mr. r. s. braythwayt,

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What I've Learned From Failure
What I've Learned From Failure

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On a semi-regular basis, people email and ask me for advice about writing. Whether I’m being asked for general advice about developing an audience for a blog, or whether I’m being asked for specific feedback on an essay, my advice is always the same: write.

Three years ago, I summarized my advice in an essay. It’s rather specific to the “problem” of building a reputation on the Internet, rather than about writing books that teach or presentations that sell, but that’s what I know, so that’s what I share.

Here it is again, more-or-less exactly as I dashed it off in haste:

How to Win Friends and Influence People with an iPad in a Coffee Shop

Yesterday was my 49th birthday. By fortuitous circumstance, I spotted an item on Hacker News explaining that reputation on Stack Overflow seems to rise with age. I don’t have very much Stack Overflow reputation, but I do have a little Hacker News karma and over the years I’ve written a few articles that made it to the front page of Reddit,, and Hacker News.

Somebody suggested that age was my secret for garnering reputation and writing well. I don’t think so. Here’s my secret, here’s what I think I do to get reputation, and what I think will may work for you:


That’s it. That’s everything. Just write. If you need more words, the secret to internet reputation is to write more. If you aren’t writing now, start writing. If you are writing now, write more.

Now some of you want more exposition, so for entertainment purposes only, I’ll explain why I think this is the case. But even if I’m wrong about why it’s the case, I’m sure I’m right that it is the case. So write.

Now here’s why I think writing more is the right strategy. The wrong strategy is to write less often but increase the quality.

This is a wrong strategy because it is based on a wrong assumption, namely that there’s a big tradeoff between quality and quantity. I agree that given more time, I can polish an essay. I can fix typos, tighten things up, clarify things. That’s very true, and if you are talking about the difference between one essay a day done well and three done poorly, I’ll buy that you are already writing enough if you write one a day, and you are better off getting the spelling right than to write two more unpolished essays.

But in quantities of fewer than one essay a day or one essay a week, the choice between writing more essays and writing higher quality essays is a false dichotomy. In fact, you may find that practice writing improves your writing, so writing more often leads to writing with higher quality. You also get nearly instantaneous feedback on the Internet, so the more you write, the more you learn about what works and what doesn’t work when you write.

Writing on the Internet is nothing like writing on dead trees

Now that I’ve explained why I think writing less often is the wrong strategy, I will explain how writing for the Internet rewards writing more often. Writing on the Internet is nothing like writing on dead trees. For various legacy reasons, writing on dead trees involves writing books. The entire industry is built around long feedback cycles. It’s very expensive to get things wrong up front, so the process is optimized around doing it right the first time, with editors and proof-readers and what-not all conspiring to delay publishing your words where people can read them.

Worse, the feedback loop is appalling. What are you supposed to do with a bad review on Incorporate it into the second edition of your masterpiece?

Speaking of masterpieces, that’s the other problem. Since books are what sell, if you want to write on dead trees, you have to write books. A book is a Big Thing, involving a lot of Planning. Structure. And Organization. It demands a quality approach. Books are the “Big Design Up Front” poster children for writing.

Essays, rants, opinions… If writing book is Big Design Up Front, blogging and commenting is Cowboy Coding. A book is a Cathedral, a blog is a Bazaar. And in a good way! You get feedback faster. It’s the ultimate in Release Early, Release Often. You have an idea, you write it, you get feedback, you edit.

I am unapologetic about editing my comments and essays. Some criticize me for retracting my words when faced with a good argument. I say, Fuck You, this is not a debate, this is a process for generating and refining good ideas. I lie, of course, I have never said that. I actually say “Thank You!” Or I try. When I fail to be gracious in accepting criticism, that is my failing. The process of releasing ideas and refining them in the spotlight is one I value and think is a win for everyone.

Another problem with a book is that it’s One Big Thing. Very few book reviews say “Chapter two is a gem, buy the book for this and ignore chapter six, the author is confused.” Most just say “He’s an idiot, chapter six is proof of that.”

A blog is not One Big Thing

Many people say my blog is worth reading. They are probably wrong: I have had many popular essays. But for every “hit,” I have had an outrageous number of misses. If you read everything I wrote starting in 2004 to now, you’d be amazed I get any work in this industry. What people mean is, my good stuff is worth reading.

“In quantities of fewer than one essay a day or one essay a week, the choice between writing more essays and writing higher quality essays is a false dichotomy.”

That’s the magic of the Internet. Thanks to Twitter and Hacker News and whatever else, if you write a good thing, it gets judged on its own. You can write 99 failures for every success, but you are judged by your best work, not your worst.

And let me tell you something about my Best Work: I often think I am writing something Important, something They’ll Remember Me For. And it sinks without a trace. A recent essay on “the value of planning and the unimportance of plans” comes to mind.

And then a day later I’ll dash off a rant based on a simple idea or insight, and the next thing I know it’s #1 on Hacker News. If I was writing a book, I’d do a terrible job, because my nose for what people want is broken. When I write essays, I don’t care, I write everything and I let Hacker News and Twitter sort out the wheat from my chaff.

If you have a good nose, a great instinct, maybe you can write less. But even if you don’t, you write more and you crowd-source the nose for you. And thanks to the fine granularity of essays and the willingness of the crowd to ignore you remises and celebrate your hits, your reputation grows inexorably whenever you sit down and simply write.

So write.

(original discussion)

p.s. Here’s an interesting counter-point.