Adventure Roulette

“And where are you traveling to today, sir?”

“I have no idea.”

*polite laugh*

“Well, let me see your itinerary.”

“I don’t have one. I’m trying something different today. I’d like to go somewhere. I have $500, and I’d like you to book me a ticket.”

“Well, where do you want to go?”

“No place in particular . Whatever sounds good to you would be great!”

“Well,” (getting a little flustered now) “I don’t know what you want to do, so how am I supposed to pick a destination?”

“Literally wherever you pick will be fine. I’m sure of it.”

“Do you want to go to the city? Do you want to go sightseeing? Or what?”

“Whatever you want.”

“What if you hate it?”

“I promise I won’t. I’m sure I’ll have a great experience.”

“Is this a test?”

“Ha! No, this isn’t a test. And, if it was, I’m not sure I’d be allowed to tell you. I just got myself some free time for today, and I want to go on an adventure.”

“Okay then….”

*5 minutes later*

“Well, there you go. That’s $462. Have a good trip, and have a good meal out there. You’re at H10.”

“Thanks, Tammy!”

Introducing Adventure Roulette

For a while, one of the things on my list has been “go to the airport, and buy a ticket without knowing where I’m going.”

Your impossible list should be constantly growing. If your list is static, then it’s just another boring bucket list that you make one time, get excited about, and then never do anything with it. For the past two weeks, I’ve been feverishly knocking some of these things off my list. Hanging out with wolves, flying a jetpack, and pretending I’m Iron Man. So, when it came to this item, I realized there was literally nothing in my way of making it happen. Like most things, I just needed to do it.

So I did.

Adventure Roulette

I didn’t really know how to approach this. I know a lot of people who’ve said that they’ve wanted to do it, but I didn’t know anyone who actually had.

So, like most things, I made it up as I went along, and sort of made a game out of it. I named it ”adventure roulette” (you never know what you’re going to get), and made up rules to go along with it as I woke up early, and set off to the airport at 4am.

Here were my rules (feel free to make your own). I thought they created a decent framework for what I wanted to do.


Adventure Roulette Criteria

  • Any ticket under $500
  • Any destination at least 500 miles away
  • One backpack
  • No input at all from me on the final destination
  • No looking at the ticket until I’m through security (and, ideally, as long as possible)
  • Departure: any time during the day that I show up
  • Return: any time before midnight the following night

Like I said, feel free to come up with your own criteria, but mine gave the agent at least *some* sort of a framework to use to book a ticket without collapsing in a ball of stress because of some oddball request at 4:30am on a Tuesday.

I also realized (and accepted) full and well that I could end up in some field in Idaho, and I was just as prepared to walk around a city all day as I was to hang out in a small little town bar, and make friends with some Idaho ranchers. Everything was fair game.

I made it through security, and to my gate without looking at my ticket. I had about an hour to kill, and when people finally started sitting down around me, I took a look at my ticket.


“Way better than Idaho.” I told myself.

The next 48 hours were unscripted and unusually relaxing. I met up with Maneesh, Shannon, and a few other friends around the city. Mostly, I took my cue from Nate, and spent a lot of time exploring the city on foot (thanks, JP, for taking me on a mini tour), and spent a glorious amount of time sitting in parks, hanging out along the harbor, and watching the sun go down across the Charles River.

When the time came to book a hotel, I booked one last minute on my phone, walked straight there, and my room was ready.


I could have done a lot of crazier things, but, given that the whole trip was taken on a whim, I figured that my time on the ground might as well be too. And I had a great time.

How To Do This Yourself

I had a bunch of people tweet things at me along the lines of “that’s so awesome,” or “I’ve always wanted to do that,” when they found out what I was doing. And the good news is that you can! Here’s how (prepare for underwhelmingly easy directions):

  1. Put away $500.
  2. Go to the airport.
  3. Find an awesome agent. You can tell that some are stressed, and that some are friendly. Talk to the friendly ones if you can – they’re much more fun.
  4. Give them your $500, and tell them, “I’d like you to book me a trip somewhere – anywhere -, preferably a cool place, but it can be anywhere you like for under $500. Can you do that for me?”

It’s really that easy.

The cool thing about this one thing is that I know a surprising amount of people who want to do this. And, while it’s not very hard to do at all in practice, most people won’t simply because of the “unknown” factors involved in booking a last minute trip to somewhere where they may or may not know anyone. Go anyways.

The risk value in this is practically zero. The worst case scenario is that you end up spending more on a hotel and a couple of cab fares than you would like, and that is it. The upside is a whole new adventure that you would have otherwise missed out on.

A few people expressed worry that the TSA or gate agents would give me a hard time if I didn’t have a predetermined destination, but I had absolutely NO issues whatsoever (I only finally found out my destination when I was actually at the boarding gate).

