I’ve never really had a problem sitting down and spewing out a bunch of words. My process is pretty simple:

• Start somewhere, see where it goes, then try to make some sense of it in a closing paragraph or statement.
• If I have the energy, proof read and tweak the text. Otherwise, let ‘er loose!
• Hope no one notices that I’m a hack ;-)

I think think the process works for me because I tend to present in terms of conversational narrative. I write as if I’m talking to my friends, and I am constantly thinking of the best way to sequence a bit of information so it can be comprehended correctly. This actually doesn’t play as well in real-life; in the process of establishing the context, iterating the supporting facts, and drawing my brilliant conclusion, attention spans tend to wander. This is good, because it forces me to try to be more visceral and succinct.

But I digress.

Blocking on Organization and Motivation

I’m admitting to myself I’m blocked even though I have a process that lets me write about just about anything. I’m doing it right now, relying on old conversational patterns and a certain shamelessness in applying stream-of-conscious techniques to this very sentence. I know that the very act of describing what I’m doing here will build some sense of anticipation, which is something I can do for maybe one or two sentences before people get fed up and demand an actual thought. The thought is this: I’m blocked by my desire to categorize my writing.

Let me explain. This site has well over 1000 posts on it, of varying length and quality, covering a broad-but-bounded set of categories that no longer really describe what I’m doing. This is important to me because I’ve had the idea of doing a massive site reorganization to improve access to those 1000 posts. This is partly an information architecture challenge, but mostly I am bottlenecked on time, resources, and technology. I’m busy with projects, short on time, and restricted by the lack of pre-existing reorganization plug-ins for Expression Engine. Technically it is doable, but the admin tools in EE really aren’t up to the task. It will take time and energy I don’t have available in large amounts.

The diagnosis: because I am not happy with the space (this website) I am putting my content in, I tend not to want to write. In the back of my mind, it’s work I will have to go back and re-organize later; why make more trouble for myself in the future?

There’s another reason, though: I have also been more aware recently that I feel an obligation to continue developing interesting downloadable forms and software tools. I haven’t had much time to do this recently, and I have wanted to rewrite and re-photograph the existing set of tools so they make sense to people coming to it for the first time. Again, I need energy and time in large amounts.

This feeling of obligation, which I realize is entirely in my own head, is a form of “self-boxing” due to my experience with the site’s growth. I know through my website analytics that a lot of people are reading the blog because of the productivity stuff, and I am mindful of that. I also know that because I am known for this kind of work, it is the most obvious path to take to “success”, which I will define as “opening doors and attracting opportunities”. The development roadmap would look something like this:

1. Rewrite the Printable CEO pages for new audiences.
2. Write a book describing use of the PCEO, and general productivity practices.
3. Reorganize the website to put all the productivity and tool stuff in one section, that reinforces the message and utility of the Printable CEO.
4. Establish a daily blog posting schedule for productivity posts, using original sources and design.
5. Establish the official online store, pre-populated with three products: Pre-Printed Compact Calendar, Pre-Printed Emergent Task Planner, and something else.
6. Generalize the Printable CEO Process for 15-minute, 30-minute, and 60-minute presentations.
7. Start getting some magazine and speaking gigs, unpaid at first, but designed to build credibility.
8. Start floating book ideas to agents.
9. Hire a developer to build the database back-end, and maybe even the front-end, for various software tools designed around the time-tracking methodologies I’ve been using.
10. Develop income from all these sources, with the goal that by 2010 I will be self-sufficient and able to work on this stuff full-time.

I look at that list, and I think it’s very doable. And at the same time, I am absolutely AMAZED that this list makes me want to throw up. It doesn’t look like fun: It looks like a project that I need to manage. I could perhaps find people to collaborate with, but I also see this as being a tremendous energy drain until I stumble upon the right people. And, I am loathe to disappoint people who would love to collaborate but aren’t a good fit for whatever reason. It’s a lot easier to just do this all for fun, give it away, and let people enjoy what they like.

I can take away two things from the above observations:

• I like to get things done in one sitting. If I can’t do it, I tend not to want to start. This may be the main reason why I procrastinate.

• I approach my work like an artist, not a business person. I can think business. I can think project manager. If it is my job, I will execute those two functions to the best of my ability. But I am personally motivated by the desire to live artfully, which is another way of saying I like people who are self-empowered and positive-minded. What I have never stated, though, is that to be this kind of person is to achieve some form of fulfillment that is beautiful to behold.

Reshuffling the Blocks

Restating the main blocks I am experiencing:

1. I’m not happy with my website structure, and I don’t have time to fix it with the tools I currently have. It will take time to acquire/build the tools I’ll need to improve the site experience. Because of this, I don’t feel like writing. THE SOLUTION: Get over it and write. It’s what I have time to do. Revel in the mess. Let “Future Dave” worry about cleaning it up. Oh, and I should just write smaller articles too. As for meeting the expectations of a given audience, well, that will have to wait until I get the organization sorted out.

2. I’m impatient, and want to see results right away even though I know it takes time to do anything of substance. This is just the way my personality is wired. THE SOLUTION: I have to just work with this character foible, and learn to push through it. I might start by deliberately doing “can be done in one sitting” tasks in two parts, just to get used to it. The split needs to actually interrupt the process before it is completed, otherwise it won’t count. This may seem counter-intuitive in terms of productivity, where finding a “natural ending place” would be the logical breaking point. For example, I might finish writing the draft of this article and save proof-reading it for tomorrow before I post. However, the end result I am shooting for is a new mentality, of stopping in the middle of something and not obsess about losing my momentum. I need to experience (note I am not saying learn, which would be premature) how to start/stop my creative momentum when I want to. I am sure some interesting insights will result from this, and that is when learning can be applied.

3. I have an artist’s sensibility toward my work, and this prevents me from wanting to deal with it as a real project because it sullies the motivational purity I feel from it. I have to not be so self-conscious about wanting to make a living directly from doing stuff I like. THE SOLUTION: I actually am not quite sure what to do about this, because this runs more deeply than I ever imagined. My tendency is to want to give things away, and it might be because I have lingering doubts about whether what I’ve done is really worth something on the open market. I am far more businesslike when it comes to my time, because I am more familiar with the service model. And yet, this is the model I want to get away from. I ultimately want to be a content creator, not a service provider, offering a number of awesome and inspiring products because—and this is a big AHA—it is an immediate payoff for both parties. Sure, it takes time to create and market products, and it certainly takes time to learn how to use them, but selling a wonderful product is a lot more like a gift exchange. Perhaps this indulges my sense of generosity (in this case, with my applied design and thinking on behalf of a happy purchaser) while appeasing my impatience (exchanging money for stuff is instantly gratifying).

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p>OK, I’m done writing for tonight (about 60 minutes, if anyone is curious). Hopefully the long drought is over.