101 Life Lessons from Kevin Kelly: Timeless Wisdom for Modern Living

Introduction: The Power of Distilled Life Experience

In an age saturated with information yet starved for genuine wisdom, Kevin Kelly’s collection of life advice stands as a beacon of practical philosophy. The legendary technology thinker and founding editor of Wired magazine has distilled decades of experience into actionable insights that transcend trends and speak to universal human experiences.

Published on his blog The Technium in April 2024 to celebrate his 73rd birthday, Kelly’s “101 Additional Advices” continues a tradition he began six years earlier—gifting wisdom to his children on each birthday. These pearls of wisdom complement his bestselling book Excellent Advice for Living, offering readers a roadmap for navigating life’s complexities with intention, grace, and authenticity.

The Complete 101 Advices: Kevin Kelly’s Wisdom

Below are all 101 pieces of advice from Kevin Kelly, presented in their original form, followed by deeper exploration of key themes:

The best way to criticize something is to make something better.
Admitting that “I don’t know” at least once a day will make you a better person.
Forget trying to decide what your life’s destiny is. That’s too grand. Instead, just figure out what you should do in the next 2 years.
Aim to be effective, but unpredictable. That is, you want to act in a way that AIs have trouble modeling or imitating. That makes you irreplaceable.
Whenever you hug someone, be the last to let go.
Don’t save up the good stuff (fancy wine, or china) for that rare occasion that will never happen; instead use them whenever you can.
The best gardening advice: find what you can grow well and grow lots and lots of it.
Never hesitate to invest in yourself—to pay for a class, a course, a new skill. These modest expenditures pay outsized dividends.
Try to define yourself by what you love and embrace, rather than what you hate and refuse.
Read a lot of history so you can understand how weird the past was; that way you will be comfortable with how weird the future will be.
To make a room luxurious, remove things, rather than add things.
Interview your parents while they are still alive. Keep asking questions while you record. You’ll learn amazing things. Or hire someone to make their story into an oral history, or documentary, or book. This will be a tremendous gift to them and to your family.
If you think someone is normal, you don’t know them very well. Normalcy is a fiction. Your job is to discover their weird genius.
When shopping for anything physical (souvenirs, furniture, books, tools, shoes, equipment), ask yourself: where will this go? Don’t buy it unless there is a place it can live. Something may need to leave in order for something else to come in.
You owe everyone a second chance, but not a third.
When someone texts you they are running late, double the time they give you. If they say they’ll be there in 5, make that 10; if 10, it’ll be 20; if 20, count on 40.
Multitasking is a myth. Don’t text while walking, running, biking or driving. Nobody will miss you if you just stop for a minute.
You can become the world’s best in something primarily by caring more about it than anyone else.
Asking “what-if?” about your past is a waste of time; asking “what-if?” about your future is tremendously productive.
Try to make the kind of art and things that will inspire others to make art and things.
Once a month take a different route home, enter your house by a different door, and sit in a different chair at dinner. No ruts.
Where you live—what city, what country—has more impact on your well being than any other factor. Where you live is one of the few things in your life you can choose and change.
Every now and then throw a memorable party. The price will be steep, but long afterwards you will remember the party, whereas you won’t remember how much is in your checking account.
Most arguments are not really about the argument, so most arguments can’t be won by arguing.
The surest way to be successful is to invent your own definition of success. Shoot your arrows first and then paint a bull’s eye around where they land. You’re the winner!
When remodeling a home interior use big pieces of cardboard to mock-up your alterations at life size. Seeing things, such as counters, at actual size will change your plans, and it is so much easier to make modifications with duct tape and scissors.
There should be at least one thing in your life you enjoy despite being no good at it. This is your play time, which will keep you young. Never apologize for it.
Changing your mind about important things is not a consequence of stupidity, but a sign of intelligence.
You have 5 minutes to act on a new idea before it disappears from your mind.
What is important is seldom urgent and what is urgent is seldom important. To get the important stuff done, avoid the demands of the urgent.
Three situations where you’ll never regret ordering too much: when you are pouring concrete, when you are choosing a battery, and when you are getting ice for a party.
The patience you need for big things, is developed by your patience with the little things.
Don’t fear failure. Fear average.
When you are stuck or overwhelmed, focus on the smallest possible thing that moves your project forward.
In a museum you need to spend at least 10 minutes with an artwork to truly see it. Aim to view 5 pieces at 10 minutes each rather than 100 at 30 seconds each.
For steady satisfaction, work on improving your worst days, rather than your best days.
Your decisions will become wiser when you consider these three words: “…and then what?” for each choice.
If possible, every room should be constructed to provide light from two sides. Rooms with light from only one side are used less often, so when you have a choice, go with light from two sides.
Never accept a work meeting until you’ve seen the agenda and know what decisions need to be made. If no decisions need to be made, skip the meeting.
You have no obligation to like everyone, and you are free to intensely dislike a person. But you owe everyone—even those you dislike—basic respect.
When you find yourself procrastinating, don’t resist. Instead lean into it. Procrastinate 100%. Try to do absolutely nothing for 5 minutes. Make it your job. You’ll fail. After 5 minutes, you’ll be ready and eager to work.
