I sold my House and moved to Hawaii, here’s what we are doing now


With three weeks left in our visit back to the mainland this past summer, we decided to sell our house in Portland, OR. This was not our plan, because if you plan ahead, you do not simply prepare a house for sale, finish 20 house projects, sell the rest of your belongings, pack and jump on a plane to Hawaii in two and a half weeks. That is insane, and that’s exactly what we ended up doing.

Summer in the Northwest

This past summer my wife, five kids and I flew back to the Northwest to spend the summer with our families and friends. 3 1/2 months! Looking back, the trip back was a bit too long. We saved a little over 1k on airfare by flying out right before summer started and flying back right after it ended. But it was too long to be away from our friends and community out in Hawaii, not to mention the surfing withdrawls we went through.

With two and a half weeks remaining in our visit, we were still looking for friends to rent out the two portions of our house. This was mildly enormously stressful, so I promptly reevaluated if this source of stress was worth it. We had a house that we had essentially turned into a duplex in the hottest real estate market in the country. Houses were typically getting multiple offers, often times for cash and usually significantly over asking price. Our long term plan had been to rent it out and use occasionally for our visits back to the Northwest. At the same time, we wanted to buy or build a house out in Hawaii. Also, the distance between Portland Oregon and the Big Island is 2,600 miles, not the easiest setup for managing a house and two sets of tenants.

After sleeping on it and talking with my wife, we decided to sell. This set off the the craziest two and a half week period you could possibly imagine.

Prepping the house for sale

I made the decision to sell the house the only way one could; without properly considering the sheer amount of work that needed to be done prior to sale lest I be overcome by anxiety. I needed to replace a 6 ft window in the garage, clean up and landscape the yard, paint the house, install closet doors, install 1k sq ft of flooring, several interior paint projects, and numerous odds and ends. Fortunately I had my boys, my super wife, my older brother, my sister and brother in law, parents and a few close friends to help me out. As an example, my 10 year old (now 11) literally hand painted the entire house over the period of a week or so. We started with the biggest projects and just kept checking them off until they were all done, often working until late into the night.

Making time for family

At the beginning of the summer, we had planned a trip to the Oregon Coast with my parents and my sister and her family. This trip landed in the middle of our last two and a half weeks. As untimely as it was in light of all our projects, it was good to get away for a few days and rest and see family we wouldn’t see for another year. Plus, the Oregon Coast has long been one of my favorite places, especially in the summer. It’s incredibly beautiful.

Beer and Pizza

Our house was set to go on the market the day after we flew back to Hawaii, but it never made it. Five days before we were to get on a plane, a very good friend of mine texted me at 10:30 at night asking me if I could get together to talk about something important. Thirty minutes later at our neighborhood Old Chicago, he explained that he and his family would like to buy our house for our full asking price. So in 2016, we shook hands on the sale of our house over beer and pizza. In the moment it felt like we were back in the 1800’s discussing how the property went from the big oak tree to the edge of the creek.  It was incredible!

Out of Debt

A few years ago we hit a major milestone after we dug ourselves out of 25k in credit card debt and became debt free. Well, except for our house. As of a few days ago, after two months of waiting for appraisals to get finished, the paperwork is done and our mortgage has been paid off! We are completely out of debt and are now looking for a house out here in Hawaii. Though it might not be as nice as our house in Portland was, our next purchase will be to own the house outright. I believe that once you’ve been set free from your debts, especially mortgage debts, you should remain out of debt if you have the means to do so.

Back in Hawaii

We have now been back on the Big Island of Hawaii for two months, and it feels great to be home. We are actively looking for a home to buy, or possibly build, if we have the patience ? We are still buying and selling on Craigslist, with a partner back in Oregon, as well as here in Hawaii. Our whole family goes down to the ocean and swims and surfs to end almost every day at one of the most beautiful places in the world.

I’ve started using Instagram a lot more so that’s a great place to follow along (and connect) on all our crazy adventures. Click here to follow me on Instagram

I’m also going to start posting video’s to YouTube. You can check out my Youtube Channel at https://www.youtube.com/RyanFinlay

Curious, would you rather read a blog post or watch a vlog, which is basically a video blog post?

Shout out to my friend Jordan for the encouragment to get this post out. More to come, and I hope you are all doing well and surving our current presidential election ?


  1. Hello Ryan, and what a treat to hear of your most recent adventure. Just last night I was talking about this very thing with one of my adult sons. Your post is timely. And, it’s especially fun to hear your side of the story!!

    Most importantly, it is great to hear how your family works hard to remain debt free. You live in such a way that seems impossible to many, but proving it is, indeed, very possible. Keep your posts coming. I’m more of a “”blog” reader than a Vlog, but, who knows? People can change 🙂

    • Hi Sandy! Yeah, I will never forget those years we were deep in debt. I definitely had a rock bottom moment that time I could no longer afford to make the minimum payments to service all our debt. I think more people need to experience that, because it’s often in those moments that we own the issues that got us into the situation, and resolve to change. Fortunately for me, at that moment of rock bottom when I was going to throw in the towel and walk away from all those debts, I had a friend named Jeremy Bowen take me out to cofee and spit fire at me to keep fighting and not give up. He challenged me hard that day!

      I will probably start adding more video over time as there is definitely a trend of people wanting to watch more video than reading, but I won’t stop writing regular blog posts. Thanks for your comment and hope you guys are well!

  2. this is such an inspiring story. I am so impressed and even though I don’t know you I am proud of such an accomplishment. you are a true Hustler and inspiration.. I read the Wealthy Barber at 16 and started to save slowly for the last ten yrs been living along with my wifes teacher salary of investments and entrepreneurial ingenuity. I may not be super rich, yet am my own boss, work from home, raise my twin two year olds. I love the hustle just added you on Twitter. Adrien

    • Thanks Adrien, sounds like you are on the right path! Congrats on the twins, kids are the best and you will enjoy teaching them all that you have been learning along the way!

  3. Hey Ryan,

    Your blog was one of the very first ones that I read when I decided to take reselling more serious and to try and make it a full time thing. Still working to get there today as well as to get debt free. I check in on your blog periodically just to see what you are up to. It’s good to see that you are doing well and living your dream. That encourages me and pushes me to keep going because it shows me that it is truly possible. Your story and blogs have always been very genuine with no fluff and shows that hard work, consistency and determination can really pay off. I hope to be at a point one day where I can be able to control what I do with my time and spend more of it with my family and have the financial freedom to travel to beautiful places like where you currently live. My wife has always wanted to go there. Anyway keep it coming and the you tube channel would be a great addition! Take care and God bless you and your family.

    • Thanks Darron, means a lot to me that I can be an encouragement to you! I’m going to be posting more soon and thanks for the encouragement to do more with the YouTube channel! Will do, take care!

  4. Hi Ryan,
    I have been reading your blog and was excited to read that you’re from Portland. My husband and I are planning to move to the Hilo side next fall. We fell in love with Big Island earlier this year. We are just waiting until we’re able to sell our Lent’s house. We’re planning to keep our photography business going and any other jobs. I am so inspired by your blog and can’t wait to live simpler. Keep up the great work! Michelle

    • Hey Michelle, that’s very exciting! It really is incredibly beautiful out here! Keep in touch and let me know anytime time if you guys have any questions or there’s anything we can help with!

  5. Well, without a doubt, you chose a good time to sell a house in Portland! I did the same in the Puget Sound area several years ago. Due to work, I wound up on the Vancouver, WA side of the Columbia river. Time to go now as well. I’m enjoying your forum here.


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