In no particular order. Your mileage may vary.
1) If you’re wondering about going indie, consider your lifetime fiction output. General rule of thumb — from a man I trust to know his business — is that “entry level” competency is reached when you have at least 500,000 words of books and stories in your trunk, and/or have several personalized rejections from trad pub editors. Prior to that, you may not have done enough “homework” to have your storytelling muscles up to the task of surviving in the indie marketplace. I know plenty of people immediately publish everything they’ve ever written, ever. I sometimes think that’s a mistake. I know I will get beat up for saying this.
2) If you’re wondering about going trad, consider your ability to withstand rejection. How long are you willing to wait for the editors/agents to decide you’re good enough? Keep in mind: waiting is not necessarily a bad thing. In my experience, breaking into trad pub print was one of the most satisfying events of my life. But I am from the old days, when the two options for authors were: outlast the gatekeepers, or shame yourself with vanity print. Anyone who has been through any kind of selection process — in any arena — will understand the joy of passing a tough bar. Just because it’s tough, doesn’t make it irrelevant. Although the tastes of many agents and editors can often seem wildly out of sync with the marketplace.
3) Editors and agents are not mind-readers. They cannot see into the future. There is no guarantee what will be a hit, or a dud, until it’s either a hit, or a dud. Some agents and editors develop reputations for “making” big-market talent, but this is akin to panning for gold: you have to devote a lot of time to sifting through silt, sand, and mud, just to get the little flecks and small nuggets of gold. In the words of one Hollywood producer, nobody knows anything. Ergo, the hits and the duds happen as they happen — and the one who ought to be a hit, isn’t, while the one who ought to be a dud, also isn’t. “Failure” in trad pub may have nothing whatsoever to do with the author or the stor(ies) and everything to do with events beyond an author’s control. Which is perhaps the #1 glaring flaw of trad pub that drives so many people to indie in the first place.
4) But indie isn’t an instant road to cash and fame, because now the slush pile is the whole world. Millions upon millions of books and stories being shoved at the audience, with fire-hose force. Standing out in that torrent, can be just as much of a chore as waiting in line at the gatekeepers’ transoms. You aren’t guaranteed anything. No matter how zealous you may be about the mode of delivery. Yes, indie grants the author full and total control, from start to finish. As well as the lion’s share of the take. But this also imposes the lion’s share of the responsibility. And if you thought it was painful waiting on editors and agents, it can be equally painful waiting on the audience at large. If you publish an indie book in the forest . . .
5) Don’t go cheap on covers. I know I am cutting against the grain with this. But seriously, don’t go cheap on covers. You want your cover to look like the trad pub covers that caught your eye when you were just a reader. Most artists will license an extant piece of artwork. May cost you anywhere from $200 to $500 dollars, which is stunningly inexpensive, considering that some of these men and women have done posters for Hollywood and done famous works which are known across the industry. I know many indie authors are poor as church mice, but still, don’t go cheap on your covers. You have a vanishingly short period of time in which to capture a prospective buyer’s attention. Pouring your heart and soul into a manuscript, then spending an hour on a free, terrible cover that you kludged yourself — with poor photoshop skills — is like devoting months of hard work to your diet and the weights at the gym, then going to the beach in dingy, grease-covered auto shop coveralls.
6) You can do everything right — according to the pattern established by your successful friend(s) — and still get bupkus. This is because the market is not a science. 1 + 2 does not necessary equal 3. It can equal 10,000 or it can equal zero. Consumers are legion, but they are fickle. They want a “sure thing” and herd dynamics dominate in every corner. Mountains of marketing advice is put forth, regarding ways to “game” the herd dynamic: get your product viral, so that the inertia of talk is on your side. When people are buzzing over your novel, especially if this buzz tends to self-reinforce as buzz-about-the-buzz, you can rake in wads. But there are still no guarantees. Like fishing. You can have the same type and kind of lure as your buddy next to you in the boat, with the same rod, same reel, same everything, and he will catch a dozen, while you reel in just one or two. Or none. And you have to be prepared to live with this. Pick yourself up off the hot pavement. Go wash your face and your hands. Then try again. And again. And again. And if this sounds way too hard for way too little return, there are 101 careers which serve as far easier paths to far better money.
7) So don’t quit your damned day job. Seriously. Do. Not. Quit. Your. Day. Job. It sucks trying to write full-time and work full-time. It sucks more not paying bills and being forced out of your house or your apartment. It sucks even more depending on the good will of your relatives, or your church, or government programs. If I had $10 for every embarrassed pauper author who proudly proclaimed, “I am a full-time writer, so fuck you,” and then (s)he went back to begging for lunch money, I wouldn’t have to work anymore. Starving artistry is not a holy calling. Really, it’s not. I know I am gonna get burned at the stake for saying it. But seriously, do not check out of the “mundane” work force. Not unless you’ve got a metric ton of dough in the bank, or you’ve got a spouse who eagerly volunteers to carry the mundane load — while you labor at the desk in the attic. But if you’ve got responsibilities to meet, and mouths to feed, please, meet them and feed them. As Steven Barnes said at Norwescon ’07, suffering for your art may be noble, but making your family suffer for your art, just means you’re an asshole.