In the early, hopeful months of a year not too long ago, my friend Lindsey and I found the key to being the organized, calm, put-together people we knew—deep down—we could be.

We were going to get our shit together. This was the year. We could feel it.

We were going to stay on top of laundry and cleaning and chores and yard work and hobbies.

We were going to plan—and execute—enriching and educational activities for our children, without executing the actual children.

We were going to meal plan. Like, for real this time.

We were going to reach our goals, learn new stuff, make more money, be more attractive, and generally become much better people.

We were going to wear actual outfits, not just hoodies and jeans.

(Okay, maybe not on that last one. How can you improve on the hoodie-and-jeans combo? You can’t, that’s how.)

We knew we would do all this because we had found the key.

The missing ingredient.

The tool we’d always needed: a perfect, detailed, customizable, perfect-in-every-way planner.

I’ll spare you the details of what we collectively spent on the planners and the required supplies to properly use them. You know, basics like pens and markers and highlighters and stickers and washi tape and bookmarks and stencils and pouches to hold all the supplies. First, I don’t remember exactly how much we spent and second, I don’t want to remember. Let’s just say I probably could have bought several new hoodie-and-jeans combos instead.

Nice hoodies, too.

We got our planners. We filled in our planners. And we used our planners for… Well, we used them for a while. We used them long enough to realize that the magical planners were not going to magically transform us.

In retrospect, this seems obvious. But at the time, those planners seemed to hold the key to success. They were the clear path to a calmer and more fulfilling life, the instructive map we could lay gently over the roiling landscape of our lives. These planners would save us.

It was a sure thing.

Until it wasn’t. Until our beautiful planners met reality, and reality won. I’d like to say I learned from this experience, but I’m still learning. I still expect my plans to save me from myself.

I still fall, often, into the pitfalls of traditional planning.

And I still spend too much money on fine-point pens and washi tape.

The five pitfalls of traditional planning

1. I get lost in the details

Sometimes I get lost in the details of the plan itself: what are the best tactics? What’s a realistic timeline? How can I improve? How many resources do I have? How much information do I need before I can get started?

Sometimes I get lost in the details of how to plan: what tool should I use? What’s the best way to present this plan to others who are involved? How can I keep the plan front-and-center? How can I make planning a more efficient part of my workflow?

Both are ineffective uses of my time.

How do I know? Because even if I find the “right” answer for all of those questions, it won’t make a significant difference in how well the plan works. Getting lost in the details means I am spending energy on information and actions that don’t help me make progress toward the goal.

Skip the pit: require every part of the plan to be helpful.

Helpful: the information, guidelines, and resources are useful and valuable when I am executing the plan.

When I’m out there in the real world, taking action, moving in space-time, interacting with people, dealing with the unpredictable, will this part of the plan be helpful? Or will I quickly pass over it as irrelevant and find the nugget that is helpful? I can save myself from poor planning by skipping the irrelevant details and focusing entirely on those gold nuggets of helpfulness.

Questions to ask for helpfulness:

2. I try to plan all the way to the finish line.

The finish line is the goal, and there are two reasons that planning all the way to the finish line is unhelpful.

First, I often try to plan for a goal that’s too big. Now I don’t mean that my goals should be small. No way! I LOVE AND ADORE BIG TERRIFYING GOALS. But planning for an enormous far-away crazy big goal means projecting myself way too far into the future. The finish line for big goals is too far away for my plans.

I don’t need to plan for the entire goal: I need to plan for a slice of the goal, the slice I’m focused on now.

Second, I often try to plan every step I’ll take to reach the finish line. This is silly. Things will change too much along the way. Reality is like that, all by itself. Plus, when I start taking action, I affect reality. I change things. I open new doors, I make new connections, I increase my skills and capacity. Trying to plan every step—when I’m at the starting line—is a limiting exercise that reduces my options rather than increases them.

Skip the pit: require every part of your plan to be flexible

Flexible: can adjust to what actually happens without losing its value or usefulness.

