This post is long overdue! In early March, I was visiting my buddy Brad up in Winslow, Maine. The idea was to get a few creative entrepreneurs up in the same place (Brad’s house) and have a good time hanging out. In hindsight, the parallels with SXSW are very strong…it was the same energy, except on a much smaller scale. While we didn’t have “panels”, we did come away with several thought-provoking ideas about life and business and kicking ass.

• Daily Measurement is its Own Reward — Duncan talked to me about weight control, when I mentioned that I was on the path to a “healthier, sexier me.” Duncan weighs himself everyday, and finds that having that knowledge helps him monitor his overall eating. Yes! Frequent, accurate feedback is critical to goal-oriented processes. This is so fundamental that I think people forget it, and it’s exacerbated by process that doesn’t build in the right kind of feedback. Game Design 101, folks!

• Video and Podcasts — Brad and I spent some time looking into creating video and audio podcasts. This is something Brad had been thinking of for some time, based on the popularity of his “how to draw” series in Flash. I would link to the series, but I was blindsided by Brad’s caricature of Robert Scoble and couldn’t scroll down the page anymore because I was laughing so hard because (1) good lord, that’s something I didn’t want to see and (2) it’s such an excellent example of Brad’s humor. Note to self: don’t get on Brad’s bad side. :-) I myself have been thinking about audio podcasts as another way to put out my “personal vibe” out there, so people can get to know me from a different angle. People have told me I have a cool voice, though I need to enunciate more, so if that’s the case, why not use it? I’m supposed to figure out how to do a podcast. Skype looks like a reasonable way to do it. The trick is to keep the recording path in the digital domain as much as possible. Anyway, we goaded each other to shoot video to work out the process and get over our general embarassment about being on camera. We figured out camera angles, talked about equipment, and got over that hump of fear. We got things moving! Brad’s already has his first video on [how to draw a horse][horse] online, and I’m looking forward to seeing more. We ended up with a far different experience than when we started, but that’s the way it has to happen. The artistic approach tells you to make marks and let the way they fall guide you. The engineering approach tells you to know what you’re doing and build it to spec. The mistake we often make is to assume that the act of building is a monolothic one; it’s either artistic or engineering from beginning to end, or they must remain separate so they don’t step on each other. The right way to do things, in my opinion, is to use the processes in a game of leapfrog. Do an artistic hop, then an engineering hop, and so on. You’ll get to where you’re going though you didn’t know it at the time, and it’ll be the right place because that’s where you were going to end up anyway. If you do it right, it will rock.

• AdSense and Passive Income — We chatted about our AdSense experiences and other attempt to “monetize our content streams”. Brad’s been doing it for a lot longer, and pointed out tools like Wordtracker and Overture to find what people are searching for on the net so that need can be filled! Both of us have felt, though, that the AdSense approach is slightly crawly (no pun intended), and we’re backing off. We both feel that growing the pie by making positive contributions, as opposed to skimming a percentage off the top, is probably the better way to go. It’s more profitable in the long run to be the destination, as opposed to being a sideshow along the way. Make your own real estate!

• It’s Easier to Recognize Your Buddy’s Gifts than your Own — Brad is a really talented illustrator with a professional presence. Combine that with a great attitude, it’s no wonder that a host of opportunities are arrayed before him. It’s funny, though, that the thought of being out there in terms of making a video is so terrifying him…to me, it’s the logical evolution! To him, it’s a question whether “he’s good enough”. It’s so obvious to us, but not to him. That’s because we as individuals find it hard to measure our own strengths. Brad is an outstanding illustrator, and with a few simple lines can communicate ideas that would take thousands of words…such power! Brad knows this, of course, but like many of us he tends to see what he doesn’t know how to do as being a barrier. I am exactly the same way, though I can’t give a particular example because I don’t know what it is that I do that’s relevant to other people. I think it’s spinning words, maybe teaching, but I don’t really know. I’ve always done this, but have never understood how to plug it into the real world in a way that was (1) empowering and (2) filled with potential. I measure myself against other designers that I respect, other new media artists, other writers…in short, people who have inspired me. By that measure, I fall very very short. Taking a dose of my own freelance medicine, I realize it’s locality and quality relationships that matter. I may not be Milton Glaser, but I am trying my best to live up to his standard, and I am providing value because of that. Fame will come, or it will not. Being there in the moment for your audience…that’s priceless and it’s now. Worry about the future when it gets here.

