One lesson and one puzzle from running my first writing workshop

Plus the work that students published

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EVERYTHING WAS RUNNING SMOOTHLY until the end of Session 4 when I received feedback from the students: We were jumping too quickly into Session 5 when they still had important questions unanswered—How should they tie their diffuse ideas together? How do they know which ideas to develop further? How do they pin down their main point?

I had named my six-session workshop Full Cycle Writing to represent the six distinct stages I’ve seen emerge in my practice:

1. 🍭 Curating an information diet

2. 💡 Developing ideas

3. 🎯 Writing ‘the what’ (the substance)

4. 🎨 Writing ‘the how’ (the style)

5. ✨ Polishing

6. 📣 Publishing

But their feedback revealed the flaw in my vision: The part of writing that is arguably the hardest was surprisingly absent¹ from my session plan—and I was expecting the students to figure it out on their own.

Their feedback saved me, because whilst they were busy wondering how to move forward, I was busy panicking, unsure of even how to design Session 5 at all². I was grappling with the same thorny questions as they were, I just didn’t know how to articulate them.

It was only when they spoke them aloud that I was able to understand my confusion and start taking steps towards figuring it out.

The big lesson I learned about writing from trying to teach it

The breakthrough came when I put on my editor’s hat. As the dedicated Writing Mentor at David Perell's Write of Passage school, many writers have told me that my feedback is unique (humble brag: I scored 60/60 on the school’s editor training program), and so I put session-planning aside, sat staring out of the window, and asked myself, “What do I really think about when I think about someone's draft?”

I realised that there are some fundamental questions that I tend to ask:

• Does all of this [the topic, the argument, the content, and the author] add up?

• Can I easily say why I think they are writing this particular piece at this time?

• Can I easily tell what I think their beliefs are about the topic?

• And what is it I think they want me to do having read it?

Because the truth is, if you show me any quality piece of nonfiction writing, I'll show you an author who has answers to those questions. They know why they're writing it. They know what they believe. And they know what response they want from you.

This insight was how Session 5 was saved from disaster, and it’s what gave rise to what I’m calling the Strategic Questions.

The Strategic Questions for writing nonfiction

1. Motive

The first question—Why are you 🫵 of all people writing this piece now?—is crucial because there are probably myriad reasons you're doing it. Are you letting yourself off the hook? Punishing yourself? Trying to heal? Understand? Teach? Knowing your motive helps you make key decisions about what to say, and how to say it. It's the writer's version of what Simon Sinek calls having a why, and you shouldn’t leave home without it. Having a why makes everything that follows—all the drafting and all the editing—a fuck ton more manageable.

2. POV

The second question—What do you believe about this topic? [which I suggest writing as a series of “I believe…” statements]—reveals all of the ideas you can write about confidently, as well as creating options for how to make those arguments. It also exposes those ideas you’re less convinced of and should therefore dig further into, treat with more humility, or leave out altogether. Knowing which hills you are willing to die on will help you nail your main points, and add more clarity and energy to an often bewildering and demoralising process.

3. Job

The third question—How do you want the reader to respond?—will help you decide on the job of the piece. Your words can do broadly three jobs: Affect what someone thinks; affect how they feel; or affect what they do. So what impact do you really want to have? Change someone's mind? Nudge them to act? Inspire a story of their own? Whatever it is, I wouldn't recommend having too many intentions. But being clear on them will help shape the form you choose, the tone you use, and make editing less challenging too.

You can ask yourself the Strategic Questions at the start of a project and throughout. You don't need to answer them linearly; it’s better if you cycle between them; as you answer one, it will help you answer the others.

The Strategic Questions are rationalising tools. They may not be easy to answer. And they’re not always fun either, especially when what’s most exciting about writing is often its irrational and intuitive promise.

But they have genuinely been, and continue to be³, one of the sharpest writing tools I have gotten a handle on. Here’s the quote I chose to encapsulate Session 5, with a new design based around the Strategic Questions:

“Strategy without tactics is the slowest route to victory. Tactics without strategy is the noise before defeat.” – Sun Tzu, Chinese military general, strategist, philosopher, and writer.

