101 Short Lessons on Writing, Creativity, and Generating Ideas
Everything I learned from my first 12 months of being an online writer
Exactly one year ago I started writing my first book. It was called “Ten Mentors,” a collection of lessons I learned from interviewing the tope ten Russian entrepreneurs. I knew exactly nothing about writing.
Today, I know 1% more.
Over the past 12 months, I started writing on Medium, wrote three English ebooks, and read more than 50 books on creativity. It’s been a real whirlwind. And I know it’s only the beginning.
Here’s everything I wish I knew when I just started out.
1. You Are an Artist
Even if you don’t think you are. Even if society told you you are not. If there is a story of you doing something brave, searching for the right answer on your own, or speaking when others are quiet, then you are an artist.
A blog is an art. And so is life.
2. Write (Create) Every Day, but Publish When Ready
Don’t force yourself to hit “publish” for the sake of productivity. You’re not paid to type. You are paid to create something meaningful. Trust your feelings and keep working until you feel content about your piece.
3. You Are Not the One Creating Your Art
Your daimon (genius) is. So don’t blame yourself for failure, and don’t take all the credit. Just keep showing up for your part of the job. Elizabeth Gilbert talked about this in her 2005 TED talk.
4. Leave Only What’s Surprising
Get rid of almost everything else. Make every word count. Cut out everything that’s now creating the wow effect or changes the life of your audience for the better.
5. Your Only Job Is to Show Up
Woody Allen said that 80% of success is “showing up.” If you want to write a novel, don’t just dream about it — show up in the morning to write.
It’s up to you, as a content creator, to define what “showing up” is for you. But once you’ve defined it, show up.
6. Don’t create for the market, create for yourself
There is no “market.” Or there are infinite markets. Which is to say, don’t overthink it. Make for the audience of one. If you like your work, somebody else will too. The starving artist problem is not a problem in the world where you can pick any audience you like.
7. Pick an Audience
And create only for them. Show up for your audience. You can play around with different types of content, but your audience should be intact. Don’t go for everybody, you’ll just end up serving nobody. Go niche. Go narrow. Go specific.
8. The best time to promote your book/song/project/business
Was three years ago. Three years to build a reputation. Three years to build trust. Three years to gain credibility.
9. Art Is a Verb
It’s an act of courage. It’s what you do when you risk saying something that might be ridiculed. Anything that’s scary to publish is art. Anything that’s safe is a job.
10. (Good) Artists Are Rich
You can sell a piece of painting for $150,000. If your art is good, and you know how to position yourself, you will be rewarded. And yet, art is not created for the money. It contradicts the definition of art. When a transaction occurs, it ceases to be art.
Why do you create art?
11. You Create Art to Discover Yourself
Not to express yourself. But to discover and understand who it is that you are.
12. Be an Essentialist Writer
Pick one platform and focus on it. Use other platforms for distribution. Instead of trying to get everyone and everywhere, respect the audience and the exposure you’ve already got. If you look at most successful creatives (Casey Neistat, Tim Ferriss, Shane Parrish) they weren’t spreading themselves thin. They focused.
13. Understand There’s an Enemy
It’s called Resistance. And it’s aiming to destroy you. Read Steven Pressfield’s “War of Art” on it. Your job as a creative is to battle that monster every day anew. It never ends.
14. Stick to It
There are two types of quitting: the good and the bad. When you quit because it’s hard, it’s bad quitting. When you quit because there’s nowhere else to go, that’s good quitting. Know the difference and don’t quit when it gets hard.
You might save yourself stress right now by switching to a new project, but it will get hard again. There will be, what Seth Godin calls, “the dip.”
15. Build Trust, Not Followers
The rarest commodity in the 21st century is not attention. It’s trust. Build trust by showing” up each day with something valuable to say. Do your part of the job. Become better at what you do, and create more for your audience. Keep your promises. It’s just like in real life.
16. Make something you’d want to read/listen/watch yourself
The best way to vet ideas for blog posts is to write something for yourself. The best way to vet ideas for books? Write blog posts.
17. Mind the Gap
Ira Glass talks of the “gap” that all creatives face in the beginning. It’s the gap between your taste (which is killer and what got you in the game in the first place) and your current abilities. You bridge that gap by doing a lot of work.
