When Certainty Comes Too Late

In What Grandma Knows That the Recipe Doesn’t, we looked at environments where feedback is plentiful enough for experts and novices alike to see whether their actions are moving them towards the desired outcome. In cooking, you follow a recipe, you intervene, adjust and repeat. This allows expertise to accumulate over time reasonably well. Same goes if you are training to get better at tennis or learning a new programming language.

But what about environments where feedback takes years, like parenting, or is noisy, like business strategy or organisational design? Where many things change at once and causality is hard to establish?

How can you know whether what you have decided to do is the right thing?

The answer is: you can’t.

Borrowed knowledge and the three Cs

Which is why in the face of uncertainty people fall back on a few things, namely:

Borrowed knowledge: Advice, research, history and other people’s experience. In parenting, for example, this includes generations of parents, psychologists and educators trying to understand what helps children thrive. It is useful because it lets us understand the decades of feedback loops that we could not otherwise experience ourselves.

The same reason why having a mentor to advise in your career is useful. Their experience and network provide useful access to a wider context than your current organisation.

But borrowed knowledge comes with a warning. Mary Schmich in her famous essay described advice as a form of nostalgia: we retrieve the past, paint over its flaws, and recycle it for more than its actual worth.

Borrowed knowledge can help inform our thinking, but we still must decide what matters and why we believe a particular approach will work. This is where the three Cs come in: Causal Theory, Consequence and Change Course.

On parenting

I want my kid to develop resilience. The ability to face setbacks, recover and keep working at something difficult. I believe developing resilience will help my kid overcome challenges and thrive.

She has taken to swimming recently, which gives her repeated opportunities to practise, fail, improve and deal with disappointment. So, maybe competitive swimming could be a good place to develop herself.

How does she cope with a disappointing race? Does she return to training with confidence and energy? Can she take feedback without falling apart? Could she learn to distinguish “I failed” from “I need to improve” and understand that winning does not mean there is nothing left to improve? Can she regulate her emotions well enough that she does not need an adult to fix her feelings?

But suppose after a year of competitive swimming and she becomes more anxious, increasingly terrified of failure, or tying her self-worth to winning. Then changing course would be needed, and this includes changing coaches, reducing competition, or even abandoning competitive swimming entirely and trying another activity.

The uncomfortable truth is that parents can do all that and still not know for sure if their kid would indeed thrive at 30.

So perhaps the answer to navigating uncertainty is not about accurate prediction, but rather a mechanism to stress test what you currently believe, why you believe it, what evidence you watch for to know, and what conditions would make you change direction?

Let’s look at another example.

On careers and future options

Increasingly, because of how AI is disrupting how work gets done, people are rightly concerned whether the job, industry and capabilities they have today would still be relevant in the future. There is a lot of anxiety but not a lot of answers. Even some of the brightest minds behind AI have sounded the alarm, while openly acknowledging what they know and what they don’t.

And when there is high uncertainty, a more manageable question could be:

Does what I do now increase or reduce the range of good choices available to me later?

Notice how this shifts the problem from predicting an unpredictable outcome to better positioning.

In terms of a career, suppose what you are optimising for is freedom: having meaningful choices about where you can work and what you can do next. Your causal theory might be that the future options would come from being in growing markets, where investments and policy decisions are moving in favour of your industry, and you are developing capabilities that remain useful beyond your current employer.

So, the consequences you look for are not simply whether you got promoted this year, instead you watch to determine if demand for your capabilities is expanding. You would look for evidence that investment continues to enter the sector, that your role is exposing you to increasingly valuable problems, and that you are acquiring skills valued outside your current organisation.

And if all those conditions begin to reverse or diminish, changing course would be the rational thing to do even if the job and role remain comfortable.

An important point I would make here is that changing course does not necessarily mean changing your goal or what you are optimising for. Sometimes it is precisely because we want to preserve the goal that we need to change the route. For example, someone leaving a job may look like a major change from the outside, when in fact, changing jobs may be an act of greater commitment to their goal.

The price of keeping your options open

People often make the mistake of equating having more options with not committing. “Keeping my options open” can itself become a trap, especially when some outcomes require closing options and committing deeply.

Consider elite athletes competing at the highest levels. They often begin training from very young, spend years in regimented practice, and sharpen their edge through repeated competition. Mastery is created partly by what they choose not to pursue.

Someone optimising for elite athletic performance may rationally narrow their life considerably. It is a common pathway seen in world-class musicians, dancers, chefs, specialist physicians and surgeons too, where mastery is built through years of deliberate practice and increasingly deep commitment.

Someone optimising for future freedom may make a different choice, but that does not mean avoiding mastery. It may mean choosing to go deep on capabilities that remain valuable across different organisations, technologies or industries. A software engineer might invest deeply in systems architecture and computational thinking rather than becoming defined by one programming framework. A data scientist might master statistics, experimentation and causal reasoning rather than one analytics platform. Similarly, a marketer might choose to develop a deeper understanding of customer behaviour, positioning and how demand is created instead of becoming an expert only in tools. Yes, I am looking at you, certification hoarders!

So, expanding your future options requires knowing what deserves that depth of commitment. It is not a free pass to choose an easier or less committed route. Some of the most valuable things in life only become possible when we stop protecting every option and commit enough to risk something. Love is like that too: you cannot love deeply without risking your heart.

Borrowed knowledge and the three Cs

On parenting

On careers and future options

The price of keeping your options open

Further reading