Here Be Dragons podcast on the long distance experience with SurfinSemFim

Did I say podcasting was easy? Not a chance. That said, it is easier than shooting a film! I was lucky enough to be one of the principal athletes in the SurfinSemFim film production last year in Brazil, and believe me, I was glad that my only job was to kitesurf 100+km every day!

I was interviewed on the awesome Here Be Dragons kitesurfing podcast the other day. On his show, Bjoern digs up the details on some of the most interesting kite destinations around the world, and I’ve learned a lot listening to his episodes about South Africa and Chile, to name a couple.

He asked me to be on the show to talk about my #longdistance #kitesurfing experiences in Brazil with Surfin Sem Fim. We did a trans-Atlantic simul-cast and worked our way through the 600km itinerary that we captured last year, talking about the landscape, the spots, the kiting, and the immersive experience of traveling by kite day-after-day down the coast of Brazil.

Thanks to Surfin Sem Fim, Boardriding Maui, Andre Penna, Marco Dalpozzo, Bill Plautz and the #longdistance pioneers like Louis Tapper for the inspiration.

Here’s the link to my episode of the Here Be Dragons podcast – or find it on your favorite podcast app and subscribe! Part 1 is out today, part 2 to follow next week — I hope you enjoy the show.

Adventure Sports Podcast on long distance kitesurfing

I’ve been exploring the world of podcasts lately and this flourishing form of expression is very gratifying and inspiring. To use a model that I also use to describe various sports: writing is simple but difficult. Video is complicated and difficult. Speaking is simple and easy. Maybe radio/podcasting is [somewhat] complicated and yet easy?

In any case, there are podcasts about just about anything you can imagine, and in doing research for my own (!) I came across the Adventure Sports Podcast – and they asked me to be on the show!

Starting with the “beginner questions” about what kitesurfing is and how it works, at about 44:30 we move on to talk about my #longdistance #kitesurfing experience in Brazil and also about the deep connection between athletics and intuition and how being active in nature – especially over the course of a long athletic journey – can be a powerful way to train your intuition.

Thanks to Surfin Sem Fim, Boardriding Maui, Andre Penna, Marco Dalpozzo, Bill Plautz and the #longdistance pioneers like Louis Tapper for the inspiration.

Here’s the link to my episode of the Adventure Sports Podcast – or find it on your favorite podcast app and subscribe!

SurfinSemFim long distance kitesurfing documentary

Early last year my friend Marco mentioned an idea, a project that he was working on. Not ‘just an idea’ as we often say but an awesome idea, and I said yes!, let’s do it, I would love to be part of it if it happens.

I went into training mode – some flying, running, swimming in the Bay and kiting in Cape Town, the Philippines, Micronesia, Baja, and California – and a few months later I found myself in Taiba, Brazil getting ready to kite 600km down the coast with a small film crew to capture the experience.

This sort of athletic journey is my favorite way to travel, and it was an incredible opportunity and a privilege to be one of the six professional athletes that formed the team. I was the only American and the only non-Brazilian on the team, which made for an additional challenge on top of the long days on the water. The other riders were Guilly Brandão, Andre Cintra, Marco Dalpozzo, Andre Penna, and Marcela Witt — a diverse crew of world-class riders, all game for some long distance adventure!

After nearly a year of post-production the resulting film was released in Brazil by Canal OFF and I am now able to share it here with you.

An intense athletic journey is one of the best ways to bring out the connection between athletics and intuition, and making this film was a transformative experience for me. Not only was this my first pro athlete gig but I was also working in a new foreign language (Portuguese). At first it was hard to find my footing but once I got my board under my feet and my kite in the air I felt right at home. I’m very proud of the result and very happy that the film captures the feeling of this incredible part of the world, and of the long distance experience.

Enjoy the film and I’d love to hear your thoughts!


