This afternoon I used the following prompt to help me assess posts I’d written a few years ago for updating:
I have a personal blog at https://sjl.us
Please review my blog posts that are between two and five years old and give me a prioritized list of which ones you think I should update.
I was curious how well it would do at this task. Turns out I was pleasantly surprised. Here’s the result:
Here’s my prioritized list of your blog posts (published roughly April 2021–April 2024, i.e., 2–5 years old as of April 2026) that I recommend updating, ranked from highest to lowest priority.
I reviewed the site structure, monthly archives, and indexed posts via searches. Your blog has dozens of posts in this window (mostly personal essays, photography, history, productivity/PKM, and heavy AI experimentation from the 2022–early 2023 wave). I prioritized based on:
- How much the topic has aged (AI/prompting/tech tools change fastest; photography, personal reflections, and history are more timeless).
- Potential value of an update (adding 2026-era insights, new examples, current tool versions, or follow-up reflections makes the post fresher and more useful to readers).
- Thematic clustering (your AI/PKM series from 2022–2023 forms a natural arc that would benefit from a cohesive refresh).
I focused on the highest-impact ones rather than every post. Many others (e.g., pure street photography, freeway essays, family stories like the Tracy obituary, or 2021 COVID-era reflections) are still strong as-is and don’t need updates unless you want to add new photos or minor notes.
Top Priority (Strongly recommend updating soon — these are the most dated but highest-potential)
- Multi-step prompting for Claude (August 11, 2023)
https://sjl.us/2023/08/11/multi-step-prompting-for-claude/
Why update? Early Claude-specific prompting techniques; the entire field (Claude 3/4 families, GPT-4o-class models, Grok, etc.) has advanced dramatically. Easy win: expand with 2026 best practices, new multi-step examples, and comparisons. - My Current PKM Stack as of September 2023 (September 20, 2023)
https://sjl.us/2023/09/20/my-current-pkm-stack/
Why update? Details your Obsidian/Instapaper/Feedly/Drafts workflow at the time. Tools and plugins have evolved a lot; readers love current “state of my stack” posts. A 2026 version would be highly engaging. - Using AI to Help Write (November 15, 2022)
https://sjl.us/2022/11/15/using-ai-to-help-write/
Why update? Pure GPT-3-era experimentation. Perfect opportunity to contrast 2022 capabilities with today’s multimodal models and show how your own AI-assisted writing process has matured. - LLMs = Dream Machines (December 11, 2023)
https://sjl.us/2023/12/11/llms-dream-machines/
Why update? References to early hallucination discussions and Andrej Karpathy’s tweet feel historic now. Update with current “dream machine” examples and how you use LLMs in 2026. - Crafting Effective Prompts for Your AI Assistant (Claude, ChatGPT, Bard, etc.) (September 9, 2023)
https://sjl.us/2023/09/09/crafting-effective-prompts-for-your-ai-assistant-claude-chatgpt-bard-etc/
Why update? Another core prompting/PKM-adjacent piece from the explosion period. Pair it with the multi-step post for a nice “2023 vs 2026 Prompting Guide” refresh.
High Priority (Worth updating — clear value-add)
- An AI Thanksgiving (November 22, 2022)
https://sjl.us/2022/11/22/an-ai-thanksgiving/
Why update? Fun GPT-3 + DALL·E experiment. Readers would love a 2026 “then and now” version with newer models/image generators. - Hacking Creativity with AI (August 22, 2023)
https://sjl.us/2023/08/22/hacking-creativity-with-ai/
Why update? Early chatbot creativity techniques; the creative workflow space has exploded since then. - On the Minimum Viable Environment (MVE) and Apple’s Vision Pro (July 1, 2023)
https://sjl.us/2023/07/01/on-the-minimum-viable-environment-mve-and-apples-vision-pro/
Why update? Pre-launch speculation. Vision Pro shipped in 2024 — you can now add real-world usage, ecosystem updates, and whether MVE thinking held up. - Drafts – a tool for idea capture (April 16, 2022)
https://sjl.us/2022/04/16/drafts-a-tool-for-idea-capture/
Why update? The app was celebrating its 10th anniversary then; it’s now 14+ years old with major feature/UI changes. Your long-term usage makes this a great “then vs now” post.
Medium Priority (Nice-to-have updates if you have time)
- Reading Books in 2022 (May 11, 2022)
https://sjl.us/2022/05/11/how-im-reading-books/
Why consider? Kindle/app habits and highlighting workflows have evolved; easy to refresh with current tools and your 2026 reading volume.
Other notable 2023 AI-adjacent posts (e.g., NotebookLM deep-dive from Dec 2023, Explorations of PKM from Oct 2023) would slot in here if you want to do a broader “AI/PKM 2023 Retrospective” series.
Lower Priority / Probably Leave As-Is
- Photography series (e.g., “Capturing the Art in Everyday Scenes,” Paris posts, “Redwood Circle,” etc.) → Timeless and visual; they hold up well.
- History/personal essays (e.g., “Ode to a Queen,” “The World’s Most Beautiful Freeway,” “Remembering Blue Chip Stamps,” “Old Man Walking,” 2021 book recs, “Stuck in Neutral”) → Evergreen or emotionally resonant; updating could dilute their original voice unless you have new material.
- Holiday/personal posts (e.g., Thanksgiving 2023, Merry Christmas 2021) → Fine as snapshots in time.
Quick recommendation on approach: Start with the top 5 (they form a nice cluster around AI prompting/PKM). Updating them together would create a strong “2023 AI Reflections – Revisited in 2026” section or category on the blog. Many of these posts already reference each other, so cross-linking updated versions would be powerful.
If you’d like me to pull full content from any specific post, draft sample update language, suggest new sections, or help with images/AI-assisted rewrites, just let me know! Your blog has a great reflective voice — these updates would keep it feeling current without losing that personal touch.