Rapid Skill Acquisition: How To Learn Faster

Introduction

This guide has 2 aims:

How to acquire new skills most quickly and effectively
Systematizing skill acquisition and skill stacking

But, to me, these are both means to an end. The ultimate goal of this guide, and why I care about skill acquisition, is to maximize our time on this earth.

The acquisition of skills lets us enjoy progress. This is a great feeling.

At the same time, as we develop our skills, we can take on harder problems and make greater contributions to the world. Another great feeling.

Skills also serve as a safety net. Regardless of what happens to you (financially), you retain hard-earned skills. They may atrophy with disuse or aging but are quickly regained. They allow you to get back on your feet. And nobody can take them away from you. You can take them with you wherever you go.

But the best thing about skill acquisition (and stacking) is that it lets you fail forward. The project or endeavour you undertake may fail. But the earned skill raises your foundation on which you start your next one. This opens up new games, lets you play them more quickly and increases your odds of success. Success within this smaller game but also success within the biggest game: life.

With every new skill you try to acquire, you invite more serendipity. Serendipity eventually leads to success in life. This, in my eyes, means finding your purpose (or destiny), then applying yourself to its full realization until your final breath.

Earl Nightingale said it well: “Success is the progressive realization of a worthy ideal.”

I write this guide for my sake. I wanted an easy-to-follow process to rapid skill acquisition and a skill stacking system that invites serendipity and allows the progressive realization of my worthy ideal.

I wanted a system I could live – and enables daily progress – for the rest of my life.

This guide outlines this system as I’m living it now. I wrote it for my sake but I hope it helps you uncover and progressively realize your own worthy ideal, too.

Jim

Getting started

The foundation on which I’ve built my system: skills are learnt by applying knowledge. Knowledge is thus a means to an end.

Knowledge acquisition is a dangerous slippery slope. Reading, studying and researching is very comfortable. There’s a constant sense of progress and it’s impossible to fail.

Contrast that with applying and doing. Failure is the default, especially at first. It’s discouraging. Every failure mounts on the previous one and makes you question yourself increasingly more. You start to wonder if you’re making any progress at all.

Knowledge acquisition is like sleeping in a warm, comfortable bed. Skill acquisition is like not having a bed at all – you have to find it every single day.

Knowledge is useful. But it’s free. Anyone can acquire it. And it becomes increasingly accessible as technology advances.

Nor does it invite serendipity. It only gives you the illusion of inviting serendipity.

It makes you aware of possibilities. Of new experience. But it doesn’t let you experience it first-hand. As a result, success never gets any closer.

Knowledge is a means to an end. It’s a building block. It lays the foundation on which you acquire something more useful and with greater leverage: a skill.

As you progress your input-to-output ratio should change.

The goal should always be skill acquisition, not knowledge acquisition.

Knowledge acquisition

1. Newbie

When you start out in any field, you know nothing. Do a quick search and use reviews to find 1~2 well-regarded books. Read those to gauge your interest and decide if this field or skill is worth diving more deeply into.

You can complete this phase in 1 day to 1 week.

2. Beginner

You’ve gone from newbie to beginner. At this stage I recommend:

Community. Join 1 community with experienced people in your selected field and ask them for suggestions on what to do/read and what not to do/read – to acquire your selected skill rapidly. Shortcut your journey by learning from the lessons of others. But always ensure these others are practitioners, not readers.
Study great practitioners. Identify 1~3 historically great practitioners/experts and study them. You can learn from anyone but studying the best accelerates your progress as they have more experience and battle-tested lessons to share.
- Optional: identify 1~3 overachieving underdogs: those who nobody expected to achieve such a high level in this field/skill. Why? These people more likely got to this level via a replicable training methodology and less via innate talent.
Great books. Read 3~5 great books on your topic. Use the wisdom of the crowd to decide which to read. Prefer dense, older books over beginner-friendly, newer books. Time-tested is more important than ease of reading.
Interviews. Find 1~2 video or audio channels in which practitioners, preferably skilled ones, are interviewed. Prioritize interviews in which their training methodologies and lessons are shared. Look for patterns of what to do and what not to do.

