30 Life Lessons To Get You Through Your Twenties

These are the principals not only to remember, but to apply everyday.

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A mentor once told me, “Your twenties are for learning. Your thirties are for taking action.” It’s funny I remember that now, the day I turn 30 years old.

Reaching this age has been a humbling reminder of how long and short life really is. I’m lucky to have made it this far, yet there’s still so much ahead.

When we reach a “milestone birthday” there’s only so much time for reflection before we have to ask, “What do I want the next 5, 10, or even 30 years to look like?”

I made it a habit throughout my twenties to write down any quotes or pieces of advice I came across that seemed valuable. Some are quotes I wrote down years ago but am only beginning to understand now. There are others I wish someone had told me when I turned twenty.

One of my favorite books is Meditations, by Marcus Aurelius. Besides the overwhelming amount of actionable wisdom it contains, I love the idea that the Emperor of Rome (the most powerful man on Earth at the time) sat down each night to write advice to himself on how to be a good person.

As you read these quotes and principals, it might feel like I’m preaching. But I can assure you that the reason these quotes made it into my notebook is that they’re the concepts I needed the most help with. Like Marcus Aurelius, I wrote these down as reminders for myself.

This year, I hope to not only remember these principles but to better apply them to my life. Because regardless of age, that’s what matters most: taking action.


1 “The first principle is that you must not fool yourself and you are the easiest to fool.” Richard Feynman

We all smoke our own crack sometimes. It’s easier to embrace facts that support what we already believe, or want to believe. Past experience, biases, and our patterns for seeing the world affect our instincts — often leading us away from the truth.

Is what you’re working towards actually important, or does it feel that way because you’ve been chasing it for so long? It’s often necessary to be our own devil’s advocate.

2 “He who indulges empty fears earns himself real fears.” -Seneca

Have you ever had a small doubt float into your mind and felt the storyboards in light up? We project doomsday scenarios on ourselves and worry most about what could happen. When I think about what stressed me out most in my twenties, I realize I suffered much more in mind than in reality. Mark Twain has his own great version of this idea, “I am an old man who has known many great troubles, but most of them never happened.”

3 “Don’t be a hero, be consistent.” paraphrased from multiple sources

Heroics are the great killer of goals worth accomplishing. People who haven’t exercised in years make heroic declarations like, “I’m going to the gym everyday day until I lose 50lbs.” Nonsense. That’s not a sustainable plan.

The good plan you stick with is better than the perfect plan you quit halfway through. Setting aside two hours in the morning to write has yielded far more pages than trying to schedule out large, heroic blocks of time in my day. Don’t be a hero. Do what little you can, when you can. It’s that simple.

4 “The opposite of work isn’t play. It’s depression.” -Brian Sutton-Smith

I’ve written about the importance of play before, as it’s one of the things I need the most reminding. Goals, list, doing, doing, doing… The constant chasing of accomplishment is a slippery slope that takes us away from the joy of just being. I think of this quote and tell myself, “Just relax man.”

5 “Never attribute to malice that which can be adequately explained by stupidity.” -Robert J. Hanlon

There are more stupid people than evil people in the world and, most of the time, you’re going to have run-ins with the former. I’ve wasted so much energy feeling angry at people I thought were going out of their way to “do me wrong.” In reality, most were unaware, uneducated, and living inside their own bubble.

“How could they think that?” They didn’t. They didn’t think at all.

6 “The best art divides the audience.” -Rick Rubin

I keep this in mind whenever I peck out a sentence that might piss certain people off. You know you’re onto something when you can generate real excitement or outrage from our one side of the audience instead of lukewarm acceptance from all. This is a reminder for all creatives to take risks. Churchill said, “You have enemies? Good. That means you’ve stood up for something sometime in your life.”

7 “Are you hunting antelope or field mice?” paraphrased from Newt Gingrich

I fall into the trap of mistaking busyness for productivity almost by default. “Should I start writing? Well, I should probably re-organize the kitchen first.” Finishing a thousand unimportant tasks doesn’t mean you had a productive day. Knowing where to allocate time and focus has only become more important in my life and I’ve had to learn the hardest way (paying with time) what’s worth hunting.

Hemingway wrote, “Never mistake motion for action.”

8 “You’re the average of the five people you spend the most time with.” Paraphrased from multiple sources.

This advice goes beyond people. We become the average of the five things we think about the most; the five habits we fall into. Music, books, television — it all goes in and leaves its mark. Austin Kleon writes, “You are, in fact, a mashup of what you choose to let into your life.”

