The world is loaded with stories of people’s successes, either autobiographical or second-hand, and the supply barely keeps pace with demand. People are addicted to hearing success stories and endlessly study them for things they can do to ensure they succeed at some endeavor. Of course, a lot of people only see the easy tricks, and avoid the difficult ones. Hemingway wrote 500 words a day, but he also drank like a fish. The latter is the easier option, though you can quaff all the Papa Dobles you want, it won’t produce A Farewell to Arms unless you sit at the typewriter. Sober.

Technology companies, small and large, do the same thing. It’s easy to keep an eye on the competition and just duplicate the hot new feature, web design technique or monetization strategy that the hot new product on the market is using. “If it worked for them it will work for us” seems to be the line of thought. How many people think the potential costs of implementation through? When you’re chasing the right new feature or monetization technique, it can often become a distraction from the real, core product that people were interested in from the start.

This isn’t to say that there isn’t value in knowing what helped other people to succeed, but so many of the lessons boil down to simple, repeatable axioms: “Write every day,” “Cultivate multiple revenue streams,” “Focus on your key strengths.” These are all fine and dandy, but the key is in how you implement them. Success doesn’t come from just plucking other people’s good ideas out of context and mixing them into some sort of magic elixir that will guarantee you profitability. The piecemeal approach ignores the external factors that were the real reason something succeeded. It’s pure magical thinking to assume that what worked for Ernest Hemingway, or for Facebook will work for you.

It also ignores the countless failures that litter the path around us. There’s plenty more that we can learn from those who came before us, stumbled, and fell. Odds are, you’ll come up against the same problems. Knowing what happened can tell you what not to do, or at least prepare you for the inevitable choices you’ll have to make. Of course, the current environment doesn’t encourage stopping to poke around the corpses lying along the path. When the mantra is growth and profit at all costs, taking the time to figure out the right strategy costs time, and time is money—often someone else’s money in the tech world.

The people out there who are selling the reagents we mix into our magical elixirs of success are often the only ones who come out ahead. Better for us, as a whole, to stop worshipping the cult of emulating other people’s successes, and focus instead on improving the strategies we use to do the things that we want to be successful at. It takes trial and error. There are no shortcuts. It just takes a willingness to commit, be comfortable in the face of the unknown, and the confidence that the right decision will trump the fast decision.

We’ve all grown rather impatient in the Internet age. Apple, who released “revolutionary” products in 2007 and 2010 with the iPhone and iPad, respectively, have been endlessly criticized for not putting out another revolutionary product in 2008, 2009, 2011, 2012, and 2013. People are screaming at the developers of iOS apps to release a new version with an iOS 7 style user interface and icon. [1] We gush over Samsung putting out a smart watch before Apple, and only just temper our gushing when the product comes out half-baked, at best. Everything needs to be done and ready yesterday. Web app add new features, then bang at them to get them mostly working if they’re not distracted by the next shiny object.

This may be a function of the instant feedback we get from our technology. If you’re not sure if an idea to improve a product comes to us, you can quickly hack up some basic functionality, and test it out on audiences. A/B testing of copy, button placement, and even prices is common among startups and established companies alike. Leveraging the instant feedback and data collection we have access to improve a product or maximize revenue is not a bad thing, but it gets fiddly, and can be a distraction from making the actual product as good as it can be. When you rush something out the door with fundamental flaws that you might not even know about until it’s being hammered by real people, no amount of A/B testing will fix the underlying issue.

On a recent episode of CMD+Space, Chase Reeves described how he takes a few days when creating a new design or product to just let himself go crazy before finding the right place to focus. It reminded me of On Writing, Stephen King’s memoir and guide to the craft of writing. There, King suggests putting a completed draft in a drawer for six weeks, so that when you go back to edit, you see it with fresh eyes. In technology, you often don’t have that luxury, but if we can squeeze in a little time for reflection before adding a new feature, implementing a new pricing strategy, or even changing the focus and priority, the perspective of distance can often change how we see something compared to when we’re in the heat of the moment. It’s easy to get caught up in what “everyone else” is doing, or whatever may be the hot trends out there to catch up on. They’re easy answers to hard and complicated problems, and easy answers are rarely the best.

