There’s a week left until I take 40+ people jumping out of a plane in Portland. I’ve got the deposits in, head counts finalized and all the tiny little details taken care of except for one small thing.
I didn’t know how I was going to get there.
I had organized a trip from 2,000 miles away, convinced 40+ people to face their fears and jump out of a plane and collected over $2,000 in deposit money, but I still didn’t know how I was actually getting to Portland. I figured, if worse came to worse, I could just fly in to Portland thursday night, jump out of a plane on Friday, and fly back on Sunday evening. But, for something called the World Domination Summit that seemed like a pretty weak plan, so I decided to scrap that idea in favor of a better one.
ROAD TRIP
I’m a fan of road trips (you might remember this one and this one). I’ve been to a good number of countries and most of the eastern United States, but when it came to the western half of this country, I’ve done a terrible job of seeing things. I’ve been to LA, Phoenix & San Francisco as well as the Denver airport a dozen times, but as far as getting out and seeing the country, I’ve done a absolutely terrible job of seeing what the west has to offer.
So, to remedy that, I’m driving 5,000+ miles roundtrip out to Portland and back.
I had this idea way back in November, but wasn’t quite sure if I was going to be able to pull it off due to multiple variables. But, in the last week or so thanks to a few things (I quit my job, we needed more cars for skydiving, and this random guy walking through missouri needed a ride), things actually started to fall together. So while, I could just take the easy route and plunk down a few hundred bucks for a plane ticket and fly out to Portland, I realized it’s not often that a get a few weeks of uninterrupted time to do whatever the heck I feel like, so i figured I’d might take the time I have right now between jobs to see the rest of the country.
The Road Trip Minions
Road trips are awesome. I’m a big fan, but driving by yourself is usually boring. And while I pride myself on the fact that I can entertain myself for hours by singing and telling myself jokes that only I think are funny, 5,000 miles solo could be rough. Fortunately, one of my good buddies Nate, is walking across america right now. He started in Delaware 3 months ago and is headed towards San Francisco. He’s currently somewhere in Missouri. He had no clue how he was getting to Portland either, so when I mentioned the trip, he was all for it.
We’ll also be taking my little brother along. When he found out I was taking people skydiving and going on a bungee jumping adventure, he got absolutely giddy. When he found out I was driving out, he about lost it begging me to come along. Being the nice older brother I am and considering he’s actually much bigger than me now, I figured it was best to let him come along.
The Plan Is There Is No Plan
On trips like these, I like to have as little planning as possible. I firmly believe that spontaneous road trips are the best ones. If you asked me for my itinerary for the trip, I literally couldn’t tell you.
What I do know is that we’re leaving this Monday, May 30th and I need to be in Portland June 2nd by midnight at the latest. On June 3rd (weather permitting) Me + 40 people will all jump to our certain death from 13,000 feet. Pending our survival, I need to be back in the Chicago area by June 12th to drop my brother off. If I’m not back by June 12th, I need to get my brother to an airport by June 12th and Nate and I can continue sightseeing around the country indefinitely :).
Along the way, there’s a lot of places I want to see. We’ll try to map out a route to see them all in a semi-sensical manner, but there’s no telling what we’ll do once we actually end up in the car. We might like some places more than we thought we would, so we’ll be playing it by ear and doing our best to spend our time in the places we enjoy the most.
A short list of some of the places we want to see
- Denver & Boulder
- Las Vegas
- Lake Tahoe
- Yellowstone
- Grand Tetons
- 13,000 feet
- Seattle
- Idaho
- Portland
- Mount Rushmore
- Cool looking desert places [You know the ones I’m talking about, they’re in every single western film you’ve ever seen. I’m pretty sure this is in Utah/Arizona area. We’ll probably just drive around until we find it].
Like I said, the details are still being hammered out. We really don’t have a route other than “head west” and we’ll probably do a fair amount of car-sleeping and/or sleeping out under the stars. If you’re near any of these places and want to say hi, let me know where you’re at and we’ll see if we can’t meet up at some point. That’s the great part about spontaneity, nothing is planned, so if you have any suggestions, let ‘em fly. We might just be dumb enough to do it.
What’s Next?
I’ve been getting a lot of questions, since I quit my job about what’s next. I can assure you of a few things;
- I haven’t sold all my stuff.
