This has been one of those gear grinding weeks in which nothing planned seemed to get done. Seemingly dozens of ideas and opportunities whizzed by me as I cursed and shook my fist like an old man. Toward the middle of the week I decided to stop fighting it and take some time to figure out what was going on.

Stuff On My Mind

It’s been a tough week in the blogosphere, with many good people going through some tough times. I started to write something about it, but then came to the conclusion that I was not writing for any reason other than to engage in commentary…so I stopped. I have a weird principle about not doing or saying anything if it doesn’t actually help in an immediate and tangible way, and while commentary is very interesting…it just didn’t feel right. Maybe in a few weeks.

I’ve also been feeling a little stuck. I’ve had a lot of interesting conversations with people over the past few weeks, and I feel like I’m ready to shift into high gear…but I’m dragging something. It feels like the parking brake is stuck on, or that there’s a flat tire, or maybe there’s water in the gas tank, or maybe I’m trying to tow too much stuff at the same time, or that maybe I should make sure I have someone in the car with me before embarking on a long trip, or…well, you get the idea. I’m ready, but I’m not ready.

TV to the Rescue

A few days ago I saw an episode of The Unit, a TV show about members of an elite special forces unit. It’s a strangely compelling mix of downbeat military action and women’s drama program; I’ve found that it provides food for thought. Anyway, one of the characters is helping another through a difficult moral dilemma who doesn’t know what to do, and asks for some help. “Here’s what the boss tells me,” he says. “If you knew the answer, what would it be?” So the other character, after a moment of doubt, writes everything down and is immensely relieved. It’s a good trick.

The Master Plan

I actually came across this tip after I had done something similar on Wednesday. Fed up with not knowing what to do, I went to the coffee shop with a pad of 11×17″ graph paper and starting drawing my master plan. At the right side I filled in an arbitrary goal ($100,000 a year) and then imagined what I could do to somehow achieve that. I didn’t care if it was particularly realistic or not, but I figured that starting anywhere would be a good place to start. I once took a math course called “Numerical Methods” that used a similar approach; when you don’t know how to solve certain kinds of functions, you take several guesses and use that data to choose new guesses, until you “converge on the solution”. I remember this used to drive me nuts, because at the time it seemed that the whole point of math was to not have to guess at all. Oh, how naive I was. Anyway, I don’t remember anything from that course except that the idea of starting anywhere and finding your way is actually not a bad strategy. My first master plan is just that: a guess.

Here it is:

I started from the goal, and started filling things in to the left, ending with the YOU ARE HERE thing in the upper left, which describes what I’m doing right now. I should mention this image has been edited in Photoshop to be a little cleaner than the original drawing; I was going to redraw the whole thing so it looked cooler, but I ended up fixing my computer for two days straight after it started acting up (new motherboard, more RAM, 4x faster, oh yeah :-)

The Master Plan breaks down into four categories of endeavor, which I’ve arbitrarily decided would each provide 25% of my source income or take 25% of my energy.

1. MAKE BOOKS

I’ve wanted to make a book for the longest time, since I love the way books feel and smell. One of my Groundhog Day Resolutions has been to create some kind of product, and some kind of book is probably the easiest thing to make from existing content. Companies like Lulu.com and Blurb.com are out there now, making it very easy to handle both printing and fulfillment at a decent level of quality. Of course, writing a good and marketable book is the hurdle.

I wrote down some of the calculations from the SXSW panel on turning your blog into a book, where a “standard advance” of $7500 translates to selling 5000 books. That works out to $1.50 per book. To make $25,000 at this rate, that would mean selling 16,668 books through traditional channels, which might or might not happen. On the other hand, selling an e-book for, say, $9.99 cuts down the number to 2500 units sold, but the value is somewhat questionable. And I have no idea what people are willing to pay $9.99 for.

Applying the “if I knew the answer what would it be” approach, I’d pay $9.99 for a book that laid out something clearly and insightfully that would help me get my own stuff done more effectively, paying for itself in a few hours of time saved. I’d want to see great charts and handy reference lists, and be drawn into the story of someone like me who’s making things happen. It would be part of a key that opened a broader awareness and community to me, and for the cost of a medium pizza I could have that forever. Wow, that advice from the TV DOES work!

