Rambling Across America with Tommy Ray

TR Fly

Carl Hose: Tommy, a lot has happened since we talked last. You’ve made some big steps in your career, there’s a new book, not to mention you went through a hurricane and spent how long without power? We’ll talk about the new book in a bit, but how did the hurricane affect the timeline of your plans and how did it affect you creatively?

Tommy Ray: After coming off the road from the “Confessions of a Dreamer Tour,” in May of 2016. I pondered my next step. I allowed fear to re-enter my mind and chose to return to the matrix of a safe day job. I relocated to St. Croix of the US Virgin Islands. I am basically about 1900 nautical miles south of Miami, FL. On the surface, St. Croix is the most majestic Caribbean Island you could ever dream about. That was until September 2017. Within two weeks, two separate Category V hurricanes crashed through all three Virgin Islands. The first was Irma, which only skirted by us. I saw no damage even though St. Thomas was leveled. Unbeknown to me, Maria was to follow less than two weeks, landing directly on us. The hurricane lasted over 12 hours, with sustained winds of 175 mph and gusts over 220 mph. I was in a bunker about 5 feet underground, surrounded by concrete to ensure safety.

The next day, I was able to walk around my complex and view the horrific damage. We were under 24-hour curfew for about 5 days, where you could not leave your house for safety. Overall, I went 3 months with no daily power or clean running water. I had a generator, which I would run a few hours during the day and a couple hours at night. The remainder of the day was nothing but the aftermath of Hurricane Maria for us. On the island of St. Croix, we use cisterns (wells which catch the rain water) for our water supply. The hurricane tainted those. A neighbor would pour gallons of bleach into his to somewhat make it safer and ran a garden hose to my apartment so I could begin taking a shower after about 6 – 8 weeks. Up to that point it was boiling water on a camping stove and taking sponge baths. So, with that said, going almost three months without power meant no cell phones, along with no Internet. My original motto was as long as I had Internet, I could live anywhere in the world and maintain a voice to the world with Tommy Ray Entertainment (a new umbrella company for Tommy Ray Books, Tommy Ray Insights, Tommy Ray Music, and my YouTube Channel). There were many days I would have anxiety thinking how much ground I was losing in exposing my creative outlets to the world. Besides the actual darkness (here gets dark around 6:30 pm every night), I was losing faith I could have my voice heard. When I was able to talk to family or friends about I am safe, I have food, I have drinking water, most of my musician friends were like, you must be writing tons of lyrics with everything going on. Sadly, my creative energy was nonexistent. I did not write a single line and barely strummed my guitar. It was a dark age for me indeed. I now find myself with mild shell shock when I see a new storm brewing in the Atlantic Ocean that might be heading our way.

CH: Let’s talk about the book. I read it. There’s a lot of positive messages in there, a lot about music, your views on life in general, and some great stories. How hard was it to capture your journey? Did you find you had to pick and choose what to put in and what to leave out?

TR: Thank you for the kind words, I am truly grateful. I am still a newbie as an author. I love to write as well as compose lyrics, however, it is different writing a book and describing what I was seeing, thinking, etc. Verbally, I was creating a lot of inspiration for the choice, the risks, the adventure. However, my vocabulary is quite straightforward. So many of the sights I saw were not described in enough detail to have a person truly sense my emotions as I was driving through a mountain range in New Mexico or up the California highway alongside the Pacific Ocean. I attempted to keep a daily journal to remind myself of details as I chose not to begin writing the book until after the tour was completed. Perhaps a mistake I shall not make on future “Country Boy” adventures. Another difficult aspect was desiring to capture the landscapes with pictures. I desired to stop every few minutes for another shot. Sadly, I knew I had to keep driving to reach the next town/city. The same with street performances or venue performances. I wish I had more video from those experiences. Ultimately, I did not desire to bore with too many details, which meant trying to figure out what to utilize for the book and what to discard.

I did have to pick and choose material. For the most part, each day was the same thing. I woke up, drove to a town/city, either performed on the street or located a venue to perform, then went to sleep. I did this for over 7 weeks. That routine was fine with me, yet boring to a reader. So, I tried to utilize the important interactions, certain performances, or sights I saw to allow insights to the tour, yet keep anticipation for the reader.

CH: I have to ask this. You’re a songwriter, a musician, and really good at it. I love your stuff. Do you prefer writing books or your songs, or are they two different things altogether?

