At around the 41:08 mark, François showed this slide.

François used the Type1/Type2 architecture made famous by Kahneman as an analogy with LLM (Type 1) and symbolic tools (Type 2).

I’m mentioning this because I came across this other post recently about consulting.

In case the embed doesn’t work, it says BCG taught the author the technique to break down a hard problem as Qual > Quant > Qual. Which is a parellel to François’ point of sandwiching Type 2 reasoning with Type 1 deep learning.

If you’re familiar with the general idea of LLM, that to build up a good Type 1 system, you need lots of data. It’s as if quantity at a lower-level (data) generates quality at a higher level (intuition/perception) in a hierarchy.

For Type 2, you need to spend a sufficient quantity of time. Either to perform the discrete search during the problem solving, or to even learn the skills associated. For example, it’s arguable we put people through formal school for years essentially to learn all the Type 2 reasoning skills and habits.

Let me know if you see any other fields where the same pattern applies

The Synchronicity of Wrong Answers

I'm a big believer in synchronicity, and when two related incidents occurred on the same day, I knew I had to write about it. These experiences, one from my computer science studies and another from my tennis lessons, both underscore a powerful strategy: the art of being usefully wrong.

Incident 1: Prototyping with Wrong Answers in Coding

As part of my master's program in Artificial Intelligence, I recently shared a problem-solving strategy in my Python class forum. I call it "Prototyping with Wrong Answers." Here's how it works:

1. Identify the problem: You have an output that's missing something.

2. Overcorrect: Add too much of what's missing in the simplest way possible.

3. Analyze: Now you have two wrong answers on opposite sides of the correct solution.

4. Iterate: Adjust incrementally, moving closer to the right answer with each attempt.

This strategy, sometimes called "hill climbing" in computer science, helps in two ways:

• It develops intuition about the problem and solution space.

• It provides a sense of progress, boosting motivation.

The key is to embrace being wrong as a stepping stone to being right. By exploring multiple incorrect prototypes, you're mapping out the terrain of your problem, making it easier to find the optimal solution.

Incident 2: Aiming Off in Tennis

Later that same day, during my tennis lesson, my coach gave me an instruction that initially puzzled me:

Coach: "Aim your backhand to the rightmost cone."

Me: "Should I aim my forehand to the leftmost cone then?"

Coach: "No, just your backhand to the right. It'll make your shots more accurate."

After a moment of confusion, I realized this was similar to a technique used in military marksmanship called "aiming off." When a rifle can't be adjusted further, soldiers are sometimes instructed to aim slightly away from the target to compensate for consistent errors.

My coach was using the same principle. By telling me to aim right, he was correcting my tendency to hit too far left, ultimately improving my accuracy.

The Value of Being Usefully Wrong

These two incidents highlight a crucial lesson: sometimes, the fastest way to be right is to be deliberately wrong first. This concept aligns with Warren Buffett's famous quote, "It's better to be roughly right than precisely wrong."

To supplement Buffett's wisdom, we can add another perspective: "Sometimes, the quickest path to being roughly right is to start by being precisely wrong." This follow-up emphasizes that deliberate, strategic errors can be a powerful tool in problem-solving and skill development.

In both coding and sports, this approach offers several benefits:

1. Rapid feedback: By making deliberate "errors," you quickly gather information about the problem.

2. Intuition building: Exploring wrong answers helps you understand the boundaries of the correct solution.

3. Overcoming perfectionism: It encourages action over analysis paralysis.

4. Efficient learning: You often learn more from mistakes than from immediate success.

Applying "Useful Wrongness" in Your Life

How can you leverage this principle in your own work or hobbies?

1. Embrace imperfection: Start projects with the understanding that your first attempt won't be perfect.

2. Use extremes: When stuck, try solutions that go too far in either direction.

3. Iterate quickly: Make small adjustments based on what you learn from each "wrong" attempt.

4. Reframe failure: See each mistake as valuable data, not a setback.

Remember, the goal isn't to be wrong for the sake of it, but to use controlled errors as a tool for rapid improvement and problem-solving.

By adopting this mindset, you might find that your "mistakes" become your most powerful teachers, guiding you toward solutions you might never have discovered through conventional thinking alone.

Hi, it’s me Kimsia and yes, I haven’t updated for nearly a year. After I officially signed off on the biggest contract as an independent software vendor (a story for another day) in April 2023, I allowed myself to live a bit more.

One huge implication of letting myself live more is that I’m no longer doing random stuff out of fear and desperation. Admittedly, this newsletter was a part of that random flailing. Hence, the massive drop off in updates for almost a year.

I don’t want to be too reflective in today’s post. Instead, I want to talk about one concrete new thing I did during this period of living more.

Some of you may know that I was in a mastermind group with other SaaS founders in Rob Walling’s microconf community. And when I got stuck with my SaaS idea was to help another founder with his. For anonymity’s sake, let’s call this gentleman, J.

No Code Agency Wasted Founder’s Money and Time

J’s issue at that time was that he had spent tens of thousands with a no-code Bubble agency on his SaaS idea with little to show for. I played with the prototype the no-code team had produced. It was pretty buggy.

After a mastermind session when J finally had enough and wanted to try a different product idea, I thought I will help him on a separate product idea he had. A fresh slate is always easier for me to help in.

I Wrote Zero Code But I Tried to Help in Other Ways

I emphasized to J I will NOT write any code. And given it’s a new idea, I started by creating a database schema with him jointly.

It’s been my observation that when you design a database schema with the product owner’s or end users’ input, it forces the team to confront any vague assumptions early and clarify them early in the process.

Clarifying Assumptions Before Writing Code is Good

It’s supremely important to clarify assumptions. The earlier you can do that, the cheaper it is to build a working product. Preferably before writing any code. And creating a database schema forces enough rigor akin to writing code without it being actually writing code outright.

Once, the database schema was done, I guided J on how to hire technical people on Upwork. Given that J was highly creative, he had no issue coming up with the UX look and feel of his new product idea on Figma on his own. If it was someone else, that would have been the next hire.

We Got Some Luck with Hiring

Instead, the first technical person we hired is for the frontend. Someone who can transform J’s Figma into frontend code. We found someone suitable after we followed my adapted version of Derek Sivers’ How2Hire advice.

By the time we are ready for the backend, we got lucky when Y person recommended a friend he worked before, A.

After 3 months or so, the first prototype was live, albeit in development environment. Another 3 months or so, the new product was making its first dollars in production. J’s pretty influential with the target audience, so making sales was to be expected and in his wheelhouse.

The Whole Team was Entirely Remote

The whole development process from idea to making first dollars was pretty fast and cool. Every member was in a different country and timezone. We got revenue roughly months in. Personally, I never took part in a product going live so quickly and making some money, whilst never writing any code.

That was a first for me.

To thank us, J even got us gift baskets. I received two in total. One in September 2023, and another in Feb 2024.

Starting Masters Degree School and My Learnings

Now that the team has grown substantially, and I’m starting my Masters degree this week, I have less energy to advise J. So, I’m slowly weaning myself from the team.

The good thing is, over the past year or so, I can see that J is starting to get better at hiring and managing tech people. And I’m happy to play some part of it.

I’m confident J will get better. The SaaS is growing, and has its own cadence. If the cadence changes to something explosive, I don’t rule out cutting my Masters’ study short.

The whole experience taught me a few things:

1. It’s totally possible personally to build a digital product that makes money without me writing code. This is a first for me.

2. It’s totally possible personally to build a team that’s entirely remote. I already know this, but only in theory. To have actual practical experience is still quite revelatory. Companies and teams with more resources should consider this option. After all, there are more smart and talented people outside your company than inside.

3. Working with people who bring different skillsets and aptitudes is crucial. The early team — consisting of J, Y, and A, plus me advising J — had 4 very different characters with very different skillsets. Working with a team this diverse was a first for me. And I learn how important that each person brings a different skill to the table that fits the problem at hand. Weirdly, we didn’t set out to build the team this way. It evolved naturally that way.

4. Spaciousness was important.

Spaciousness

It’s a bit hard for me to explain this term despite learning it a couple years ago. I’m not confident if I understand it fully. In this specific context, I am willing to wager that there was a right amount of spaciousness that allowed for the product to move from idea to dollars so quickly.

Spaciousness is an attitude: the willingness to suspend the process of meaning-making. Spaciousness is the willingness to allow unknowing, uncertainty, confusion, ambiguity, meaninglessness.

— from Spacious freedom | Vividness

J was starting fresh with a new idea. We started with brand new contractors in Y, and A. I myself had no stake in this product. So, I was a lot less anxious, when inevitable issues cropped up. I had previously worked on stuff where I worked far harder with much less success. This was new, and pleasantly surprising for me.

Yes, spaciousness is an attitude. But the thing about any kind of attitudes is that they’re easier to foster and maintain when the environmental conditions are conducive. And, maybe we got lucky stumbling onto the right conditions that engender this spaciousness? I’m not sure.

In any case, trying to recreate the right conditions for me to engender this spaciousness, or "spacious passion" is a direction I’m exploring more. Particularly when it comes to my own product ideas.

Future Updates

That’s the update I have so far. I’m not stopping my experiments, and building. Just that I won’t update as frequently as other newsletters. Every time I come up with some target, life takes me into directions that make an absolute mockery of my plans. No promises this time.

You’ll get the updates when you get them. Until then, keep safe.

In other words, McConnell knows his stuff when it comes to software engineering.

He has produced many useful resources and of his many gems of wisdom, there’s one I find myself referencing the most often. That’s what I will cover in this article here.

The public link is at YouTube which I have also embedded below. The most important part starts at 10:34 and ends around 17:36.

I’m not going to repeat every detail of this concept. He has said plenty in public YouTube and in his company’s paywalled training videos . My intention is to have my own concept handle / API endpoint for this concept I can link to whenever I mention it in future conversations.

Summary of Key Points

• There are 3 phases when it comes to software development and there’s a linear order to them.

• The phases are usually called Requirements, Design, and Implementation. McConnell prefers to call them Discovery, Invention, and Construction. I prefer to use verbs and fewer syllables, so I will use my preferred terms going forward: Discover, Design, and Build.

• The order is: Discover → Design → Build.

• McConnell has a single key insight about these 3 phases that has several key implications. The key insight is that the phases overlap during a software project.

• One implication is that you begin the later phases before the earlier phases are complete.

  • You start Building before Discovery and Design are complete.

  • Design work starts before you finish Discovery.

• Another implication is that some “upstream” work depends on “downstream” work. Examples such as:

  • You cannot finish writing a requirement in Discovery because you need to do some Design work to test that it’s feasible.

  • You cannot complete a Design because you lack implementation details. Details that you learn only after you try to Build something.

• McConnell likens the nature of software projects having overlapping phases as a wicked problem. He has a nice and clean definition of a wicked problem, calling it a “problem that cannot be fully defined until it’s at least partially solved”.

• His charts make it easy for him to make the following bold claims:

  • The degree to which a software project is a wicked problem varies.

  • And the degree is related to the amount of overlap.

  • So if you can reduce the amount of overlap, you can reduce the “wickedness” of a software project. This is the boldest claim and bears repeating: you can reduce the wickedness of a software project.

  

  

QnA

Q: Is it possible to reduce the overlap to zero?

A: I don’t think so. It’s possible to reduce the overlap to the absolute necessary bare minimum (ANBM). But this leads to a different question about two kinds of ANBM.

Q: What do you mean by “two kinds of ANBM”?

A: The two kinds are: theoretical and practical.

The theoretical ANBM which you only realize on hindsight or you assume perfect knowledge.

The practical ANBM based on the available information at the moment when making decisions.