And here's something else that wasn't obvious to me: You may think your answers to the Strategic Questions are somewhere in the void, hiding from you and resisting your grasp. But they’re not. You can just decide, right now, what the answers are going to be—and then run with them! You're in control.

And you know what? There's great pleasure in deciding 🤗

Students’ work

Not all of the students at the workshop worked on a single piece of writing throughout; many of them chose to view the tools in each session as tools they could apply to any project any time.

But the students who did develop a single piece published it together the other day, and I'm sharing their work here, in no particular order.

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In The limits of DEI: anyone can abuse their power, not just white men, Radical Radha shows how DEI programs can often exacerbate the very problems they seek to solve. I like the way Radha is so clearly thinking in public, by sharing the fact she revised her ideas after getting feedback.

Indians with citizenship exploiting other Indians is par for the course - it happens here and in India. It occurs in every country! Technically, such behavior should count as discrimination based on national origin and immigration status, but no one notices or cares because Indians are doing it to their group.

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In Words that wait, Claire Coley points out that too often we judge the effectiveness of our written work across too short a timespan—the things we write today may make their true impact later. I find that thought both comforting and inspiring!

Our words have longer lives than our experiences. Whether it’s a perspective on grief, the midnight struggles of a new parent, or a guide for young leaders, your words carry meaning. Trust that they will find their reader when they’re needed most.

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In On the Verge of Authenticity: Embracing Your Self, Ezra David writes about the psychologically turbulent yet poignant journey of discovering more of who you really are, weaving together essay, memoir, confessional, and art into a touching and memorable piece.

Do you know the feeling, when you listen to a song or an album on repeat and then you forget it for a year or two and then you listen to it again and suddenly you realize that the song had all the answers you needed to hear, but couldn’t?

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In Your Awkward Voice Matters, Sarah Seeking Ikigai writes about the lack of male voices in the important discussions she has about gender inequity, exploring how we might invite more men to contribute, even when their ideas are imperfect.

To my male friends reading this… your voice matters, even (especially) when you're not sure what to say. Perfect silence helps no one. Imperfect allyship moves us all forward.

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In Your calendar is a guide, not a dictator, Matheus Felipe gives us an inside look at how he’s setting up his calendar to feel more productive and less bossed around. It was a good reminder that there’s a bunch of stuff in my own life that I could probably chunk together and not feel so intimidated by.

There’s a lingering feeling of anxiety and fear with following a schedule. It’s like you’re being ordered around by your older self who made that plan, who had the expectation of completing everything in it, ignoring what possible situations could arrive in the future.

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And in At 110-years-old a Galapagos Giant Tortoise proves age is just a number!, Karena takes us to the Galapagos, where giant tortoises and sea turtles reveal unexpected lessons about energy, aging, and adaptability. It’s a piece about nature’s quiet wisdom—and what we might learn from it!

Mating season is a few weeks away and I guess the ‘young’ buck was practising. A few snarls later, and watch the speed on that 110-year-old!

The puzzle at the heart of the Strategic Questions

The thing I can’t work out is how to balance intention with chance. Many great writers, from George Orwell to Joan Didion, have championed writing’s ability to literally reveal to the writer what they believe. But surely writing can only do that if we approach it with an open mind free of objectives and certainties. So what role does strategic questioning play when it comes to the more exploratory, revelatory, and surprising parts of writing?

That’s all folks!

If you like the sound of what went down at the workshop and you’re interested in joining the next series, send me an email, letting me know what you’d be interested in learning. And I’ll see you in class!

Harrison 🙋‍♂️

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Previous post

1. Maybe it wasn’t so surprising after all. Maybe my brain skipped it because it was so hard.

2. I didn’t design all the sessions upfront; I designed them each week one-at-a-time. This was the advice my mentor John gave me, and it allowed me to be flexible in my approach.

3. If you’ve got an hour on your hands and you want to watch me draft an outline from scratch using strategic questioning, I made a recording of me doing that.