When I was a teenager, I dreamed of becoming a rock star, an acclaimed fiction writer, and a famous abstract painter. As I grew older, it was to become an actor, a screenwriter, a Hollywood director, a celebrity chef. Then, in my thirties, I fantasized about training to become a yoga instructor and hosting spectacular retreats on the beaches of Costa Rica. (I still hang onto this one!)

To be truthful, I’ve day dreamed a heck of a lot about who I wanted to be or what I would become when I got older.

It actually kind of sucks to think about how much I wanted to become something but just could never muster the vision, courage, or determination to actually make that something happen. Even though I have had some nice, even noteworthy, career successes and my share of remarkable and transformative experiences in life—not always good but uniquely powerful, nonetheless—I’ve never felt like one of those lucky people who knew exactly what path to pursue in life and wound up living their dream.

I’ve been living, just not living my dream.

And yet, one thing has remained constant. I have never stopped believing that something brilliant would unfold for me one day.

It’s funny when I think about it, the small signs along the way that something was about to shift. Ever since my kids’ mother died six years ago after giving birth to our third child, Satya, I’ve always wanted to get a tattoo. She had a small one on her back, and it always intrigued me. So finally, after years of waiting and random excuses, I pulled the trigger last spring. Within a week, I had made an appointment with a talented tattoo artist and was soon explaining to him that I wanted a rather large first tattoo—a three-quarter water motif sleeve with three Koi fish circling my arm and a lotus on my shoulder radiating light from within. Without question, aquatic environments have always helped me feel peaceful, free, and truly joyful—more so than anywhere on land. This tattoo, I decided, seemed to represent that dream of being closer to the water.

At about the same time as my numerous sittings under the needle, I joined up with some friends and peers on a boat tour of the new Bay Bridge in San Francisco. As we rocked back and forth on the water, the guide explained to the group how this architectural marvel, a gleaming, soaring white bridge, was decades in the making and cost billions of dollars to complete. He described the architect’s vision of a modern, single suspension bridge, one that would offer sweeping views of the Bay to motorists as well as to cyclists on a new bike lane—something that the old bridge never had. And for an iconic metropolis on the water that boasts a vibrant, almost fervent bike culture and is the birthplace of mountain biking, this is a very, very big deal.

Only one problem, he shared. The bike lane won’t actually open to cyclists until 2015, and it will stop half way across the Bay at Treasure Island. To actually get bikers into San Francisco (or back to cities like Oakland and Berkeley in the East Bay) will take at least another decade and $500 million to retrofit the western span of the bridge.

That’s when it began.


The tiniest spark of an idea that I could instantly feel rooting itself into my being as I looked to the east at the port of Oakland and Berkeley hills…then to the west across the Bay at the San Francisco skyline.

No bike lane on old bridge. No bike lane on new bridge. That means one thing: not a single person in history has EVER biked across the Bay.

What?! Could that be for real? Let’s think about this for a second, I said to myself. Of course bike commuters somehow got into the city everyday. That’s a fact. So how? Well, they are able to ride the ferry or squeeze onto packed BART trains, but that’s definitely not biking; that’s sitting. Within seconds, I began to visualize someone riding their bike from their house down to the water’s edge. They’d get onto some device or pontoon boat or something, pedal across the water to the other side, and then get off and bike the rest of the way to work.

That was it. I could see it all unfolding. At that moment, I heard my inner voice say: If nobody has actually done this, I will be the first person to try. It became my singular obsession for the next four months.

In all honesty, I’ve never been the mechanical type, or a bike expert for that matter. While I love biking, my experience tinkering with bikes went as far as raising the seat and installing a bottle holder. Within a couple months, our kitchen was turned into a cluttered mess of bike frames, wrenches, screws, bolts, and grease. Sometimes, being a single father has its benefits, because only a few moms would have put up with this mess. My eleven-year-old daughter, Naomi, was a good sport, but by the end of the summer, I could tell she had had enough.

Fast forward to the morning of September 27, 2013 when I set a new world record by becoming the first person in history to bike across the San Francisco Bay.

It was a truly epic and beautiful bike ride, one that left me deeply humbled and grateful. One week later, I did the same thing biking across the Hudson River for the first time ever from Hoboken, New Jersey to a Manhattan dock crowded with reporters (see the CBS Evening News report below!). I’ve also launched BayCycle Project, which aims to build a new aquatic frontier in biking. I’m also starting a crowd-funding campaign on Kickstarter to design the water bike craft of the future—one that will enable all cyclists to easily ride their own bikes on the water for sport, recreation, health, and transportation. And on a planet that is two-thirds water with over five billion bikes in circulation around the globe, this seems to be a long time coming. It also feels like, at long last, my dream has come into focus. Not what I expected or ever envisioned, but something that is so brilliantly and perfectly suited to me—a life biking on the water and showing other people the joy of doing the same.

Sometimes having belief in your future, even without the clear and stated intention or purpose, is enough to manifest the life you always wanted but could never express with words.

What do you secretly love without the attachment of it becoming something?

There was a great “mockumentary” about mermaids on television last spring that had me wondering, wishing that I had aquatic ancestors! For me, I’ve always secretly loved the idea of a life on the water but never associated it with a career or a life mission. I never actually held it out as something to attain or become, rather I only came up with a thousand excuses not to take steps towards achieving.

How strong is your belief in amazing?
(Click to Tweet!)

We can always find reasons to doubt that our lives can’t possibly change overnight. Stuck in a career, bills to pay, kids to raise, unhealthy relationships, no time, and of course, don’t know what to do…Trust me, I’m no different than anyone and know all the major life issues at forty-one! What would it take to just start believing with heart, mind, and soul that YOU are destined for amazing?

What If?

We live in a world of radical transformation. Every day, new ideas are coming to life that literally transform the way we live, learn, and play. They all started with someone asking “what if?” What if you could make money renting out your apartment for a night? What if you could skip the long taxi line and order a car from your phone? What if people could drink amazingly healthy fruit drinks from the rainforest and help support local economies? You don’t have to be an expert or have a degree in anything to ask those kinds of questions and make them a reality. All you have to do is look around and ask the question “what if?”

Here’s me featured on CBS Nightly News…pedaling on water!

Judah Schiller is the Founder of BayCycle, Inc. and the CEO/Founder of AIKO, a design and innovation agency focused on transforming the way people live, learn, and play. Launched on the heels of becoming the first person in history to ever ride a bike across the San Francisco Bay and the Hudson River, BayCycle is dedicated to building an aquatic frontier in biking for sport, recreation, health, and transportation. It’s mission is to enable the world’s five billion bikes for riding on the water. Judah lives in Mill Valley, CA with his three awesome kids and naturally loves being by the water. Learn more about Judah and BayCycle on Facebook and Twitter.