Weekly Learning: The Career Edition


Tim Urban’s How to Pick a Career (That Actually Fits You) is a must-read for anyone who ever wonders about career path, because:

This post isn’t me giving you career advice really—it’s a framework that I think can help you make career decisions that actually reflect who you are, what you want, and what our rapidly changing career landscape looks like today.

When you’re young:

…you’re kind of skill-less and knowledge-less and a lot of other things-less…

And there’s a bigger issue:

Kids in school are kind of like employees of a company where someone else is the CEO. But no one is the CEO of your life in the real world, or of your career path—except you. And you’ve spent your whole life becoming a pro student, leaving you with zero experience as the CEO of anything.

That path-making can be profound:

When scientists study people on their deathbed and how they feel about their lives, they usually find that many of them feel some serious regrets. I think a lot of those regrets stem from the fact that most of us aren’t really taught about path-making in our childhoods, and most of us also don’t get much better at path-making as adults, which leaves many people looking back on a life path that didn’t really make sense, given who they are and the world they lived in.

Here’s an important analogy of being a chef vs. being a cook:

A pure verbatim recipe-copying cook and a pure independently inventive chef are the two extreme ends of what is, of course, a spectrum.

There’s a spectrum in how you reason and make decisions:

…your reasoning process can usually be boiled down to fundamentally chef-like or fundamentally cook-like. Creating vs. copying. Originality vs. conformity.


Career-path-carving is definitely one of those really really deeply important things.

Boxes, octopus, tentacles, and game board ensue:

A career path is like a game board.

But we often mistake skill level for reaching a career goal:

Reaching the “I want to be a famous actor” star doesn’t simply mean getting as good at acting as Morgan Freeman, it means getting as good at the entire actor game as most movie stars get by the time they break through. Acting ability is only one piece of that puzzle—you also need a knack for getting yourself in front of people with power, a shrewdness for personal branding, an insane amount of optimism, a ridiculous amount of hustle and persistence, etc. If you get good enough at that whole game—every component of it—your chances of becoming an A-list movie star are actually pretty high.

There’s also kind of a tunnel vision thing:

Careers used to be kind of like a 40-year tunnel. You picked your tunnel, and once you were in, that was that.

While the truth is:

…careers have probably never really functioned like 40-year-tunnels, they just seemed that way.


Today’s careers—especially the less traditional ones—are really really not like tunnels. But crusty old conventional wisdom has a lot of us still viewing things that way, which makes the already hard job of making big career path choices much harder.

The danger:

When you think of your career as a tunnel, you lose the courage to make a career switch, even when your soul is begging for it.

What’s most resonant to me:

If a career is like connecting the dots, we should probably rank “getting wise about dot-jumping” pretty high on our to-do list. The best place to start is by looking at your own past. Studying your own past decisions, with the flashlight of hindsight and accumulated wisdom, is like an athlete studying game tape.

Yeah, you really should read the article in full.


Scott Berkun’s Are You a Self-Limiting Designer? Touches something critical about being a professional, designer or not:

The only way organizations that produce mediocre work improve is when someone with design knowledge either becomes a decision maker, or improves their skill at influencing decisions. This means facilitation, persuasion and relationship building can be just as essential to good design as design plans themselves. But when these skills are frowned upon or stigmatized, the self-limiting idea of a designer holds back entire teams.


Dan Saffer recounts his Lessons from a Job Search:

There’s an idea held by many that the more experienced you are, the more accomplished you are, the better your network, the easier it is to find a job. I’m here to debunk this.

It’s important to remember that:

While it shouldn’t be, the job market is a numbers game.


Unless the work in your portfolio is closely related to the work their company does, they will have trouble extrapolating it to their domain. You need to do this work (if you can) for them.

And of course:

Expect your job search to take 150% more time than you think it will.

Wage Slavery

In Are You a Wage Slave? one of my favourite authors Nir Eyal asks: “Can we create a future where people no longer have to work at jobs they hate?”

Being a wage slave means:

…you are stuck doing a job solely for the money. You can’t quit, because leaving would have terrible consequences for you and your family.


Every job involves doing some tasks we don’t enjoy. A job doesn’t have to be perfect all the time to be a good job. As long as there are reasons other than “my family may become homeless” that keep you coming back, it’s not wage slavery.

So how do we avoid long-term wage slavery?

To avoid long-term wage slavery, workers who want to leave their jobs need to have options. They need to have an alternative to their current situation that doesn’t involve going hungry (or going without basic necessities).


…wage slavery isn’t only about how much people make; it’s about the freedom to walk away to choose a better option.


As a society, we owe it to ourselves to pursue freedom from wage slavery. A century from now, I hope we’ll look back and wonder how we ever accepted otherwise.


Embrace the Grind uses the analogy of magician implementing magic trick to make an incredibly important point:

…being willing to do something so terrifically tedious that it appears to be magic…

The lesson:

If you’re willing to embrace the grind you’ll look like a magician.

The author surely did magic:

People said I did the impossible, but that’s wrong: I merely did something so boring that nobody else had been willing to do it.

Sometimes, no pain no gain is real:

…sometimes, magic is mundane. If you’re willing to embrace the grind, you can pull off the impossible.


When your authenticity is an act, something’s gone wrong asks:

Is authenticity fading away as a personal ethic or is it something everyone wants to be? In fact, both are true – because the meaning of authenticity is changing.


…as an ethical ideal – as a standard of what it is good to be, both in the way that we relate to ourselves and others – authenticity means more than self-consistency or a lack of pretentiousness. It also concerns features of the inner life that define us.

Secondly, there’s a shift of values in authenticity:

The register of values has shifted…away from anything standardised and regular and toward objects, images, services and events that are regarded as being unique and singular.

And that led to “performative authenticity”:

Performative authenticity is tied to economic success and social prestige, which means – and this is a further paradoxical feature – that your specialness and self-realisation have to be performed.

If that’s not stressful, then I don’t know what is.


Stockton’s Basic-Income Experiment Pays Off informs that a “new study of the city’s program that sent cash to struggling individuals finds dramatic changes.”

Supposedly, there’s a common perception:

In the United States, poverty is used as a cudgel to get people to work. We got rid of welfare for poor families’ and poor individuals’ own good, the argument goes. Give people money, and they stop working. They become dependent on welfare. They never sort out the problems in their life. The best route out of poverty is a hand up, not a handout.


Stockton has now proved this false. An exclusive new analysis of data from the demonstration project shows that a lack of resources is its own miserable trap. The best way to get people out of poverty is just to get them out of poverty; the best way to offer families more resources is just to offer them more resources.


The Time-Block Planner is “A Daily Method for Deep Work in a Distracted World.”

Currently Reading

And of course you’ll never know what I’m actually reading.


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