SUMMARY: In A Quiet Reflection on Failure Part I, I came to the conclusion that the past seven years of my life hadn’t worked as hoped for a variety of possible reasons. I have been thinking about my next move.

I’ve accepted failure, and I know it hasn’t been a total loss. But what exactly did I fail at? My goals, while they have shifted from year to year, are all based on the following premise:

I like blogging about two things: what catches my eye, and what I’m doing. Sharing more of what I do will which will lead to a satisfying, self-sustaining work-life balance.

My yearly goals, which I’ve documented in Groundhog Day Resolutions posts, have built on that premise. I’ve added specific projects, directives, and tasks that would bridge between that premise and. There was a problem with my initial resolutions: a lack of concreteness in the goal-setting. I tended to pick “states of being” (e.g. ‘be part of something bigger than myself’). However, even when I pick a concrete goal like “make 10 new forms for sale in the digital store”, I’ve fallen short.

The Old Ways: Impulsive Productivity

For a while, I thought this was OK, because I was still productive in a different sense: I kept making new stuff, posting design I’ve been doing, and sharing giant blocks of thinking. I just couldn’t predict it. This type of productivity is driven by impulsive energy that rides high on inspiration. I’d allowed myself to indulge in this behavior because it was better than producing NOTHING. Being a freelancer gives me blocks of time between projects, so I can get away with it; when working on a client project, I am forced to be more conscientious about time management.

There’s a problem with harnessing impulsive productivity: it’s unpredictable. It’s also difficult to build any kind of system that can harness its power in the moment of production; the best I’ve been able to do is collect the output for later use, like a barrel catching rainwater during a storm. My website, in fact, is just such a container for holding stuff I’ve made. In my mind, it’s a giant rusty bucket that could be so much more. Turning that bucket into a refinery, distribution network, and market presence requires a lot more work. That requires discipline and mindfulness applied over a lot of time. It’s not the kind of integrated system that can be built from scratch during an all-nighter.

That hasn’t stopped me from trying, of course. My website is the result of many up-all-night bursts of impulsive energy that happened when my dissatisfaction grew beyond what I could stand. In most cases, I tried to find the quickest and most off-the-shelf way to implement a feature and made-do with it. In a few cases, I was forced to absorb more web development knowledge to get the feature I wanted, learning PHP, HTML, CSS and Javascript on-the-fly so I could get the details right. I have had, however, a poor attitude toward this, as I was something of a snob when it came to comparing web technology at the time with the video game development I used to be involved with. Nevertheless, the website has slowly evolved, not exactly following best practices, growing like a small house that has been extended every year to become a sprawling complex, with stairway that lead nowhere and forgotten rooms containing lost treasures. There are over a million words on this website, and even I can’t find most of them when I want to.

Other than collect my sporadic output, I’ve also tried increasing the amount of impulse-producing energy. If I couldn’t predict when I would be impulsively productive, my reasoning went, perhaps I could at least trigger it more frequently. I tried various tricks, like spending more time around creative people and listening to their stories, sharing what I’ve done with new acquaintances, and volunteering for other people’s projects. The rationale is that interaction with other people triggers my impulsive desire to solve a new problem or help someone out. The resulting work is almost always useful to me as well, if not immediately. This has worked to some degree. It’s also helped me see the world from other people’s perspectives, and I’ve gotten some cool ideas and feedback about what I’m doing. However, on a whole I find this “prime the pump” approach just as unpredictable. Someone I might be helping could be fired up one day, then completely down the next. Going to a creative networking event, which I find personally very energy-draining, often yields nothing for the effort.

Finding a New Way

If I were an employee at a company that worked the way I’ve just described, I’d want to quit because this is a sucky way to work. I want predictability, and I want to work for a company that has a winning attitude and a tradition of excellent process. I’m held captive, though, by the benefits I enjoy (namely, the freedom to pursue my interests) and the existential reality of my situation (there is no escaping myself).

So if I can’t quit, my other option is to change my operations in a way that preserves the benefits of being a freelancer while boosting the level of quality. Qualitatively, the important metric is the level of satisfaction I feel. In pragmatic terms, the pertinent metric is how many projects I am finishing that are producing some kind of tangible result.

I have a few ideas.

1. Developing Discipline

Recently my internet buddy Colleen Wainwright shared an experience she signed up for with her writing publication coach Daphne. Colleen started by writing 15 minutes–no more, no less–under the baleful eye of her coach. She wasn’t allowed to write for MORE than 15 minutes, either; only after Colleen demonstrated the ability to stick to the regimen was she allowed to write longer. Judging from Colleen’s reports, it’s been extremely productive and eye-opening. I’ll ask Colleen to post followup information in comments (thanks in advance :)

I might have the original pedagogical intent wrong, but I think it works like this: by making a commitment to making daily progress, one gains a fuller understanding of discipline. It’s not only the about forcing yourself to do something (the simple view), it’s also about seeing the power of daily effort applied in small doses to a project. It’s that latter part, seeing the power of daily effort, that makes the habit palatable. This is a form of discipline that I was now partially acquainted with thanks to the recent NaNoWriMo experience, which showed me how daily practice is part of the creative process, and sticking with it despite my doubts would yield answers.