This is why there’s something to be said for taking your time and getting what you want to put out into the world right, over getting it out fast. Apple is the king of this. They release products on an (usually) annual cycle of incremental revisions, but only create new product categories when the first thing they can put out is up to their standards and done “right” in their eyes. We had touch screen smartphones and tablets years before the iPhone and iPad, but those two products, because of their long and careful gestation, got right what those previous ones got so wrong. In both their wakes, competitors products tried to glue the things the iPhone got right to their products to make them competitive, missing out that what made the iPhone and iPad “right” was the holistic combination of hardware and software, not just adding features for the sake of having them.

So, what makes something “right”? This is a subjective thing, but the best way to be sure your choices are actually right is to be true to a promise and a goal. Are you trying to create a tool for developers to collaborate on code? A forum that allows people to ask others developers for help with their project might be a great additional feature. It drives growth and engagement, and keeps everyone under one roof. However, it comes with costs—you have to have people administer the forum, deal with spam and trolls, and spend time integrating it with your existing infrastructure. Are the benefits of this new feature going to be worth the distraction from the core product? Think about it. And take your time.

One of the things most bemoaned as we become always-on and always connected is that the line between work and private life are being blurred into non-existence. The nine-to-five job’s been dead for years, and if you’re working for a company that offers “flex time” or is “results driven” with no set hours, it only compounds the problem. People are quick to point fingers. Some point to the enabling influence of technology: the smartphone, high-speed Internet, e-mail. Others point to companies that leverage those technologies to impose themselves on workers without paying them more. These are not mutually exclusive, and these are not the only answer.

As someone who works in the high-pressure world of a technology startup, and in a social media community role—the sort that’s “always on”—I only went in with the plan that I would establish hard boundaries to keep my personal life and personal work separated from my job. I don’t know if I’ve fully succeeded, but I do believe I’m in a better position than I would be had I allowed myself to be at the beck and call of the job from the start. That separation began on day one, when I got setup with my work computer.

I insisted outright on having a separate machine at work, and fortunately there was an iMac that a former employee had bee using. By not bringing my primary machine, a laptop, to work every day (or indeed, ever), I immediately established one strong bulwark between “work” work and personal work. I know that when I travel to the office and sit down at my desk in front of the vast expanse of a 27" iMac, I am at work. Nowhere was this reinforced more then after Hurricane Sandy here in New York, when I was the only person who actually came to the office after the subways started running. For two days, everyone else worked from home, while I held down the fort in person. While I’ve occasionally used my home machine for work when I couldn’t otherwise get into the office, it’s an exception and never a rule.

The second hard barrier is email and other communication. As I work for a small company, we typically don’t use the phone for much, except in emergencies, so I know that if I get a call from one of the bosses and I’m not in, it’s legitimately urgent. Instead, a large amount of our communication occurs through email and chat. When I’m away from work, I log out of our intra-office chat application, on both my work machine, and my phone, and so it stays until the next morning. If someone tries to get ahold of me in the chat, I get an email notification when I check my work email, which I typically do with Mailbox.

Mailbox is, without a doubt, the best thing to happen to email. If I get a work-related message, and I’m off my self-defined clock, I can defer it until tomorrow morning with just a swipe and a tap. I don’t even have to think about it. I’ve even given thought to actually taking the work email off of my phone entirely, but it’s come in handy to fire off quick status updates and share work-related intelligence I get from my off-time reading. Of course, it almost goes without saying that I’ve turned off all push notifications and automatic email checking. [1] If it’s that urgent, a phone call or text message will do.

For various online services, there is some overlap. I keep our Google Apps calendar subscribed on my iOS devices and laptop, so I can keep track of important events. I keep a Work notebook in my Evernote, and my OmniFocus database contains an @Office context, and a folder of work-specific projects and actions. As I mentioned above, I keep the chat application we use in the office on my iPhone—on the first screen, no less—and I also installed an app so I can check in to our bug and task tracking app. The Google Drive app on my iPad is tied explicitly with my work’s Google Apps account, and I have HootSuite installed for work-related social network stuff. It’s the only social stream app I keep on my iPad.