It’s easy to do – all you have to do is go.


Additional travel tips

  1. Show up early, ideally as soon as the ticket desks open. This way, you won’t be *that guy* at the airport holding up a line of 50 people patiently waiting to check in their luggage.
  2. Travel light. Bring as little as possible – ideally just a backpack. This makes it easier to pick any flight, AND it makes your trip that much more fun.
  3. Have fun.

A little adventure every now and then is good for you. If this is something you’ve been wanting to do, and haven’t done yet, just go. There’s nobody stopping you from doing it other than yourself.

And, if you do, hashtag it #adventureroulette, and let me know. I’d love to hear your story of how it goes.

P.S. Thanks to Tammy at AA O’Hare for putting up with a ridiculous request, and booking me a great trip.


  1. says

    Ha sounds exciting.

    Saving up £500 would take a me very long time, given my current jobless student status, but I have a young persons’ rail card. (They give you cheap train travel in the UK) and this post has inspired me.

    I have been thinking what adventure can I do with my friend, although she got a promotion recently she is unhappy at work. We cycle together and have been thinking about our next trip. I am going to save us £50. Get a map of the UK and just ride to where my finger lands.

    It may not be as exciting as Boston but it will be interesting.

    Thanks for a great story, it looks like you had a great time

    • Steve says

      Hey, I used to be a pilot flying freight in North America. Every once in a while we would be lucky and have a ten hour time to spend somewhere (and I mean nowhere when I say somewhere…) one time I was in Mississippi and a casino came to pick me up and drive me 20 minutes to the casino and promised to drive me home. I won $400 dollars that night being extra lucky at the roulette wheel. Four times as much as I made flying as a co-pilot that night. I walked the streets of Oklahoma City one night trying to get dinner and saw my first real cowboys hanging out at the diner. And a hundred more stories like this, the nice thing was that I was getting paid to be there, but besides that I just let the moments happen. I once volunteered to take some supplies down to Homestead Florida after the hurricane in the early 90′s. I had 20 hours before my plane was going back home so I asked how I could be helpful. Next thing I know I am in the middle of an intersection of 4 lanes crossing 6 lanes of traffic with just me in the middle to direct, and no directions how to do it. People where slowing down and honking horns with BIG THUMBS UP and thanking me and blessing me from there car as they drove by. Handing me cola’s and bottles of water all day. They didn’t know me, or that I had just flown in on a freight plane from 1000 miles away they just appreciated that some stranger was there trying to help guide an intersection with not even a light pole, let alone a traffic signal. Later that day I was taken to eat at a Cuban diner and fed in gratis. No one at the restaurant in Miami spoke English, but they fed me.

      On the way back to home that night, I crossed paths with Bill and Hillary Clinton and was in the same room with him at the airport and 20 other people and got to watch Arsineo Hall talk show host make fun of him on TV, so I was watching Bill Clinton get punked by Arineo Hall while I was watching Bill Clinton take the put down with graciousness and a smile (Hillary was more or less scowling) Got to shake Bill Clinton’s hand and got an autograph before he was President.

      It is a little different than what Joel is saying but you don’t have to go anywhere far to do this. If you live in the city, go 50 miles by car or train or hitch a ride out to the country, if you live in the country, go 50 miles by car or train or hitch a ride out to the nearest big city and let the day unfold.

      One huge hint. When you go somewhere. Look up on Google “(city or zip code)” where you are and the Month with a three letter abbreviation and the numeric day and see what events are happening that day. Be open to it and go. Example Google: “chippawa falls wi Sept. 21″… looks like there is going to be an Oktoberfest there… Go and drink with the Germans, listen to an Ooom-pah band and get into it while you are eating German Potato Salad and getting to know some people with Dirndls and Leiderhosen on (you say I have no idea what you are talking about” ask someone, they would be glad to tell you)… you get the idea. Church or community festivals are always going on, try to get to one and make friends with some of the local vendors (not a carnie) and tell them you are just visiting for the day, do they know anyone who could show you around. You will make friends so fast you won’t believe it. Trust me, I have done it dozens of times. It has always worked out well. IF you have any apprehension, think about if some stranger came to you while you were at a local festival and asked that same question would you be a pain in the ass and make fun of them or would you practically be tripping over yourself to help them… if you are reading this blog then I think you are the helpful kind of person.

      Go do it. If you have the money by all means do what Joel is suggesting, if you don’t then do what you can afford.

      Great Advice Joel!

      “Travel is fatal to prejudice, bigotry, and narrow-mindedness, and many of our people need it sorely on these accounts. Broad, wholesome, charitable views of men and things cannot be acquired by vegetating in one little corner of the earth all one’s lifetime.” ― Mark Twain

  2. says

    This reminds me of the movie “Yes Man” with Jim Carrey where he has to say yes to everything no matter how ridiculous it is. Fun, fun! GO you!

