SUMMARY
In this episode of Painterly Life, host Shannon Grissom engages with D. Shoji Nakamoto, a multifaceted artist who shares his journey through music and creativity.
They discuss the influence of family on Nakamoto’s musical upbringing, his songwriting process, and the cultural identity that shapes his work. The conversation highlights the importance of creativity in personal exploration and the balance between artistic expression and everyday life. In this conversation, Nakamoto reflects on the challenges of balancing a career with artistic pursuits, the journey of rediscovering painting after retirement, and the importance of overcoming creative blocks. They discuss the significance of finding a personal rhythm in creativity, the necessity of downtime to recharge, and the desire to explore larger artistic projects. The conversation also delves into the fascination with portraiture and the process of allowing the painting to guide the artist, culminating in the belief that curiosity is the essential spark for creativity.

CHAPTERS
00:00 Introduction to D. Shoji Nakamoto
03:00 Musical Roots and Family Influence
06:00 Songwriting Journey and Inspirations
09:01 Cultural Heritage and Personal History
12:10 Balancing Art and Career
14:59 Overcoming Creative Blocks
18:02 Creative Process and Intuition
21:08 Exploring New Artistic Directions
23:56 The Evolution of Portraiture
26:03 Curiosity as a Creative Spark
TAKEAWAYS
D. Shoji Nakamoto grew up in a musical family in Hawaii.
- He started as a lyric writer influenced by the singer-songwriter era.
- Cultural heritage plays a significant role in his songwriting.
- Balancing a day job with artistic pursuits can be challenging.
- Overcoming creative blocks often requires stepping back and refreshing perspective.
- The creative process can lead to unexpected outcomes in art.
- Curiosity is essential for maintaining creativity and inspiration.
- Portraiture allows for the exploration of personality and character.
- Shoji aims to work on larger canvases to expand his artistic expression.
ABOUT SHOJI
Born in Honolulu, Hawaii, Derek Shoji Nakamoto has cultivated a life rich in culture, creativity, and career diversity. His heritage is deeply rooted, with grandparents who immigrated from Japan and Okinawa in the early 1900s, and both parents being born in Hawaii in the early 1920s.

Derek’s educational journey began with an Associate degree in business management, illustrating his early inclination toward practical skills that would serve him throughout his varied career. He started in retail management within the footwear industry, where he honed his leadership skills from 1978 until 1999. Following this, he transitioned into operations management in transportation and warehousing, which he pursued until 2006. His commitment to workplace safety led him to serve as a Safety Coordinator in food distribution from 2006 until his retirement in 2023.
Beyond his career, music has been a significant part of Derek’s life. He learned to play the ukulele at the age of nine, followed by clarinet study during his early teens. At 14, he picked up a hand-me-down guitar from his older brother, igniting his passion for music. By the age of 20, he was performing small gigs and songwriting with his friend Karl Nishio. Derek spent a significant ten years in Los Angeles from 1988 to 1998, where he continued to pursue music on and off. After returning to Honolulu in 1999, he rekindled his musical partnership with Karl, ultimately releasing his first original CD, “Field of Stones,” in 2004, followed by “Songs the Wind Whispered” in 2017.

D. Shoji Nakamoto

by D. Shoji Nakamoto

by D. Shoji Nakamoto

by D. Shoji Nakamoto
In addition to his musical endeavors, Derek has always had a profound appreciation for the arts. In high school, he thrived in drawing, painting, and film, initially aiming for a fine arts major in college before deciding to focus on business. However, after his retirement in 2023, Derek revisited his artistic roots, reigniting his passion for painting and sharing his work on his personal website.
Derek Shoji Nakamoto’s journey is a testament to a life fully lived; from his roots in Hawaii and his dedication to family, career, and creative pursuits, he continues to inspire those around him through both music and art.
LINKS
Website: http://dshojinakamoto.com
Facebook: https://www.facebook.com/dshoji.nakamoto/
Instagram: https://www.instagram.com/dshojinakamoto/
X: https://x.com/DShojiNakamoto
Transcript
Shannon Grissom (00:05.72)
Hi, I’m Shannon Grissom. Are you looking to ignite your creativity? Or how about be inspired by a steady stream of muses? Welcome to Painterly Life, the podcast that celebrates those who create, inspire, and innovate. So whether you’re looking to spark your next big idea, reignite your passion, or simply soak in some creative energy,
This is the place for you. Painterly life, where every guest is a new muse, just for you.