If you want to know how good a surgeon is, don’t ask other doctors. Ask the nurses.
There is a profound difference between thinking less of yourself (not useful), and thinking of yourself less (better).
Strong opinions, clearly stated, but loosely held is the recipe for an intellectual life. Always ask yourself: what would change my mind?
You can not truly become yourself, by yourself. Becoming one-of-a-kind is not a solo job. Paradoxically you need everyone else in the world to help make you unique.
If you need emergency help from a bystander, command them what to do. By giving them an assignment, you transform them from bewildered bystander to a responsible assistant.
The most common mistake we make is to do a great job on an unimportant task.
Don’t work for a company you would not invest money in, because when you are working you are investing the most valuable thing you have: your time.
Fail fast. Fail often. Fail forward. Failing is not a disgrace if you keep failing better.
Doing good is its own reward. When you do good, people will question your motive, and any good you accomplish will soon be forgotten. Do good anyway.
Best sleep aid: first, get really tired.
For every success there is a corresponding non-monetary tax of some kind. To maintain success you have to gladly pay these taxes.
Do not cling to a mistake just because you spent a lot of time making it.
For small tasks the best way to get ready is to do it immediately.
If someone is calling you to alert you to fraud, nine out of ten times they are themselves the fraudster. Hang up. Call the source yourself if concerned.
When you try to accomplish something difficult, surround yourself with friends.
You should be willing to look foolish at first, in order to look like a genius later.
Think in terms of decades, and act in terms of days.
The most selfish thing in the world you can do is to be generous. Your generosity will return you ten fold.
Discover people whom you love doing “nothing” with, and do nothing with them on a regular basis. The longer you can maintain those relationships, the longer you will live.
Forget diamonds; explore the worlds hidden in pebbles. Seek the things that everyone else ignores.
Write your own obituary, the one you’d like to have, and then everyday work towards making it true.
Avoid making any kind of important decision when you are either hungry, angry, lonely, or tired (HALT). Just halt when you are HALT.
What others want from you is mostly to be seen. Let others know you see them.
Working differently is usually more productive than working harder.
When you try something new, don’t think of it as a matter of success / failure, but as success / learning to succeed.
If you have a good “why” to live for, no “how” will stop you.
If you are out of ideas, go for a walk. A good walk empties the mind—and then refills it with new stuff.
The highest form of wealth is deciding you have enough.
Education is overly expensive. Gladly pay for it anyway, because ignorance is even more expensive.
The cheapest therapy is to spend time with people who make you laugh.
Always be radically honest, but use your honesty as a gift not as a weapon. Your honesty should benefit others.
A good sign that you are doing the kind of work you should be doing is that you enjoy the tedious parts that other people find tortuous.
Being envious is a toxin. Instead take joy in the success of others and treat their success as your gain. Celebrating the success of others costs you nothing, and increases the happiness of everyone, including you.
The more persistent you are, the more chances you get to be lucky.
To tell a good story, you must reveal a surprise; otherwise it is just a report.
Small steps matter more when you play a long game because a long horizon allows you to compound small advances into quite large achievements.
If you are more fortunate than others, build a longer table rather than a taller fence.
Many fail to finish, but many more fail to start. The hardest work in any work is to start. You can’t finish until you start, so get good at starting.
Work on your tone. Often ideas are rejected because of the tone of voice they are wrapped in. Humility covers many blemishes.
When you are right, you are learning nothing.
Very small things accumulate until they define your larger life. Carefully choose your everyday things.
It is impossible to be curious and furious at the same time, so avoid furious.
College is not about grades. No one cares what grades you got in college. College is about exploring. Just try stuff.
Weird but true: If you continually give, you will continually have.
To clean up your city, sweep your doorstep first.
Decisions like to present themselves as irreversible, like a one-way door. But most deciding points are two-way. Don’t get bogged down by decisions. You can usually back up if needed.
Every mistake is an opportunity to improvise.
You’ll never meet a very successful pessimistic person. If you want to be remarkable, get better at being optimistic.
You can’t call it charity unless no one is watching.
When you think of someone easy to despise—a tyrant, a murderer, a torturer—don’t wish them harm. Wish that they welcome orphans into their home, and share their food with the hungry. Wish them goodness, and by this compassion you will increase your own happiness.
Get good at being corrected without being offended.
The week between Christmas and New Years was invented to give you the perfect time to sharpen your kitchen knives, vacuum your car, and tidy the folders on your desktop.
There is no formula for success, but there are two formulas for failure: not trying and not persisting.
We tend to overrate the value of intelligence. You need to pair your IQ with other virtues. The most important things in life can not be attained through logic only.
If you are impressed with someone’s work, you should tell them, but even better, tell their boss.
In matters of the heart, one moment of patience can save you years of regret.
Humility is mostly about being very honest about how much you owe to luck.
Slow progress is still a million times better than no progress.
Recipe for greatness: expect much of yourself and little of others.
The very best way to win a friend is to be one.

