Roy Atkinson, former full-time musician turned IT professional, shares his transformative career journey.
Ever wondered how a full-time musician found harmony in the world of IT? Roy Atkinson's journey from music to tech is a symphony of adaptation and opportunity.
The Career Flipper podcast, hosted by Jenny Dempsey, explores the inspiring stories of individuals who've navigated unique and often unexpected career transformations. New episodes drop every Thursday—don't miss out!
In this episode, Roy discusses his passion for music, transition into tech, and the challenges he navigated. He emphasizes adaptability, the role of technology in his career shift, and the support of community.
Key Talking Points
Connect with Roy Atkinson
Featured Music Credits
All songs from the studio album "Beginnings and Ends" by Roy Atkinson, released by Fox Records:
The Painter’s Eye:
Pay the Bill in the Morning:
Explore Roy's music and connect with him to discover more about his career journey and current projects.
Jenny Dempsey (00:05.388)
to the Career Flipper, a weekly podcast featuring career change stories from people around the world in a variety of industries about how they get from point A to point B and all the twists and turns along the way.
I'm Jenny Dempsey, your career flipping host. After more than a decade working in customer service and experience leadership in the tech world, as well as teaching online courses, speaking at business conferences, and mentoring customer service agents, I found myself laid off and burnt out. Despite my experience, I couldn't land a new job and I really started to question my worth. Then a friend gave me an old table. I saw potential.
I binged YouTube videos to learn how to fix it up and I found joy in giving something unwanted a brand new chance at life. And this led me to start my furniture makeover and restoration business, San Diego Furniture Flipper.
Despite that, I was feeling alone and insecure about my new path. I mean, who really goes from the corporate tech world to covered in paint and sawdust in their garage? So I started reaching out to others I knew, just a few people who've also flipped their careers. And hearing their stories inspired me and made me realize that it's okay to change direction at any point in life.
And I also found out that there are way more people out there that have flipped their careers really more than I've ever imagined. So that's why I started this podcast, to share these incredible journeys and offer support to anyone considering having already been through or currently going through a career flip. So I really hope you'll find something in each episode that helps you on your path.
Jenny Dempsey (01:48.398)
Today, we're chatting with Roy Atkinson from South Carolina, who went from living his childhood dream as a full -time touring musician to a complete career flip into IT and even starting his own consulting company, Clifton Butterfield. In this episode, Roy shares how chasing your dreams, even if they eventually lead to a new direction, can be incredibly powerful and why community is key when making big life shifts.
Roy's story is a great reminder of the value of staying adaptable and open to new opportunities, even if they seem a little upside down. Plus, the music you're hearing in this episode is actually Roy's own. Alright, let's get into the episode now.
Jenny Dempsey (02:38.84)
Hi Roy, it's great to have you here. It's great to be here. Yeah, we know each other from the customer service world. We've met at business conferences and the like, and I have just always found your career flip story very interesting, even before I knew I was doing this podcast that would ever exist. So let's just get right to it. Roy.
Tell your career flip story. Well, Jenny, I made a big career flip some years ago. I went from being a full -time professional musician, songwriter, producer to being full -time in IT. And that sounds like a big stretch, but it really kind of made sense. I started playing music when I was just a little kid. My older brother, who's substantially older than me, is a very accomplished pianist and was classically trained.
And so I used to listen to him rehearsing all the time and going to his lessons and all that. A lot of times, if he wasn't around, I would go over to the piano and play what he had been playing, but I'd be playing it by ear. I became very interested in music and then I became really interested in playing guitar, which my parents weren't too thrilled about. They steered me into taking accordion lessons, which didn't last long. It lasted until it became important to buy an accordion.
And at that point, my parents said, you know what, these are very expensive, so we're not going to do that. And I said, OK, so I'm going for guitar lessons. And I went out. I mowed lawns and work around the neighborhood and for other folks close by and earn enough money to buy a guitar. Started taking lessons. And the little music school where I went was primarily interested in jazz. And that really wasn't my thing because I had
Listening to my older brother, a lot of this goes, it's all Brian's fault, my older brother's. He was in college and was in the Boston area. And so he was listening to a lot of the burgeoning folk scene in Boston. A very young Joni Mitchell, an extraordinarily young James Taylor, a guy named Tom Rush, who became one of my heroes. And I eventually got to meet him later on. I was listening to that and listening to a lot
Jenny Dempsey (04:55.95)
blues, and that's really what I wanted to play. I wanted to play that kind of music. And so I started teaching myself what I used to do. This is a pretty interesting technique. This is back in the days of the original days of vinyl, and I would take a 33 RPM LP, it on the turntable, but I set the speed to 16 because I made this magical discovery when I was probably about nine or 10 years old. I discovered that if I put a 33 RPM record at 16, it dropped everything exactly one octave.