You can get practical ANBM as close to the asymptote that is the theoretical limit with experience across multiple projects, but it’s like seeking perfection. You can get close but never actually reach it. The more any one project differs from previous projects that you have done before, the wider the gap is between the theoretical and the practical.

Knowing when to be at peace with that gap, and when to be dissatisfied and wanting to do better is the difference between a self-harming perfectionist and a productive high performer.

References

Responding to Uncertainty with the Intellectual Phases Model | Steve McConnell

Construx OnDemand - Understanding Software Projects (vueocity.com)

Unsubscribe below if this newsletter no longer works for you. I turn off unsubscribe alerts. So, I won’t even know you did. 😊

In Rick Rubin’s The Creative Act, he has this chapter called “Seeds” where he wrote

In the first phase of the creative process, we are to be completely open, collecting anything we find of interest.

We can call this the Seed phase. We’re searching for potential starting points that, with love and care, can grow into something beautiful. At this stage, we are not comparing them to find the best seed. We simply gather them.

..

Collecting seeds is best approached with active awareness and boundless curiosity. It cannot be muscled, though perhaps it can be willed.

…

Having a specific vision of what a seed will become could serve as a helpful guide in later phases. In this initial stage, it may cut off more interesting possibilities. An idea appearing to hold less vitality may grow into a beautiful work. Other times, the most exciting seed may not ultimately yield fruit. It’s too soon to tell. Until we are further along in the process and the idea has been developed, it’s impossible to assess these germs of an idea accurately. The appropriate seed will reveal itself over time.

Placing too much emphasis on a seed or dismissing it prematurely can interfere with its natural growth. The temptation to insert too much of yourself in this first phase can undermine the entire enterprise. Be wary of taking shortcuts or crossing items off your list too quickly.

…generally preferable to accumulate several weeks’ or months’ worth of ideas and then choose which of them to focus on, instead of following an urge or obligation to rush to the finish line with what is in front of us today.

The more seeds you’ve accumulated, the easier this is to judge. If you’ve collected a hundred seeds, you might find that seed number fifty-four speaks to you in a way that none of the others do. If number fifty-four is your only choice, without other seeds for context, it’s more difficult to tell.

Rubin, Rick. The Creative Act (p. 145). Penguin Publishing Group. Kindle Edition.

I feel particularly inspired by this chapter because it’s exactly the middle of the year at 1st July. And the weeks leading to it, I have been doing a few mid year reviews including what I’m doing this.

Some of you might be aware I’ve been in prolonged negotiations with my pillar customer over a renewal of my services. The negotiations and various bureaucratic procedures started since October last year and I’m happy to say I’ve signed my part of the renewal in the middle of June.

And, I’m looking at 50% increment of my revenue, which is significant. I attribute this to various factors but the biggest one might be because I was willing to be patient during the negotiations which stretched out to be nearly 8 months long.

This willingness to be patient further reminds me of this article I came across about leadership in Apple recently.

1 Big Thing: Separate How Hard from How Right A Path Is

This HBR article had this quote

A leader’s ability to be both partisan and open-minded is facilitated by two things: deep understanding of and devotion to the company’s values and common purpose, and a commitment to separating how right from how hard a particular path is so that the difficulty of executing a decision doesn’t prevent its being selected.

And then gave an example where a senior leader, Paul Hubel, wanted to introduce dual-lens camera with portrait mode in the iPhone 7 Plus in 2016 which was a significant better camera from previous versions. But as the release line nears, Hubel realized that there were still edge cases yet to be ironed out.

Sebastien Marineau-Mes, the VP to whom Hubel and the whole camera software team ultimately reported, chose to do the right thing.

Sebastien decided to

… defer the release of the feature until the following year to give the team time to better address failure cases—“a hard pill to swallow,” Hubel admits.

There are various aspects of my work, that are boring or incredibly technical for a general readership. So, I will use this newsletter as my example.

Over the past few months, there have been moments I have struggled between hitting my publishing timelines and quality concerns.

I have always chose to prioritize hitting publishing timelines over taking more time. As the Rubin quote above says, I had crossed “items off my list too quickly”. The way I convince myself is to make it it’s the right thing to do in terms of maintaining the discipline of publishing regularly.

But, of course, that’s just fear speaking.

There are plenty of writers I follow diligently and they don’t publish often. But, when they do, the quality is astounding. Julian Shapiro is such a person for me.

Giving the work the time it needs and not just the time I want to afford is also a form of Dirty Work.

The negotiations process with my pillar customer and the outcome strengthened my belief about the value of Dirty Work and patience at the right time.

And I will be taking bolder steps in that direction for the 2nd half of 2023.

I post a newsletter to all subscribers every 1st and 3rd Saturday of the month.

Unsubscribe below if this newsletter no longer works for you. I turn off unsubscribe alerts. So, I won’t even know you did. 😊

Two weeks ago, I sent my father to the hospital for a medical emergency.

Don’t worry, everybody’s fine at the end of this story. He was discharged by the next day. Just finish reading my story.

After he stabilized upon reaching the emergency department, the doctors wanted to ward him for an extra day for more checks and observation.

But, they needed to wait for bed space to free up. So, the medical team put my father in this in-between place called the Short Stay Unit (SSU) until bed space opened up. This was when I left him and told him I would be back later that Sunday evening.

In the middle of the day, my father called my mother to complain about leg cramps in in the SSU. He was too weak to stand. Instead of telling the doctors, he called my mother. 🤦‍♂️

When I visited him in the evening, he was in the wards. He repeated the same leg cramps in SSU story to me. But, now in the wards, he can walk properly. Which was certainly puzzling.

His conclusion? SSU is haunted. 👻

1 Big Thing: The First Obstacle to Dirty Work is Mental Masturbations

When I heard that from my father, my facial and body language was that of the dutiful Asian son. I uttered the word, “Ok” to signal I acknowledged his excellently thought-out hypothesis.

Internally, I was more like, “F%^7 this bull funky”.

In any case, I approached the staff nurse on duty, explained the ailments, and wondered why my father had leg cramps in the SSU earlier in the day but not right now in the ward.

The staff nurse checked her laptop and replied, “Ok, the initial diagnosis is that your father may have fluid in the lungs. So, the doctors gave him some meds via his IV drip to drain the fluids. Some people, but not all, may have side effects from that med which include leg cramps.”

Mystery solved. 👻

Why I’m Telling This Story

A while back, I wrote a 101 piece on Dirty Work.

In that piece, I gave a 4-part definition for Dirty Work which I am quoting:

From the study of all that material, I believe Dirty Work has four characteristics:

1. is painful, and to the extent you have little competition for it,

2. is necessary for growth such as to unlock certain career or business opportunities,

3. produces results that look magical to other people,

4. and is the opposite of a Technically Difficult solution i.e. it has almost no pre-requisites other than a willingness to get hands dirty.

But, like most things, what is correct at the theoretical sense, may not be enough for the practical aspects. None of the criteria talked about avoiding seductive narratives that pull us away from Dirty Work.

Easy and seductive narratives like the one my father told himself instead of seeking answers from the medical staff at the hospital.

Similarly, it would have been easy for me to dismiss my father’s concerns as mere superstitions and not do the extra leg work of asking the staff nurse.

Then, we have the classic case of two people talking past each other, sticking to their favorite narratives, and avoid disconfirming evidence just to feel right.

Recall the number 1 criteria I quoted about Dirty Work from above. Dirty Work is painful.

In fact, I would say Dirty Work is so painful, just thinking about it is just as painful.

All that pain aversion makes it so easy to avoid doing work and it shows up in us selecting our own favorite forms of mental masturbations.

Engineers’ Favorite Mental Masturbation is the Perfect Efficient System

From Urban Dictionary, the definition of Mental Masturbation is

The act of engaging in useless yet intellectually stimulating conversation, usually as an excuse to avoid taking constructive action in your life.

I would go further than Urban Dictionary. I would classify all kinds of psychologically comforting things which include attractive but wrong narratives that prevent us from taking on Dirty Work.

My definition of Mental Masturbation with respect to Dirty Work is

The act of engaging in useless yet intellectually stimulating conversation, self-talk, and other activities, usually as an excuse to avoid taking constructive action such as Dirty Work in your life.

An engineer’s typical form of Mental Masturbation to avoid Dirty Work usually takes the following form:

Ok, doing Dirty Work to solve pressing problem X is only 80% effective but definitely not efficient. It’s not perfect. Instead of doing Dirty Work, we should design and build this perfect system that’s ridiculously convoluted and would be so cool.

Now, you would think this post would have been better if I gave an example of the time I actually, erm, performed my own mental masturbation. That would have been more fitting for this post.

And you would be right.

But, that would have been too painful for me. So, you would have to make do with a story where I embarrass my own father instead of myself. :)

One Tweet To Share

Speaking of mental masturbations

I post a newsletter to all subscribers every 1st and 3rd Saturday of the month.

Unsubscribe below if this newsletter no longer works for you. I turn off unsubscribe alerts. So, I won’t even know you did. 😊

1 Big Thing: All VUCA Pursuits Need a Stop Loss

In day trading, there’s this term called stop loss. It works like this:

1. You set a limit of how much loss you can stomach on a particular stock.

2. Once the price drops to your stop loss limit or lower, your broker automatically sells it at the market price. Thereby, “stop” you from “losing” more.

I’m thinking about stop-loss because I need an equivalent of this term. For when we are trying to accomplish goals despite a lot of volatility, uncertainty, complexity, and ambiguity (VUCA). VUCA is common in many areas, including entrepreneurship and engineering.

Why This Matters

Let’s say you’re trying a small bet on the side in order to move out of full-time employment eventually.

You’re faced with two competing forces. If you don’t persevere enough, you may not see the fruits of your labors. On the other hand, you also don’t want to throw more resources at a venture that’s a lost cause.

Very similar to whether you should hold or sell a stock in day trading.

But, unlike day-trading where the stock price is a clear and unambiguous signal, there’s nothing this clear and universal across a wide range of entrepreneurial pursuits in different industries, be it a VC-funded startup, or a lifestyle business.

I have committed similar mistakes in both directions. My experience is that setting a 6 month limit and do a check-in is the best general stop-loss I can think of. Anything more precise or effective than that may have to be situation-specific.

Until someone comes up with a better term, I’m just going to keep using stop-loss as a stop-gap.

📖 Recent Read: Playing to Play, or Playing to Win

I re-read Are You Playing to Play, or Playing to Win? - Commoncog recently and it talked about the difference of playing to play and playing to win. An example is Roger Federer who wins while playing a harder game.

Federer uses a one-handed backhand — a notoriously more difficult technique than the two-handed version. He also happens to make it look easy. We don’t love him for that, of course — we love him because he does it while absolutely dominating the highest levels of tennis — at least for the good part of two decades.

The problem of playing to play is it makes winning harder. If you’re so hung up about playing to play that you self-sabotaged your chances of success, you’re being a scrub. The article quoted David Sirlin who first came up with the term.

A scrub is not just a bad player. Everyone needs time to learn a game and get to a point where they know what they're doing. The scrub mentality is to be so shackled by self-imposed handicaps as to never have any hope of being truly good at a game. You can practice forever, but if you can't get over these common hangups, in a sense you've lost before you even started. You've lost before you even picked which game to play. You aren't playing to win (emphasis added).

This inspired this week’s newsletter about strategic stop-loss. I initially thought of the following pseudocode:

1. If you’re playing to play, and still win, continue.

2. If you’re playing to play, but cannot win, stop and play to win instead.

The crux is, of course, knowing when to stop playing to play and switch, if you’re not currently winning.

💡Accidental Discovery: Co-working Space in Batam

I recently went Batam island for 4 days to get some writing done. A last minute customer request prompted me to research Batam’s native co-working space ecosystem because the hotel wifi couldn’t cut it.