I also made an arrangement last week with one of my buddies, an artist with similar frustrations about his business growth, to try a similar experiment. Instead of working with a coach, though, we made the commitment to try the experiment for a week. Every day at 715AM, we would meet in the same Campfire chat room at 715AM every day (except on weekends), then work for 15 minutes on the personal project that was most important to us. No more, no less. The penalty for not showing up? I suggested that it meant we were incapable of being kings of our own destiny, an implied sign that we didn’t have what it takes because we can’t get up at the same time every day to work on the most important projects of our lives. The gauntlet was thrown.

At the time of this writing, we are on Day 5, and it’s been great so far. One benefit is just waking up every day early, because I have not only a commitment to myself but to my artist buddy too. We’ve had to accept limited progress every day, but it’s also shown us how even a small amount of daily engagement reduces our frustrations and anxieties, because we’re doing the work we believe is important. It is also great that we’re also able to talk about what we’re doing, which brings benefit through the sharing of each other’s insights about our work.

A surprising side benefit has been that 15 minutes keeps me from overplanning. The project I picked, predictably, was to write a plan about what to do. I’d tried to pick something concrete like “make a new ETP form” or “update last year’s calendar”, but these are just tasks in my mind. I wanted to figure out something much bigger, but I didn’t know what it was. It was undefined, uncertain, and yet it loomed large in the back of my mind draining me of energy. So I started by summarizing a lot of the things I talked about in the last post, and decided that instead of adding to the document every day, I would rewrite it every morning to refine it down to the clearest and simplest form it could take. But I’m getting ahead of myself; that’s for Part III of this article series.

2. Getting Over Myself

On review of my stuck projects, the blockage is not due to a lack of capability or time. After all, I have a lot of technical skills that I’ve amassed over the years, and I’ve been living as cheap as possible so I have the time to put into personal projects. Despite having the skills and the time, I’ve been stuck for years when it comes to those bigger projects because I am not starting them.

As I mentioned before, I thought it might be a lack of inspiration, feedback, motivation, what have you. I’ve explored these ideas before, generating some good theories if not very much work, and now I believe my stuckness is due to two other factors: my negative attitude toward certain types of work, and a lack of discipline in applying myself. Taken together, these factors also are closely related to my lack of professionalism toward my personal projects…hat tip to Steven Pressfield’s The War of Art for that latter insight.

Tied to the two factors is a personal hangup: a distaste for uncertainty. I prefer tested and reliable sources over random action, and I like to know what I’m going to get before I put in the effort. If I don’t know what the outcome is going to be, it’s difficult for me to start. Likewise, I am easily irritated by low-quality information, and this reaction creates so much drag that progress stops while I get mired in the search for better sources. This is a very old personal pattern that makes me judgmental and difficult to motivate on my worst day, leading to stuckness and anger. On my best days, however, it’s the trait that makes me more discerning and efficient, allowing me to generate missing detail that would stop others cold.

To reduce the friction of I feel from uncertainty, I’ve been learning to de-emotionalize my response to this work. It’s like what I do with unpleasant chores: empty my mind of the negative reaction, and then I go down to the basement and start shoveling the cat poop free of the irritation I used to feel. Uncertainty is my mental equivalent of cat poop, and de-emotionalizing my response to it coupled with the insights from NaNoWriMo and the Daily Commitment has shown me that it’s actually quite doable. Some of that mental cat poop is guaranteed to turn to gold! I just need to keep shoveling for it, with a smile on my face.

3. Acknowledging Desire

I can say with certainty that I want a fulfilling, creative lifestyle; that hasn’t changed one bit. The evaluation of the past seven years shows that I haven’t exactly achieved it despite having plenty of time to apply my skills to the problem.

Failure behind me, I am now free to question all my assumptions. I had said I was certain I wanted a certain kind of lifestyle. How did I know that?

I know it not from fact or reason, but from the feeling that this is what I want. I don’t know for sure that I want said creative lifestyle, but I am wishing for it. What I do know is that I have the feeling, and can describe it in concrete terms: I am dissatisfied, despite having tremendous freedom. I am not willing to settle for the silver lining implicit in this dark cloud and go with the flow.

That is a true feeling. I can either accept it as personal truth, or reject it and find another one. For example, I could learn to let go and find happiness in the journey not the reward, to be chill enough to accept things as they are, letting opportunity flow to me as the universe whimsically dictates. This is a valid approach, and that I’ve survived for those seven years without going nuts is probably due to practicing many aspects of this.

Today, I want to try something different. The yearning is still there, and I don’t want to compromise my standards by choosing NOT to strive for excellence. However, I also don’t want to be consumed by ambition or turn into a douchebag. If I can achieve what I feel in my desire, that would feel pretty good. What’s stopping me? I have the time! I have the skills!

I think the next plan of action comes in three parts: Resources, Mastery, and Accepting a Way. That will be Part III. And surprisingly, it may also have something to do with Faith.

[Revised for clarity DEC 9, 0047 GMT-5]