Shannon Grissom (00:50.306)
Welcome to Painterly Life. I’m your host, Shannon Grissom. Today we have D. Shoji Nakamoto and he is a painterly powerhouse. He’s a singer-songwriter. He’s a painter. He plays multiple instruments. Welcome Shoji.
Thanks for having me Shannon
So what’s the weather like in Honolulu?
it’s beautiful. It’s probably about low 80s. Trade winds are blowing. I’m blessed to be here.
You are. One year, my grandmother sent our family and our cousins. we got to go to, we went to Oahu and Kauai for Christmas. And it was just, it was magical. It was really cool. So is your entire family musical? I mean, you played so many instruments from, from ukulele, clarinet, keyboards, guitar. So were you born with an instrument in your hand?
D. Shoji Nakamoto (01:38.932)
great.
D. Shoji Nakamoto (01:55.138)
I guess in Hawaii, as kids, just a lot of kids grew up with the ukulele. You can see them, you know, they’re walking around with ukuleles in their hands and strumming away. And that was much the same way. But as far as that goes, clarinet, really, I spent two years in middle school, beginning band playing clarinet. So that wasn’t much but
Really, that’s the extent of my formal training, really, because the guitar I just picked up and started playing inherited my brother’s old cigar box guitar and started playing. My family is very musical, though. My mom’s side of the family has a lot of singers, musicians. My brother plays guitar. My other brother plays ukulele.
My niece and nephew are musicians at the university level, so they’re pretty accomplished too. So guess you could say we’re a musical family.
That’s awesome. Did you all jam together when you were younger or did you each do your own thing?
You know, it’s funny, with all the music around us, we all pretty much did our own thing. But when I recorded my first CD, I was really glad that I got to include my niece and nephew. My niece plays oboe and my nephew plays euphonium, and we were able to get them tracked and included in the CD. So I was really happy with that.
Shannon Grissom (03:33.71)
awesome. It is. You know, think playing together is fun and and when you sing with family, maybe it’s just the genetics of the voice, but there’s nothing like family harmony. Just it’s a cool thing.
Yeah, I think so too. I wish we did more of it, but it is what it is.
Yeah, yeah, my family’s scattered, so I’m not playing with them right now, but it’s all good. So you started songwriting at a really early age. How did that start?
Really, I was a lyric writer in the beginning. When I was in high school, I did a lot of lyric writing because my prime time for music was the singer-songwriter era. So I was influenced a lot by people like Joni Mitchell, Jackson Browne, James Taylor, Eric Anderson, Dan Fogelberg people like that. So I was always interested in lyrics. So I started as a lyric writer.
for a long time in my teen years. But then I hooked up with my good friend Karl Nishio and we started collaborating with songs. I was primarily the lyric guy and he was the music guy. you know, really we never went anywhere with any of our compositions, but it was a good learning experience for both of us. And that’s kind of how the songwriting thing started.
Shannon Grissom (05:03.699)
Well, you paint a beautiful picture with the wishing tree and let’s have a listen.
D. Shoji Nakamoto (05:45.952)
In younger days we carved our names upon your wishing tree, drew a heart around them, promised it would be just you and me. And we lay back in the shade and watched the clouds fly high above, to children in our innocence in love.
As we climbed the twisted branches, fears were lost and knees were skinned Told each other stories, heard the song of leaves and wind And the kiss I stole when you weren’t looking took you by surprise Do you recall the promises we made?
If a million tears should fall, I’ll be there to dry them all A thousand dreams untrue, I’ll be there to see you through And if a hundred years go by like stars across the sky Here I am, there I’ll be The heart carved upon your wishing tree
D. Shoji Nakamoto (07:21.526)
So days turned to weeks and years and we made other friends
Girls turned into women, young boys into men And the kisses I once stole from you belonged to someone new But I remember it promises did you
D. Shoji Nakamoto (07:48.792)
day I learned from an old school friend that you had moved away Gone off to chase your dream he said, somewhere in LA I wrote a letter, never sent it, kept it by my bed It was filled with silent promises it said
A million tears should fall, I’ll be there to dry them all A thousand dreams untrue, I’ll be there to see you through And if a hundred years go by like stars across the sky Here I am, there I’ll be The heart carved upon your wishing tree
D. Shoji Nakamoto (09:06.274)
Just yesterday they carved their names upon your wishing tree, Drew a heart around it promised love same as you and me. And they lay back in the shade and watch the clouds fly high above to children in their innocence and love.
