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Connecting Strategy to Tactics

Like a lot of people reading this post, I have many, many ideas going on at once and many, many tasks that need my time and attention, both of which are in short supply. Recently, I’ve been cleaning up files and cleaning out my Dropbox and found countless lists and documents and mind maps signifying repeated attempts to wrap my head around big, complex issues surrounding work, web strategy, and my life in general.

Screenshot 2014-04-29 14.36.03I’m a list addict, I’ve come to terms with that, and I would argue that writing it all down is better than not. I don’t do obsessive digital organizing to remember everything, it’s not memory that’s an issue for me. My hope is that I get it all down on “paper” and these disparate pieces will align themselves and I can find some priority therein. This is typically a false hope.

After putting everything together on, say, a complete sales strategy for a theme, I end up with this huge list comprising many components, each representing a week or more of work. I feel good about the overall plan but I find myself at a loss of where to start. I could just pick something and go but the lists and plans I end up with are not concrete tasks, they’re concepts and areas of focus.

This is where the good feeling wears off. 

These pieces are so big and complicated, I’m not sure what to do to address each one. Thing like “create content” is a single component, sure, but it’s a massively complicated one. Where do I start? I have tasks for specific blog posts and I feel good about those but if I start promoting, shouldn’t I be careful about what I’m doing? Shouldn’t I make sure my actions are leading to sales and not just crossing things off of a list? Is it wise to move from “create content” directly to “write a post about RSS feeds?”

This is where I start to stress out. I’ve got time left today to work on it but I’m paralyzed. All these huge pieces looming, hundreds of hours of work in total. Where do I start? What do I do? The anxiety builds and I find myself reading online articles about productivity and finding some useless task to fill my time. Where is my direction? What happened to the plan? I’m nervous and irritable, the plan is causing stress and distraction rather than clarity. What am I doing wrong?


I recently went through this whole process for the aforementioned online sales strategy for WP-Drudge, a theme I sell online. I was determined to take the big, scary picture in my head and parse it into a priority list of tasks to complete. I have always been good at big picture thinking and I’ve also been good at breaking things down into actionable tasks but there was always a disconnect between the two, especially on my own projects.

I decided to get to the bottom of what I was feeling and experiencing by writing my way through the process. I found the whole thing very enlightening and thought others would as well.

This is what I thought the problems were:

  1. Lack of time … all this work and a limited number of hours in the day. The stress came from the tasks piling up as the clock ticked.
  2. Poor strategic thinking … I wasn’t focusing on the right things. My lists were incomplete and my logic was flawed.
  3. It’s hard for everyone … this is not an easy thing to do, it’s hard for everyone, myself included.

I think the above are all problems but they were not the problem I was having. The problem I was having was simple …

I was skipping steps

At every point, I was jumping around from big picture to task assignment back to big picture, then huge picture, then the nitty-gritty details again. I would start with “what do I want out of life,” which is the biggest picture of all. Then I’d get to somewhere familiar, like this sales plan, and find myself adding granular to-do tasks: features for the new version, marketing I wanted to look into, analytics programs to try. Then back to the huge picture and get to, say, house projects. Now I’m looking at fixtures for the bathroom and trees for the yard, adding up prices, sending links to my wife. Now back to the huge picture.

This was making progress, in a way, but it wasn’t much. It did something worse than that, though. It didn’t just keep me from making progress at the time, it hindered me from making progress in the future and contributed to a strong feeling of overwhelm.

Here’s what would happen, this might sound familiar:

I would get or make a spare hour or two to work on a project. I’d sit down and look through the tasks I had and thought “none of these are high priority.” If I was feeling unmotivated, I might just pick one of these (install some new analytics suite, build out a quick feature) and go with it. Usually, though, I’d consult whatever crazy list of mind map I had for the project. I’d see all these disparate pieces and projects and have a tough time getting back into the mindset of the project. By this time, an hour had gone by and I’m nowhere. I’m back to being stressed out and irritable with no progress made.

Time wasted. I should have read a book or gone for a walk.