I came across this Batamon.Asia by accident, and will be checking them out again. I seem to have caught them at a good timing as they are in prelaunch mode.

They also help to provide content and software people at entry level offering rates lower than university graduates in Singapore. It does make me wonder if it’s something I can leverage in the next 6 months after my negotiations with my pillar customer.

Trying Something New: 2 Week Ships

In the meantime, I’m trying to diversify my revenue with my SaaS attempts via microconf’s mastermind setup.

Sadly, I have a serious problem with shipping when it comes to my own initiatives without any external deadlines.

But, this phrase (SINGLE FEATURE APP) I stumbled upon in Alex Hillman and Amy Hoy’s launchftw pdf, made things click for me.

I’m still not doing things in the order the roadmap is currently advising, but at least I’m trying something new. Here are two ways I’m doing things differently.

1. I found a forum discussion where there’s documented pain by other people. So, I found evidence of an actual problem. As opposed to thinking up about possible problems in my head, which was my typical pattern.

2. I told my mastermind I will solve it as a single feature app within a 2 week sprint. Which I did, and talked about it with 4 loom videos in the same discussion thread. As opposed to over-engineering, which was my typical pattern.

Un-learning old habits is hard. I got some feedback about doing better in terms of marketing it from my mastermind group. If you have any, I’ll be happy to hear. Email me direct, or comment.

I’m keeping the “ship something every 2 weeks” tactic in the foreseeable future. Given my propensity to over-engineer, I will choose a 2:1 ratio where I will execute at least two fortnight marketing sprints for every one fortnight engineering sprint.

To end this newsletter issue back on the theme of stop-loss, I suppose I will run this "ship every two weeks" for at least 6 months before I re-evaluate. 😊

As always, I wish you and your family good health and good fortune.

I post a newsletter to all subscribers every 1st and 3rd Saturday of the month.

Unsubscribe any time when it no longer works for you. I turn off unsubscribe alerts.

1 Big Thing: Own Your Time

🚧 There was a planned upgrading at my apartment this past April.

I knew the month (April 2023) it would happen and the length of period (roughly 10 working days) required, but I wouldn’t know the exact start date until 2 weeks beforehand.

When I had the confirmed dates, I used the opportunity to visit two friends in nearby countries: Malaysia and Thailand.

👋 The Last Minute Visits

• 🇲🇾 In Malaysia, I first visited Friend #1 and his family over a weekend. I haven’t seen them in 5 years. And I enjoyed interacting with his brood of children, and dogs.

• 🇹🇭 In Thailand, I spent nearly 10 days at Friend #2’s apartment and got some 1-1 coaching from his tennis coach. The same friend I last visited back in August the year before.
  

Why These Examples Matter

Owning your time is a big deal. So, I want to use realistic, concrete examples to show and tell.

Even though I have yet to achieve 10k MRR in my independent business as a software engineer, it’s possible to transform the inconveniences into opportunities to reconnect with people in my life.

Viral internet content tend to showcase extreme results (Look at my Lamborghini! Look at my 100k MRR!!). Which may explain why they went viral in the first place.

But, extreme results are not helpful for serious independents trying to make progress.

1. Serious independents may dismiss their own progress because the size pales in comparison with these extreme results. (I made this mistake before)

2. No two paths look exactly the same even if they may end up in the same destination. Serious independents may take these well-meaning advice on the internet too literally and end up getting things wrong. (Also, I made this mistake.)

Three Notes

1. 🚨Be careful of wrong interpretations

I don’t want to mislead people to think I don’t have to do any work and all my current revenue (~7.5k MRR) is 100% passive.

As an example, on the Friday afternoon I set off to Malaysia on a 4 hr bus ride, I receive last minute requests from customers. Which meant

I had to work on the same weekend overlapping the Malaysia trip. But only for about 3 hours at most. I still had time for go-karting and good food.

Across the 2 weeks, I have taxes to file, contractual negotiations, classes to attend, zoom calls with internet friends to make, code to write while transiting across three different countries (Singapore → Malaysia → Singapore → Thailand → Singapore).

Despite the variety of demands life throws at me, I can still meet obligations with a mixture of applied willpower and adaptability.

2. 🕙 Cannot wait for perfect conditions

In the past, I kept deferring desires like visit old friends and pick up new sports. I felt they were distractions from my career goals.

Now, I see that the optimal attitude is to approach life and its obstacles/opportunities like a dance.

3. 🆗 You need to be okay with hard-to-explain, non-legible efforts

And a huge part of this "dance attitude" is that you need to be comfortable at not being able to explain what you do. Which I explain below 👇 in 📊 Graph of the Day

📊 Graph of the Day

I don’t want to sugarcoat things. Reading this post won’t automatically give you the same lifestyle as I do.

I took years to build up enough to meet the conditions for this lifestyle. Such as earning a stable revenue while being my own boss.

But, even when I did, I still kept an ascetic lifestyle. I didn’t give myself permission until by accident at late stages of the pandemic.

A huge part of the non-permission is because I used to think that effort and achievement had a straight line relationship like this.

The chart above has two flaws:

• One, I’m not so sure efforts is purely an objective measure. It’s more likely an interaction of objective and subjective elements.

• Two, even if it is a purely objective measure, I think there’s a difference between legible and non-legible efforts.

Now, I have updated my thinking to this graph.

Why This Matters

In the past, I over-index’d legible efforts. Looking back, it was my safety blanket.

Nobody likes to fail. Least of all, in a way that’s hard to explain to people. Legible efforts allow me to turn any setback into a kind of plausible, heroic failure.

Jeff Bezos has this quote

Entrepreneurs must be willing to be misunderstood for long periods of time.

— from https://www.goodreads.com/quotes/7954692-entrepreneurs-must-be-willing-to-be-misunderstood-for-long-periods

Being an independent software engineer is not the same as running Amazon in the 2000s. But, you also need to be willing to be misunderstood for long periods of time by people around you.

It’s a painful journey and still on-going. (Next stop: 10k MRR!) But I wouldn’t have it any other way.

As always, I wish you and your family good health and good fortune.

I did try writing daily for 30 days in Substack in early 2021, and immediately stopped writing afterwards.

I made a fresh attempt to get my writing muscles going, this time at TypeShare, between June and October 2022.

Scoping down to write 200-300 word essays in TypeShare, plus joining like-minded people at Newsletter Launchpad, made this transition a lot more successful.

The TypeShare experiment has served its purpose — namely to jolt me into writing more regularly. I’m shutting my account and migrating my two most popular TypeShare essays here.

Entrepreneurial Engineer

5 Tier Problem Hierarchy

I write software and I sell the software I write. Writing and selling it taught me the importance of being a problem-solver. One key thing I learn is: not all problems are equal. Not knowing this fact cost me a lot of time and money in the past. Learn from my mistake…

Read more

3 years ago · KimSia Sim

This one was and still is my most popular tweet at over 100 likes and 40 bookmarks.

Entrepreneurial Engineer

Course Correcting >> Move Fast With 70% Information

Working Backwards, a book by former Amazon executives, cited Amazon founder Jeff Bezos’ 2016 shareholder letter “most decisions should probably be made with somewhere around 70% of the information you wish you had. If you wait for 90%, in most cases, you’re probably being slow…

Read more

3 years ago · KimSia Sim

This one on Course Correcting, was cited by some people who follow me. Everything else other than these two essays in my TypeShare account was pure chaff.

Aside 

I received some interesting feedback from Sean (better known as skmurphy on Twitter) after he read my Course Correcting post. 

I'm meeting him coming early Monday morning SGT 7am to talk more over zoom.

Hope to share what we discussed in future newsletter issues or essays.

Substack Notes

Speaking of experiments, I recently tried my hands at Substack Notes. And from this graph, can you tell when I exactly tried it? You have one guess 😉

There’s an issue with Substack Notes where you cannot follow a person without also subscribing to their newsletter. I expect some of these new subscribers to be surprised by this mechanism.

If that’s you, and I’m grateful you gave this a shot, feel free to unsubscribe. I prefer a smaller group of rabid readers over a larger group of lukewarm casual readers.

Cross Pollinate between Notes and Essays

One interesting feature from Notes is you can highlight specific lines in a newsletter or essay and restack them like quote tweets.

The synergy is two-way. You can also cite Notes right inside the essay. The same note above looks like this:

Cross Pollinate between Comments and Notes

You can also restack (boy, the verb does sound clumsy) comments. Here’s the before.

Here’s the after.

I am leaning more into Substack and the Notes feature and see where this takes me.

Limited: Tag Person only Works on Web

Apparently, you can use @ to tag someone but only on the web version.

Unsolved: How to Restack Quote in Essay as Reply to a different Note?

I posted this as a question in Notes. Complete with a gif to demonstrate.

Prediction: Comments to be Merged under Notes

I’m going to start a Note going forward for every published essay and post it in the comments so that people will comment in the notes instead.

I have written several short essays here in Substack. Not all are sent out as email newsletters like this one because I don’t want to mail your inbox every time I have an idea.

Not all are equally well-formed or good. Some take more time to probe and sculpt. Having said that, I intend to send out a newsletter edition on the first and third Saturday of every month.

With that, I see you on the 6th of May.

As always, I wish you and your family good health and fortune.

Working Backwards, a book by former Amazon executives, cited Amazon founder Jeff Bezos’ 2016 shareholder letter

“most decisions should probably be made with somewhere around 70% of the information you wish you had. If you wait for 90%, in most cases, you’re probably being slow.

Bryar, Colin; Carr, Bill. Working Backwards (p. 71). St. Martin's Publishing Group. Kindle Edition.

I literally read this as don't wait to be perfect, move fast. I'm sure most people read it like that too.

But, now I see the more crucial line is actually in the following line of the same quote.

Plus, either way, you need to be good at quickly recognizing and correcting bad decisions. If you’re good at course correcting, being wrong may be less costly than you think, whereas being slow is going to be expensive for sure.”

Bryar, Colin; Carr, Bill. Working Backwards (p. 71). St. Martin's Publishing Group. Kindle Edition.

Emphasis is mine.

It's clear to me the key foundational skill is actually course correcting. It doesn't matter whether you move fast or slow, if your course correcting radar is wonky.

And Bezos quote gave the definition of course correcting:

1. quickly recognizing bad decisions

2. quickly correcting bad decisions

If you combine with execution speed you get the following list of outcomes:

1. NO course correcting + move fast => Fast-moving disaster

2. NO course correcting + move slow => Slow disaster

3. GOOD course correcting + move fast => Ideal

4. GOOD course correcting + move slow => Slow

Ideally, we want 3. But still better to settle for 4 than 1 and 2.

I write software and I sell the software I write. Writing and selling it taught me the importance of being a problem-solver.

One key thing I learn is: not all problems are equal.

Not knowing this fact cost me a lot of time and money in the past. Learn from my mistake.

Now, let's dive in.

Tier 1: Problem Solution are One

Alice: Give me water
You the problem solver: Give Alice water

This is the simplest tier. Just do as requested.

Tier 2: Problem and Solution 

Bob: I am thirsty
You: Give Bob water

Next simplest. Also the tier we mean when we say "problem-and-solution".

It's like hero-vs-villain.

Tier 3: Problem-Diagnosis-Solution: 

Charlie: My car won't start
Diagnosis: This is due to low battery water
You: Give Charlie (battery) water

Now we have three layers in this tier.

The problem presented is merely a symptom. You, the problem-solver, finds the root cause. Then, you provide the solution based on the diagnosis.

Situations like this are why techniques like 5 Whys are invented.

