The Blessings of the Coworking Space


I come from one of those families where missing a sibling’s high school graduation gets you tried for high treason. If we’re talking about missing graduations for graduate degrees, you may face summary execution without a trial. This, and other family obligations, results in a situation where I’m often traveling. Add in travel for business and I feel like I’m always on the road — especially when I need to get work done.

When I’m planning a trip, one of the first steps I take is to search for what coworking spaces are in the area. I’ve worked at a whole slew of coworking spaces now (and a few places that weren’t precisely coworking spaces but would rent me a desk for a few days). I’m a true convert to the church of coworking, particularly on the road.

Coworking’s Appeal on the Road

I used to try to work in hotel rooms when I traveled. I recommend strongly against doing so, even if you’re only planning to work for an hour or two. At the very least, I will always choose to go to a coffee shop to work.

The chairs in the typical hotel room are not comfortable for working at a computer for any length of time, even if you’re lucky enough to get a room with a desk and an office chair. None of it is particularly ergonomic and, if you spend as much time in front of a computer as I do, too much time in a bad chair has a noticeable impact on my mood and ability to work. Add that into the less-than-ideal internet access some hotels offer and it’s clear why I’m out the door as soon as possible.

Coworking spaces offer a lot more than the typical coffee shop and I never feel like I’m squatting. Many spaces have a day rate that’s about equal to the amount of coffee I’d have to buy to work all day at a coffee shop and I don’t wind up jittery as a result of too much caffeine. As an added benefit, I get to meet locals and hear about what they’re working on — an invaluable add-on for someone who’s always looking for story ideas!

The Mix of Ideas

Particularly for those of us who work in such a way that we don’t have to interact with people on a regular basis, coworking spaces are a blessing. They’re a low risk-opportunity to interact with people and ensure that our social skills don’t atrophy. Even for introverts, talking to people is a necessity: without that diversity of connection, it’s harder to form new ideas or pursue new projects.

I can’t count the number of times I’ve been sitting in a coworking space and struck up a conversation with someone nearby with an entirely unexpected result. I’ve connected with people who I’ve been able to interview later on, who have needed my skills right when I happened to be handy or who have just wanted to go grab coffee. In terms of the ability to connect with people, I compare working in a coworking space to the best parts of attending a conference: I’m able to meet a bunch of new people with somewhat similar interests in person.

The low-risk aspect of this mix is particularly important to me. If I’m just sitting around and talking shop, I don’t want to deal with anyone who is going to think I’m crazy for not having a day job in the first place. I get enough of those conversations as it is. Anyone working out of a coworking space has similar basic assumptions about work that I do, like not necessarily needing a traditional 9-to-5 to do well. Of course, just because someone is sitting in a coworking space, our opinions won’t be identical — and that’s the fun part. I’m just after avoiding conversations where the entire concept of what I do is foreign.

Why I Don’t Currently Belong to a Coworking Space

You’d think that with all my love for coworking spaces, I’d be a full-time member somewhere. I’m not, currently.

There are a lot of factors in play:

  • Logistics: With all the time I spend traveling or otherwise unable to go into a local coworking space, there is rarely a month where I could get my money’s worth out of membership. If I could pay for some sort of pass or membership card that gave me access to all the different coworking spaces I land at, I would go for it in a heartbeat. Bring me a pay-as-you-go coworking scheme and I’ll be happy.
  • Pickiness: I am exceptionally picky. None of the coworking spaces near me are exactly where I want them to be located, offer precisely the combination of amenities, or are otherwise perfect in every way. This sheer, unadulterated pickiness has lead me to almost start my own coworking space twice.
  • A Good Home Office: I already have a pretty decent set up in my home that I know I work well in. I head out of it on a regular basis and have no problem getting a day pass at a coworking space or working from a coffee shop as needed, but I don’t need a permanent home for my work elsewhere.

I get my coworking fix on a regular basis, even without having a standing membership. I’m willing to guess that sooner or later, I will join up with a coworking space on a more regular basis, but for now, I’m comfortable looking at the many options on the road.

Image by Flickr user Rick Turoczy

How Much Infrastructure Do You Need to Build to Get Where You’re Going?


You can work without infrastructure. Some people compare it to an acrobat working without a net, but it’s more like an acrobat working without the rings, high wires and other apparati that makes an act more interesting. An acrobat can still do plenty of flips and other tricks without the tools of her trade, but avoiding audience yawns is significantly harder.

The same goes with practically any business. I’m always surprised by what people can do with their bare hands and an awful lot of time. But the moment you give someone the right tools, everything’s easier, quality’s higher and she may even wind up with some spare time. Infrastructure, whether it’s the customer relationship software that makes it easier for you to sell your products or the note-taking app that manages all the little details of your life, improves your ability to get good work done.

It’s hard to argue against infrastructure. But actually getting the right infrastructure isn’t always as simple as making a trip to the corner store.

Custom Infrastructure Versus Off-The-Shelf

One of my problems with finding the right infrastructure is that I can never find exactly what I want — a content management system doesn’t quite match the vision I have or a survey tool doesn’t have enough flexibility in the types of answers it accepts. I get caught up in tweaking a tool (or even building an entirely new tool) so that I can have exactly what I believe I need. I’m not exactly the best at working within the constraints of a system.

It’s a bit of a trap, though: building your own infrastructure can take a lot of the time that you might otherwise invest in actually going out and getting started on what you want to accomplish. Sure, you may be able to turn around and sell that infrastructure to someone else, provided it isn’t too customized or it isn’t the secret sauce that sets you apart from the competition. That route has built plenty of fortunes — think about the oil booms. The people who are guaranteed to turn a major profit when everyone is out looking for oil are the guys selling the drilling equipment. Infrastructure is almost always a good bet.

