Always Go a Little Further Into the Water

David Robert Jones
If you feel safe in the area you’re working in, you’re not working in the right area. Always go a little further into the water than you feel you’re capable of being in. Go a little bit out of your depth. And when you don’t feel that your feet are quite touching the bottom, you’re just about in the right place to do something exciting.
David Bowie

David Robert Jones started his career by inventing himself. Being named Davy Jones worked just fine until an American band called the Monkees started getting famous for their Diet Beatles hijinks, and at that point, a choice had to be made. Continue on in the shadow of other Davies? Or strike out and create something totally new and unique?

Enter David Bowie.


An Englishman by birth, Bowie seemed from the jump to be infusing himself with America. Even his name was taken from the famous frontiersman’s knife, probably because Davy Crockett was already taken. But more than that, Bowie was infusing himself with change, something America knows well. He was totally unafraid to push himself, musically and spiritually and sexually and personally. More than any public figure, he was completely at ease doing the hardest thing we humans do — changing — to fit his interests and the times. Most impressively, he was always ahead of the curve, like a glam-rock oracle, predicting the way the wind would be blowing and shifting before it could reach him.

With all the tributes pouring in the last few days, I’ve learned more about Bowie than I knew while he was alive. I’d love to say I had an intimate personal connection to his music, but he was always eluding me. My parents were more a Doobie Brothers / Elton John household, so I missed my early chances. And by the time the streaming music fountain we enjoy now came around, I was already overwhelmed with things I hadn’t heard. I mean, I didn’t even see Labyrinth until 2 years ago.

Many times, I’d be watching a movie or be out at a bar and hear a completely unheard thing, a sound that makes you tilt your head and say “what’s this and why do my ears suddenly need it?”. So often, it was a deep cut David Bowie track. Such was his genius that every time this happened — and it happened a lot — I’d be continually impressed, as I’d think it was an artist I had never heard before.

So with all these eloquently penned pieces, one of them — and I honestly can’t remember which one, such is the transient nature of constant Internet browsing — mentioned the quote above. It’s really struck home for me, as this last year building Fittery has been my further into the water moment, pushing myself to do things that are out of my depth, knowing that’s where you get to the exciting things. I haven’t always been that way in life, so I have a sense of pride that I’m channeling a little of my inner Bowie in this way.

Lightning bolt make-up to come shortly.


Like all truly great artists, their work and their lives can help us learn more about ourselves. Besides the hours of fantastic music and performances, Bowie’s courage to continually go a little out of his depth is his gift to me. His persona transformations weren’t for show. He lived to constantly push himself into the deeper water, to find his life and musical inspirations where his feet couldn’t touch. Where you’re in the right place to the exciting things.

Greg Vilines is one of the founders of the startup Fittery. You can find him on Twitter and right here on Medium, posting about startups and pop culture, Hulk-smashed together.