The Best Articles on Life Philosophy

How should you live? In many ways, my blog is devoted to trying to pull apart and answer this question. Over the last decade, I’ve written a lot trying to do this, here are some of the best articles.

The 5 Best Life Philosophy Articles

Here are my best five essays on how to live better:

Most Books Won’t Change Your Life (But You Should Read Them Anyways) – You should read more books, even if you can’t apply them all.
Can Life Have Too Much Meaning? – We tend to think of meaning as something we want more from life, not less. However, many symptoms of modern life may actually be from having too much meaning, not too little.
Is Reading Blogs Like This One Keeping You From Improving Your Life? Is reading a complement or substitute for doing the work of self-improvement?
Should You Target the Minimum? – I discuss minimum, average and maximum targeting and how these three different approaches differ for pursuing all sorts of goals.
Are You Living Your Life or Just Planning Your Biography? – The difference between how life is experienced and how it is remembered can result in choices that make you worse off.

On Achievement and Failure

Here are some of my thoughts on achieving success and overcoming the failures that come with it:

Fear Fizzle More than Failure – Most efforts die out long before we could call them failures. To really succeed, live in a way that true failure is also a possibility.
The Three Different Types of Luck – Chance influences all outcomes, but not all types of luck should have the same response.
What’s Next? How to decide what to do after you reach the thing you’ve been questing after.
Know Your Competition – Who are you competing against? The middle? The best? The status-quo? The answer should change how you approach it.
Are Successful People Just Putting in More Effort?
You Should Have More Spectacular Failures
What Should Your Goals Be?
How I Choose Projects
How to Lead an Interesting Life and Still Get Stuff Done
If You’re Young, Do Harder, Riskier Things
Is Obsession a Prerequisite for Success?
Routine is the Enemy of Good
Should You Plan to Retire
Is the Ideal Lifestyle Designed or Earned?
Ruthless Focus and the Art of Saying No
What are You Going to Be Exceptional at in 10 Years?
Don’t Swim in the Shallow Waters

On Ideas, Books and Reading

Should You Follow Less News?
Is Old Advice Better? – Is advice that comes from older traditions better? I weigh both sides of the debate.
The Power of Being Weak
Does it Matter Whether Advice is Authentic? – Why should the origin of advice impact its usefulness?
How to Pick Which Books to Read
Book Club: Tao Te Ching – My thoughts on the Eastern classic.
Book Club: Zen and the Art of Motorcycle Maintenance – The first book club, with a classic.
The Problem with Advice
Should You Know Your IQ?
Being Honest with Yourself is Hard
Are There Books You Should Re-Read Every Year?
Should You Maintain an (Almost) Empty Reading Queue?
Never Be Too Pleased With Your Past Work
Living Closer to Reality
Cynicism is Easy, Optimism Takes Guts
Here’s What’s Wrong with Self-Help
Should an Atheist Be Reading the Great Books of Religion?
Does Thinking About the Ideal Life Actually Lead to Living One?
Criticism and Praise are the Same

On Choosing What to Do

Should You Fix Weaknesses or Focus on Your Strengths? Here’s How to Decide.
Should You Desire More or Less?
How to Make Hard Life Decisions
Can You Change What You Like?
The Simple Algorithm for Making Big Life Decisions
Games Worth Playing – The most important decision you can make in life is deciding which game to play.
On Keeping Your Word
Watch Out for “Good” Ideas
Blank Slate Moments
Philosophical Tourism
What if Luck Matters More than Effort?
Day Jobs vs Side Projects
Staying in School Forever
The Obvious Choice is Often the Worst One: Why People Fail Choosing Jobs, Classes and Dates
Silencing the Background Noise of Life
If You’re So Smart, Why is Your Life Still a Mess?
Should You Wander the World or Build a Home?
Does the Ideal Life Depend on Your City?
The Pleasure of Living Within Constraints
Should Your Twenties Be for Work or Play?

On Finding Your Purpose in Life

Swimming Upstream Against Your Destiny
Losing Yourself – Maybe we don’t need to “find” ourselves when life feels adrift, but lose our notions of who we are?
We Become the Story We Tell Ourselves
World Travel or Finding Passion Won’t Escape Who You Are – You can’t run from yourself.
Don’t Know What You Want?
Feeling Lost? Stop Worrying About Your “Life Purpose”
Are Passions Discovered or Constructed?
The Power of Curiosity

On Values and Deciding What Matters

(A Little) Conformity is a Good Thing
Who Has Time for Hobbies?
What’s Your Life Strategy?
Why You Should Be More Extreme
Do You Need Self-Discipline to Have Fun? – Why having fun is more effort than it seems.
If You Had Ten Years to Learn Anything, What Would You Do?
First, See the Circle – The only way you can break out of your patterns in life is to first notice them.
Are You Trying to Be Too Original? What I Learned About the Value of Imitation From China
Be Bold, Presumptuous and Stop Caring What Others Think
The Fear of Going Soft
Things Worth Knowing, Even Poorly
Wanting the Right Things
Does Enjoyment Trump Efficiency?
Asking the Right Questions
Inconvenient Conveniences — Is Easier Always Better?
The Serious Pursuit of Fun
How to Chip Away at Your List of Necessities
You’re Going to Lose Everything Eventually
Doubt
Humility is More Important than Confidence
Average Doesn’t Mean Secure
Need Little, Want Lots
What’s Your Poverty Threshold?

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