Deep Dive: Key Themes and Applications

The Art of Self-Improvement and Personal Growth

Embrace Intellectual Humility

Kelly’s wisdom begins with a fundamental truth about personal growth: intellectual humility. He suggests that admitting you don’t know something at least once daily makes you a better person. This practice counteracts the modern tendency toward overconfidence and creates space for genuine learning.

The power of changing your mind cannot be overstated. Kelly notes that revising important beliefs is not stupidity but intelligence in action. He advocates for maintaining strong opinions clearly stated but loosely held—the recipe for an intellectual life. The key question to ask yourself regularly: what would change my mind?

Define Success on Your Own Terms

One of Kelly’s most liberating insights challenges conventional notions of achievement. Rather than chasing someone else’s definition of success, he encourages inventing your own. Paint a bull’s eye around where your arrows land, and you’re already winning. This perspective shift transforms the pressure of external expectations into the freedom of personal fulfillment.

Kelly also warns against fearing average more than failure. In a world obsessed with mediocrity disguised as excellence, this distinction matters. The goal isn’t simply avoiding mistakes—it’s avoiding settling for ordinary when you’re capable of remarkable.

The Two-Year Planning Horizon

Overwhelmed by the pressure to determine your entire life’s destiny? Kelly offers refreshing permission to think smaller. Instead of mapping out decades, focus on what you should accomplish in the next two years. This manageable timeframe balances meaningful progress with realistic planning, preventing both paralysis and short-sightedness.

The complementary advice to “think in decades, act in days” provides the fuller picture. While your vision can extend far into the future, your actions must remain grounded in what you can do today.

Relationship Wisdom: Connection and Compassion

The Currency of Being Seen

Kelly identifies a profound human need that underlies most interactions: people primarily want to be seen. When you let others know you truly see them, you give them something invaluable. This simple practice transforms relationships from transactional to meaningful.

The advice extends to physical connection through a beautiful detail: whenever you hug someone, be the last to let go. This small gesture communicates presence and care in a way words cannot.

Second Chances and Boundaries

Navigating relationships requires balancing generosity with wisdom. Kelly’s guidance is clear: you owe everyone a second chance, but not a third. This framework honors both grace and self-respect, acknowledging that redemption deserves opportunity while recognizing that patterns reveal character.

He distinguishes between different forms of respect, noting that while you have no obligation to like everyone, you owe even those you dislike basic respect. This nuanced approach maintains civility without demanding false warmth.

