The thing about plans
Everyone loves a plan.
There’s something deeply comforting about writing one down—about taking all the uncertainty in your head and forcing it into a clean, linear path from where you are to where you want to be.
For a moment, the future feels structured. Manageable. Almost predictable.
And then reality shows up.
The market shifts in ways you didn’t expect. People you were counting on leave. Timelines slip, dependencies stack up, and assumptions you didn’t even realize you were making quietly fall apart.
Before you know it, the neat plan you spent hours/weeks refining starts to look less like a roadmap and more like a rough draft that reality has already edited.
As Mike Tyson famously put it: “Everyone has a plan until they get punched in the face.”
It’s funny because it’s true. But it’s also deeper than that.
Nothing ever goes according to plan, not because we’re bad at planning, but because plans are, by definition, built on incomplete information. They are static snapshots of a world that refuses to stay still.
The moment you start executing, the world starts responding, and the gap between what you expected and what actually happens begins to widen.
And at the extreme, you get the opposite view - captured well by the Joker in The Dark Knight, who mocks the very idea of plans as an illusion of control. “Do I really look like a guy with a plan? You know what I am? I’m a dog chasing cars… I wouldn’t know what to do with one if I caught it.”
The truth, as usual, sits somewhere in between.
So if that’s the case, it raises an uncomfortable question: why bother planning at all?
Because without a plan, you drift
For all their flaws, plans serve a very important purpose - they give you direction.
Without a plan, it’s surprisingly easy to confuse motion with progress. You stay busy, you respond to what’s in front of you, you check things off a list, and it all feels productive in the moment.
But over time, you start to realize that you’re not really choosing your path - you’re inheriting it from circumstance, from other people’s priorities, from whatever happens to be loudest or most urgent.
And that’s a dangerous place to be if you care about doing anything meaningful.
Ambition, in its simplest form, needs direction. It needs a sense of “this is what I’m trying to do,” even if the “how” is still fuzzy. A plan is just that ambition made explicit. It forces you to make choices, to prioritise, to say no to things that don’t fit.
That act alone is valuable, even if the plan itself doesn’t survive contact with reality.
The mistake: treating the plan as sacred
Where most people go wrong is not in planning—it’s in how they relate to the plan afterward.
We tend to over-invest in getting it “right.” We polish it, defend it, and once we’ve committed to it, we feel an almost irrational need to stick to it. Changing course starts to feel like failure, like we’re admitting that we got it wrong.
But the goal was never to follow the plan perfectly.
The goal was to move in the right direction.
And those two things are not the same.
Execution is only half the game
There’s a popular idea, especially in business circles, that everything comes down to execution. That if you just execute well enough, things will work out.
Execution absolutely matters but it’s only half the game.
The other half is adaptation.
Execution is about doing what you said you would do. It’s about consistency, discipline, and follow-through. Adaptation, on the other hand, is about recognising when what you said you would do no longer makes sense and having the judgment to change it.
The reason adaptation is harder is because it’s less structured. You can’t just build a dashboard for it. It requires paying attention, being honest with yourself, and sometimes making uncomfortable calls.
But in a world that keeps changing, adaptation compounds faster than execution. A decent plan that you update continuously will almost always outperform a great plan that you follow rigidly.
Short-term flexibility, long-term consistency
So how do you balance all of this without swinging between rigidity and chaos?
A useful way to think about it is this: be rigid about your direction, but flexible about your path.
Over the long term, you want consistency. You don’t want to wake up every few months chasing something completely different—that’s not adaptability, that’s noise.
But in the short term, you need to stay flexible. You need to be willing to change tactics, adjust timelines, rethink intermediate goals, and even abandon approaches that aren’t working.
In practice, this creates a kind of loop:
You set a direction, you come up with a plan, you act on it, you observe what happens, and then you update the plan based on what you’ve learned.
And then you do it again.
Over time, the path you actually take will look very different from the one you initially imagined. But if your direction was sound, you’ll still end up somewhere that makes sense.
Plans are tools, not contracts
One small but powerful shift is to stop treating plans like contracts and start treating them like tools.
A contract is something you’re expected to honor, even when conditions change. A tool is something you use to make better decisions.
Plans are tools.
They help you think more clearly. They force you to articulate your assumptions. They give you a starting point so you’re not operating from scratch.
But once you start moving, their job is to be updated—or, if necessary, discarded.
The best operators aren’t the ones who stick to their plans no matter what. They’re the ones who know when the plan has stopped being useful.
The cost of not planning
Of course, once you internalise that plans are fragile, it’s tempting to go to the other extreme to stop planning altogether.
To just stay flexible, figure things out on the fly, and avoid the discomfort of being “wrong.”
But that comes with its own cost.
Without a plan, you lose intentionality. Your decisions become reactive rather than deliberate. You optimize for what’s urgent instead of what actually matters, and over time, you risk ending up somewhere you didn’t consciously choose.
Planning forces you to pause and ask a simple but important question: what am I actually trying to do?
Even if the answer changes later, the act of asking the question is what keeps you aligned.
Ambition needs all three
At its core, this entire tension comes down to three things: direction, plans, and curiosity.
Direction gives your ambition shape. It answers the question of what you’re moving toward.
Plans give your ambition structure. They translate intent into action.
Curiosity keeps your ambition alive. It’s what allows you to notice when reality doesn’t match your expectations—and to adjust accordingly.
Take any one of these away, and things start to break.
Without direction, you drift. Without plans, you stall. Without curiosity, you become rigid—and eventually, reality forces you to change anyway.
So why bother?
So, if plans are almost guaranteed to fail, why bother making them?
Because the value isn’t in the plan being right.
It’s in the process of creating it and the discipline of updating it.
Planning sharpens your thinking. It forces you to choose a direction. It gives you a baseline from which to adapt.
Not because the plan will work, but because it will evolve.
A better question to ask
Instead of asking, “Will this plan work?” it’s often more useful to ask a different set of questions:
What assumptions am I making here? What would need to be true for this to succeed? What early signals would tell me that I’m wrong? And how quickly can I update if things change?
This shifts planning from prediction to preparation.
You’re no longer trying to get the future exactly right—you’re trying to be ready for it.
Closing thought
Plans will break. They always do.
But that’s not a flaw, it’s a feature.
If your plan never breaks, it’s probably not ambitious enough to begin with.
So make plans. Set direction. Move forward with intent.
Just don’t get too attached to the exact path you’ve drawn.
Because in the end, the people who do well aren’t the ones who follow their plans perfectly.
They’re the ones who stay curious enough to change them and disciplined enough to keep going.