! starting a new company isn’t actually the same as ejecting a human out of your insides), but I will say this: For someone who’s much more “creative” than “logistical” (my favorite euphemism for ‘shit planner’), going through the motions leading up to the event was the hardest part of all. I’ve been running my companies entirely remotely online for years—usually without routine by design—and so I hadn’t gone through the motions in years. At least, not any involving clothing and sobriety.

Did we have the right ratio of beds to rooms to participants based on whether they were in a double or single and if the last letter of their first name started with A-F? What about the vegetarians? And the two brave men who surely wouldn’t want a sarong in their gift box? What if it rains? What do we donate to the school? How will we get the participants and the kids to interact? How much flour should we give the Nicaraguan woman whose empanada business we were helping to start? Why not gift her AN ENTIRE DUMPTRUCK FULL  OF FLOUR? (Answer: Because you have to get to the Nicaraguan woman’s house by panga boat. And we didn’t have a plan for Operation: Death By Panga.) And naturally other hard questions like what if someone cuts their finger off in a high-stakes game of Pinochle? Did they sign the waiver? DID EVERYBODY SIGN THE WAIVER?

In sum, I felt like I’d have an easier time organizing the Macy’s Thanksgiving Day Parade. Jess, on the other hand, who’s basically the poster child for planning, would bound into the room and announce stuff like, “THE LABELS ARE READY!” which slightly made me want to punch her while kissing her while renewing her contract until the end of eternity. Is this what Facebook meant by, “It’s complicated?”

So as we barreled down the Pan American, blaring Sean Paul at anti-human decibel levels, we knew everything we’d worked for over the past year would amount to this VIM. Very important moment.

The moment when we’d slap on our fake moustaches (naturally there were fake moustaches) and jump out of the car screaming like lunatics and greeting twenty real-life versions of online avatars. The moment we’d violently shove any last minute doubts into our dress pockets. The moment we’d ooze (ooze? gross) as much confidence as possible to make everyone else feel at ease.

The moment when Life Hooky became real.

And real it became. As I drop, tucked and rolled out of the car, jumped up on a nearby piece of cement, and declared, “WELLLLLLLCOMEEEEEEE LIFE HOOOOOKYYYYYY!” I was met with a resounding, “WOOOOOOOOOOO!” followed by applause. Followed by half the airport wishing they were us, and half wishing they could harpoon us. Followed by beers on a bus, jokes about hookers (get it? life hookers?), and five days of connecting, laughing, learning, listening and by golly dare I say it, living.

Naturally this is the part where you’re expecting me to sum it all up with one big, happy horseshit lesson about how all the planning was worth it (you can read the blog post where I made the very first announcement about Life Hooky) and “fight for your dreams!” but even if I did say boring stuff like that, it wouldn’t be the lesson I’d share. Because you already know that stuff. We all know it’s going to be worth it. We all know we should be fighting for our dreams. We all know that anything is possible.

What we don’t know is the hard stuff.

The human stuff. The stuff we all secretly wonder. Stuff like, “Will they like me?” or “What if it’s awkward?” Stuff like, “What if something goes wrong?” and “Is my best effort good enough?”

The stuff even the most confident of people wonder when they awkwardly leap onto a cement platform to welcome a group of strangers from all over the world.

But that’s the thing about stuff you don’t know:  You don’t know.

But there’s beauty in that.

Because while not knowing is messy, nerve-wracking, uncomfortable, horrifying and fucking nauseating…

…it’s also the perfect excuse to get out there and surprise yourself. 

Because there, tucked in neatly between the messy, nerve-wracking, nauseating pieces of the hard stuff, you find the easy stuff.

The stuff you were meant to be doing. The stuff that feels right. The stuff you’ll be proud to say you’re doing with your life.

It’s called your potential.

And even the best planner can’t plan for it.

Your only choice is to slap on a moustache, take a deep breath, and let not knowing be the reason you showed up at all. 

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Remember. (A Quick Read Worth, Well, Reading.)

Remember: Whatever you want to do in 2013, you can do. Whatever you think is too hard, too complicated, too overwhelming–you can figure out. Whatever things you wish you didn’t have to do anymore–you can renounce. Whatever mistakes you’ve made–you can forgive. Whatever direction you want to take–you can take. And whichever jerk off tells […]

In: Confidence,


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65 thoughts on "I Brought 20 Hookers to Central America on Business."

  1. maxwell ivey says:

    thanks, i think my super power is positivity. I decided that it could be done and th lord th universe or whatever you are comfortable with brought mitchell walker into th picture. He worked with me online to help me get the hang of th hangouts. grin He has to add and delete people from the circle i use to invite people to the hangouts but that is the only part I can’t handle myself. and if for some reason he decided to no longer assist with that task, I am sure I could find someone els who would do it for me. Mitchell not only agreed to come back next week and his friend ryan will be there too. and maybe mitchell’s sister. Need to get more activity but it takes a while to build an audience. the hangout is on youtube. if people want to participate live they need to connect with me on google plus and ask to be added to th guest list. Otherwise, they can submit a question in advance and get the answer by listening to the show after it is posted to youtube. And thanks to paul graham of the daily wail and william butler for submitting questions for last week’s hangout. I’ll add the link to this week’s show. Hope that is okay sweetie. and my favorite super heroes growing up were underdog and superman odd choices I know. thanks and take care, Max

  2. Nikki Groom says:

    Looks awesome!!!!!!!!!!!!!!!!!

  3. Jesus Tavern says:

    Reading this post on a sunny Saturday morning. Drinking coffee with organic sweet cream butter in it while my 3 kids play. Best part of the morning so far? Laughing out loud while imagining Ash drop an Apple product in the toilet! Good stuff here Ash. I also love the image of you screaming confidently from a concrete stage : ) The video was great and it made me wish me and my wife were there with you guys. When is the next big trip?

    And BTW, some of my family and friends struggle to understand why I can cus, drink, be real and be a passionate expert about Jesus at the same time. They struggle to believe me when I tell them that religion doesn’t exist. There is only love. We’re all ONE in love. Seriously. Gay, straight, black, white, Mac, Windows, whatever. We’re all ONE (extra grace for Windows users) and I’m glad you and your crew get Life. I love the Life Hooky concept.

  4. Troy Swezey says:

    Oh You! You fooled me with the title. I thought… Oh! Good on you!