Whatever you learn, find a way to apply it, regardless of the simplicity of the experiment. Knowledge only becomes useful (and ingrained) when applied.

The goal of this phase is to:

Decide (again): double-down or pivot to another skill/field. Progress slows in the next phase. The journey becomes more important than the reward. Ensure curiosity exists. When in doubt, listen to your gut: does this energize me?
Know what you don’t know. To identify your circle of competence and create your roadmap.
Identify overlap with existing skills and knowledge. (How) can you connect it with something you’re already proficient in or are currently doing? (Overlap accelerates the acquisition of knowledge and skill and increases memory retention.)

You can complete this phase in 1 to 3 months.

3. Intermediate

At this stage you want to emphasize output (doing) over input (studying, researching).

Let your curiosity decide what to focus on next.

Do, build and experiment as much as you can. Failure rates will be high. Review and reflect on every experiment – if in doubt, reflect and journal daily.

Use this feedback loop to identify gaps in your knowledge and develop your personal curriculum. Your personality, skills, interests, assets and circumstances are unique – with time your roadmap will diverge more and more from others.

Intermediate practitioners will have less to teach you – upgrade your mentors (unnecessary if you focused on historical greats from the start). Peers can be useful for emotional support as your challenges and failure rates will be more similar (compared to mentors).

In terms of knowledge acquisition (input):

Gaps to grow. Your (failed) experiments inform you what you’re lacking. Find books, interviews or successful projects you can reverse-engineer that directly address these gaps. This expands your knowledge.
Teach to review. Review the high-quality, foundational books you’ve read in the earlier phases as well as any other resources you found useful. Teach it directly to others (the younger, the better) or indirectly by publicly writing about it. If time allows, do both. Explanation illuminates understanding and exposes misunderstanding. This solidifies your knowledge.
- Writing. “Clear thinking becomes clear writing” – William Zinsser. To learn to write well (and create clearer thoughts), produce 5 versions:
  - A 3 page version.
  - A 1 page version.
  - A 3 paragraph version.
  - A 1 paragraph version.
  - A 1 sentence version.
Study great practitioners. Continue to study and deconstruct greats, and observe patterns of success and failure. This improves and accelerates your learning process.

Remember: knowledge is a means to an end.

Let your experiments identify knowledge gaps, which you fill by studying and teaching, and then (re)test with experiments. This creates a virtuous cycle.

In this phase you want to output much more than you input and start personalizing your roadmap.

You can complete this phase in 6-24 months.

4. Advanced

Progress further slows. And as you learn more you realize how much more there is to learn. Like in the Beginner phase, it’s easy to fall in the trap of reading, studying and researching.

But what we’re after is not the acquisition of knowledge. What we want is the acquisition of skill, the expertise in a field, that lets us solve more difficult problems, make greater contributions to the world and help us progressively realize our worthy ideal. We’re doing this to make the most of our life and, in the process, enjoy it to its fullest.

Your experiments – the problems you’re trying to solve – and their feedback dictate your next step. Continue to emphasize building and reflection over studying and research.

In terms of knowledge acquisition (input):

Experts. You now require specialized knowledge that books (or other media) are unlikely to provide. Seek out experts and question them. Life at the top is lonely: your expertise may differ but with your shared foundation you’ll find many experts open to high-level discussions with peers – they face the same knowledge-acquisition problem you do.
Teach. Continue to teach the fundamentals as in the previous phase. Teach increasingly younger and more inexperienced students. This forces simplification which, in turn, improves understanding. Complement this with teaching and writing about your current (more advanced) experiments to/for a lay audience. This dual strategy of teaching both the fundamentals and your most advanced work forces clear thinking, exposes gaps and accelerates your learning.

In this phase you want to pursue your personal roadmap and solve the problems that most interest you. In the process, you:

Build a network of peers and get energy from social interactions.
Give back to others by teaching to enjoy the selfish benefits of clearer thinking, accelerated learning, increased reputation and opportunities, and an added sense of meaning in life.

Both social endeavours also invite more serendipity which, eventually, leads to breakthroughs, further accelerating your process and improving the mastery of your skill.

You’ll never complete this phase. Enjoy the journey of uncovering increasingly more depth.