Tier 4: Problem-Diagnosis-Options-Direction-Solution 

Grace: We lack drinking water in this area
Diagnosis: Population has grown too fast
Options: Ration; Buy water; Desalinate
Direction: Adopt all 3 for short, medium, long term
Solution: Have portfolio of options to de-risk

At this tier, you tend to hear the word, "tradeoffs".

There are no easy solutions. Only hard choices.

Tier 5: Problem-Diagnosis-Options-Direction-Design-System: 

It's getting complicated, so let's continue with the last example of lacking drinking water.

We start from the same Direction.

...
Direction: Adopt all 3 for short, medium, long term
Design: This is the desalination plant design
System: The actual plant itself

This is where we need to get our hands dirty with building stuff.

It's also where some of humanity's greatest achievements lie.

Don't Apply Wrong Tier At the Wrong Time

Don't over-complicate when it's just a simple Tier-1 or Tier-2.

Also don't assume it's easy when it's more like a Tier-4 or Tier-5.

Choose wisely.

Balancing Experimenting and Assurance Needs

I have given a lot of thought about this whole “small bets” strategy. On the one hand, I am for it. This newsletter is a small bet for me, for example. Nobody really knows anything, so experimenting is the way out.

On the other, it’s hard to convince people to move to your small bet product if lives or livelihoods depend on it.

Killed By Google, a website that documents all the “small bets” that Google undertook over the years, is a great example of this strategy gone wild. Some of these products or services were much beloved and their demise irritated the hell out of users.

Other shutdowns have much worse impact. Imagine being a game developer spending months building games for Google Stadia, then having it get shutdown on you with no notice. How would you feel about it? Would you be comforted by Google telling you, “hey, no hard feelings. It’s just a small bet strategy.”

The Basecamp Exit Strategy: Maintain for existing customers but no new features or new customers

One way to square the circle is the Basecamp approach to phase out of past products. I like their approach.

Notice how they treat their existing customers in their past products. Here’s Highrise, Tada List, and Backpack. Just to name three. They all have the same exit strategy. It’s in the last line of every product description in their history.

Toys, Tools, And Trains Spectrum

The way I see it is there’s a spectrum across three categories of products. I call this the “toys, tools, and trains” spectrum. And by trains, I mean infrastructure.

The more that your product is depended upon, the more important you need to be reliable (and be seen as reliable). You can still be “small bets” and experiment, but you need a clear exit strategy like Basecamp where you take care of existing customers.

An exit strategy like that is admittedly more expensive than simply announcing the show’s over and chase everybody out. Don’t forget that infrastructure-like products usually command a greater premium and bargaining power over your customers when they’re successful.

Life, after all, is full of tradeoffs.

Do Hard Things Then Document in Detail

I recall a very old Ahrefs article about blogging that basically cover the same point as Arvid here. Couldn’t find it via Google, I’ll be grateful if anyone finds it. The steps to a good blog post (I’m recalling on memory) are basically:

1. Do something hard

2. Document the steps in details

That’s it. All the SEO techniques in the world are just amplifiers of these pre-requisites.

Any failure patterns that arise from following these steps are just some version of avoiding Dirty Work such as:

1. Avoiding the Dirty Work of doing something hard and documenting the steps in detail. So you focus on all the SEO/build-in-public tips and techniques.

2. Avoiding the Dirty Work of doing something hard. So you focus on picking something trendy to talk about instead.

3. Instead of picking something you’re deeply interested in albeit with narrow appeal and try to “do something hard” in it, you pick something with wide appeal (sexy) and try to “do something hard” in it.

Useful and Yet Not Too Functional

My entire revenue currently comes from writing software for businesses with at least 100 million annual revenue. And even then as a service, not product.

The people I tend to follow on Twitter who are also running their own businesses solo, are either:

1. they are more like content creators

2. even the software creators who are solo, they tend to focus on prosumer space and sell products

I have not been able to convert my existing business into a more product-oriented business, though not for lack of trying.

When I looked at the people I follow on Twitter who are good at their solopreneur businesses, I asked myself, “what’s the main difference between me and them?”

Initially, I thought the biggest difference is that they are good at marketing themselves and I’m not. Starting this newsletter is my attempt to get better at it.

Then, I came across this tweet by which cited an experiment by Substack that made me rethink perhaps the real difference between me and such solopreneurs is something else.

I want to highlight this part in the tweet.

Notice how Substack took two separate observations:

1. that $X.99 pricing shows poorer conversion rate than round-number pricing (e.g. $10.00)

2. and that some of their largest publications by ARR don’t even paywall any content or offer extra benefits to paid subscribers.

And explained both phenomena with, “perhaps pricing Substack subscriptions like one of the more function-based services made it feel more like a transactional purchase.”

It would have never occurred to me to ask people for money and not make sure that the people paying gets something extra. It doesn’t seem fair to them. Yet, it works.

Perhaps the deeper difference between me and the more successful solopreneurs I follow is I worry too much about the functional aspects of the exchange in value.

I do want to make money by being useful and I hope my customers get their money’s worth! But that made me too narrowly focused on making that happen.

People give money for all sorts of reasons and all kinds of value. And that obsession made me forget this simple fact.

I think too much in bright, straight lines and not enough in fuzzy, curved lines.

What are my options then?

In front of me are two paths I can see:

1. Either I change myself and practice being less rigid in my approach.

2. Or I change my area of focus and forget about emulating the solopreneurs I follow on Twitter. That is, double down in areas where the exchanges of value need to be straight and clear. Areas where my kind of rigid, straight-lined thinking are highly prized, rather than merely adequate.

I haven’t decided which path to take. But, this is certainly a new line of thinking that I never thought of until this counterintuitive experimental result by Substack.

Thank you for your subscription to my newsletter. And as always, I wish you and your family good health and good fortune.

Similarly, we need a term to describe people who start off being trained as engineers in their career.

These people are more than comfortable with technology — they actually build technology.

Subsequently, they transition to business. Either being a good managing executive or an entrepreneur.

I propose the term, "Native Engineer" to describe them.

What Are They Good At?

Native Engineers are comfortable with details and complexity.

If their engineering background is in the same industry their new business roles are in, they have a natural advantage.

They can think through the business implications of a technology decision and conversely, good at generating technology options to pursue their business strategy. Most of all, they can leverage the same background to make informed choices of which of the presented technology options to pursue for maximum chances of business success.

They don’t just see the forest; they also see the trees. And when necessary, go down to the weeds with the engineers as well.

Examples

Engineer-turned-executive: Satya Nadella, Microsoft’s third CEO in its history who started his career as an engineer at Sun Microsystems.

Engineer-turned-entrepreneur: Bill Gates, Microsoft’s co-founder and first CEO and its first chief software architect.

Does the Engineering Background be in Tech?

Not necessary.

Here’s Caroline Laurenson who started off as engineer in chemical engineering and turned entrepreneur in a different industry — smart home solutions.

She’s also a Native Engineer, by my count.

I took 3 weeks off in February to try that out and it was glorious. I met 3 customer deadlines while I was learning to snowboard in Japan. On top of that, I still had extra time to reflect on my lifestyle and my goals because you cannot really do too much in cold winter in a country where you don’t speak the language.

Learning to snowboard at my 4th attempt (I failed on 3 previous shorter trips) plus hitting some work output goals while still serving my end users and 99% of them not realizing my physical absence is mind-blowing. All the words in books like 4 Hour Work Week pale in comparison with one meaningful, real experience.

Long story short, I will heavily refactor my lifestyle moving forwards and that includes this newsletter as well. I haven’t settled on the details yet, but one thing for sure is, I’m not going to maintain a weekly cadence for its own sake.

I will have more to say about this trip and the reflections I got out of it in future updates.

One other thing I got out of this trip is I got more time to read carefully the books on my list. And one book that I really deep-dived into is Why Greatness Cannot Be Planned: The Myth of the Objective by Joel Lehman and Kenneth O. Stanley.

I've enjoyed literature that extolled the merits of real, detailed planning like the Peter Drucker’s Effective Executive and books on OKRs. However, at the back of my mind, there’s always something bugging me about such literature.

Why Greatness has been on my to-read list for a super long time, and I finally was able to take the time to read it. I regret not reading it sooner.

It elegantly and rigorously articulated that nagging feeling I’ve had all this while. Since I published my Dirty Work piece, I’ve been finding ways to practice what I preach.

I’ve always liked to hit multiple goals with a single move (the proverbial one stone killing n birds), since

• the snowboard February trip has influenced me to take a more deliberate, less frequent approach to my newsletter,

• I wanted to strengthen myself to have more stamina for Dirty Work,

• and I wanted to be more deliberate about integrating and practicing lessons from really good books I read into my life

my essay for this week is a highlights-and-commentary post on the first four chapters of the book.

Entrepreneurial Engineer

Notes on Objective Paradox Part I: Think In Search Space

I commented at Unknown Unknowns post "Niches get Stitches" recently, drawing parallels between the post and the Why Greatness Cannot be Planned book. As I kept adding more and more highlights from the book in the comment, I realized I would be better off writing standalone highlights-and-commentary posts instead…

Read more

3 years ago · KimSia Sim

Elsewhere on the internet

Vanishing into holes to reconfigure yourself as a person is highly underrated. My Feb snowboard trip was my personal vanishing hole.

Huge pockets of empty time where you exercise a great amount of autonomy is the new luxury item.

This echoes some of my own nascent thoughts about this newsletter. Given the rise of ChatGPT and similar tech, there will be more bland and generic content churned out.

Increasingly, differentiators like:

• Quality of the output (writing/video) in non-formulaic ways,

• hard-to-fake signals like receipts,

• tight fit between creator-topic-audience

are going to be even more so going forward.

Thank you for your subscription to my newsletter.

As always, I wish you and your family good health and good fortune.

I commented at post "Niches get Stitches" recently, drawing parallels between the post and the Why Greatness Cannot be Planned book.

As I kept adding more and more highlights from the book in the comment, I realized I would be better off writing standalone highlights-and-commentary posts instead.

Why This Matters For Entrepreneurial Engineers

Starting a new business initiative and keeping it running is hard.

The kind of hard that seems more like the difficulty of great accomplishments cited in the Why Greatness Cannot be Planned (henceforth known as Why Greatness) book.

And the authors of Why Greatness argue that setting ambitious objectives are counterproductive to achieving them.

Highlights with Commentary

Here are my highlights from the book’s first four chapters (total eleven). In total, I highlighted 28 snippets that stood out—along with some commentary.

1/ "This book was born from a radical idea about artificial intelligence (AI) that unexpectedly grew to be about much more.

…Usually these algorithms have explicit goals and objectives that they’re driven to achieve. But I began to realize that the algorithms could do amazing things even if they had no explicit objective—maybe even more amazing than the ones that did have an objective.

…I started to realize that the insight wasn’t just about algorithms, but also about life. And not just life, but culture, society, how we drive innovation, how we plan for achievement, our interpretation of biology—the list just kept expanding."

Joel Lehman is a machine learning research scientist. Kenneth Stanley leads a team at OpenAI as research science manager and even has his own wikipedia page.

Generalizing insights outside of the field they originate from can be dangerously sketchy. A classic example is the suspicious claims from New Age authors when they tried to extrapolate ideas from quantum physics.

The authors have great credentials as scientists, so they have a higher bar for what counts as true than your average person. Extrapolating AI concepts to general career planning would be the kind of sketchy generalizing I’m typically suspicious of.

But, I take scientifically trained people more seriously than laypeople. So I’m willing to give more benefit of the doubt.

2/ "A lot of effort and resources are spent measuring progress towards these objectives and others like them. There’s an assumption behind these pursuits that isn’t often stated but that few would think to question: We assume that any worthy social accomplishment is best achieved by first setting it as an objective and then pursuing it together with conviction.

