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“Writing leads me to meaning greater than I started with.”-Bowen Dwelle
I met Bowen Dwelle through the paragliding scene last summer. He camped at my place for a few days in his conversion van to fly nearby Woodrat Mountain. It rained a lot during his visit, but he used the down time well–working on his life-coaching website, writing, and planning his next destination.
He wasn’t always this footloose. A San Francisco native, he worked for an early tech-company and then he started and ran a company called AdMonsters for 15 years. A “creative-in-residence” at The Battery in San Francisco, he is currently working on a memoir. He also offers life-coaching through his Second Sight Coaching (tagline: “Your intuition needs you”). The website for this new venture is well worth a visit, featuring a reading list, podcasts, useful blog posts, and a list of Bowen’s upcoming workshops and appearances.
Our conversations wound around themes of writing, alcohol-abuse, living on-the-road and writing. I was thrilled when he said he’d join us for the Tim Cahill writing workshop in Yelapa, Mexico. Here is an interview I did with Bowen a couple of weeks before our departure.
DEEP TRAVEL: Tell me about your journey with writing? How did you realize it was a good medium of expression for you?
BOWEN DWELLE: I was better with words than with people until very recently, and I devoured sci-fi in my early teens. Ursula K LeGuin was one of the first to show me how evocative lyrical prose can be, and Jenny Holzer turned me on to the power of just a few words; writing as an arrow to the heart, a sentence as a spell that can cast itself in stone. I also loved travel and adventure writing; classics like Bruce Chatwin’s In Patagonia and Bernard Motissier’s The Long Way are part of my foundation. Reading work like that, and writing for classes in high school, my fourteen-year-old self had a clear image of becoming a writer in my fifties. I knew that it was something I’d come to later in life. I journaled about that back then, and also shared that vision with a friend of my mother’s who was like an aunt—and then buried it so deep that I forgot who I wanted to be and even claimed that I had never known. It wasn’t until my intuition began to come to me as text messages that I began to remember myself as a writer. My intuition eventually led me back to my purpose. 
DEEP TRAVEL: What writing goals do you currently have?
BOWEN DWELLE: I‘m working on a memoir that connects my own coming of age in San Francisco with relationship stories (is there a word like schadenfreude for pleasure derived from our own misfortune?) and some hard-won life lessons. The book might be called Spin the Bottle. 
DEEP TRAVEL: You have a distinctive writing voice. I remember you once telling me you preferred music in minor keys. I feel like your writing has that same flavor: raw, gritty, vulnerable–unafraid to veer into dark places. What role does writing play in the way you process and understand your emotions?
BOWEN DWELLE: It’s true that I’m no Paul Simon fan. I used to wonder what the hell people meant when they talked about “processing” emotions. Based on my own experience, I would say that if you’re out there wondering how to process your emotions, all you need to do (as if this were easy) is to express yourself. Find a way to say/shout/sing/paint/bang/dance what your inner self really wants to say. Use whatever language comes naturally. If you don’t have any words, cry, yell, stomp your feet. Don’t hold back. It takes some practice. For me, writing leads me to meaning greater than I started with. I don’t think art appears fully formed. Emotions are where we start; expression is the process; a greater sense of self is the result. That’s what art is: a projection of self—which certainly makes it easier to see than if it’s all locked up inside your head! 
 DEEP TRAVEL: You talk about “flow” a lot–whether it’s with sports or a phase you had when you were into finding the perfect product when shopping.  Do you find flow in writing? What circumstances get you into that state in writing?
BOWEN DWELLE: One way our man Mihaly Csikszentmihalyi defined flow is “when a person’s body or mind is stretched to its limits in a voluntary effort to accomplish something difficult and worthwhile”. With reference to your previous question, he also wrote that “a painting is not just a picture, but a ‘thought machine’” that includes a painter’s emotions, hopes, and ideas.
Writing is the same, and I certainly do find it immersive and challenging enough to get me into flow. To get into that state I need to be well rested, clear-headed, undistracted, and inspired by a specific line of thinking, situation, or bit of language that I’m wanting to explore further. I can tell I’m there when the words start to line up ahead of my hands, just waiting to get out, and I lose myself in the creative process.
Flow is actually our natural human condition; the state of being that we would normally find ourselves in most of our waking hours, had we not constructed such a safe and unchallenging world for ourselves. This is the courage of the athlete, the adventurer, the artist: to leave the nest and choose to do something new, something difficult, something unsafe—those are the things that make us feel normal and sane. 
 DEEP TRAVEL: There are a couple bits of wisdom you live by. One is Turn left three times. First explain that, and then I challenge you to apply it to the writing process.
BOWEN DWELLE: Yeah, that was one of the messages I got early on. It’s my shorthand for ‘take the road less traveled’. Basically, if I hear of a place before I get there from more than one person, I start to develop an aversion. I have a deep suspicion of crowds. I do literally practice TLTT when exploring new places; people naturally default to their (more commonly) dominant right side, so turning left is less common. Applied to writing, it reminds me of what Jack Grapes calls the “transformation line” in his great book Method Writing. His guidance is to always take the “Slauson cutoff”, the unexpected turn. If I hide the salt shaker, I should look at what else I’m hiding from others (and myself). It’s a specific writing tactic, and it’s also a reminder of another truth that I sum up as Fear is Just a Message. Fear is the X that says “dig here”. Especially in our work as writers and artists, if we sense fear, we must turn towards it and inquire. That’s where the truth lies.  
DEEP TRAVEL: The other thing I loved is “be informed but not perfectly informed.” This feels so applicable to travel!! Do you want to elaborate on that a bit?
BOWEN DWELLE: That one has since evolved into “Just Ready Enough”. It’s impossible to be 100% ready, and once we get to about 83%, getting any more ready will not only take more time than simply doing whatever we are getting ready for, it will often actually prevent us from experiencing that. Being over-prepared constrains the possible results of our actions. Does a writer choose the words she is going to use before starting to write? The language, yes, the pen, the paper, the laptop, the writing app, the subject, but not each word. That is the act of writing itself. The same applies to anything else. If we plan every stop, every sight, every night’s stay before we embark on a trip, we might as well stay home! Nothing is going to happen! Nassim Taleb writes a lot about freedom and options in his great book Antifragile—in short, freedom is having options. Being prepared creates options, but being over-prepared destroys them. Perhaps one way to tell if you are just ready enough is if you feel that you have multiple options, and you can see them all as possible (not just in theory, but actually possible). Being just ready enough creates the preconditions for intuitive action. Making the right action at the right time from options that you have created is nothing short of victory itself. 
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“Flow is actually our natural human condition; the state of being that we would normally find ourselves in most of our waking hours, had we not constructed such a safe and unchallenging world for ourselves. This is the courage of the athlete, the adventurer, the artist: to leave the nest and choose to do something new, something difficult, something unsafe—those are the things that make us feel normal and sane.” –Bowen Dwelle
DEEP TRAVEL: You’ve recently ventured into life coaching with your Second Sight Coaching. Tell us more about that and how that is going.
BOWEN DWELLE: At a certain age in California, we all become coaches, therapists, and yoga teachers. I’ve been a leader, teacher, advisor, and consultant all my life, but I wasn’t inspired to consider becoming a coach until I stopped drinking—and started writing. As I found my way to greater self-expression, I began to see from own experience how much personal change is possible, and people began to ask me about my experiences as an entrepreneur, as a leader, as an athlete, and about my experiences with anxiety and depression, with alcohol, with my intuition. Coaching is also great as an externally-focused complement to the inward process of writing. I love working with others to help them choose freedom, whether by learning to know and trust their intuition, changing their relationship with alcohol, or escaping the machine through entrepreneurship. 