Every time I sat down to get something down, I wasn’t realizing that I had never connected my strategic thinking with my tactical actions. The strategy was good but unfinished. The work on tasks was also good but it was unfocused. I was missing a big, important step in between having an idea and making that idea come to life. 

The strategy stopped when all the different components were listed but that leaves me stuck when it’s time to get something done. It’s not hard to write down “pick keywords for blog posts” or “address demo situation” but when I was ready to take some action, I have to get back in the context of the plan I created in order to create tasks. This context takes time and a different style of thinking. If I have to do this each time I want to get something done, I’m losing a lot of time and I’m creating internal tension by switching between these modes.

This time around, notepad at hand to record what I was going through, I started with a high-level plan spawned from a very simple goal: sell more of these themes. Then I broke that down into components: increase traffic, increase conversions, and improve the post-sale and support process. Simple stuff but still too high level to act.

Then I broke each of these down to their individual components based on what I’ve seen succeed on the site and advice I’ve heard from others. The individual components are not important for this example and will be different depending on what you’re looking to accomplish.

I kept drilling down on each piece until I got to a point where I said “I could write a to-do list for this.” That was the litmus test for whether the strategy portion was complete: do I have enough information to act on this right now?

I did this for each individual component, stopping before I actually created lists of tasks. By working through each piece until this point, I was connecting the high-level strategy to the steps that would be taken to execute that strategy.

But what about the tasks?

The last thing I did, when this planning exercise was complete, was to pick the one segment that I thought was the highest priority and create a list of discrete tasks. I use Asana for this but the format doesn’t matter. I captured all the tasks that needed to be finished for this segment to be complete for the time being. I made sure the tasks were ordered correctly, either by priority (most to least important) or by sequence (each task relying on the task before it).

By creating one big master plan all at once, drilling down through the segments that make up the plan, and ending with a single list of ordered tasks, I created an easy place to start. I could start right then, if I have time, or I could start tomorrow or next week but the “what should I do” question is answered and the motivation to pick that up and go is much higher.


A few important take-aways for me:

  • My inability to get started was not related to laziness or lack of motivation, it was an inability to work on tasks that felt like they would accomplish anything. Looking at a task like “write blog post about XYZ” is simple enough to do but if I start asking “wait, why am I writing this post” and I don’t have a quick answer, the drive to get it done is little to none. If I can look at that and remember “I’m writing this post to test this component of the system and to help this user, as well as improving SEO for a specific term” then I see why that work is important.
  • Creating a plan is not just as simple as getting all the stuff down on paper. That’s a great first step and seeing it all in one place is helpful but that’s only the beginning. With the context of that plan in my head, it’s much easier to break the pieces down further and further. The reason I only created a single list of tasks is because that one list covers about 6 – 8 hours of work. If I created lists for every component, I would be completely overwhelmed by the impending work that needed to be done.
  • I like the GTD model of collecting everything but, for someone working on a large number of projects, all those tasks combined creates a very heavy cognitive load. With 20 lists of 20 tasks a piece, you have 400 outstanding things to do. If each thing takes even 15 minutes, I’m at 100 hours of work, 2 weeks of hard, focused, productive work with no interruptions. What if I learn something in the process? I have to manage each of those lists to keep up to date.
  • Creating a single list for a single project component also helps me create a sense of commitment. I’ve committed to addressing one problem that contributes to the whole. If I’m wrong about the priority of that component, that’s a different problem but I’ll be working towards resolution of a single problem, which creates better output and better focus.
  • I had to respect the planning portion by giving myself a couple of hours of focused time. No email in the middle, no task list creation, no development. Once I choose a component, I might reach out and do a little research to see if this or that task is possible or how difficult it would be but that discovery happens after the whole plan has been written.

As an aside … I have not journaled in over a year. I write so much “official” communication between emails and technical documentation that I rarely find the time to just write about what I’m thinking. Looking back, I realize that I have worked through a lot of internal obstacles and challenges by doing this, I’m a little surprised that it fell off for as long as it did. By just writing without regard for who would be reading lets me be honest, egotistical, self-deprecating, and, most importantly, introspective. Pick your worst flaw, the one you hate about yourself the most, and just start writing about it; I think you’ll be surprised by how much insight you’ll gain.

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