Chin-Ning Chu is one of my favorite authors. I first heard about her, when Dan Kennedy recommended Thick Face Black Heart as an essential read in cultivating the right mindset. The book fuses the wisdom of the East and West, and explores how ancient Asian battle strategies and cultural mindsets can be applied today to achieve mental toughness and winning business techniques.

Her work carried a kind of restraint that didn’t need to convince you of anything, and knowing that she eventually lost her battle with cancer adds a layer to her writing that is difficult to separate from what she was saying about effort, control, and how we move through life. There’s a sense that she had already stepped outside of the urgency most of us operate within, and was writing from a place where time wasn’t something to fight with, but something to understand more honestly.

In Do Less, Achieve More, that perspective comes through in ways that are easy to read past if you’re not paying attention, because it doesn’t present itself as a system to adopt, but more as a series of quiet corrections to how we think about action.

One of those corrections that keeps returning to me, especially now, is her guidance to always overestimate the time required to
complete something.

I can see very clearly that I tend to do the opposite, and not occasionally but consistently enough that it has become my default way of estimating. When I think about doing something, I am thinking about it in a version of reality where everything moves cleanly from start to finish, where there is no interruption, no delay, no competing demand on my attention, and no internal resistance that slows the pace once I begin. That version feels accurate in the moment because it is uninterrupted, but it isn’t the version that ever plays out once the work begins to exist in real conditions.

There’s no friction in the mind when you are planning.

No slow systems, no unexpected conversations, no moments where energy dips or focus shifts, no external demands that pull you out of what you intended to do. All of that only appears once the work is in motion, and by then the estimate has already been set, which is why it so often begins to stretch in ways that feel inconvenient but are actually predictable.

So when she speaks about overestimating time, she’s not talking about padding the schedule for comfort as much as correcting for a bias that keeps showing up, whether I account for it or not.

There is a well-documented tendency to underestimate how long things take, not because we lack intelligence or experience, but because we naturally default to imagining the best-case version of events, even when our own history suggests otherwise. The mind constructs a clean path, and then reality fills it with texture.

When I look at what happens when time is underestimated, the impact is not just on the schedule itself but on how the work is experienced. There is a pressure that builds when something starts to exceed the time you thought it would take, and that pressure shifts the focus from doing the work properly to trying to reconcile the gap between expectation and reality.

Overestimating time, on the other hand, changes the conditions under which the work is done.

It reduces the sense of urgency that comes from chasing a timeline that was never realistic to begin with, and it creates a buffer for the interruptions and delays that are part of how work actually unfolds. There is more room to adjust, to refine, to respond to what is happening instead of forcing everything to fit into a predetermined window that doesn’t account for variation.

It also builds a different kind of reliability, because when timelines are grounded in how things tend to unfold rather than how we hope they will, delivery becomes more consistent. There is less need to renegotiate expectations or compensate for delays, because those delays have already been considered as part of the estimate, even if they don’t always materialise in the same way.

What I’m being reminded of, especially with several projects currently in motion, is that my estimates
need to come from lived experience, not imagined efficiency.

That means looking at how long things have actually taken in the past, breaking work into smaller components instead of treating it as a single block, and applying a multiplier to my initial estimate to account for the parts I cannot see at the outset. It also means recognising that finishing early is not a problem to solve, but simply an outcome that can be absorbed by having other smaller tasks ready, rather than allowing the time to dissipate.

There is a balance because giving something more time does not automatically mean it will be used well. Work has a tendency to expand to fill the time available, and there is also the reality that things often take longer than expected even when you try to account for that. So this isn’t about removing discipline from the process, but about aligning the estimate with reality while still maintaining focus in how the time is used.

What stands out most for me right now is that this isn’t a new insight, but it is one I have not been applying with consistency.

I continue to estimate based on how I think things should unfold, rather than how they actually do, and then adjust in response to the difference instead of addressing the source of it at the planning stage.

I can see the pattern clearly enough to interrupt it, which is probably why this particular piece of guidance is staying with me now, not as something abstract, but as something to apply directly to the work already in front of me.

Strategic Reflection Prompt

Where are your current timelines being shaped by how you imagine work will unfold, rather than how it consistently does, and what changes when your estimates begin with your lived experience instead of your ideal conditions?

About Giselle

I’m Giselle Hudson, a Business Diagnostic Specialist. I work with leaders when something feels off — where results, decisions, or team response don’t match what was expected. I examine what’s shaping outcomes beneath the surface, so the next move is grounded, not reactive.

If this feels familiar, don’t rush your next decision. We can look at your situation properly before you take action.