This is all fine, because I know where the lines are. Things are clearly delineated. In fact, the second home screen on my iPad is set aside just for work-related apps, all eight of them—and that’s stretching the term “work-related”. I know the barriers I’ve set up between my work life and my personal life, and my co-workers know them too. Only I know the openings (for now), and I suspect it will stay that way. The porousness of certain barriers will never be fully closed, I expect, but as long as our work lives are going to defy being defined by a clock, we will find ways to deal with that porousness on our own terms.

It was a little over two years ago when I stepped on a stage at Johnny Brenda’s, clad in a white Tyvek jumpsuit with red duct tape accents, and a red flower pot like hat on my head. I stood in front of a crowd of drunken onlookers, raised my right arm, and proceeded to flail my arms like a madman to a sixty second clip of “Be Stiff” from DEVO’s 1981 live EP. It was my first air guitar competition. Yes, this is a thing. I’ve competed three times since, once more in Philadelphia in 2012, and twice this year in New York. Each time, I’ve made failed to make it past the first round. [1]

The best I ever did was my second year, performing DEVO’s “Girl U Want”. I scored a 5.7, 5.7, and 5.0—one judge claimed my track was a “keyboard based song” and docked me (in)appropriately. After a dalliance with changing my stage persona and performing some David Bowie, I tried to replicate my success by doing “Girl U Want” again, only to end up with the same middling scores I had earned a week before. Even while I was up there, going through the motions, I felt something was off. Perhaps it was the lack of rehearsal—it had been just over a week since the previous competition—or perhaps it was too many beers and not enough to eat. Either way, I knew I could and have done better.

As it stands right now, I’m a weekend warrior. There’s folks in the US Air Guitar scene who have been competing for years, and consistently kill. It’s not about the song, or the crazy costumes—though costumes help with stage presence—it’s about impressing the judges and nailing your routine. It’s about melting faces off. It’s about being really good, and being entertaining to watch. This is why the best judges for air guitar competitions are other air guitarists. They know what they like when they see it, and they can express it properly. It may be couched in a bit of verbal abuse, but that’s part of the show.

This came into perspective as I started diving into the book So Good They Can’t Ignore You by Cal Newport at the behest of Merlin Mann on his recent solo episode of Back To Work. The book’s premise is twofold. First, the idea of “following your passion” to find the career that’s right for you is bullshit. Second, by developing rare, valuable skills—what Cal refers to as the “Craftsman Mindset”—you can parlay those into a career that you will enjoy—you just have to put the time in for it. One of the first people Cal talks about to illustrate his point is Jordan Tice, a twenty-one year old bluegrass guitarist of some renown.

Music is one of those things that people pursue out of passion, but there’s more to Tice’s success than simply loving bluegrass guitar. It’s his dedication to the craft of playing guitar, reaching the outer limits of his skill, and banging away at a difficult lick until he can play it as fast as possible with no mistakes… then trying to do it again, even faster. It takes Hours upon hours of dedication and practice. It’s a tactic that appears time, and time again in the book, from Steve Martin’s ten years honing his act to the outer limits of stand up comedy (and forty years practicing banjo), to Ruby programmer Giles Bowkett stretching the limits of the programming language to create an application that generates dance music, and Cal Newport’s own practice with understanding difficult Computer Science proofs.

What does this have to do with playing air guitar? Quite a lot. Focusing on skill acquisition, practice, and relentless improvement in any sort of field where you’re up against other people certainly can’t hurt your chances. Air guitar competitions are only a small, and somewhat absurd example. I don’t see myself making air guitar my life’s work, but my recent experiences, along with Cal’s book have inspired me to take the endeavor with a bit more seriousness for 2014’s competition season. It’s also had me thinking about how I approach all the other endeavors in my life, personal and professional. Being willing to bust my ass at my craft, be it what you see on this page, my role as a Community Lead with Trusted Insight, or just playing air guitar in my bedroom, it’s all building career capital that will serve me in the future, one way or another.

