The paradox of overplanning – how to embrace uncertainty to boost productivity

Before I start, I have to disclaim – I’m not saying that you don’t plan. Planning is important. But the dose is what makes the poison – and hence, that overplanning can be detrimental.

The truth is, I like to plan quite obsessively. I time-block (almost) every hour of my day, colour-code my calendar, and even my recharge and relaxation time is scheduled in. Why? To feel in control, especially when the world gets more unpredictable each day.

But the thing is – life never goes according to plan. The more I plan every detail, the more I encounter the unpredictable. And because everything is so tightly packed, one derailed plan impacts the entire day. I try incredibly hard to make the perfect schedule, but that schedule (and me) ends up becoming very fragile.

And I’ve realised the paradox that, well, planning less can sometimes be better.

The allure of perfect planning

A year ago, I would never have acknowledged that there’s no such thing as perfect planning (I still have trouble acknowledging that!). And it’s evolutionary in nature. As humans, we’re wired to crave control. Predictability helps us to survive. Read any Economics textbook and it’ll espouse perfect knowledge, for perfect planning, for perfect deployment of resources.

“We think that the more precise the plan, the more likely we are to succeed in achieving it. Conversely, when our ambitions are rough and half formed, we presume that we lack permission to act.”

This excerpt from Choose Possibility by Sukhinder Singh Cassidy illustrates the psychology behind the need for control.

But that’s the thing.

It’s not control. It’s only the illusion of control, as psychologist Ellen Langer discovered. We overestimate our influences over outcomes. And the more life feels uncertain, the more we’re going to double down on the planning and scheduling and control. I know I do.

The truth is that overplanning isn’t about my productivity. It’s about my anxiety management. When I overplan, I’m planning for my anxiety about what might go wrong, not for doing more and being more.

There’s no such thing as the perfect plan.

Overplanning is a paradox – making us do less, rather than more.

The unproductivity of overplanning

As an overplanner, I’ve got a lot more plans than I actually use. It feels safe. The paradox is that the safety makes me do less than if I had fewer plans. I have way more planning than I need (which even I acknowledge). And here’s the cost:

• Cognitive overload: Your brain can only handle a finite number of moving parts at once. It’s like your RAM. Overplanning maxes out your mental RAM.
• Rigidity: You find it difficult to adapt to real-time information and circumstances – and application is the whole point of planning.
• No recovery: Packing your schedule so tightly that there’s no room for error means that there’s no room for recovery, especially when a task takes more time or energy than required.
• Reduced creativity: You know how creativity comes from the toilet (as in, you get your best ideas when you’re showering or doing unrelated things)? If everything in your schedule is always super relevant and related to what you do, then natural creativity gets stifled.

Psychological flexibility

When it comes to wellbeing, there are the six pillars of PERMAH – Positive emotions, engagement, positive relationships, meaning, accomplishments, and health. Engagement is hard to have when you have a rigid schedule that brooks no changes – how is flow supposed to come when you’re doing emergency rescheduling all the time?

The other pillars can still be achieved, if we lived in a static, stable world.

But we don’t. We live in a volatile, uncertain, complex, and ambiguous world – where there are multiple fluctuating and conflicting forces.

An example is this. I’ve planned (maybe overplanned) to study for a Master overseas this 2025. But no amount of planning could have predicted a change in student visa policy in my intended country of study. Even as I type this, it’s a developing situation that no amount of planning can cater to. I need to be adaptable, even when it comes to studies.

I need to have psychological flexibility.

Psychological flexibility has been suggested as another fundamental aspect of wellbeing – the seventh PERMAH pillar, in a way. Todd Kashdan and Joanathan Rottenburg defined psychological flexibility as being able to recognize and adapt to various situational demands; shift mindsets or behavioral repertoires when these strategies compromise personal or social functioning; maintain balance among important life domains; and be aware, open, and committed to behaviors that are congruent with deeply held values.

When you look at that description, it’s not all about yielding and changing to everything. It’s about being able to adapt and shift and be open, while also committing to your values. It’s a balance.

