3 Reasons Why AI Isn’t a Good Planning Partner

Using AI to help you plan feels productive — until you realize you're spending more time managing the tool than making decisions that matter.

Since writing about the Centaur approach to AI last year, I’ve done even more deep diving into where AI is especially useful, where it’s over-hyped, and where it’s trash. In that piece, I argued for a centaur model — AI augmenting human capability, not replacing our thinking. I warned about the “siren song of outsourcing our thinking” to AI.

Most people get that AI can’t replace them as planners. But what’s less obvious is how badly it fails as a planning partner — even though that’s exactly how most people try to use it.

Important Note: In this article I’m using the term “planning” in the narrowest sense: making commitments, sequencing projects, resolving priorities, etc. In other words, this is the work of the middle, “Designer” productivity persona from our Momentum Quiz. Some of you may be thinking of ideation, visioning, and brainstorming as part of planning, too. They are part of the planning process in the broadest sense, though in this context I’m considering “Visionary” work like those as important preliminaries to the core work of planning. Those visionary tasks (and some of the action-oriented tasks of the “Creator”) are places where AI can be useful.

When I started testing AI as a planning assistant, I approached it with both optimism and a healthy paranoia that it’d make a good bit of my body of work obsolete. I was genuinely hopeful that AI would have solved evergreen planning challenges and had an eye on how we might integrate it into our app, Momentum.

But a year of experimentation has revealed that AI isn’t a good centaur partner for planning. It’s not augmenting our planning ability; it’s undermining it. The very things that make planning effective (judgment, context-holding, commitment-making) are precisely what AI can’t do. Instead of being a helpful assistant, it becomes a time-consuming distraction.

This might not be your struggle yet. But I’ve seen this movie before with leaders and creatives losing months chasing shortcuts or the technology du jour that actually steal momentum. Today’s version is AI-powered planning tools that promise to save time but deliver the opposite.

The Three Reasons

Here are a few reasons why you shouldn’t let AI do your planning:

1. It Doesn’t Think — It Only Repeats Patterns

Despite how many people think about it, AI isn’t a semi-omniscient entity. At its core, it’s a pattern machine and doesn’t actually think. It takes what it has seen before and remixes it into something that looks plausible.

That’s great when you’re stuck staring at a blank page, but it’s a terrible fit for planning. Planning is about resolving conflicting priorities, sequencing projects, and dealing with the residue of displacement.

When you try to use AI as a planning partner, you’re asking it to help with the thing it’s the least equipped to do.

Instead of clarifying your priorities, it tends to amplify the noise.

You end up with a list of tasks that might look right on the surface but don’t actually connect to your goals.

It can’t feel the tension between competing priorities or sense the emotional weight of choosing one path over another.

That’s why AI-assisted planning often misses the mark. You get generic suggestions, not tailored insights about your actual conflicts and commitments.

Now, I’ll acknowledge that for some people, AI can be helpful in getting started—it gives them a framework or breaks through the blank page paralysis. If that’s working for you, great.

But be careful. What starts as “just getting some ideas” can quickly turn into the time-wasting loops I’m about to describe. And even when AI helps you start, it can’t tell you what actually matters most to you or your team. That part — the heart of planning — is still on you.

2. It Doesn’t Keep Long-Term Context Well and Hallucinates

If you’ve played with AI before, you probably just thought “sure, it can’t tell me what matters to me and my time, but I can tell it and then it can help me.”

Not so fast. AI consistently forgets and hallucinates. It doesn’t naturally track the evolution of your goals, priorities, or changes in circumstance unless you spoon-feed it every update.

Even then, it can contradict itself or lose the thread. Planning, though, is the practice of holding context — how today’s work connects to this quarter’s focus, and how both connect to the long game.

What this means in practice is that you’ll spend a lot of energy trying to keep your AI planning partner coherent. You’ll find yourself correcting, re-explaining, and reorienting it, only to have it drift again.

And let’s go back to it being a pattern-recognition engine: the point of continuous planning a la momentum planning is to improve how you make commitments (plan) based upon what you actually do. If you consistently over-commit, AI will see that pattern and repeat it, left to its own devices. If you spin some magical thinking tale about how you can do more than five projects, it’ll continue to repeat that pattern. Until it forgets or hallucinates, then who knows what it’ll come up with.

It’s like trying to train a dog that doesn’t remember yesterday’s lesson. Instead of saving time, it pulls you deeper into the work of editing and evaluating. Use it long enough and you’ll get a low-grade paranoia that it’s missing something, which is better than NOT having that paranoia and being off-track for months or quarters even after you’ve spent time making the plan.

Probably better to spend no time planning and instead steer by intuition than to spend a bunch of time making a plan you can’t trust.

3. It Will Probably Take More Time and Be Harder

Many clients have shared similar experiences: what starts as a “quick AI planning session” turns into an hour-long prompt engineering exercise. By the time they’ve explained their context, corrected the misunderstandings, and fixed the output, they could’ve had their plan done and moved on to other important work.

Through the years, I’ve learned that most of us aren’t actually bad at planning. We’re bad at sitting down to plan and doing so consistently. We treat it like it’s some complex ritual that requires special tools or perfect conditions. AI feeds this misconception by making planning seem even more complicated than it is.

Good planning is simple. You look at what matters, you make some choices about where to spend your time, and you commit.

The 10/15 Split exists because that’s literally all the time it takes — 10 minutes to plan your day, 15 to review it. Not 10 minutes to craft the perfect prompt, then 15 to argue with AI about why it doesn’t understand that your client work matters more than inbox zero.

Every time you lean too heavily on AI as a planning partner, you’re dodging the one thing that would actually make planning easier: actually doing it yourself. It’s like having someone spot you on every single pushup. You never build the strength to do them on your own.

When you do the reps every day, you get better and faster at it. Because you’re doing it frequently, you retain a working memory of your goals, plans, and adjustments. But that only happens when YOU do the reps, not when you’re teaching a chatbot about your life.

Core Skills Outlast Technology

This whole situation reminds me of teaching orienteering in an age of Apple and Google Maps. Sure, the technology works great — until you actually need it. Dead battery, no signal, or you’re somewhere the maps haven’t been updated. That’s when the person who knows how to read a paper map and use a compass keeps moving while everyone else is stuck.

Planning is the same kind of core skill. Planning isn’t just organizing information and repeating patterns. It’s about making commitments. It’s about feeling the weight of trade-offs and displacement and choosing anyway. It’s about seeing how well your plan tracked reality and effort, then trying again.

AI can’t do any of that for you. More importantly, when you try to make it do that, you rob yourself of the very practice that makes you better at steering your own life.

In an age of technological flux, being a practiced planner — whether you use the Momentum Planning Method or any other approach that works for you — gives you something no app can provide. You can plan anywhere, with whatever tools you have, quickly and reliably.

The point of planning isn’t to spend more time planning. It’s to get to work on what matters most.

Right now, AI pulls you in the opposite direction, trapping you in “productivity theater” where an hour of prompt engineering feels productive but leaves you further from your real work than when you started.

So the next time you feel tempted to punt your planning to AI, try this instead: sit down with your tools, give yourself ten focused minutes, and notice the difference. Chances are, you’ll walk away with a plan that’s not only faster and better—but yours. And that’s what will actually move you forward.

If this still feels like a distant problem, that’s the point. I’d rather you not spend the next 18 months testing and tweaking only to discover what many of us already have—that AI adds fragility, time, and noise to a process that works best when it’s simple, human, and practiced.