Essay – May 2020

How Should You Write?

An essay on combining art, money, lifestyle, and long-term creative goals.

How should I write?

This is a question I keep asking myself.

When I just started writing, I published on Medium every day. Over six months it worked great for me in terms of audience growth, finding my voice, and improving writing skills.

The problem is — by publishing daily, I forced the conclusion quicker. I was more a ‘publisher’ than a writer. And even though my skills have improved, my posts became worse, not better. I became more shallow, following the quantity rather than going deep and focusing on quality.

An obvious attempt to answering it would be to look at what others did. Just look at what Seth Godin, Steven Pressfield, Neil Gaiman, or any other author you admire, and copy whatever they are doing. If Seth Godin publishes daily, let me do that too.

This works. At least, in the short-term. There’s nothing wrong with copying people you aspire to be like when you’re just starting out — that’s how you learn.

But on the scale of years — and that’s the scale you should be thinking about your writing because it’s hopefully your life’s work — you want to figure out not just what works, but what works for you.

More than that: ‘How should I write?’ sounds simple, but it’s a tip of an iceberg. There is more that goes into answering this question than seems at a glance. And as my geometry teacher in Russia taught me in 8th grade, ‘If you can’t find a solution quickly, make a bigger drawing.’

I propose transforming the vague «How should I write?» question into three smaller ones.

• What do you (ultimately) want? — As in, why are you writing in the first place?

• What is enough? — It’s good to know where you’re trying to get to if you want to have any chance of getting there.

• How do you get there? — What’s the best strategy behind doing all of the above?

Your daily actions and routines never exist in a vacuum. They are the effect of your ultimate dreams, the definition of your goals, and a solid strategy. Answer the three above — and you’ll understand how to behave on a daily basis.

Let’s break them down one by one.

What do you want?

You ask yourself, ‘How should I write?’, but a more important question is: should you write in the first place?

Understanding your ultimate goal in life makes everything clearer, like wiping your windshield after a rainy day.

Most people usually have some kind of idea where they want to end up. It’s either a still image, or a feeling, or a sense.

Popular self-help spiritual books all give similar advice: make the image of your dream life as clear as possible and success will come. This is partially true. But not because of some hidden magical forces that help people discover their ‘inner billionaires’. No. But because by thinking about something a great deal, your brain focuses on finding patterns in the external world.

If all you think and read about is pink elephants, you’ll end up seeing pink on the street, find animals in cloud patterns, and hear trumpets in music.

In my case, I have a vivid picture of me writing at a desk, in a beautiful (but not too expensive) house, somewhere in North America. I have a huge collection of books — lined up on the bookshelves next to my desk — and a large window in my study. I can see nature, my family, and a dog playing outside. I wave at them and then return to working on my book.

That’s about it.

I don’t think about how much money I have, what kind of writer I am (although it’s probably non-fiction), and what else I am doing with my life. All I need for now is to understand, or at least get a feeling of, what the end goal for me is. It’s being a full-time writer.

I make it sound easy, but knowing what you want is hard.

I also cheated. I worked on figuring this out for quite some time. But there are many folks out there — including some of my friends and family members — who struggle to define what success for them looks like.

Role-models help. People you admire are nothing but a proxy for what you aspire to become. You are in love with a celebrity not because you love their hair (although that may be with Justin Timberlake), but because they have something you can relate to. Something you also have but are too afraid to act upon.

Tracking yourself also helps. I kept an Excel spreadsheet where I tracked myself for 45 days in a row. My daily inputs were things like sleep quality, sport, food, but most importantly: what I did and day quality from -2 to +2.

After I finished, I looked back and had a few breakthroughs. For example, I learned that on the worst days, I didn’t have enough sleep, so keeping to 8–9 hours per day is key. On my best days, I wrote for 2–3 hours in the morning. This exercise eventually inspired me to quit my video production business, move to another country, and start writing full-time.

There are many things that can speed up the process of self-understanding, but the more I do it, the more I see that it never finishes. My father is 43, and he’s still figuring himself out, changing countries and launching careers.

It’s an illusion to think that grownups have all the answers. When I was 18, I was convinced that I know everything about myself. I thought I’d be an entrepreneur, build companies, and become a billionaire by 30.

It seems that when you’re 18 you try to overcompensate for the lack of data about your life through arrogance. And the older you get, the less you actually know yourself.