Production: e-group Hotels & Sports | Surfin SEM FIM | Vídeo com Alma
Director: Bruna Arcangelo Toledo
Camera: Mathias LessmannHugo Valente | Bruna Arcangelo Toledo
Script: Bruna Arcangelo Toledo
Editor: Ronaldo Andrade
Sound: Bruno Frene
Executive Producer: Jalila Paulino | Marco Dalpozzo
Supervisor of images: serginho pasqualino
Colorist: David Queiroz
Assistant colorist: Bruno Bridges
Athletes: Guilly Brandão, Andre Cintra, Marco Dalpozzo, Bowen DwelleAndre Penna, and Marcela Witt
My sponsors: Kurtis Eyewear, Alpinefoil kitesurf hydrofoils, and Boardriding Maui Cloud kites!

Series II Shirts

Series Two Shirts are now available

I’ve continued to refine my messages as well as the designs. This series uses a specific typeface that I researched with the help of my old friend Colin Johnston. The mirror-image type design is intended to create a graphic element, and also to present the message equally to the wearer, along with the approaching reader.

These designs are all important messages that I have received, continue to use, and enjoy retransmitting to others. I love language and language-based art, and t-shirts are the best way that I’ve found to share this sort of art with others.

This is an art project. Click the image to be part of the magic


What better way to change (as much as possible) than by aiming to change everything? We all wonder how to change, and I’m no different. I had no idea, except to follow my intuition.

Meeting the current owner of my custom Lamborghini Orange Vespa by chance in San Francisco!
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I’ll Never Forget You

Pay attention: everyone you meet brings something unique to your world. You never know when you’ll meet someone unforgettable.

I’ll never forget the AdMonsters crew
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Keep Odd Hours

I’m sick of all these health nuts telling me to go to bed at the same time every night. All of the interesting things happen in the small hours.

Sex is Better Sober

Right? Right.

I met this complete stranger in the market in DTLA and stopped to compliment her on her outfit. She has nothing to do with the shirt.
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Someday Means Never

Don’t put your dreams a list. How many times have you heard someone – or yourself – say “I’d like to do that someday…” Next time, take that moment as a message and make a plan to do it immediately.

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Watch This

A friend’s kid wanted to watch more of “his show” the other night – I just said, hey kiddo, #WatchThis instead.

Watch This is what you say when you’re confident enough to step out in front – or when you know that something interesting will happen, and happy with whatever the outcome may be. When people ask me: watch what?, I just say keep watching.

click image to purchase
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Call Me Uli

And finally, an old favorite from Series Zero that I’ve revived for this announcement:

click image to purchase

Click here to help retransmit all of these important messages

I’d love to hear from you on Facebook or Instagram, just tag @bowendwelle or #CallMeUli with your photos!

8 Meter Media site relaunched

I returned home from February in Mexico and March in the Philippines full of ideas. I immediately set about rewriting 8 Meter Media site to reflect the projects and priorities that I have under that business.

8 Meter Media logo

Athletic, experiential and Flow events

Unique retreats, meetings, journeys, contests, community building, event production – all with Authentic Physicality built in from day one.

Sports brand marketing, business services and strategy

Brand and product development, marketing strategy, media placement, social media, sponsorship, team development, and global connections for innovative sports, athletic and adventure travel companies.

Conference business advisory consulting

Business strategy, mission/vision/values, growth, profitability, marketing, sponsorship, content development, exit, and everything else you need to make your conference business truly awesome.

Journey planning

Collaboratively developed custom itineraries with local connections from the Genius Network, everywhere. Even if you don’t know where you’re going, we know where you should go.

EO forum, meeting, chapter and retreat events

One-of-a-kind, once-in-a-lifetime, actually cool, actually fun, outdoor-oriented EO events all built around Flow and Authentic Physicality.

Natives reunited in the wild

I made a series of t-shirts last fall to experiment with some design ideas and share some of my personal messages. I’m happy to say that I got a really positive reaction to a bunch of them – and so this February I decided to produce a second series. I showed up here in Mexico City on my way back from Oaxaca and I was surprised and delighted to see that my friends Florian and Nicky were in town. Thx Instagram! We met up for dinner and Florian had the good sense to wear the NATIVE shirt that I gave him when we met in Brazil in November – and so we got to capture a side-by-side of the two versions! I’m wearing NATIVE #2 on the left and he’s wearing NATIVE #1 on the right. Stay tuned for more designs from series 2!