But it can also slow you down if you’ve got a great idea that you need to get to market. You can distract yourself with perfecting the infrastructure when you should really be pushing full speed ahead, even if you have put together a patchwork approach to managing the whole thing until you get it to market. On the other hand, there are projects that you may pursue that the infrastructure just doesn’t exist for yet. If you can’t buy an off-the-shelf solution and cobbling together existing components won’t get you where you need to be, you have to find a way to balance that problem against actually accomplishing what you’ve set out to do.

How Much Infrastructure Do You Really Need?

It can be tempting to keep looking for the best tools. You can get bogged down in the details and never actually getting around to building the business you’ve planned all this infrastructure for. It’s a dangerous pit to fall into, another temptation that can drag you down.

I get bored with my infrastructure, which may seem like an odd thing to say. But I am excessively fond of playing with new tools: some people collect stamps, while I collect web apps. If I let myself, I could spend all day every day trying out new combinations of tools, without making any progress on the projects that I actually consider important. I’m not the only one, either, at least among the types of people who haunt productivity blogs. The only option in a situation like this is to draw a line in the sand for yourself. You can tweak and test and tinker to a certain point, but no further.

It doesn’t seem like a bad thing in the moment, though. I cannot begin to describe how much fun I get from tinkering with my workflow or building a custom tool. It’s a fast way to lose hours that I meant to spend elsewhere, but it’s easy to justify with the idea that if I can just find the perfect workflow, all of my work will do itself and I can kick back.

But I’ve had to find a stopping point in that eternal search for the perfect approach to work and — if you want to actually get any of your work done, you’ll need to as well. Make it clear to yourself under what circumstances you’ll return to the search: since I tend to write about workflows and related topics fairly regularly, I’ve divided the question into when can I try out a new gadget or app and when can I make major changes to how I work. Respectively, those times are when I can line up a place to publish a review in advance and no more than once a year.

Revisit Your Infrastructure Reasonably Regularly

Google recently announced that Google Reader will be shuttered later this year. As it happens, Google Reader has been a major component of my workflow for years. I have obsessively created an organizational system of all sorts of RSS feeds. I have layers of plugins that automatically act on the items I star and tag. I even have a carefully considered guiding document on what is worthy to make it into the one folder I read religiously every day. The end of Google Reader is going to leave a major hole in my infrastructure.

That’s given me a reason to start going through the many other RSS readers currently on the market. I’m pretty upset about the end of Google Reader, but I’m having some fun trying out all the different alternatives that have evolved since I last really investigated RSS readers. I’d considered the matter a solved problem and haven’t revisited it in years because I knew it was something of a rabbit’s hole I could fall down.

I try to keep from tinkering unless there’s a particular problem with my existing set up. Optimizing the tools I use isn’t enough of a problem to spark an investigation into what other options are out there (unless it’s been a really rough week and I need some cheering up). It seems like waiting until something goes wrong could be dangerous — after all, you could wind up using less advanced tools than the competition. But considering how often web apps disappear or an upgrade removes a feature that I rely on, I’m pretty comfortable with the speed at which I try out new options.

Infrastructure is a Learning Experience

I do make a point of learning about new options long before I try them out, though. I want to have a more limited field of possibilities before I dive into trying out a bunch of things.

But it’s worth going even further when learning about infrastructure at an even deeper level. After all, if you know what makes your tools tick, you may be able to tweak them yourself. There are different layers to this sort of learning: just going a bit deeper than the typical user’s experience in a given piece of software can be great — just being able to install a plugin on top of a given piece of software will put you ahead of the game.

I’m becoming a bigger proponent of learning how to hack on existing software, even if you’re not prepared to devote yourself to learning all about a given programming language. Just knowing a little bit about what is possible and what isn’t can make it easier to find someone already doing all the hard parts — or to gear up to building your own infrastructure yourself. I won’t declare that everyone under the sun needs to learn how to code, design, write or otherwise create, but the more of these skills you have, the more infrastructure you can build or adapt to your own needs.

After all, isn’t having the best possible set of tools the ideal? That we have the right infrastructure to speed up everything that we want to do?

Image by Flickr user Pinguino K

What Makes an Ebook Really an Ebook?

When is an ebook better than a printed book? When it includes resources that a physical book could never provide. I picked up a copy of The MacSparky Markdown Field Guide (an excellent resource for anyone using Markdown) and have been thinking about what really constitutes an ebook ever since.

I opted for the PDF version of David Sparks and Eddie Smith’s ebook. The PDF version is actually the secondary option, though, with the iBookstore version taking precedence. I prefer PDF for flexibility, despite being one of those people who mostly buys their hardware from Apple.

The reason that the iBookstore version might be preferable is because of the sheer amount of non-written content built in to the ebook. Every section seems to have something in addition to some very well written content, like a screencast or an audio interview. The same multimedia content came along with the PDF, though it isn’t embedded in the document. All in all, The MacSparky Markdown Field Guide weighs in at 130 pages, one and a half hours of video and one hour of audio.

We all have a working definition of a ‘book’ as a bunch of written content, perhaps with some images thrown in. But what happens to that definition as we shift over to reading our books on devices that make integrating video and audio content extremely simple? I wouldn’t be surprised if the definiton of books expands to include most types of content, though I’ll be very surprised if the word disappears from use — there’s a few too many of us bibliophiles out there for that.