18. Consume More Than You Create
There are people who urge you to stop being a “consumer” and become a “producer” instead. Don’t listen to them. The quality of art that you produce is directly correlated with the quality of art that you consume.
When I read crappy social media posts, all I created was crappy social media posts. Now I read books. Lots of books. Fiction, non-fiction, philosophy. And I try to emulate my favorite authors. To create high-quality art, consume high-quality art.
19. It’s All About Them
It’s all about the reader. It’s all about what they think. It’s all about what they get from an interaction with you.
20. Give More Than You Take
The connection economy is great. It allows us to ditch the dog-eat-dog world and have win-win scenarios everywhere. But too few people realize this. They still take (or look to take) more than they provide. At the end of the day, it’s the creator who gives the most who wins (see rule 19).
Focus on the giving, and the taking will take care of itself.
21. Don’t Read Comments
Instead, urge people to message you directly. Comments are half-public, half-personal screams for attention. People who write comments don’t think. And they can hurt. So don’t read comments, but build a more direct and honest relationship with your audience.
22. “Write Drunk, Edit Sober”
I am not urging you to become Hemingway and start drinking at 12 o’clock. No. I am saying, write today, when you’re most passionate. And edit later. Tomorrow.
23. Write First, Edit Second
You have two modes as an artist. The writer (or any other creator). And the editor. Those are two very different modes. Your brain works differently. Never do both at the same time. That’s how you invite the “block” into the game.
24. Promote Your Work
You might think that your job as creative ends after you hit “publish.” No. It’s just the beginning. Read Ryan Holiday’s Perennial Seller. Promoting your work is your job as a creator.
25. Build a Skill, but Then Stop
Too many people focus on skills. While skill is important, you won’t create art on skill alone. Learn how to write by being prolific, but at one point stop. And focus on substance, on content, on meaning.
26. Art Is Like Wine
It gets better with time. If you’re in your twenties, realize that your best work is still decades ahead of you.
27. Create Every Day
It doesn’t matter what you do, just make something every day. The best way to create and produce something consistently is to make a habit. Stephen King writes 2,000 words every day. On his birthday. And on the Fourth of July.
Speaking of Stephen King…
28. Stephen King’s Pencil Is a Myth
Don’t overdo with tactics, habits, advice, and routines you find in other writers. Writing with Stephen King’s pencil won’t turn you into Stephen King.
29. To Create Better, Live Better
Your art reflects who you are. To make better art, try becoming a better human being. Read better books. Say better things. Surround yourself with better people. Let it happen organically. But make it happen.
30. “Who Are You Serving?”
As an artist, you are serving your idea. And your audience. “Who are you serving?” That’s the most important question. And then, “What can’t they miss?” Answer these two, and you won’t ever run out of ideas.
31. You Don’t Have to Create Original Work
As they say, “real artists steal.” But don’t simply steal. Take ideas of others, repackage them, and turn into a more digestible, easy-to-understand format.
Just look at Tim Ferriss.
32. “Do Only What You Can Do…
…keep redefining what that is until it’s true.” — Naval Ravikant.
33. “Writer’s Block” Is a Myth
It comes from having too high expectations from yourself.
Remember. There was no writer’s block before the Renaissance. People used to come home, sit down, and write. Don’t be hard on yourself. Just do your part of the job.
34. People don’t read you because you’re smart
People read you because you went the extra mile. Because you’re passionate about the topic. Because you tell a story. Because you’re honest. Brave. And because you did the hard work for them. The more you do that, the more people will read you.
35. Be Like Google
Google itself knows nothing. It points fingers to other people and gives them all the credit. And yet, people read it all the time.
Give all the credit to others all the time. Readers will trust you more.
36. Cut Out 30%
Stephen King said, “Kill your darlings.” Usually, the intro and the conclusion aren’t necessary. Instead of saying what you’re going to say, and then ending by saying what you just said, just say it. People don’t have time for bullshit.
37. There Are Two Types of Writers
Writers who need to outline everything and then write. And writers who need to enter the “flow” mode first, and edit second. Know what type you are. If you confuse your type, you’ll end up creating shit. This is from experience.
38. What Got You Here Won’t Get You There
Meaning, if you published daily to get to this number of subscribers, good job! But that doesn’t mean that you should continue at the same pace. Creative success is not linear. To go from zero to 1,000, you might have needed quantity. But now it’s time to start focusing on quality.
