123 - Six rules that I follow as personal commandments


personal development

Part 1 of 2 on how to use rules to your advantage

Why do we love making rules for the groups and organizations we’re a part of but not so much for ourselves?

People don’t argue against rules.

Rules preempt negotiations.

Negotiations take up energy, plus their outcome is not certain.

Rules help manage uncertainty by reducing the number of possible outcomes.

Managing uncertainty in a group matters because everyone thinks that the average group IQ is lower than their individual IQ. Say that again?

👉We think too much of our ability to handle ambiguity and too little of others’ ability to do the same. That’s why we like having rules for others, but not so much for ourselves.

The whole point around rules and process is that variations are bad and predictability is good. This was true on the factory floor, not in knowledge work.

Groups contribute best when their diversity is unlocked, not locked in. That is when intra-group differences make the whole greater than the sum of the parts. Rules and policies stamp out variations by disincentivizing coloring outside the lines. But why should we welcome variations in knowledge work?

💡Genetic mutations are bugs in the homo sapien software that end up upgrading it. But they're accidental, so evolution happens at its own sweet pace. As a founder / leader, you would want your teams and companies to evolve and adapt as well but not at their own pace. You want to set the pace. Then have fewer rules. Let the variations happen. It is called creativity, by the way.

Where we need rules instead is as personal commandments to guide our behavior everyday toward our big desired outcomes–health, relationships, sense of purpose.

Here are six rules I follow for myself. These have been important guardrails for my life for the last three years. This list is not all, but it tells you the areas in my life I’ve spent the least brain power on. To me, a good rule is one that once made saves your prefrontal cortex running costs and frees it up for other more important things.

💡Because when there’s a good rule, you don’t have to decide. You’ve already made the best decision possible.

Except for a few, the ideas behind these rules are not mine. They’ve come from people far smarter than me. The only tweak I’ve made to the rules themselves is make them sound more like an adage.


1️⃣**No meeting in the AM **- Shane Parrish

I block the mornings on my calendar two months at a time. I’ve been doing this for a long time. For the last six months, for example, my first meeting has started at 11.30am. Of course, on the odd day, there are morning meetings I can’t say no to but by and large, morning time is my maker time. This is the time when my energy is high and I can take up big chunks of work. It is thanks to this window that I’ve developed a habit of documentation at work. I maintain decision journals, concept notes, but not powerpoint.

Doing well in the morning, I’ve come to realize, energizes me for the afternoon’s inevitable meetings. If my maker and manager time were reversed in the day, with no other change, I would probably get done half as much and twice as bad.

Hidden within this rule is another: Forget managing your time. Manage your energy.

**2️⃣Never say Yes on the phone. **- Daniel Kahneman

I don’t get even a smidgen of the number of telephone requests that Nobel laureate Kahneman does but I can relate to the social pressure he feels in those uncomfortable moments of expectancy after a request is made. A friend asking for a drink, an acquaintance asking for a favor, someone asking for your time.

The trick in such situations is to slow things down and introduce a pause before committing. The pause brings you down from a hot state to a cold state. The gap between the two is the difference between owning your time and renting your time.

When we say Yes to coffee a month ahead, our answer depends on how enjoyable we think that encounter is going to be. When we say Yes to coffee tomorrow, our answer depends on how feasible it is—Do I have the time? Will I make it to the venue? Is there anything I’m waiting on that may scupper the plan?


**3️⃣Don’t offer advice without checking if they want it first **- Adam Grant

Organizational psychologist and author Adam Grant admits to being terrible at giving advice. He calls himself a logic bully. He used to bring a scientist’s approach to counsel-giving and think that making a case with airtight logic would sort the matter out. But when that only seemed to rile up those who sought his advice, he realized his folly. He was depriving the advice seeker of the chance to own her own choice. And that mattered. So now in his own words

I go the extra step and say, “And why are you coming to me? Are you here because you want my advice? Are you here because you’re looking for my validation of a decision you’ve already made? Or are you here because you want me to challenge your thought process?”

PS: Another luminary, Yuval Noah Harari, believes he’s the agony uncle to a number of his friends. The reason they choose him is that he’s a good listener. He lets them talk. Most of the time, they just want to vent and he allows them that luxury. This strategy is hard to pull off if you’re impatient but it works like a charm for me with my wife. I just have to listen.


**4️⃣Never ask ‘What do you think?’ if you’re fishing for support. **

There are two situations when this rule is handy. One, when you’re asking a friend or a peer for advice. Here, you’re the advice seeker to Adam Grant’s advice-giving logic bully.

The second is in decision situations when you pretend to be collecting information but in truth you’re not. You just want reconfirmation. So, you drop questions that may disconfirm your belief and pretend to probe with ‘What do you think?’

What do you think? Is this dessert any good?

