A Little Story About How I Was Living the Good Life on Maui – and Threw It Away, and Why

I grew up in a low to mid-income family which consisted of my mother and two younger siblings in Western Pennsylvania. It was cold – much too cold for my tastes, and a couple of experiences in which I was so cold I couldn’t feel fingers or toes left me wanting another side of life. I didn’t know what it was yet because I was so young.

Then when I was 14 years old my mother piled us all in the car and said, “Let’s drive to Ocean City, New Jersey!” Ocean? Really? I was excited because I knew I’d see girls in bikinis, but that’s all I figured on enjoying. As it turns out, there were three foot waves breaking close to the beach and I went and stood in them for a while, fought them for an hour or so, and had the first taste of salt water in my mouth. It was my first taste of many things that trip – real beach, saltwater ocean, and girls in bikinis as far as I could see.

It was to be the transforming moment of my life right then and there.

From that point on, I knew I wanted to live at the beach. I wanted to be able, at any time, to go fight the waves. I didn’t know anything about riding them, and there were no surfers at the beach I was at with my family that day, but soon enough I’d see them. Later I went to Myrtle Beach, South Carolina with my girlfriend and that was a great time too. The beach life – it was for me. It was without a doubt – exactly what I needed to have in my life.

I enlisted in the Air Force right after high school. Had tech school in Biloxi, Mississippi – an absolute hole, but despite owing four years to Uncle Sam, I had a taste of freedom there. I was actually free from my family. I was free from friends, coaches, teachers, everyone in my life who was ever important before. I was free to be me.

It was a huge stroke of luck to be sent to Hawaii at Hickam Air Force Base on Oahu for four years. I didn’t expect it. I chose all east coast bases near the ocean for my “Dream Sheet” which is nothing more than that. Just a way for the Air Force to help new enlistees feel comfortable about having absolutely no control or say over where they’re going.

Life in the Air Force in Hawaii was paradise. Even though I had little freedom to do as I pleased, I used it to the limit. Stepped over the limit sometimes too. Had a blast really. Met some of the greatest guys to hang out with – workout with, run with, drink with, bodyboard with, snorkel with… the best times of my life by far. The fact that we were in Hawaii just made it so much better.

When I left Hawaii I was married to a Canadian girl who modeled and we headed to New York City where she had a great offer we couldn’t pass up. I wish we would have passed it up though, in hindsight. After a few years I was on my own and heading down to Miami to go to college. I figured I needed to learn something besides photography. Again, in hindsight, there was no need to learn anything but photography, but nobody had ever told me I could be a photographer. A writer. Author. All these things I did later, but it’s funny how many times in life that we have something good – we’re on the right track, and yet we think there’s something more, something different, that will make everything right… that’s destiny or something. In hindsight…

It was fourteen years before I made it back to Hawaii. I moved to Oahu and got a job with a small tech / marketing company. I was fired from there for not being a good cog in a system. I quickly found a job on Maui as a marketing manager for a well-established property management firm which managed five nice properties, three on Maui and two on Big Island.

I never felt comfortable in the position. I wasn’t a traditional marketer, I was an internet marketer and the company was accustomed to spending lots of money with print ads and on other traditional media. I wrote up an internet marketing plan that called for spending around $75,000 in the upcoming year on digital media. It would have been the beginning of catching us up to other places we competed with like the Hilton, Sheraton, and more, who were already spending hundreds of thousands of dollars on their annual budget for their Hawaii properties.

Anyway, they weren’t going for it. It was sometime after this that I found myself along with the head of sales, at a gathering in a home sitting on a hill overlooking Kapalua golf course, and the pacific ocean. The home we were in was worth around 2-Million dollars at that time. Today they’re worth $3.5M. There was nothing that special about the home, it was well built. It was one story and big enough for all ten of us. It was surrounded by similar homes, some slightly larger, some smaller. There were over a hundred just in that gated community, and there were more surrounding us.

I remember thinking how amazing it was that I was there. I didn’t feel part of the company, and the people who owned it and invited us out to eat and drink weren’t anyone special to me personally. I didn’t know them. I noticed something about them though. I noticed they seemed to be very comfortable with the excess. They were comfortable with the extravagance. Their company was started by their parents and it rocketed skyward quickly claiming the top spot for tour packages to the Hawaiian Islands. Apple Tours I think it was called. The house was bought only two years before, and they’d not been there even a handful of times since their parents bought it. Still, they acted as if they belonged there. Like it was expected. They took it for granted.

I was making decent money, and along with my partner and an extra internet business we were living well. We ate at some of the finest restaurants on Maui, often. I don’t remember eating at home to tell you the truth. We spent way over $1,500 USD on eating out each month. We loved it. We were fit, and exercised a lot, and we ate like fiends. I remember thinking a number of times – wow, this is it. Maui is paradise found. There isn’t anything better than living on this island and eating this food, snorkeling and freediving, bodyboarding, surfing, fishing, and camping. Still, I wasn’t comfortable because it was too comfortable. If that makes any sense. There was no more struggle. I guess I grew up with, and need the struggle to feel normal.

So back to the dinner party.

When some of us marveled at the location, the view, the opulence of it all… they blew it off as really nothing. It was ‘normal’ to them. It was taken for granted. I think that’s really the feeling that got to me, and that is getting to me now as I think back on it.

There are people who are naturally successful because they expect nothing but a high level of success. They reach their goals, however excessive, and they exceed them. I’ve never even seen that in my family as I grew up. I had one uncle and aunt that were making decent money, but they were both employed by the government and were salaried. They probably saved a couple million dollars, but that was over dozens of years – 30-40 years of working?

So anyway… I was living on Maui and I had a great job. The job was easy. It wasn’t fulfilling. In a way I took it for granted because I figured I should keep moving toward a bigger goal. I needed to keep advancing with my own projects, not working for someone else. I needed to really crank something out, something amazing. Something my own.

So I moved to another job that was risky, but I hedged my risk and though it turned out OK for the short term, it left me a bit aimless. I left Maui and moved back to Florida briefly, then made a huge jump and moved to Thailand in 2004.

And today I’ve gone a number of different ways. I haven’t worked for someone else since 2006. I’ve pursued my own online projects since then. Some have done OK, and many have failed. I’m still looking for the one thing that is ‘my thing’ and I still don’t have the slightest idea what it might be. I’m interested in so much, and yet I am a generalist – and not a true master of anything. Being a master of something seems boring to me. I wish I was, but then I don’t have the desire to do the work and become a master of something.

So, I’m 50 now. Apparently Colonel Sanders and a thousand other people were over 50 when they started their ‘thing’ that worked out for them.

I sometimes think about living on Maui and the quality of life that I had. It was perfect really. I don’t know why it wasn’t sustainable long-term. I think to me life is a struggle and if I’m not struggling, then I’m not living. Having everything I need and want just isn’t satisfying at all because it feels like stagnation. It feels like I’m just swimming upstream but not going anywhere.

Somehow that isn’t acceptable to me, and I prefer to struggle.

So, I’m struggling here in Thailand and sometimes thinking back to “the good life” living in Lahaina.

Is that really the good life, or is there something fundamentally lacking in a life like that?