DEEP TRAVEL: I gather that intuition has become the key to your kingdom. Tell us why intuition is so important to you. 

BOWEN DWELLE: I’ve come to believe that intuition is our most underdeveloped and undervalued human ability. Intuition is the voice of you—and of the universe. Intuition is pattern recognition, and the recognition of the patterns of the natural world reflected in the patterns of our thoughts and emotions. Intuition is the unconscious becoming conscious; knowing without knowing how. Decision-making is cognitively expensive, and not super fun. Often described as embodied cognition, intuition not only feels good, it’s a hell of a lot easier on the brain. Intuition is the spark of creativity itself, and it’s the voice (and the only voice) that will speak your purpose (What else will? Certainly not some “what am I here for?” worksheet). Intuition is also what keeps you from fucking up your life. The good news is that if it’s working, you pretty much can’t. Like anything else, you get good at what you do, and the same is true for intuition: the more you use it, the better it gets. So, yeah, I pay serious attention when it speaks up, which is pretty much all the time. I now see my conscious mind as riding along on top of, but in service to, my intuition. Decide Nothing! 
DEEP TRAVEL: What writing goals do you currently have?
BOWEN DWELLE:  I’m working on a memoir that begins with my personal story of surviving youth San Francisco in the 80’s and emerging from an early life of drinking, drugs and depression through my discovery of how to reconnect with intuition and creativity. The book might be called Spin the Bottle, because that’s what I missed out on by skipping fifth grade, which is what started all of my troubles. 
DEEP TRAVEL: We are looking forward to hearing more about your book when we see you in our Yelapa writing group soon! Thanks Bowen!
Visit Bowen’s website at
Visit Bowen’s Second Sight coaching page at
For more information about Deep Travel Workshops, visit or email
DT Paris 2020 Flyer Final2
There are three spots left for our workshop in Paris April 4-10th, 2020.

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