Natives reunited
Natives reunited

Athletics and Intuition

I’ve spent too much time trying to make decisions. And you know what – deciding isn’t really any fun.

I’m always happier when I flow through life using my intuition. I’d really like to be making zero decisions and living intuitively all the time.

“…we are largely better at doing than we are at thinking…”

― Nassim Nicholas Taleb, Antifragile: Things That Gain From Disorder

This led me to ask myself, how do I get better at living intuitively? How do I train my intuition? 

To jump ahead for a moment, the simple answer is: you get better at what you do often. You can train your intuition by acting intuitively, by using your intuition in any way at all really. But I was kind of stuck, I was used to making decisions – or trying to make decisions – and I was out of touch with my intuitive self. I needed something more specific, a usable, understandable technique that would improve my intuition in a noticeable way.

At the same time that I’ve been thinking more about intuition – over last few years – I’ve also become more and more athletic. I was always very active but until recently I didn’t pursue anything with goals or training, or even on much of a regular basis.

“To realize the body’s potential for flow is relatively easy. It does not require special talents or great expenditures of money. Everyone can greatly improve the quality of life by exploring one or more previously ignored dimensions of physical abilities.”

― Mihaly Csikszentmihalyi, Flow: The Psychology of Happiness

And here’s the thing: once I started being more athletic, I started to notice an improvement in my intuition. The more time I spent doing things with my body, especially authentic physical activities that get me into flow, the more I noticed this effect of improved intuition. I started to think about what the connection is between athletics and intuition – how does being athletic improve our intuition?

This is the answer that I’ve come to: When you’re engaged in authentic physical activity (especially outside), your body is responding automatically – intuitively – to the environment, to the situation as it comes. As you practice this intuitive movement, we train our physical intuition, simply by being active outside.

And then – here’s the magic – the mind observes this, sees the body doing its thing, sees physical intuition happening, sees that the body goes where it needs to go without having to be told where to go, and learns that this is possible. Our mind learns how intuition works – and that intuition does work – by observing the intuitive movement of the body.

“…wu-wei is probably best rendered as something like “effortless action” or “spontaneous action.” 

― Edward Slingerland, Trying Not to Try: The Art and Science of Spontaneity

If we are active and in flow on a regular basis, the mind has plenty of opportunities to see that spontaneous, effortless action of the body leads to good results. It just works, all by itself, without having to make decisions. The next step is that the mind sees this and says, “hey, that seems to be working for moving the body, let me try that for myself. Let’s try some spontaneous, effortless thinking and see if that works just as well.” And (for the most part) it does go well, which reinforces the mechanism, making it more likely that the mind will allow itself you to go in that direction in the future, to allow intuition to happen, instead of going into more of an analytical, decision-making mode.

We can train and improve our intuition by being physically active (outside). The connection between athletics and intuition is so powerful that I now see that as the central theme of my work.

Authentic Physicality

Human-powered, self-directed, challenging, outside. 

We all know that physical activity is good for us.  Exercise ain’t all it’s cracked up to be though. It’ll certainly help keep you alive longer, and many people love their workouts, but it’s called a routine for a reason, right? I think there’s a better model, and I’ve come to  call it authentic physicality. To get in flow, to feel good, I have to be engaged in AP at least once a day. If I really want to feel great I need to do a double, or stay in AP for more than a couple of hours, and I know I’m really putting awesome in the bank on those rare days when I can get into AP in three or four different ways, for several hours at a time. 

