How I approached Showing Your Work

How I used AI to actually apply a book to my life, and the public posture that fell out of it.

I read Austin Kleon’s Show Your Work! on a recommendation from the Instagram user lostandlucky. The whole book is one idea: if you want your work to be findable, you have to put it out there. Document what you’re doing daily. Post things on social media and your own blog.

Reading the book is half the battle. Actually actioning it is the harder part.

For context, a while back I had run an AI prompt on Naval Ravikant’s ideas about how to build wealth. It helped me realise that I knew how to code, but since I didn’t have any startup ideas worth pursuing yet, I should go after “media” wealth. Show Your Work! is a way to start to do this. You build wealth slowly by putting your work out there. Maybe eventually I’ll code something worthwhile as well?

This made it clear that I should go after it. Now I just needed to action it.

Using AI to turn the book into action

Step one: go over the books ideas and think about how I could apply them.

I downloaded the epub and pointed Claude at it.

I read the book “Show Your Work” by Austin Kleon. I’d like to implement some of it in my life. I’d like to capture the main ideas of the book here so I can go through each one and just think on it a little and how I could apply it to myself. The book is here: …

Claude suggested an index note plus one note per chapter. Each chapter note got the core idea, key points, quotes, and a “Reflect & apply” section for me to fill in.

Step two: fill the Reflect & apply sections in myself. This is where the real gold gets delivered. By using AI to prompt me, I’m giving it so much more context on me than it had previously.

Step three was the interesting one. I used Claude to help me pull the patterns out of those reflections:

I’ve been working through Austin Kleon’s Show Your Work! I made notes on each of the 10 chapters in my Obsidian vault, and under each chapter there’s a “Reflect & apply” section where I wrote my own answers about how the ideas might apply to my life.

The files live here:

../Projects/Show Your Work/ Show Your Work - Index.md 01 - You Don’t Have to Be a Genius.md 02 - Think Process, Not Product.md 03 - Share Something Small Every Day.md 04 - Open Up Your Cabinet of Curiosities.md 05 - Tell Good Stories.md 06 - Teach What You Know.md 07 - Don’t Turn Into Human Spam.md 08 - Learn to Take a Punch.md 09 - Sell Out.md 10 - Stick Around.md

What I want from you: help me build a concrete plan for how to start showing my work, based on the reflections I’ve written across all 10 chapters.

Before proposing anything:

Read all 10 chapter notes end-to-end. Pay particular attention to the “Reflect & apply” section of each — those answers are mine. Everything above that section is summarised from the book.

Look for patterns and themes that recur across multiple chapters’ reflections. Cross-chapter signals are stronger than any single answer.

Ask me clarifying questions where my reflections are vague, contradictory, or where the right action depends on context you don’t have. Don’t fill gaps with guesses.

What I’m NOT looking for:

A summary of the book (I have that already).

Per-chapter action lists. If multiple chapters point at the same thing, collapse them into one action.

A 6-month roadmap with 30 items. I want a small number of concrete near-term moves I could actually start this month.

Output I want:

A short synthesis (3–5 themes) of what my reflections collectively point at.

Inside each theme, 1–3 concrete actions — specific enough that I know what to do this week or this month.

Anything in my reflections that contradicts itself or seems to be avoiding something — call it out, don’t paper over it.

I wanted Claude to help me figure out some concrete actions to take based on my reflections. If there were any patterns I wasn’t seeing, I was using AI to help me find them.

What Claude told me

The six patterns claude came back with were:

My public identity is unresolved — the single most recurring signal.
I have a mountain of latent material I’m calling “obvious”.
Writing is the natural medium and I already have the engine.
I own the infrastructure but it’s idle.
Knuckleballers exist offline; online relationships barely exist.
The privacy line is half-drawn.

Claude then started asking who I was writing for. I said: “I just want to write what I’m interested in, but please be skeptical.”

Claude pushed back. It said I didn’t need a target audience. But “audience avoidant” plus “zero intentionality” equals “zero compounding”. What I needed was a posture.

Posture

A posture is five things: vantage, tone, spine, foil, promise.

I didn’t get it at first, so I asked Claude to describe the postures of some writers I already like reading. That made it click. Then we went one by one.

Vantage

An engineer-leader who keeps inheriting situations where the technical direction has collapsed.

Hands-on enough to still build (SRE → platform → Rust on Kubernetes) and people-enough to lead staff engineers and run teams (Eng Manager → Head of Engineering → Fractional CTO). Has twice watched non-technical CEOs grind down technically-strong teams from the inside. Australian tech scene specifically — Freelancer, Expert360, Macquarie, Dovetail, Slate. Writes from the seam between “what’s the right technical call” and “how do you get humans to actually make it” — because in every job since FL0, that’s been the actual job.

Tone

Plainspoken and declarative. Short sentences. Subject-verb-object. No marketing language. No hedging.

Matter-of-fact about painful things. Heavy events land in parentheses or single sentences. No dwelling, no melodrama.

Comfortable swearing naturally. Not stylized — just how I talk (“fuck up”).

Confident self-assessment without bravado. Will state strengths flatly without softening or boasting.

Causal narrator, not emotional one. Explains why things happened more than how they felt.

Not writerly. No metaphors, no scene-setting, no flourishes. Reports.

Dryly understated in places.

Spine

I had a raw list of 26 topics I might write about: Platform Engineering, SRE, Software Engineering, Amateur Pottery, Books I Read, Music Production, Using AI, Learning to Cook, Learning to Surf, Creating Habits, Creating Routines, Relationship Advice, Stoicism, Meditation, Productivity, Tech Reviews, Drones, Photography, Being Creative, Personal Accounting, How to Learn, How to Execute, How to Choose Boardgames, How to Teach Boardgames, Living Alcohol Free, Making Coffee, Interior Decorating.

Claude’s observation: “it isn’t 26 topics. It’s one topic with 26 surfaces. Half the list is explicitly framed as learning something. The professional cluster (Platform/SRE/SWE/AI) is the same shape — currently figuring out how to ship well with AI, how to lead under pressure.”

The line I’d written about myself earlier in the process: “I do a lot of stuff. I like trying new things all the time. Momentum is the hardest thing to keep.” That’s not a complication to the spine. It is the spine.

Process. How I’m figuring out how to actually do things well — at work and outside it.

Foil

Productivity isn’t the goal. Being happy is. Productivity doesn’t always lead to happiness.

Promise

Notes from an Australian engineering leader. Things I’m building, teams I’m leading, habits I’m creating, and hobbies I enjoy. I’ll try to ship weekly, and when I don’t I’ll let you know.

Action items

With the posture in place, the actions were obvious:

Resurrect lswith.io. Blog and an email newsletter.
Daily 10-minute Obsidian habit. Export my daily shutdown from Sunsama and write down possible posts from the day.
Four articles by the end of the month. One each Friday.
A do-not-publish list, so I know what I’m not going to write about.
Stay in touch with the knuckleballers: the people I respect and share trade secrets with. My community.

I now have started going through those action items and making it become a reality. This is the first post. Hope you enjoyed it.