2. MAKE PRODUCTS

Next on the list is the creation of some product, something that’s more of an object or tool than a book. Again, the easiest thing to put together is something based on my own work like The Printable CEO. The two immediate things that I could produce are pads of Emergent Task Planner and Emergent Task Timer, write a distilled mini-booklet for them describing how they work, and pushing them out there to see if anyone buys ’em. It’s not much of a plan, I know, but I gotta start somewhere. The printing costs are more up-front here, and there’s the unknowns of packaging and fulfillment. If these pay for themselves and get the word out there without costing me money, I would consider that a win. I would probably learn something about marketing first-hand.

A next step would be to start creating the “productivity systems” that have been languishing on the back shelf. A simple system would leverage off custom Circa or Rollabind notebook systems, and the goal would be to create a nice system that felt good to the hand. The profit vector is not clear to me, so perhaps this is something more worth prototyping. DIYing it here might be a happy medium: selling kits made of pre-punched PCEO or related custom forms with off-the-shelf notebook systems? The kit approach might be a lot of fun; I liked what the Make people were doing with their kits at the SXSW Tradeshow this year. Kits are awesome!

3. PROJECT WORK

I’m currently doing a lot of HTML and Actionscript development, though I’m starting to shift more into what might be called “strategy”. I have never been entirely satisfied by doing straight production and design work, finding it far more interesting to get into the what and why of the project in the greater context. I thought in the past that this was merely a necessary part of the design process, because I can’t make a dot unless I have a clear image of the greater purpose of my work; some have found it rather tedious to deal with. On the other hand, I’m starting to embrace the idea that this is useful work, and that it’s my favorite part of any project. Secondly, I’ve come to the conclusion that my work must always deal with individuals as individuals, not as abstractions. Otherwise, I just lose interest. I can wield a pretty broad array of digital media tools, but I don’t find joy in them unless they’re used to benefit an individual I can communicate with directly. That individual could be an end user or a specific person in the audience that I know. This is pretty important to me.

I’ve thought of a couple approaches to try defining my approach in a way that goes beyond generic labels like “strategy”, “information architecture”, and “experience design”. These are all fine fields, but they don’t quite connect with me because they lack a certain goofy enthusiasm. The two phrases I’ve thought of are related to the storytelling and game design threads that I keep stumbling upon during my periods of identity crisis. The first is Strategic Storytelling and Design, which has very light traction in the Googleverse and is therefore adoptable, and the second is Video Game Design applied to Organizational Process. I’ll write about these later, since creating a web presence that adequately explains and demonstrates the power of these techniques is part of attracting the people who might want to use these services. It’s another way of framing the creative process, the culmination of a 5 year effort to define what it is that I do. As it turns out, I always knew, but had never really had the courage to just define it for myself. I suspect that my incessantly-positive and insightful friend Senia might have planted the seeds of this in my head over the years, and I’m pretty sure rereading Jory’s Living without a Net series of posts helped realign my thinking after SXSW, which itself was a huge inspiration.

But I digress…the gist behind both of these new labels is that games can create life in the real world. Usually people think it’s the other way around, but I really believe that one can apply the same principles that drive great storytelling and game design in real-world scenarios. I try to do this all the time already, trying to create a spark that jumps between environment, artifact, passion, and desire. It’s the basis for how I teach and explain things. It’s the reason I love being alive in the world, and it’s an incredibly large field to play in. I’m a game designer, and I like to tell stories, and I know a thing or two about technology, design, and human desire. Surely there is a need for that somewhere, if I have to create the need myself through my writing and design work.

4. COLLABORATION

Ah, but I can’t do it all alone. I’ve been holding off on seeking true collaborators because, frankly, I’ve been afraid that it would not work out and I’d be left holding the bag. I’ve been burned a few times before, and this has made me a little gun-shy when it comes to pulling the trigger. But NO MORE. It’s time to create some group energy that benefits everything.

With my newfound focus on design and game-driven process, I may be able to contribute a certain “vision” in certain kinds of development projects. I’m also a good listener, if somewhat scattered. I think there are five hurdles to overcome:

1. My most immediate need is a way to maintain continuity on a wide variety of disparate projects; this may mean working with interns or figuring out a way of establishing lightweight project management; a dip into some of the agile methodologies could provide some clues. However, this presumes that maintaining continuity is my responsibility. Now, continuity is very important in getting anything done, but equally important is direction. Continuity management takes up huge parts of my mental energy, because I tend to be obsessively detail-oriented when it comes to this stuff. However, I don’t particularly enjoy doing it. An equally valuable contribution might be just one or two hours of my time listening and contributing to the development of various pieces of software and design. I may provide some writing, clarification, and design work as needed, but my responsibility would largely be writing the story we live through the application of real time narrative. If that doesn’t make sense, think of it as technical or creative direction.