Let’s break down what I mean: 


First of all, you have to be doing something human powered. If you’re not moving yourself, you’re not really moving. This is part of why I gave up riding motorcycles: it’s super fun, it’s self-directed, challenging, and done outside, but it doesn’t really provide any physical exercise, and it requires using an engine. And – even if you’re moving yourself, if what you’re doing requires external power as an intrinsic part of the activity, it’s not going to be as fulfilling – and it will likely be more expensive and energy intensive. Human-powered activities are also, very simply, simpler. We don’t need any extra complications in our world. Another thing about motorcycles that I realized at some point was that I no longer enjoyed having the machine and all of the process and tools required to keep the machine alive. We pay rent on everything that we own, and especially with machines – our machines own us as much as they require us to maintain them. 


I find self-directed activities more interesting. This means figuring it out yourself, for the most part. Having a mentor or a leader is great, but if someone is holding your hand every step of the way, it’s too easy to lose awareness of what is happening and what you are doing. Americans love guided activities. Get a guide if you need one, but don’t just follow; work with the guide, and only as long as you absolutely need to. And then try leading something yourself. We’re all capable of leadership, and it’s far more fulfilling than otherwise. 

Note that I mean self-directed, not alone. For mean this usually means doing individual activities like kitesurfing with other people. Climbing falls somewhere in the middle as it’s most often done as a pair activity. Team sports can also require a lot of self-directed activity. 

How to use this criterion? I went on a short river rafting trip last year that was human-powered, challenging, outside, and definitely not a ride, but we basically just paddled when the guide told us to paddle. The activity felt good, but I don’t think it fully qualified as authentic physicality. 


Doing something that isn’t intrinsically at least somewhat challenging is simply boring. Same if you’re doing something that you’re already so expert at that you can do it with your eyes closed. However, as Mihaly Csikszentmihalyi points out in Flow, it doesn’t have to be – in fact, should not be – something so hard that you simply can’t do it. In fact, completing attainable goals, achievable challenges, is a key part of getting into flow. It feels great to level up, and it’s good to do that as often as possible. Progression is great. If you’ve mastered something, find a way to introduce a challenge again, and/or start teaching others (which is itself a challenge). 


Being active outside and in the natural environment is so important. Most of us live in cities and we certainly get some benefit from being outside even in urban environments, but nature is far more stimulating and inspiring. As Nassim Taleb writes in Antifragile, “what Mother Nature does is rigorous until proven otherwise; what humans and science do is flawed until proven otherwise.” Another reason, also cited by the same author, is that a “wealth of details leads to inner peace.” We need the fractal detail of natiure to occupy and inspire our minds. So: running on a treadmill in the gym is better than nothing, running outside on the sidewalk is better, but trail running in the woods is far superior and provides multiple benefits to the body and the mind. 

A note on “extreme” sports

Some people think of some of the things that I do as extreme sports. I don’t use this term. The word is vague, subjective, relative – and overused. It’s also not relevant – authentic physicality is most often not extreme at all. Most sports that might be called extreme are complicated, required a lot of gear, and can only be done in very specific locations (and this require a lot of engines/fuel). 

The back story 
I’ve always been highly physical. Although I grew up in the city of San Francisco, my parents were outdoorspeople who took me backpacking for the first time well before I could walk. I was never attracted to team or ball sports much, but I enjoyed hiking, camping, backpacking, climbing, sailing and skateboarding from a young age, and did a lot of those things plus snowboarding, mountain and road biking, windsurfing, surfing, stand-up paddling, snowshoeing and trail running through my 20’s, 30’s and into my 40’s. In recent years my primary sports have been kitesurfing, paragliding, and open-water swimming – and it’s only in recent years that I’ve pursued any sport with enough regularity, dedication and aspiration to feel like anything of an athlete. 

As I’ve become more athletic, I’ve stopped doing some things that I used to enjoy: snowboarding, riding motorcycles, sailing boats, river kayaking, CrossFit. As started to think more about why I gravitated towards certain types of activities and away from others, I began to develop the idea of authentic physicality. There are too many activities masquerading as sports that lack one of the key qualities of AP . Hooking yourself into a zip-line might feel challenging for a moment, but it’s not active, not human powered, and not really physically challenging (unless you’re catastrophically unfit). At the end of the day things like zip-lining are rides, not sports, and you won’t get fit or into Flow by taking a ride. I don’t think anyone – not even a child – is really using their time well on a ride. 