On the surface, I love the idea that I can have all sorts of media in my reading material. But I want more data: how easy is it to process this mix? I shift back and forth pretty easily, but I spend all day glued to a computer monitor. For some readers / watchers, I could see this mix being very helpful, but for others I could see it causing distractions. Integrating more materials could change the interpretation of books: if there isn’t a video about a certain section, it clearly couldn’t be important. I know I get hung up on points in given books that the author may have included as a throw away. Will those points get lost.

I found The MacSparky Markdown Field Guide incredibly useful. I don’t expect to have answers about the right way to integrate media content for quite a while, but it’s a topic worth paying attention to. We’re going to see more examples every day, for the near future.

The Very Real Appeal of Random


For all that we can spend hours searching for exactly the right item to buy, the appeal of buying something random is always there. When a site like Woot offers up random items to its audience, the sheer number of people willing to put down money for a box without any hint of what will be in it is incredible. Woot’s ‘Bag of Crap’ sales sell out within seconds and have even been known to crash servers.

Randomness is appealing, on a level that we don’t always expect. Of course, we don’t like all surprises — receiving something in the mail that we can’t track back to an original sender is more likely to feel creepy than exciting. But when that unexpectedness is balanced with a little forewarning or explanation, it can be a very good thing.

An Element of Trust

More and more successful businesses have a few bits of randomness built in. Consider the genre of subscription services that now mail their customers a box every month or so — without saying exactly what will be in the box ahead of time. Quarterly Co. is among the leading lights in this new field: the company puts together packages of items chosen by relatively famous contributors and mails them out to subscribers. I say ‘relatively famous’ because they include bloggers with large followings, CEOs that may not be well-known outside of their own niche and other ‘internet famous’ types. The mechanics that Quarterly Co follows mean that every three months, subscribers to a particular curator get a box in the mail — they don’t know what’s coming, but have some assurance that it’s awesome. It’s even possible for a person to subscribe to multiple contributors and get several bits of random on a regular basis.

Quarterly Co. has rapidly become very popular in certain circles: while the company doesn’t make too many details available, but even early on the company reported that it was adding new subscriptions every five minutes. I can only assume that speed has increased since then.

The reason for Quarterly Co’s success is not necessarily obvious. Sure, they’re offering what amounts to a gift box full of cool stuff from cool people on a regular basis — and who doesn’t like that idea? But the ease of trust that Quarterly Co. provides is crucial to the process. It’s simple to trust the company: they’ve clearly done this sort of thing before. Even better, Quarterly Co’s presence in the process means that the crazy artists and other creatives they’ve enlisted are going to send things that are appropriate. If I were to subscribe to someone whose name I’m familiar with, I may also be familiar with any pranks she’s pulled in the past. I might have some questions about the quality of the items a person might curate. Quarterly Co. eliminates any concern I could have in that direction.

The Surprise Business Model

While Quarterly Co. is taking a broad approach to what can be included in its subscriptions, offering some well-defined surprises is now a business model. My husband gets a package every month with five new inks for his fountain pen. He knows that he’ll get ink every time, but the colors and manufacturers are always a surprise. They aren’t randomly selected, but because there’s no interaction with the curator, the choices always feel a bit random on our end.

But these random selections lead to some good things, especially from the point of view of the ink seller who put together the ink subscription. As my husband has tried out a whole bunch of new inks, he’s found plenty that he wants more than the small sample that he’s already got. Not only is the subscription a money-maker, but it leads directly to follow up sales.

There are similar companies that send out samples exclusively in their packages, partnering with relevant companies to get products for free. There’s some serious flexibility in this business model in how someone can make money — and there’s plenty of business to be made. If you judge just based on the number of times a week I have to talk myself out of a new subscription, the companies involved barely have to work to make sales.

The Negligible Price Point

One of the reasons that these subscription services succeed, as well as other products that are sold with some randomness built in, is because of the low costs. We, as buyers, can’t justify paying high rates for something we don’t know we’ll be able to use or enjoy. We can, however, justifying a little bit of fun money for the right bit of randomness.

Quarterly Co. is at the higher end of random pricing, going occasionally as high as $50 per quarter. My husband’s inks are $10 per month (which is very cheap for the quantity of ink, if you don’t have a fountain pen addict in the house to set price points by). These companies target audiences for whom $10 or even $25 a month is easily forgettable. It’s almost low enough that the buyer can convince herself that a random package showing up is really a gift. And while I wouldn’t get a family member a ‘Bag of Crap,’ I would happily pay for a year’s subscription for some of those hard-to-shop-for relatives.

I’m well aware that an extra $10 per month isn’t a negligible expense for many people. And subscribing to multiple offers takes that amount higher very quickly. But for those demographics with higher incomes, buying something random can be seen as getting a surprise gift. Keeping those low price points are an excellent move, especially for anyone who can either get products inexpensively (or sometimes free in the case of samples) or already has sunk costs in inventory.

Buying Real Randomness

Darius Kazemi created Random Shopper, a bot with an Amazon account. It has a set spending limit, enforced with a gift card, but can buy absolutely random items off of Amazon and have them shipped to Kazemi. In an interview with BoingBoing, Kazemi explained that the bot’s purpose was “to see if somehow those purchases feel more or less meaningful than something he would have conscientiously chosen himself; a way, if you will, of exploring his attachment to that ‘crap.'”

He’s getting the full experience that many other companies emulate — no curation or pseudorandomness here. I admit that I’d be willing to buy a couple of gift cards for a bot like this, just to see what comes out. There’s an appeal to just pulling the lever and seeing what happens. It’s the same instinct that drives gambling, except that each of these options actually always results in a win, at least as far as getting something for the money.

