Be your own harshest critic

As a writer, you have to be our own harshest critic,

You have to inhabit the role of a very critical reader every time you write. You have to poke holes in it wherever you can. You have to be brutally self-critical with what you're writing, because if you don't do, the reader will do it for you.

And because of the asynchronous nature of reading and writing, you have no recourse at that point. The battle will be lost.

The final ten percent

The new ideas and novel insights that characterize great writing can feel impossible to create, but in reality, most great writing represents just an additional 10% of extra context and refinement over existing ideas and truisms.

Good ideas generally don't appear from the ether. They are riffs on existing ideas, refinements, responses, zooming in or zooming out. In almost all cases, 90% of the idea exists elsewhere—greatness is unlocked with the addition of the final 10%.

So stop trying to conjure miracles and focus your energy on the collection and analysis of the existing ideas in your industry.

Great writers are usually prolific observers, people who plumb the world's deepest recesses for information, absorbing and recording everything. They look for the commonalities between their observations, the macro view, the frameworks that sit atop the individual events—the final elusive 10% that makes the 90% more valuable.

Related ideas:

• Collect failure

The risk/reward asymmetry of difficult things

There is a huge (beneficial) risk/reward asymmetry in doing very difficult things.

One of the roles I played at my last company was pinch hitter. I got tagged into difficult customer accounts with the mandate: fix this. In those situations, failure is expected. If you can't solve the impossible problem, no big deal—you're in the same situation as everyone else that tried and failed to remedy the issue. Success is unexpected.

But by that same token, if you manage to solve the problem, save the customer, to win, it's a huge deal—you turned the tide and delivered an outcome that nobody thought possible. Your failure is low risk; your success is high reward.

With that realisation I threw myself into every ugly situation that came my way: rewriting rejected articles, trying to save customers that wanted to churn, pivoting failed strategies.

I struggled and failed a bunch of times—but people only remembered the wins.

How I read books

I liked reading about how Wes Kao reads books, so I figured I'd share my own process:

• Finish every book. In defiance of popular wisdom, I make a point of finishing every book I start—no matter how awful. I have learned much about good writing from reading bad writing, and I often find useful information squirreled away in the dark corners of otherwise unremarkable books. It has the added benefit of making me think a little harder about every book I pick up.

• Take detailed notes. I remember very little from the first hundred books I read. That seemed a shame, so I started talking detailed notes. I read physical books and take digital notes in Obsidian on my phone. The process (particularly for great non-fiction books) is incredibly interruptive, but that's by design: I read actively, questioning ideas and making connections to other ideas. My goal isn't to finish books, but to learn (and retain) useful ideas from them.

• Read weird, esoteric books. I like this quote from Arthur Koestler in The Act of Creation: "All decisive events in the history of scientific thought can be described in terms of mental cross-fertilisation between different disciplines." I think the same applies to creativity generally: new ideas in one domain often result from old ideas in others. I read widely on any topic that seems interesting and try to leave the marketing echo chamber as often as possible.

• Own your books. I buy and read only physical books. I aspire to build a library of ideas for my friends and family to access, and I'm wary of the fact that services like Kindle effectively limit you to renting your books, and not truly owning. More on this idea: Buy books liberally.

• Reread exceptional books. Great books are few and far between, and it makes sense to revisit those that have the biggest impact on your worldview. My most re-read book is The Road by Cormac McCarthy.

And I'll finish by quoting Wes directly:

“More books isn’t the goal. Books are a means to an end. The end is to become a wiser person, to spark your own imagination, to get a deeper understanding of a topic. They’re not the goal itself so I’m not impressed if you’ve read 52 books in a year. I’m more impressed if you read one book and let it deeply change you.”

Related reading:

• Buy books liberally

• Never outsource understanding

Marketing is repetition

Good ideas are hard to find, and most marketing channels are extremely lossy: most people will not see what you share, and those that do will forget it very quickly.

Once you have a good idea, shift gears towards repeating that same core idea through as many mediums and framings as possible.

Buy books liberally

I'm a huge cheapskate but I allow myself total, reckless freedom to purchase books. I buy any book that seems interesting, any book that challenges a deeply-held belief, and any book that is mentioned by someone I respect.

Books are condensed human knowledge and experience. When so much of life is striving to understand how things work, it seems only sensible to learn from others before expending vast amounts of energy through trial-and-error.

Books are also absurdly, comically cheap. At worst, they offer several hours of entertainment; at most, they contain ideas that can completey transform the trajectory of your life (and the lives of those around you).

I buy books faster than I can read them, and see no issue therein. I aspire to build a library, a place of inspiration and possibility that can cater to my wife's interests, my friends', my childrens'. There is something both humbling and enticing about a room full of unread books (what Taleb calls the antilibrary): a reminder that there are always more ideas to explored, and that your next great idea is only a few pages away, if only you know where to look.

Perhaps most importantly, it's also fun to allow yourself an area of no-holds-barred indulgence.

Related posts:

• Never outsource understanding

Collect failure

It's easier to become great at something by collecting failures than it is by trying to collect successes.

Trying to be "great" can be paralysing, and virtually impossible. The standard is impossible to achieve for a novice to achieve. You're focusing your energy on an outcome, something fundamentally outside of your control.

"Write a great book" is a terrible goal. How can you action the "great" part? Do you even know what "great" means? Is your sense of taste and judgement informed enough for that to mean anything? "Get published" is similar unhelpful. The ultimate success or failure of the goal lies with outside forces.

