Josh Kaufman

Bestselling Author, Business & Self-Education


The Best Essays I Read in 2016

As part of my annual review process, I took a few hours to look through my research database for great essays and blog posts I read in 2016. Major research topics this year included business, entrepreneurship, learning, skill acquisition, productivity, psychology, health, science, systems, wisdom, and general life satisfaction. 1

Of the 804 posts I saved, here are a few of the best. (You can also browse my selections from 2015, 2014, 2013, and 2012.)

(Note: these are essays I read and saved in 2016. Original publication dates for the essays themselves may vary.)

Lara Hogan: "Work At Different Management Levels"

I remember working as a developer at a company and complaining that I had no idea what the bosses did all day. It felt like while we engineers were working hard and shipping stuff, managers just talked to a lot of people all the time, or sat in their offices behind closed doors, and I had no idea what their work looked like…

… Given how intangible (and often hidden) management work can be, I’ve outlined some highlights of what my work has been like as a manager over the last four years.

Read the full post →

Oliver Burkeman: "Are You An Asker Or a Guesser?"

In Ask culture, people grow up believing they can ask for anything – a favour, a pay rise– fully realising the answer may be no. In Guess culture, by contrast, you avoid "putting a request into words unless you're pretty sure the answer will be yes…

… Neither's "wrong," but when an Asker meets a Guesser, unpleasantness results. An Asker won't think it's rude to request two weeks in your spare room, but a Guess culture person will hear it as presumptuous and resent the agony involved in saying no.

Read the full post →

Kevin Simler: "A Nihilist's Guide to Meaning"

Supposing there's no ultimate, objective, metaphysical thing called meaning, we might instead approach it as a certain feeling or perception that people have toward the objects, events, and experiences in their lives, or toward their lives as a whole…

So far I've been waving my hands in the general direction of meaning, without trying to put too fine a point on it. Now I'd like to venture a more explicit hypothesis about what, exactly, underlies our perceptions of meaning. Please forgive the mathy tone here:

“A thing X will be perceived as meaningful in context C to the extent that it's connected to other meaningful things in C.”

Read the full post →

Mark Manson: "In Defense Of Being Average"

Today, I want to take a detour from our “make more, buy more, f**k more” culture and argue for the merits of mediocrity, of being blasé boring and average.

Not the merits of pursuing mediocrity, mind you — because we all should try to do the best we possibly can — but rather, the merits of accepting mediocrity when we end up there despite our best efforts.

Read the full post →

80,000 Hours: "Everything You Need To Know About Whether Money Makes You Happy"

It’s a cliché that “you can’t buy happiness”, but at the same time, financial security is among most people’s top career priorities. Moreover, when people are asked what would most improve the quality of their lives, the most common answer is more money.

What’s going on here? Who is right?

Read the full post →

Jacques Mattheij: "CEO"

In this post I’m going to try to give potential and actual CEO’s (and other C level execs to some extent) some actionable advice when it comes to how they conduct themselves in the hope that this will at some future date save some of you a great deal of misery and in some cases charges of misconduct or worse.

My hope is that this will somehow help save a few companies by causing you - the CEO - to change direction before it is too late to do so.

Read the full post →

Julian Baggini: "Recipe For Success"

Is it possible to be highly successful without caring for recognition? […]

It sounds simple: the only ambition worth holding is to do whatever it is that you want to do as best you can; the only true measure of success is whether you manage to do that. But the austerity and purity of this vision of the good life comes up against a problem. It seems impossible to judge our own success without some external measure. And this is not entirely mistaken… Success does not require recognition, but it is better on the whole that people hear your music, read your words, taste your food, than not. […]

But as recognition widens, it can also become very shallow. What should matter is the deeper appreciation that comes from people who know you and your work more intimately… When recognition steps over the threshold into fame, it often becomes so thin because it ultimately ends up being sustained by itself. Recognition breeds recognition so, in the end, even those who are initially recognised for real achievements end up being famous mainly for being famous.

Read the full post →

Scott Alexander: "Nonfiction Writing Advice"

People have asked me for advice on writing nonfiction online, so here are some tips:

  1. Divide things into small chunks
  2. Variety is the spice of life
  3. Keep your flow of ideas strong
  4. Learn what should and shouldn’t be repeated
  5. Use microhumor
  6. Use concrete examples
  7. Figure out who you’re trying to convince, then use the right tribal signals
  8. Anticipate and defuse counterarguments
  9. Use strong concept handles
  10. Recognize that applying these rules will probably start disastrously
Read the full post →

James Clear: "Overrated vs. Underrated: Common Beliefs We Get Wrong"

As a society, we often overvalue unimportant things and undervalue the ideas and strategies that make a real difference.

Here’s my take on a few common beliefs that I think we often get wrong.

Read the full post →

Patrick McKenzie: "The Stripe Atlas Guide To Starting A Real Business"

Many of the mechanics of running a business are opaque, particularly to first-time entrepreneurs. You may not have done bookkeeping or contract negotiation before. You might be used to working in companies with processes and people in place to support your work. Don’t worry! Every skill involved in running a business is learnable, including by you, specifically. […]

Hopefully this helps to demystify some of these concepts and free you up to go back to creating value and finding customers for it.

Read the full post →


This post has been back-dated to December 31, 2016 for archival purposes.


  1. Programming and software development was a major interest this year, as it has been since I learned web application programming while writing The First 20 Hours in 2013. Technical posts were not included in this digest. I also set aside excellent essays and posts related to the more technical aspects of my own business (writing, publishing, teaching, etc) to make this digest more applicable to the interests of my readers. 


Published: December 31, 2016 Last updated: January 16, 2017

I Enjoyed This Post
Read more essays by Josh Kaufman →

The Personal MBA

Master the Art of Business

The #1 International Bestseller, Revised & Expanded. A world-class business education in a single volume. Learn the universal principles behind every successful business, then go out into the world and make your own. More →



The First 20 Hours

How to Learn Anything… Fast!

A practitioner's guide to rapid skill acquisition. Accelerate your learning by deconstructing complex skills, practicing the most important elements first, and removing barriers to deliberate practice. What do you want to learn? More →