9 “Move towards your mountain.” -Neil Gaiman

Having a mountain — a long-term target — to climb towards helps guide all the small decisions we have to make along the way. It’s so easy to get caught in short-term thinking when creating the life you want. Having a peak to visualize helps to recognize shiny distraction for what they are.

When forks in the road come along ask yourself, “Which choice brings me closer to my mountain?”

10 “People are frugal in guarding their personal property; but as soon as it comes to squandering time they are most wasteful of the one thing in which it is right to be stingy.” -Seneca

Opportunity breeds more opportunity. The closer we get to our mountain, the more protective we must be with our time. Learning when to say “no” to things you would have once jumped at becomes just as important as having the opportunity in the first place. Money comes and goes, but time is a non-renewable.

On a heavier note, I feel like this is the best place to point out that you’re going to die. Yes, you. I don’t write this to be morbid, but to give you an invigorating reminder to not waste time on what is trivial.

11 “Do not speak unless you can improve the silence.” -Zen quote

As someone who suffers from chronic foot-in-mouth disease, I should have this written on my arm. Many things can and should be left unsaid. One of the best writing tips I ever received was, “Omit useless words.” We could do well by remembering this advice for the page and real-life conversations. Afterall, “Brevity is the soul of wit.”

12 “Principals are good only once they become deeds.” -Van Gogh

Knowledge is not power. It is only potential. Put another way by Tony Robbins, “What you know doesn’t mean shit. What do you do consistently?”

13 “Simplicity is the ultimate sophistication.” -Leonardo da Vinci

As more and more options and decisions crowd my life, the more I’ve grown to appreciate simplicity. Decision fatigue is real. Bells and whistles distract. If the rise of minimalism has taught us anything it’s that an entire generation is coming around to the idea that less is more.

14 “Discipline Equals Freedom” — Jocko Willink

Ask anyone what they want more of in life and “money” and “time” will top the list. But dig deeper and you’ll find that all answers can be stripped down to wanting more freedom. The amount of discipline we have over our thoughts and actions is an enormous indicator of our future freedom. It’s the difference between the life you want or a life strung together by moments of caving to temporary urges. One of my favorite lines from Epictetus, “No man is free who is not master over himself.”

15 “In dreams, the truth is learned that all good works are done in the absence of caress.” -Leonard Cohen

Think long and hard. But once you’re stuck, walk away. Hemingway also gave the advice that a writer should stop for the day, “before the well was empty.” When we take our attention away from a problem we want to solve, our subconscious continues to work. Loosen your grip and feel the answers rise to the surface.

16 “It’s easier to act your way into a new way of thinking than think your way into a new way of acting.” -Jerry Sternin”

All the inspiration, positive thinking, and perfect strategy mean nothing without action. There‘s too many waiting around for floods of positivity like superstitious villagers doing a rain dance when they should be digging a well.

Inspiration follows action.

Don’t be the person who says, “I’m thinking of starting this.” Just show us what you started.

17 “What gets measured gets managed.” -Peter Drucker

This old quote has been thrown around for so long I’d always thought of it as just another cliche. But like most cliches, it got that way by being true. If you want to speed up growth in any area, start measuring your progress. It’s strange how effective this is for just about everything.

18 “Learn from the mistakes of others. You don’t have time to make them all on your own.” -Eleanor Roosevelt

We love to talk about how failure is some magical rainbow bridge to success. Yes, we can and must learn from our failures, but it’s more than worthwhile to avoid them when possible. No matter what obstacles you’re facing, someone else has been there before. The best part? They documented it. Study those throughout history who have been where you’re headed. Let their pitfalls be your warning signs.

19 “Whenever you find yourself on the side of the majority it’s time to pause and reflect.” -Mark Twain

The general consensus on most topics should be continually challenged. As Eric Weinstein puts it, “[Consensus] is how we bully people into pretending that there’s nothing to see. ‘Move along people’”.

Questioning the majority doesn’t mean you disagree. In a world where hasty opinions presented as facts spread like wildfire, the ability to think like a contrarian is a good tool to have sharp and ready.

Peter Thiel challenge us to ask ourselves, “Have my universal truths been steeped in so much time that I don’t remember ever considering the opposite?”

20 “People often overestimate what they can accomplish in one year and underestimate what they can do in five.” -Peter Drucker

The reason most New Year’s resolutions fail is that they are egotistically lofty and unrealistic. Most things worth doing take much longer than one year.