Less, but better.
39. The Golden Medium
Humor itself is pretty niche. So is intellectual work. But combine informative with funny, and you get golden. Think about TED talks. They are inspiring, thought-provoking, but also funny. Humor is life. Add more life to your work. Add more humor.
40. The Law of Physics Didn’t Change
Patreon is great. It allows creatives to get paid for doing creative work. Medium is great. It allows writers whom nobody knows to get exposure. And yet, the laws of physics don’t change. These platforms only made it easier for your work to get seen. But if your content is bad, nobody will read/watch/listen to it. Which is to say…
41. Focus on Quality
Make quality your number one priority. And to do that, think long-term. Think not days, weeks, months, but years. Decades. What you’re doing now is (hopefully) your life’s work. Make it great. Invest the effort into making each piece absolutely fantastic. Set the bar high and people will come.
42. Have Deadlines
But don’t be too much of a perfectionist. When the authors of Re:Work were asked how to ship projects on time and budget, they said,
“It’s easy. Whenever you run out of either, ship.”
Set yourself deadlines. Make them work for you. It doesn’t matter whether it’s daily, weekly, bi-weekly, or monthly. Ship your content once the bell rings.
43. You Cannot Fix the Perfection of a Blank Page
You can fix anything, Neil Gaiman said. You can edit, you can cut, you can even trash the project altogether. What you can’t edit or fix is the perfection of a blank page. So go write something.
44. Can’t Write Well? That’s Fine
Write poorly. Write something. Just write. And then gradually, become better. And then write some more. Just don’t stop by thinking you’re not good enough. Nobody was when they started out.
People may be born with an inclination towards something, which we often call “talent”, but nobody is born with the skill. Skill is acquired through work.
45. Internalize Your Goals
The Stoics had a great way of coping with the world they don’t understand. They internalized their goals. They focused only on what they could control, their effort, and let go of anything else. You cannot control the result. You cannot control the reaction of your audience. The only thing you can control is whether you’ve put enough effort, energy, resources into what you’re doing. Focus on that.
46. Be a Specialist First
Making money from creating content is hard. So don’t start with it. Start with freelance. Make money. And work on your art part-time.
I know that people say to follow your dreams, but be practical too. Feed yourself. Making $1,000 on freelance is so much easier than through content, especially if you’re just starting out. Seth Godin became Seth Godin and is trusted on so many topics because he was a specialist for so long. He wrote 19 books on marketing.
Earn your right to be a generalist.
47. How Much Is Enough?
Know your number. Is it $30,000 per year? $60,000? $100,000? The smaller this number is, the easier it is to get to it. Once you know how much is enough, you can build a strategy around getting there. You’ll know when you “succeeded.”
48. Success Is…
…finding yourself.
It’s not in the numbers. Not net worth. Not status. Or prestige. It’s figuring out who you are and being that person. Strive to be like Freddie Mercury’s character in Bohemian Rhapsody when he said, “I am exactly the man I was supposed to be.” Feel your way through life until something fits.
49. If Your Writing Isn’t Useful, Don’t Publish It
Paul Graham, the founder of YCombinator, quotes his friend’s technique.
“I learned it from my friend Robert Morris, who has a horror of saying anything dumb. His trick is not to say anything unless he’s sure it’s worth hearing. This makes it hard to get opinions out of him, but when you do, they’re usually right.”
What writing is useful? According to Paul, it’s writing that tells people something true and important that they didn’t already know and tells them as unequivocally as possible.
Novelty. Precision. Importance. Surprise.
It doesn’t always have to be something readers (or most readers) don’t already know though. It may be something they unconsciously knew for a long time, but couldn’t express in words. Oftentimes this is the best type of writing.
50. Who Leaves Bad Comments
In my experience, whenever I get bad comments, it’s not because the person doesn’t like me. It’s because they didn’t understand what I truly meant. And when I then go on to explain what I meant in more detail, they usually understand.
It’s almost impossible to write so that everybody understands — no matter how good you are at writing. But it’s worth trying.
51. Get Rid of Useless Words
If something can be said shorter, say it shorter. There’s too much content. Get straight to the point.
Whenever someone asks you a question, you don’t go, “Here’s what I want to say,” you answer immediately. In writing, filmmaking, podcasting, any type of content your create, cut straight to the chase. Say what you want to say. And move on.