Skill acquisition

We can acquire skills through different means:

We learn to walk by trial-and-error.
We learn to understand language by osmosis.
We learn to play sports by joining experienced friends.
We learn math by a combination of practice and feedback.
We learn to read by a combination of instruction and exposure.

But some means lead to faster acquisition. And only some lead to excellence.

There are two dominant schools of thought:

The Western, rational approach. I call this the Scientist.
The Eastern, intuitive approach. I call this the Artist.

Modern education combines the least effective aspects of both to produce a third school, which I call the Labourer.

But the best learners combine the most effective aspects to produce the best school: the Craftsman.

Let me explain their characteristics.

Scientist

This school finds its roots in Aristotelian science and rewards consistent effort.

Follow a blueprint
Learn and add
Emphasizes iteration and gradual improvement
Teach the fundamentals, then focus on training holistically
Alternate study, practice and review to understand rationally
Deliberate practice that reinforces strengths and addresses weaknesses
Learn by feedback loops
Coaches and mentors give explicit explanations

Artist

This school finds its roots in Taoist (and later Zen Buddhist) spirituality and rewards patient perseverance.

Follow a master
Unlearn and subtract
Emphasizes consistent effort and breakthroughs/enlightenment
Show the whole, then focus on the basics
Do to develop an intuitive understanding
Continuous practice of the fundamentals
Learn by repetition and osmosis – Master explains implicitly through pointers and aphorisms

Labourer

This school finds its roots in Fordian mass-production methods and rewards obedient replication.

Theoretical without the practical
No tools, only information
Memorization over intuitive or rational understanding
Reading, studying and tests over doing, practice and experimentation
A one-size-fits-all blueprint
Misunderstanding that people learn, understand and grow at different rates and in different ways: our brains are the same yet our genes, experiences and environments make them unique.

Craftsman

This school finds its roots in ancient ways of preserving and advancing wisdom, got revived in Medieval apprenticeships and rewards curiosity-driven repetition.

Observe and study only masters, avoid random teachers. Copywork whenever possible.
Favour doing, tinkering and experimenting over reading, listening and studying (the latter supplement the former)
Fundamental over advanced techniques. Advanced techniques are nothing more than a recombination of the fundamentals. Learn the fundamentals to learn the advanced; the reverse is not true. Advanced techniques change, fundamentals remain.
Teach as soon as possible. Teach only the fundamentals. Teaching exposes misunderstandings, reveals new insights. Never give up teaching.
Write down your observations and experience from day 1. Writing clarifies the mind and declutters.
Remove the unessential. Simplification shortens the journey.
Understand that mastery is an illusion. Every skill possesses infinite depth. Chess is 1500 years old and Go is even older (4000 years): fundamental opening moves are still studied today.
Practice only what energizes. The road is long (frankly endless) so better walk one you enjoy.

What the best do

All the historical greats in their fields – from gold medalists to Nobel laureates, from billionaires to master artisans, from gurus to tech wizards – follow the Craftsman approach. They understood that skills are acquired, not learnt.

They also realized that every approach brings progress. With enough time, one can become a skilled expert using any of the approaches.

They know that persistence and patience are the necessary ingredients to make any of the approaches work. What makes us fail is not the means, teacher or system: it’s us. Our impatience. Impatience is what kills our dreams.

Remember: competence takes effort, excellence takes commitment, mastery takes a lifetime.

The right approach to knowledge and skill acquisition accelerates your journey – increases your stride – but it’s your effort that lets you progress – to take that step forward.

With persistence, success in any endeavour is inevitable. Without it, failure and disappointment are the most likely outcomes.

Bonus – DiSSS and CaFE

This is the approach polymath Tim Ferriss has developed (and tested) to deconstruct any skill and acquire it efficiently. The below is all his work, but I’ve found it very useful and deserving to be shared.

DiSSS

Deconstruction: what are the minimal learnable units with which I should start?
Selection: which 20% of the blocks should I focus on for 80% or more of the outcomes I want?
Sequencing: in what order should I learn the blocks?
Stakes: how do you set up stakes to create real consequences and guarantee I follow the programme?