As Paul Graham wrote,

“When I was a kid, I used to think adults had it all figured out. I had it backwards. Kids are the ones who have it all figured out. They’re just mistaken.”

It’s also fine to change your mind. Our perception of self is an illusion. Fundamentally, there is no such thing as ’personality’, especially because it changes with time and space.

You grow older, and you become a different person. And every time I go back home to Russia, I feel like another Sergey is coming outside of me, behaving the way I don’t normally in the West.

Your identity is not something fixed. It’s fine to find yourself with contradicting wants and aspirations. Being a puzzle is part of being human.

For example, I am puzzled not because I am struggling to do, but because there are so many things I could do.

It would have been easier if I was born fifty years ago when there was no such thing as Medium, and you couldn’t write a book in 30 days to self-publish on Amazon. Things used to be simple.

If you wanted to write, you had 1 or 2 paths to take, and that’s it. To become successful in the modern world, you need to be equipped with a strong sense of identity and confidence to say ‘no’ to distractions.

That’s why understanding what you ultimately want is so important. It helps you organically edit out the unnecessary crap.

Figuring out what you want is not just saying ‘yes’ to a vocation (e.g., writing). For example, a short-term goal of mine is to be someone who lives a free creative life — makes money with words. But it also means saying ‘no’ to things that don’t fit — no matter how popular, lucrative, or great they might seem.

If you’ve decided to be a writer, you shouldn’t post on Instagram to ‘build your network.’

You should do the only thing that gets you closer to your goal: writing.

What is enough?

How much money, fame, or work do you want from your chosen life’s path? How much is enough? Not understanding that is like driving without a destination. You’ll just end up driving everywhere. Or what’s worse — somewhere popular, where all the banner advertisements lead to — but where you didn’t want to go in the first place. It’s a cliche because it’s true: to get from A to B, you need to know exactly where both A and B are.

Naval Ravikant calls desire a “contract you make with yourself to be unhappy until you get what you wanted”. It makes sense then to make your desires as small as possible to be unhappy less. There are no grumpy minimalists.

On the contrary, the bigger your desire is, the harder and longer you’ll have to work for it. For us, writers, this directly correlates with how many writing projects you should take on at any given time.

What lifestyle do you want? Not just in what things to own, but in how to live. Do you want to wake up to an alarm clock before dawn and rush off to work, or does sleeping in and doing yoga on the grass sound better?

All I need as a twenty-two-year-old is enough money to feed myself, have a roof over my head, travel, and to pay off debt. $2,000 for rent + $1,000 for food + $500 for travel and $500 for debt = $4,000 per month. That’s $48K per year. That’s more than doable with an average salary or a handful of freelance gigs.

In Kevin Kelly’s terminology, I’d only need 571 ‘true fans’ (not 1,000!) each paying $7 per month on a platform like Substack.

Of course, I can’t expect to live like this forever. My father’s friend once told me that the beauty of youth is the ability to shrink your lifestyle the way you won’t be able to later in life. You (yet) have no obligations and nobody to feed but yourself.

This is the time when you can eat beans, live on minimum wages, and explore the world with full creative freedom. That’s something I’d like to do.

But the conversation of how much is enough is simply about your ambitions. And I don’t think ambition is something you can alter within yourself. It’s either there or not.

It also varies by person. For some, having an average house and a family with two kids and a Prius is enough. For others, billion-dollar businesses, mega-jets, and being the President of the United States won’t be enough. Ambition defines your ceiling: how successful you can (potentially) become. You can’t ever turn it off.

Not all ambition is good. It can be exhausting. People with ambition live with a hole in their chest. They can’t be fulfilled unless their hole is filled with stuff, accomplished goals, expensive restaurant dinners, and a personal YouTube channel.

But if this is not what you want, don’t pay attention to ‘the hustlers’. Pity them. You are where they’ll never be even if they achieve all of their goals. It’s a true gift.

You can find your ambitions by paying attention to how you work. If you’re not ambitious, you won’t tend to need or want to work a lot.

It works the other way around too. If you’re a workaholic, trying to fit a week into a day or publish 15 articles in a week, it might be a sign of high ambitions.

Know your ambitions. Once you understand the level to which you aspire, it becomes tangible. You know where you’re going and how soon you can be there.

But ambition is also like grass — no matter how thick an asphalt you pour over it, it’ll still grow through. It’s much easier to accept ambitions than to fight them. You don’t want to end up like the main character in Brad’s Status, who played the part of a good father, but secretly envied his more successful friends and even his Ivy League son. You can’t trick yourself.

