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10 steps to Reverse Engineering Good Writing

Decoding Greatness, is a self-improvement/strategy book by Ron Freedman, Phd. Here I have adapted the framework specifically towards the craft of writing.

Friedman’s book offers a systematic approach to developing expertise that is generalizable to many achievement-oriented fields, including creative writing. The framework is familiar to anyone with formal education or training, and may be especially valuable for those without access to that kind of training (or early in that path).

1. Become a collector of others’ successes.

Image by Nino Carè

The great adage for becoming a good writer is to first become a good reader. You must be moved by the sorcery of others’ work, motivated to collect and admire it.

“The first step to achieving greatness is recognizing it in others,” says Freedman

Though I grew up as a compulsive reader, for several years this habit faded to primarily the infinite scroll of the internet. One effective strategy as been to yoke reading with incentives. Specifically I used the app Goodreads to give myself yearly “reading challenges” and aimed for shear numbers. Book clubs can also incentivize reading and connection. Finally, i found I can get ebooks and audiobooks through my public library, which decreases the barrier for trying out a book compared to buying one. My intake remains modest, though I am still able to identify the kind of things I like and don’t like, which also means identifying the kind of thing I want to write.

Hot tip: Read literally for the numbers or for a book club and the peer pressure. Give yourself the gold stars or whatever incentives with which you can bribe your short term pleasure centers until you can reconnect to the long-wave joy.

2. Determine what makes each unique.

Image by MonikaP

“What’s different about this example?” As you collect books and pieces, identify one thing that separates it from the other works you have consumed.

This was a revelation — it is not merely the passive devouring of books but the study of those books. This is a major part of formal creative writing curricula, to read like a writer.

I do this step literally — I write a single sentence about every book or good essay i read, to articulate what I value — which also creates a “search term” to name the thing that is so compelling (and subsequently reconstruct). This is another place in which community can make a difference — discuss and debate a book with someone else.

Hot tip: Make a spreadsheet or journal that tracks one sentence answers to the what is unique about each book or piece you have added to your collection.

3. Think in blueprints.

from Kimball Art Center

Another revelation for me: literally outline a thing you just read. It is the equivalent of taking an engine apart, dissecting a cadaver etc. Suddenly the skeleton of the thing lights up (learn enough to identify your own tortured mixed metaphors).

I am not sure how this would apply to something like poetry, but in nonfiction, patterns quickly emerge: e.g. opening with a vivid narrative, or the structure of an op ed. Fiction utilizes story structures that have been studied since at least Aristotle. You then can quickly recognize the components in future works you read. You can also identify the way that authors may break the structure, and can study whether it is effective or not.

Hot tip: Make a one page outline of a single book or piece you admire. Then do it again and again. I would add, after doing this a few times, look up the formal theory or background to the genre in which you write to provide a language to make sense of your blue prints

4. Don’t mimic, evolve.

Image by Brigitte

“Immature artists borrow, great artists steal,” is the catchphrase attributed to Faulkner, perhaps apocryphal. This one is hard to be precise about, but perhaps also the most intuitive. Don’t be hack. Metabolize the works you admire and remix them with all the other things in your brain. This is not a task but a practice over time, like painters who copy multiple artists, then eventually start developing their own style. This is what you are doing in the work of writing work— you have taken apart the machine, now replicate it until it is internalized. It is marking the knowledge into your body

Hot tip: No short cut here. You copy many good works (imitate voice, structure, other techniques), but don’t stop there. Continue until it is in your nerves and muscle and bones, then your body will magically remix things, like it magically makes poop and grows babies.

5. Embrace the vision-ability gap.

Image by Maryam62

The difference between one’s own clumsy attempts and the polished final product of a master is vast and humbling af. It is a vastness to which I have often approached, then ran away from. This is treacherous grounds for the perfectionist. The pursuit of expertise requires acknowledging the mundane truth that it will take you time to get better at a thing. In addition to getting a good therapist, give yourself grace to suck, knowing you will get no where unless you start.

Hot tip: Embrace the Shitty First Draft method by Anne Lamont. Cultivate beginner’s mind and humility. (Write awkward medium blog posts as you train your body to do the thing.) Find a good therapist if you can.

6. Keep score selectively by measuring the key elements that drive success.

Image by Maximilian Fritsche

Post-industrial late capitalism LOVES metrics. Freedman is thoughtful about how metrics can be powerful and potentially misguided. It is critical to identify appropriate measures. (For a case study in metrics gone horribly awry, Freedman describes the grotesque mis-steps Wells Fargo took)

In the course of my work in implementation studies, i would add that there are two types of metrics: (1) outcome metrics and (2) process metrics. An outcome metric is coupled closely with one’s actual goals. Example in writing craft include the number of articles published; chapters drafted towards a book. Process measures are something like —how many days in a week you completed morning pages; tracking your collection of other’s successes; the minutes you sit in the chair to actually write.

