Meet Harry Dean

We were lucky to catch up with Harry Dean recently and have shared our conversation below.

Hi Harry, thank you so much for opening up with us about some important, but sometimes personal topics. One that really matters to us is overcoming Imposter Syndrome because we’ve seen how so many people are held back in life because of this and so we’d really appreciate hearing about how you overcame Imposter Syndrome.

I don’t think that I have ever actually overcome imposter syndrome. I think that it is important for my success as a musician to hold onto a bit of the imposter syndrome. Whenever I feel like something might be out of reach or I have not yet earned one opportunity or another one, that just gives me the motivation to work a little harder, or spend the extra time to write a song. Maybe it is practicing my guitar. I always find myself reaching for that next thing in my music career, just a little bigger stage than last time, and just throwing my name or my music in front of new people and just seeing what sticks. I have to sometimes take the time whenever I am feeling like I do not quite belong to look back at where I have been and appreciate all of the work I have put into this.

Thanks for sharing that. So, before we get any further into our conversation, can you tell our readers a bit about yourself and what you’re working on?

In my professional life, I am a Civil Engineer who works in Land Development in Grand Rapids, MI. I graduated from Michigan State University and went right to work at an incredible Architecture and Engineering firm back home. While my job is very fulfilling, I found myself searching for something more when my sports career ended and for that, I ended up turning to my love of music. With a love for country and rock music and a basic knowledge in guitar, I spent a lot of my covid days playing cover songs in my buddy’s garage in our first band that we called “Scratch Offs”. We played one show for our friends in this same garage with my buddies Tyler and Gage, and I fell completely in love with playing live music for people. When bars started opening back up, I started hitting open mics once or twice a week until I eventually landed a booking agent who could book me all over Michigan just playing 3-hour cover shows by myself. I spent my next two years traveling around the state playing 2-3 days a week just me and my guitar in the after hours of my job and on weekends. I spent a lot of time dreaming of something bigger though so I began really focusing my time on writing music and getting some bandmates. I reconnected with my drummer Tyler and found my lead guitar player, Lee, from an Instagram DM. Together, the three of us formed our band “Harry Dean and the Dusty Boys”. I started booking some of my own shows for the band while also keeping the booking agent shows playing solo once a week. In 2023, we released a 4-song live session to all platforms with some of my favorite songs that I have ever written. This live session was titled, “Late Nights”. This past year, I have taken a big step back from playing solo and focused all of my energy on the band. We released a few singles throughout the year all leading up to this November, releasing a 6-song EP titled “Feel Alive” that was recorded, mixed, and mastered all at Second Story Sound in Grand Rapids. We are all super proud of these songs and can’t wait for more and more people to hear them. As a band, we have played our biggest stages yet at some of our favorite venues in town like The Score and Rapid River Stillhouse. We have played our final show of the year as I prepare to take on fatherhood in December, but we look forward to keeping up the momentum in the spring of 2025 with a new slate of shows all starting on March 28th at Turnstiles in Grand Rapids.

Looking back, what do you think were the three qualities, skills, or areas of knowledge that were most impactful in your journey? What advice do you have for folks who are early in their journey in terms of how they can best develop or improve on these?

The three most important qualities for me were confidence, resilience, and love for music. Starting out in the local music scene was a difficult mental hurdle for me to get over. I think back to playing my solo cover shows, where I can remember one in particular when I played for absolutely nobody for the entire three hour show. The bar did not have a single customer the entire time I played. When shows like this happen, where I was not playing for many people, I would get in my head and think I wasn’t quite good enough, and maybe the music business isn’t quite it for me. I just had to rely on all three of those characteristics. I knew that I had played plenty of shows where people loved what I was putting out there. I knew that I just had to get through it and learn from this experience to take to the next one. I just had to remember I was playing shows because I truly loved it and keep my dream in mind of playing bigger and bigger stages and this was all just a step in the process.

The funny thing about my music career is that these feelings never quite go away. No matter the stage I find myself always looking for more and never really being truly satisfied. One day I will play my favorite show yet and then the next show will be a drag with a poor turnout. I always just stay true to myself and remember why I decided to do this all in the first place.

Looking back over the past 12 months or so, what do you think has been your biggest area of improvement or growth?

This past year, I have taken complete control over my career. I now book all of my own shows, write all of my own songs, and have truly trusted in myself. This would have never been possible without a great support system in my wife Madi, my bandmates Lee and Tyler, and an awesome community that shows up for us time and time again at our shows so that we can always impress a venue. I took the leap to stop booking with a booking agent this year and it has opened up countless doors for me that I originally did not think would be possible. I now have much more personal relationships with my local media, venues, and other artists. For the first two years of my career I always had a crutch of the booking agent, so I always knew that no matter how much work I put in, I would always have that next show. Now that I have taken this all into my own hands, my music career is a direct reflection of the amount of work that I put into it. I have to take it upon myself to connect with other artists for collaborations, I have to make my own relationships at venues to book shows, and I have to market all of my own music for anybody to hear it. This was all made possible by taking that leap of faith and trusting in myself.

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