Ten Books for Rolling the Career

· 2097 words · 10 minute read

Modern careers can feel daunting. This is because the central driving force of society has shifted from the state to the corporation, and now, to the individual. (I discussed this mega trend further in my reviews of <How Asia Works>.)

Consequently, traditional, standardized career paths, such as steadily climbing the corporate ladder or relying on long-term employment with a single large company, are no longer a fit for most people. With careers becoming so fragmented, it’s no longer possible to directly apply anyone else’s advice. Instead, we’ve gained both the freedom and the responsibility to define our own paths and take action.

In this state of feeling lost, especially when you don’t have something you’re particularly skilled at or passionate about, good books can be immensely helpful. They played a big part in my ability to put together articles like <Career Snowball> (and v2). Having now read over 300 books, I’d like to introduce 10 from that list that are great starting points. These books might not completely eliminate your feeling of being overwhelmed. But I hope they can give you the strength and determination to navigate it, even if you don’t agree with everything they say.

Perspectives

  1. The Startup of You: Adapt to the Future, Invest in Yourself, and Transform Your Career
  2. Only the Paranoid Survive: How to Exploit the Crisis Points that Challenge Every Company and Career
  3. How to Fail at Almost Everything and Still Win Big

Execution

  1. Deep Work: Rules for Focused Success in a Distracted World
  2. Grit: The Power of Passion and Perseverance
  3. Ultralearning: Master Hard Skills, Outsmart the Competition, and Accelerate Your Career

Strategy

  1. The Art of Strategy: A Game Theorist’s Guide to Success in Business and Life
  2. Fooled by Randomness: The Hidden Role of Chance in Life and in the Markets
  3. The New Geography of Jobs
  4. How Will You Measure Your Life?

Book Stairs

Perspectives 🔗

Shaped by a 20th-century education, we often approach careers from a static perspective. We tend to envision well-defined roles like doctors, lawyers, or teachers, achieved by methodically acquiring qualifications or degrees to reach a predetermined goal.

However, the world is changing at an ever-increasing pace. We can no longer be sure that the jobs of today will even exist in a decade — much like it was difficult to imagine ‘YouTuber’ as a profession ten years ago. This uncertainty also presents an opportunity to fundamentally reassess how we approach our careers.

1. The Startup of You 🔗

  • Background: 2012, Silicon Valley, LinkedIn
  • Past review: 2013-07-03

Today’s dynamic careers are less like passing an exam and more like launching a startup. This is because, even if you’re not founding a company yourself, you constantly have to make decisions and take action amidst uncertainty. It’s also similar in that if you don’t create value, it’s difficult to survive in the market, and your efforts alone might go unrecognized. Reading this book when I was just starting out was a great help in figuring out my career direction.

With the death of traditional career paths, so goes the kind of traditional professional development previous generations enjoyed. You can no longer count on employer-sponsored training to enhance your communication skills or expand your technical know-how. The expectation for even junior employees is that you can do the job you’ve been hired to do upon arrival or that you’ll learn so quickly you’ll be up to speed within weeks. Whether you want to learn a new skill or simply be better at the job you were hired to do, it’s now your job to train and invest in yourself.

2. Only the Paranoid Survive 🔗

The reason traditional career paths are vanishing is because the world is changing so rapidly. Technologies like AI, cloud computing, and mobile platforms, which were hard to even conceive of 10-20 years ago, are now part of our daily lives. Assuming the world will continue its rapid transformation, the best approach is to accept this reality and learn to leverage it.

Although it’s an older book, the core wisdom of its author, who flexibly navigated Intel through tumultuous shifts in technology and the global landscape, seems to shine even brighter with time (even if Intel itself is currently facing significant challenges).

Srategic inflection point is a time in the life of a business when its fundamentals are about to change. … You need to plan the way a fire department plans: It cannot anticipate where the next fire will be, so it has to shape an energetic and efficient team that is capable of responding to the unanticipated as well as to any ordinary event.

3. How to Fail at Almost Everything and Still Win Big 🔗

One of our common mistakes is to confuse cause and effect. This book humorously unravels how the supposed causes and effects presented by traditional career perspectives are often completely inverted. For instance, it argues that characteristics we instinctively view as positive — such as having clear goals, passion, or a strong performance record — may actually have very little correlation with building a successful career. If you’re prepared to let go of rigid thinking, this book can offer a more flexible and adaptive perspective on your career.

Goal-oriented people exist in a state of continuous pre-success failure at best and permanent failure at worst, if things never work out. Systems people succeed every time they apply their systems in the sense that they did what they intended to do. The “goals” people are fighting the feeling of discouragement at each turn. The systems people feel good every time they apply their system.

Execution 🔗

If modern careers are dynamically built, then the methods for executing them must also differ from the static approaches of the past. While diligence and broad knowledge were once the keys to success, today the advantage goes to those who practice deep immersion, flexible persistence, and hands-on learning.