The seven principles of positive planning

I must disclaim yet again that planning is important. Colin Ashruf shares that even for innovation and creativity, planning and control are critical to success – to avoid the risk of getting lost. EJ Masicampo and Roy Baumeister found out that plan making can eliminate the negative effects of unfilled goals.

So this is not to say that you ditch planning. Planning > overplanning > not planning.

It’s to strike a balance with positive planning that prioritises clarity over certainty. Know exactly what you want to achieve, but be open to how you will achieve it.

I call it the hard what, soft how approach.

And here’s my approach.

1. Implementation intention

Plan your intentions, rather than the execution. Start your day by writing down your top three values (like creativity, integrity, storytelling) and align one task for each value. This helps add more meaning to your tasks, while also giving you a fulfilment metric for choosing your tasks.

2. Adaptive planning

You want to complete that task – but does it really have to be completed between 9.00am to 10.00am? What if you did it from 9.15am to 10.15 am? It’s about the hard what, soft how approach. It’s also called “planning for adaptability”. For that, you’ll also need

3. Time cushions

Time cushions mean padding your day with buffer time for the unexpected. Can you predict when you might go to the loo or feel thirsty? Leaving buffer time means you get to recover between tasks, which makes you more productive as you go into each one. It also means you can take unplanned calls, or just get a snack to recharge. And when something good comes up that you can say yes to, it means

4. The space to say “no” is the space to say “yes”

Because you’ve rejected (said “no”) to an overplanned schedule, it means that you can say “yes” to desirable, spontaneous plans that come up. It means that your “yes” is that much more authentic, and your “no” is that much more mindful.

Having more buffer time means that you can consider your decisions more carefully, and say “no” when you need to as well. You can say “no” mindfully – which equates to saying “yes” more mindfully to. This also means

5. Permission to cancel

Remember the three tasks that align to your values? There will be plenty of other tasks on your to-do list besides those. Those three tasks will feel like must-dos, so counter that with three can-skips.

That is to say, designate three tasks that you can cancel for the day. It means you skip it completely, delegate it to someone else, or defer to the next day. It’s a balance. If you cancel those tasks, you’ve already planned for it. If you manage to get to them, it’s a bonus. Win-win!

6. If this then that

I like my workflows, so I also plan simple “if this then that”. It can be rewards – if I complete this task, I can have that reward. It can be task sequences – if I finish this task by X time, then I will work on the second task; but if I don’t finish this task by X time, I will defer the second task to tomorrow. It’s simple adaptive planning that frontloads the thinking and rationale, so you can focus on the execution.

7. Be Elsa, and let it go

Sometimes, it’s just not a good day.

And the most important thing about productivity is this – follow the ebb and flow of your day, your energy, your attention. Unless you’re an utterly lazy wastrel (in which case, you wouldn’t be reading this) – there will be times when you feel like doing more. That’s when you do more, and the output will be magnified.

Other times, you just have to let it go and acknowledge that you’ll be more productive tomorrow.

Productivity over perfection

Overplanning is a symptom of perfectionism. But what you want isn’t perfectionism – it’s productivity. It’s about doing and growing and being, not a static state of unchanging perfection.

It’s an unplannable world. Clarity of purpose beats control of outcome. Don’t fall prey to the paradox of overplanning.

Using positive planning means being adaptable, intentional, and grounded – while still being task-focused and output-driven. It’s about doing the tasks with the most impact – impact on yourself, on others, and on society.

So choose positive planning, not overplanning.

After all, the best-laid plans of mice and men often go awry.

References

• Langer, E. J. (1975). The illusion of control. Journal of Personality and Social Psychology.
• Cassidy, S. S. (2021). Choose possibility: Take risks and thrive (even when you fail).
• Kashdan, T. B., & Rottenberg, J. (2010). Psychological flexibility as a fundamental aspect of health. Clinical Psychology Review.
• Ashruf, C. (2022). Planning the “unplannable” – The innovation management paradox. Journal of Innovation Management, 10(1).
• Bastian, H., Glasziou, P., & Chalmers, I. (2010). Seventy-five trials and eleven systematic reviews a day: How will we ever keep up? PLoS Medicine, 7(9), e1000326.