  3. says

    Great post… the only way to make it better is to up the amount to $1,500 and make it for one week with the destination being anyway outside the US.

    It’s on my list now. I’d write more but there is a cold shower waiting for me since I stupidly signed up to run the Marine Corps Marathon without training at all for it this summer :)

  4. says

    That. Is. Awesome.

    I’m definitely writing this in my Evernote. Hate to say I’ll do this “soon,” which is vague, but I’m never forgetting this idea.

  5. says

    I have a little less expensive spin on this adventure. While standing in line for a taxi in Las Vegas, we decided to have a little adventure. We simply asked the people ahead of us where they were going and if we could share the cab. We always went where they were going (as long as it was a public place) and had a great time seeing things we would not otherwise have explored

  6. says

    I wish I had good ideas like this, haha. But I’m definitely stealing this. Might try it sooner rather than later, let’s see how things turn out. I might edit it a tiny bit though.

  7. Joe P says

    Well well well. Whats new is Old.

    When I turned 30 I did something very similar. (That was 22 years ago BTW)

    I went to Italy. No notice except One day that I was going somewhere in Europe, no reservations for hotels or anyhing. the destination was picked out of a hat by my so called buddies at a party and at the time all I was given was 1000 dollars, no cards, and the RT airfare. 5 days in country, awesome time and memories that still chill and thrill at the same time.

    So Joel, next time step it up and go INTERNATIONAL last minute. There are tons of countries that do not require a visa and its WAY more “uncomfortable and exciting at the same time”

    • says

      International was on the list. I told her ANYWHERE she wanted to book me. That’s the thing – I didn’t have any control of where she sent me. Could possibly have increased the $ amount to start – but I’ve been multiple international locations for less than $500 too. I didn’t really have any control over where I was going – that’s the purpose of adventure roulette :)

      • says

        You must have had SOME degree of boundary. Nobody wants to spend a few days in the middle of a civil war, or worse, Stoke on Trent. :-)

        I keep thinking about taking a quick coach trip to Paris to break my whole ‘travelling alone’ duck, but I keep putting it off. It will be done though..

  8. Richard Stubing says

    Wow, I have been following for several months now and I just realized that you live in Chicago! Any tips for college students to make a dent in impossible lists?

  9. says

    Ha! This is great, it’s pretty much exactly how I travel. I hate itineraries and plans, I usually don’t know where I’m going until a day or so before I go.

    This is a great idea, and although it probably scares a lot of people, trust me, it’s the most fun you’ll ever have on a holiday.

    But you have to be open-minded.

    If you’re reading this blog I’m sure you are, but whether you end up in Des Moines, Iowa or Azerbaijan, you can have just as much fun exploring a place you’ve never been before. It took me a long time to realize this, but I absolutely love it now.

  10. Mimi S. says

    Yes, I’ve always wanted to do this. Yes, I will do this. Yes, I will tweet it @ #adventureroulette by the end of this year. Feel free to hold me to it.

  11. says

    Way to go Joel! Thanks for the framework to build upon. I’m definitely adding this to my impossible list. I’m thinking about modifying this and taking a train. A little less expensive and who knows I may end up somewhere new.

  12. says

    Awesome idea, I’m definately going to try it when I get a bit of time (I’ve already got my own list I’m working through).

    I remember years ago here in Australia you could buy cheap mystery flight tickets, I haven’t seen them advertised for a long time though.

  13. Angeline says

    Wow, outstanding! it must have been fun. i cant try it, i need to feel safe and there are not many places to fly to in Zim.

  14. says


    This is awesome! This is something that I have been talking about doing for a bit now, but have yet to shut my mouth and just do it. But reading about your experience has motivated me to make this happen at the beginning of next year, and I am scheduling the time now to do so.

    Being creative like this, by making events in our lives that have unique meanings that force us to grow, are the experiences that make life amazing. The fact that you challenge yourself with the different experiences, and you share them with us on your ImpossibleHQ is a definite motivator and idea generator.

    Thanks for inspiring and teaching through example Joel! Keep up the great work!

  15. says

    Very inspiring. I recently had an adventure getting back home from San Fran last minute. I like the idea of unpredictable travel every once in a while. I can only imagine the befuddled look on the agent’s face! Well done.

  16. says

    This sounds like an amazing idea! The uncertainties spell fun and scary at the same time. Sometimes I just worry too much! One day, when I am in my very random self and when I pluck up the courage, I will try this way of travelling!

  17. Vane says

    yeah! so cool!! right now i can say…im so ready to do that ! im alone, no family , no babies… perfect time. now or never hehehehe thx for sharing ;)


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