…Everyday successes like these mislead us into believing that setting objectives works well for almost everything. But as objectives become more ambitious, reaching them becomes less promising—and that’s where the argument becomes most interesting. Some objectives are anything but certain."

The book’s thesis is that for highly ambitious achievements or those with high degree of uncertainty, setting them as objectives paradoxically decreases your chances of achieving it. An "objective paradox" if you will.

I will pair this book with Working Backwards: Insights, Stories, and Secrets from Inside Amazon by Colin Bryar and Bill Carr. Both are former Amazon executives who worked there in the early years. And their approach sounds, on the surface, the opposite of what Stanley and Lehman suggest here.

Since I started a Notes on Objective Paradox, I’ll also have to do a Notes on Working Backwards in future as well.

3/ "It’s useful to think of achievement as a process of discovery. We can think of painting a masterpiece as essentially discovering it within the set of all possible images. It’s as if we are searching through all the possibilities for the one we want, which we call our objective.

Of course, we’re not talking about search in the same casual sense in which you might search for a missing sock in the laundry machine. This type of search is more elevated, the kind an artist performs when exploring her creative whims. But the point is that the familiar concept of search can actually make sense of more lofty pursuits like art, science, or technology.

All of these pursuits can be viewed as searches for something of value. It could be new art, theories, or inventions. Or, at a more personal level, it might be the search for the right career."

Let’s assume that choosing an entrepreneurial path for your career or lifestyle is non-negotiable. Choosing the right specific entrepreneurial endeavor that meets your ambitions fits the kind of elevated search mentioned here.

Search Space, Stepping Stones, and Adjacent Possible

4/ "…we can think of creativity as a kind of search. But the analogy doesn’t have to stop there. If we’re searching for our objective, then we must be searching through something. We can call that something the search space—the set of all possible things.

…pretend you wanted to paint a beautiful landscape—so that’s your objective.

If you’re experienced in landscape painting, it means that you’ve visited the part of the room teeming with images of landscapes. From that location, you can branch off to new areas full of landscapes that are still unimagined.

But if you’re unfamiliar with landscape painting, unfortunately, you’re unlikely to create a masterpiece landscape even if that’s your objective. In a sense, the places we’ve visited, whether in our lives or just in our minds, are stepping stones to new ideas.

…stepping stones are portals to the next level of possibility. Before we get there, we have to find the stepping stones."

As a software engineer, the analogies of search space and stepping stones are familiar to me. I, too, have to search through a space of possible solutions when trying to solve difficult problems in the systems I build for customers.

As for the stepping stones analogy, it reminds me of the Adjacent Possible concept. Which I first learned from Steven Johnson’s book Where Good Ideas Come From: The Natural History of Innovation. Even though he took the concept from Stuart Kauffman who introduced it to explain how biological systems evolve into more complex systems “by making incremental, relatively less energy consuming changes in their make up”.

Put together, the idea is the adjacent possible are the stepping stones between what you currently know/possess and the remote possible you want to get to.

5/ "Objectives are well and good when they are sufficiently modest, but things get a lot more complicated when they’re more ambitious. In fact, objectives actually become obstacles towards more exciting achievements, like those involving discovery, creativity, invention, or innovation—or even achieving true happiness. In other words (and here is the paradox), the greatest achievements become less likely when they are made objectives.

…if the paradox is really true then the best way to achieve greatness, the truest path to “blue sky” discovery or to fulfill boundless ambition, is to have no objective at all."

I’m reusing the same 3 concentric circles from the previous commentary.

There are two kinds of objectives that are in the remote possible: those that you can conceive and those that you cannot. Regardless if they are conceivable, the path to them are highly uncertain. Because even after expanding your current sphere to include the original adjacent possible, your objective may still not be in the new adjacent possible.

In my model, the characteristics of any objective that fall under each of the 3 spheres are:

Current: any objective here is conceivable and definitely within grasp. Within grasp as in doable within your capabilities.

Adjacent Possible: any objective here is conceivable and theoretically but not definitely within grasp.

Remote Possible: any objective here may be conceivable or inconceivable, but definitely not within grasp.

6/ "Even after vacuum tubes were first discovered, no one would realize their application to computation for over 100 years. The problem is that the stepping stone does not resemble the final product. Vacuum tubes on their own just don’t make people think about computers. But strangely enough, as history would have it vacuum tubes are right next to computers in the great room of all possible inventions—once you’ve got vacuum tubes you’re very close to having computers, if only you could see the connection. The problem is, who would think of that in advance? The arrangement, or structure, of this search space is completely unpredictable.

…If you were like Charles Babbage in the 1820s and wanted to build a computer, you wouldn’t dedicate the rest of your life to refining vacuum tube technology."

The authors went on to cite more such examples of stepping stones and their more interesting counterparts throughout the history of great inventions. The point here is to bolster two separate ideas:

• in the sphere of remote possible there are inconceivable objectives the adjacent possible can lead to. This is the situation exemplified by the line, “Vacuum tubes on their own just don’t make people think about computers.”

• even if an objective in the remote possible is conceivable, the path to get there may be inconceivable because (some of) the intermediate steps themselves are also inconceivable. This is the situation exemplified by the line, “If you were like Charles Babbage in the 1820s and wanted to build a computer, you wouldn’t dedicate the rest of your life to refining vacuum tube technology.”

7/ "It often turns out that the measure of success—which tells us whether we are moving in the right direction—is deceptive because it’s blind to the true stepping stones that must be crossed. So it makes sense to question many of our efforts on this basis. But actually the implications are even more grave than just questioning particular pursuits and their objectives. At a deeper level, we might ask why we think ambitious pursuits should be driven by objectives at all."

8/ "As with all open-ended problems in life, the stepping stones are unknown. So when you go out into the uncertain world sometimes it may be wise to hitch a ride with serendipity. Being open and flexible to opportunity is sometimes more important than knowing what you’re trying to do.

…You might think these kinds of stories only apply to the luckiest of the lucky. But serendipity isn’t actually so picky. A peer-reviewed study found that nearly two thirds of adults attribute some aspect of their career choice to serendipity. As one participant put it, “I happened to visit an animal hospital and became interested in veterinary medicine.” You never know what hidden passion you might unexpectedly discover."

My best entrepreneurial result came about because I went to the birthday party of a secondary school classmate I haven’t seen in ages. On a whim. He subsequently introduced me to my highest revenue-generating customer of my career so far.

I’m sure many people in different domains can point to turning points in their careers that are similarly unplanned and serendipitous. The two thirds of adults attributing some aspect of career choice to serendipity1 is a number too big to dismiss.

9/ "As one large survey revealed, “actions such as volunteering, joining clubs and generally making contact with other people and groups are likely to increase a client’s chances of an unplanned experience2.” Note the emphasis on unplanned experience. This isn’t the usual attempt to figure out the best job and pursue it as an objective. It isn’t an impersonal test designed to categorize you into a particular box from a few multiple choice questions. Instead it suggests that you should embark on a search for possible stepping stones without any particular destination.

The beauty of this non-objective principle is that it’s not only about careers. It can apply to almost anything that involves searching for something, which covers an enormous range of activities. Because the stepping stones that lead to the greatest outcomes are unknown, not trying to find something can often lead to the most exciting discoveries (or self-discoveries). This same theme of finding without trying to find will emerge repeatedly throughout this book everywhere from computer simulations to educational systems."

That last paragraph about how the framing of going through search space applies to more than just career planning and AI is the biggest claim made from this book. It might be due to recall bias, or a bias towards novel, surprising experiences, but I’ve always found my best results often come from paths that are a little unplanned.

It’s not nice to admit that because that means I can never fully own my achievements. There’s always an element of luck involved. Either I get less rigorous with my intellectual honesty or I have to get over my ego. I’m choosing the latter.

10/ "While the idea that not looking can be the best way to find is strange and perhaps a bit zen, it does lurk already in some corners of our culture. As Loretta Young said, “Love isn’t something you find. Love is something that finds you.” As one of those great elusive objectives that almost all of us seek, it’s easy to relate to the deceptive search for love. But the funny thing is that almost any ambitious objective could be substituted for the word “love” in the wisest statements uttered on the topic. We just seem to have carved out this small niche, the search for love, where we acknowledge the paradox of ambitious objectives. As D.H. Lawrence put it, “Those that go searching for love, only manifest their own lovelessness. And the loveless never find love, only the loving find love. And they never have to seek for it3.”

…

For example, one day Grace Goodhue was watering flowers only to look up and see Calvin Coolidge in the window shaving with nothing on but underwear and a hat. Luckily for him, she laughed, catching his attention4. It’s unlikely that the future Ms. Coolidge ever targeted men who shave in their underwear, or that future President Coolidge ever thought his best moment would involve being caught almost naked. But then again, the unplanned is often the best plan of all. At least in the domain of romance, we all have some experience with the paradox of ambitious objectives. After all, what could be more ambitious than seeking lifelong happiness?"

11/ "Indeed, psychologists have noted that children need time to explore without specific tasks or objectives set for them by adults56]. Sometimes the term unstructured play is used to describe this kind of activity. Maybe adults need it too."

I’ve always liked learning. I have paid for a lot of online courses in the past and expect to do so into the future. I signed up for a 12-week long Dale Carnegie communication weekly workshop that will run from end January to April 2023.

I’m also literally writing this article in the middle of a trip in Japan to learn how to snowboard.

From the past, I have burnt out from being overly scheduled. Playing Tetris with my schedule did not make me more efficient. It made me more fragile. This snowboarding trip once again reminded me the importance of respecting my minimal requirement of "space" I need to actually acquire a skill. Another separate essay to cover in the future as well.

12/ "YouTube was first envisioned as a video dating site7. But when was the last time you found a date through YouTube? Its founders pivoted to video sharing, and the results speak for themselves.

…the photo sharing service Flickr was originally a smaller feature of a bigger social online game (that itself was inspired by playing an unrelated game about virtual pets)8.

… the (now) video-game company Nintendo also took a winding path to its success. Founded in 1889, for years Nintendo made a modest profit selling traditional Japanese playing cards. Later in the 1960s, as the playing card market collapsed, the company nearly went bankrupt trying out new business ventures like running a taxi service, building short-stay “love hotels,” manufacturing instant rice, and selling toys. The manager of the new toys and games division, Hiroshi Imanishi, hired a group of amateur weekend tinkerers to brainstorm products. When one of the tinkerers created an extendable mechanical toy hand, Hiroshi was impressed and released it as the “Ultra Hand.” The product’s huge commercial success prompted the company to abandon its non-toy ventures. Later Nintendo began to explore electronic toys, eventually leading it to become the iconic video game company behind “Super Mario Brothers9.”

If you take one thing from this chapter, perhaps it should be that you have the right to follow your passions."

I’m always a little bit suspicious of the "follow your passions" thesis. It sounds overly simplistic. There’s also the tendency to conflate passions with hedonistic pleasures.

But, I can certainly accept the idea that using what you’re interested in as a compass for going through a search space. Given that objective-based search isn’t as effective as it seems.

From a career point of view, some of your endeavors MUST pay off. If not immediately, at least eventually.

Nobody has a limitless budget to pursue their passions forever. Eventually, some of these searches need to pay off in order to fund more such searches. A virtuous career cycle for the perpetually curious.

13/ "If you take one thing from this chapter, perhaps it should be that you have the right to follow your passions. Even if they deviate from your original plans or conflict with your initial objective, the courage to change course is sometimes rewarded handsomely.