The easiest and purest way to do authentic physicality is trail running. Other great AP activities are walking, hiking, backpacking, open-water swimming, rock climbing, cycling (especially trail or mountain biking), paragliding, surfing, stand-up paddling, snowshoeing, xc/backcountry skiing, and skateboarding. There are lots more – get out there and let’s hear em! 

Upgrade your decision-making

In January 2017 I led a workshop at The Battery entitled “Upgrade your decision-making”. My goal was to share some of my thinking about Athletics and Intuition in the form of a “Decide Nothing toolkit” – a few simple techniques that I use to help me stay in flow and make decisions intuitively. Some of the techniques that I shared are

  • Move without hesitation
  • See over the mountain
  • Shake hands with monuments
  • Check your messages
  • Welcome the unfamiliar
  • Roll the dice

This workshop was continuation of some events that I hosted in 2016 at the Battery and part of a series that I will be leading through the rest of 2017 on Athletics and Intuition. Check The Battery’s Events page for upcoming dates; the next one is scheduled for April 10, 2017.

How I learned to love advertising

I always hated advertising. Perhaps that’s not quite true? I feel like I’m supposed to say that. I might have admired the verve of some ads, but I never thought of it as a good thing (imagine, some do!). I was a skater. I tried to feel punk rock. I was anti-yuppie. I did have my consumer side though: Starting in my teens and even into my thirties, I dealt with social anxiety in part by shopping. When I lived on Church Street in high school years I used to go to the record store a lot (OK), but also this particular shop that sold tee shirts in various colors, always checking for a new one (not so OK). I bought cameras, jeans, shoes, shirts, suits (lots of clothes), drinks, airplane tickets, gifts – overall, mostly clothes.

At some point I started to notice this buying impulse and channel it into non-buying. I’d walk myself through the shopping process, see how tiring and pointless it was, mentally spend the money – and be disgusted. I started to see the freedom in not spending the time and money, in not burdening myself with another thing.

In my late twenties, I took a job with a promising tech/media company. I had been working for a bigger, older software company doing consulting work, enjoying that quite a lot, when two things happened. I noticed the internet happening: I had a client, a bank in Boston as I recall, and they wanted their bank “on the internet”. This was 1996. Good for them for asking! The company I worked for said it wasn’t possible. I wrapped their big Unix server app in a perl script and had it print out HTML at the end, showed that to them and they were pretty impressed. I guess I got the picture too.

The other thing was that this job required me to get on a plane every week. There is a certain glamour in that and it wears off as soon as you come to your senses. We’ve all seen the movies about the business traveler trying to make the most of his/her situation, and it’s never that sexy. I started to realize that I felt rather homeless. Already my friends thought of me as that guy who was never around, just showed up for parties. Again, that can be fun, but it’s not a long-term strategy. Since I had already decided that I would never do a daily commute by car, and I was looking for an alternative to frequent airplane travel, I decided to look for a job that I could walk to from my apartment in North Beach.

My friends assured me this was folly. There were no software jobs in San Francisco proper. I think I knew that I didn’t really want to work for a software company. I interviewed with a few. I wasn’t really a programmer, I hadn’t studied computer science, I didn’t know any algorithms. I had seen or bought or read a few copies of WIRED magazine, and I heard that they had offices in the City. I sent someone (Joel Truher) and email. I wish I had that correspondence. We met a few times, often on the roof of the building (why?) and in the end they offered me a job writing code and managing the engineering team on the side.

I wrote a ton of perl that did nothing all that useful and tried to manage the bunch of burners that lingered in the dark with their LSD hangovers, writing code that that continually crashed Apache, Sybase, and whatever else. Everyone was up at odd hours all the time. Computers were still fairly slow; if something crashed while trying to grind through the day’s events, it would often be impossible to catch up – we had to throw away a lot of data. When I think about what got me that job, and what I was good at in software in general, I think it’s this: estimating. I’m good at keeping it in the ballpark. And this is super hard with software. Super hard, especially when you are making everything up.

