Category Archives: Careers

One of the most powerful ways for people to influence others to do something about certain causes is just to measure it. The most successful example being the creation of GDP as a concept to measure the economy. Suddenly, it displaced the more traditional metrics of population or military might (which involved more quantities than just number of troops involved).

There are always issues with measurements created. They do not perfectly measure the underlying thing we’re trying to quantify for two reasons:

• The measurement is inaccurate due to poor instruments used (proxies, poor surveyors etc)
• The measurement does not reflect the actual underlying concept we are trying to quantify.

The first point can be improved over time. The measurement accuracy would not be perfect but over time, as long as the measurement required is well-defined, we would be able to capture the quantity or at least get really close to it.

The second point is trickier and it is going to always be imperfect. And herein lies the danger of trying to make things measureable. The Goodhart law features an important observation we ought to be constantly reminded of as we’re bombarded with figures like GDP growth, inflation etc. It doesn’t mean they are false! But the key is to be able to distinguish the measure from the underlying concept of what the measure is supposed to imply.

In Singlish, there’s a question that typically stresses people out and has answers varying significantly based on the interpretation of the questioner’s purpose. But at the heart of the question “why like that?”, the questioner is questioning reality. And effectively trying to pit the answerer against the reality at hand.

In fact, implicit in the question is that the answerer should not be accepting reality as it is but to do something about it. That assumption is something worth some attention and awareness. For one on the receiving end of the question, bringing to attention is assumption takes a bit of courage but immediately resolves the internal tension and cast it back on the questioner.

So the answer becomes “why not?”, or “what did you expect?” Maybe just done a bit more politely.

When I was in primary school, I have this problem of doing mental sums. Calculations done in my head that I didn’t write on paper in my answer scripts. When the teacher marks my script, she’d penalise me for “skipping steps”. Well, those steps were taken but just not on paper.

It is very different in the real world where we also get penalised for skipping steps:

• Trying to submit an application without sufficient documentation
• Rushing to give customer a proposal without first understanding what is truly needed by them
• Booking your vacation without thoroughly checking your calendar for conflicting commitments

In all of these cases, steps were indeed skipped, intentionally or not. And there are going to be consequences to them. Often, the time or money saved may not be worth it to deal with the consequences.

However, if you are able to perform those steps through other means which is more efficient and brings other benefits, such as what I did in school with math problems, then you can still get to the results well and good. That’s actually useful in the real world. The nuance that we need to learn from this childhood lesson is that you can short-circuit a process only when you can address every step adequately.

What do you find yourself risking?

• Financial capital: either through passive investments or actively starting and reinvesting in a business
• Knowledge: by pushing the boundaries of what you know and applying that towards your decisions (whether it is to challenge how things works or put your money on things you believe will work when others don’t).
• Time & efforts: by spending time and effort to build something. Maybe it takes some money but mostly just your time and effort. And the value of what you build as a result is worth way more than the time and effort your put in. Or it may not be.
• Reputation & connections: by selling or recommending people in your network and connection some product or services to earn some returns. The product or service might work out for them, it might not.

Whether you think of it this way or not, you are already taking risks in life. Being mindful of how and what you take risks on might be a useful skill you missed out in school.

In “Thinking in Bets”, Annie Duke identified this problem of “resulting” – that a bad outcome automatically points to bad decisions. I’ve written about how I dealt with regrets in the past and I think understanding our tendency to “result” (I’m using it as a verb to the word “resulting”), is going to help us deal with how we reflect, and consider our regrets.

Regrets always involves a strong dose of “I should have known” except you didn’t know and whether you “should” is a moot point by then. And because you had to make decisions under situations of uncertainty, the process determining the decision is more critical than the decision itself.

For example, due to some really tight scheduling and limited buffer time in our weekend plans, we ended up neglecting our dog quite a bit at home a particular day. It would have made sense in retrospect to arrange for it to go on a day care and we would have been happy to arrange. But we had thought it was possible to have more time in-between our commitments so it was fine.