Kazemi is getting exposed to music, videos and books he would never have encountered otherwise. There’s a definite value to the randomness he’s added to his life. The fact that the bot has the constant ability to surprise him may not work for everyone, though: most consumers like a little constraint on the subscriptions and other random products that they purchase. But for people who are able to move outside of those constraints, Kazemi’s bot may prove incredibly attractive.

The Benefit of Surprise

I don’t have any statistics to prove that people who regularly face unexpected situations generally do better in life, but anecdotally, it’s true. Such people are more likely to explore new ideas on their own, adapt more effectively to different situations and be able to handle new concepts. There’s an upper limit to just how many shocks a system can take, of course, but the ability to cope is something that can be exercised and improved.

Since unexpected situations in general can improve our abilities to deal with problems, there’s a clear benefit to adding some randomness to our lives, preferably with as few constraints as we feel comfortable with. It’s probably not possible to add enough randomness to a day with a subscription to a monthly delivery of ink samples, but it may be a step in the right direction. Those ink samples, after all, can get you out of the comfort zone of using the same ink, day after day.

Consider how you can cultivate surprises in your own life, as well as in others. You may find a new business model of your own, once you take a walk on the random side.

Image by Flickr user Daniel Dionne

TextExpander: A Useful Tool for Writers


There’s a benefit to finding a niche, especially as a writer: you can make sure that you know the topics you work with inside and out. You know exactly where to look when you need a particular piece of data for a project. You can be an expert, to the point where people beyond your mother look for the work you’ve put out.

But you’ll also wind up typing the same things over and over and over again.

It’s a small price to pay: you can be truly adept with your vocabulary, provided you’re prepared to get as familiar with it as that one pair of pants that you can’t wear out in public, but that you will never throw away.

Taking Advantage of Over-Familiarity

But if you’re going to get that personal with your jargon, why not take advantage of the fact? Why not use that reality to speed up the time it takes you to do your work?

What if you could type a shortcut on your keyboard that would put those terms on the page with three keystrokes instead of ten? Over the next couple of years, that could add up to some real time. I do exactly that with TextExpander, a shortcut management tool available for the Mac.

Since I write about business quite a bit, typing ‘ap;’ spits out ‘accounts payable’ into my documents. That doesn’t seem like a big difference, but after you get used to typing something a little different, it can make more repetitive work go a lot faster.

I’ve got shortcut for all sorts of things:

  • the names and websites of the clients I work with regularly
  • templates for certain projects I work on (for instance, I have a weekly column that has to follow a very specific format)
  • the bio that I drop in at the end of articles I’m writing for certain publications

But there are some very cool ways to take shortcuts a step further, particularly if you spend most of your day putting words in a row.

Using Shortcuts to Improve Your Writing

If you write constantly, you’ll start to notice that there are certain phrases or even individual words that you use too much. Most of us are aware of such problem phrases, but it’s tough to write and find those phrases at the same time. You might pull a couple out during the editing process, but then again, you might miss them.

Every time I type certain phrases that I’ve decided I need to eliminate from my writing, TextExpander drops in an expansion that I can’t help but notice when I edit and that usually will catch my attention as I’m writing in the first go around. It usually looks something like ‘////////////BAD PHRASE/////////////’ — which is pretty hard to miss. I haven’t been able to entirely train myself out of using such phrases, but I’ve been able to improve the end product quite a bit.

There are also some words that I can’t write correctly for the life of me. I have certain suspicions about the way ‘soldier’ really ought to be spelled: I’m pretty sure there is a conspiracy around any word where vowels hang out next to each other. Rather than spend a lot of time stressing about conspiracy theories, though, I’ve created shortcuts to automatically correct my most egregious errors.

There are plenty of other ways to take advantage of shortcuts as a writer. I know I’m still only scratching the surface of how I can make my own workflow more productive, but I’m certainly going to keep experimenting with TextExpander and other tools.

A Little Bit of Markdown Makes a World of Difference

Over the past few months, I’ve made the switch to writing just about everything in Markdown. It’s a bit like writing in HTML — but much easier! I’ve reached a point that it would be hard for anyone to convince me to go back to my previous approach. I’m becoming a bit of an evangelist to convince other writers to start using Markdown, along with a few associated tools, to make workflow management much easier.

My Previous Approach

Prior to switching to Markdown, I wrote out blog posts (along with most other text) in a bastardized version of HTML. The goal was to be able to copy and paste what I wrote as plain text, without having to go through and change styling on specific words after I loaded a post into WordPress, or wherever else it was going.

You’ve probably seen horribly wrong results from cutting and pasting styled text from something like Microsoft Word into WordPress — if you haven’t, I strongly suggest against relying on this approach if you routinely write for the web. But, at the same time, writing in a text field on a browser just seems like begging to lose hours worth of work. Many sites now have some level of auto-saving built in, but it’s not something you can count on.

All of this added up to my adding in certain HTML tags directly as I wrote. But doing that can be a little distracting. Trying to figure out what a headline should say, as well as remembering which tag will result in the style you want can be a hassle.

Markdown to the Rescue

HTML is what’s known as a ‘markup’ language. So is Markdown, albeit greatly simplified. It’s easy to remember — asterisks do a lot of heavy lifting, as do octothorpes (also known as pound signs). It’s almost like adding a few little symbols to remind yourself to go back and add formatting latter. Luckily, though, with the right tools, the formatting winds up adding itself.