Advertising just sort of crept into the picture. Someone showed me a script that Crispin wrote that stuffed ads into outbound HTML. Joel showed me some LISP (was it code?!?) that was supposed to decide what ad to shove in. He was ahead of his time. Then we decided to build a search engine: HotBot. This was before Google. We had a deal with Inktomi to provide the back end and the search function itself, so we had to built the front end – and the ad server. By then we had already served “the first ad on the web”, we must have been making some money that way, and ads were going to be a big part of the search engine from the start. We had to figure out how to serve many many millions of keyword-targeted ads per second, and then to produce accurate statistics and reports about what ads were served alongside which search terms and why.

This ad-keyword project lit up my nerd brain. I dove into the spaghetti of (thankfully: perl) code that was the back end of the ad server and made many enhancements. Using some of what I had learned on earlier systems, I managed to turn the all-or-nothing nightly process of consuming the web- and ad-server logs into a continuous parallel process that could be farmed out to as many processors and disks as we cared to throw at it. I also figured out how to make a stew of the the guts of the ad server so that it was able to hold thousands of possible keyword-targeted ads in its little mind while responding to queries, without crashing. All of this fascinated me, at least briefly. Jobs are like that sometimes.

I’m not sure if even then I was aware that I was working more and more on “advertising”. Strange that it didn’t dawn on me. I think it came down to this: the work was engaging, and I was excited to be doing something fairly unique.

AdMonsters was essentially an outgrowth of that HotBot keyword targeting project. I remember discussing it at our first meeting in June of 1999. I was proud of the work I had done – and the uniqueness was proven by the fact that our first group was so small. There were fewer than twenty people working on that crap. And it was crap. But I still didn’t really see that. It just felt good to be doing something engaging and unique.

See how hard it is to see the world from the little road you’re on? I was happy to have a good job, happy to getting paid well, happy to able to do my own thing, again, to have a unique job, feeding my ego basically. I wasn’t paying that much attention.

There were signs. I was offered a job, an up-the-ladder management position, a mega opportunity in a lot of ways, a job that would have made me a lot of money. I turned it down. I didn’t quite know why. I didn’t listen to myself hard enough. I convinced myself that I didn’t want to leave San Francisco, that I didn’t want to travel so much. As close as I got was that I didn’t want the life that I imagined having, if I had that job. That I didn’t want to be that person. This happened twice actually.

I loved putting together conferences. There’s a lot of stress, and it is repeated. That’s not the part I loved, but I didn’t hate it, or I responded well to it. And I loved the gratification of seeing it all come together, so many “moving parts” – people – all timed perfectly to create an experience over just a few days. Clearly, this engaged and enlivened another part of me. And people loved the conferences from the start. We (well, I, to begin with, because it was just me for several years) did a really good job.

The conferences were about advertising. More specifically, it was about the software that web-based publishers (companies that make stuff you read on the web) use to put ads in front of your eyeballs. That’s what a publisher does: you create something that people want to read, you either sell it to the reader directly or you sell ads to companies that want to advertise to your readers (usually both). This doesn’t have to be complicated – you can just charge people $whatever to read writing and have no ads at all, that works fine if there are enough people that will pay. But: in the early days of the web, there simply wasn’t any way to charge readers anything. And so once the media-business types got the idea that software could be used in new and nerd-fascinating ways to (theoretically) show just the right ad to the right person at the right time, a landslide of investment began to pour into ad-serving software. And since, again, there still wasn’t any way to charge readers anything, all of the time and money that would have been invested at a non-web media company in getting readers to buy or subscribe was also invested into trying to generate revenue from advertising.