Too many young folks aspire to big goals simply because it's cool. They aren’t to judge. Most celebrities you see online are overly-ambitious and glorify hard work. They make you feel inferior if you don’t fancy becoming the next CEO of a Fortune 500 company. I don’t agree with that.

If Elon Musk works 16 hours per day (which is probably an exaggeration anyway), but you don’t want to become Elon Musk — it’s OK to work less. More harm is done by trying to prove something to yourself than by doing nothing.

Whatever your ambitions are, it’s way cooler to be happy.

Ultimately, you are the one who defines ‘enough’. I recently heard a story of a man who wrote a book for 50 years — one sentence at a time. The book was only discovered after his death, and was filled with wisdom that only living a long reflective life can provide.

The Greeks had a word for a powerful force that lives inside people, pushing them towards creating meaningful work: daimon. The Romans called it genius. You can also call it ambition. It’s the same potential that a little acorn has to grow into a massive oak tree if given the right conditions.

That same force wants you to write. There’s no way around it, so you have to just give in to it.

But if you are in the business of writing, there might never come a point when you feel ‘enough’. Maybe you’re a road, not a destination. Henry Miller wrote that ‘Writing is a voyage of discovery.’ Who you are is what you write.

If you don’t know who you are, write, and find out. And while you might have goals and ambitions, the process of self-discovery and creating art is endless.

It’s a process. What seems enough now, might not be enough in the future. So my best guess is to accept your true ambitions, and focus on the closest goal.

As creators say, trust the soup. Let your work lead you.

How do you get there?

In manufacturing, the process of deconstructing objects to see what they were made of is called “reverse-engineering”. Once we know what we want, and how much of it we want, we can go backward. We can reverse-engineer to figure out how to get there.

Let’s say you want to become a non-fiction writer. You want the book deals, you want the fame, TED talks, coaching, courses, online fame, and everything that goes with the lifestyle of being a thought-leader in the 21-st century. You want to be someone like Seth Godin.

How do you become someone like Seth Godin? As I said in the beginning, one way is to look at what he is doing now.

Seth Godin just wrote his 19th bestseller, teaches Udemy courses, launches workshops, and publishes daily on his blog. You could imitate everything he’s doing.

But that’s like trying to replicate an iPhone by staring at the one you carry in your pocket. You need the skills, the right materials, possibly even a team. And you need a foundation. As James Altucher said, “The secret to success is to build the foundation for it”

Seth Godin became Seth Godin because he worked many years to build the credibility, the reputation, and the trust that earned him the right to live his current lifestyle. You can’t expect to skip all those steps and begin at the end.

What you need to do instead is to trace your way to success backward. Starting from the end, asking yourself, “What comes before X?” until you get to the point where you are now.

Point B — fame. What comes before fame? Seth’s TED talks and 19 bestselling books. What comes before books? Credibility. People trust him enough to buy books from him. What comes before credibility? Work. Seth’s businesses which he sold to Yahoo. What comes before work? Showing up each day and earning yourself a reputation to do the work. What comes before showing up? The decision to do so.

Once we get to the point where we can’t ask “What comes before?”, you know you’ve arrived at point A. That’s where you are now.

You can’t just start at the end and copy what you see. That’s confusing cause and effect. If you blog daily like Seth Godin and call your blog by your name, nobody will follow it. You need to earn the right, the credibility to teach people things — and you do that by doing the work and showing up each day for the people you decided to serve.

Again — don’t try to copy somebody else’s life. It’s impossible, and not worth it. Jealousy is useless because to switch places with someone, you’ll also have to get the bad stuff too — the struggles, anxieties, and problems that each human life has. As Gary Vaynerchuk once put it, “Everybody’s got something.”

The important thing is to see that success takes time. The lifestyles of people you admire took decades to become the way they are today. To want is to lack, so failing to live the way you want now is not simply normal, but essential for your motivation.

And if there’s one thing that history teaches us, it’s that people who have achieved creative success focused on creative output. People who want X need to focus on doing X. If you want to be a writer, just start writing without overthinking it.

You also see, that no matter the volume of work, it was usually just a handful of ideas and projects that made the success possible. Seth Godin wrote hundreds of books, but only 19 of them became bestsellers. As they say in the music industry, you only need one hit.