For me, those tools include the following:

  • Marked: This little app makes everything else possible. I write in Markdown in a variety of different programs, but I always have Marked running. It lets me generate live previews of what my text actually looks like from different types of files, as well as copying my work as HTML, so that I can drop it into a blog editor — or exporting the file as HTML, RTF or PDF.
  • Sublime Text: If you’re writing in Markdown, you’re going to want to write in some sort of text editor. I’ve been learning to code, so I just use the same text editor for everything. As an added bonus, there are some plugins for Sublime Text that make it into a great word processor. However, I only use Sublime Text for shorter peices of work — for longer pieces, it can get unwieldy.
  • Scrivener: For longer projects, I’ve started using Scrivener — not only is it Markdown friendly, but it has a ton of features for making big writing projects very easy to deal with.

That’s about $120 worth of software that makes my writing life much easier than it has been in the past. But you don’t need any of it to get started. You can rely on just about any text editor you may already have and try out some free tools for whatever platforms you’re working on; many content management systems have plugins that let them handle Markdown natively. Give it a whirl. I promise, you’ll be surprised.

Complicated Books Require Complicated Reviews

Freelancers Bible cover

I generally prefer to only post reviews of books and other resources that I’m completely enthusiastic about. I don’t want to waste your time or mine on something that isn’t worth the effort; at the very least, I don’t want to have to read a crappy book all the way through, just for the sake of writing a review. But this post will cover a book I’m not one hundred percent sold on, because there are some important questions this book has forced me to ask. For the record, I did receive a free review copy of The Freelancer’s Bible, though I’m pretty sure this isn’t the review they were hoping for.

The Good, The Bad and the So-So

Clearly, I’m wishy-washy on The Freelancer’s Bible: on the one hand, it’s an exhaustive reference manual for freelancers, particularly those just starting out. If you’re in that category, you need a book that tells you what you don’t know you don’t know. The Freelancer’s Bible covers everything it can about freelancing, even to the point of growing a freelance business into an agency or a product company — information that’s probably a bit beyond the target audience.

But the authors, Sara Horowitz and Toni Sciarra Poynter, put freelancing into a very particular context. Horowitz is the founder of the Freelancers’ Union. The name and projects of that organization appear very frequently within The Freelancer’s Bible, to the point that I started getting very frustrated as I read. The book implies that every freelancer should be a member of the Freelancers’ Union, which I see as a gross oversimplification. While I joined the Freelancers’ Union several years ago and have used their tools (though not their insurance or classes), my experience is that the organization is focused very heavily on New York City. Anything done outside of that city is something of an afterthought. There are other organizations in other places that may prove much more valuable to new freelancers.

The book comes off as a big ad for the Freelancers’ Union in spots, which detracts from its overall usefulness. I can understand why Horowitz would want to offer up the Freelancers’ Union as a resource — it is a good one, and Horowitz is rightfully proud of all the work she’s done. But it’s a bit too much.

Your Bias is Showing

We all have opinions that color our approaches to new projects — writers, doubly so. But a good writer is aware of her bias and makes sure it doesn’t get in the way of her message. The Freelancer’s Bible comes straight out of Horowitz’s experiences, however, and her own approaches may get in the way of helping new freelancers.

It’s not just a fault that appears in The Freelancer’s Bible, though. If you read a lot of books on freelancing, as I do, you’ll notice that almost all of these guides focus on writers — because writers are the ones putting them together. Horowitz’s passion is advocacy and that shines through, just as a love of writing shows up in most freelancing books.

This discussion (and I hope you’ll take the time to chime in on the comments) isn’t exactly a stunning book review, but it is an opportunity to discuss what we each bring to the table when writing a book about our passions and what we need to leave out.

Advertising is Seriously Broken

classified ad

Publishing online is a huge business. But it doesn’t work quite the way a lot of people seem to think it does. Whether you’re publishing software, content or something else entirely, you can’t just slap a bunch of ads in and expect to make your fortune.

It’s true that audience and attention are incredibly valuable online. But ad revenues have been on a downward trend for years (both online and off) — see this report from the Guardian. Online advertising revenues aren’t hurting nearly as badly, because there are still plenty of businesses still slowly moving into promoting themselves online. However, every company using advertising in any way is looking to cut costs and get as much bang for their buck as possible. It’s a tough business to get into.

The proposition is even worse when you consider that the grand majority of publishers online are small. The guy developing iOS apps and using ads so that he can release them for free isn’t able to spend a lot of time on optimizing his apps to earn money through advertising; it isn’t his skill set either. The same holds true for the girl publishing a niche blog. Building ad revenues is a very specialized talent and not everyone should expect to be able to do so.

Advertising Isn’t Good Money

There is no doubt that advertising has its place. There are people who do still make fortunes from slapping a whole bunch of Google AdSense spots on to their sites. But such people do a lot of research before hand, targeting specific high paying keywords and ensuring that they have enough traffic hitting their site and clicking on ads to be worthwhile. It’s not nearly impossible, but it does take plenty of work — perhaps more than most of the alternative ways you can make money from publishing.

Furthermore, there will always be companies interested in paying for advertising, provided you can connect them with a big enough audience to make it worthwhile. That’s particularly true because of how online advertising has revolutionized marketing. Fifty years ago, a business couldn’t really tell how effective a particular ad in a particular newspaper actually was. They could ask new customers if an ad had sparked a purchase, but customers forget or even occasionally lie. But with the advent of the web, a company could suddenly tell how many people had clicked on an ad and track their behaviour after doing so. Metrics have suddenly become a crucial part of marketing.

I have a personal love affair with metrics, but even I have some concerns about what they mean for the long term value of advertising. I look at things from the publisher’s side of things mostly, even though I have paid for advertising on occasion.