52. The Essay Is the Best Form of Non-Fiction Writing
But not the essays you were meant to write in school, with introductory paragraphs, supporting arguments and conclusions. No.
The real essays. The ones that demonstrate your chain of thought. The ones you use to make an attempt to answer something you don’t (yet) know. The essays that Seneca, Montaigne, and Paul Graham wrote.
53. Slow and Steady Wins the Race
You start a piece or a book with an idea. And after putting in the effort each day, over many days, you end up writing a novel or a great piece of writing. I took 20 days to write this, five points per day.
54. You Are Not a Journalist
Probably.
There are no deadlines. Have ones for yourself, to avoid excessive perfectionism, but take all the time you need to make your art perfect.
55. Don’t Quit Your Day Job
As Seth Godin said, trying to make money from writing books is a path to disappointment. But that doesn’t mean you shouldn’t write them.
It’s good to have something else besides your art pay your bills. That way you avoid sabotaging your art by writing for the money. You also have something to write about. Kafka, Dickens, and many others had full-time jobs all their lives.
56. Respect Your “Daimon”
That force of potential that lives inside you. It’s the same force that lives inside a little acorn — that turns it into a mighty oak within the right conditions. You can’t run away from your artistic calling. Read Steven Pressfield’s “The Artist’s Journey.”
57. How to Find the Best Ideas to Write About
Think of yourself as a proxy for the reader. What can’t you stop thinking about? Is there anything surprising you didn’t know before? Share that. Only publish what’s surprising and what the reader didn’t already know.
P.S. Also, try Quora. Use the questions there for inspiration for future posts.
58. Writing Is Jazz
Because readers vocalize words in their heads, you, the reader, can play around with words, punctuation, and white spaces. You can be like a poet. Or you can make music with words.
Make. Crisp. Sentences. And then the long ones that go on and on and never seem to end.
Take your readers.
Through the experience.
Of your writing.
59. How to Stop Doubting Yourself
Does it really matter that you missed a day of writing today? Does it really matter that you said something stupid? Ask yourself, what will matter in five years?
99% of things won’t.
60. Say What You Mean
And mean what you say. Which is to say, don’t use the word “perhaps,” or “probably,” or “maybe.” If you don’t know something, Google it. If you still don’t know, don’t write it. The journalistic vagueness, called objectivism, prevalent in most popular magazines doesn’t add anything valuable to the world.
61. Who Are You to Write About X?
In the modern age, where anybody can publish anything, you are what you write.
62. You Don’t Need Permission
The hardest part of growing up in Russia was going to pee when you were at school. You had to raise your hand and ask for permission. Now everybody knew you had to go, and the teacher could say no. Well, we are not in school anymore. We don’t need permission. Create.
Or, if you do need one, here it is.
63. Follow the Interesting
In both writing and life. That’s the secret of most successful creatives. Trust your instincts and innate curiosity. See where they take you.
64. Nobody Can Make You Hit “Publish”
Unless you decide to. So if you’re not sure, don’t publish. It’s OK to kill bad material. It’s OK to start over. Just don’t make it stop you from publishing anything ever.
65. There Are No Rules
There is nothing you should do. So do whatever your instinct tells you. Even if it’s weird. Writing 101 ideas seemed weird to me at first.
66. Don’t Start With an Answer
Start creating anything with a question. And make your art the answer.
67. The Most Important Asset of This Century
Audience. People’s trust. When you have a fleet of loyal followers, you have everything else. It’s the ultimate platform.
68. “1,000 True Fans” Is Harder to Reach Than It Sounds…
It’s not the same as 1,000 followers or 1,000 email subscribers. It’s 1,000 patrons. 1,000 people who are in love with you and your work.
69. …but It’s Doable
If you focus on the long-term. And allow everything to grow slowly while you focus on making your work better than yesterday. Rome wasn’t built in a day. The same with your Substack subscribers or Medium followers.
70. Writing Doesn’t Just Communicate Ideas
It also generates them. It’s not like I had 101 ideas on writing, creativity, and art in my head before I sat down to write this. I only had an intention. A desire. And then I trusted the soup.
71. Start Writing When You Have the First Sentence
Not everything has to have an outline. In my experience, and James Altucher talked about the same thing, when you outline, you tend to communicate many different ideas. But when you let it flow, a story emerges.