I recently came across a piece by David Lowery, of Camper Van Beethoven fame. The title summarizes the entire thing, so pull quotes aren’t really necessary: “My Song Got Played On Pandora 1 Million Times and All I Got Was $16.89, Less Than What I Make From a Single T-Shirt Sale!” This sort of thing isn’t a new cause for David, he’s on about this before, and though the post on Spotify is new, talk about Spotify’s low payouts to artists is not. It was even discussed on the second episode of Crush On Radio.

This serves an odd counterpoint to the growing emphasis placed on building “content” and making money online. People have access to more media now, than at any point in history. There’s also more media now, than at any point in history, but it’s increasingly easier to get ahold of it, and that’s where things get interesting. It’s a truism that the Internet provided a low cost, low overhead means of content distribution before it provided any good means of paying for said content. Though now we have a payment infrastructure in place, and people are buying music again, file sharing and torrents are still a thing. [1] We have so much stuff out there, begging for our attention, that we have an oversupply situation on our hands.

Basic economics tells us that the value of something is determined by supply and demand. If there is a limited supply, and a high demand for a good, then the price should be high. Conversely, if there is a huge supply and minimal demand, the price should be lower. This isn’t so much ECON 101 as it is ECON 081. In the case of online media and content, it seems we have the problem of there being constant demand, but an extreme oversupply of content, combined with distribution and revenue models that come from the days when the media a lot of this stuff shipped on was fragile, expensive, and difficult to produce.

In the case of streaming services, a chunk of the blame must be laid at the feet of the recording industry, charging ridiculous licensing fees, insisting on restrictions to prevent users from recording the stream [2], and keeping a disproportionate share of the pie for themselves by any measure. Also, too, is that the streaming services still have to compete with free. Sure, you can listen to Pandora, or Spotify for free, but you have to put up with advertisements and song limits. Meanwhile, you can queue up a playlist of songs from YouTube—yes, YouTube—and listen to music forever.

With so many musicians out there competing for the attention and cash from a fickle audience who can get the latest release by even the indiest of indie bands for free, no wonder it’s getting harder and harder to make an honest living with your music. But this problem extends far beyond music. If you produce any sort of media that can be reproduced digitally, the music world is the proverbial canary in the coal mine. There’s so much stuff out there, so little time, and audiences so very fickle, that it’s beyond difficult to gain traction, and make any money, let alone a living. It’s certainly possible. Jonathan Coulton made a cool half-million dollars in 2010, but his story is far from typical. Yet, whenever a discussion of paying for media online comes up, and fingers get pointed, a certain group will always pipe up and point to those who “made it” by giving stuff away for free.

The survivorship bias colors our thinking. We don’t hear about the failures much, and when we do, we dismiss their arguments as sour grapes. When someone new to the game tries to emulate what worked for someone successful, fails, and goes “That’s fine for Radiohead! They have a huge fan base,” we so often miss the point. If having 1000 true fans is what you need to succeed, how do you survive long enough to get that number? There’s the safe bet of keeping your work a side project while holding down a day job, but that makes it harder to do the work. Or, you could throw yourself into the work, and risk losing everything. Are the only people left who can become full-time creators going to be those who have a safety net of wealth, and a sinecure waiting with their father’s firm should their artistic endeavors fail?

It’s a question worth asking: how does one make content and make a living in a world where content is devalued? Even if you’re so good they can’t ignore you, they might not even get to you because of the glut. If you, the reader, take anything away from this piece, take away this: there is no simple solution, and anyone who proposes one is either naïve or trying to exploit someone else. Too many free-culture wonks fail to account for how an artist is supposed to feed themselves, and too many industry wonks are either desperate dinosaurs who want to charge $19.99 for a piece of plastic again, or middle-men who see an opportunity to pick a two pockets at once. Whatever the answer is, I don’t have it. We’re all going to have to bang our heads together on this one.