Initiative

Thursday, 20 April 2006

There’s no other way for me to start this other than by firing away: Last week I left my full-time job at Joyent, for the sole reason so that I can write Daring Fireball as a full-time job.

Two years ago, when I made tentative steps in this direction, it was like I put the idea out there and then poked it with a stick to see what happened. What I’m doing now is like jumping out of a plane with this idea as my parachute.

When I launched the membership program two years ago, I wasn’t sure whether it would be a failure, a bonanza, or something in-between. Ends up it was something in-between. I mean that in a good way, because it was way more successful than I honestly expected. But it was also less than I had sort of secretly hoped.

What I wanted was for this to be easy — for the revenue from the memberships and t-shirts sales to amount to something that, when combined with the money from a modest dose of advertising, would clearly constitute a reasonable full-time salary.

But there’s a reason why you can’t say, “Wow, look at all those people supporting their families with their weblogs devoted to deeply intricate Mac and web nerdery,” or, really, why there aren’t that many people supporting themselves full-time from their weblogs, period. That reason is because it isn’t easy.

My desire for this to be easy bound me in a catch-22, where I felt like membership wasn’t going to grow large enough unless I could put full-time effort into producing the site, but I wasn’t going to be able to put full-time effort into the site until the membership revenue was large enough.

What I’ve concluded, though, is that if I want to make a full-time income from Daring Fireball, I need to just do it full-time. I.e. that it’s not going to work the other way around — to wait for the revenue to burgeon and then start putting full-time effort into it.

There’s nothing I want to do more than this. But even so, it has been an extraordinarily difficult decision to make, partly because I’m so prone to over-thinking that I sometimes have trouble deciding what to have for lunch, but mainly because there exists the very real possibility of failing in an excruciatingly public way.

That raises the question as to why I didn’t just do this without announcing anything. I.e. just try putting full-time work into the site without announcing anything, and see how it goes. But that, more or less, is just as cowardly as the original “just keep growing the revenue until it’s enough and then slip on over” plan.

I see no way around telling you, the regular readers of this site, what it is that I’m trying here. To lay it all on the line. The point here isn’t to guilt anyone into buying t-shirts or becoming a member (e.g. Oh, man, Gruber quit his job, I better help him out). The point is to prove to you how much better Daring Fireball can be than it has been, and how much more you, the readers, will enjoy it, now that I’m devoting my time to it.

Here’s an apt quote from one of my personal heroes, Stanley Kubrick:

“If you can talk brilliantly about a problem, it can create the consoling illusion that it has been mastered.”

Point being: Dithering about this for another couple of years isn’t going to solve anything. It would be better to try this now and fail than to endlessly deliberate over plans that are never put into action. I need to just do it, and so I am.

Don’t Settle

This is going to sound really corny, as in like literally groan-inducingly corny, and if you’re a regular reader of this site and a fan of my writing, it is, I hope, very clear that I have a deep, perhaps even pathological, aversion to corniness.¹

But part of what’s inspired me to go for this is that a few weeks ago, I finally got around to listening to Steve Jobs’s Commencement address at Stanford last June. It’s a great speech, and Jobs, famously, is a great speaker. The transcript doesn’t really do it justice. Commencements are inherently corny affairs, and it’s doubly-corny for an avowed Mac nerd to cite Steve Jobs as a source of inspiration, but when Jobs spoke of his diagnosis of pancreatic cancer and the day he spent under the assumption that he had just a few months left to live, I found it genuinely moving. And when Jobs spoke about his work, I was inspired:

Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work, and the only way to do great work is to love what you do. If you haven’t found it yet, keep looking, and don’t settle. As with all matters of the heart, you’ll know when you find it, and like any great relationship it just gets better and better as the years roll on. So keep looking. Don’t settle.

This advice isn’t anything you can’t hear from a high school guidance counselor, but somehow there’s a difference. I don’t think many high school guidance counselors actually love what it is that they’re doing; Jobs actually means it. Some words sound like tripe because they’re overused by people who don’t actually mean them.

Daring Fireball is what I love to do.

One point I want to impress upon you is that the proper response to this announcement isn’t so much “Congratulations” as it is “Good luck, I hope it works”. Success is far from assured, and I’m feeling more than a little gut-wrenching uncertainty.

It’s difficult for me to write this sort of thing, to step out from behind the curtain and address you, the reader, directly — as I wrote two years ago, “Just me, your humble author, hat in hand, heart in throat, asking for your support”.

For those of you who think this is worthwhile, however, that’s what I’m doing: asking for your support. And I don’t know how to do so otherwise.