What do you think about the iPhone 15? (to the salesman)

What did you think about our product?

There’s such a thing as a stupid question and What do you think? comes awfully close to one.


**5️⃣Never accept a problem definition as it is. **- Shane Parrish

This is something I teach in my framing class. The idea is simple: How we define a problem determines what solutions we see and what remains in the shadows. But this slips past us most of the time.

Our boss comes to us with a problem and we jump on it. When we accept the problem frame as is, we do not ask: Is the problem framed too narrow? Does the frame capture all that’s important in the solution? Does the frame point us in the direction we want to go?

Optimizing for speed at this point can be counterproductive because we may lose track of because of a poor choice of frame.

Whenever a problem is presented to you, refuse to take it as it has been described. Take a step back. Ask an unlock question: What has to be true for this problem to not exist in the first place?

If you notice, this question forces you to make a clear choice. By asking this question, you’re asking yourself: ‘Am I making an early-warning system so that the problem doesn’t occur OR am I making a rapid-response team to solve the problem quickest when it occurs?’ If it’s the latter, you better be ready to have to solve it again and again. But if you want to prevent the problem from recurring, you gotta look at the problem from other angles.

📢I’m doing a free session on decision frames for all subscribers on Nov 4. Details here. Subscribe now if you haven’t already. Hope to see you!


**6️⃣Don’t give your two cents to improve on someone’s ninety-seven cents **- some guest on The Knowledge Project podcast

I used to like being a smart fish in a small pond. It got me noticed when I was younger and working to make an impression but then this tendency went past its use-by date. Only no one gave me the memo. So I continued being the one who would chime in to point out tiny warts in someone’s idea—an idea they had just presented to the company management with care and hope. I did it to show that I’m smart but also to improve the idea. What I failed to account for is that sometimes, oftentimes, people are not looking at you to improve their idea. To do that, you need their permission first. What is more useful is for you to recognize the bigger goal. If letting the gaps be (until an opportune time) meant you now had this deep font of passion and energy of the idea-owner to harness, then you were a fool to lose any of that to make a tiny improvement.

Think outcome over ego, always.

This week we dove into using rules as personal guardrails to design your life smartly, thoughtfully. Next week I’ll talk about the default rule for groups: have no rules. If you don’t have rules, how do you stop things from slipping into chaos? What do you have to do to get the best out of groups? How to trigger creative mutations?

Through something I’ve come to call the Talent-Transparency Framework, and learning from the cultures built at Netflix and Stripe, we’ll see how removing controls can unlock growth potential in organizations.

  1. Expected value theory stipulates that we go with choices where the expected value is positive. Where it is not, we are better off sticking to the status quo.
  2. But going with expected value theory assumes that our assumptions behind the math are solid. These assumptions are our mental models about the world. The more accurate they are, the better we can anticipate reality.
  3. When it comes to volatile environments, deeply held assumptions on which we have based decisions whose consequences play out repeatedly do not hold forever. Our models need correction.
  4. Deliberate mistakes are choices made whose expected value is negative. Not making a deliberate mistake has a higher expected value than making it. So why make mistakes intentionally?
  5. Deliberate mistakes is not the same as going against convention. It is going against your own assumptions, whether or not they are counterintuitive, with the intention of testing them.
  6. Businesses can fail while doing everything right. Deliberate mistakes open the door to success by intentionally doing something that seems wrong.

Introduction to the concept: The article discusses the idea of deliberately making mistakes to challenge conventional wisdom and expand the understanding of sense, emphasizing the importance of this practice in decision-making.

Distinction from routine decision-making: Making deliberate mistakes stands apart from routine decision-making processes and involves questioning fundamental beliefs and assumptions.

Conditions for purposeful mistakes: Deliberate mistakes are advocated when there is a substantial potential benefit (high upside) relative to the cost (small downside). This approach is suitable for repeated decisions, non-formulaic problems, changing business conditions, and situations where familiarity with the problem is limited.

Steps to purposeful mistakes: The article outlines steps for making purposeful mistakes, including identifying critical assumptions, ranking them based on suitability criteria, designing the mistake, implementing it, and learning from the process.

Analogy with seatbelt and barbell strategy: The article uses the analogy of managing risks similar to wearing a seatbelt in a car, balancing the low risk of car failure with the high risk of seatbelt failure. It introduces the concept of the barbell strategy, which involves balancing safe, obvious choices with risky, non-obvious ones.

Conclusion on minimizing regret: The conclusion emphasizes the importance of learning from mistakes and exposing faulty assumptions to minimize regret, acknowledging that deliberately making errors of commission can lead to valuable insights and knowledge.

Example of learning through experimentation: The article ends with an analogy, suggesting that experimenting and making mistakes can be a fast and effective way to learn, even if it involves unconventional or risky actions like sticking forks in electrical sockets to understand electricity.

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