A few days ago I had the idea of making “task juggler cards” to help me make my tasks feel a bit more physical. Combining the index card docks with business card-sized reminders, I figured they would help keep tasks present on my desk in an interesting manner. On top of that, there are a lot of ready-made business card management solutions out there, from card cases to folders to scanners.

The first day of use was accompanied by an unexpected reaction: that of intimidation from the tasks. I also realized that what I really wanted from these task cards wasn’t a structured process, but more of a supportive one. In other words, these task cards should be more encouraging than enforcing.

Here’s my thoughts on that challenge:

• The basic idea behind a productivity system is to do more desirable work, to gain more desirable outcomes. Productivity is about producing.
• The hard part about being productive is that producing is a complex chain of inter-related activities. If you don’t know what the chain is, or if there’s any part of the chain that’s uncertain, then you can’t optimize. Refining one’s productivity system requires having a procedure or methodology in place that produces the desired result, and then maximizing its use.
• Maximizing usage of the system can be mechanical, psychological, or operational. By maximizing the use of the system, the volume of desired results increases.
• At times there are unknown aspects to the system which create inefficiencies or breakdowns. The system doesn’t exist in isolation, but in a context of other motivations, pressures, risks, and opportunities. The system periodically requires tuning to both the individuals involved, and also in reaction to external context that affect it.
• Productivity systems have to be monitored and observed also, because measurements are what give us useful feedback regarding how well it is working. What you measure, however, has a powerful effect on hos the system itself works within its greater context. Measure the wrong thing, and you may skew the system toward some unintended or self-destructive result.

That’s the nuts and bolts at a high level. Let’s consider the individual, though…this is one of the external contexts, and the one that matters most to me right now:

• The individual seeks to understand the context in which he’s operating.
• The individual doesn’t want to have to navigate both high level and low level systems at the same time
• When it comes to doing actual work of a high quality, this requires a deep dive and the ability to focus on only one thing.
• The context of deep dives need to be readily accessible, to help maintain orientation and reduce anxiety about what’s being done.
• Once the deep dive is complete, then the high level context should be readily accessible so the results can be delivered and seen as part of the big picture.

In other words, the individual wants to know what they need to do, very specifically, and also be able to know their work is valuable in the greater context.

So there are two challenges here: how does the individual know what to do, and how do they know the work is valuable?

• An employee is told what to do. They are given goals, challenges, and constrained resources, so they immediately can go into problem solving mode. It’s also a social thing…employees can talk to each other and their managers, mentor each other, and muddle through toward a solution. A great deal of self-correcting reinforcement is available. In the event the challenge is unknown or is outside domain expertise, the employees may lose course or become anxious as to the right direction. If the challenge is to be discovered, that can also lead to anxiety if the mindset isn’t correct or the culture is not supportive.

• An entrepreneur has to figure it out as they go, and discern value simultaneously. This is much more fraught with uncertainty, particular in fields where the path and procedure is largely unknown and untested. However, success can be measured quantitatively and objectively in terms of business, which is “not personal”.

• An artist goes through something similar, though the challenge ma be more internal and exploratory. However, an artist that is seeking commercial success is an entrepreneur as well, so they have to deal with the double-whammy of having the work be very personal AND financially viable.

• Value comes from external validation, affirmation, and rewards with opportunity, recognition, and money.

The specific case I’m interested in is that of the entrepreneur who needs to forge their own path. The key to being an entrepreneur is to keep going and keep experimenting, one eye looking forward and the other eye monitoring the operation for signs of gold. Getting still more specific, the case I’m interested in is of the LAZY entrepreneur. Laziness isn’t necessarily a character flaw. It may just be that energy is low or in short supply. Perhaps the entrepreneurial activity is fraught with uncertainty; this is a heavy mental toll. Or the entrepreneur is juggling a full-time job. Let’s go back still further and ask what the point of productivity is. I’m going to go out on a limb and say that it’s essentially about improvement. The fundamental desire is to “get better” or “improve one’s self”, and becoming “productive” is one strategy. The desire for improvement is, unlike task definition, very easy for most people to state. It comes in the form of a wish, followed by a suggestion as to what the operative form of that wish would be. This is the typical form of a resolution, and these are the resolutions that often fail. However, there is a remarkable clarity to them in the moment of wishing. That’s something that I think we can harness. I had a great deal of trouble with my initial set of goals. They were really wishes, expressed in somewhat higher-resolution form. Here’s a snapshot of my Trello board (I’ve made it public) as it currently stands: Let me go through each terribly-defined task:

• ETP 1 MO DESIGN – this is a new ETP product, a one-month bound journal in the A5 size. In the trello board I’ve written down a few tasks the are related to it, which I didn’t have on the task card for it. Each of these tasks, though, requires additional task sequencing. What does “refine design” really entail? Either a decision needs to be made, or a question needs to be answered. And sometimes, we don’t know enough to even ask the question, so we need to research. Sometimes we don’t even know if we want to do it, so some kind of experience is needed to get a gut check. And presuming that a decision or question has been resolved, the creation of process or prototype needs to happen, which requires learning and best practices and finding suppliers and mentors and other experts to provide guidance. Presuming, of course, you have the time and money to spend. Once that process and prototype is ready, building a self-sustaining business or reusable piece of technology that will yield the dividends you want is necessary, as is the marketing and meeting the right people to collaborate with or minister to.

