Today we’d like to introduce you to Kevin Caffrey.
Hi Kevin, thanks for sharing your story with us. To start, maybe you can tell our readers some of your backstory.
I grew up on Long Island and developed a passion for music at an early age. When I was 13 I learned how to play the guitar so I could begin writing songs and 37 years later I’m basically still working at getting better at that. When I was a teenager I envisioned myself being a high school English teacher and went to LIU Post where I earned a bachelor’s degree in English and Psychology in 1998. Yet rather than going into teaching at the secondary level, I entered higher education and began working for St. George’s University School of Medicine as a Dean’s Letter Coordinator to assist 4th year medical students applying for residence. I’ve been in higher education on different college campuses ever since, mostly in advising or within a Registrar’s Office, where I’ve been working at the University of Mary Washington (UMW) in Fredericksburg since 2010.
After I earned my doctorate in higher education leadership in 2022 from Virginia Commonwealth University, I really wanted to dip my toes into teaching at the collegiate level. In the fall of 2022 I had the opportunity to develop a first-year seminar course at UMW called You Have To Listen To This: Connecting Through Music where we examine why individuals gravitate towards the music that they enjoy, and why sharing the music we love–and more importantly, the reasons WHY we love the music that we do–with others is crucial for developing strong interpersonal relationships. This fall is my fourth year teaching the course and it has become a popular choice among our first-year seminar options for incoming students.
Something that I’ve discovered through teaching the course now for several years that I didn’t anticipate when I created it was how, for many students, it becomes a sort of surrogate for their families and friends that they are away from while at college. So often when we’re young we share such powerful moments and experiences through music with our loved ones. With the course, incoming first-year students–many of whom are away from home for the first time in their lives–have an opportunity each week through our class meetings, discussions, and assignments to not only discuss, examine, and reflect on their prior experiences and their relationship with music, but they also are given the opportunity to create new experiences and bond with new people they’ve met at UMW over music as well. From my observations and from the feedback I receive from students who take the course, I think this really winds up helping first-year students with the transition from high school to college. It’s been a really rewarding experience for me to not only teach students about a subject I’m passionate about, but to also provide a unique and interesting pathway for them to succeed and thrive during their first year of college. It’s also been extremely gratifying to finally have the opportunity to combine my passion for music with my passion for higher education and teaching.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
I think the road rarely feels smooth for anyone, but I’ve been really blessed throughout my life in that I’ve always had food on the table, a roof over my head, and loving parents that worked really hard and made a lot of sacrifices to send me and my brother to a very good high school and help pay for our undergraduate education. That started us out on a road paved with good opportunities that not everyone is given and I try to never take that for granted.
One common struggle I’ve dealt with along the way though includes dealing with the doubt that often comes with starting new positions at new institutions and hoping you live up to the expectations of others and the expectations you set for yourself. I believe I’m fortunate in that area as well because I have a lot of creative outlets outside of work to alleviate stress and that bring me a lot of happiness and a sense of purpose. I recognize that not everyone necessarily has that in their lives so I’m grateful that I like to write songs, record albums, and perform live, conduct research and write articles on higher education and professional topics that I’m interested in, and publish weekly posts on creativity on my Substack account, Creative Hours. I’m also working on a book that’s an extension of my Connecting Through Music course. I think sometimes smaller schools like UMW may not get as much attention for the interesting things going on inside our classrooms compared to some more popular flagship institutions so I think it would be great to share a little bit about the course with individuals beyond UMW. I think the subject matter can be helpful not only to college students, but to parents, faculty, and administrators invested in supporting students with the transition from high school to college and really just about anyone who loves music and values its role in their lives.
So another struggle is just trying to balance everything that I enjoy doing *outside* of work with everyday domestic responsibilities as well. But this is a great struggle to have because it means you’re living a full and purposeful life doing things that are important to you and bring you joy and also being blessed to have people in your life who care about you to share these things with. It’s also important to schedule time to exercise regularly and take care of yourself, but also time to relax and unwind as well and not feel guilty about that. It’s great to be busy, but you have to prioritize rest as well.
I was diagnosed with ocular melanoma in the summer of 2025 that required surgery and a brief recovery period. This will mean CT and MRI scans every 6 months for the next 5 years, and then every 12 months for 5 years after that to look for any metastatic spread. This diagnosis and outlook has been a great reminder to remain grateful. Aside from some inevitable deterioration in my eyesight that will continue throughout the upcoming years, there’s been no major changes to my overall health and lifestyle and that is so often not the case when someone gets a cancer diagnosis. It’s been a great reminder to keep focusing on the things I love to do while I have the opportunity and ability to do so.
As you know, we’re big fans of you and your work. For our readers who might not be as familiar what can you tell them about what you do?
Probably what occupies most of my time outside of work is creating music. It’s been almost 40 years now of writing songs, recording albums that I release independently, and performing live. When you’re a teenager and you pick up a guitar and start writing songs and playing in bands you have that notion for a few years of “making it big.” Then that doesn’t happen and there’s an adjustment for a lot of people. Maybe you stop playing your instrument as much, members of your band begin to lose interest, you stop writing songs, performing live doesn’t seem as important as it once did, and that chapter of your life quietly comes to a close. I think by the time I was 20 or so I knew I was unlikely to ever make a living full-time through my music especially since I didn’t receive much formal training and my career was heading towards higher education, but I always knew creating music would continue to be a part of my life and I’m proud it still is all these years later. Writing music for me is all about self-discovery because I’m always hoping to learn new truths about myself through the process. Sometimes it’s revealed in the moment, and sometimes it’s not revealed until years later, so it feels like a lifelong quest. I just turned 50 and sometimes there is a sense of “You’re still DOING this? Recording songs on your own in your bedroom and lugging all your equipment around to play an afternoon gig somewhere an hour away from where you live?” But that’s all I really ever wanted to do when I was younger! Sometimes I get a leery notion of “Are you just doing all of this because you’re trying to keep that dream your 16 year old self had?” But finally I reminded myself, “Well, what’s wrong with that?”
Do you have any memories from childhood that you can share with us?
I have a lot of good ones, but recently my fondest ones have been the years I spent swimming on local and travel teams when I was around 8 to 11 years old. Biking a few miles everyday in the summer to our local pool and spending the entire day there was the best. When I was 12 or so I mostly gave up swimming, but I recently started incorporating it again about three times a week into my weekly exercise so it makes sense that I’m thinking more and more these days about that particular time of my childhood. The local gym where I swim also recently started piping in 80s music at the indoor pool where I swim so that is REALLY bringing me back! I’ve always felt a connection to the water and the ocean, and those themes have popped up a lot in my music over the years. This makes sense because I grew up on an island, but I never really thought too consciously about that at the time. I was just a kid and Long Island was where I lived, but a connection to the water has always been with me and I’ve been enjoying rediscovering this connection through swimming each week. Like music, it feels like another part of a lifelong quest in self-discovery that keeps me going.
Contact Info:
- Website: http://kcaffrey.com
- Instagram: https://www.instagram.com/kevincaffreymusic/
- Facebook: https://www.facebook.com/kevincaffreymusic
- LinkedIn: https://www.linkedin.com/in/kevincaffrey/
- Youtube: https://www.youtube.com/@oldirtycaffrey
- Other: https://creativehours.substack.com/
