How discovering tattooing opened the path to a life that felt true

Could you introduce yourself please?

I’m Dylan from LA, 34, and I’ve been tattooing for about 15 years.

How did your tattoo journey start?

It’s a funny story. I was more into music—grew up in a musical family and played guitar, drums, and sang in punk and metal bands. I also drew logos, T-shirts, and flyers for local bands. Then I got into trouble with the law in LA because of stupid friends. I was facing heavy charges, but I got out of it in court. My dad’s best friend, Kirk Alley—a big name in LA tattooing for over 30 years—gave me an ultimatum: if I cut ties with those friends, he’d take me on as an apprentice. He saw something in me. It pulled me out of a bad lifestyle and gave me what I have now.

Wow. Without that, who do you think you’d be?

I wouldn’t have the drive or direction I have now. Tattooing let me meet so many people and travel; it broadened me and matured me. Without it, I might be in a pretty bad position.

Tell me about your apprenticeship. What was the first tattoo you did?

As an apprentice I cleaned, set up, and sterilized equipment (they were medical-grade steel, so reusable). My first tattoo was on myself. After over a year of apprenticing I was asked, “Want to do a tattoo?” I said yes, and they said, “On yourself.” I picked a big traditional rose—total disaster. My hands shook, it hurt, took 4–5 hours, and healed terribly. I keep it as a reminder of where I started. Tattooing yourself teaches pressure and depth. I tattooed myself about five times, then moved on to friends.

Do people still learn by tattooing themselves?

Maybe not as much now. Back in the day most did it at least a few times. If you mess up your own tattoo, it’s on you—and you learn a lot.

What was your first tattoo as a client?

At 17 I got a lotus outline on my shoulder for $10 from someone tattooing out of an apartment—awful. At 18 I went to a proper shop and covered it. Since I was apprenticing, I watched, asked questions, and the artist became a friend who helped me. I think a first tattoo should be a good size. Tiny pieces can make people think tattoos don’t hurt. Bigger work makes pain part of the experience—you earn something beautiful. It tests your will and feels a bit sacred.

When you first got tattooed at 17, had you started apprenticing?

It was just before I started, and I didn’t yet know what real tattooing should be. Once I started apprenticing, I learned fast.

That ultimatum switched your path, right?

Exactly. He said, “If you stay away from them, I’ll help you.” Getting arrested because of their actions was a wake-up call. I needed to change and focus—on tattooing.

When did you fully commit ?

Near the end of about three years of apprenticing. I split with my first mentor and continued under someone else, also learning from tattooers who worked on me. The more I learned about history and craft, the more I knew this was it. I worked full-time day jobs, then drew and painted designs until 2–3 a.m., slept a few hours, and repeated. I tattooed friends at home because there weren’t many studios, and it was still taboo—nobody wanted to hire someone that new.

What’s the happiest moment in your process?

When ideas click in the first consult; the conversations while tattooing; and that first look in the mirror—their face lights up. Running into clients later who proudly show their piece was also amazing. That happened in Bangkok recently.

This is my personal question. If I wanted a small “stamp” to remember this moment in life, how would we approach it?

We’d talk through imagery you’d want to wear for life. Size sets the amount of detail, so I’d design within that. I believe “less is more.” Over 15 years I’ve seen that openness ages better. We’d find the middle ground between your wish and what’s achievable.

What’s the simplest and the craziest tattoo you’ve done?

The simplest one I’ve ever done was just a single dot on a young client’s arm. He said he got the idea from an episode of Friends, where a character gets scared and ends up only getting a dot. I explained beforehand that the shop’s minimum charge was around 80 dollars, but both he and his parents agreed, so I went ahead with it. The craziest was on Memorial Day at Midtown Tattoo in LA. A group walked in—one guy lost a bet and wanted a cartoon tooth wearing Ray-Bans brushing itself with a giant toothbrush… on his butt. It was such a strange and funny piece that I still regret not taking a photo of it.

What’s the toughest part of your job?

It’s physically and mentally demanding. You focus for hours, manage pain, keep people comfortable. Memorial tattoos can be emotional; I’m sensitive, so it stays with me. On rare occasions someone isn’t satisfied, and that hurts. You can’t please everyone, and accepting that is hard.

What do you love about tattooing?

I love tattoos because it’s self-expression and freedom. From tribal and Japanese to American traditional and geometry, you wear what you love. I come from traditional American roots and love the imagery, the machines, and the craft. I keep those core values while modernizing.

How do you choose tattoos for yourself?

I used to map out every concept before getting tattooed.These days, it feels more like collecting work from artists I admire. I remember exactly who tattooed each piece and what happened that day. A lot of people now put heavy emphasis on “meaning,” but I believe the meaning comes from who you choose. The experience itself is what gives the tattoo its value.

Why do people lean more on concepts now?

People overthink and want a clear purpose. If you’re unsure, research the artist—find the style and quality you want, then give them freedom. If you tie them down, you won’t get their full potential.

About Tokyo—what does it mean to you?

For me, this city feels almost magical. Its history, culture, people, and the beautiful simplicity of everyday life always move me. The sense of order and mutual respect here is also deeply impressive. I’m especially inspired by how many people give 100% to what they truly love. Some are so passionate about manga or country music that they spend over twenty years building a bar around that love. That kind of devotion really resonates with how I feel about tattooing. In Japan, tattoos can still carry negative associations—like the yakuza image—but I enjoy being able to share a different perspective through conversation.

What are your goals?

Keep my tradition and ideology alive, travel and meet like-minded people, share moments. I plan to stay based in Thailand; I’ve got a five-year visa. My purpose is simple: keep creating and maintain good relationships.

How do you keep developing your technique and style as you look toward the future?

Each year I review my body of work and adjust for efficiency and evolution. Lately I’ve stripped things down—designing for strength and longevity over decades, simpler compositions, clearer focus. I’m also painting; aiming for 30 pieces this year, with 15 plus two big ones done.

What’s the blue piece behind you? Looks like a poster.

It’s a back-piece concept. I’ll make prints and can ship to Japan. I’m planning a show in Chiang Mai at the end of the year. Maybe I can bring them to Tokyo too.

Do you have any advice for your younger self or newcomers?

Listen to advice and don’t cut corners. Some skip apprenticeships or go to “tattoo schools” that claim to teach you in six months—you won’t get fundamentals or appreciation. Study under a mentor, earn everything, give it your all. Do it the right way or don’t. It may sound harsh, but this craft isn’t to be taken lightly. Learn under someone passionate, and you’ll gain deeper understanding and respect.

Do you feel the younger generation tends to avoid that process?

Yes. These days, a lot of people struggle with criticism or want quick results right away. But when you jump into a field without really understanding the basics or showing respect, it becomes easy to forget the people who paved the way before us.

I see. That makes perfect sense.Before we wrap up, could you share a message you’d like to send out to the world?

Respect people, show love, and appreciate the little things. Don’t take anything for granted, and you’ll be happy.