• It’s Easier to Start when Someone Knows How to Prod You — Brad and I have known each other long enough that we know how to laugh together, and it occurs to me that this is pretty damn important. We’re also both freelancers, so we share a similar working experience, and how difficult it is to get moving on personal business-growing projects. Just knowing someone who “gets it” can help you get over that threshold of doing is a huge boon to productivity. The face-to-face is a big part of it, as are periodic phone calls to check in and push the right buttons. Big shiny positive buttons, mind you, that highlight the fun in learning through experience, thumbing out noses at the big bad spectre of failure. That’s the spirit that won us WWII! And gave us Warner Brothers cartoons!

• Leading From Within With Miss Heather — Brad’s daughter showed me a video of her dancing class recital. She’s already in the 4th grade (wow), and specifically pointed out the dance instructor, “Miss Heather”. I detected the slight emphasis on how important that was, so I paid attention. Miss Heather is in her twenties and has whipped the sleepy Watertown dance instruction scene into a competitive frenzy, to the point that other dance studios are copying her programs. As I watched the video, and saw the excitement and enthusiasm in every dancer’s eyes, I was struck by how lucky they all were to have a Miss Heather. She loves dancing, is super-competent and energetic, and dances with her students instead of sitting on the sidelines. She is an accessible superstar that has made herself accessible to her students as one of them. Leading through example, providing an outlet in a community that didn’t have anywhere else to go to participate in dance at this level, and being part of the community instead of just feeding off of it. That is fantastic.

• When Being a Kid is Really Being an Adult — Whenever I visit Brad’s family, I come away thinking alien thoughts like “yeah, someday I’d like to have a family”. Both he and his wife are amazing parents because they are utterly real with their kids. One thing I noticed early on was how they talked to their kids: no drama, no kiddy talk, just pure communication and acknowledgement of each other. They even apologized to each other when they misunderstood, no big deal. Everyone was in the loop. When we had conversations in the livingroom, everyone was included. When someone didn’t understand something, they just asked. No drama, no worrying about “looking stupid”. The feelings were there, but the foundation of trust was such that it didn’t matter. We were later chatting about how Brad, his wife, and myself didn’t really feel like we had become “adults” yet, because there’s a sense that we’re just not ready for it. Sitting on my couch here three weeks later, I think I know why: we think of adulthood as being stiff and unfunky, firmly set in our place in the world and in our ways. Who wants to be ready for that? At the same time, Brad and his wife are responsible for their own decisions. They’re doing their best to do awesome things that fulfill themselves, their children, and their community. And those are the values that they’re passing forward. When I chatted with Brad’s daughter, I remembered a lot of things that I had almost forgotten. When you’re a kid, you have the remarkable ability to see through bullshit. You ask direct, guileless questions. You know when things are good, and when things are bad, even when the adults think they’re somehow fooling you. You sense the hidden agendas behind every word. In short, the adult world is pretty stale, all about control, manipulation, and hierarchy. Yet, the adult world is where we as kids were inevitably headed, and we can’t wait to get there so we can make our own choices. To stay up all night eating cookie dough! To race cars! To fly to the moon! As we make the transition from childhood to adulthood, we have the choice to buy into the system because that’s the way things are, and conform to its expectations. The other choice is to rebel. Many of us aren’t brave enough to rebel until we’re old enough to not care about what we might lose. Some of us rebel against the system and lose everything, or we see others who have bought into the system with great success. I have felt all this at one time or another. But spending a weekend with Brad’s family reminded me that I can reset my expectations, and that the child’s point of view is the key to seeing the world in the right way again. Just because I’m old and balding doesn’t mean that the world still has to suck. The awesome part is that as an adult, I’m just treacherous enough to know how to get things done in an imperfect world, to build something that isn’t lame, and to attract like-minded positive people. It’s a start.

