Meet Lenny San Jose

We were lucky to catch up with Lenny San Jose recently and have shared our conversation below.

Lenny, we are so deeply grateful to you for opening up about your journey with mental health in the hops that it can help someone who might be going through something similar. Can you talk to us about your mental health journey and how you overcame or persisted despite any issues? For readers, please note this is not medical advice, we are not doctors, you should always consult professionals for advice and that this is merely one person sharing their story and experience.

I feel like mental health is something that goes largely unchecked as a working musician. Whether it’s social media posts or running from gig to gig, we tend to have to put on an aura that we’re always having a good time even if our day to day can be a struggle. Working musicians put on many hats in order to pay the bills and keep this creative life going, and it’s definitely overwhelming at times. I’ve been on my own mental health journey this year, after being diagnosed with bipolar disorder and ADHD. I had a manic episode for the first time and am still recovering from that heavy experience. I’m lucky however to already have a lot of the growth mindset training that comes with being a creative, an artist, and a musician. To be a musician, you have to practice fundamentals regularly – like finger exercises, scales, chords on my ukulele. Then you have to learn your songs, get your set list together, and perform regularly until you’re comfortable with audiences small and large. When you learn a new technique, you already know that you’re going to have to work at it before you can use it at your next performance. You have to be okay with not being good at something on your first try, and have the confidence that you are an avid learner, a scholar, and can eventually become great at anything you are trying to achieve.
My journey with mental health is the same. Being open to discussing my deeper feelings with my partner, my friends, my therapist was not easy at first. But every repetition brings me closer to where I need to be. When I was in my darkest moments I’d be afraid to text my friends, and I didn’t want to feel needy. But it’s amazing what a simple check-in will do, and your friends are eager to pick you up when you’re feeling down! Especially now I feel like we’re all yearning for a sense of connection with others, and with practice I’ve been more confident to just reach out to others.
The other side of it is to have an outlet that isn’t directly related to your craft. I love music but I even need a break sometimes, so I turn to basketball, juggling, other hands on activities to stay engaged but in a more adjacent way. Some of my favorite musicians are killer chefs, designers, visual artists, scientists, and I love to see how their work ethic as a musician translates into all sorts of other fields.

Great, so let’s take a few minutes and cover your story. What should folks know about you and what you do?

I’m a full time Ukulele musician based out of Oakland, CA. I’ve been playing music my whole life, studied to be a music teacher at Cal, got my teaching credential and put in 5 years as a public school music teacher. Since 2016 I’ve been only performing and teaching privately, and it’s been an amazing journey thus far. I began playing ukulele in 2008, mostly practicing on my public transportation commute (the BART train in the Bay Area). I started up my YouTube channel, Ukulenny, and my first tutorial of “I’m Yours” started to attract views in the 10,000s, which was a lot at the time. So I made a bunch of tutorials and covers not really thinking much of it, but eventually I got introduced to the Ukulele Festival circuit, playing at events such as the Wine Country Ukulele Festival, San Diego Ukulele Festival, Northern California Ukulele Festival, Mighty Uke Day (Lansing, MI), Ashokan Uke Fest (NY), LA Uke Fest, and Reno Uke Fest, to name a few. In 2016 I had the honor of signing on as an ukulele artist with Kala Brand Music, and still represent the brand and travel to trade shows and events preaching the ukulele gospel.

I also partnered with YouTube star Cynthia Lin to host events in the Bay like the SF Uke Fest and SF Summer Uke-Splosion with Yerba Buena Gardens, and we toured the West Coast and Europe with fellow ukulele star and percussionist Abe Lagrimas Jr. Our group U3 has been featured at several uke fests, and released the album “In Waves” in 2020. These days I perform with my jazz duo partner Bob Frazier, “The Bob and Lenny Show,” and my island reggae trio “Ukulenny & Dos Pogi Boys.”

My love for the ukulele is deeply connected with my love for music in general. I was the kid who would make music with anything I could get my hands on – empty paper towel rolls, rubber bands, jamming out at dinnertime with my spoon and fork. When I was introduced to the ukulele, I immediately saw how easy and accessible it was to beginners, and I saw its strength as a social instrument. It’s very unassuming and lighthearted. The guitar, you have to train your fingers and get calluses and it takes 6 months before you can sound good, but the ukulele you could be playing full songs by the end of a 5-10 minute lesson. Ukulele jams are popular – meetups where everyone brings ukes, chords are shared, and everyone participates in a few hours of songs and laughter. Because I enjoy playing music so much, I’ve made it a goal in life to ensure that other people can experience that same joy, and the ukulele just makes it so easy to do so.