• Marketing Collateral – this is related to creating more opportunity for myself to make money, land gigs, or meet people. It’s rather ill-defined as a task. These are things that would be good, but they’re hard to get excited about.

• Creativity 1-sheet – this is some brainstorming I’m doing with a new acquaintance. The result is some thoughts about how to run a good creative brainstorming sesion, or something. I actually have what I need for this: the question, and the ability to allocate an hour of time to think about it. I actually have a deadline for this on Tuesday, so need to move it up.

• MediaTemple Transition – My old virtual server needs to be upgraded to the new one. MT is transitioning everyone at the end of the year, but I need to take care of it first to make sure everything works, as I have extra services installed. This is relatively well-defined in my head because I’ve done it before, or it’s more accurate to say that I’m relatively CONFIDENT that I can do it without much confusion at this point. I still need to make a list, though, of everything that needs moving. A first step would be to make that list and sit on it a bit.

• Index Card Docks – this is a continuation of the wood finishing, also figuring out the business aspects of things.

• Convert Game Code to XNA 4.0 – An ongoing project that leads to opportunity in the future for doing more museum interactive work, while polishing programming chops. Sort of my high tech play for recognition in a field I’ve been away from for a number of years.

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p>On the surface, these tasks seem fairly defined, but there are several tiers of desire wrapped up in each of these tasks. I’m going to take a stab at them:

TIER 1: THE BASIC WISH

Takes the form of I wish I was a better programmer. Then I could make more money doing cooler projects. This is the wishful thinking, dreaming aspect. It can also be expressed in the negative form: I wish my boss wasn’t an asshole. I want to be my own boss.

The shortcut solution is to make a resolution that states affirmation of the wish, with an identification of what that “better state” will be. I am going to stop smoking this year. However, lack of specificity of action or understanding of what it takes to be one of the new state kills the action. It seems impossible, or at least foggy enough to easily forgot.

TIER 2: THE FIXATION ON A SOLUTION

One step beyond the basic wish is the identification of a likely gateway or power that will grant the wish, if only it could be acquired. I will write an iPad app! I will buy a lemonade stand!

This is a little better than tier 1, in that it has identified a vehicle that may be capable of conveying one’s self to the promised land. It becomes a little more real. Research into what’s required to acquire the solution preoccupies much time.

TIER 3: ACQUISITION OF TOOLS AND RESOURCES

Programming tools are purchased. Books are acquired. Lemons are squeezed and converted into juice. All the tools of the trade are within ready grasp. Now what? The potential state for doing a full transition into the new state is possible, but this is where procrastination is likely to strike. That’s because the realities of actually BECOMING a new person requires a lot of personal work. You have to learn new things. You have to learn how to discern one thing from another, because one of them is better than the other. You are going to be slow, and you are going to suck. This is hard to get over. You may not even know what exactly to do, because the benefit you can perceive is much different than the expertise required to produce it.

This is also a matter of learning how to plug one system into another. There is often no turnkey solution available to you when you first start. you’re going to have to figure out how each piece fits into each other, and it’s going to be awkward.

TIER 4: DRUDGERY AND LEARNING

The rule of thumb I use is at least 100:1 of time spent or iterations made creating an experience, versus the time it takes to actually consume it. To produce high-quality experiences, the ratio goes up and up to 1,000,000:1 for the highest-quality experience possible. So, if you are creating a unique lemonade that takes 1 minute to drink and enjoy, the amount of effort it takes to invent that lemonade at an acceptable level means making that drink 100 times, or putting 100 minutes into perfecting it. A really exceptional lemonade might take 1000 minutes of experimentation. And so on.

This is hugely daunting. However, creating anything of quality is going to take this kind of learning and effort. Money will be spent on promising technologies and ideas that prove useless. Parts you need don’t exist, or take years to track down and find. You don’t know the names of things that you need, and people try to sell you things that they promise will work but don’t. It’s up to you to cull the good from the bad (which depends on what you need in the first place), and somehow not go insane or lose hope.