• Assets, Baby…Assets — If I haven’t said this enough already, making tangible things is where it’s at. For me, tangibility is defined as a physical artifact that you can hold in your hand, or see it with your eyes. Or, it’s a social connection: you had a meaningful interaction, and you’ve made a positive connection with the face and the name, so you’re likely to talk/collaborate in the future. Assets are props for that kind of interaction. In the context of doing business, it’s a far more useful to have something to show rather than just tell. People will argue that sometimes talk is all you need, but I like to think that when you’ve got something to show, that means you’ve got a significant competitive advantage over the guy who’s just waving his hands. When you can show something to someone, it does a lot of the convincing for you. You no longer have to guess at what the other person needs to hear, because you will know by their reaction. And when you put your asset catalog on the Internet, people will find you. Assets rock. You can think of assets also in the forms of capital. You got something tangible? That’s something you can sell. If it’s something that you can sell over and over in exchange for money, that’s a much better position to be in.

  So start building them! Now!

• Whoopie Pies as Big as your Head, and The Joy of Offering Value — Big G’s Deli has enormous whoopie pies. While some have decried the gargantuan qualities of these pies as a symptomatic of America’s continuing slide into obesity, it speaks to a certain mindset that I love: Give generously because it’s the awesome thing to do! I’m sure that Big G’s makes giant whoopie pies because they’re mind-bendingly cool. When you’re a kid, exposed to the normal run-of-the-mill whoopie pie, you’re pretty happy about it. They’re nothing special, though. However, when you then see the giant version, piled up like tires by the entrance, you have a new experience that builds on the first. First of all, you now realize that just because something is “usually” small, that doesn’t mean it has to be. That is an empowering thought. Secondly, you experience the pure joy knowing that someone was audacious enough to not only make, but sell such a monstrosity…that’s someone who sounds fun to hang out with. Thirdly, when you see that the cost of a megawhoopie pie is a mere two dollars, you think THIS IS A GREAT VALUE and wow, I have to tell everyone else! There’s a nice little marketing lesson in there, somewhere.

• Finding Your Peers by Keeping Your Eyes Open — Brad was telling me the story about the sign for his wife’s daycare center. Brad used to work as a signmaker in Maine before getting into digital media, so he knew a thing or two about creating artwork for this application. Brad also lives in a kind of remote area of Maine where there isn’t a lot of graphic industry, so he’s grown used to being pretty isolated from any form of design community. So Brad calls a signmaker in town, and gets the spiel about how he could use their signmaking design services. Brad tells him that he’s designing the sign himself, and that he used to do it so he thinks he has things covered. This aggravates the signmaker, who gives him a little ‘tude about it. When Brad goes to pick up the sign, however, everything is different. “This is a great sign!” the signmaker exclaimed (note: I’m paraphrasing liberally here), “You gotta understand, most people make their own signs and don’t know anything about graphics, and they end up with the most horrible signs and blame me for it.” So Brad and the signmaker enthusiastically talk shop a bit, and then they visit the signmaking studio. Here in the middle of Maine is a fully-decked out Apple Macintosh G5 system with a Cinema display and Wacom tablet. Brad is amazed. “I was thinking, I have all this stuff too!” Well, he has the PC equivalent, but still you get the point: our peers are everywhere. And finding people with the passion to share is as random as taking the time to show something to someone and see what sticks.

• The Salmon of Doubt — I have the audiotape of The Salmon of Doubt, a collection of essays by and about the late Douglas Adams. It’s been sitting in the back of my car for a few years, and I never really got a chance to listen to it until the drive to Maine. Douglas Adams, as I now know him, is my new personal hero. He was a writer who used to make fun of science (The Hitchhiker’s Guide to the Galaxy), but over the course of his life grew to embrace it. I’m coming at it from sort of the other direction, a technically-oriented person who’s learning to embrace writing. He was a passionate, intelligent man who was also a master procrastinator. Yet, he found success by generally being himself and writing about stuff that interested him. If there is a template for being eclectic and humorously yourself, it’s Douglas Adams. I have a new star to steer by!