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Where We’ve Been, Where We Are, & What’s Next

by Tony · 26 comments


The “Cliff Notes” Version

The mountains and woods of California.

Portland, Oregon.

Cincinnati, Chicago, & financial freedom.

That’s the shortest possible summary of our life to date, so let me explain just a bit more…

The Mountains And Woods Of California

The wilderness

We touched on this occasionally (but even then only briefly) over the past year, but almost by accident we spent an entire year pet sitting and property caretaking on a ranch in the Sierra Nevada mountains.

House and pet sitting questions are some of our most frequent from our readers, so we will definitely dig in more over the coming months to detail our experience. Our experience this past year in the Sierra Nevada’s was incredibly unique as we were VERY remote. In some ways, we felt more out of touch with friends/family/culture than we did when we traveled internationally for all of 2012. Why was that?


  • We lived 3 miles down a dirt road where we had to cross a river to reach the property
  • We were 50 minutes from the nearest grocery store and had to plan out an entire week’s meal plan just to make it work
  • The only ambulance that could reach us was a plane service that would land in the property’s pasture to take us to a hospital (luckily, we never had to test it out)

But that remoteness was also fun and let us…

  • Focus on work and launch our own businesses
  • Hike/run/explore the wilderness
  • Fulfill our desire to be with animals, as we had two horses, two dogs (sometimes 4), and two cats to take care of
  • Check off splitting wood from my manliness to-do list, as I had to split cords of wood in order to have enough heat for winter (Yes. You read that right. We only had wood heat for the cold winter months!)

Splitting Wood

But because of how remote we felt for most of 2013 (and some of 2014), our desires swung the other way and now we wanted the frenzy of city life…

Enter Portland

Welcome to Portland

We visited Portland, OR for 20 hours in the Fall of 2011 and even though it was pouring rain, we fell in love. Between the awesome food, great public transportation, reasonable prices, and the easy access to outdoor activities, we knew this was a city that could show us a great time.

Our obsession with food is no secret, so you really shouldn’t be surprised that we were attracted to the city’s great food scene. But what we weren’t expecting was that after a year in the woods, we would desperately be looking for the ability to walk everywhere we needed to go. That’s why after a short but exhaustive apartment search, we moved into the center of the city.


We’ve currently been in Portland for about two weeks and still don’t have our gear shipped from the East Coast yet (where it had been in storage since before we traveled in 2012). But it is on the way – and thanks to a nearby IKEA and a generous couch and mattress donation from Meg’s sister and Bro-in-law in Seattle, we aren’t working or sleeping on the floor.

But now it’s time to explore Portland! We have gotten out a bit on our own, but if you have any must-see or do recommendations, be sure to tell us in the comments at the end of the article.

What’s Next?

Just because we’ve gone back to renting a full-time apartment doesn’t mean our travels are over. One of the main reasons we are working for ourselves is so that we don’t have to ask permission for vacation. We plan to use the freedom we have to work from anywhere to take as many trips as we can.

What’s next for travel is a trip to Cincinnati, OH to experience Oktoberfest there with friends, followed by a week in Chicago, and ending back in Cincinnati for those same friends’ wedding.

What’s next for life is crushing work so that we can afford to travel more and experience more of our new city. Hopefully city life will give us a lot more time to network and make some great business contacts :)

Your Turn

So that’s where we’ve been, where we are, and what we have coming next. But what about you? We’d love to hear your short “cliff notes” synopsis so we can compare notes!

About Tony
Quit his job to try actually following his dreams for once... and is currently loving it. He is working hard to to make this life-style permanent by writing about his adventures and brainstorming money making opportunities with his partner-in-crime, Meg.

Nicole August 5, 2014 at 5:27 pm

I’m a life long Portlander. I love it here. Next summer I’m getting married to the love of my life and best friend, then we’re going to spend 3 months in El Savador learning the coffee trade (he’s inheriting acres of a coffee plantation) and traveling South America. Here we come Brazil!

Tony August 5, 2014 at 7:10 pm

Spending 3 months in El Salvador learning the coffee trade sounds incredible, Nicole! How exciting!

We never made it to Brazil in our travels, but did Peru, Chile, Bolivia, and Argentina. If you have time and like to hike, definitely make swing down through Patagonia… it’s incredible!

Thanks for sharing!


Create/Enjoy August 5, 2014 at 10:23 pm

Wow, that’s quite a story! House-sitting/caretaking is awesome in a great place, although that one sounds so remote – but wouldn’t be bad for a limited time! Amazing you fell in love with Portland after only 20 hours! Welcome!

Tony August 5, 2014 at 10:49 pm

Thanks so much! It really was a great time, but we are more than ready to experience city life for a while :)

Geoff (Steep Stories) August 6, 2014 at 4:14 am

Egad, you’re right. Chopping wood IS manly and satisfying. I haven’t done that in decades.

Tony August 6, 2014 at 4:51 pm

Nothing quite like the feeling of splitting a long with one swing. Plus I grew out a santa beard during the fall so I was in full lumberjack mode :) Thanks for sharing Geoff and I love the use of egad!