CaFE

These are secondary – inessential but beneficial – principles.

Compression: can I encapsulate the most important 20% into an easily graspable one-pager?
Frequency:
- How frequently should I practise?
- Can I cram and what should my schedule look like?
- What growing pains can I predict?
- What is the minimum effective dose (MED) for volume?
Encoding: how do I anchor the new material to what I already know for rapid recall?

“Deconstruction is best thought of as exploration. This is where we throw a lot on the wall to see what sticks. Where we flip things upside down and look at what the outliers are doing differently and also what they’re not doing at all.

First and foremost is where we answer the question, how do I break this amorphous so-called skill into small, manageable pieces? Just as with literal deconstruction, taking a building apart, for instance, or demolishing something, breaking it apart, whatever it might be, dissecting something, you need the right tool for the job. In our case, one of the best tactics is interviewing.”

Fundamental skills

These are the skills I’ll teach my children – before anything else – and I believe everyone would do well to learn/improve in. I think they provide outsized returns as well as make the acquisition of other skills easier.

In short: you’d do yourself a favour to learn these first.

Life skills

Think clearly. Improve thinking to improve decisions. Decisions compound.
Ask better questions. Better questions lead to better answers. Better answers make life easier.
Understand others, understand the world. Learn another language, experience another culture, live in a different environment. Learn what we share and how we differ. This lets you understand yourself.
How to learn. Specifically, how to read, how to write and how to acquire skills.
- Reading well lets you learn from the wisest minds in history and the mistakes of others.
- Writing well clarifies your mind and lets you communicate effectively.
- Learn skills well and quickly to never go hungry.

Money skills

Persuasion. Learn to sell verbally or in writing and you can live and work anywhere.
Creation. Learn to create physical goods, digital goods, communities or pieces of art and you can find a patron anywhere.
Investing. Learn to preserve wealth to attract the wealth of the rich. Learn to grow wealth to attract the wealth of all. But remember: no bet that can destroy wealth is ever worth it.

Personal qualities

Reliability. Nothing is more difficult to acquire, easier to lose and nearly impossible to regain than trust. Remain reliable and treat trust as you would your most valued possession.
Perseverance. Hardships are inevitable. Remain patient with results but be impatient with action.
Generosity. Reciprocity pays.
Temperance. Desires little and you become instantly wealthy.
Frugality. Spend less than you earn and you will never be poor.
Humility. No fortunes or friendships are faster lost than by an abundance of arrogance.

The Skill-Serendipity-Success System

Putting it all together

For every (new) endeavour, failure is the default. It’s the expected outcome.

The only thing that can guarantee success is persistence. Play the game long enough and success becomes inevitable.

The same applies to this game called life.

In the short-term, we may measure success in financial terms. But in the long-term, pretty much everyone measures success in a life well-lived, in a meaningful life.

This, in my opinion, involves finding (and working on) something that one truly cares about. That’s how we can feel alive, get the most out of our life AND give the most back to the world. To fulfil our destiny, if you’d like.

But how to find this ever-burning passion?

Play the game long enough and success becomes inevitable.

There’s really no way around it: you have to try and experience many things – play many games – until you stumble upon it. Until serendipity hits you in the face.

Some are lucky and find it in their childhood. Others don’t find it until they’re retired. Some – those who settle in life – never do.

As we get older we lose one asset – time – but gain, if we play the game right, other assets to work with – knowledge, skills, relationships, wealth, to name a few. These assets allow us to play more games, play them for longer and accelerate the pace at which we play.

We can shorten the game.

That’s what my Skill-Serendipity-Success System (3S System) is all about. To increase our assets, allow for more serendipitous moments and shorten the time it takes to be successful. To live that energizing, fulfilling, meaningful life we’re destined for.

How it works

You create your personal 3S System programme based on what’s important to you – by going from the long-term to the short-term.

My preference is:

Lifetime (purpose)
Decade (lifestyle)
Year (business/income)
Quarter (skill and outcome)
Month (product or service)

I found my life’s purpose and use it as my north star. Working backward, I know the personal and professional foundation I want to build this decade.

Coming up with an annual theme – in the form of a new business or source of income – becomes easy.

