Sunday Wisdom No. 72

Our thoughts and decisions have a set of taken-for-granted assumptions behind them. Unless we uncover them, it’s almost impossible to understand the flaws in our logic and thinking, if any.

Welcome to Issue 72

👋 Hi, I’m Abhishek. Welcome to Sunday Wisdom—a weekly advice column on decision-making, clear thinking, creativity, and everything else that’s stressing you out in business and life. I appreciate you being here. If you are loving Sunday Wisdom, you can buy me coffee or share this newsletter with a friend.


What I’m Thinking

Invisible Rules

We may not know everything about the world, but we don’t wander about in confusion. Despite our ignorance, our world isn’t dark. We tell ourself a coherent story about what’s going on based on the little we know, and effortlessly make sense of the world around us.

The truth is, we don’t know what we don’t know. Each of us have a unique set of assumptions and rules that we subconsciously follow in order to go about life. Therefore, when we make a decision, we never start from zero.

Every thought or decision has a set of taken-for-granted assumptions behind it. These are the Invisible Rules that guide us. Unless we uncover them, it’s almost impossible to understand what’s really driving our decisions, and what are the flaws, if any, in our logic and thinking.

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Create for Yourself

If you are a creator, a very common question that troubles you is, should you create for yourself, or for your audience? And, what’s the difference? How does it effect you or your work quality? Does it really matter? In this video, I answer these very questions.


Thinking is Hard

Last week I announced RE:Thinking, my live online course on better thinking.

If you wonder, is thinking really so difficult that one would need to take a course, the short answer is: yes! Thinking is difficult, and most of us don’t know how to think properly.

All of us know and engage in Passive Thinking which is our default thinking, but very few of us—less than a minuscule—know how to practice Structured Thinking.

Passive thinking is prone to cognitive biases and mental errors, while Structured Thinking is targeted, and helps us quickly synthesise what we already know to generate creative ideas and make better decisions.

Structured Thinking is indispensable for top performers who want to take risks confidently, stand out from their peers, and position themselves for the best possible future.

If you are a student, a teacher, a researcher, a creator, a decision maker, or a knowledge worker who actively seeks information to become a better thinker, RE:Thinking is for you.

You’ll learn how to quickly identify and avoid garbage information, how to learn more and consume less, how to reinterpret others’ ideas to fit your needs, how to organise your growing knowledge in various fields into a structured form, how to constantly rediscover and reinterpret already known information, how to identify gaps in your understanding and plug the loopholes, how to generate new ideas based on what you already know, and more.

The information we consume turns into thoughts; our thoughts turn into ideas, and our ideas define us by turning into decisions and actions. Better thinking is an indispensable art. I’ve spent the last couple of years polishing a framework and transformed myself from being a passive consumer of information to an active generator of ideas. RE:Thinking is the culmination of that effort. Even if you are a tiny bit interested in better thinking, take some time to explore the course.

Explore RE:Thinking


What I’m Learning

45 Years. 6 Lessons. 

Joel Goldberg, a software developer, recently retired after working in the industry for over four decades. He shares some of the lessons he learned over his career. These aren’t limited to software engineering. We all can take away something from this.

  1. Beware of the curse of knowledge: When you know something it is almost impossible to imagine what it is like not to know that thing. It is the root of countless misunderstandings and inefficiencies.

  2. Focus on the Fundamentals: They are teamwork: great teams build great software. Don’t take it for granted; trust: teams move at the speed of trust. Be the kind of dependable person you would want to work with; and communication: communicate honestly and proactively.

  3. Simplify: Fighting complexity is a never-ending cause. Solutions should be as simple as possible. When you can use fewer technologies, do so.

  4. Seek first to understand: If you want to influence and work effectively with others, you first need to understand them. Actively listen to understand their feelings, ideas, and point of view before you begin trying to make your own thoughts known.

  5. Beware of lock-in: There will always be the next hot productivity product that will promise to revolutionise how work gets done. What is not always as obvious are the constraints you may be committing yourself to. Lock-in means significant cost to change. Choose wisely. New is not always better!

  6. Acknowledge when you don’t fit the role: At some point in your career you may find yourself in a role that isn’t a good fit. A bad fit isn’t a character flaw, but it’s a problem you shouldn’t ignore. The key is to have the self-knowledge to recognise what is happening, and get yourself out of an unhealthy spot. Being unhappy is in no-one’s best interests.

— What I’ve Learned in 45 Years in the Software Industry


4 Hour Entrepreneurship

In 4 Hour Work Week, Tim Ferriss outlines interesting tips on managing resources to get the highest ROI on your work. What is objectionable, however, is the hack-your-way-to-success mentality it has spawned in entrepreneurial circles.

It’s a mindset that is antithetical to everything entrepreneurship is about. A mindset you see when you hear people talk about having an amazing idea that they want to farm out to a young college student who can code.

It’s a mindset that assumes entrepreneurship is a series of networking events and fundraising meetings, or some silver-bullet business connection one needs to have in lieu of a real distribution strategy. It’s taking a passive approach to an active undertaking.

To be successful over the course of a career requires the accumulation and application of expertise. And expertise is gained from curiosity, and a mindset of taking one’s craft very seriously.

If you step up to the challenge, you’ll realise that a startup demands rapid accumulation of knowledge. In this aspect, a startup is actually a teacher. And it’s only while exploring unknown territories and facing the headwind of challenges that you actively engage in both professional and character growth. But if you outsource this challenge, you don’t learn anything, and never build expertise.

That is why the passive, 4-hour mindset is so self-defeating. Lounging on a beach or travelling the world while choosing not to actively engage in building your arsenal of expertise is equivalent to professional malpractice.

If you are to optimise for anything, optimise for the long term. Use the challenges of your business today to build mastery in your craft. There is no guarantee that all your ventures will succeed, but that mastery will bend luck in your favour eventually.

— The Alternative to the Four Hour Work Week Mindset


Not Working

After Sahil Lavingia gave up his dream to build Gumroad into a billion-dollar company, he acquired a new asset: time. He used it to take classes on writing and painting.

Because he was burned out and didn’t want to think about working any more, he instituted a no-meeting, no-deadline culture. This changed the trajectory from growth at all costs to freedom at all costs.

Thus, instead of having meetings, people at Gumroad “talk” to each other via GitHub, Notion, and (occasionally) Slack, expecting responses within 24 hours. Because there are no standups or “syncs” and some projects can involve expensive feedback loops to collaborate, working this way requires clear and thoughtful communication. Everyone writes a lot. Everyone writes well.

There are no deadlines either. Shipping is incrementally, and launches are done whenever the stuff in development is better than what’s currently in production.

Growing 85% year-over-year, Gumroad has no full-time employees. Most entrepreneurs have two options: work a full-time job and hustle nights/weekends, or leave their job and risk everything to start a company. Gumroad provides a third way: contract 20–35 hours a week, incubate ideas, and work on a side hustle.

The internet has enabled new ways of working, but we’re just starting to see them unfold. There are many ways to make work work. Gumroad’s is just one.

— No Meetings, No Deadlines, No Full-Time Employees


👋 That’s All!

As always, please give me feedback. Did any of the stories resonate with you? Do you disagree with anything? What do you want more or less of? Any other suggestions? Please let me know in the comments.

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