The rise of metrics have dropped the prices that publishers can demand for advertising. When advertisers can see exactly how many people see each ad and how many of those viewers convert into buyers, they can ask for better prices. That’s not necessarily a bad thing, but it does mean that anyone who has pushed up the prices they demand for advertising over the past century (hey, newspapers!) have to be able to justify those prices — and if they can’t, they need to find a different business model. Prices overall have dropped for ads and they will continue to do so as big companies invest resources in tweaking ads for the maximum possible return on each ad spend. There’s no use crying about it or trying to demand more money; it’s a fact of life for publishers.

At this point, the options on the table are to find a way to either play the advertising game, which starts with building huge audiences and ends with playing the metrics game yourself, or to find a different way to make money. Building your own products, charging for premium publication and pursuing other opportunities mean that any truly committed publisher will never starve. There are even options related to advertising, like affiliate marketing and sponsorship, that provide some opportunities if you think that your audience is the most valuable asset you have.

Advertising’s Cousins Have More Legs

While I wouldn’t want to depend on any one option related to advertising, such as sponsorship, to fully cover the expenses of any project I’m working on, there are some strategies that are related to advertising that are a little more stable — although the still require a great deal of work to reach anything resembling profitability.

Chief among these is sponsorship. You can draw a line between advertising and sponsorship because the relationship between the sponsor and your audience is usually very different. In both cases, someone wants to reach your audience. In the case of advertising, the strategy is usually to slap an ad up on the site somewhere that readers have to see it. The advertiser then hopes really hard that viewers will click on the ad. However, in the case of sponsorship, there’s a little more thought. If you’re doing it right, the publisher and the sponsor have a serious discussion about what content, activities or other connection will benefit and motivate the audience to take action.

A great sponsor may enable a publisher to make premium content available for free or to create some content she wouldn’t have been able to otherwise. Or a sponsor may come up with an entirely different approach to reaching an audience. But there has to be a benefit present for the audience. Consider this series of posts about Lanai on Plum Deluxe: it’s obviously noted as sponsored content (paid for by the Lanai Visitors Bureau), but the articles give real glimpses in to a visit taken to Lanai by the author. It’s personal and connects with the reader, showing what a vacation to Lanai is like without being a flat-out sales pitch the way that an ad would be.

There are plenty of other types of partnerships between publishers and organizations who want to reach the audiences those publishers have already connected with. They all are more expensive, both in time and money, for the company buying access, but they tend to have much better payoffs as well. Such approaches require skill on the part of the publisher, but it’s not such a specialized question as building ad revenues is.

To give credit where credit is due, thanks to Andy Hayes, the publisher of Plum Deluxe not only for providing me with a great example of sponsorship but also for helping me talk through my thoughts on the relationship between advertising and sponsorship. You can see our conversation on Storify.

Is Advertising Fixable?

I don’t see an easy solution for making advertising a more viable way to make money for publishers. There’s not really a need to invest in doing so, either: there are plenty of ways to make money as a publisher that don’t have as many potential pitfalls as advertising.

Consider exactly what you’re selling when you sell advertising on your website or app or whatever else you might be publishing. You’re selling access to your audience. It’s true that access is incredibly valuable, but you’re putting it in the hands of someone who may not know the people in your audience the way you do. They could alienate your audience in the time it takes to post a new ad if you aren’t closely engaged in the process.

Even if you do your best to make sure that you find advertisers and ads that fit closely with your audience’s beliefs and needs, you can damage your own connection to your audience by accepting advertising. It’s not out of the question that an audience member could come to the conclusion that you’re trying to sell them out, just based on your acceptance of advertising. Publishers have struggled with balancing the needs of their audiences and those of their advertisers for years. It’s never been easy, but audiences demand more and more transparency every day, making it harder to justify making money through advertising over alternatives like flat out selling whatever you’re publishing.

Image by Flickr user Annaliese Moyer

WordPress, the GPL and a Business Nightmare

I use WordPress on every site I own. I ask clients to use WordPress on their sites (and I tend to avoid even high-paying clients who don’t). I even speak at WordCamps — I’m the one yelling about content strategy to a room full of non-writers every few months.

But last week, I found myself looking at other content management systems, wondering how hard it will be to switch away from WordPress. That’s ‘will,’ not ‘would’ because I’ve committed myself to slowly migrating away from the platform unless something major changes. The issue isn’t so drastic that I’ll migrate every single site I own in the next month — the process may very well take years at the speed at which I move.

The Problem with GPL

WordPress was my introduction to open source on a practical level. I’d encountered Linux and some other open source software in high school and college, but I never used any open source software on a long-term basis or to the point that I needed to figure out what I could legally do with it before WordPress.

As it happens, what we can do with WordPress is a little more complicated than it might otherwise be. That’s due to the Gnu General Public License (more commonly known as the GPL). If you aren’t familiar with the GPL, consider it to be the equivalent of any agreement you have to click through to use a piece of software. The main difference is that, like all open source licenses, the GPL lays out the ability to pass a piece of software along, change it and otherwise interact with it without violating the creator’s copyright. Where the GPL differs from some other open source licenses is that it is categorized as a Copyleft license. I’m not going to go into depth on the differences between types of licenses, but I will include a short working definition.

When a developer modifies a piece of software that was originally licensed under the GPL and distributes it, the result (known as a derivative work) must also be released under the GPL. The same is true of ‘linking’ to GPL code, which is generally interpreted to include writing plugins for an existing piece of software. Stick a pin in that last part — we’ll be coming back to it.

WordPress is released under the GPL. The way that the WordPress Foundation interprets the GPL, plugins and themes for WordPress all automatically inherit the GPL, including pieces that aren’t actually code. For instance, if a specific photo is used as a background in a theme, it has to be released under the GPL with the rest of the theme.