I’m blown away by how many people I meet who refuse to have some degree of a five-year plan. They say, “I can’t think that far ahead because five years ago I was a completely different person.” Chances are you weren’t that different, you’ve just learned more about yourself since then. Having a five-year plan doesn’t mean you can’t change course, but it does force you to think long-term and play the long game.

Don’t know where you want to be in five years? You should start thinking.

21 “The struggle ends when the gratitude begins.” -Neale Donald Walsch

Ahh, gratitude… The closest thing to a magic bullet I’ve found in curing a bad mood. It’s silly how quickly my darkness clears up when I take a few moments to write down a few things I’m grateful for.

I want to point out that having a general sense of gratitude isn’t enough. Just as having the “spirit of giving” doesn’t count unless you, ya know, actually give, you have to be actively grateful to reap the benefits.

22 “A solid routine fosters a well-worn groove for one’s mental energies and helps stave off the tyranny of moods.” -Mason Currey

This comes back to the power of thinking less and doing more. Having routines, or rituals are the best way to take the guesswork out of your day. All the greats had some form of routine in place to produce work and keep (somewhat) sane. We all have rituals in place now. Find the ones that move you forward and protect them.

23 “Money is a good servant and a bad master.” -Francis Bacon

Regardless of how important money is to you, the last thing you want is to end up being a slave to it. Anyone — rich or poor — can fall into the trap of allowing money to be what steers their decisions. Money is a tool for achieving the level of freedom and security you want for yourself and your family.

24 “A man can free his soul only by exhausting his body.” -Rich Cohen

It may seem barbaric, but picking heavy things up only to put them right back down clears the cobwebs of my mind like nothing else. Meditation, self-control, positive thinking — they all have their place. But if you see me pacing around lethargic and anxious, just send me to the gym.

25 “The test of a first-rate intelligence is the ability to hold two opposing ideas in mind.” -F. Scott Fitzgerald

Few things are black and white. And anything worth debating has truths in each side. The ability to see valid points on the other side of an argument is the best way to ultimately make a case against those points. We don’t gain traction in bringing people around to our way of thinking by shutting down their views. This skill is becoming rarer and frighteningly important every day.

26 “Life is simple. It’s either work or it’s bullshit.” -Ernest Hemingway

This might seem to counter the importance of play, but to me, this quote is a reminder that there’s more to life than chasing happiness. The word happiness itself is problematic because its definition is ever changing and relies on internal feelings. I believe in making a stronger distinction between satisfaction and happiness.

Spending time with my loved ones makes me happy. But finishing an article — setting an idea in motion and watching it materialize — gives me satisfaction.

I don’t think it’s all “work or bullshit,” but I don’t think the feeling of accomplishment should have to piggyback off the vague definition of happiness.

27 “Fortune favors the prepared mind.” -Louis Pasteur

Recently, I’ve had opportunities come to me that a few years ago, I’d only dreamed of. I’ve caught myself thinking, “It’s about time.” But had these things come to me sooner would I have been ready? Probably not.

Put another way, “When the student is ready, the master will appear.” Don’t wait until you get that promotion to learn how to lead. Learn how to write before you get your big idea for a book. When opportunity knocks, have the tools to answer.

28 “We make a living by what we get, but we make a life by what we give.” -Winston Churchill

The best advice for moving up in the world is what you already know to be true: Add value, add value, add value. Stop worrying about your “fair share” or what you think you “deserve.” The advice from people who are considered “successful” is unanimous: “The more you give, the more comes back to you.”

29 “You can have anything you want, just not everything you want.” -Susan R. Fussell

One of my favorite scenes in Mad Men is where Don Draper has to explain to a client why his advertising tagline can’t be, “Where pros go and everyone is welcome.” Don tells him, “That’s not a strategy, that’s two strategies connected by the word ‘and’.”

All too often, trying to get everything leads to having nothing. Choose a path, and be honest with yourself about what it comes with. You can become a renowned classical musician, but you probably won’t be mobbed in the streets by thousands of screaming fans. That type of acclaim is for pop stars. If you want to spend the next ten years building multimillion-dollar businesses, you probably aren’t going to also have a nice relaxed, stress-free work life.

30 “Waste no more time arguing what a good man should be. Be one.” -Marcus Aurelius

My favorite quote on the list and the perfect place to end. Please replace “man” with “person” if that helps you. Deep down we all know what it means to do right by others and ourselves. Stop planning, stop considering — just start. Take care of yourself. Take care of others. There’s nothing left to ponder


There is it. That is in no way a complete list of everything you need to know, but it should be enough to hold you over until next year.

If you have a quote, mantra, or other words to live by that I missed, please share it with me below. 

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