The People Who Keep You Alive

Perhaps the most profound relationship advice Kelly offers centers on time spent doing nothing. Discover people with whom you love doing nothing, and do nothing with them regularly. The longevity of these relationships correlates directly with your own lifespan—a reminder that the quality of our connections literally affects our health and happiness.

Professional Excellence and Career Strategy

The Irreplaceable Worker

In an age of artificial intelligence and automation, Kelly offers crucial career advice: aim to be effective but unpredictable. When you act in ways AI cannot easily model or imitate, you become irreplaceable. This doesn’t mean being chaotic—it means cultivating genuine creativity, intuition, and humanity that machines cannot replicate.

Investment in Self

Never hesitate to invest in yourself through classes, courses, and new skills. These modest expenditures pay outsized dividends. Kelly frames this as non-negotiable rather than optional, recognizing that in a rapidly changing world, continuous learning isn’t luxury—it’s necessity.

He extends this principle to employment decisions: don’t work for a company you wouldn’t invest money in. When working, you’re investing something more valuable than money—your time. Treat this investment with corresponding seriousness.

The Common Mistake

One of Kelly’s most incisive observations about professional life addresses a widespread error: doing an excellent job on an unimportant task. This trap catches even conscientious workers who conflate busyness with productivity and completion with impact.

The remedy lies in distinguishing urgent from important. What is urgent is seldom important, and what is important is seldom urgent. Getting important work done requires actively avoiding the tyranny of the urgent.

Decision-Making and Problem-Solving

The HALT Principle

Kelly introduces a powerful framework for avoiding bad decisions: never make important choices when you’re Hungry, Angry, Lonely, or Tired. The acronym HALT serves as both reminder and instruction. When you’re in any of these states, simply halt. Wait until you’re in a better condition to choose wisely.

The Three-Word Test

Before making any decision, consider three words: “and then what?” This simple question cascades consequences into view, revealing implications that might otherwise remain hidden until too late. Applied consistently, this practice transforms reactive decision-making into strategic thinking.

Embracing Reversibility

Many decisions present themselves as irreversible one-way doors, but Kelly notes that most are actually two-way. You can usually reverse course if needed. This recognition prevents decision paralysis and encourages experimentation. The fear of making wrong choices diminishes when you understand that few choices are truly permanent.

Creative Work and Innovation

Beyond Conventional Excellence

Kelly challenges creators to think beyond personal achievement. Try to make the kind of art and things that will inspire others to make art and things. This multiplicative approach to creativity focuses on ignition rather than merely illumination—your work becomes most valuable when it sparks others’ creative fires.

The companion insight about becoming world-class addresses path selection: you can become the best in something primarily by caring more about it than anyone else. Passion, not just talent, determines mastery.

Starting and Finishing

Many fail to finish, Kelly observes, but many more fail to start. The hardest work in any work is starting. You can’t finish until you start, so get good at starting. This reframes procrastination not as a finishing problem but as a starting problem.

When you find yourself procrastinating, Kelly offers counterintuitive advice: don’t resist—lean into it. Procrastinate 100%. Try to do absolutely nothing for five minutes. Make it your job. You’ll fail, and after five minutes you’ll be ready and eager to work.

The Five-Minute Rule

Innovation operates on strict timelines. You have five minutes to act on a new idea before it disappears from your mind. This urgency demands readiness to capture inspiration through whatever system works—notes, recordings, sketches. Ideas are perishable goods requiring immediate handling.

Daily Practices and Life Habits

Breaking Routines

To prevent life from becoming a rut, Kelly prescribes regular pattern interruption. Once monthly, take a different route home, enter your house by a different door, and sit in a different chair at dinner. These small variations keep perception fresh and prevent the autopilot living that drains vitality from everyday experience.

The Luxury of Subtraction

Want to make a room luxurious? Remove things rather than add things. This minimalist principle applies beyond interior design to life itself. Abundance often comes through subtraction, not accumulation. What you eliminate matters as much as what you keep.

Kelly extends this to material possessions with practical advice: when shopping for anything physical, ask where it will go. Don’t buy unless there’s a place for it to live. Something may need to leave for something else to arrive.

