Accomplishing a Huge Dream: Hawaiian Adventure
Accomplishing a Huge Dream: Hawaiian Adventure

In the last post I wrote about some of the hardships and struggles that I overcame my first year working in the roofing industry.  Finding Rocky Mountain Roofing and Restoration was my last ditch effort at succeeding in this business.  One conversation that I had with a friend in February and gave me motivation to continue working hard was when I briefly told him that I started selling roofs. He also sold roofs part-time and he told me that by this time next year I could be spending a month in Costa Rica instead of enduring a cold winter in Colorado.

I couldn’t believe my friend at the time.  I actually couldn’t even fathom being able to spend a month in Costa Rica. At the time I was barely scraping by and using the last bit of savings that I had left to survive.

I started with my original company in February and I started with Rocky Mountain Roofing and Restoration in August. Rocky Mountain offered me the best profit share as well as a bit more since I was fluent in Spanish.  Once I started with Rocky Mountain I quickly got to working hard to ramp up my sales pipeline. I canvassed every day and talked to people that had already told me no.  I told them that I was with a new company and I could help them with their deductible.  This was during a time when it was still legal to help people with their deductibles.  I remember signing up my first few jobs and bringing the paperwork to the office.  The owner was surprised because he hadn’t done work in the neighborhoods I was working. He didn’t know that there was hail damage in those neighborhoods. He was also impressed that these jobs required new wood sheathing and they required multiple layers of roofing to be torn off.  Roofing jobs like this are expensive and profitable.

I was still struggling to make ends meet and then I finally got my first paycheck after a couple of months of working at Rocky Mountain.  It was about $3,500 dollars and I immediately felt rich.  I remember calling one of my good friends in Colorado and inviting him to dinner.  I was so excited and I didn’t even know what to do with the money.   The profit split I was earning was much higher than before and I was now making the kind of money that made this business worth going through the hardship.

Being more motivated than ever before I kept grinding it out day after day, weekend after weekend, getting on roofs, talking to customers, meeting with insurance adjusters, and collecting checks. By the time winter came around I had a good amount of money saved and my thoughts were leading to bigger things.

I brainstormed all the things that I could do and I had a tremendous sense of freedom. My housing expense was very low since I lived in a studio apartment. My car was a 1991 Volvo station wagon that was paid for and my insurance was around $80 a month.  There were so many possibilities since my overhead was so low and I was single with no family.  I was also 34 and felt like I needed to live.

I had originally moved to Colorado a couple years before mainly because I wanted to snowboard more often during the wintertime and in my first winter I broke my leg. It was an awful winter. I didn’t know very many people and I felt trapped in my studio apartment.  I had an air mattress that would deflate every night and I would wake up in pain and on the hard floor.  I couldn’t afford a normal mattress and I literally cried most mornings that winter because I was so miserable.

With that in mind, I thought back to what my friend had said earlier in the year about going to Costa Rica for a month. I also had another friend that I had met at a yoga studio who told me about a farm in Hawaii that takes in people to work and provides housing.  She really influenced me a lot and I began to think about going to Hawaii for a little while during the winter.

The more I thought about it and consulted with trusted friends about it, the more I realized that going to Hawaii for the entire winter was within my means and I wouldn’t have to work on a farm.  I figured that I could stay in hostiles, rent short term places, and I planned on camping out as well.

The idea of going on a Hawaiian adventure grew to the point where I knew I needed to do it. One of the best days I had that year was going to REI on a Friday night and being led around the store by one of their representatives and buying my high end backpacking tent, sleeping bag, shoes, air mattresses, and many other things I would need for my Hawaiian adventure.

The morning I bought my airfare was also exhilarating.  The fruits of my labor were becoming real.  I would be spending two months in Hawaii for the winter.  Two months turned into three months because I was enjoying my time in Hawaii so much that I changed my return flight and added a month to my trip.

That winter I backpacked the Napali Coast and spend five nights camping out on Kalalau Beach. I visited Kauia, Maui, Oahu, the Big Island, and Lanai.  I met incredible people who were also in recovery from Alcoholism like me and I practiced yoga in exotic areas of the islands. I hiked into the Kilauea Volcano and watch the lava bubble up before my very eyes while the moonlight came down out of the sky.  I spent some of the best days of my life in Hawaii that winter and it was due to working hard in the roofing business.