Climb the twisted branches, fears to lose and ease the skin Tell each other stories, hear the song of reason win He will steal a kiss when she’s not looking, take her by surprise Fill her heart with promises and say
If a million tears should fall I’ll be there to dry them all A thousand dreams untrue I’ll be there to see you through And if a hundred years go by Like stars across the sky Here I am, there I’ll be The heart carved upon your wishing tree
D. Shoji Nakamoto (10:26.286)
the heart carved upon your wishing tree
Shannon Grissom (10:48.942)
It’s a beautiful, magical, whimsical song. Can you tell me the history behind it? What’s the story? There’s gotta be a story.
I don’t know that there’s a real story. A lot of my songs are composites of people, personalities, narratives, stories, experiences. So there’s a lot combined into that song. But it does kind of hearken back to a very relatable incident for a lot of people. know, of course, know, first love, things like that. The very
a nice remembrance of it. And of course, in the end, coming full circle with another two people, you know, experiencing the same thing. So it’s a relatable thing. But really, the origins come from a lot of different places and a lot of different experiences, not just with me, but, you know, really anybody who can relate to that.
Yeah, I get that. I wrote one song and my, after I put it out, my stepdaughter called me and said,
Are you and dad okay? Yeah, we’re okay. I said, I’m making this stuff up. You know, I mean, it comes like you said, it comes from a bunch of different places and, and something will happen and I’ll go, that’s a great song. That’s a great idea for a song and then you run with it. So yeah, I do get that.
D. Shoji Nakamoto (12:27.712)
Yeah, well, that’s a good thing because a lot of times when you can peak somebody’s interest or relate to somebody that an experience that they had as well, they will be affected by it. And for a creative person, you really want to be able to, I guess, poke people and peak their interests, you know, and that’s that’s really the ultimate for creative person.
I agree. I’ve been at an art show before and people will just sometimes they’ll just it’s great when they engage. Sometimes they’ll just walk past your booth. So the worst thing is to have no interaction. But yes. So so I agree when you strike a chord, that’s just beautiful. So I speaking of strike a chord, Son of My Father, it’s just a beautiful song. And you talk about having
one foot in the east and one in the west and I would love to hear share me some insight on the you know behind that song.
Yeah, that one is actually a specific or my specific family history. Really, there’s not a lot in there that’s made up. My grandparents came to Hawaii as laborers in the sugarcane fields and I’m the third generation removed from Japan.
You know, being third generation removed, you are almost totally removed from your root culture. so hence, one foot in the East, one in the West, you feel like there’s a pull back to a culture that you know very little of, because I’ve been here for so long. there’s a lot that
D. Shoji Nakamoto (14:28.458)
is involved in this particular song because not only a family history but an immigrant ancestry that a lot of people can relate to. You lose part of who you are if you don’t reach back to your root culture. And in addition to that, there’s also a pull that pulls you back there too. this one was
actually easy to write and yet difficult at the same time. But yeah, it’s a specific family history of mine.
Well, it’s just wonderful that you can get in touch with that through your creativity. I yes, I feel like the to really go in deep knowing myself or working through anything, it’s it’s whatever creativity, whatever creative thing I’m doing will take me in there and you do a deep dive. Otherwise, I’m just kind of going through the motions and not really there. So I think it’s awesome.
So you’re definitely in the flow. I love, I think it was your father in the song about dancing in the stream and going with the flow. so is that something that was said to you or was that a reoccurring theme?
I think it’s not something that’s specifically said. think, and I don’t want to mislead anybody by that because there’s going with the flow doesn’t necessarily mean that you just go with everything. know, it’s like, like, life is like a river flow. You know, there’s a time to go with it, but also a time to swim to your own path.
D. Shoji Nakamoto (16:29.006)
Going with the flow sometimes means that there’s a direction in life and you choose whether you follow that direction or not and from somebody somebody that’s in a creative world That’s often something that you you you fight with Do I? Go the conventional way or not?
You know, so it relates to a lot of different things, not just life in general, but for the creative mind, it’s a constant thing, really.
So you’ve been able to be incredibly creative even while holding a day job. how did you, I mean, you’re amazing. How did you balance all of that?
I don’t know that I did balance. It’s difficult. It’s difficult. And my career is totally different from my artistic side. And it required a lot of time. So I was able to do the music side of it because I would gig occasionally and had my regular dates and things like that. But
I unfortunately I had to put aside part of it and part of it was the painting side of it. You know, when I went to college, my intention was to be a fine arts major and I started in that curriculum. But the practical side of me somehow made me change and I became a business student all of a sudden, you know, so there was a lot that was left behind when I started my work life.