I see this in my writing too. Over the course of the past three months I published about 90 pieces on Medium. Just 2 articles generated 90% of the money I made over that same period. Does this mean I could not have written the other 88 articles and still generate 90% of the profits? Yes, but only in retrospect.

In evolution, mutations are abundant, yet 99.9% of them end up to nothing. It’s the 0.1% of rare mutations that make the individual more suited to the environment that moves the whole species forward. But to have that 0.1 %, you need to have them all for the probability math to work.

No matter what the publishing industry tells you, nobody knows what piece of art will succeed and when. That’s why publishing houses have a similar model to venture funds: they place bets. Quantity is one of the best things you can focus on as an individual aspiring to build a creative career. It will increase your chances of success, and improve your skills. And if you’re publishing on a platform like Medium, it will also make you money and help you build an audience as a by-product.

On the other hand, if you only focus on quantity, your writing might suffer. At one point you might find yourself forcing the conclusion quicker, working each day trying to hit “publish” instead of writing something meaningful. And when you’re just starting out, quality is essential — to build your brand and reputation.

I’ve thought about this dilemma a lot. And I came to the conclusion that there’s no one way. Each person’s path is different.

Unlike manufacturing, in life there doesn’t have to be one right answer. What works for you, worked for Seth Godin, and generally “works” — are three completely different things. They can co-exist.

The key to building a viable strategy towards your creative success is not to ask what “works”, but to seek knowledge about yourself.

All successful creatives have one thing in common: they followed what worked for them.

How should you write?

The short answer is that you need to put in the daily effort. Woody Allen said that 80% of success is showing up to work each morning, so that’s what makes sense to focus on. It’s up to you as a creator to define what your version of ‘showing up’ might be.

If you’re looking for a directive, a good one might be: put in as much effort as you can for as long as possible.

If you excuse me for quoting Gary Vaynerchuk for the second time, he called it ‘micro-speed, macro-patience.’ But we’re less interested in speed, and more in the quality of our effort. Hence, a better version of it might be: ‘micro-effort, macro-patience.’ Work hard each day, but don’t expect results to come quickly.

Personally, I am embarrassed to admit that I wasn’t following this directive for the past six months. I guess I just didn’t take Medium (or content creation) seriously enough.

As I said in the beginning, I wrote daily, but I also spent 30–60 minutes on each piece, thinking it was enough. I now see I was mistaken. As your confidence grows, so do your creative aspirations. And it’s only natural that you adjust your daily work routine (‘showing up’) accordingly.

For example, Casey Neistat — now a viral YouTube blogger and film-maker — woke up one day and decided that he doesn’t need anyone’s permission to shoot videos. That’s how, at the age of 34, he launched a daily YouTube vlog that now has more than 10 million followers.

Some people might think he was selling himself short by going on YouTube to show his work, but few know the effort Casey puts into each of his daily videos. He usually wakes up at 4 AM and edits the video for several hours before hitting ‘publish’ and going outside to shoot footage for the next video.

It’s that kind of obsession that leads people to creative success.

Many aspiring writers want to know the best way to write, but they aren’t ready to put in the work. They are looking for a shortcut. But in writing, blogging or film-making there isn’t one.

Platforms like Medium or YouTube might have turned some people into millionaires — but only because the creatives set themselves a high bar from the start.

The laws of distribution might have changed, but the laws of physics didn’t: if you want to achieve success, you have to work hard. And as Medium and YouTube become more competitive, it becomes almost impossible to put out mediocre content and still be noticed.

If you want to be at the level of Casey Neistat, you’ll have to expect to put at least the same amount of effort as he did. Even if this means waking up early and working for 3–4 hours each day for many years.

If you want to make content creation your full-time job, it’s time to start treating it as one.

And because platforms like Medium or YouTube are made to support meritocracy, succeeding as a creator on them is much nobler than securing a lucky deal from HBO or Random House.

Your work will speak for itself.

The beauty of the writing profession is that the more you do it, the better you get. When asked how to become a great writer, Neil Gaiman gave the following advice:

“Assume that you have one million words inside of you and they are all rubbish. Get them all out.”

Time works in your favor. Athletes need to retire in their thirties, while some of the best writers only published their bestsellers in their forties, fifties, or sixties.

Life isn’t school, and you don’t become successful by trying. People judge you by results. And when it comes to results, I’d like to think that ‘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. And if we bring everything we said above to a close, we see that it’s the kind of writing that you — the creator — are satisfied with.