11/25/2014 05:07 pm ET Updated Jan 25, 2015

5 Mistakes to Avoid When Moving to Hawaii

In April of 2012, my wife and I took a belated honeymoon (12 years later) to Maui, Hawaii. As soon as we stepped off the plane, we felt something we couldn't explain and knew Maui would be our home.

When we got back to Wisconsin, we talked about the move and what it would take. The details of moving to Hawaii scared us. After a few months, all the moving-to-Hawaii talk faded and we resumed our "normal" life.

Two years later, in April of 2012, my father died at the age of 54. No one saw it coming. At his funeral I vowed to live a life of no regrets. Two days later my wife and I had a serious conversation about moving to Maui.

It took a few more years, and overcoming many obstacles, but in April of 2014 our family moved from Milwaukee, Wisconsin to Maui, Hawaii. I made a solo trip in February to find a place; we signed a lease for March 1st. So, we have been here for eight months now.

During those two years, we researched, planned and talked to many people about the move. When we started to make the move, we found there were some mistakes to avoid when moving to Hawaii. Here are five major mistakes that keep people from moving or staying here.

1. Not having an emergency fund

I'm an author who writes about personal development and chasing dreams. I'm the first person to tell you anything is possible. However, trying to move to Hawaii without an emergency fund is foolish. There are many unexpected expenses when moving here, and not having an emergency fund will have you on a one-way flight back to the mainland. For rent alone you'll need the first month and a security deposit, which is the same price as the first month's rent. You'll drop thousands of dollars right away. I believe you can do this, but just in case, have an emergency fund. If you don't need it, you can then use it for something fun.

2. Not properly researching

A successful move to Hawaii requires researching many different aspects.

  • What island fits you best
  • What area on that island works for your situation
  • What your work situation will be
  • How much money you need to make each month
  • What's the best option for transportation
  • Insurance, shopping, and other details of living

Too often the research that's done is superficial. If you're going to change your entire life and move to Hawaii, you have to do in-depth and specific research to your situation. What worked for someone else might not work for your life. It's not wise to move and figure things out once you get here. That kind of move will have you homeless quickly.

3. Not making a survey trip

Research can only tell you so much and more than that, a lot of the information about moving to Hawaii gets dated. Coming here and seeing the research come alive can be vital in helping your dream become a reality. A survey trip will help you see if you want to be on a certain island or a certain part of that island. You can use this trip to line up work. Employers here are reluctant to hire someone over Skype.

You can talk to people that live here and get the real 411. You'll see where you would shop, visit where your children would go to school, and what will be your beach (that's important). You can also use a survey trip to secure housing, which is the hardest part about moving to Hawaii. It's easier to find a place once you're here. I would not advise moving here and staying in a hotel while you're trying to find a place. At the very least, rent a place through a service like Airbnb.

4. Believing everything on Craigslist

Craigslist can be a great resource for everything from finding a place to getting your furniture. There is however, a lot of scammers and lying, just like anywhere else. Use Craigslist in your research, but also check out local places like Maui News, the Civil Beat, and Huff Post Hawaii. We found a three bedroom, 1.5 bath home on Maui News for $1,300 a month (great deal). There are also many great blogs that could give you great information that Craigslist misses.

5. Trying to bring the mainland with you

Moving to Hawaii is not like moving somewhere new on the mainland. It's in the middle of the Pacific, the culture is different, and the way of life is different. Too often people move here and try to keep the same lifestyle as where they just left.

I was in line at Foodland the other day. The cashier rung up some items for person in front of me. When he told the person the total, I thought they were going to faint. They said, "These would be half of this cost in Texas." Things cost more here and life moves at a slower pace. When you move, you have to leave mainland life in the mainland and embrace your new home. This isn't the mainland and there are plenty of bummer stickers to remind you.

Despite the costs, moving to Maui was one of the best decisions we've made. We love it here and couldn't imagine living anywhere else. We live a simple, healthy, and active lifestyle.

If your dream is to move to Hawaii, you can make it work. It may require sacrifice, but all things in life that are worth it do. Have a plan and you'll be fine!

Are you planning a move to Hawaii?