Rule of thumb: write version one as fast as you can. And then spend days editing, re-writing.
72. Publishing Fast Is a Sign of Immaturity
To become great, look at what great people do and copy them. Seth Godin doesn’t write 12 books per year, he writes one or two at most. The same for Stephen King.
Paul Graham spends weeks perfecting his essays.
The rush to publish quickly is fear in disguise. Sitting with an unfinished draft, not knowing whether you’ll get it right, is scary. But it’s also necessary to create great work.
Yes, you might publish and get 80% of what you wanted to say out there. But it’s the 20% that separates the great writers from the merely “good” ones.
73. Stillness Breeds Creativity
To get ideas, sit in stillness. Don’t read. Don’t write. Don’t think. Just sit and let your mind wander. Ideas will come.
74. Write Back in Time
The best lifehack I know on generating writing ideas: explain something to yourself in the past, back to when you didn’t know the concept. Show the step by step process of how you got to the conclusion. If you didn’t know something before, chances are, there are others who still don’t know it.
75. Do Nothing or Write
Here’s how Neil Gaiman writes: he sits at his desk and tells himself,
“I don’t have to write. I can sit and do nothing. Or I can write.”
After a minute or so of staring at the wall, he starts typing words. The trick is, he doesn’t pressure himself to write. He has a choice. But writing is more interesting, so the process begins organically.
76. Do It for Someone Else
In Little Women, Jo and her sister were sitting by the beach, and Jo couldn’t start writing. Beth looked at her sister and said, “Do it for someone else, just like Marmee taught us.”
When I feel stuck, thinking of someone, one person, usually it’s a close friend or a family member, helps. Don’t create for everybody. Create for someone.
77. Why Sharing Your Story Helps
People say, “Be vulnerable in your writing.” Too often beginning writers take this advice too seriously. They start sharing everything but the color of their underwear, sometimes even that.
If your ultra-vulnerable story doesn’t help the reader understand your concept, there’s no use in it. Only share stories that help the reader understand something better. Don’t be vulnerable for the sake of being vulnerable.
But paradoxically, being specific about your life helps you resonate with many. On the contrary, generalized advice doesn’t help anyone.
Being specific helps touch the hearts of many.
78. How to Tell a Great Story
Ira Glass said that a story has two parts: action (the anecdote) and reflection. The first helps you generate momentum, e.g., “John woke up, brushed his teeth, made coffee, looked around…” Any continuous action helps to build suspense. That’s how the human brain is wired. But action without reflection, the explanation behind why it happened, leads to nothing. So, advance the action, then reflect. Rinse, repeat.
79. A Blog Is a Platform
Blogging can get you hired. It can help you launch a business with zero marketing budget. And it can help you secure a book deal. Blog not to make money, but to have a platform.
80. Momentum Is All You Need
To create consistently, build momentum. You build it by sticking to a habit. Create every day. At first, it’ll be hard. Think of pushing a train that’s standing still. But in time, as you practice daily, it’ll become easy. You’ll gain momentum. You’ll become almost impossible to stop.
81. The Six-Month Rule
This is how I got started on Medium.
Pick a new project, e.g., writing on Medium. Set a deadline six months from now. Mark the date on the calendar. Good. Now keep creating daily until the six months are up. Don’t think about money, followers, or judge your results. Just keep showing up and keep creating. You’re not allowed to quit.
Once the six months are up, look around. I bet you’ll be surprised.
82. The True Value of Notebooks
I use up one to two Moleskine notebooks each month. I usually write there every idea, thought or quote I find surprising or new to me. But I almost never look back at what I’ve written. It seems that the true value of a notebook lies in just jotting the idea down. It helps you understand the idea better.
Which is to say, always carry, or have a notebook. And no, phones don’t work.
83. Let Your Mind Do the Work
There are so many things you have to remember. So many ideas! How do you keep track of all of them?
Simple: don’t write anything down to remember.
When you read, focus on the reading. When you listen to a podcast, actually listen. Your mind remembers the idea, not the words. It’s like taking a photograph on your iPhone instead of watching with your eyes. It kills the moment.
Let your mind do the work. If you hear/learn/read something important, your mind will remember it. Great ideas are harder to get rid of than you think. And if you forget, well, the idea probably wasn’t worth it.
