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The 2026 AI
Halftime Report

AI changed more this year than most people noticed. Here are the three shifts that matter, a quick audit to see where you stand, and three predictions to get ahead of.

I wrote this at the halfway point of 2026 and refreshed it on November 1. If you’re still using AI the way you did in January, you’re behind, and this is the fastest way to catch up.

Three shifts, a two-minute audit, then what I’d get ready for next.

Shift 1: Chatbots Became Agents

The smartest AI users stopped only asking AI questions. They build agents, workflows and loops that run while they sleep. The unit of work went from a single answer to a whole job done on its own.

The move: build one small agent that does a real task start to finish. My how I build AI agents guide walks you through it.

Shift 2: Prompting Became Setup

A year ago the skill was writing the perfect prompt. Now it’s giving AI the right context and setup so you can hand off the whole job. The win moved from the words you type to the environment you build around the model.

The move: stop starting from a blank box. Save reusable context, and trim what you already have with my Context Cleanup Checklist.

Shift 3: It’s Not ChatGPT vs Claude

The best AI users don’t have a favorite model anymore. They switch between Claude and ChatGPT depending on the task.

The move: learn which model wins at what. My best model for the task cheat sheet makes it a lookup.

Score Yourself

Three honest checks. Every one you can’t tick is your next move.

For a real score instead of a gut check, paste this into Claude or ChatGPT, fill in the brackets, and it grades you on all three shifts and hands you your next three moves.

The Halftime Self-Audit
You are my AI coach. Your job is to give me an honest score on how I use AI right now and pick my next three moves. Be direct. Do not flatter me. HERE IS HOW I USE AI TODAY (I filled this in): - My job or business: [one line] - The AI tools I use and how often: [e.g. ChatGPT daily, Claude a few times a week] - The last 5 things I asked AI to do: [list them, as specific as you can] - Anything I have set up to reuse (Projects, custom instructions, skills, saved prompts, automations): [list, or "none"] - Anything that runs without me starting it: [list, or "none"] STEP 1. Score me from 0 to 3 on each shift, with one sentence of evidence from what I wrote: 1. Chatbot to agent: do I hand AI whole jobs that run start to finish, or only ask it questions? 2. Prompting to setup: do I give AI saved context and reusable setups, or start from a blank box every time? 3. One model to the right model: do I pick the tool by the job, or default to the same one? STEP 2. Name my weakest shift and explain in two sentences why it is holding me back, using my own examples. STEP 3. Give me three next moves, ranked. Each one must be: - tied to a task I actually listed above - doable in under 30 minutes - written as exact steps, including which tool and what to click or paste STEP 4. Write me one test I can check in 7 days to know it worked. Make it observable, like "I did X without opening a blank chat." FORMAT: a short score table (shift, score, evidence), then the weakest shift, then the three moves as a numbered list, then the 7-day test. Keep it under 300 words. RULES: - Only recommend tools I already use unless a free option clearly beats them. If you suggest something new, say if it costs money. - If you are not sure a feature exists in my tool, say so instead of guessing a menu path. - If my answers are too vague to score, ask me up to 3 short questions first.
My 3 Predictions Going Into 2027
  1. Talking takes over typing. We’ll talk to AI and show it our screen more than we type. Get ready by dictating now. Wispr Flow is an easy place to start, with a free plan on Mac, Windows, iPhone and Android.
  2. Agents go mainstream. I think more than half of professionals will soon have at least one agent working for them every day. Get ready by building your first one this month.
  3. Every company over 20 people hires someone to manage its AI systems. Get ready by quietly becoming that person on your team.

The Real Win

The people pulling ahead aren’t smarter. They updated their approach the moment the tools changed. Reading this, you just did too.

If you’re catching up from zero, start with Getting Started With AI, then run my 7-Day AI Starter.