You’ll notice that I keep using the word ‘interpret.’ That’s because there’s no case law for the GPL — it’s never been fully legally tested. Almost every case that has gone to court in the U.S. has been settled (the main exception is one of a series of lawsuits filed on behalf of BusyBox). Richard Stallman wrote the original version and let it loose on the world. Later iterations have been created with advice from legal experts. At the most basic level, though, the GPL is a cool idea dreamed up by a computer nerd. It will take a series of judges’ ruling to set how the license is interpreted in stone. In the meanwhile, some developers define ‘linking’ as including an API call while others limit it to using other code in such a way that it’s included in the code of the new program. There are similar differences in just how to define a ‘derivative work.’

This alone is problematic for anyone running a business based on WordPress, or any other software licensed under the GPL. In theory, any day now, a case could go to court about how to interpret the GPL and completely change everything. It’s difficult to predict end results of such a ruling: I could see a situation in which I might suddenly need to make software that I’ve customized for my business available to the entire world. Software that I use that might be improperly licensed could disappear or stop working overnight. I could even imagine a situation in which software under the GPL needed to be re-licensed under a new license. It’s not the end of the world, but no small business owner wants to suddenly be informed that she needs to change something about the platform she runs her business on.

Furthermore, the GPL spreads in a particularly viral manner. It is written so that it drags new software into an open source license kicking and screaming. Just about anything related to a project licensed under the GPL winds up with the same license, because you can’t connect a piece of software licensed under the GPL to one that isn’t. It’s not the worst open source license, in terms of turning everything it touches into open source, but it’s up there.

A lot of developers (both individuals and companies) try to get around the problem by choosing not to release their work. Google, for instance, relies on a ton of open source code that the company’s engineers have tweaked. But because the code itself is not distributed — you only get the search results from Google Search, not an actual piece of software — Google isn’t required to release its source code.

But for companies smaller than Google, things aren’t so simple. Consider a freelance developer who makes his living customizing themes for WordPress for his clients. The typical interpretation is that when that customized theme is swapped for money, it’s been publicly distributed — even though the freelancer only made one copy, for an individual client.

We’re getting too far down the rabbit hole of open source licenses here, but I want to impress on you that this is not just complicated: it’s completely open to interpretation. The standard practice is to follow the interpretation of whatever individual or organization manages a given open source project, which is where the problem with WordPress lies.

The WordPress Foundation’s Interpretation

The WordPress Foundation has gotten into some fairly public arguments with theme and plugin developers over how to appropriately license their work. The current conundrum focuses on developers who sell their work through ThemeForest. ThemeForest licenses all code for WordPress themes and plugins under the GPL automatically, but does not follow the interpretation that images, CSS files and other creative assets must also be licensed under the GPL. Let me be clear: this is a generally accepted interpretation that is considered legal under the GPL. However, the WordPress Foundation takes a differing (and also legal) interpretation of the GPL, requiring that those creative assets share the license of the theme or plugin as a whole. As a result, the WordPress Foundation considers anyone selling their work through ThemeForest to be violating the WordPress license.

As a result, the WordPress Foundation will not allow those developers and designers who sell their work on ThemeForest (or otherwise do not comply with the WordPress Foundation’s interpretation of the GPL) to speak at or sponsor WordCamps. If you’re not familiar with WordCamps, they are the conferences that take place in cities all over the world, providing a face-to-face forum for the WordPress community. I’ve been involved with several (volunteering, speaking, etc.) and consider them an important part of the WordPress learning process. Jake Caputo, who has also been involved with numerous WordCamps, wrote a post last week about being informed that his involvment was no longer welcome.

There are a number of major issues with how the entire situation has been handled.

  • First, and perhaps most importantly, excluding members of the community over an equally valid interpretation of a legal document has to be considered problematic. This is the sort of action that leads to major splits in an open source community, as well as makes users less willing to rely on a piece of software’s stability.
  • ThemeForest’s users are being punished for something that is out of their control. They don’t set the licensing policy. Matt Mullenweg (the guy who initially developed WordPress and founded the WordPress Foundation) has repeatedly suggested that developers and designers move to other marketplaces that comply with the WordPress Foundation’s interpretation of the GPL. But there isn’t another WordPress theme marketplace with a similar level of transactions. Plenty of people make full-time livings through ThemeForest, but I don’t know of any WordPress developer making a full-time income by offering their work through another marketplace. (There are several who do very well offering themes and plugins independently, but many developers in this category have had their own arguments with the WordPress Foundation over the GPL.) It’s nice to say that “forgo[ing] profits for principles” is the right move, as Mullenweg responded to Jake Caputo, but we’re talking about putting food on the table in an entirely legal way.
  • Communication between the WordPress Foundation and the owners of ThemeForest has been demonstrably poor. Collis Ta’eed, the founder of ThemeForest, has written up a description of how the company has attempted to balance the WordPress Foundation’s interpretation and a need to protect its sellers. He makes it clear that he’d felt that the two organizations had opened up lines of communication and were working to find a solution, when the WordPress Foundation chose to again enforce rules about noncompliant speakers.
  • The overlap between the WordPress Foundation and Automattic (also founded by Mullenweg and the owner of continues to be exceptionally blurry. During my time helping to organize a WordCamp, I saw firsthand that it’s not always clear who you’re talking to — whether they’re paid by the for-profit or the non-profit. That’s a dangerous way to run two very different organizations with two different goals. Whether or not it’s the case, that lack of distinction makes it seem like the WordPress Foundation has a problem with anyone making money from WordPress — except for Automattic.
  • The WordPress Foundation has failed to address the underlying reasons that ThemeForest uses a split license. On a fundamental level, it’s very difficult to distribute software under the GPL and still charge for it, because, legally, anyone can do just about anything with it (including turning around and giving it to someone else free of charge). Yes, that’s the reality of doing business with WordPress, but the ThemeForest license offers a middle ground that has resulted in developers and designers who would have otherwise worked on non-WordPress projects. Offering a little leeway creates a far more vibrant community overall.
  • Lastly, this isn’t nearly the first time that the WordPress Foundation has found itself in this position. There’s a certain appearance that the organization is attacking underdog developers at this point. I hate to wish a court case on anyone, but it’s reached the point where I want to see the GPL go to court and receive a ruling, preferably several times over, so that there’s a set of case law based on legal judgments on the situation.

