"Take Simple Things to Extreme Lengths: My Tattoo Story"
Hey, WeWill Readers!
This week's newsletter takes a slightly different direction. Instead of tackling a skill I'm developing or a concept I'm exploring, I'm sharing something more personal: the story behind my first tattoo.
It's a journey I've wanted to document for myself for quite some time, and I figured, why not bring you along for the ride? No productivity hacks or philosophical deep dives today, just a story about turning meaningful ideas into permanent art.
Hope you enjoy this little side adventure from about two years ago!
September 2022:
So I knew I wanted a tattoo for years. I assumed the perfect idea would magically hit me one day, fully formed and ready for ink. But we all know: that's not how it works.
After months of telling my friend Hendrik that "I'll know it when I see it," he finally laid out some hard truth: I'd never get my tattoo by just waiting around. He made it clear I needed to follow certain steps:
know what I want,
research styles until I find exactly what resonates,
and find an artist whose work I love.
I knew my tattoo had to be timeless, something I'd identify with now and decades from now. It had to have meaning, not just the looks.
CrossFit and fitness have been constants in my life, a fundamental belief that a healthy body is key to a good life. So I knew health and fitness would be central themes.
During my search for the perfect idea, I thought about Aaron Horschig's book "Rebuilding Milo" a comprehensive guide for athletes that provides rehabilitation techniques and training principles. It had become my go-to reference for injuries, aches, and understanding how my body functions. I always loved the cover art of the book: a sketch-style silhouette of a man performing a perfect squat, holding a barbell on his shoulders.
This was my starting point. I imported that silhouette into Photoshop and started experimenting. I removed the barbell and tried adding other elements, a surfboard, mountains, but nothing clicked.
My first tattoo draft.
While playing with the book, I reread its introduction and discovered the legend of Milo of Croton, an ancient Greek Olympian who began his strength journey by lifting a small calf daily. As the calf grew into a bull, Milo's strength grew proportionally. This perfectly illustrates progressive overload, how consistent effort leads to extraordinary results.
The legend resonated deeply. I wanted to become my own version of Milo, a journey I'm still committed to every day. Luckily, the book included illustrations of both young Milo and adult Milo. To show this progression, I drew a coordinate system, placing young Milo at the beginning and adult Milo further along (side fact: this represented my engineering background). The final element was my personal mantra: "Take simple things to extreme lengths."
BOOM, what do you think? Not too shabby for a draft eh?
Now I had a concrete vision, but how would I turn this into a tattoo? For years, I'd been very selective about tattoos, believing only a tiny fraction were truly good. I always said my tattoo would need meaning and be artistically exceptional.
So to recap Hendrik's process: know what you want (✅), research extensively, and find the right artist. It was time to actively search for someone who could bring my vision to life.
Over two months, I immersed myself in tattoo content on Instagram. My feed transformed into an endless stream of tattoo styles. I gradually realized I was drawn to geometric shapes combined with organic elements.
Then one day, Seraphim appeared in my feed. One tattoo immediately caught my attention, I knew instantly this was special. I explored his profile and fell in love with nearly everything.
Sera’s instgram profile.
I'd found my tattoo artist! I found a Greek artist based in Athens who could bring my ancient Greek tale to life. How perfectly fitting is that?
I reached out to Seraphim, describing my idea, thoughts, and feelings. I asked him to consider everything and transform it into art in his style. After a few weeks, he outlined his plan:
"Hello Dustin! I want to make one surrealistic bull cut in 3 parts. Every part will be bigger than the previous and I will add a small silhouette of a man holding the whole design. I will of course use some geometric elements for my composition and the phrase you suggested! You will see the design on the day of our appointment."
Wait! He wanted me to wait until our appointment to see the design for the first time?! This meant flying to Athens with only 10 minutes to decide whether I liked it or not. While I trusted Seraphim's talent, I worried I'd go insane imagining possibilities during the four-month wait. But after his explanation that he wanted to provide his best work, I agreed.
Fast forward four months. On May 5th, I sat outside his Athens tattoo shop, barely containing my nerves. I promised myself that if I didn't love the design, I wouldn't go through with it. period.
I walked into the studio and after a quick chat, Seraphim turned his monitor toward me, saying, "And this is the design I came up with." I barely heard his words as a tsunami of thoughts flooded my mind. The design was so different from what I'd imagined. Though I knew it would differ, my mind had created hundreds of possibilities during those four months, and this wasn't close to any of them.
The surrealistic bull had become a REAL bull chopped into three pieces. Milo had transformed into a man-shaped muscle skeleton. My timeline had become a simple "-1, 0, and 1".
Seeing the artwork for the first time!
While these thoughts raced through my head, Seraphim explained his intention behind every detail. I couldn't focus the first time, so I asked him to repeat everything. He realized I was having an internal battle and patiently walked me through it all again.
This gave me space to zoom out and ask myself:
Do I dig the art he made? Hell yes!
Does it represent everything I wanted? No doubt about that.
Is there any element I might regret inking? Hmm, the bull's head looks a bit too large.
We made a minor adjustment to the bull's head size and then proceeded. One sitting, six hours of moderate pain, good conversation mixed with comfortable silence, and watching a true artist do what he loves, that's how my first tattoo came to be.
And I loved it. I still do.
Your Tattoo Blueprint
If you've been thinking about getting inked, don't make my mistake of waiting for inspiration to magically arrive.
Instead:
Define your core idea - What concept or story matters enough to carry forever? Is it meaningful enough to ensure you won't regret it years later?
Research until your algorithm knows - Immerse yourself in styles until you discover what truly resonates. Let your digital feeds become your research assistants.
Find an artist who's 95%+ perfect - Don't settle for "good enough." Look for someone whose work consistently makes you think "Holy crap, that's incredible!"
Trust the creative process - Communicate your vision clearly, then give your artist the freedom to translate it through their unique lens.
Be open but clear - Have your non-negotiables ready for the reveal, but leave room for artistic interpretation and surprise.
Why It Matters
Two years later, my tattoo remains a daily reminder of my commitment to progressive growth. It's not just ink, it's my philosophy made visible, a conversation starter, and a permanent part of my identity.
What story are you carrying that deserves to be made visible? What concept guides your life? Let me know in the comments!