Using the Good Stuff

Don’t save fancy wine or china for rare occasions that will never happen. Use them whenever you can. This permission to enjoy quality in ordinary moments combats the scarcity mindset that reserves joy for hypothetical futures. Life is happening now—bring out the good stuff.

Wisdom for Difficult Times

Compassionate Thinking

When confronting people easy to despise—tyrants, murderers, torturers—Kelly offers radical advice: don’t wish them harm. Instead, wish that they welcome orphans into their homes and share food with the hungry. Wish them goodness, and through this compassion you will increase your own happiness.

This practice doesn’t excuse wrongdoing or abandon justice. Rather, it protects your own heart from the toxin of hatred while maintaining moral clarity.

Steady Satisfaction

For steady satisfaction, Kelly recommends working on improving your worst days rather than your best days. Peak experiences, while wonderful, don’t determine quality of life as much as the baseline. Raising the floor matters more than raising the ceiling.

The Patience Connection

Patience for big things develops through patience with little things. This recognition transforms daily irritations from mere annoyances into training opportunities. Every minor frustration becomes a chance to build the capacity you’ll need for major challenges.

Knowledge, Learning, and Understanding

Historical Perspective

Read lots of history so you understand how weird the past was, Kelly advises. When you grasp past weirdness, you’ll be comfortable with how weird the future will be. This temporal perspective inoculates against the shock of change by demonstrating that strangeness is humanity’s constant companion.

The Museum Test

In museums, spend at least ten minutes with an artwork to truly see it. Aim to view five pieces at ten minutes each rather than 100 at 30 seconds each. This principle of depth over breadth applies beyond art appreciation to learning generally. Superficial exposure to many things develops less understanding than sustained attention to fewer things.

College as Exploration

College is not about grades, Kelly insists—no one cares what grades you got. College is about exploring. Just try stuff. This liberating perspective recasts higher education as laboratory rather than credential factory, valuing experimentation over optimization.

Money, Wealth, and Generosity

The Highest Form of Wealth

Kelly identifies the highest form of wealth: deciding you have enough. This internal shift from perpetual wanting to grateful sufficiency creates a security that accumulation alone can never provide. The goalpost stops moving when you plant it yourself.

Generosity as Selfishness

The most selfish thing you can do is be generous, because your generosity will return tenfold. Kelly reframes giving not as sacrifice but as investment, recognizing that what we offer others enriches us more than hoarding ever could.

This connects to his architectural metaphor: if you are more fortunate than others, build a longer table rather than a taller fence. Inclusion creates abundance; exclusion creates scarcity even in the midst of plenty.

The Tax of Success

For every success, there’s a corresponding non-monetary tax of some kind. To maintain success, you must gladly pay these taxes. This recognition prevents resentment at the hidden costs of achievement—the scrutiny, the responsibilities, the expectations—and reframes them as acceptable prices for valuable goods.

Communication and Expression

Criticism Through Creation

The best way to criticize something is to make something better. This transforms critique from destructive to generative, from commentary to contribution. Rather than merely pointing out problems, create solutions.

Tone Matters

Work on your tone, Kelly advises, because ideas are often rejected due to the tone of voice they’re wrapped in. Humility covers many blemishes. The most brilliant insight delivered arrogantly lands worse than a modest insight shared with grace.

Storytelling Essentials

To tell a good story, you must reveal a surprise—otherwise it’s just a report. This distinction between narrative and data delivery matters in every form of communication. Information informs, but surprise engages and transforms.

Practical Life Skills

The Concrete Test

When pouring concrete, choosing a battery, or getting ice for a party, you’ll never regret ordering too much. Kelly’s specific scenarios illustrate the general principle: for certain resources where shortage creates problems but surplus doesn’t, err on the side of abundance.

Evaluating Surgeons

If you want to know how good a surgeon is, don’t ask other doctors—ask the nurses. This applies beyond medicine: those who work closely with an expert daily often provide better assessments than peers who interact occasionally.

Fraud Detection

If someone calls alerting you to fraud, nine times out of ten they are the fraudster. Hang up and call the source yourself if concerned. This simple rule protects against a common scam while acknowledging that legitimate warnings occasionally occur.