2. What about ownership? With multiple people contributing work that’s difficult to assess for “equality of effort”, how do you avoid arguments? Frankly, I don’t want to worry about it, so I am thinking that everyone who contributes gets nonexclusive rights to the source assets and concepts, with which to do what they please. An example might be if I’m contributing design to a project, then I also get access to source code. The programmer would get access to my source design files. This might be a good way to rapidly build up my development skills by leveraging the work of more experienced developers.

3. Then there’s coordination. I’m thinking that it would be cool to be involved in 3 or 4 projects at once, with many people, so how do you keep track of it all? This is a tough one. Email sucks. A wiki might work, though I really hate wikis because they’re so ugly, and a lot of the open source collaboration tools don’t do a good job of showing continuity (there’s that word again…I guess I’m still hung up on it). At the very minimum, there needs to be a way for me and others to write the story of what’s going on, providing a clear vision of what’s happened and what might happen next. Then, there needs to be working areas for sharing files, source control, live documentation, and issue tracking. And for me to want to use it, it has to look nice. Any ideas on what that system might be? I know I’m being super picky, so feel free to tell me to get over it and just use X.

4. What of accountability and control? This has tended to burn me up in real project work, both for myself as a perfectionist and as a source of worry when responsible for the quality of others. Maybe the solution is to just let go and be happy if anything happens at all. Instead of a development timetable, we could take a unit approach to measuring contribution. That’s just another way of saying “I’m into it” or “I’m not”; make that clear up front that people will commit when they’re interested, and that they’ll commit to a limited engagement to push to the next step taking no more than X hours, where X is less than 4 hours. Each of these micro contributions will be integrated into the next build or release, and the contributors who took it to that next stage each get all the assets they used to build up to that point.

5. Finally, there’s qualification. Can just anyone jump in as a contributor? Is there a need for screening, or should everyone be able to join? What happens when there’s a mismatch of skill levels? The solution I have in mind is to have a skill show and tell, where everyone who wants to contribute needs to bring a few examples of their work. If you’re a coder, you need to provide a snippet of actual source code you’re willing to share, WARTS AND ALL, and be ready to talk about it. If you’re an application developer (a higher level of coder), then you need to show off your working app, with some snippet of code that you’re particularly proud of. If you’re a designer, then let’s see some design examples of something you really like, and have some source files you’re willing to put up. I think there’s a few good things that will come out of this. First, people will have to have real examplesof what they can do, and these become the means through which people can select who they want to team up with. Let the person who sees the potential in someone’s work be the one to make the call by seeing and asking questions. Secondly, the samples themselves becomes conversation pieces that help people start to learn about each other and the work they do. Thirdly, since people will be providing samples and chatting about their work, this is a good way for noobs (me included) to see what the bar is and know what I might need to bone up on. Say you’re a designer just getting started with Photoshop, and you’d like to get in on this group collaboration thing. So you put together your photoshop sample file of “cool art” you’ve done, and you upload it. You also get to see how other photoshop artists are doing things, because you’ll be able to download their files and read a bit about what they thought was particularly cool about it. You probably will learn something.

