Fear, Flow and Freedom

Fear and flow are inseparable. Flow requires just the right amount of fear, and that fear guides us toward the door to flow. Flow in turn is the path to freedom — and so, to get more free, we must turn towards our fears.


Fear is a message that we often misinterpret — and it’s nothing to be afraid of. Most often it’s fear of the unknown, of randomness, our fear of fear itself. We become afraid that our fear might be a signal of serious risk, and the very idea makes us turn away. Fear is a finely tuned signal that we can learn to interpret. So, first of all, know that fear is just a message, give up being afraid of fear, and listen to what it’s telling you.

We should hear fear whispering “be very afraid” as “look right here. Instead of turning away from fear we should peer directly at its source. Like any other emotion, fear wants to win, and when we turn away we give fear the upper hand. If most of all we fear the unknown, then turning away from that which we feel fear of does nothing to resolve the fear. Furthermore, anxiety is exacerbated by avoidance — we strengthen the neural pathway laid down by turning away from the subject of our fear (or fear itself), and so we reinforce the tendency to turn away.

Our fear of risk has become overdeveloped. In the modern world, fear is rarely a signal of a major threat. The more we can come to be at home with some fear in the house, with some risk, the more we can navigate the world the freedom of creative flow.

“We’re hard-wired to enjoy risk [because] there we can still be both confident in our experience and confronting the chaos that helps us develop.” — Jordan Peterson

How much risk should we become comfortable with? We can find the answer by looking further at flow.


When we are in flow we are our most creative, most satisfied, and most human. To find flow we need nothing more or less than an achievable challenge. We need a touch of fear and a glimpse of the light at the end of the tunnel. We need to approach — but not dive far beyond — the edge of our possible. Flow is blocked just as much by the terror of the impossible as it is by the sure thing.

My own shorthand for the right balance of achievable vs challenge, and therefore of ideal risk, is 83%. 83% of what? 83% of what might be achievable. Why 83%? First of all, if we aim for 100% of what just might be achievable, it’s more likely than not that we will fail, and quite likely that we will suffer for the attempt. Not that we shouldn’t suffer, but if we are aiming for flow, we want to have a reasonably good chance of success, with some challenge along the way. This guides me to aim for something like 80% of what just might be achievable — but then 80% just seems a little low. We want enough challenge so that each time we do succeed, we push a bit farther into the unknown. So: I like to shoot for 83% of maybe.

To come to know flow better and to push towards fear, we need to consider our preparation. We are all the captain of our own ship. Our experience will be dictated by what we have prepared ourselves for. To have a good possibility of achieving any goal, we need to be just ready enough to enjoy a reasonably good possibility of achieving our goal. We need to be as prepared as we can be without being over-prepared. We need our tools at hand, but we don’t want to trip over the tool belt. Being over-prepared uses up valuable time (before we’ve even started) and blocks the possibility of finding spontaneous, creative solutions that we would not be ‘forced’ to find had we prepared for every eventuality that we could imagine. Therein lies this paradoxical truth: we can’t imagine every eventuality, and so it’s impossible to be 100% prepared, and being 100% prepared boxes us into the set of possibilities created by the eventualities that we’ve imagined.

Being prepared is just one part of being ready — we have to leave space for creativity. Preparation is the workshop where the magic of innovation is made. Each requires the other. Here again, 83% is a handy guideline. I aim to be 83% prepared, and ‘save’ the 17% for creative solutions in the moment.

“This is the central illusion in life: that randomness is risky, that it is a bad thing — and that eliminating randomness is done by eliminating randomness.” — Nassim Taleb

If we prepare ourselves to be led, we will follow. Part of our own individual preparation should be to create the opportunity for the challenge that we need — and we can do this even without knowing exactly what that challenge may be! All that is required to create the opportunity is to set a goal. If you don’t know what your goal should be, pay attention to what you don’t want to do. Look closely at recurring messages, especially those that you shy away from, the things that you say “maybe next time”, “if only”, “I wish” about. A goal can be – and always is – a stepping stone. Set the first goal and let it lead you to the next. You don’t need to know where the path is leading, only to set goals that you will be sure of having achieved (or not).

Find a small fear and turn it into a target. Approaching fear is always a challenge. More than anything else, we are afraid of the unfamiliar, and if we rarely meet fear, we will be afraid of fear itself. Turn fear into a familiar friend and we can see where fear is pointing us more clearly. Then, knowing that you are ready enough, you can let the circumstances of the moment lead you. How to “face your fears”? Listen to your fear, use it to set a goal, prepare, and then be in the moment.