D. Shoji Nakamoto (18:17.592)
Fortunately, I’m back.
You are back. You are back and you’re painting up a storm. did that happen after you retire? How did the painting come back? How did that start working its way in?
When I retired, of course, my full intention was, yeah, I get to paint again. Wow, that’s great. But it wasn’t as easy as all that. I tell you, looking at a blank canvas after so many years is really difficult because you lose a lot of the craft of what you do. Everything I learned when I was back in school and
And in school, there’s a lot of studio time and art labs and things where you can hone your craft. I had to relearn everything. I’m standing there with a paintbrush in my hand, not knowing what to do. You know, I had to learn everything from mixing colors to how to handle a palette knife to composition and perspective and the whole bit.
and it was difficult at first. But I think I’m working my way through that still. But it’s been fun.
Shannon Grissom (19:41.294)
Well, what’s amazing is that you’re doing it. You’re not letting the difficult part of it stop you. I see a lot of parallels with me. I started off with my music, then my 30s started painting and my 50s started getting my music back. And I’m still, I’ve got a lot to learn. so I did feel like I was starting over. it was frustrating when I,
I played the clarinet too when I was younger and when I was younger, my fingers just knew where to go. They just went there and I just, they just knew what to do. And with the guitar, they do not. I’m still learning. I just, I think it’s huge that you’re, so how did you push past resistance and the difficult challenges that come with starting a new medium like painting or going back to it?
I can relate to that.
D. Shoji Nakamoto (20:39.618)
You know, there are times when you can push through things and keep just keep working and working and working. But for me, there are times when I have to back off. I might be working on a project and going through the phases of a painting and get stuck all of a sudden. It’s almost like a writer’s block, you know, and I’ve heard that.
You know, a solution for writer’s block is to just plow through and start writing, writing, writing. But that doesn’t work for me. For me, I find it better to back off. I will just put it away. I will not look at a painting. I will not listen to a new piece of music that I’m working on. I would just put it away.
When I come back to it, I’ll come back to it with fresh eyes, fresh ears, fresh perspective, and I’ll be able to work through better. So for me, it’s, and even as I’m working through a project that is actually going well, I will stop every so often and I will walk across the room and look at it from, you know, across the room and I’ll turn it upside down.
and I look at it, you know, just to freshen my eyes again. And that’s what works for me. I have to take a time out and I have to, I have to refocus. I have to refresh. So backing off is usually my best solution to blocks and walls and resistance.
It’s great that you know yourself and you know what works and you just do it. do you have? For me, I have certain times a day that that work better for me to do for painting and another time that that is better for me for music. Do you have is yours that structured or do you just do it whenever?
D. Shoji Nakamoto (22:46.798)
I can’t say that it’s structured. As you probably know, Shannon, I think there are times when things strike you and you have to go after it. yet there are times when it’s best for you not to pursue it. you have to kind of know where your pocket is. are times when you know that you can get rolling on something.
And yet there are times when it feels forced once you start. And for me, that doesn’t work. it’s a difficulty to know when to do something or when to create something. But I think after a while, you kind of know yourself and where and how to go and when to go.
So it seems like for your resistance, you tend to just back off and let it come to you when you start again. I getting that correctly when you are stuck? that your best?
For the most part, the most part, like I said, also though, there are times when you can plow through something and work through something and, but you kind of have an instinct that, okay, if I do this, I can get there to the next phase, especially in painting, because there are times when things aren’t working out, you know, because paintings go in phases, right? And your initial phase, you think you got it.
And then the next phase goes and things aren’t going the way you think they’re supposed to go, right? So, it’s a process. there are walls that you know you can fight through. And yet, there are times when it gets so frustrating that maybe you should back off. So, that’s kind of been the way I do things.
Shannon Grissom (24:51.736)
Yeah, I find that when I pushed through it, when I should have backed off, I hurt it. So I know better. In fact, I wasn’t feeling so good the other day and I thought, OK, I am not going to touch what I’m working on. I’ll just start something different or do something different because I will hurt that painting.
Yes, yes, I’ve had that.
D. Shoji Nakamoto (25:13.334)
Yeah, yeah, and that’s a difficulty because you know there there’s a tendency for me sometimes to say okay, I have time to paint but now I Have no creative I’m not in my creative mode. So it doesn’t work So scheduling time is difficult you you try to take advantage of Something that inspires you of course
to do something creative, but to match that up with time. And everybody has life that, for lack of a better way to put it, gets in the way of creativity. you try to cope as best you can.
