Your 2025 review + 2026 plan — with AI as a thinking partner

Hi everyone,

As the year ends, taking time to analyze what happened, and what you want to achieve next, is essential.

The most valuable way to use AI here isn’t to outsource reflection — “set my goals, tell me what to do next”.

Instead, work with AI to ask yourself better questions.

Over the holidays, I did my 2025 retrospective, and I only used AI to generate thought-provoking, brutally honest questions I wouldn’t have thought of by myself.

That process led to real clarity, and I’ll show you exactly how to do it in this week’s guide.

Taking a break from day-to-day work was just as important. As well as enjoying much-needed rest, I had space for new ideas to surface naturally without forcing productivity.

After that pause, everything clicked.

I’m heading into 2026 clear, energized, and focused — and I’d love for you to do the same.

Wishing you a very happy new year, from all of us at AI Operator! 🎉 🥳 🥂

This AI-enhanced New Year planning session will force you to question yourself and do some hard thinking before you map out 2026.

Time: 45 minutes - 1 hour

Tools:

AI can help you come up with meaningful questions that go beyond the surface level.

Paste this prompt into ChatGPT:

Act as a reflective interviewer who knows my business context. Ask me 10–12 specific, uncomfortable questions about my 2025. Avoid generic questions. Draw on everything you know about me based on the conversations we’ve had over the past year. Focus on:

Then, copy and paste the questions into a notes app.

Put your phone down, music on, and answer freely - no editing, no AI.

The goal? Get your unfiltered thoughts down on the page.

Answer this:

If I replayed 2025 with the same way of working — same priorities, same assumptions, same habits, same level of focus — would the outcome realistically improve?

In other words, consider how you showed up: what you chose to work on, how you made decisions, what you ignored, and where you spent energy.

Would you do it all the same next year?

If the honest answer is no, that’s the signal that 2026 needs different inputs, not just bigger ambitions.

Now paste your answers back into AI and ask it to:

Summarize the patterns in my answers. Highlight repeated friction, false assumptions, high-leverage actions, and where I’m confusing effort with progress.

You’re bringing in AI after the deep thinking is done.

You’ll get a high-level summary that cuts to the core of what you need to improve in 2026, and might even spot patterns or connections you missed.

At this point, you’ve done the hard part:

Now you can use those insights to plan 2026, without turning it into vague goal‑setting.

Start by asking AI:

Based on everything I’ve shared, help me define the constraints (not goals) for 2026. What should I do less of, stop entirely, or deliberately limit? What should be systemized or supported with AI?

Defining constraints can stop you from repeating the same mistakes as last year.

Examples of useful constraints:

Next, ask AI to translate those constraints into a simple structure:

Using these constraints, help me outline a high-level plan for 2026. Break it into quarters. For each quarter, provide:

This helps you set a direction without a rigid roadmap.

Next, you want to lock down what your focus is for each quarter.

A simple way to frame it might be:

You can ask AI to pressure‑test this:

Based on my past patterns, where am I most likely to overcommit or lose focus during the year? What safeguards should I put in place?

Before you finalize everything, step away from AI and ask yourself:

Your goal for 2026 shouldn’t be to do more, but to operate differently, with AI supporting your systems, not running your decisions.

Meta announced that it will buy Manus, the Chinese-founded startup that claimed to have released the world's first general AI agent, capable of making decisions and executing tasks autonomously.

This is a major investment in advanced AI agents, signalling a shift from chatbots toward systems that can plan, execute, and improve tasks autonomously, embedding agents into real workflows.

Why it matters: Agents are becoming more and more capable, but we need humans to keep them on track.

Microsoft CEO Satya Nadella said 2026 will mark AI’s transition from discovery to diffusion, where value comes from broad, practical use rather than constant breakthroughs.

Why it matters: Founders shouldn’t constantly chase novelty in 2026. Instead, they must figure out how to see through the hype and integrate AI successfully.

The so‑called “godfather of AI” warned that many jobs could disappear by 2026 — particularly roles that fail to adapt as AI becomes more deeply embedded in everyday work. This isn’t a signal to panic, though. It’s a reminder that AI is becoming part of the baseline, and those who learn how to work with it — rather than ignore it — will be the ones who stay ahead.

At AI Operator, we’re making a shift away from “AI-First” thinking, towards a more collaborative human + AI approach. Instead of outsourcing our thinking, we can learn to strengthen our skills with the right tools.

This final episode of 2025 is a reminder that AI can give you quick answers, but only humans with experience, judgment, and first-principles thinking can make good decisions.

Across conversations on leadership, resilience, and first-principles thinking, one idea stands out: AI is great at surfacing information, but humans must decide what matters.

If you’re about to start the 2025 retrospective and 2026 planning session in this guide, I’d recommend watching this first. It’s the perfect mindset reset.

In my most recent YouTube video, I talk about the latest NotebookLM features you need to know about, with 3 use cases you can try today: sales call prep, client onboarding, and content repurposing.

Watch it here:

To celebrate the end of the year, here are my most-loved tools of 2025:

Wishing you all a happy, healthy, and successful new year!

Thanks for all your support in 2025. I can’t wait to see what we achieve in 2026!