Another important implication is that not everything in life requires an objective justification. If you had a choice either to attend a prestigious law school or to join an art colony and chose the latter, your family and friends might have some questions: “Why did you give up such a lucrative career for something so uncertain? What are you trying to accomplish?” Instead of struggling to formulate some kind of objective justification that explains how you have the whole thing completely planned out, perhaps the best answer is that no one knows the stepping stones that lead to happiness. Yes, law school may reliably lead to money, but happiness (perhaps for you) is a more ambitious end, and something about that colony feels closer to it. Of course life is full of risk and some choices indeed won’t work out, but few achieve their dreams by ignoring that feeling of serendipity when it comes. You can simply tell your friends that you know a good stepping stone when you see one, even if (like everyone) you don’t know where it leads.

Whether you’re looking for a career, for love, or trying to start companies, there is ample evidence that sticking to objectives just isn’t part of the story in many of the biggest successes. Instead, in those successes there is a willingness to serve serendipity and to follow passions or whims to their logical conclusions."

The emphasis in this quote are all mine.

One thing I like to highlight is, even if the the idea "all the biggest achievements come from following your whims to their logical conclusions" is true, doing that in itself is NOT a guarantee of success.

But, for some of us, accumulating enough resources and capital (monetary and other kinds) can help make it easier to go after these passions. Especially those that are more challenging, with a lower certainty of payoff, or simply take longer to see results.

Another point to add is how some of the handsome rewards you read about other people serving their serendipity can lead you astray. High risks, high rewards games tend to attract gamblers.

I’ve made mistakes both ways.

I’ve made uninspiring (to me) career choices because they are easier to explain to the people around me. It takes a certain courage to tell people you “know a good stepping stone when you see one” especially when it’s not conventionally appealing. I’ve also made bad moves that seem more like a gambler’s desperation for big wins.

Keeping an open mind while listening to your heart is a tricky balance.

PicBreeder

14/ "In 2006, we had developed a new kind of artificial picture DNA that produced more rich, meaningful images (which you will soon see) than were possible before. But more importantly, this new project, which would become Picbreeder, included another ingredient that made it particularly interesting: Any internet user could continue breeding images that were bred by previous users.

… It turns out that after 20 generations or so (i.e. after choosing parents 20 times in a row), most people simply can’t continue concentrating. But evolution works best over many generations, and 20 isn’t enough to produce really interesting pictures.

… Make Picbreeder into an online service. That way, users could share images they had previously evolved with other users, who could then continue breeding them. In other words, if you evolved a triangle on Picbreeder, you could publish it to the website, and then someone else could continue breeding it and perhaps discover an airplane. In Picbreeder, this kind of handoff from one user to another is called branching. The great thing about branching is that it allows breeding to continue far beyond the 20-generation limit."

This is the research project that eventually led to this book being published.

15/ "Now here’s where the story gets interesting. Say, for example, that you’re in the mood to evolve a picture of the Eiffel Tower. One thing you might think is that if you visit Picbreeder and just keep choosing images to breed that look increasingly like your objective (the Eiffel Tower), eventually you’d find it. But interestingly, it doesn’t actually work that way. It turns out that it’s a bad idea to set out with the goal of evolving a specific image. In fact, once you find an image on Picbreeder, it’s often not even possible to evolve the same image again from scratch—even though we know it can be discovered!"

Reproducibility is an issue most of the self-improvement advice givers don’t realize.

Many times for credibility reasons, they cite their own (usually one-off) great achievements. But, they don’t realize that they may not be able to repeat them even though they now have experience from that one great achievement. What more for the rest of us who learn from their experience second-hand via their writings?

How useful are the general conclusions drawn from a small sample size of achievements?

16/ "We confirmed this paradoxical aspect of the system by running a powerful computer program for thousands of generations. First, we chose a target image from those that users have discovered and published on the site. Then, at every generation the program automatically chose parent pictures that look increasingly similar to the target image10. The result for the most interesting images—total failure. It’s impossible to breed an image if it’s set as an objective. The only time these images are being discovered is when they are not the objective. The users who find these images are invariably those who were not looking for them."

A limitation to the objective-based search. The next few highlights go into the specific reason for the limitation.

17/ "We expect an “A” student to know more about chemistry than one who is failing the class.

To borrow a term from computer science and optimization theory, this kind of measure is often called the objective function. Of course it’s no surprise that this term includes the word “objective” within it: It’s literally a method to measure progress towards the objective. So if we say that the objective function is improving, it means that our measure of progress suggests we’re moving closer to the objective. But here’s the problem: The idea that an improving score guarantees that you’re approaching the objective is wrong. It’s perfectly possible that moving closer to the goal actually does not increase the value of the objective function, even if the move brings us closer to the objective.

…Recall that the predecessor to the Car was the Alien Face. If our objective function for obtaining a picture like the Car is “how car-like is it?” then the Alien Face would be graded poorly because alien faces are definitively not cars. But the Alien Face in fact was the stepping stone to the Car, which shows you why always comparing where you are to where you want to be is potentially dangerous."

The Problem is Deceptive Stepping Stones

18/ "This situation, when the objective function is a false compass, is called deception, which is a fundamental problem in search. Because stepping stones that lead to the objective may not increase the score of the objective function, objectives can be deceptive.

… To make this idea more concrete, there’s a great example of this kind of deception called the Chinese finger trap.

… The deception of the Chinese finger trap is that the path to freedom is to push inward, away from freedom. In other words, the stepping stone to freedom is to become less free.

… The Chinese finger trap has only one deceptive stepping stone. There’s almost no question that ambitious problems like designing artificial intelligence or curing cancer will require well more than a single deceptive stepping stone. In fact, the search space of any complex problem is sure to be littered with deceptive stepping stones."

From a career perspective, making less money, earning less prestige, or simply having less immediate job security in order to free up more time or regain autonomy are all possible deceptive stepping stones towards actual wealth.

19/ "Consider for example the game of chess: There are many moves that seem promising (such as capturing a piece) that later actually lead to trouble because of subtle unforeseen implications. As tricky as that makes chess, the world we live in is far more complicated than even that, so deception is going to be everywhere. The moral is that we can’t expect to achieve anything great without overcoming some level of deception."

20/ "… any problem without deception is trivial, because the stepping stones to solve it would be obvious. Clearly that is not the case for our most ambitious objectives, because we have yet to solve them. That’s why deception is so universal.

… Deception is the key reason that objectives often don’t work to drive achievement. If the objective is deceptive, as it must be for most ambitious problems, then setting it and guiding our efforts by it offers little help in reaching it."

21/ "If we go back to Picbreeder for a moment, one of the most interesting things about it is that it has no final objective.

…There’s a better way to think of Picbreeder—as a stepping-stone collector. It collects stepping stones that create the potential to find even more stepping stones.

Collecting stepping stones isn’t like pursuing an objective because the stepping stones in the Picbreeder collection don’t lead to somewhere in particular. Rather, they are the road to everywhere. To arrive somewhere remarkable we must be willing to hold many paths open without knowing where they might lead. Picbreeder shows that such a system is possible."

Going after passions that have the potential to help you collect more passions is a more poetic way of what I wanted to say with my virtuous cycle diagram from earlier.

I recall how the late Kobe Bryant was first a basketball NBA champion and then an Oscar winner for best animated short film. Definitely a lot easier to get movie people taking your calls about making a short film when you’re leveraging your status as a celebrity NBA champion.

Another way Kobe Bryant leveraged his past achievements into the award winning film is that the film itself is about his love for basketball. So, it talks about a topic he was intimately familiar with.

22/ "Let’s try a thought experiment to see what happens when objective thinking is applied to natural evolution.

…Your objective is to evolve organisms with human-level intelligence by selecting which organisms should reproduce. The basic idea is to replace natural selection with your own decisions about who gets to reproduce. For example, if you happen to spot what looks like the Einstein of amoebas, you can select it to reproduce and make more amoebas like it.

… The great thing about this experiment is that we know it’s possible because those very single-celled organisms did evolve over billions of years into human beings.

… So what should be your strategy to breed single-celled organisms all the way to human-level intelligence? We’d like to suggest a clear-headed approach that gets right to the heart of the matter: You can administer intelligence tests to the single-celled organisms! Then all you need to do is pick the ones that score highest to be the parents of the next generation. Soon enough, we’re on our way to a real Einstein, right?

… The problem is that the stepping stones to intelligence do not resemble intelligence at all. Put another way, human-level intelligence is a deceptive objective for evolution.

… subjecting a cell to an IQ test (or any intelligence test) is unquestionably ridiculous. But the fact that it is ridiculous is exactly the point, and is why this experiment should ring alarm bells for anyone who still believes in the myth of the objective."

23/ "Like Picbreeder, evolution in nature is a stepping-stone collector. These stepping stones are collected not because they may lead to some far off primary objective, some ultimate uber-organism towards which all of life is directed, but because they are well-adapted in their own right."

“Well-adapted in their own right” is a great criteria for selecting which passions to pursue and maintain. Either they are low in costs or they are at the very least self-sustaining. The moment they are self-sustaining, then you basically have near unlimited runway for any one of them to break out.

Psychologically, I also found that doing things in an autotelic sense, is crucial for keeping the passion “pure”. It needs to be pursued for its own sake. Not just because it may one day turn into something lucrative.

Minimum Criterion and Other Constraints

24/ "… it’s common to believe that evolution does have an objective, which is to survive and reproduce.

… how often is the product of an objective-driven effort not the objective? Birds are a product of evolution but birds were not the objective. Nowhere in survive and reproduce does it say anything about birds. Would any entrepreneur start a company with the sole objective of creating a product that lasts a long time?

… Usually, the objective is a well-defined product that you ultimately do produce if you are successful, not a nebulous generality.

… Usually, when we formulate an ambitious objective, we haven’t already achieved the very objective that we’re setting. setting. That would be a rather odd way to start. What kind of strange marathon is over exactly when it begins? But that is precisely how survive and reproduce works: Clearly the very first organism on Earth survived and reproduced, or we wouldn’t be here. Not only that, but then so did every other organism from the very beginning in the direct chain through the tree of life that leads to us.

… Is that really objective-driven discovery in the traditional sense?"

For the authors, that they have a highly precise definition of the word, “objective”. It cannot be some “nebulous generality”. It refers to a well-defined, specific, and concrete outcome. And it clearly can only be achieved at the end of the endeavor.

The rigor displayed in this thinking impressed me. No wonder the authors are scientists. This is the level of rigor I want to emulate in both my work and my writing.

25/ "Perhaps survive and reproduce can be more naturally seen as a constraint on evolution. In other words, it’s a kind of minimal criterion that all creatures must satisfy to continue evolving. But it describes nothing about the products that might be created, nothing about the difference between where we are today and where we might be tomorrow, and nothing about the potential for greatness lurking behind it. And by viewing survival in nature as a constraint rather than as an objective we no longer have to bend words in unnatural ways."

The authors took “survive and reproduce” and flipped it from an objective of evolution to being a constraint on evolution.

This makes me think how many of the “goals” I set out for my own one person software business such as revenue levels are perhaps framed incorrectly. They should have been treated as “constraints” instead.

26/ "Almost no prerequisite to any major invention was invented with that invention in mind.

… Great invention is defined by the realization that the prerequisites are in place, laid before us by predecessors with entirely unrelated ambitions, just waiting to be combined and enhanced. The flash of insight is seeing the bridge to the next stepping stone by building from the old ones."

27/ "Even if your goals aren’t particularly noble, you can’t avoid the problem of deception. Maybe you just want to become rich. But as we saw from the personal stories in the last chapter, measuring success against the objective is likely to lead you on the wrong path in all sorts of situations. Deception applies to becoming rich just as everywhere else."

I know a childhood friend did a bunch of career changes on his way to running a million dollar business. Ranging from being a regular in the military to being regional sales for a German manufacturing company to now running his own interior design agency. He didn’t even make some of these choices out of passion. Sometimes, it was the very thing that he could make a living in.