So I could play along with it, but it would be much slower. It would only be half speed. And so I could learn the different patterns and licks and all of that stuff at a slower speed and then speed it up. To a great extent, I taught myself this stuff. And then I found out that a neighbor of ours right around the corner was a pretty accomplished acoustic guitar player, which I didn't know about him, a gentleman named Mel Burroughs.
Mel gave me lessons for a while and taught me how to do fingerpicking, which was a huge step for me. Then I just loved playing the music. I played every chance I got. Now in high school, I did play in a rock band. Of course, everybody who played guitar played in a rock band in high school. And I did do that. And we were fairly successful. We had some fun. But then by the time I was 16, I was working at a
then, part time, and one of the guys that worked at the supermarket along with me went to St. Peter's College in Jersey City, New Jersey, and they had a very well -known coffee house at the time that was called the Swan Song.
coffee house. This is right in the New York metropolitan area. So it was a popular place. And he asked me if I would come and play. So I did. And I did a couple of opening acts there at the Swan Song. And then eventually I got my own night at the Swan Song. Like I said, I was 16. I wasn't old enough to drive there. I had to get a ride to go there. Started doing that. I went to college. My parents did not support me going into music at all. So I held off and I held off and I held off and I held off. I went. I studied English lit and philosophy. I double majored in those
Jenny Dempsey (06:57.872)
So eight years later, when I was 23, 24 years old, I said, you know what, I'm doing it. And I decided to take a leap off the diving board, not knowing if there was water in the pool. And there was some water in the pool, as it turned out. And I started playing music full time. I was really dirt poor for a long time, but that was OK, because I was doing what I wanted to do and was able to make arrangements so that I could do that.
I remember there is a place that remains famous in the lore of Poughkeepsie, New York, which is what we refer to as the Mill Street home for Wayward Boys. And the Mill Street home for Wayward Boys was a tiny apartment which I shared with an actor, a novelist, and a guy who did science shows
kids usually only one and maybe two of us were there at the same time because we were off doing other things. was incredibly cheap. had no central heating. We had no telephone. I mean, it was it was pretty bare bones, but it worked. It kept us out of the rain. know, opportunities came along for me to start playing in some interesting venues and so forth and so on. I just kept at
As it turned out, there was a publication in the Hudson Valley of New York back then called Music Machine Magazine. And every year, Music Machine Magazine kind of covered the area from Westchester County just north of Manhattan, sometimes things in New York City as well. They would run an annual reader poll. And one of the categories in that reader poll was solo artists. And they started that poll in 19... Let me see if I get this right, 1980.
and I won in 1983, I won in 1984, 85, 86, and 87. And then they decided that they were sick of me. They established a Hall of Fame for Music Machine Magazine and stuck me in
Jenny Dempsey (08:46.21)
From then on, I was ineligible for the reader polls. I was playing three nights a week, four nights a week, and in some cases around the entire area, sometimes in Saratoga, sometimes in Westchester County. And I met up with a guy there named Lou DeCristofaro, and Lou is a bass player and did vocals as well. And Lou and I got together and we did some duo work. We played around New York City.
We played at a place called the Sloop John B in New York and we played some other clubs in New York. is from Long Island and so we played a lot around Long Island and I went up playing at a place called the Highway Inn in Hicksville. Matter of fact, at one point it was Billy Joel on Wednesdays and Lou and I on Friday and Saturday. Yeah, so I was able to do okay and made a reputation and eventually the gigs got a little bit bigger. I started doing opening acts.
Don McLean, worked with Todd Rungrin at Utopia. I worked with John Mayall and the Bluesbreakers. I worked with a British group called Renaissance. I loved those people. They were absolutely wonderful. They were a progressive rock group from Britain with an incredible vocalist named Annie Haslam. I worked with David Bromberg. I worked with just tons and tons of people. Eddie Rabbit, Kid Creole and the Coconuts.
I had just tons of people and you know, I remember one time I was an opening act at a civic center about 3200 or something like that. And the next night I played in a tiny club in New Jersey and it was four people. I didn't care. It continued and I kept doing that for a long time. I think at the time, the statistic was that out of people who considered themselves
musicians who identified as musicians, let's say in the current parliament. One out of 125 ,000 was ever able to make a living at it. And I did it for over 20 years. I consider myself extremely lucky.
