Founder, Designer, Developer, Surfer

Emily and I have sold our home on Maui, and we’re moving back to the mainland. I’m sad to be leaving, but excited for the next chapter of our lives. In the 10 years total I’ve lived in Hawaii, this is the 3rd time I’ve left. However, it isn’t any easier.

I’ve been extremely fortunate to live in these amazing islands for most of my adult life. It has shaped me as an individual. Hawaii is a part of me. It’s difficult to explain to somebody that hasn’t fully experienced this land, or ʻāina. A vacation could never do it justice. I know the rocks, trees, reefs, and crevices of this island. I’ve paddled its bays, swam with its inhabitants, and crawled through its veins. After several years of exploring the shores of Maui, I’ve gained a spiritual connection to this wonderful land. In terms of natural beauty, weather, and the ocean — Hawaii is heaven on earth. I will carry those experiences and memories with me for the rest of my life. I’m sure I will be back, even if it’s just to visit.

If you’re reading this article and it’s your dream to live in Hawaii, please don’t use our decision to leave as any justification for not moving to the islands. That would be like not going to a great college because it’s expensive and far away.

The responses I receive when telling people we are leaving Hawaii for Florida vary, but they usually don’t favor Florida. The most common response is, “Why would you ever leave Hawaii?” That’s a fair question. However, if everybody chose their home solely by its level of comfort, beauty, and perfect waves, Hawaii would be the most populated place in the world…

So Why Leave?

Nobody was twisting my arm. There were no forcing functions — like a death in the family or loss of a job. The decision to leave Hawaii was an amalgamation of several reasons:

My Roots Are Elsewhere

Since listing our home for sale two years ago, I’ve been mentally checked out of Maui. As a result, the roots I planted have dried up. Some friends moved away, others lost touch. I stopped making much effort to establish new friends. My contribution to the community waned. It’s because my heart and mind were elsewhere.

While living with Emily in Sarasota for a year, I came to a realization. I’m a Floridian. I had almost forgotten. During my time back in Florida I fell in love with my wife. In the process, I fell in love with Florida all over again.

When stacking up the pros and cons of the only two tropical states in the country, Florida is usually found wanting. Personally, I have a conflicted relationship with the place. There are a lot of things to hate in that weird-ass swamp land, but there are a lot of things to love as well. I could never purge those white sandy shores, black water lakes, orange blossoms, and palmettos from my soul. My roots run deep in Florida. When I came back, I learned to appreciate the good with the bad.

“Why do you go away? So that you can come back. So that you can see the place you came from with new eyes and extra colors. And the people there see you differently, too. Coming back to where you started is not the same as never leaving.”

— Terry Pratchett

The Lack Of A Support Network

There are a handful of people I turn to if things get tough. Most of those friends and family are in Florida.

The next chapter of mine and Emily’s life will hopefully involve starting a family of our own. We are fortunate to have the freedom of starting a family virtually anywhere. However, that doesn’t it mean it should be anywhere. We want to be surrounded by friends and family. We want our children to grow up having a relationship with their grandparents. Raising a child will be very difficult at times. If Emily and I need to escape and reconnect as a couple for the sake of our relationship, we know it will be easier with family nearby. This was an important factor in our decision to leave Hawaii.

The Isolation

Hawaii can be very isolating. The islands are far from everything. That’s part of their appeal. However, it’s also a big reason why most people that move to Hawaii don’t stay indefinitely. It’s not only the distance that makes Hawaii isolating. In fact, I can deal with that. It’s the absence of a social life that makes a place feel truly isolating.

Due to the nature of my business, most of my interaction with people is done online. I don’t have a group of buddies at a job that I can shoot the shit with on a daily basis. In fact, I don’t have anybody on Maui that I need to interact with for my business. The only new people I meet are through surfing or by chance. As a result, my isolation on Maui often feels doubled. I’m lacking a healthy level of human interaction on this island.

The Boredom

It gets boring living on the outer islands. Not much changes on Maui — other than the traffic and cost of living getting considerably worse over the past 10 years. That’s part of the charm. However, when you’ve done everything and gone everywhere on an island, eventually you’re left with nothing to do.

I could usually beat back the boredom with surfing, but even that has its limits. In late 2017, I had the pleasure of surfing Honolua all to myself on an incoming swell — for 4 hours. It wasn’t huge, but it was ridiculously fun. If you don’t know anything about surfing or Honolua, just know that this is nothing short of an absolute miracle. It was as good as surfing could get for me. In that realization, I should have been ecstatic. Instead, there was a lot of sadness. I achieved the pinnacle of my surfing experience on Maui. It’s like the island was releasing me.

The Cost of Living

Any way you roll the dice, living in Hawaii is very expensive. Real estate, rent, taxes, gas, groceries, restaurants — it’s all absurdly overpriced. It’s not getting any cheaper. Nobody said paradise was cheap, but it’s a struggle to keep our heads above the water, much less save for the future. Moving back to the mainland gives us more opportunities for our future.