4. Deep Work 🔗

  • Background: 2016

We constantly stay busy responding to emails, Jira tickets, and Slack messages, yet it’s often hard to pinpoint what we’ve actually accomplished at the end of it all. The author suggests that true value stems from depth. Rather than deluding ourselves into thinking we’re working by answering dozens of messages, it’s more meaningful to tackle a single, challenging problem and produce a tangible result.

The goal shouldn’t be to simply work more hours, but to secure time for focused immersion, even if the total time is shorter. This allows you to concentrate on the few key outcomes that are truly worthy of that deep work.

The ability to perform deep work is becoming increasingly rare at exactly the same time it is becoming increasingly valuable in our economy. As a consequence, the few who cultivate the skill, and then make it the core of their working life, will thrive.

5. Grit 🔗

  • Background: 2016

What is most important among factors like passion, talent, or interest? The author, an expert on this topic, argues after extensive research that “grit” is the most crucial element, dedicating an entire book to explaining its meaning. The process of creating something meaningful in a highly uncertain world involves overcoming numerous trials and errors. In a world where everyone desires instant results, the value of grit will shine even brighter.

talent x effort = skill
skill x effort = achievement
Enthusiasm is common. Endurance is rare.

6. Ultralearning 🔗

  • Background: 2019

The fact that people are now working in jobs that didn’t exist ten years ago signifies a surge in the importance of learning, and it means the effective lifespan of degrees and certifications has shortened. The author contends that rapidly acquiring applicable skills is vastly different from the traditional study aimed at accumulating knowledge, and proposes new methods of execution.

Personally, I struggled for some time because I didn’t understand this distinction; trying to solve deficiencies solely through knowledge acquisition often only makes the problem worse. Instead, acquiring skills through practical application and producing results seems to be a more fitting direction in the modern era.

The phrases learning something new and practicing something new may seem similar, but these two methods can produce profoundly different results. Passive learning creates knowledge. Active practice creates skill.

Strategy 🔗

To apply these new perspectives and methods, it’s helpful to approach your career as a long-term strategy game. This involves objectively assessing the present, making predictions about the future, and structuring your actions to maximize gains when you’re right while minimizing losses when you’re wrong.

7. The Art of Strategy 🔗

One of the biggest changes we experience when moving from school to the professional world is that the game shifts from single-player to multi-player. The foundation of any multi-player strategy is to consider the perspectives of the other players.

Playing with the viewpoints of your employer, manager, clients, or investors in mind will lead to vastly different outcomes than stubbornly sticking to only the moves you personally believe are correct. In that sense, game theory, which explores the essence of such interactions, is an essential starting point for career strategy.

When thinking strategically, you have to work extra hard to understand the perspective and interactions of all the other players in the game, including ones who may be silent. … You may be thinking you are playing one game, but it is only part of a larger game. There is always a larger game.

8. Fooled by Randomness 🔗

Humans are naturally weak at understanding probability, and the media often confuses us with rare, outlier events. The author’s own field, the financial industry, is particularly full of examples where luck is mistaken for skill. For example, before the 2008 financial crisis, bankers grew arrogant from their subprime successes before collapsing, but not everyone who gets lucky ends up failing.

While dismissing a career as pure luck is too simplistic, ignoring the importance of luck is dangerous. Just as it’s difficult to beat professional poker players even though the game is based on luck, a good strategy is incredibly useful even when luck plays a major role.

Things are always obvious after the fact. … When you look at the past, the past will always be deterministic, since only one single observation took place. Our mind will interpret most events not with the preceding ones in mind, but the following ones. … Psychologists call this overestimation of what one knew at the time of the event due to subsequent information the hindsight bias, the “I knew it all along” effect.

9. The New Geography of Jobs 🔗

While one-person businesses and fully remote work are emerging as viable options, the majority of careers still revolve around specific jobs and cities. Even when performing the same role, simply being in a city with many alternative employers can give you a significant advantage in negotiations.

This dynamic is so powerful that even seemingly dominant Big Tech companies must pay much higher salaries in certain cities. Just as the surrounding terrain is crucial in a strategy game, understanding and leveraging your environment provides a powerful strategic advantage.

Clusters can’t afford to cling to a declining industry but need to leverage their unique strengths to reinvent themselves before the tipping point is reached and the local ecosystem enters a downward spiral.

10. How Will You Measure Your Life? 🔗

The author, an expert in business management, explains that running a company and living a life are fundamentally similar. Just as an individual who only chases money struggles to truly prosper, a company obsessed only with profits often meets a disastrous end, like Enron. A career is challenging enough on its own, but ultimately, you alone can decide on the standards for your life, and you must allocate your time accordingly.

This is not easy for anyone - as seen with the author’s once-promising Harvard classmates who ended up in prison, and the many billionaires who get divorced or whose children go astray. While there’s no perfect solution, it is ultimately your responsibility to manage.

If you want your kids to have strong self-esteem and confidence that they can solve hard problems, those qualities won’t magically materialize in high school. You have to design them into your family’s culture—and you have to think about this very early on. Like employees, children build self-esteem by doing things that are hard and learning what works.

career book strategy