Jenny Dempsey (10:49.166)
What an incredible career. And it's so interesting to me. And I think a lot of us are told at a young age, you know, you go to college, you study something that you can actually get a job in. And this isn't necessarily bad advice. I mean, it's, it's advice. And it sounds like you had this childhood talent that your parents really nurtured and they kind of fed into it for so long. And you clearly were exceptional at it.
going to college, you took that path. You took their advice, you went to college, but that fire inside you didn't let up. It kept at you and you were willing to sacrifice a lot to make it happen. And then you did it for 20 years as a job, which is what your parents didn't think was ever possible. And I think, yeah, I just think a lot of people can relate to this fact that it's sometimes hard to go for the things we want to, it seems impossible.
potentially against what everyone else is saying. But if we try, we may find out that we like it or don't like it. In your case, you loved it and you thrived. So I'm curious, Roy, when did the shift happen that you were like, okay, it's time to pivot and go into technology, go into IT. What happened? So I was a nerdy little kid when I was in grammar school, seventh grade.
memory serves me correctly, we started to learn binary math and ones and zeros and more ones and zeros. I got lazy or frustrated because we'd spend a lot of time in math classes translating decimal to binary, binary to decimal, decimal to binary, binary, decimal. And I was like, okay, I know how to do this. I don't like doing it. I'm going to come up with something that makes it easier for me. And so I did.
and I made a little device that would light up. A light that was on was a one, and a light that was off was a zero. Had a little rack of light bulbs. It would basically translate decimal to binary, binary to decimal, and I didn't have to do the work. I just looked at the light bulbs and saw one, zero, zero, zero, one, zero. When I was doing music, one of the things that I also did was I bought, very early on, I bought a personal computer, one of the first ones that was available. It was a European computer by a company called Amstrad.
Jenny Dempsey (13:11.704)
But one of the things that I used to do, which may explain some of the popularity I had too, was that I learned how to maintain a database of people who came to see me play and send out newsletters in the mail every month with a list of every place I was going to be playing and any other news that was coming up. If I had something going on that I wanted people to know about, I would let them know. And
After a while, also started teaching other musicians how to do that. explained to them that this was an advantage for them. If they would get computer literate and learn how to maintain a database and learn how to use a word processor, that it would be extremely advantageous to them. And some of them did. So, I mean, I was pretty nerdy. But as far as the real decision was as
time went on and I was working a lot in the recording studio and at that time, and we're talking about the early 80s here, the electronics were advancing incredibly fast. We were starting to see broad -based use of things like musical instrument digital interface MIDI so that you could program things and make an interface between a keyboard and synthesizers and different types of instruments.
Electronic instruments were really coming out like every week. It was like AI is now. was just stuff was happening very fast and wide. And I was increasingly interested in the technology. Having been a nerdy kid and being interested in technology, I said, no, wait a minute here. There is an interesting field that I'm not in. And I thought that the technology was
very interesting. And so I decided, well, you know what I'm going to do? I am going to get myself a job in IT. And the way that I did it was I set a deadline for myself. And that deadline was my 45th birthday. I said, let's face it, Roy, over 45, nobody makes it. So this is about as big as it's going to get for me in this field. Not that I wasn't having fun. I really thought about it and said,
Jenny Dempsey (15:33.89)
This is the time to switch. So that became the deadline. And in order to do it, what I said was, I'm going to give a year. So before that birthday, I started making the switch. I stopped accepting contracts that were outside of that range because I was getting signed to contracts. I was planning colleges and whatnot at the time and so forth. And I said, this is my deadline. And I started applying.
for IT jobs, entry level stuff. And I happened to get one and I got one that started three days after my deadline. And of course, having been a musician and traveling a lot, I could go anywhere basically, as long as I could find a way to live and gotten married fairly recently. And so the spouse and I were involved in all these decisions. We decided that one of the places that was very
good choice would be the coast of Maine. And so I targeted some places on the coast of Maine and in the state of Maine for jobs. And I got one at a place called the Institute for Global Ethics, was a think tank with offices there and in London, England. And they were looking for somebody who could help them run and modernize their computer systems. And I took it on and I took them,
Dragged them kicking and screaming into the 20th century. Moving made a huge difference for them. It was also a tremendous learning advantage for me. By that time I had gravitated toward Macs, computers. Became very knowledgeable about them, although the Institute ran on a mix of both Windows and Macs. I was there at the Institute for three years. After that, I was able to get to become a consultant with Apple.
joined what was called the Apple Consultants Network, which still exists. And I still have friends in the Apple Consultants Network. Became one of those people. I was one of the first people certified in OS 10 and went on to work for a couple of computer consultancies and have my own business as well. And then I got hired to do a project for one of the largest genetics research laboratories in the world. And
Jenny Dempsey (17:56.078)
was hired to do a project, which was about a year long for that institution. And then they hired me full time after that. And I was there for almost 10 years. And did you ever think back to doing music again? Was that chapter totally closed? What was that like? I think a lot of people don't understand that decision. I did play some concerts after I stopped doing it full time. But one of the things I realized was this.