TR: You are very kind. First, I simply love to write. I desire to read, learn, and write each day, every day. I prefer lyrics. I now consider myself a lyricist. The reason why is when I write, I compose to basic boring open chords on my guitar. My producer Jimm Mosher of Hit Music Studios in North Carolina creates all of my music. I may give him the key of the song or a basic tempo, but he has other top quality musicians perform the melodies as he arranges the overall product. In my eyes, if you are a songwriter, you also can create the melodies, breaks, intros, etc.

Please do not get me wrong, I love being an author. I desire to continue my travel series of “A Country Boy” as well as I recently added suspenseful short stories to my repertoire. I truly desire to create inspiration and value to the world. I am utilizing multiple types of media to perform this goal/desire/dream.

I plan my week accordingly. Monday and Thursday nights are music nights, Tuesday and Wednesdays are author nights. Sundays are for my blog writing. Saturdays I try to actually venture out into nature for the day. Then I intertwine my YouTube channel along with various other activities of reading, learning, etc. throughout the week as well. So, I work my current day job to about 5 pm, then come home for a break of an hour, then I work on the above activities to about 11pm to midnight each night of each week.

CH: You gave up a pretty good career to do the things you’re doing. How many times have you heard people say you lost your mind? What were some of the struggles involved with giving all that up to pursue a dream, both internally and externally?

TR: I have heard that from more than I can count and a lot from family. This was the second time I exited a premium job which most would think a dream to listen to my heart, maintain unwavering faith, as well as trust my instincts. I departed a position in 2012 and walked the Camino de Santiago (about 600 miles through France and Spain). The “Confessions of a Dreamer Tour” was the second. A little secret, a third is on its way.

External struggles were the financial. Overall, I owed $200,000 in school loans plus about $15,000 in credit cards. In order to accomplish this trip, I had to put the school loans in forbearance, (increased interest), cash out assets with large tax penalties, move out of my apartment, and place everything in storage.

As mentioned before, the family kept saying how I was wasting my life, I should stick to the job, find a girl, settle down, and stop these foolish dreams of mine, but internally, I was actually at peace. I sensed I was doing what I was meant to do. It was like a load of boulders were removed from my shoulders on that last day of the day job. I was confident everything would work out through blind, unwavering faith. With the mottos of “if you want a new life, rewrite your life,” “One shot at life,” “Never give up on your dreams,” and “Do not take this life for granted,” I was grateful I was able to do this.

“One does not discover new lands without consenting to lose sight of the shore for a very long time.”—Andre Gide

CH: What is one of the biggest challenges you’ve had to face traveling so much?

TR: I am alone. I am in solitude a lot. However, I am happy. I am strong enough to handle this. Besides, this is my choice. No one is to blame or twisting my arm. I am a quiet person anyway. So, add the transitions. It creates a quiet path. I mean, I have lived here on St. Croix now for two years and I have minimal contacts. I do almost everything alone like hike, paddle board, snorkel, relax at the beach. My belongings are in storage, so I do not feel like I have a true home yet. Though a lot of this could be due to the way I was raised. I attended like 3 kindergartens, 2 or three 1st grades, 2 or 3 second grades, and 2 third grades before relocating to North Carolina in the 3rd grade when my parents separated. But even through those years and college, I lived in multiple different apartments. So, I have never had a room which was mine where I can visit now and see memories. I was born into a rambler lifestyle and guess a reason I love to travel. In my opinion, the world is a massive, abundant, beautiful place, created by God. I desire to see it all. I am sure one day I will meet a woman who would like to join me on my adventures, lol . . .

CH: Talk a little about your songwriting process. Do you write all the time, only when the mood strikes, and do you have any special way you prefer to do it? Do you start with a title, keep notes, use a computer or write by hand?

TR: I go through phases with songwriting. I currently have about a dozen half written songs. I dedicate two days a week to my music. Reading articles, gaining wisdom/knowledge about all aspects of music. I practice once or twice a week singing and playing through my equipment for about an hour each time. However, if an idea hits me, I ensure I write it down. So, if I cannot work on it at that very moment, I have the idea on paper to add to my to do list.

I find the best time for me to write is after being placed into a highly emotional state. After an emotional movie or YouTube video, a lot of times my mind will flow with ideas. For example, after watching “A Star is Born” as well as “Bohemian Rhapsody” in the theaters, I rushed home and worked on lyrics as my heart was talking to me.

When I try to sit down and tell myself, “Okay, let’s compose,” I first strum basic chords like D, C, and G or variants until words begin to flow. I do not record, which is a mistake, because I have lost many great words or lines. After I compose a few lines or more, I then build off of them, finding improved words, or play with the structure to find a unique twist. I then use an App called “OnSong,” which has all of my lyrics on it. I will use it like a piece of paper. It allows me to copy and paste and frees up a laptop so I can research themes of what I am attempting to describe. I still find a pen and paper quite valuable. I believe the pen and paper are connected to my heart and soul.