For The Business

My friend Jeff and I own and operate a small software company. We can work remotely. That’s why we started the business on Maui. However, isolating ourselves and our business on an island for many years has lead to some stagnation. Our business needs a shot of adrenaline that Maui is incapable of providing.

I Love Sarasota

I’ve scoured Florida looking for the best place for us to settle. I love the Keys, parts of West Palm Beach, Jacksonville and even Miami. However, Sarasota is my favorite place in Florida. As a kid, it was like a second home, roughly an hour away from my hometown of Lakeland. I spent a lot of time in the area, and I’ve always loved it. Emily was born and raised in the town. After living there together, my appreciation of Sarasota flourished. It’s paradise in its own right. Trading Maui for Sarasota doesn’t feel like a downgrade — except when it comes to wave quality.

Sarasota is more than snow birds and retirees. Although there is no shortage of the latter, the city also has great art, culture, night life, restaurants, weather, and beautiful beaches. There is a growing infusion of youth and new businesses in the city. Downtown has just the right amount of an urban environment without being overwhelming. It’s quickly becoming a boom town. It feels like a place that is growing for the better, and we’re excited and anxious to be a part of it again.

Our Plans

We will be visiting friends and family in Florida for the month of April. Then, we’re packing up the dogs in our Jeep, and driving across the country to Boulder, Colorado. We intend to immerse ourselves in a technology rich environment for a few months. Jeff and I hope this will be conducive to our business. The goal is to refocus and secure a new direction for the future of our company.

In the meantime, we will be looking for a permanent home in Sarasota. We intend to start the next chapter of our lives there. It’s a place we know and love, and that’s central to most of our friends and family.

To our friends in Hawaii we will be leaving behind, we’ll miss you and hope to see you again soon. To our friends and family in Florida and Colorado, we’ll see you real soon!

Aloha Maui. You’ll be in my dreams often.

24 Comments on “The Decision To Leave Hawaii And Move To The Mainland”

  1. I love you guys and you know I love Hawaii. I’ve been there enough to feel at home and wish I could have spent 10 years of my life there…I’m not sure I would have left! I’m looking forward to you guys coming home and starting a new chapter of your lives together in Florida.

  2. David, I enjoyed reading your blog and I could not be any happier that you and Emily (my Daughter) are coming home. We have all missed you both and can’t wait to see you guys and I am thrilled that you will be looking for a new home in Sarasota.

  3. Aloha! Having been in Paradise twice in my life, I’m back in Lakeland area and would love to get to see ya at some point. Just spent almost two years out in the Bay Area (East & North & Sac City). Sarasota is a good choice. And while Ha-vai-i has much to offer, FL has more in my humble opinion. Welcome home!

  4. That is a beautiful love note to two wonderful places. Well said! We are looking forward to seeing you both soon!

  5. I have read this several times now and am touched each time I read it. So well written and gives me some sense of what Hawaii means to you. Certainly, Hawaii will forever be a part of you and remain in your heart. A bit of sadness…..on a happy note, can’t wait to see you two. Love you…..

    • Thanks Amy! Yeah, it’s bittersweet. I’ve definitely had my moments of sadness during our last month, knowing it may be the last time I see or do certain things on island for a long time. But overall more excited about the future! Can’t wait to see you guys and the new house! Love you too!

  6. I too made the decision to leave after 10 years but having been gone a month I started panicking after day 3. Feeling very sad and confused and wish I could just get in the car and drive but preparing my large no of dogs for return won’t be easy

  7. I moved last year to Oregon after 36 years in Hawaii where I launched my career and raised my kids..I too felt I had done it all there..(surfing etc) and wanted a change and to be closer to family. Low and behold…what a culture shock! I am just not resonating with the mainland with its super highways and semi’s..and I hate the cold!!!! I am lost without the ocean and my friends, and guess what? My adult children do not need me here! They have busy lives of their own.

    MY shepherd ,whom I brought with me from Hawaii, died over a month ago, bless his heart..I am preparing to move my disabled and aged lab back. I’m going home to my “friends for life”, the ocean, the palm trees and plumeria blossoms. Sometimes we need to leave to get a fresh perspective.


  8. Did you move your household goods? If so, what company did you use or how did you do it? We are moving back from the big island, and don’t want to get ripped off, so any recommendations you may have would be great. Thanks.

  9. I am contemplating this myself. Just might pickup and leave with no plan other than a location and place to stay when I get there. Not the smartest plan but I feel so trapped; I have my eye on Oregon. Born and raised in Hawaii but I have always had a feeling that I never truly belonged here. I need to escape the traffic, low paying jobs, and high cost of everything. I’ve got very little holding me down to Oahu right now.

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