I recall he had an extremely rough first 18 months in his interior design agency business. He quit his lucrative regional sales manager role to pursue this only because the sales manager role required him to travel a lot and he wanted to be more available for his elderly parents.

Deception is very real even for highly mundane goals like getting rich and doing well in career.

28/ "We should be concerned by the disconnect between how the world is supposed to work and the way it really does work. When we set out to achieve our dreams, we’re supposed to know what our dreams are, and to strive for them with passion and commitment. But this philosophy leads to absurdities if taken literally. You can’t evolve intelligence in a Petri dish based on measuring intelligence. You can’t build a computer simply through determination and intellect—you need the stepping stones. You can’t become rich simply by seeking a higher salary—getting a raise today doesn’t guarantee another raise will ever come in the future. There’s much we cannot achieve by trying to achieve it."

I will do a Part II on the Notes on Objective Paradox in future. So stay tuned.

Entrepreneurial Engineer

What is "Dirty Work"?

As an engineer, I am biased to the idea is about solving highly rewarding, hard problems. StaySaaSy highlighted that the best hard problems are only one of two types: Technically Difficult problems are where buyers of the solution are not clear if they can solve it on their own even with a lot of time and money…

Read more

3 years ago · KimSia Sim

This week’s post has been several years in the making. It all started a few years ago when I solved a seemingly impossible problem for a customer by performing trial and error over 5 hours. The result felt like magic.

A few years later, did I begin to understand that I had channeled something I would describe as “embracing Dirty Work”.

Dirty Work is painful work that people avoid that’s necessary for growth, produces seemingly magical results, and is opposite to the kind of Technically Difficult work that’s catnip to engineers.

What helped me to come up with this term was that I discovered posts from different people talking about a similar phenomenon of embracing Dirty Work to solve Really Dirty problems in different domains.

They don’t all use the same name for it. Nor do they use the exact same description. But, they overlap enough of it. And now, I feel ready to share a rational definition of Dirty Work which is why I wrote this post.

Second, avoiding Dirty Work is, in my opinion, the most common blocker for anyone looking for breakthroughs in their career or business. Why? Because avoiding pain is deeply human. Hopefully, my writing about Dirty Work can help more people to get unstuck in their businesses and careers.

Finally, I wrote this because embracing Dirty Work is hard. Super hard. By writing this, I hope to practice more what I preach.

I expect to write more Dirty Work related pieces in the near future.

Elsewhere on the internet

Since I am on the topic of encouraging people to embrace Dirty Work, here’s something that’s the complete opposite — people repeating Very Hard Work unnecessarily.

These two tweets are part of a conversation prompted by a zoom call I had with Rob Fitzpatrick. He told me about how Amy Hoy mentioned the tendency of some people who spent a lot of time to build a product from $0 to $1k, then promptly stopped growing that, and repeat the whole process to build a separate new product.

I find that story totally unbelievable.

I had a hard time growing my one-person software service business to my current stage and I still hadn’t figured out how to have a product business.

So, to hear that there are people who rather start from $0 repeatedly despite getting to $1k each time meant I had to ask Amy about it. Which led to the conversation above.

I Learned About "Process Strategy"

I was reading newsletter this week and learned a new term I have never heard before: process strategy.

Several years ago I watched a good cook making a luxury of ratatouille. Though there are ratatouille recipes, the dish in original form is a process strategy not a recipe: A combination of aubergines, courgettes, peppers, tomatoes, and onions, each cooked to different levels of softness and caramelization.

The Uncertainty Mindset

2804m above sea level

Hello friends, Newsletter evolution update: This issue comes two weeks after the last one — which feels closer to the right tempo. Read on for some noodling on stuff at the beginning (somatic tacit knowledge, not-knowing, discomfort, snowboarding, conversations), and links to writing at the end (about imaginary ethnography, ratatouille as process strateg…

Read more

3 years ago · 4 likes · 13 comments · Vaughn Tan

I googled to learn its definition and it’s apparently an operations management term. Since operations management is concerned about “the set of activities that creates value in the form of goods and services by transforming inputs into outputs”, that naturally appeals to the engineer in me.

Engineers like to think in terms of transforming inputs into outputs.

When I asked more about "process strategy" in the comments , I got an analogy a software developer would love.

I’m still a bit unsure what “process strategy” means, but I expect to use it in my writing in the near future since I write for entrepreneurial engineers.

Thank you for your subscription to my newsletter.

As always, I wish you and your family good health and good fortune.

1. Technically Difficult problems are where buyers of the solution are not clear if they can solve it on their own even with a lot of time and money

2. Really Dirty problems are where it’s solvable but takes a lot of unpleasant work

Dirty Work is the work you have to do to solve that Really Dirty problem.

This post on Dirty Work is not just words and concepts. My first experience of Dirty Work was visceral and accidental.

I once solved a seemingly impossible problem for a customer by performing trial and error over 5 hours. The result felt like magic.

At that moment, I had accidentally embraced Dirty Work without knowing what I had done. Only many months later, did I begin to understand this thing called Dirty Work.

So, I turned that magical experience into a touchstone memory, a felt sense of what embracing Dirty Work meant. I had hoped that intuitive understanding was enough for me to develop a taste for Dirty Work and perform it reliably.

It wasn’t enough.

Dirty Work, by definition, is off-putting. Nobody would willingly subject themselves to unpleasant stuff. Even when there’s a promise of better things to come after enduring the unpleasant stuff.

In my pursuit to make myself embrace Dirty Work more reliably, I found I also needed a more rational definition. At the very least, a 101-style introduction to ground the intuitive understanding and to communicate with others this understanding.

This is that rational definition I’ve always wanted to write.

So, what is Dirty Work?

1. Defining Dirty Work

   1. Painful

   2. Necessary for Growth and Big Career Rewards

   3. Results That Appear Magical

   4. Opposite of Technically Difficult

2. What if I Hate Dirty Work?

   1. Realize: Good Solution is More Than Code

   2. Realize: Effectiveness First, Then Efficiency

3. A Bullet Point Summary

Defining Dirty Work

As mentioned at the top, Dirty Work is work to solve Really Dirty problems. But, I want to be more precise.

To do that, I drew on my own experience and from the writings of three different experts in three different domain. They are

1. the people behind the StaySaaSy blog (which is a guide on scaling product & engineering teams from $0 to past $100M ARR by people with that experience),

2. Paul Graham of Y Combinator fame (who writes about his experience in startups),

3. and Jacob Kaplan-Moss (who writes on software engineering).

These are the key articles I base this post on:

1. StaySaaSy in Build Your Career on Dirty Work and Enterprise Retention Means Solving Hard Problems

2. Paul Graham in Schlep Blindness

3. Jacob Kaplan-Moss in Embrace the Grind

From the study of all that material, I believe Dirty Work has four characteristics:

1. is painful, and to the extent you have little competition for it,

2. is necessary for growth such as to unlock certain career or business opportunities,

3. produces results that look magical to other people,

4. and is the opposite of a Technically Difficult solution i.e. it has almost no pre-requisites other than a willingness to get hands dirty.

I derived all 4 points from the 3 sources I cited earlier.

Painful

Pain is cited by all 3 sources.

StaySaaSy called it “lamentable work that many people avoid”.

Jacob described it as “terrifically tedious”.

Paul Graham said it’s unpleasant and to handle it “the same way you'd deal with a cold swimming pool: just jump in”.

StaySaaSy also pointed out that one implication of the high unpleasantness means competition is low:

the more unsexy the work is, the less likely it is that a lot of really great people have taken a crack at solving it. In short, there’s likely to be low hanging fruit.

— from Build Your Career on Dirty Work

Necessary for Growth and Big Career Rewards

Since most people over-index on the pain and thus avoid it, there’s a danger you can go in the opposite direction and assume all pain is good.

Which is why it’s important to recognize that Dirty Work must be absolutely necessary for growth. must be good pay-offs.

Here is Paul Graham on how necessary and inevitable Dirty Work is when building a company and not endorsing indiscriminate pain. In the same paragraph where he compared Dirty Work with cold swimming pool, he warned:

There was a point in 1995 when I was still trying to convince myself I could start a company by just writing code. But I soon learned from experience that schleps are not merely inevitable, but pretty much what business consists of. A company is defined by the schleps it will undertake. And schleps should be dealt with the same way you'd deal with a cold swimming pool: just jump in. Which is not to say you should seek out unpleasant work per se, but that you should never shrink from it if it's on the path to something great.

In case you are easily fooled by any one asking you to join their venture because they promise a lot of pain, StaySaaSy has a really good tip. Start by joining a growth company, then look for Dirty Work in it:

find a growth company, one that really needs you to get work done, and then tackle the unpleasant work that everyone avoids. I think this is a broadly applicable path

Both StaySaaSy and Paul also cited Stripe, a billion dollar startup, as a prime example of being handsomely rewarded when going after the Dirty Work of solving payments infrastructure as a purely business idea.

Results That Appear Magical

It’s not just at the career-direction level that embracing Dirty Work can have a huge impact. At the day-to-day work level, embracing Dirty Work can make your peers look at your results with awe.

Jacob in Embrace the Grind citing the words of Penn of the magician duo Penn and Teller from the article Seven Secrets of Magic:

You will be fooled by a trick if it involves more time, money and practice than you (or any other sane onlooker) would be willing to invest.

And the full quote was a story where Penn and Teller did a magic trick on the David Letterman Show that involved tedious amount of work which included hiring an entomologist to provide hundreds of “slow-moving, camera-friendly cockroaches”.

At the end of the story-quote, Penn ended with:

More trouble than the trick was worth? To you, probably. But not to magicians.

Jacob continued this same line of argument by pointing out:

I often have people newer to the tech industry ask me for secrets to success. There aren’t many, really, but this secret — being willing to do something so terrifically tedious that it appears to be magic — works in tech too.

He even included an actual real-life example.

For example, I once joined a team maintaining a system that was drowning in bugs. There were something like two thousand open bug reports. Nothing was tagged, categorized, or prioritized.

And drew parallels with real stage magicians and their embrace of tedium in service of a great performance.

So I used the same trick as the magician, which is no trick at all: I did the work. I printed out all the issues - one page of paper for each issue. I read each page. I took over a huge room and started making piles on the floor. I wrote tags on sticky notes and stuck them to piles. I shuffled pages from one stack to another. I wrote ticket numbers on whiteboards in long columns; I imagined I was Ben Affleck in The Accountant. I spent almost three weeks in that room, and emerged with every bug report reviewed, tagged, categorized, and prioritized.

Opposite of Technically Difficult

Since Dirty Work is work to solve a Really Dirty problem, logically, the key is to first find a Really Dirty problem.

But, engineers have a unique issue. They are unbelievably attracted to Technically Difficult problems. Like kids to candy.

The attraction to Technically Difficult is so deep in engineers, there’s a good chance that when faced with a Really Dirty problem or even a simple problem, engineers will over-complicate and choose to implement a Technically Difficult solution.

Engineers know what I’m talking about. :)

Which is why casting Dirty Work as the opposite of Technically Difficult is useful.

As an engineer, I found it easier to identify what’s Technically Difficult and then choose the opposite.

Which is why, personally, I find this contrast very useful in my one-person software business.

What if I Hate Dirty Work?

I write primarily for entrepreneurial engineers so, if you’re a developer, I’m not surprised if you’re allergic to the term, “Dirty Work”.

Paul Graham pointed out that, “No one likes schleps, but hackers especially dislike them.”

Jacob writes for developers so he attempted to address this aversion. In his attempt, he cited Larry Wall’s virtues of the programmer, which included laziness in his post. Jacob, for all the goodness in his post, didn’t address this objection as well as I thought.

I will follow Jacob’s example and assume that any objection towards Dirty Work cite Wall’s “laziness is a virtue” as the main argument.