This is why the “online advertising business” exploded along with online media. Media business types saw media moving online, there wasn’t any way to charge readers to read, therefore advertising was the only possible revenue stream and the magic of software was so alluring that it seemed that it would be soon possible to make advertising perfect. That is: don’t show ads to the wrong people (so: no wasted ad impressions) and only show you ads that you, er, want to see (so: in theory, no annoying ads).

This massive, multi-billion dollar industry grew up around the premise that you could only show ads for men’s running shoes to men who run, and only to men who run who want to buy running shoes soon. Does that sound like bullshit? It should.

I mean, you can try. Anything is possible with software (it’s just a question of how much it costs). You can “target” men, men of a certain age who might run, men who visit running web sites. No problem, although it turns out that even this is much more complicated than those early nerds admitted. Can you figure out if he is intending to buy another pair soon? Can you? Who fucking cares? With a billion dollars of investment funding, you can certainly try. And they did.

Online advertising has been chasing this dream from day one. In the meantime, 1) Google, and 2) it became possible to charge readers to read, so just as we have been paying to read newspapers, books and magazines, we can now pay to read similar things online, and 3) it didn’t really work that well. Basically we spent something like $20B to figure out that the cost of almost-perfectly targeted advertising is more or less the same as not doing it at all. If it costs you $100 in advertising to sell $110 more of your product, it’s not worth advertising. Even if you sell $200 more, it’s not really worth it – you’re just breaking even.

Perhaps it’s interesting that I never used advertising to sell my conference. I didn’t need to. For the most part, people who were interested heard about it, or if they hadn’t heard about it, once they did they were immediately interested. Those who needed it most sought it out and found it – and then told others. That is the essence of a useful product.

At some point I started hating my job – my company – because it was all about advertising. I hated telling people what I did for a living: I produce conferences (bad enough!) – oh, about what? – they’re about online advertising. Dead air. I loved having my own business, I enjoyed the process, the doing, the producing – and I also really loved the positive feedback that I continued to get from my customers – the people that came to the conferences who told me how much they loved it, how it changed them, helped them in their careers. But the bad taste in my mouth for advertising got worse and worse.

Was I doing something morally wrong? Certainly not. I wasn’t even doing any advertising. I was making nerds happy!

My long-standing general distaste for advertising was crystallizing into a more concrete understanding that not only was advertising just sort of dumb, it was unnecessary – really, advertising is obsolete. This started to become clear to me. I wasn’t foresighted enough to conclude: now I must get out, but it did increase my urgency.

In parallel with this I finally developed some new professional relationships, some friends and peers who understood what I was doing from a purely business point of view, understood the conflicts and rewards and encouraged me to set aside my distaste long enough to work hard enough to make a real go of it. I had been distancing myself from the business because I didn’t want to be associated with advertising, and the business was suffering – not quite badly enough to fail, but enough to make the business more of a pain in the ass than it needed to be (and unattractive to potential buyers).

When I finally came to terms with the fact that this was my story, that I knew that I didn’t want to be that guy who took one of those up-the-ladder jobs, I knew that I wanted my own business, I knew that I didn’t like advertising, and I knew that I was neglecting my own business – then I knew what I had to do. Buckle down, set aside my distaste for advertising, run the business well, and find a way to get out clean.

Now that I’ve had time to read a few books, I see that I fucking won! Hugh MacLeod calls this the “Sex & Cash Theory” – a creative person should have two jobs, one that pays the bills, and the other that is the sexy, creative one. “Sometimes the task at hand covers both bases, but not often. This tense duality will always play center stage. It will never be transcended.” In his outstanding book Antifragile, Nassim Nicholas Taleb shows how “a combination of extremes kept separate”, a bi-model strategy of “playing it safe in some areas and taking a lot of risks in others” is central to anti-fragility. This can happen in parallel, or serially (as it appears to be happening for me).

I bought my freedom, and in fact not by paying someone else – I paid off my own house, and now I can live in it. It’s strange that the house was built on advertising, but that’s how it happened. So, as much as I hate advertising, and advertising is obsolete – I love advertising.