How To Author Like a Strategist, Part II: Execution

Start small, fail fast, beat procrastination.

This is a 10-minute read. You may need to sit down.


In last week’s letter, I focused on the first tenet of strategic project culture (especially if you’re an author or creator of some sort): Planning Meticulously. We’ll now examine the second: Executing Immediately.

So you’ve laid out your Very Malleable Plan. The next step is surprisingly simple: start.

I can hear your sharp intake of breath. “Just dive in, you say?” to which I respond, “What exactly is the value in waiting?”

If you do not yet have a solid, meticulous plan, then waiting until you have one definitely makes sense. Ditto if you don’t actually have the resources to begin your project. But if you’ve put together a plan, and that plan includes a way to obtain resources to kick off the project, then guess what? Obtaining resources is executing the project!

So, instead, here are the two questions you should be asking:

  1. Where/how does one start executing?

  2. Why immediately?

Execution: Where to start?

If your plan involves resources you don’t already have, you might need to start by obtaining required resources using a checklist. These resources could be tangible or intangible, people/team or equipment, space or money, etc. Whatever it is, nailing them down for the duration of the project is key. As an author, here’s my personal checklist of resources for a new book project:

  1. Writing stuff: PC, external keyboards and phone/tablet stand ( I write on the go a lot and like to switch things up), stationery (pens, sharpies, highlighters, sticky notes, pads, notebook, etc), research materials (and storage for easy retrieval), etc.

  2. Non-writing stuff: Music (headphones, speakers, playlists, streaming service subscription, etc), writing software (I use Scrivener and Google Docs/Sheets), cloud storage space (I use Drive for backups), etc.

  3. Space considerations: Furniture (esp desk & chair), light (natural or otherwise), heating/cooling (and clothing), etc. (If you write outside often, and if you’re involved in parental or familial care, this is where to factor those in.)

  4. Health & nutrition (important!): Water & water bottles (or at least access to water), other beverages (hot & cold), fruits & snacks, food, exercise equipment (I bike often to take breaks, for instance), etc.

Some of these things I already permanently own or have access to, while others I tend to renew often or per project.

Once you’re done obtaining resources (and sometimes, even before you’re done), executing the actual project itself is dependent on the exact project and how you’ve planned to go about it. This can take any number of forms, so I won’t go into that. What I will note, however, are some of the challenges—a few of which I’ve faced myself—that often occur at this initiation stage:

  1. Inertia/slow start: You’ve started, but OMG it’s like pulling teeth! Nothing is picking up momentum, everything is a drag.

  2. Procrastination: You’ve put everything together and are ready, but somehow, getting your actual foot on the gas is super hard. For some reason, you’d rather do anything but this project.

  3. The plan is…wrong: Yup.

  4. Oh, this project is waaayyy bigger than I expected: Also yup.

And these, friend, make the perfect case for why you need to start immediately.

Execution: Why immediately

If I’ve got a solid, adaptable plan, and I’ve got my resources, what exactly am I waiting for? Heck, even if I don’t have my resources down pat but my plan tells me when I’ll need them, I can procure what I need now and obtain the rest along the way.

I think of starting immediately like trying on clothes for a forthcoming event at the store. You don’t take them home and then try them on for the first time one hour before the event, do you? You try them at the store, immediately. Because you want to be able to swap poor fits for something else, or have time to fix an item you really like. You want to walk in it now and know if you’ll be able to spend two hours at that soirée without the waistband eating into your skin. You want to know what challenges you may face so you can adjust for them as soon as possible.

Another reason you want to start now is to give your plan a chance to fail early. Again, think of this as taking your clothes home and trying them on around the house, just to see if they’re too tight in the armpits and figure out how many times you can raise your arms in greeting. Then in the course of doing this, the shirt actually rips. Great. But now, you still have time before the event to fix it, or get another shirt. You want your plan to fail fast so that you have room to bounce back and adapt.

And then the best reason to start now: to beat procrastination. So long as a project is dear to your heart, it will always be challenging to get over your fear of doing it. Heck, I feel the same trepidation before I start writing every new book, even if I’ve just finished the last one. We all harbour innate fears of performing poorly, taking on the unfamiliar and uncomfortable, or starting out the wrong way. Our body’s flight response simply nudges us toward not starting instead. Starting sooner than later leaves less room for this (usually irrational) fear to grow and become insurmountable.

Tips for executing immediately

  • Start small: One of my best writing tricks is to start with easily beatable periodic (daily, weekly, etc) word counts. Time has taught me that my optimum writing time/word count is about 1-1.5 hours or 600-1000 words a session. But at the start, I set 30-40 minutes or 350-500 words instead. Surmounting small goals increases your confidence, helps you establish a routine, and reduces the impression that you’ve taken on too much. Starting small also helps you keep in mind that the project is a marathon, not a sprint.

  • When in doubt, gain clarity: Another cause of procrastination is the feeling that you don’t have the required knowledge to begin your project. Well, why not start by, (A) knowing what exact information you lack, and (B) deciding how to gain that information? A good way is to do a small test. For instance, if I think, “I don’t know enough to write a novel set in 1945 Paris,” I can start now by writing a small scene or two that, in the course of writing it, immediately gives me an idea of how much I may need to know about 1945 Paris. After this, I should be more informed about what I’m missing and how I may tackle it, both of which reduce my fear.

  • Look your fear in the eye: Shying away from the fact that you’re scared to start is counterproductive. It’s better to ask yourself what exactly you’re afraid of. I often write sticky notes of doubts over about my current project and place them within sight of my desk. They read something like, “I’m afraid this book requires so much worldbuilding that I’ll be unable to make up enough new things or keep track of everything.” Not only does looking at that note every day reduce my fear of that challenge, it helps me isolate the two problems that may need fixing: finding new ideas and keeping track of my world. And naming a problem is halfway to solving it.


What did I miss? Hit me in the comments below 👇🏿 with any questions, additions, alternatives, whatever. I’m always happy to hear from you!

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Catch you over at Part III: Failing Swiftly. Ọkhionwiẹ!

Suyi. 🧡


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