But "write twenty books" is a much more useful. It lies entirely within your control. It builds fast feedback loops. It develops taste and judgement. "Get rejected twenty times" is even better: it requires interaction with the publishing process, exposure to feedback, and incentivises effort instead of deterring it.

In On Writing, Stephen King shared an anecdote which has always stuck with me. After his first few rejection slips for his manuscripts, he shifted his goal from "getting a manuscript published" to "collecting rejection slips from publishers." He struck a crooked nail into his wall and set himself the single goal of filling with rejection slips. He collected failure, and through doing so, made success far more likely.

It is far better to focus energy on processes and goals that we can control, and allow success to emerge as a byproduct. Aiming to collect failure gives us control, and reframes the negativity that comes with failure—it becomes something useful, even necessary, in service of the ultimate goal, instead of a pain to be avoided.

Get great with bad gear

I learned to play guitar on a hunk of plywood with action high enough to fit a phone book between string and fretboard. I remember feeling embarrassed whenever I opened my gig bag at jam sessions, pulling out my eBay-caster with the sanded-off brand name ("Maxine"), surrounded as I was by wealthy middle-class bandmates with Fenders and Gibsons.

But the embarrassment only lasted until I played those first few runs, fast little triplets and sweeps, and it became abundantly clear that I was a good guitarist - great, even, and in spite of my gear, not because of it.

As a child I had bad gear out of necessity, not choice, but even into adult life I've adopted the mantra as a personal belief: good gear is a privilege that needs to be earned, and I start all of my hobbies and interests with basic gear.

Today it is easier to buy than do; easier to exchange money for the possibility of doing something amazing than to actually go and do something amazing; easier to buy an £800 MIA American-made Telecaster than it is to sit and practice scales for 3-hours a day.

Getting great with shit gear is a commitment to skill and practice, the inverse of "all the gear and no idea." It minimizes the cost of abandoning new hobbies, and it builds a real appreciation for good gear when it's eventually earned.

Weasel words

You can become a better writer almost immediately by learning to identify and replace “weasel words.”

Weasel words are words (or phrases) that seem to convey clear meaning but upon closer inspection offer no real substance, like:

• “business outcomes”

• “experts believe”

• “analyzing data”

• “make a decision”

We use weasel words to hide gaps in our knowledge. They are often subconscious crutches that sound so coherent and fitting that we don’t recognise them for the hollow, empty phrases they really are.

But in almost all cases, writing can be made vastly more persuasive and helpful by deleting these words and replacing them with a simple list of the actual concrete processes they are acting as placeholders for:

• “analyzing data” -> “looking for outliers in monthly traffic performance”, “creating cohorts to track performance across authors and topics”, “comparing recent monthly performance to historical benchmarks from last year”

Weasel words proliferate because finding these concrete processes is hard and time-consuming, requiring the writer to conduct more research or introspect more deeply. But it is precisely these concrete, tangible actions that provide the most value to a reader trying to understand a concept or learn a process.

Never outsource understanding

It's easy to generate summaries of articles, essays and research papers in a couple of clicks.

But the point of summarisation is not to possess a summary—it's to develop understanding of the source material: its usefulness, its applicability to your areas of interests, the strengths and weaknesses of the idea.

Manual summarisation is a laborious process that forces you to think, evaluate and learn. Automatic summarisation divorces the effort from the outcome, like drinking fruit juice instead of chewing an apple.

The effort is not to be avoided.

Could < should < did

There are three levels of credibility in writing. You can make your writing more persuasive by moving up the hierarchy.

I like to think of them as could, should, and did:

• Could: the writer talks about things you, the reader, could do, in a theoretical and abstract sense. Their recommendation is simply a summary of other sources of information, and based on no firsthand experience (and should probably be disregarded). Most content marketing lives inescapably in "could" territory.

• Should: the writer is brave enough to voice an opinion (hooray!). They seem to have evaluated more than one methodology or idea, and performed a little synthesis to turn multiple ideas into a concrete recommendation. They seem willing to stand behind their recommendation (at least a little).

• Did: rarest of all, the writer is willing to their own medicine and actually do the thing they talk about. They write from firsthand experience, either sharing past experience or testing their ideas through experimentation. Their writing is more than an academic exercise—they have skin in the game. This is the gold standard, and their advice is probably worth paying attention to.

How to live as a ghost(writer)

I've recently seen a few people share frustration at the quirks of being a ghostwriter, and they largely circle the same issue: namely that your effort goes "unrewarded." You write something amazing, and someone else gets the credit.

I've been ghostwriting for over a decade. I have a good number of bylined articles, but even so, some 90% of my total writing has been published under someone else's name.

Now—I get the frustration of ghostwriting. But I also think it's misinformed, for a few reasons:

• Your "reward" is money. People are willing to pay for ghostwriting because you are making them sound smarter, better, more polished; if you were to get recognition for the writing, then the entire value proposition of the service crumbles. Anonymity is what makes ghostwriting viable.

• Your anonymity should be costed in. Because there are no secondary benefits to ghostwriting—like personal brand building—you need to make sure that the monetary compensation alone is enough to make you feel good. If you feel that you're getting a raw deal for your work, raise your prices. Ask yourself: how much would I need to charge to feel happy about writing this anonymously?

• The same article published under your byline wouldn't get traction. If you—-a writer—are ghostwriting for the CEO of an ecommerce company, publishing the same article under your byline would not serve you. The success of your article is a product of your writing, yes—but also the person you wrote for, their audience, their credibility.

• A win for them is a win for you. Seeing your ghostwritten article go viral should feel good, even if you aren't credited: it's a sign that your service is worthwhile, that you're delivering the thing you promised your customers. Take pride in it.