Building flexibility into my plans forces me to remove the rigidity and absurd overplanning I tend to do, and make sure that the plan can work in space-time reality. After all, if it can’t, what’s the point? If I think about how my plan can adjust to life as it happens, I’ll find simpler ways to accomplish things. There’s no point making things harder than they have to be.

Questions to ask for flexibility:

3. I get lost in potentials

And thanks to my capacity to imagine 27 worst-case scenarios in less than a minute, I have plenty of potentials to think about. Mostly negative ones. There’s wisdom in anticipating likely obstacles. There’s wisdom in preparing for challenges. There’s not wisdom in anticipating all the negative potentials, all the off-the-wall obstacles, all the unlikely scenarios I could face.

The best preparation for potential obstacles and challenges are these two firm beliefs:

It’s also easy to get lost in possibilities, side effects, rabbit trails, and connections or opportunities that may arise, if I’m successful in executing my amazing plan. It’s easy to focus on a piece of the bigger goal that isn’t relevant. Great big goals are inspiring and good, but when making a plan, I need to focus on the part of the goal I can achieve now, and leave the rest of later.

Skip the pit: require the plan to be focused.

Focused: has clear boundaries and a precise definition of what’s relevant to the plan, and keeps attention steadily focused on the relevant piece of the goal and how to achieve it.

Keeping a plan focused starts at the very beginning. If I’m trying to plan for a goal that’s five or ten years in the future, I’ve already failed. That’s too far away to plan for. It can be a vision, an overarching and motivational goal, but I need to plan for the slice of the goal I’m going to achieve now, not five years from now.

Questions to ask for focus:

4. I spend too much energy optimizing

Optimizing is trying to find the best way to do something: the most efficient and most effective approach. The highest quality tool. The method that achieves the best output most consistently.

There are a lot of superlatives, unspoken, but present in optimizing: best, most, highest, soonest.  There can also be negative superlatives—least, for example—laying on additional burdens.

The result is a set of impossible standards that I’m trying to meet in pretty much every aspect of planning. I don’t just want a good tool: I want the best tool. I don’t want to reduce risk: I want to reduce risk to the least possible amount.

Optimization can be important in certain areas, but it is not important in most areas. In most areas, good enough is good enough. It’s better to use a good-enough tool, complete the task, and keep moving forward: this is progress. Progress is what leads me from the starting line to the finish line. I need to optimize for progress, not perfection. And if I can’t tell the difference, maybe I shouldn’t try to optimize at all.

Skip the pit: require the plan to be powerful.

Powerful: makes a meaningful/positive difference when I encounter confusion, uncertainty, or unpredictable situations as I executive the plan.

Mental models are powerful. Questions are powerful. Clearly defined standards are powerful. Flexible tools are powerful. Overly specific instructions, not allowing autonomy, and needing to know everything in advance, on the other hand, are not powerful: they are limiting ways of operating. If I’m trying to micromanage every single thing, I’m not planning. I’m controlling (or trying to). It’s futile, so I might as well move on.

Questions to ask for power:

5. I ignore my own problematic patterns

This is a biggie.

My own biases, expectations, unverified assumptions, and errors in belief—plus unproductive patterns of behavior—can destroy the best plan.

When I’m making a plan, I tend to do it in a vacuum: a theoretical personality vacuum, that is. But planning without accounting for myself as part of the plan is an incomplete and dangerous plan. It’s like I plan for a fictional, perfectly balanced version of myself. That person doesn’t exist, so any plan that depends on that version of myself executing it will fail.

Skip the pit: require the plan to be accessible.

Accessible: easy to find, understand, and use in the real-world context of action and motion, by everyone involved.

I have to take into consideration how people actually act in the real world. If it’s only me, great: I just have to think about how I operate, regularly, in less than ideal situations. If there’s a whole team involved, I need to think realistically about how my team communicates, accesses information, deals with crisis, etc. My plan needs to work with the normal patterns of behavior that I (and my team) exhibit on a daily basis. If it doesn’t, I don’t have a plan at all. I have a really boring work of fiction. I could self-pub it, I guess? Maybe a new genre: “planning novellas.”

Questions to ask for accessibility:

June 26, 2019