TIER 5: THE BREAKTHROUGH

At some point, enough pieces exist and are working with each other that the process exists! It works! It may not work very well, but it is running on its own steam and doing something you regard as useful. Congratulations! You have successfully gained benefit and experience, and done what you set out to do. You lost 50 points. You are down to 1 pack a day. You have a program that does something on the iPad, all by itself, without crashing. You have made an animated short film using 3D Studio Max. And so on.

This is just the beginning though. Now you have to get other people to buy into what you’re doing. And this is often hard. You may have mastered a difficult technical skill or learned how to build something very cool, but if people don’t understand or want it, you’re doomed if you are doing this for money.

TIER 6: THE REALITY OF THE NEXT LEVEL

At this point, your work will have to speak for itself, and you will have to make it possible for that to happen. Marketing collateral. Showing your work to people. Getting people interested. Finding out what they are looking for. Accepting other ideas from people, without taking it personally. Realizing that your work might not be as high-quality as you though, in the greater marketplace. Do you up your game or resort to other shenanigans?

You may have to refine your workflow, fix the broken parts, or go back to the drawing board. But don’t through out what you’ve done…it’s valuable research, and even if it’s not where you want it to be it is WHERE YOU CAN START. You may be able to figure something out here that works for you, with the existing level. It’s version 1.0…sell it until you have version 2.0 ready.

The experience of selling or promoting your work will also teach you a lot of things. This will lead to other opportunities that you will have to evaluate.

You also discover there is VAST room for improvement in yourself. Things are not as simple as they seemed. They are actually quite complex, and keeping track of them requires mental discipline that you need to develop.

You may also find that the next level ISN’T what you wanted or expected. You really miss those cigarettes, because they keep you awake. You don’t know if you really want a life without carbs. Maybe you’ve decided iPad apps are too unrewarding to make when no one buys them, or you find you don’t care enough about programming to do it all the time for what you get.

Do you stick with it, or bail?

TIER 7: FORTUNE AND GLORY

You decided to stick it out. You like doing this. You start to see things happen. Your life balance has changed, and you decide it is the improvement you have hoped for. Mission accomplished. You are in a better place than where you started. You have a working set of processes and principles that you have personally tested. They’re yours, and no one elses.

Your understanding of the process continues to be refined, leading to more innovation and opportunities that didn’t exist before. After losing that weight, you started rock climbing, and it’s amazing for your soul. Your programs start selling, and you are making more and more programs and are making a name for yourself. Your line of scarves attracts the attention of another Etsy designer, and you talk, and you start collaborating on something even more epic. You make enough money to buy that new big-screen TV you couldn’t afford before.

TIER 8: THE NEXT BIG THING

Having had a taste of fortune and glory, you start wondering what’s next. You have an idea for something completely different, because you are still full of wishes. This time, you are prepared for the long journey, and are determined to deal with any challenge that gets in your way.

Putting it into Perspective

Each of those task cards exist in the context of these seven steps. That’s important to realize. That’s the continuum that these cards exist in.

I think those 8 tiers can be distilled down into the following card contexts:

• WISH – expressing the desire to be “more”, in what way
• VEHICLE TARGETED – identifying, assessing, studying the likely thing that will get you the wish
• VEHICLE ACQUISITION – the process of sourcing and acquiring the wish vehicle and putting it at your disposal
• LEARNING – learning how to use the vehicle, learning the procedures around it, wrapping your head around pieces
• INTEGRATION – the vehicle, under your control, produces something that grants your wish. It works! Just needs work.
• MASTERY and RECOGNITION – the vehicle, under you control, is producing high-quality and desirable results, which other people want
• WISH GRANTED – the vehicle has brought you to where you wanted to be. Congratulations!
• REPEAT – the next big thing on the horizon, which you couldn’t see until now.

The cards themselves are probably the second tier: vehicle targeted. The WISH level should be maintained elsewhere, part of the fruit orchard of possibilities we cultivate. So the couplet is “I wish I was…” followed by “I need this to do that”

ACQUISITION, LEARNING, INTEGRATION are the next pieces. These probably require their own card, which suggests that WISH CARDS and VEHICLE CARDS also exist. Multiple things might need acquisition, as do multiple learning goals. Integration, at minimum, is one thing talking to another to produce a useful result. There are several kinds of things that can be acquired: formula, recipe, method, resource, machine, expert, training. The distinction I should make is between PEOPLE resources, CAPITAL resources, RECIPES/PROCESSES…

MASTERY and RECOGNITION are REWARD CARDS. They tie back to the original WISH card somehow. Maybe they are stickers or stamps instead.

ABORT ACTION cards or stickers exist to cancel a project that proves untenable. Perhaps DECISION cards exist as well.

The overarching context is the WISH. It might not be a card as much as it is a container that holds the other cards. Or it’s a bigger card. Any task that’s dreamed up is tied somehow to a wish, and having a good collection of wishes is probably an excellent way to start mapping one’s life balance.