Yeah, and I think there needs for me, I need to have some downtime to fill the well. So, you know, taking a walk or pulling some weeds or doing something completely unrelated. Visiting with people that, you know, that just helps me fill the well. If I get too into it, I can’t. It’s like, like you said, you need to get back from your painting and I need to get back as a whole from all of the creativity or I.
It’s messy. It’s a muddy mess.
Yeah, it does get that way.
Shannon Grissom (26:36.622)
Do you have any new projects? What are you working on now? What’s on the horizon for you creatively?
As far as music goes, I have my regular play dates and gigs and whatnot and I’ve been fortunate that I’m able to do farmers markets for the Hawaii Farm Bureau and I do that twice a month. That’s always fun because there’s a lot of people milling about and you’re just doing your thing and it’s always fun. From the visual arts side, I’d like to work bigger.
I think most of my projects recently have been either 12 by 14 canvases or 12 by 16 or whatever they are. So they’re relatively small, but I’d like to work a little bigger. I don’t know if you can see the one in the back of me, but that’s a bigger one. That’s a 24 by 36. I think it’ll open up a lot creatively because not just the physical space, but
Now it changes your perspective on composition and balance and you can work in detail a little better on a larger scale. So I’d like to work a little bit more on larger canvases if I can.
So I can just see you going for it. You’ve done a lot of beautiful paintings with women, and you have a metaphysical, otherworldly quality. I feel like their spirit is there. It’s not just a likeness. Can you tell me about that series of paintings?
D. Shoji Nakamoto (28:29.742)
Well, first of all, I like to do different subjects. But of course, I always come back to portraits because I don’t know, people just fascinate me. There are different levels and personalities and characteristics and moods and you know, people just fascinate me. So from that point of view, you know, when you get
to start working on something. And I’ve done portraiture for specific people with specific subjects. And that’s a little different for me because you have to pay attention to the detail of the likeness and things like that. But when I’m not doing a specific subject, I have fun with that because I never know how it’s going to end up. And it’s almost like
It’s almost like the subject takes a life of their own as you’re progressing through it. You you do the first phase and you have a general idea about the composition of it. But once you start putting in the details, the pose, the face, the eyes, they all of a sudden start to control you. You know, they have their own life. And I find that process fascinating because I never know what
personality this subject is going to take on when I finish it. And I just love that process.
Do you find that sometimes they change personality mid-painting that you start off in a certain way and then in the end they’re a different person?
D. Shoji Nakamoto (30:11.884)
yeah, a lot, a lot in fact. And you know how this goes, but when you start something, obviously there’s a procedure, your background and whatnot and phases of developing the form and things like that.
Once you get into the personality of the subject, you never know where it’s going. I just love that. I love that kind of portraiture because I’m not trying for a likeness now. I’m trying to find out what this person is. And that’s always fascinating.
Well, I think it’s interesting that you are listening to the painting and working with the painting rather than imposing your will on it. And it makes for a lot more interesting work.
Yeah, it does. you know, we were talking about resistance earlier and that prevents a lot of block and resistance because when you end up fighting the painting because it’s not going where you want it to go, you find that block happening and it’s a lot easier, you know, to, you know, go with the flow, you know, kind of thing.
I
D. Shoji Nakamoto (31:40.296)
And it’s also a lot more enjoyable to watch the process unfold that way.
Yeah, the painting always wins. it’s just, it’s a matter of whether you’re going to, you know, allow it to do that.
Yeah, and that’s a good way of putting it, know, allowing it to happen. Yeah. Yeah.
Wow. So any final thoughts on creativity that you’d like to share?
I think for me, I think as long as I maintain my sense of curiosity, I will always find some kind of spark to create with. Because, I’ve always felt that curiosity is a spark and a spark is only a spark because you have to process it in your creative mind and your heart and then evolve it into something you can materialize into art.
D. Shoji Nakamoto (32:40.534)
And of course the materializing of it also requires you to have a competence in your craft. So it’s a real process, you know, but for me it all starts with a sense of curiosity. And if I ever lose my sense of curiosity, I’ll be a sorry creative person. But that’s what works for me. And curiosity is the key for me.
Somehow I don’t think you’ll ever lose that, Shoji. Well, thank you for being here. You’ve totally been inspiring.
Thank you for having me, Shannon. This was fun.
It is fun. Well, thank you for tuning in to Painterly Life. Please visit our website, like, subscribe, and share. For more information on Shoji, please visit dshojinakamoto.com. And until we see you next time, I wish you all inspired action. That’s a wrap.
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