84. Art Is Anything Risky
And if, as Gardener said, “Life is drawing without an eraser,” then life is also art.
85. Follow What’s Terrifying
You can use the Resistance, or your “lizard brain” to know what to do next. Whatever you fear most. Use fear as a compass. You have two article ideas. Write the one you fear most. That’s the more important one.
Whenever I feel afraid and anxious, I am also thrilled. Because I know that feeling palpitations is how creating art is supposed to feel. And so I relax into my work.
86. Your Cover Matters
Your image matters. Your headline matters. Your formatting matters. Contrary to what they say, people do judge a book by its cover. If that wasn’t the case, people would have simply emailed book and blog texts to each other.
87. March Twenty Miles
Jim Collins, the bestselling author of “Good To Great” and many other business books, has a concept called the “twenty-mile march.” It’s how you produce consistently.
You march twenty miles per day, no matter what. If the weather is bad, and you can’t keep going, march twenty miles. But if the weather is good, and you can march more, you still march twenty miles. Capping the top is as important as capping the bottom.
If you overdo it today, you won’t be able to get back in the game tomorrow. And we’re after long-term consistency. Collins’s research was related to business, but it’s the same in art.
The Muse favors the disciplined creator.
88. “The Secret to Doing Good Research…
is always to be a little underemployed. You waste years by not being able to waste hours.” — Amos Tversky
89. Reading Is Procrastination in Disguise
You feel like you’re doing something. But you’re not. The day ends, and you don’t have anything to show for it. Always have something to show.
90. You Have Jewels Inside of You
In her book on creativity, Elizabeth Gilbert says that one of the universe’s biggest tricks on humanity is the hidden treasures that are buried deep inside each one of us. We uncover them through creative work.
91. Write to Be Wordless
The “wordless wonder,” mind’s peace, can be, paradoxically, achieved through writing words. Witing is the ultimate meditation.
92. Know Your Distance
Don’t start writing by writing a novel, the same way you don’t start running by completing a marathon. Know your distance and start with something simple.
For beginners, Medium is great. So is Twitter, for brevity.
93. Read What You Like
There are no books you should read. Read whatever you like. Follow your curiosity. And if the book is boring, ditch it. Life is too short to be spent on boring books.
94. Focus on the Output
Among successful creatives, there are all kinds of people. Those who drank themselves to sleep each night. And those who did yoga at 6 a.m. And those who married. And those who got divorced. And those who wrote with pen and paper, and those who typed their whole life. And those who blogged for many years, and those who went straight to writing books. There is no correlation between those things and creative success.
The only people who failed to achieve success were those who wasted time. Focus on the creative output above all else.
95. You Only Need One Hit
That’s good news. The bad news? You never know what that hit is going to be. In biology, evolution makes mutations all the time, yet 99.9% of them are useless. It’s the 0.1% that drives the species forward. But to have that 0.1 %, you need everything else for the math to work.
You never know what will be successful. So just produce as much as you can.
96. Writing Is Better Than Sport
Athletes retire at 30. Writers are only starting at 30.
97. One Million Words
Neil Gaiman gives the best advice to beginning authors.
‘When you’re just starting out, assume that you have one million words inside of you that are all rubbish. Get them all out ASAP.’
98. Quality Has Legs
At the end of the day, when the dust settles, and the noise fades, it’s the quality writing that will be left standing. So why not start with it in the first place?
99. Trust Your Feelings
Let your feelings tell you how good your work is. Make your ultimate KPI: your feeling about the work. And then don’t pay attention to what the critics say.
100. The Artist’s Date
This is a concept from “The Artist’s Way.” Take your inner artist on a date. Go somewhere (alone) where you’ve always wanted to go, a museum, to the park, an interesting place. Not because you have to, but because you want to. See where curiosity leads you.
101. You Don’t Really Need 1,000 True Fans
To live a free creative life, you need about $3–4K per month. If you make a paid newsletter on Substack, charging $5 per month, you’d need 600–800 fans. And if you need less (or charge more), you’d need even fewer people.
Which is to say, don’t blindly trust everything you read on the Internet.
(BONUS) 102. Who Are You?
Write and find out. Create and find out. As Henry Miller wrote, “Writing is a voyage of discovery.”
Who you are is what you write.