When you do something all the time, and Jenny, you know this, everybody knows this, when you do something all the time, you get good at it. If you stop doing it all the time, you start losing that capability. And one of the things I knew was if I stopped playing full time, I would never be as good as I was then. And so that was important to me, that I was...
spot on. was a contributing factor. just the fact that I you know, I shifted from right brain to left brain or whatever, and I found ample opportunities in IT to be creative and to use some of the skills and education that I had. You know, I did a lot of tremendous amount of writing when I was in IT. And then of course, afterwards, through moving on through joining the organization called HDI, which was for IT support folks
and then getting hired by them to do work with them, did a tremendous amount of analysis on the industry and writing about it, so forth, which is pretty much what I do now. Yeah, you know, this makes a lot of sense. You you use the early technology to connect better with your fans. You created that database. You knew who was going to your shows. You knew how to connect with them through the newsletter that you printed and mailed out. And you created more of a fan experience.
really personalized to stay in touch. And it sounds like that was a big contributing factor to people continuing to show up at your shows. And I'm curious with all of the community building that you did, was there ever a time where, whether it was in your community of fans that may didn't want you to, didn't want to lose the music that you were making, or whether it was, you know, family or friends,
Jenny Dempsey (20:21.176)
Was there ever a time where people made comments to you about their thoughts on your career flip and your choice to move from music to IT? I think that you have to really be secure in what you're doing. I have never, I don't know, never considered myself that incredibly secure about stuff in a lot of ways. You know, I've got as many securities and neuroses as the next
I guess that having bucked the opposition of my parents when I was a kid in a serious way, it wasn't just rebelling. was, this is what I want to do and I'm being called to it somehow and you're getting in my way. But I, you know, I was, I was determined and I persevered and I went and did it. And, you know, I had to finance it myself. I had a plan at myself and I think having had that experience,
That enabled me to make the transition out of music as well as into it. I had come to a kind of a spot in myself where I was sure that this was the right thing to do. And I think that, you know, we do overthink and we do have imposter syndrome and all of that.
And you have to know when to reach out to people too and who to reach out to. Before I came back and started the business I'm in now, I did talk to a coach that I trusted and said, help me out here because I've got doubts about starting another business. It wasn't my first, it's actually my third time I've started a business. So I had some experience and I think I knew my weaknesses and some of my strengths. That coach was able to help me through some
some questions that I have. mean, right there, like that asking for help her. So many, so many of us, and probably a lot of us listening to this feel like, I'm, I'm, you know, maybe considering a switch, whether by choice or circumstance, you know, or I'm thinking about this thing that I really love that I have put any effort into yet. And I'm all alone with this. Like I'm, I'm, you know, not it's all in their head and to reach out, whether it's a coach or someone else that you trust.
Jenny Dempsey (22:39.55)
Someone in your industry talking to someone about to be supported is very helpful when you're on this unique path and you're making changes to something that's so deeply personal and part of your identity. Absolutely true. Developing that trust with people is just such a huge thing because it really has to be, if you're going to ask for help, it has to be somebody that you really, really trust because as you say, people might say, no, you're nuts.
And see, that's the other thing, Jenny, is that I knew that already. I knew I was crazy from the get -go. So I didn't, I wasn't about to be insulted or swayed by that because, you know, I was always off center and I knew it. exactly. It's like what Casey Musgraves says, own your own crazy. That's one way to do it. You know, Roy.
You are such a community builder and it would be great for some of our listeners to connect with you. Where can they find you? How can they reach out? I'm on LinkedIn. It's just the usual LinkedIn URL slash Roy Atkinson. One word. I'm on X as Roy Atkinson and the name of the company that I am the CEO for is Clifton Butterfield LLC.
CLIFTON, B -U -T -T -E -R -F -I -E -L -D, so very much like it sounds. Clifton Butterfield, and we're on the web and all of the above channels. So come find us. Thank you so much. Thank you, Jenny. Thanks for tuning in to this episode of The Career Flipper. Make sure to connect with Roy using the links in the show notes. If you enjoyed this episode, share it with a friend who could use some inspiration.
Rate and review the show and hit that subscribe button for more flippin' stories like Roy's every Thursday. Your support helps me reach more career flippers and future flippers to be, spreading the love, support, and motivation we all need on this journey. To connect with me, just head over to thecareerflipper .com. Keep on your path, my friend. What's the best that could happen? Talk to you next week.