Mindset and Perspective

Curiosity vs. Fury

It’s impossible to be curious and furious at the same time, so avoid furious. This mutual exclusivity makes curiosity a powerful antidote to anger. When rage threatens, pivot to questions.

The Learning Indicator

When you are right, you are learning nothing. This reframes correctness from victory to missed opportunity, encouraging you to seek situations where you might be wrong because those are precisely the circumstances that enable growth.

Optimism and Success

You’ll never meet a very successful pessimistic person. To be remarkable, get better at being optimistic. Kelly doesn’t suggest naive positivity but rather notes that pessimism creates self-fulfilling prophecies of limitation while optimism opens possibility.

Work Methodology

Focus on the Smallest Thing

When stuck or overwhelmed, focus on the smallest possible thing that moves your project forward. This breaks paralysis by making the next step so obvious and achievable that resistance crumbles. Momentum builds from minute movements.

Working Differently vs. Working Harder

Working differently is usually more productive than working harder. This challenges hustle culture’s assumption that effort alone determines outcomes. Often the path to better results runs through smarter approaches rather than longer hours.

The Tedious Parts Test

A good sign you’re doing the right kind of work: you enjoy the tedious parts that others find torturous. When drudgery feels satisfying, you’ve found your calling. This provides a more reliable indicator than excitement, which can mislead.

Legacy and Long-Term Thinking

Writing Your Obituary

Write your own obituary—the one you’d like to have—and then work every day toward making it true. This practice clarifies values and priorities, transforming vague aspirations into concrete direction.

Interviewing Your Parents

Interview your parents while they’re still alive. Keep asking questions while you record. You’ll learn amazing things. Or hire someone to create an oral history, documentary, or book. This will be a tremendous gift to them and your family.

The window for capturing these stories closes permanently. The opportunity feels infinite until suddenly it isn’t.

Small Things and Large Lives

The Accumulation Principle

Very small things accumulate until they define your larger life. Carefully choose your everyday things. This recognition empowers daily choices with significance while warning against the creeping mediocrity of unconsidered routines.

The Compound Effect

Small steps matter more when you play a long game because a long horizon allows you to compound small advances into quite large achievements. This mathematical truth applies to relationships, skills, wealth, and character.

Conclusion: Living the Examined Life

Kevin Kelly’s 101 pieces of advice form a cohesive philosophy of intentional living grounded in decades of observation and experience. These aren’t abstract principles but battle-tested practices that emerge from actual engagement with life’s challenges and opportunities.

What makes Kelly’s wisdom particularly valuable in 2024 is its timelessness paired with relevance. He addresses both perennial human concerns—relationships, meaning, work—and contemporary challenges like AI’s impact on careers and the information age’s assault on attention.

The advice resists categorization into simple themes because life resists such categorization. Instead, Kelly offers a mosaic of insights that readers can assemble according to their own needs and circumstances. Some pieces will resonate immediately while others await their moment of relevance.

Perhaps the meta-lesson underlying all 101 pieces is this: wisdom comes not from knowing all the answers but from asking better questions, remaining open to surprise, and treating each day as an opportunity to practice what matters. Kelly models a life lived with curiosity, generosity, and attention—qualities available to anyone regardless of circumstances.

As you navigate your own path, these pieces of advice serve as landmarks rather than maps, offering orientation without dictating direction. Take what resonates, set aside what doesn’t, and return periodically as your life evolves. The best advice changes meaning as you change, revealing new layers with experience.

Kelly’s tradition of sharing birthday wisdom reminds us that accumulating years means little unless we also accumulate insight. The goal isn’t merely to live longer but to live better—more consciously, more generously, more fully. That possibility remains available every day, starting now.

Source: Kelly, K. (2024, April 18). 101 Additional Advices. The Technium. https://kk.org/thetechnium/101-additional-advices/

About Kevin Kelly: Kevin Kelly is the founding executive editor of Wired magazine and the author of several influential books including The Inevitable, What Technology Wants, and Excellent Advice for Living. His blog, The Technium, explores the intersection of technology, philosophy, and culture.

Related Reading: For 460 additional pieces of advice, see Kelly’s book Excellent Advice for Living: Wisdom I Wish I’d Known Earlier. His previous collections include “68 Bits of Unsolicited Advice” and other birthday wisdom posts on The Technium.