Except of course eventually it wasn’t, as our commitments overran and gave us razor thin slice of time gaps to be back home with the dog! We could choose to say it was a bad judgment but we cannot think the decision not to arrange for day care was bad. There is a fine line between those thoughts but in terms of mental health and hygiene, it makes a huge difference. Resulting causes unnecessary stress, anxiety and afflicts pain on ourselves and others. It would have been better for us to focus on dealing with results rather than being caught up with whatever led to it, especially when there was a lot of uncertainties prior.

By the time I was in my late teens and in army, I was known around my friend circles to be a walking wikipedia. It was mostly because I retained so much random trivial information across a wide range of topics that people find it rather amazing. Practically, it was useless despite the impression people get. In fact, it only undermines you if you start believing that you actually know it all just because you retained random tidbits of useless information in your mind.

So by the time I went to college, I was trying to see how that can be useful. I found knowledge around pop culture, movies and all useful socially. It helps to establish some connection but most critically, within these tidbits, you distill the zeitgeist and start to be better able to anticipate and read people better through those lenses. Scientific knowledge themselves are of practical importance but more critically, the patterns of logical deduction rooted in those knowledge is what helps us discover new connections.

And despite the fact that most of education, I went through pretty structured learning, I realised that I was actually not good at structuring the knowledge or information which I picked up tacitly. So through work, I learnt a bit more how to organise and make those information useful. The ability to aggregate seemingly useless bits of info to form a big picture becomes more critical at this stage.

Knowing, is not a switch. It is a process. One that evolves, that deepens.

People with a sense of mission in the workplace can be really hard to manage as it turns out. When you work on projects that have only tangential connection with their mission, they might not be motivated. When your projects are not aligned or even falls severely short of their sense of mission, they can cry foul and risk your business. They might have no interest in chasing the short term KPIs or pleasing you as a manager.

And with them, you might risk not getting the exact outcomes you or the organisation desired – especially when the organisation says one thing about their ideals and principles but is trying to do something else. So you might not want these idealists around.

But often, that is the only choice, and they are the only ones worth paying for. There are plenty of talents out there who are brilliant in what they have to do in the short run and deliver on KPIs but lack the sense of mission that the organisation badly needs. Organisations are like humans, and profits can be like good food, mistaken as the raison d’etre of living. People with a clear sense of mission helps put the organisations back on the right track.

It started with intra company media, stuff you post on the intranet, send in company-wide emails, the front you put up in front of bosses. There is the self that we bring to work daily, it is part of professionalism but as we make our identities increasingly an external rather than internal thing, we begin to lose ourselves more.

Then comes social media and you even have to manage the perceptions around private life. Not that private isn’t private anymore but it has become ways to humbly or not-so-humbly brag. And so there is pressure to present a self you want everyone to see. Genuine private life became even more private and perhaps darker in nature. Again, ourselves are somewhat lost.

Authenticity as a movement came out against this. All these perception management. Yet it can get abused and people acting unprofessional and giving in to their lack of discipline try to make themselves feel better by peddling around authenticity. I think the key compass here is your internal sense of identity. Where does it come from? Where and what is your anchor?

For Asians, it’s potentially more difficult to give than to receive direct negative feedback. And as I mentioned before, giving feedback should be a course. I have also suggested tips and ideas.

The problem is we don’t remember them because culturally, it’s just such a taboo; we don’t want to “hurt” others. It just reflects how feedback have been weaponised before in our culture so often and far too much. Whether in the form of “advice” from elders, or just unsolicited statements from distant family members.

The thing is, negative feedback can only hurt us to the extent we allow them to. If we don’t take advice from someone, why should we be taking their criticism?

What do you ask of your boss? And are you where you would like to be as a boss? Or have you fully embraced your identity as the boss and realised you can’t understand why the staff reporting to you simpy cannot understand the constraints you are under?

Every choice you take boils down to 2 different directions: you are either reinforcing the status quo or trying to change it.

Which choice are you tending towards?