- I’m not changing my name to Tim Ferris.
- I’m not moving to Thailand.
But I am moving. To Milwaukee. As in Milwaukee, Wisconsin. Yes, Wisconsin. The state who’s pride and joy is cheese.
Why?
I have no clue. I have no affinity for cheese and whether or not they won the Super Bowl last year, the Green Bay Packers might be the worst team ever to play the game of football #GoBears.
In Milwaukee, I’ll be working for a internet advertising agency and business incubator just outside the city. In a way it’s very similar to the work I’ve been doing, but it will also have a lot of new challenges (like learning to deal with Packer fans). More importantly, there’s a ton of really smart people that I’ll be working with who I think will make me a better marketer and entrepreneur. I think there’s a lot of value in working on your own business, but there’s also a lot to be learned from working with others and I don’t think the two are mutually exclusive, and I think there’s a lot of opportunity to do some big things down the road.
But that’s not for a couple weeks yet. In the meantime, there’s a lot of empty road in front of me [literally], and a big fall from the sky that I need to take care of first. If you’re out west and think we might run into you, give me a shout. I’d love to see if we can meet up!
[Photo 1, Photo 2]
🙂
I took the flight that was offered to me because, uh, I ran out of money and fell in love. So I’m parked in Atlanta for a bit.
Congrats, on the decision! Lake Tahoe is GORGEOUS. Make sure you go to Eagle Falls and see Emerald Island.
I did a major road trip through California and Nevada in 2005, and from NE OK to Utah in 2007, and many trips to AZ/NM from Oklahoma in my childhood. Definitely worth it!
Thanks for the suggestions. We’ll do our best to check ’em out. Should be fun!
I love road trips. I think it’s time I plan one. I grew up in Denver. If you haven’t been you will love it. If you have time you should hit up the mountains. They are absolutely breath taking in the summer. Also, check out boulder. It’s a green friendly awesome granola town with lots of character. Just a few ideas. Hit me up if you need more suggestions. Have a blast. I am super jealous.
You should definitely try to plan time for one. Find a good couple weeks, get a friend and just go :).
I’ve only known about your blog for a few months but I love what it’s all about. I just saw your tweet about Skydiving in Portland, the place I want to move to, & clicked on the link to see that you’re moving to Milwaukee… the place I currently live. I normally never leave comments but I thought this was weird enough to share. If you want any tips or info about Milwaukee, feel free to send me an email. Have fun on the rest of your trip!
Awesome. Thanks Megan! I’ll be moving all my stuff up there sometime after the road trip. Maybe we’ll get in touch. If you have any tips for me, feel free to share!
Glad to hear you are thinking of making it to Seattle. I live just north of the city, so hit me up if you and Nate come up here. If I lived alone, I’d other the couch, but I’d half to ask the other half, haha. I can show you around to the sights and mainly the best food spots. Lots to see around the city depending on what you’re interested in.
As for the cross country trek, I’ve made the drive from Michigan to Denver and Michigan to Seattle, both with one other person and they were a blast. We stopped at Yellowstone on the way to Seattle and it was beautiful. Good luck finding “the big desert”.
See you at WDS.
Definitely see you at WDS Caleb! We’ll let you know when we hit up Seattle and hopefully we can connect there as well!
For that “big desert” stuff, try to swing through Kanab, Utah, which is conveniently situated near the north rim of the Grand Canyon. Kanab was once known as “Little Hollywood” (so they claim), because nearly “every single western film you’ve ever seen” was shot in the vicinity of Kanab. Monument Valley is nearby, which is where all those big rocks and mesas you expect to see in “cool desert places” are to be found.
You’ll have a blast. I love road trips. Gonna be a while before I can do another one, but it’s in the planning stages… and it’s gonna be a good one!
I’ll be looking forward to your updates from the road!
You always have a few great recommendations in mind for every place I visit, don’t you David? How do you do it? 🙂
Welcome to Milwaukee!!!! 🙂
You will prolly see me runnin the lakefront once my feet heal! Check out Red Rock Canyon…. Absolutely beautiful….
Maybe I’ll see you there! I’ll need to find a training group. 🙂
Well, you know (or should :squint: know) my affinity for road trips, so I am more than behind you on this one.