My preferred response to this argument is to point out two things:

1. Larry Wall’s “laziness is a virtue” is strictly about writing code and a good, real-world solution is often more than just code.

2. “Laziness is a virtue” makes better sense in building business and product when phrased as an emphasis on efficiency. But, efficiency is never the first priority when trying to solve a hard problem.

Let me dive deeper into both points.

Realize: Good Solution is More Than Code

Since Larry Wall restricted laziness purely to the activity of writing code, this instantly weakened the argument of laziness as a virtue for any serious engineer.

First, building a successful software business or product involves lots of unavoidable Dirty Work because it’s more than just writing code.

Paul Graham, speaking from experience at Y combinator, saw how many developers often want to build businesses simply by writing code.

Most hackers who start startups wish they could do it by just writing some clever software, putting it on a server somewhere, and watching the money roll in—without ever having to talk to users, or negotiate with other companies, or deal with other people's broken code. Maybe that's possible, but I haven't seen it.

One of the many things we do at Y Combinator is teach hackers about the inevitability of schleps. No, you can't start a startup by just writing code.

Second, even in a pure software engineering role, writing code is only a small part of it. Real engineers have to perform tasks such as documentation, requirements gathering, and doing maintenance tasks.

Avoiding, or doing poorly on these important, necessary tasks (remember, one key definition of Dirty Work is it’s supposed to be necessary for growth) means your career will be severely limited.

Your senior management will be reluctant to give you more responsibilities if you cannot be bothered to do routine, maintenance tasks well. Fewer responsibilities mean fewer rewards.

Realize: Effectiveness First, Then Efficiency

Even if I were to steelman Larry Wall's “laziness is a virtue” as an ode to efficiency, that doesn’t fundamentally go against Dirty Work ethos because there’s nothing worse than efficiently doing the wrong things.

And there’s a time and place for efficiency as StaySaaSy explained:

do not, in any circumstances, normalize the pain you’ve accepted. You must fight tenaciously to fix the issue. Embrace the dirty work, and then be the leader who solves it comprehensively and scalably.

Notice how there’s a sequence in StaySaaSy’s description. First, effectiveness via Dirty Work. Second, efficiency through scaling. There’s no conflict between wanting efficiency and actually solving real, hard problems.

In other words, Larry Wall’s argument for “laziness” is valid in isolation but not so in the context of finding effective solutions to hard challenges in product and business.

A Bullet Point Summary

To summarize, for engineers who like solving hard problems, there are only two kinds of good, hard problems: Technically Difficult, and Really Dirty.

Engineers often over-index on Technically Difficult problems which may not be solvable even with great resources and under-index Really Dirty problems which are solvable with unappealing work.

Dirty Work is that unappealing work needed to solve Really Dirty problems and this means it has four characteristics:

1. it’s painful,

2. it’s necessary for growth,

3. it produces results that appear magical,

4. and is the opposite of a Technically Difficult solution.

Any resistance towards Dirty Work is understandable and perfectly human. But, using arguments such as Larry Wall’s “laziness is a virtue” to justify the ill-feeling is not valid when building software products and businesses.

Building software products and businesses entails more than just writing code. “Laziness” has its place in business but only in the lens of efficiency. When an absolutely necessary and effective solution to a real, hairy problem is required, laziness becomes an actively harmful trait.

The Model as Diagram

My own summary of the model is:

1. There’s no simple linear relationship between the key factors that affect your outcome.

2. The factors are interdependent rather than independent. As exemplified by each of the 5 factors all having two-way relationships with every other factor

3. The factors as a collective is also not independent. They are enveloped within a larger context such as biology, physiology, and environment.

4. The larger context itself has multiple layers where biology & physiology is one layer and environment is another layer.

Tipping Tray Analogy

Given that there’s no simple linear relationship, trying to initiate change isn’t straight-forward or one-size-fits-all either.

The paper provided this tipping tray analogy in diagram form as well.

My own summary of the analogy is:

1. Given that none of the marbles are clearly labelled, it means there’s no fixed order to start with which of your key factors.

2. Starting with a single-domain intervention is easier than multi-domain intervention. But at the same time, a single-domain intervention might not be enough to induce permanent change and more likely to allow relapse.

3. Trying, successful intervention, and actual permanent change are separately different situations. A single-domain intervention that doesn’t lead to change is unsuccessful trying. A multi-domain intervention that works but yet to stabilize isn’t permanent change.

How This Applies to Entrepreneurial Engineers

I have often read that a software system is a socio-technical system.

Whether you’re building a custom, enterprise system, or selling a small, consumer-oriented app, if/when your products become successful, inevitably you must have executed the social aspects brilliantly.

When Applied to the Software You Build

You cannot simply throw a user manual and some marketing copy and expect your users, and customers to adopt your system enthusiastically without any objections.

And I’m not just talking about sales and distribution. Which is how you get initial awareness for the system you’re building.

I’m also talking about habits and long-lived business processes. Because when your system meshes well with existing habits or processes, or induces new habits or processes, then your system becomes "sticky", or using the words of Synergistic Change Model, "stable and permanent change".

This means you need to try multi-domain intervention for your software system to stick with customers and stay sticky going forward.

This is not easy because:

1. the factors are multiple,

2. they interact with one another in non-linear fashion, and therefore

3. no clear one-size-fits-all method that works for all situations and all stages of growth.

But, you’re an entrepreneurial engineer. You have no choice but to figure it out.

In the case of building more successful software systems, do bear in mind, you have to figure out what the specific domains are. The 5 domains in Synergistic Change Model are perhaps only meant for behavioral change.

Who knows, maybe there’s more than 5 when it comes to building successful software systems. I don’t have a clue myself what the specific domains are for building software, though I can hazard a guess.

But, what feels certain based on my experience building and selling software to businesses (successfully and unsuccessfully) and individuals (unsuccessfully) is this general pattern of the Synergistic Change Model with the multiple domains wrapped in multi-layer context suggesting multi-domain interventions is on the money.

Maybe I should develop it further and call it the Software Adoption via Synergistic Change Model.

When Applied Internally With Regards to Your Person

And of course, since the original model is meant for behavioral change, it’s good for changing yourself as a person.

Maybe you need to change mindsets, skillsets, and toolsets in order to become the kind of entrepreneurial engineer more likely to make successful software products.

In this aspect, you can apply the Synergistic Change Model as is. And this is clearly the more direct application of the Synergistic Change Model for entrepreneurial engineers.

Today’s newsletter is not a goals for 2023. Nor is it a review of last year.

It’s more of an announcement of upcoming experiments for this newsletter that I want to try until at least April 2023. And a brief explanation of these changes.

If these changes are not what you’ve signed up for, you may unsubscribe at the bottom. I turned off all unsubscribe notifications so no hard feelings.

Focus More on One Person Software Business

I’m a fan of piece Becoming a Full-Time Creator as a Software Engineer: Controversial Advice . In it, he explicitly says, "Instead of creator, think one-person business".

I like this phrasing of a "one person business". And given my disposition as the engineer with entrepreneurial ambitions, it makes even more sense to narrow that phrase down further as one-person software business.

What I have written so far has been wide-ranging.

From the one about learning new skills while respecting your unique disposition in that piece about playing chess with Yoda to the one about renaming the Serenity Prayer as Wisdom Protocol, I see them as all connected to my current life and goal of building a software business.

Content-wise, there’s no change.

Therefore, the change I’m making is that I’ll be making the connections between my usual content and running a one person software business more explicit going forward.

Over 36 months of a Ramen Profitable, One Person Software Business

Another reason I want to concentrate more in the One Person Software Business topic is because I have now reached 3 years of running a Ramen Profitable, One Person Software Business. I consider a business to be Ramen Profitable when monthly revenue has a minimum of 5k USD for at least 6 consecutive months. I’m currently around 7.5k for the monthly revenue.

Come April 2023, that monthly revenue will either go to zero, or above 10k.

While my memory is still fresh at this stage, I thought sharing my experience at this stage might be helpful to somebody who’s about 2 to 10 years behind me.

Newsletter != Post

The past 12 issues or so, the post and the newsletter are one and the same.

The second change I’m making is to explore a format where I will write the newsletter as a synopsis to the post of the week.

In other words, I’m decoupling the newsletter from my posts.

During the past month of hiatus, I actually haven’t stopped writing. I posted on Substack but without sending out email notifications.

Right now, on the homepage you can find pieces I have posted recently but none of them were sent out as email newsletter.

I have seen the newsletter as synopsis to the post of the week style work for Commoncog Newsletter.

It’s quite obvious that the most popular pieces have been sent as email newsletter. I have some apprehension about decoupling the posts from the newsletter.

On the other hand, newsletter encourages an aggregation of interesting links I see from elsewhere on the internet. I like that format in my newsletter, but not so much for long form posts I prefer to be standalone.

My choices boil down to:

1. Write long-form posts and send them out as newsletter as well as those regular newsletter with an aggregate of content from all over the internet. Con: Newsletter frequency is higher and format consistency is compromised.

2. Write long-form posts and include other unrelated content and send out as newsletter. This is the current approach. Con: no standalone long-form posts and the long-form cannot exceed 2,000 words due to email’s limits.

3. Write long-form posts. Don’t send them out as newsletter. Write newsletter that links to the post of the week. Con: the standalone long-form posts may not be as popular as regular newsletter posts.

I am choosing to go with the 3rd choice as a compromise.

I don’t like the idea of bombarding your mail inbox with a frequency higher than weekly. And I surmise not everybody finds my long-form posts equally interesting. I leave it to the individual reader’s choice to see if they want to delve deeper into the long-form posts.

Have a Writing Budget for 2023

I intend to write between 20 and 30 Post of the Week for the whole of 2023. I am still undecided whether I will allocate some of these 20 to 30 Post of the Week to a separate newsletter dedicated to my side project — GreenDeploy.io.

Writing 20 to 30 Post of the Week isn’t just a goal. It’s also a budget for allocating time and energy towards writing.

Building up a media outlet for my own career or business is important for this internet age. Which is why I’m creating a budget for this activity like a business creates budget for resources to put into its projects.

As Orosz puts it in his creator economy piece,

A much better model for the "sustainable creator" is creating on the side of the one-person business. Basically, focus most of your energy running your business which makes money, and create some related content to this business.

I don’t expect to make money from all these media related activities (I’m also exploring YouTube and Shorts) anytime soon. And I see participating in media as an important strategy in my actual one person software business.

The Writing Must Be for Its Own Sake Too

A few years ago, writing content related to the business without trying to make money on the content directly would have been called content marketing. But, the typical examples I have seen sound more like brands than actual persons.

Before ChatGPT and similar tech took off, I was already hesitant about this kind of writing. Now these AI tools are getting popular, I have even less wish to sound machine-replicable.

Despite that fear, I also want this media outlet to be good for my career/business, I don’t want my writing to be too instrumental or transactional. People can tell you’re just doing a shift, and I won’t enjoy it for long either.

On the other hand, not treating this newsletter seriously like a business is counter-productive. I have no wish to be a starving artist either.

In other words, I want to avoid the two typical failure modes:

1. Be too transactional and instrumental for purely business reasons → the path is too painful for me and the content becomes too artificial in tone

2. Be too self-centered for purely emotional reasons → the path bears no fruit and the writing is too self-indulgent in tone

Both the goal (have this help my career and business) and the path (creating this newsletter) must make sense. Both must be effective, considerate, and enjoyable.

I’m trying to figure out that right sense of balance between the two. Which is why I’m trying out these experiments from now till April 2023 at least.

You’ll get back to the regularly scheduled newsletter with these new changes on 21st January 2023 Saturday.

I’ll see you next week!