What I Learned From Hawaii


Now that the fun is over, I’m resigned back to a life of dull monotony. You know the drill — wake up, go to work, leave work exhausted and stressed, relax for a few short hours, go to sleep, and then start the day all over again. What a lovely life…

Since I just arrived back after a three week hiatus from paradise (Hawaii), naturally, you might have guessed that my spirits took a plunge off the deep end. 🙁

That’s ok. Hawaii was obviously a tease, but I did learn some valuable things that will help guide me further in my quest to early financial independence. In particular:

  • The world is vast and there are lots of places to explore, things to do. It would be a damn shame to go through life and not experience as much as possible. When I look back, I want to have ZERO regrets.
  • Believe the hype. Hawaii is absolutely gorgeous. The weather, the beaches, the environment, people, everything. I really didn’t believe Hawaii would live up to the hype because I expected so much from it already. Still, it exceeded all my wildest imaginations. I found heaven on earth.
  • I don’t want to settle! For instance, I’m definitely not a cold weather person. Even the Bay Area is too cold for me around this time of year (except this Winter, which is unusually warm). There are places out there, like Hawaii, that provide warm weather all year round. If such a place exists, why not move there permanently? I’ve seen snow… I love to snowboard. But I can definitely do without it since I prefer to be in shorts, tank top, and flip flops year round.
  • I want a tropical paradise. Hawaii may be out of the cards because the cost of living is so high. To have my cake and eat it too, I’ve started to entertain the thought of living overseas. After all, it’s my life, so I get to direct and star in this motion picture. Why not live in a cheaper country where your dollar goes a lot farther? The only real point in living in an expensive area is to make a lot of money. Once you’ve achieved this goal, why not go someplace cheap so that you can maximize your hard work? Lately, I’ve been thinking about the Philippines, Thailand, Bali, etc. I could even island hop… 6 months here, 6 months there, etc. If things really don’t work out, then I’ll try and find a creative way to end up in Hawaii (semi-retirement/part-time gig).
  • Back to the topic of weather, I believe it can have a profound impact on your daily life. I seriously believe if I lived in Hawaii, it would easily add 10 to 15 years to my life. When the weather is so absolutely perfect, it prompts you to go out and do things. In the Bay Area, I have no interest to go to Santa Cruz beach. However, when I was in Kaanapali, I was lured to go swim in the warm, clear water.
  • Motivation is now at an all time high. I’ve seen the alternative to “Life in a Cube”. That movie is a rotten tomato, and I want sooooooo much more out of my motion picture. Let’s make this happen. Let’s shoot for retirement at 30. There’s a lot of life to live and I don’t want to waste another moment.


What about you? Have you gone on any vacations that changed your outlook on life? Where do you want to ultimately end up?



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Financial Samurai
6 years ago

I’m pumped you’re digging Hawaii!

I took a month long business trip last Nov/December and wrote a post entitled, “If You Can Make It In Hawaii, You Can Make It Anywhere.” I’d love to get your thoughts. The post is linked in the website bar.

So what are your plans? Time to move eventually too??

Mrs. Sbs
6 years ago

Could not agree with you more. We live in a city that gets lots of snow, which is great for the first two weeks but you kinda get sick of it when it continues for another 5.5 months. We took a trip south a couple weeks back and it always amazes me how different life is there. People still go outside and have fun during the months of November-May? Wow! During those months our city transforms into a ghost town. Don’t even get me started about the lack of sunshine, uggh! I’m totally with you about moving some place warm.… Read more »

6 years ago

We went to Kauai a few years ago, and we still think about it all the time. We have been thinking about renting a home somewhere in Hawaii for a few months to test it out 🙂

Fast Weekly
6 years ago

Welcome back FI, even if you feel mixed about it. At least Hawaii gave you something to remember and shoot for in the future. Something to hold in your heart (and visualize) when you wonder why you’re working so hard to create a steady and sustainable cash flow. EVERY vacation changes me. Every one reminds me that my daily job isn’t what I’m met to do forever. I’m meant to make a difference in this world. That is what I find fulfilling, and why I work so hard for financial independence. In the shorter term it’s all about my 2015… Read more »

6 years ago

No matter what, ending up somewhere warmer is definitely the goal. Doesn’t hurt if it happens to be tax advantageous as well since that will help minimize the amount of dollars needed to retire. It certainly wouldn’t hurt my feelings to go full time ex-pat, but the lucky little lady doesn’t have quite the comfort zone that I do.

JC @ Passive-Income-Pursuit

I like the cold but not to live in. It’s nice to visit but I don’t know how the people living in places like Chicago or Buffalo deal with all the cold and snow. Although I’m sure they feel the same about that Texas heat in the summer. I’m hoping to be able to take a trip to Hawaii soon. I’m pretty annoyed that I haven’t made it there yet. I’ve only visited a few of the Caribbean islands but you’re absolutely right that there’s so much to explore and learn. Even if you limit yourself to just the US… Read more »

Dave @ The New York Budget

You just got me fired up! Let’s do this – let’s retire early and make the most of our lives!

6 years ago

Agree. I think one day I will move to warm weather. Las Palmas comes up as best climate, though I would prefer 5 degrees warmer:
My ideal would be:
-between 75-90 all year long
-low humidity
-sunny, low rain
-no car needed – preferably this means good public transit, not never going anywhere.
-related – good base for visiting other places (flights or trains are cheap and close)
-nice size population

Dividend Mantra
6 years ago

FI, Now you’re talking, my friend. Speaking my language. Preaching to the choir…and all that. I could almost live off the income my dividends and online ventures provide me now if I were up to living in Thailand or somewhere similar. The idea does sound quite intriguing! The only thing that concerns me is the thought of being so far away from family. Does that ever cross your mind, or are you not close to family? I moved to Florida from Michigan because I’m also not a cold weather person, and I figured getting by without a car and avoiding… Read more »

Done by Forty
6 years ago

Great takeaways. Hawaii can definitely remind us that there is a benefit to sunshine and good weather, and the simple pleasures of nature. I’m glad you have a direction for your life: go get that leading role.

6 years ago

Thailand is amazing… I really want to go back and see the rest of SE Asia. I think I could definitely live there if I could move all my friends and family out there! That’s the huge spanner in the works for myself and I am guessing a lot of people though. If you can work out a way to do that and still come back to see your family enough and be happy then more power to you and I say wholeheartedly you should go for it! Funny you say about not being a cold weather person… there is… Read more »

Pauline @ Make Money Your Way

I think my round the world trip for a year after college showed me that life is much, much cheaper abroad and you don’t need much (thus less work) to live well.
There are a lot of tropical paradises South of the U.S., you may want to look into these as it would be easy to keep a freelance job in the States (similar time zone), fly back in 3-5 hours instead of 12-18, and learning Spanish is much easier than Mandarin.
Anyway, just my $0.02. Glad you had a blast in Hawaii!

6 years ago

I have been following your road trip. Have you considered crossing the pond to Europe. The Mediterranean offers some very exciting places to live !
South France


[…] What I Learned From Hawaii FI Fighter took a vacation to Hawaii and got a taste of freedom and all the beauty it comes with. Now he’s more motivated than ever. I feel the same. I feel invigorated right now, and I’m inspired to retire even before 40. I feel like big things are still in store for me and I’m going to take every opportunity I can. […]