In regards to the areas you will be visiting, add Sedona AZ onto that list if you want those “epic western backgrounds” and such. For the Grand Canyon, the south rim is the easiest to get to, the north rim (from what I hear) is much prettier. Also, on the south rim, they have a glass bottom walkway that is suspended over the canyon, so you are actually a few hundred feet above the ground, looking straight down through glass under your feet.
As far as the Grand Tetons, if you exit south out of Yellowstone, you will get dumped into the Tetons. Get there in the afternoon, find a harbor and just park yourself there, watch the sunset. Truly magnificent. Also, hit Jackson Hole after that, great little town.
If you are up in Tahoe, 2 recommendations, wine tasting just to the west in El Dorado County, amazing CA wine. Otherwise, head south to Yosemite, see (hell, go climb) Halfdome and El Capitan. Camp in the valley, its amazing.
You want any other recommendations in CA/AZ/NV, let me know. If I had a way, i would offer you a free night at my house just outside of the grand canyon in AZ, but alas, maybe next time!
I think the Tetons are definitely going to take a day or two by themselves. Sounds awesome. I’m getting excited. Thanks for the recommendations Justin!
Enjoy God’s Country (Idaho). You have been warned though…you may not leave Teton National Forest if you get out and look around for very long. A team of my high school buddies are running a 12 man relay from Logan, UT to Jackson Hole in August. The scenery and fresh air is spectacular. Good luck on the trip and the leap!
Is Idaho as good as you say? The only contact I’ve had with the state has been with numerous potatoes they seem unable to eat, so they send to the rest of us :).
Joel – take care of my boy. Hope you got Nate’s care package ok – he needs his sneakers and jeans 🙂 Oh by the way – he’s probably too humble to tell you, but his mother isn’t – June 6 is Nate’s 23rd birthday – I hope you help him celebrate in an appropriate fashion! Maybe you can put a shout-out on his facebook for me – donations to his paypal account would be an awesome birthday gift!
Have an incredible trip – give Chris Guillebeau a big hug for me.
Will do. We got the postcards. I think Alan will think it’s very funny :). And don’t worry, we’ll take care of birthday celebrations in full!
It’s amazing how many people out there share my love of adventure. Nice blog dude, you definitely have a new fan. Also I’m leaving soon on a walk of my own. Can’t wait. Excited and a little scared all truth be told but I can’t wait!
Thanks Michael. Glad you enjoy it! If you’re gonna do your own walk, definitely get in touch with Nate. He’s pretty legit. Keep me posted on your adventure!
3 dudes in a car, good luck Joel!
And with the skydive too, is your little bro joining in on that?
That’s why he’s coming out 🙂
That’s awesome, Joel! Have a great trip!
Thanks Anum!
Joel this is terriffic!
I think it’s great that you’re pushing yourself to such awesome feats, but also that you’re not doing it to fit into the whole lifestyle design dogma.
Too many people are getting it into their heads that they need to drop all their possessions, build a muse, and travel the world because that’s what others are doing.
Your goal really seems to be happy, not to be someone else or emulate whats made others happy.
You are a superhero named Joel Runyon, not Batman, Tim Ferriss or anyone else, but your own person.
Truly awesome man!
-Armi
Thanks man, that really means a lot :). That’s what I’m trying to do.
What, no Wall Drug Store? No Corn Palace? (Both are in South Dakota.) I passed out in the ladies room at Wall Drug Store when I was 18, have no desire to ever go back.
But if you’re traveling along I-90 in Wyoming and have a chance to take a short trip off the interstate to see Devil’s Tower, it’s worth the detour. Hard to believe it’s real. And I saw a flock of wild turkeys on the way, that was cool.
I’ve driven all the way across the country I think five times, and 2/3 of the way another five or six. I love road trips, it’s amazing to see what’s out there and how beautiful parts of this country are. There’s a lot of random art in fields off I-90, like the giant sculpture of a man walking a dinosaur on a leash (I think that was in South Dakota as well).
Milwaukee seems to be the up and coming Midwestern place to be!
Yes it does! We took a detour off 90 but are headed back up there and gonna ride it all the way into Portland. It’s been a lot of fun!
Congrats on the new job Tim…i mean Joel.
JSJ
Thanks James!
-Tim 🙂