Hot tip: pick a single process and single outcome metric per time period to focus on. If you are starting out, it’s fine start modest to just build the habit. E.g. this quarter I have focused on (1) submitting one article and (2) check-boxing every day that i spend even 5 minutes writing.

7. Take the risk out of risk-taking with diversification of potential applications.

Image by Steve Watts

Surrounded by a Just Do It culture that celebrates reckless economic gambling, it did not occur to me that most shrewd businesspeople, per Freedman, constantly modify their risk. Rather than a binary take on risk taking (also a perfectionist tendency), Freedman identifies ways to take risks prudently.

Another way to frame this is that getting better at anything is a series of progressive experiments. You don’t do one giant experiment that consumes all your resources that wipes you out. You try a few things out in low stake settings so you live to try another day. For writing, you can write anonymously or with a pseudonym, or hash out ideas in frequent blog posts (hi) before developing them into formal article submissions.

Hot tip: Breakdown risky moves into smaller experiments that can give you feedback and data. Write under a pseudonym, keep a blog, show your article to friends first before submitting.

8. Distrust comfort.

Image by Juraj Varga

Acquiring skills is not easy, it is uncomfortable. It is a corollary to step 7, even though you modify risk, you should still be pushing yourself to take the risks. I disagree with urging people to “never” be comfortable, as it also feeds into the workaholic, perfectionist neurosis of our culture. It is ok to be comfortable in the sense that it is ok to rest, step away, not internalize failure as being about your essential nature than about what you are doing. I think a better way to frame this is that if you are very excited to get better at something, embrace the restlessness and curiosity it inspires in you. I think the real thing to look for here is not discomfort but boredom. Boredom is an interesting marker to ask yourself whether you are done doing a thing (which is okay!) or whether there is a new direction you would like to explore.

hot tip: You honestly don’t have do anything other than survive and be good to others. Often surviving in our culture requires grinding, but if you are developing work you hope will transcend the grind, pay attention to boredom. If you are no longer motivated to evolve, step away for a break. If you are still not moved to continue exploring and experimenting in a given direction its ok to follow your curiosity to something else that sparks joy. Trust yourself and live a life that allows you to attend to your perceptions

9. Harness the future with reflection and illuminate the past with analysis.

Image by Couleur

Hippocrates’ legacy is mostly a collection of aphorisms, one of which is “declare the past, diagnose the present, foretell the future.” The revolution that Hippocrates brought to the healing arts is taking notes — history is a clue to the present and future. To consciously build something like expertise or a body of work, you need to know what you have done so far, and where you intend to go, which helps shape your experience moment to moment.

I write not only the writing i wish to write — but I write about the writing, small observations about what it feels like and what efforts i have made. This is like the qualitative version of metrics. Journal each day, even briefly and revisit the notes (Freedman recommends a five year journal), a type of lab notebook of your process. This allows you to appreciate how far you have come, internalize hard-won lessons and a direction in which to go.

Hot tip: process journal. Literally run a google doc with an ongoing dated log of things are going and what you have tried, like a lab notebook.

10. Ask others wisely, with questions that elicit both elaboration and clarification

Image by F. Muhammad

Experts are not the best at explaining the things they are experts at. By its very nature, expertise sublimates formal training into less-cognitively accessible subconscious processes. Freedman identifies questions that can try to get around that to get concrete advice from experts.

I would add a lesson from academia and medicine of “intermediate mentors.” There is the master clinician, but also a hierarchy of experts who teach each other. The intern instructs the medical student, the senior resident teaches the intern. Turning to peers and people who are just 1–2 steps ahead of yourself, who remember freshly what it was like to be in your position, can give you insight in incrementally moving forward. Do the same for those right next to you and behind you, which both reminds yourself of your own progress and builds a community. See one, do one, teach one (can sub 10–10,000 for one).

Hot tip: Ask experts for concrete advice, knowing that they may not remember anymore how they became an expert. Cultivate a community of peers who are in a similar place as you as well as a few steps ahead so that you can ask them advice and reciprocate.


A journey to build or learn something begins in the energy of eros — it is exciting, fresh, addictive, enamored with possibility. When it comes time to actually do the thing — it can still be exciting! This type of reverse engineering strategy keeps the excitement alive by laying out a systematic guide with a series of puzzles, problem solving and immersive practice. Each of the 10 steps has a concrete actionable item to organize your efforts.

I would love to hear if you have any insights, feedback, recommendations or personal revelations about any of this.

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