Currently I’m excited to share my first E-Book, Moving On Up, available at the Ukulele Magazine store (tinyurl.com/ukeonup). This book provides an overview of what beginners can do to continue their growth towards intermediate and advanced levels. I also have monthly classes on Patreon (www.patreon.com/ukulenny) and continue to stay connected in our friendly ukulele (and bass) community! Lastly, I’m just excited to continue playing music here in the Bay Area and beyond. I’ve recently been playing more saxophone and as a solo live-looper, have been able to incorporate lots of different instruments in my live performances.

There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?

1) Never stop learning.
I’ve always stayed curious from when I was growing up to now, as a 37 year old. My jazz duo partner, Bob Frazier, just turned 80 and says that he never stops learning. So we have no excuses! I remember all my older siblings learning these hard math problems during dinner and I was that annoying younger sibling trying to out-answer them. If you can stay motivated, there’s so much more you can get better at in your own craft, and it becomes a way of life.
During covid, musicians had a tough time losing the ability to get out and perform live. I, like many others, took it as an opportunity to get better at video editing, streaming (who else learned how to use OBS during those years), and was able to build my Patreon community that is still going strong today. Learning those skills was no easy feat but it was totally rewarding in the long run.
2) You are your greatest asset.
I was looking for some extra cash after college and picked up a job on Craigslist selling car wax at gas stations. I only stayed on for a week, but the 2 days of sales training has stayed with me to this day. Probably the most important thing I picked up, is that when someone buys something from you, they’re not really buying the product, they’re actually buying YOU. If you present yourself at your full value, it’s really hard for your customers and your clients to say no. And if they happen to say no, then perhaps it wasn’t a good fit. Or you weren’t the product that they were looking for. When it comes to being an artist, define your values and what you care about the most, and then go hard and own that identity. Then when you go out there and do your thing, you’ll find your community and those people who support you.
3) Keep making stuff.
When I started my YouTube channel over 15 years ago, it was easier to get noticed and now I feel like it’s really hard to make an impact. Nevertheless, I think the same advice holds true, that you need to keep making content for all sorts of reasons. One – you get better by doing, so by exercising content creation regularly, you’re building skills and becoming a better artist. Two – your footprint becomes bigger for someone to eventually find your stuff and dig what you’re doing. When I was doing YouTube, the tutorial that got the most traction was slow, deliberate, went through the chords step by step, and I got a huge response for that. So my next videos I was able to learn and build from there. The more content you make, the more opportunities you have to find what works. Three – you’ll be able to develop more of a community if you can commit to regular posts and communication. Do your best to be present and have two-way communication with your fans. Like and comment on other peoples’ posts, ask questions, and really be there for your fans. At the end of the day, we all want to connect on the things with love. If you love your art, it’s so much fun just to share that love with your community through these extra chats.

Before we go, maybe you can tell us a bit about your parents and what you feel was the most impactful thing they did for you?

I have to give it up to my parents for raising me and my 3 siblings, first of all. Having only one child ourselves (shoutout Aurelia!), I can’t imagine raising 4 children, it’s tough enough as it is just being a parent! The most impactful thing my parents did was provide unconditional support for my love of music. I showed interest in my early years, and at 4-5 years old I was enrolled in piano lessons. When I moved to guitar at 10 years old, my parents supported and bought guitars, microphones, recording equipment, and encouraged me to keep it going. Even when I switched majors in college to become a music major, my parents hid their doubts and gave me the confidence to pursue my dreams, which is a lot (especially considering the stereotypical Asian/Filipino parent narrative).

So I’m forever grateful for them seeing me through my journey and supporting me every step of the way. Being a musician requires a lot of confidence through many moments of crippling self-doubt. I carry the confidence that my parents held for me early on, and I bring that strength in each performance I give. As a teacher I try to imbue confidence in my students, reminding them that they’re good at what they do. They’ve trained and practice enough on their piece to succeed when it’s time to perform. And as a parent speaking with my own daughter, the message is the same. I find that with young people especially, once they see that someone believes in them, they tend to work harder and soar higher. And eventually they hold that confidence as their own.

Contact Info:

Image Credits

Main Photo: Alyse Panitz
Upload #2: Craig Chee
Upload #4: Jim Watkins
Upload #5: NAMM Foundation
Upload #6: Diana Halog Sicat
Upload #7: Kala Brand Music

Suggest a Story: BoldJourney is built on recommendations from the community; it’s how we uncover hidden gems,
so if you or someone you know deserves recognition please let us know here.
Resilience
Where do you get your resilience from?

Resilience is often the x-factor that differentiates between mild and wild success. The stories of

Productivity
Beating Burnout

Often the key to having massive impact is the ability to keep going when others

Leadership Development
Finding Your Why

Not knowing why you are going wherever it is that you are going sounds silly,