Question from a reader -
You have maintained your commitment to being prolific which is made even more exceptional by the fact you are travelling around the world at the same time.
I realise your article on being prolific is about this, but accepting that I'm going to release a lot of crap before I realise something good is a tough wall to knock down. My biggest issue writing anything seems to be that it feel insufficent. Naturally no post I write has the length of Steve Yegge, the persuasiveness of Paul Graham, the content of Unqualified Reservations etc. etc. and while I can consciously accept this, there seems to be some mental block. How do you go "that's sufficient" and release it into the wild?
There's two basic approaches to being successful as a writer. The first, we could call the "Paul Graham / Derek Sivers" approach. This is where you explore a lot of ideas privately, go forward with the best ideas you have, and edit and polish the hell out of everything before you release it into the world. If you do this, and you've got talent as a writer, and you've got important ideas - then you're going to consistently only release masterpieces.
The second way is to just write a hell of a lot and know that a number of the things you write will turn out quite well, but your average quality level will be much lower. We could call this the "write every day no matter what" approach.
The first way is great for people who can do it. The biggest problem is, you've already got to have immense writing talent and thinking talent to do it, which most people don't have. (I don't have it.) On the other hand, writing every day trains you up pretty quickly in better writing. You can see something in a book you read, and say, "Hey, I could try writing something along those lines." You can experiment. You get lots of feedback instantly. You become a better writer and thinker by writing regularly and releasing everything of passable quality.
The second problem with the Graham/Sivers/ultra-high-quality approach is that it's pretty inconsistent. Paul and Derek have both noted that half or more of the writing pieces they start working on get thrown out because they aren't good enough. If you look at Graham's essays or Sivers's blog, you'll see wildly varying amounts of writing. There's months of hit after hit, followed by months of silence at times.
It's pretty hard to control when you have max quality output. But you can pretty consistently get your median quality output by just writing a lot. Even in a funk, with some flailing around and forcing yourself to write something, you'll hit your median quality pretty quickly.
So the question is, is your median quality of writing good enough to release into the world?
Answer: You're not qualified to judge that.
In business, it's a truism that the customer crowns the winners. It doesn't matter how much a company likes its own product if customers don't buy.
The same thought is not always accepted in the creative fields. But if you want to write or do something creative, as soon as you send it out into the world, you no longer fully determine the work's success and impact.
That... seems an obvious thing in a way, but it's actually a tough pill to swallow for many would-be writers or other creators. The external world determines the external success of a piece of work.
So, how do you know if a work is good enough?
You follow the best practices, you work to the best of your ability, but then... you just let it go and see what happens. You observe the feedback and iterate accordingly.
How do you know if it's good enough? Well, you could develop a finely tuned sense of good writing and good content, and given enough study and practice at it, maybe you could achieve that level where everything you write is good and polished.
Actually, that's exactly the Graham/Sivers way.
Alternatively, if you're not that skilled, you could set hard rules and never break them. I think the latter path is infinitely easier to walk.
The easiest way? Write every day, publish something every day. You'll inevitability write a lot of trash, but you'll write some gems too. Most importantly, your median quality of writing will rise quickly. Writing every day has a certain magical quality to it in that you can take multiple cracks at a new style or format or something. If you didn't get it quite right on Monday, take a shot again on Wednesday. And again on Saturday. You're writing every day, and releasing writing every day, so you've got lots of writing to do.
You don't have to do daily. But you do need a schedule, else you're very likely to abandon things.
Well, unless you're already a world class writer and thinker. Then the first path is open to you. But if not, then write a lot and release your writing regularly. The sad truth is that much of your writing won't be good enough, by your standards or by the external world's. But if you keep going, you'll improve.
As you improve, you'll get some wins and you'll find the intersection between what you like writing and what people like reading. People will spend more time reading your writing, knowing that while many of your pieces are "just okay," they've got a chance of finding a real gem or masterpiece if they read regularly... and I'll tell ya, real gems are worth incredibly a lot. If your median quality is okay and you've got an occasional gem, then you're doing a great thing for the world.
How do you write regularly?
You set a schedule.
You stick with it religiously.
Much of your work isn't very good.
But you improve rapidly.
And sometimes, you write a real gem.
And feel free to go "masterpieces only" once your skill in writing and thinking is there.