CH: Is everything composed on guitar or do you play keyboards as well?

TR: I only use my guitar currently. My mom once owned a piano. I can play about 5 basic chords on a piano. It does add a different texture to my writing. At times when writing, I may have instrumental music playing in the background as I improve an older song or update a song I am working on currently. I do not use programs to write lyrics, but I will research on a laptop themes or phrases I can use to portray a scene as I write to tell stories.

CH: What are your favorite foods on the island? Is there a lot of good local food?

TR: Here on St. Croix of the US Virgin Islands, the main local dishes are: Goat, Ox tail, Conch, Saltfish, a unique black stuffing, seasoned rice, Patte. The positive about the island is there is limited fast food, (2-McDonalds, 1-Wendys, 1-KFC, 3-Subways). Everything else is local restaurants. Food is expensive here. Exmple, a basic single cheese combo at Wendys will cost you almost $9). There is a woman who has a grill at a gas station down the road who serves grilled chicken with two sides for $10. I eat a lot of Mahi, chicken, tacos. St. Croix is a food paradise. Like mentioned above, I can take you to a place you can eat for $10, then another place where it will cost you $40 for a small entrée. The best time to eat is during our special events. People will grill out chicken or beef kabobs, patte, along with fried chicken legs.

CH: Do you have any regrets since you’ve started your journey? Would you do it all the same way again?

TR: The major regret after the completion of the “Confessions of a Dreamer Tour,” I stopped. During the tour through posting on Facebook, I made some friends in Nashville. In hindsight, I should have gone there to at least perform at some songwriter nights. Instead, I visited family in Mississippi and Florida and I lost some of the spark I had. I began thinking about the future instead of maintaining the present moment. I allowed some fear to enter, now I am back at a day job again.

In hindsight, I would still complete the tour the way I did, but I would have performed more. I spent three days in Lubbock Texas lying in bed drained and exhausted. They had a venue for songwriters and due to the start time being 10 pm, I chose not to go. I beat myself up for not performing there. I also talked myself out of street performing in quite a few cities. It was surprising how negative it was looked at in the cities I visited. I mean, I was told to stop performing by police in Austin, Texas, the capitol of live music with people around me listening. In order to perform, you needed permits which could cost up to $150. Great if you lived in the city full-time, but not great for what I was attempting. In the beginning, I did attempt to have scheduled stops where I would be paid to play. I sent out over 100 emails and did not get a single response. Perhaps if I tried a different technique I could have had gigs lined up.

CH: You’ve changed the name of your company. What is the address of your website and where can you be reached on social media. Plug your book and your record. Where can people buy those?

TR: I created Tommy Ray Entertainment. It is basically an umbrella company for all of my creative endeavors.





Twitter: @TommyRayBooks, @TommyRayMusic, https://twitter.com/TRayEntertainm2

Facebook: Tommy Ray Books, Tommy Ray Music, Tommy Ray Entertainment, Tommy Ray Insights

Paperback: “Rambling Across America

Digital: https://books2read.com/ramblingacrossamerica

CH: What are your plans for the future?

TR: Currently writing one new book to continue my “Country Boy” travel series. I am writing a second short story to be part of “Amid the Blackness.” These are suspenseful thrillers of 1,000 – 3,000 words. The first was “Mirror of Perception.”


I recently recorded two singles at Hit Music Studios. My producer has them ready for mastering. So, maybe in December or January 2019 I can release those. I write a weekly inspirational blog on my Tommy Ray Insights website. I began building my YouTube channel. I am creating a weekly “Confessions of a Dreamer” series.

The debut video: https://youtu.be/pGXOx5zZf74

Besides those, I read daily to increase my wisdom, knowledge, along with insights to keep improving myself so I can ultimately live my dream life. The ability to create inspiration and value to the world and in return, I profit from royalties so I can be free to travel, write, compose, and assist others in attaining their dreams. I desire Tommy Ray Entertainment to be a global brand which sustains myself without the day job and others dictating how I must live.

CH: Thanks for talking to me again.

TR: It was my pleasure Mr. Hose. I am truly grateful and appreciative. Please remember anything is possible. Dream big, my friend. Do not let anyone ever talk you out of your dreams. I truly believe there is nothing you cannot achieve. Become the best version of yourself. Imagine, living your dream life. May I be the example.

“Difficult roads often lead to beautiful destinations.”—Unknown.

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