In the Meantime, I need to Regroup

So I have a ton of ideas that I want to launch this year. It’s almost April 4th too, which is the second Groundhog’s Day Resolution Review day of the year. On top of this I have a lot of outstanding projects and project work that I have not been moving quickly enough on. A significant backlog has started to build up, and I haven’t come up with a good system of projecting and booking the work so there are no conflicts. GTD is a system that probably would work well for me, but I am a little stuck on the capture and list-making side of things because I am (against the rules of GTD, I should note) prioritizing tasks and doing things out of order. I’m not sure if it’s just me being unfocused (quite possible) or if I actually do have more on my plate that I’m capable of handling. Probably both :-) There’s two positive things though I have today that I didn’t have last week: I have some sense of what I want to do with regards to the Master Plan, and I’ve also resolved, for the moment, the nature of my identity as a creative practitioner. These two things have bothered me for years, and now that they’ve been newly resolved I feel I can relax a bit more. I was thinking today about another productivity thing that I’ve read somewhere about the various altitudes one can use to assess goals. I think this was in GTD, and I’m sure others have written about it as well: there’s the “1000 foot” view, the “10,000 foot view”, the “20,000 foot view”, etc., of your goals and life. The closer you are, the more your experience and focus is dominated by detail that obscures the overall shape of things; have you ever noticed how much bigger a city block is when you have to walk through it? And how much stuff is there? It’s really cool…but again I digress. The basic idea is that if you want to see where you’re going, you need the “macro view” to help guide your actions in the “micro view”. This is a fundamental principle of any kind of analysis or application of effective action. The strategic picture dominates in the big picture view, and tactical execution dominates where the rubber hits the road. The same principle applies to Longer Term versus Short Term planning, and I decided to create a set of text files that reflected this. Short term planning can be realized in much higher resolution and surety than long term plans. Long term plans help prioritize and guide the selection of tools used in the short term. Here’s the list I made in a TextPad workspace: A TextPad workspace is just a bunch of text files that are loaded all at once. Here’s the files I’ve created, which are numbered to enforce a sort-order from short-term to long-term plans:

• 00 To Do — daily task continuity
• 10 Week Queued — planned task list to be done for the immediate week(s)
• 20 Project Scheduling — high level project planning
• 25 Side Projects — high level personal project planning
• 30 Project Inquiries — project pipeline, to be scheduled in 20 when ready to go
• 40 Project Possibilities — possible projects, need to be finalized and signed
• 50 Long Term Goals — my long terms goals, which are another form of project
• 60 Recent Contact — people I’ve talked to recently, notes on what we talked about
• 70 Contacts — people contact information
• 80 Good Ideas — random ideas and observations, with no direction
• 90 Bad Ideas — things that I’ve thought that I probably won’t do, but who knows?
• Scratchpad — a place for random jottings

The lower-numbered files are more immediate and concrete than the higher numbered files. As I come across tasks and items that I need to remember or do, I enter them in the appropriate text file. The general idea is that I have a continuum of micro- and macro-level tasks that are important to me, and that I can easily scan them. The reason I have contacts and ideas listed is that these are “ticklers”; who knows what the collision of a “bad idea” coupled with a “recent contact” will bring? It could become a good ideaor possible opportunity. The screenshot also shows a few optimizations I’ve made to my Windows setup:

• The menu in the lower right is my “quick launch” toolbar. It is a simple folder named _jump with some shortcuts on it, located on my Data drive so I don’t lose it if I reinstall the operating system. I find this menu is easier for me to use that the bloated Windows Start menu. To add your own, create a folder somewhere with the shortcuts you want, and then right click the Windows toolbar choosing the TOOLBARS -> NEW TOOLBAR from the menu. You’ll be prompted to choose a folder. You may also want to unlock the toolbar so you can resize the folder name in case it gets mucked up (if you double click it, it will expand to the width of the toolbar, and it’s a pain in the ass).

• I’m using a text editor called TextPad, which in addition to providing Workspace Files (shown in my jump menu as ^ProjectToDo.tws, has syntax highlighting. TextPad is a straight text editor, which is nice because it’s not bloated and it’s fast. I created a new file type, the .dtk file as shown here (it stands for “dave tracking”, if you must know). They’re just regular text files that I’ve associated with the TextPad application as a custom type. And because they’re custom types, I can define a custom coloring syntax file, dtk.syn, which highlights key words and symbols in the manner I want. Here I’ve chosen to make the default text color a lighter gray, so that the headers (the ## symbol in column 1, which happens to coincide with the Markdown syntax I use in my blog posts) and keywords like IMPORTANT, TODO and CALL jump out. This is so I can write descriptions in my text files that are just a little easier to scan for the useful bits of information if I’m in a hurry.

So That’s What I’ve Been Doing

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p>I’m going to start looking for collaborators soon, and if there’s anyone out there who knows of a place where this is already going on, has suggestions, or is interested in figuring this out, leave a comment and let’s start a discussion.

In the meantime, I have a lot of client work to finish, and some new work to book. If you’re an HTML jockey, Flash expert, Graphic Designer, business person, project manager, writer, designer, or whatever, shoot me a resume and a sample of your work. I think it would be cool to make a freelance directory that follows some of the principles I’m putting out there, maybe as a simple Wiki or something.