Steph (@ 20 Years Hence) August 6, 2014 at 12:47 pm

Thanks for the update, guys, and so glad to hear that life has been good to the two of you. Everyone we know who has spent time in Portland absolutely adores it, and the food scene is pretty much the first thing that they mention, so I can’t fault you on your choice! Looking forward to reading a lot more about the glorious meals you discover while there!

Tony August 6, 2014 at 4:13 pm

The first day we moved in we went to the same restaurant we ate it two years ago (The Veritable Quandary) and it was just as good as we remembered… no complaints so far!

Thanks for dropping by Steph and we’d love to hear what’s going on with you these days!


Erin August 6, 2014 at 3:49 pm

Great meeting you and Meg on Monday! Glad you guys made your way to Portland. Have fun exploring the city and hope to see you both again soon!

Tony August 6, 2014 at 4:14 pm

Thanks, Erin! We had a great time so thanks for thinking to invite us. We can’t wait to explore more of the city and we’ll definitely have to meet up again!


Stephen August 7, 2014 at 3:52 am

Sounds like you guys have the next few steps pretty well figured out. I look forward to seeing you put up from Cincinnati, I think thats a pretty neglected travel destination as far as US cities go!

Tony August 7, 2014 at 12:54 pm

Thanks, Stephen!

We’re excited about Cincinnati as my friend who lives there has always touted it as supremely underrated. Definitely not a city I would think to visit, but because of the wedding we had the opportunity so we’re going early to check out their oktoberfest :)

We’ll let you know how it goes!


Stephen August 7, 2014 at 9:43 pm

I’ve got an old buddy in Cleveland that I’ve honestly never even really considered visiting there. Perhaps you guys can change my perceptions here.

Pech August 7, 2014 at 12:30 pm

I have always lived in an urban environment- first Chicago, and then now here in Portland (I moved here about 6 years ago). At the same time though, I have also had the same desire to always be able to walk as much as I can, so I have always lived in city centers. And, just as before, I don’t own a car so rely completely on my own 2 feet, public transit, friends, and taxis as needed. Unlike in Chicago though, it’s so ridiculously easy to get to nature in Portland that I don’t feel a yearning to go so remote unless it’s just a vacation, not as a way to live my everyday life, if that makes sense?

Tony August 7, 2014 at 1:37 pm

The access to nature is one of the best parts, Pech! Great call.

We’re really excited that right within the city there are so many great parks… but we’re also excited that we’re two hours from both the ocean and the mountains. Can’t wait to explore!


Holly August 7, 2014 at 1:27 pm

It’s so great to hear another nomad ranch story! We were on an amazing farm in Northern BC for 3 months at the start of the year. We learnt so much about what it meant to be so remote and how to just make do with what’s available to you. More folk should consider bootstrapping their businesses on a ranch!

We’re also having a total love affair with Portland, and I’m super jeleous! We hit 12 cities over a 2 month roadtrip through June/ July and Portland was, hands-down, our absolute favourite. Such a beautiful, clean and welcoming city. And the food! WOW!

Tony August 7, 2014 at 1:39 pm

We definitely learned a ton about property management and how to live far away from resources you take for granted. It was really fun though! Plus it was a very cost effective way to start up a business :)

We’re really excited to be living in Portland and am so glad you like it as well. Feel free to email us or comment with some of your favorite things to do in the city as we are just starting to explore!

Thanks, Holly!


Melinda August 7, 2014 at 4:14 pm

Welcome to Portland! I have to say that I am a little jealous of your lifestyle in that you can travel whenever you want!

Tony August 7, 2014 at 4:45 pm

Thanks, Melinda! Our lifestyle is closer to traveling when we can… then whenever I want. Still moving towards the day we have full freedom :)

Thanks for dropping by!


Christine August 8, 2014 at 1:28 am

So happy y’all have found your way to Portland! It truly is an amazing place…beer, coffee, bikes…what more could you want in life?!? We have temporarily “settled” in PDX for the past year and loved every minute of it. Next on the agenda is our RTW trip! We are sad to be leaving the beautiful PNW, but excited for the next chapter. Cheers!

Tony August 8, 2014 at 2:08 pm

Thanks so much, Christine! A “temporary” stay of a year is a long time… but we did the same thing for our house sitting job so we get it :)

What an exciting next chapter… can’t wait to read all about it!


Peter Korchnak @ Where Is Your Toothbrush? August 10, 2014 at 3:19 pm

Welcome to Portland! When Lindsay and I thought about where to settle after our RTW trip we could not imagine not returning here. Summers are especially astounding in the city and the area overall.

Sorry I missed you at the bloggers picnic, I’d had a Portland kind of night and could not make it. Hope we get to meet soon.

Tony August 10, 2014 at 10:08 pm

Thanks, Peter! We are loving it in Portland so far and can’t wait to explore even more. I’m sure we will get to meet in person at one of the next events that pops up!


magz August 11, 2014 at 10:50 pm

Love your #ranchlyfe stories… but so happy to have the bro/sis back in a city that’s a little easier to visit :) woot woot Portland visits here I come!!

Tony August 11, 2014 at 11:45 pm

We’ll be ready to have you shortly… the futon is almost here!

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