But if you can’t easily imagine a desirable future, simply pick an industry or field you want to be proficient in. Think of it like picking a major in college – except you’ll complete it in 1 year (totally doable). This becomes your theme for the year.

Why do I focus on creating a new business or source of income every year?

Business forces us to produce something of value to others.
This forces us to create something – to apply our knowledge.
Tests are black and white. Markets are grey. The world is grey.
Markets and customers provide quick feedback. This accelerates learning.
Customers are ruthless and go where they receive the highest value. This forces continuous improvement.
Markets give money to valuable solutions. Money is useful.

Why do we do anything? Because it makes us feel good, improves our life and/or sustains our life. All three are best achieved, in my opinion, by creating something of value to others.

Knowing the business I want to build or the industry/field I want to become proficient in, I ask myself: what are the essential skills to make this year a success?

This prompt might produce many skills to learn. I reduce my list to a maximum of 4, giving me 1 per quarter. If this is difficult, change the theme for that year or reduce its scope. Life is long and skills compound. You can try your original vision next year.

If unsure which skills to prioritize, pick those closest to the fundamental skills elsewhere in this guide.

Focus on 1 skill per quarter. Leave the others for later. Focus accelerates progress.

Each month find 1 problem you can solve in your chosen field, using your chosen skill, within 1 month. Ideate, validate, build and ship the solution before the end of the month. If it cannot be done in 1 month, scale down your idea or select a different one. Use any assets or previously acquired skills as leverage.

You acquire skill by doing. You attract serendipity by shipping solutions. You become successful by repetition and persistence.

At first, you won’t be able to do much. Your first solution will almost certainly fail. But as you repeat this pattern, month after month, you start acquiring small successes.

Every quarter you acquire a new skill. Those skills start stacking. Your circle of competence expands. You can take on bigger, more valuable problems.

And all of this is done in public. That’s how you attract serendipity.

Every month you share your solution. Every quarter you share how you learnt this skill – what worked and what didn’t. Every year you share your reflections on 12 projects and lessons about a field, then share your roadmap for the following year where you’ll do it all again.

The 3S System isn’t easy. It requires effort. But progress and personal development is guaranteed. And that’s what makes it exciting (to me, at least).

Success – financial as well as fulfilment – is guaranteed if you persist long enough.

And best of all: you decide your roadmap, the direction in which you want to take your life. Whatever floats your boat. Whatever gets you excited. Whatever energizes you.

A simple playbook to get started

What would I like to be doing 1-5 year(s) from now? This can be your “calling” or “passion” but doesn’t have to be. Action produces information, so work with whatever comes to mind now.
Which skills do I need to do that work well?
Which of these skills is most important? In other words, what is the foundational skill? (I’ll elaborate on this below)
What can I do now to train this skill?
Can I take on a project inside my current company that lets me train this skill? (= get paid to learn) If not: what can I do outside of work to apply this skill? (use it for an acquaintance, create a solo project, teach this skill to a nephew/niece)
Document (preferably publicly) all your successes and failures involving this skill. Turn everything into a case study with lessons learnt. Over time, case studies position you as a teacher rather than a student.

That’s basically it.

“Ask and thou shalt receive.”

I’d add to that: “if proven you can do the work.”

Demonstrable skill breeds trust. Trust brings opportunities.

Imagine this scenario:

Two people come to you for a job.

Person A says: “I haven’t done it before, but I’m eager to learn. I’m a team player, determined and open to working long hours.”

Person B says: “My previous work experience was completely different, but I’ve taught myself the skills needed for this job in my spare time. Here’s the work I’ve done.”

Hiring person A is a gamble. Hiring person B is a calculated bet. That’s the power of demonstrable skill.

It works in every industry and for every employment status. Best of all: it breeds confidence. And confidence alone can move mountains.

That’s the playbook.

Acquire the skill you need (not just random ones), demonstrate it long enough and you go from hunting for opportunities (= sending cold emails or cover letters) to sitting back and rejecting 90% of them (= having leads, clients and referrals come to you).

The next step: where to go from here

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I don’t have it all figured out but I learn, self-experiment and do my best to walk the slow march toward greatness with you.

Jim Bouman