Once we have prepared and set a goal, we are free to flow into and through our experience. Flow is the feeling of not trying, of not deciding — flow is using your preparation, your skills, your body as they naturally come together in the moment as you move towards your goal. Flow is moving, acting, being intuitively — and therefore being in flow trains our intuition. Like any other skill, intuition improves with use, and being in flow is the best way to build the intuitive muscle.

Intuition is the wellspring of creativity, and creativity is both the expression of freedom and what is required most of all to become free. Thus in turning towards our fears and preparing ourselves to be in flow, we train our intuition, opening the door to greater creativity and to freedom.


Choose Freedom


Kitesurfing Adventure Skills is a unique program that I developed and led for the first time in 2018 on Brazil’s incredible northern coast. This program combines an intensive week-long long distance kitesurfing clinic with personal and leadership development. Much more than just a kite trip, we incorporate meditation, physical fitness, adventure and leadership skills, and integrated life skills: how to find and choose freedom and harness flow as a gateway to adventure.

Kitesurfing Adventure Skills Dec 2018 

I love language as an art form and t-shirts are a great medium. My second series of shirts is available here, and series 3 is coming soon!

WATCH THIS shirt from series two


I’m a brand ambassador, guide, and advisor for SurfinSemFimthe leading kitesurfing adventure travel company in Brazil and South America. SSF is affiliated with egroup hotels, which include the incredible Rancho do Peixe and Vila Kalongo.

I’ve been flying the beautiful, elegant and highly functional Boardriding Maui Cloud kites since they were introduced in 2013, and I’m a team rider and founder of the Cloudriders facebook group, a passionate and very active community.

EO, the Entrepreneurs Organization is a global nonprofit network of entrepreneurs whose mission is to engage leading entrepreneurs to learn and grow. I joined EO in 2009 and have served in various leadership roles including chapter president of EO San Francisco, at the global committee level, and as founder of Flow Forum.

The Battery – founded in 2014, the Battery is a social club in San Francisco. I joined as a member and in 2018 was invited to become a Creative/Athlete in Residence. I am one of the co-founders of the Battery Adventure Club.

Alpinefoil team rider • REVL investor and team rider • Kurtis Eyewear team rider

Business and Entrepreneurship

My earliest work experience was delivering the SF Chronicle around the neighborhood. Even at that age, we had to buy the papers from the distributor, manage our own subscriptions, and collect the dough. I started my first company at age nine with my buddy Zack, we sold D&D books and dice to the other kids at school and I worked after school at age ten coding in dBaseIII.

From there I eventually found my way to an early career in software, and then in online media at WIRED in the late 90’s, during which time I started what became my first company, AdMonsters. After a long and winding road and many many conferences, I successfully sold AdMonsters to Access Intelligence in 2015. I continue to think and work as an advisor, investor, and entrepreneur. Entrepreneurship has been a key part of my own path to freedom. It’s hard to get outside if you’re in the office – join us, choose freedom!

Expertise and Subjects

Here are some of the topics that I have experience with, speak and write about, and enjoy discussing.

KitesurfingParagliding • Trail Running • Hydrofoils • Outdoor Sports

AdventureAdventure Travel • Geography • Languages

Entrepreneurship • FreedomIntuitionFlow

Community • Connection • Conferences • Designed Experiences

WritingLanguage • Branding • Communication 

YouthDepressionAlcohol and Drugs

I’m a proud San Francisco native and have lived all over the city, in particular in Noe Valley, the Mission, Potrero Hill, the Panhandle, North Beach, and now in Sausalito. I went to Alvarado, Nueva, Everett, Lowell, McAteer, and graduated from UC Berkeley with a major in Geography.

There’s a reason the pioneers went west, and that California is called the Golden State. A passionate Californio, I’ve explored this beautiful place all my live, and while I know it intimately, I continue to discover new places here all the time.

I first discovered Brazil on a trip in 2008 and have been there perhaps ten times since then. Brazil is roughly similar to the U.S. in scale, population, and diversity of landscapes – and the most diverse country I’ve ever spent time in, with a warm, welcoming, curious, fun, active and vibrant culture. I love Brazil and now have many friends there, and I feel lucky to spend a month or more there most years.


– Bowen