We make plans, and they help—they’re important, maybe even necessary. But as the saying goes, “Life is what happens when you’re busy making plans.” Things don’t often go exactly as expected. Sometimes we can’t follow a plan straight through the day because unexpected things come up, or things take longer than estimated—no matter how many times we’ve learned that lesson before.

For example, say you commit to a deadline at work, expecting everything to go smoothly. Honestly, you thought a certain task would only take two days—but then, it doesn’t. A dependency you were counting on gets delayed, or the task is simply more complex than you initially thought. Suddenly, you feel tense and pressured because it threatens to make you late. Even though you won’t be dead from missing the deadline, the fear of being late, of not meeting expectations, of things slipping beyond your control—creates stress.

On a larger time scale, sometimes we can’t even go on that trip we planned because of unforeseen circumstances. We were keen and set strong intentions to serve the 60-day Vipassana meditation course—what could be more important? But we couldn’t, and we resolve to take the opportunity next time it comes around.

So, since planning and intentions are unavoidable, productive, and in our best interests—yet things don’t go to plan and we still get attached to Plan A—let’s talk about the drawbacks of getting too attached to the plans we make.

I recently read Time Surfing by Paul Loomans, a simple, profound book. It’s interesting that a time management book was written by a Zen monk—someone I think I could trust to value balance, equanimity, and harmony. Sounds good to me - a good contrast to the usual mindset of productivity—abundant on YouTube—where we hustle and our main aim is to maximise output and “get ahead”.

At the core of his Time Surfing principles is the idea that we need to be balanced with what we’re doing and learn to use our intuition when deciding what to do. It’s simple—but like all profound teachings, simple in theory, easy to forget, and harder to practice. As someone who aspires to be more equanimous, I always appreciate reminders like this. It never gets old, because it’s so easy to fall into thought patterns that lack this kind of wisdom.

The Good Side of Planning

First, let’s talk about the benefits of planning. When I say planning, I’m referring to intentionally clarifying what we think we ought to do, whether in general or over the long term. Then, we break it down into smaller timeframes—a year, a quarter, a month—to figure out what to focus on next.

I once heard an executive at work say: “If our daily actions don’t align with our long-term goals, let us know, because either our daily actions are off, or our goals are wrong.” Same idea here—but let’s be real, in most workplaces, we’re not exactly personally aligned with the company’s long-term vision. Still, in personal life, that congruency matters.

Planning is a meta-skill, one of those broader skills that improve multiple areas of life—like exercise, meditation, or deliberate learning. It’s a tool, a skill, and a habit worth developing.

The benefits? It helps us clarify our values, align our actions, and feel grounded—confident that our time is being well spent. But this confidence only holds if:

1. We believe in the cause.
2. We take action. (As opposed to making plans, feeling good about it, and then doing nothing.)

Otherwise, things are more problematic—but that’s a different discussion.

This Risk Of Getting Attached

We’ve already mentioned the reality that things don’t go as planned. But why does that matter? What’s the risk? Why isn’t it all rainbows and butterflies, all good in the hood, if we simply use planning as a tool?

The problem isn’t just that plans are imperfect. The problem is that we tend to get attached to them, which is revealed every time things don’t go as expected.

This attachment can lead to unnecessary frustration, rigidity, and stress—things that can be prevented if we recognize them early.

Why’s Getting Attached Bad?

Let’s break this down further. What does attachment to plans actually cause?

1. We React Negatively to Change Instead of Staying Calm

When things don’t go to plan, we feel anxious, irritated, or defeated. We resist reality and sometimes even refuse to adapt.

What kinds of deviations are we talking about?

• Tasks taking longer than expected
• Unexpected delays
• Dips in energy levels
• Emergencies
• More important priorities arising

Sometimes, changing course is actually in our best interest. But the more attached we are, the harder it is to let go and adapt.

2. We Resist Adapting, Even When It’s the Best Move

Since we’re annoyed that things didn’t go to plan, we:

• Change course reluctantly—with resistance, frustration, or stubbornness.
• Cling to the original plan, even when it’s clear we should pivot.

Instead, we should be able to calmly and rationally assess whether the plan needs changing—and adjust if necessary.

3. We Write Off All Distractions as Bad (Even When They’re Not)

Not every distraction is bad. But when we’re too attached to our plans, we tend to dismiss all interruptions as obstacles.

• Bad distractions: Mindless scrolling, giving in to cravings.
• Good distractions: Helping someone, seizing an unexpected opportunity.

Some so-called distractions actually align with our goals. The key is discerning between valuable detours and actual distractions.

What Should We Do?

The answer isn’t to throw planning out the window. Planning is too valuable a tool to discard. Instead, we should use it skillfully while staying aware of its limits.

1. Overestimate Time & Expect Deviations

Things always take longer than expected. No matter how much experience we have, it’s easy to underestimate how long tasks will take, especially when unexpected obstacles arise. A good approach is to under-promise and over-deliver—giving yourself more time than you think you’ll need. This helps minimize the times when you find yourself rushing due to poor estimates, though it’s still bound to happen sometimes. That’s why the next strategies are important.

2. Be Aware of Tension & Anxiety

When plans shift, notice if you feel frustrated or rigid about the change. Ask yourself: "Is this really catastrophic? Am I being unreasonable?" Often, the discomfort isn’t from the plan changing—it’s from our own attachment to it. Simply remembering that plans are just intentions, not guarantees can help ease the tension. When we recognize that our frustration is rooted in unrealistic expectations, the stress often dissolves on its own.

3. Remember That Plans Are Just Intentions, Not Guarantees

It’s easy to treat plans as if they’re set in stone, but in reality, they’re just our best guesses at a given moment. Holding ourselves to 100% adherence is an unrealistic expectation. Plans are not contracts—they’re flexible tools. If we remember this, we can adjust with less resistance and more ease when things inevitably shift.

A Simple Insight

I find that simply being aware of the tension that arises when plans change and recognizing the faulty assumption that plans should always go perfectly really helps. When I notice frustration creeping in, I remind myself that the discomfort isn’t from the plan changing—it’s from my own attachment to it. And that attachment? It was unreasonable to begin with, because plans aren’t perfect!

4. Be Open to “Good” Distractions

Not every distraction is bad. When we’re too attached to plans, we tend to dismiss everything unexpected as an obstacle, but sometimes these detours are valuable. There’s a difference between mindless distractions—like scrolling social media out of habit—and good distractions, like a friend reaching out with an unexpected opportunity or an insight that shifts our priorities. The key is to discern whether an interruption is actually misalignment or just a different route to the same goal.

So remember planning is useful, but plans are just intentions and we can’t predict the future with 100% accuracy, so flexibility is what makes it work in real life 🙂

I hope that was useful. By the way I also made a video summarising these ideas. I’d love to hear your thoughts. Thank you for reading!

Originally published on Substack (2025).