All of this adds up to a platform that I am less and less comfortable using in my business. I can’t recommend WordPress in good conscience to my clients right now, particularly because I usually add a suggestion to go to ThemeForest to pick up a design. I am reluctant to commit too many of my own resources to it because I don’t agree with the principles that are being promoted. I guess, in a way, that makes me willing to forego profit, just as Mullenweg suggests.

There are plenty of other content management systems out there. I’d rather do business with an organization that I know will be able to continue offering their product under the same rules a year from now, that goes out of its way to be easy to work with and that is willing to discuss problems in a rational way. I run my business with respect for the freelancers and other individuals I deal with; I want to be sure that the people I depend on to earn a living get treated right by everyone else, too.

A Personal Connection to Envato

Obviously, if I’m willing to write this long of an article about the arcane nature of open source software, I probably have a horse in the race. In fact, I have several. ThemeForest is owned by Envato, a company that I am proud to have worked with for several years. I’ve written for FreelanceSwitch for four years, as of next week, as well as for several other Envato-owned sites.

I haven’t bothered to ask the WordPress Foundation if taking Envato’s money disqualifies me from speaking at WordCamps. Since I don’t sell any themes or plugins through ThemeForest, I should technically be in the clear, even though I get payments from the same source as people who have been informed that they’re not welcome to speak.

But I’m choosing not to speak at such events for the near future. I haven’t decided if I’ll refrain from attending entirely, though I’m seriously considering it. My reasons for doing so come in two parts. First, there are some great people I’ve had the opportunity to work with who are effectively banned from WordCamps and I’d rather not be a part of a community that chooses to think in terms of excluding those individuals. Second, the only reason that I don’t sell anything on ThemeForest is because I don’t have anything to sell. I’m bad at development and while I’m working on getting better, I’m not focusing on learning PHP. ThemeForest is an incredibly useful marketplace for both developers and designers, though, and I would be proud to be a seller there if I ever get decent enough.

I still think WordPress is a good platform and I expect to watch it thrive in the future. It’s far too late to even consider a different license for WordPress and I wouldn’t expect the WordPress Foundation to attempt it. Unless there’s a change in how the license is enforced, however, I’m taking this situation as a sign that I need to at least consider moving on.

Image by Flickr user Michael Dorausch

The Inverted Pyramid Format is a Dinosaur

The inverted pyramid format is one recommended for journalists (as well as other types of writers), where the most important information comes right at the beginning of an article, perhaps even crammed entirely into the first paragraph. Important details come next, with general background information coming last.

It’s a format that was developed for newspapers, although the exact genesis of the inverted pyramid is unclear. The version I like best is that the format grew out of journalists sending in stories by telegraph or phoning them in: the important details had to be up front, in case the connection was cut. It makes for a romantic picture — a journalist reporting on the Mexican Revolution, perhaps, desperate to get as much as possible back to his editors before Pancho Villa cut the telegraph lines. But the reality may be much less favorable for writers. With all the important information at the front, a lazy editor could just start lopping off the end paragraph and keep going until the article could be wedged into the column inches available to it.

Whichever creation myth is true, it’s clear that the inverted pyramid format is a legacy of a different approach to publishing, which was dependent on communication methods that were incredibly finite and lossy. A print publication only had so many pages and a paragraph at the end could easily be cut out.

The Extended Rule of the Inverted Pyramid

If the inverted pyramid is so old-school, why is it still the format primarily taught in journalism classes? Why did I get subjected to it in numerous classes over two different degrees, including a creative non-fiction class?

Part of the problem is that it’s an easy format to teach. Writing is an inexact process, particularly when time comes to teach it to new writers. It’s so much easier to tell students to write to a specific format and grade them on how well they do with that approach than it is to let them run wild. But that’s turned the inverted pyramid into a hammer that new writers will use on anything that looks vaguely nail-like. There are still situations in which using the inverted pyramid makes sense, but they are far fewer than the number of articles it’s actually used in.

The reality of where articles are published today is far different than the late 19th century and early 20th century — the years when the inverted pyramid emerged. We publish to blogs, mobile apps and news sites, which have no page limitations. The only restrictions we face are those we choose to accept, like Twitter’s 140-character limit. If I want to write a 12,000-word article on whether cats actually like cheeseburgers, the only factor I should really consider is if anyone will want to read it (and since my theoretical opus has cats and cheeseburgers on the internet, the odds seem good). I can write an article of any length and publish it immediately. The basis for the inverted pyramid is entirely gone, leaving only a shaky metaphorical shape.

The Guilt of the Inverted Pyramid

Some people feel that the inverted pyramid is more than outdated; it’s dangerous to readership rates. The broad concern is that it’s a generally uninteresting format. The reader gets the whole package one paragraph in. It’s trained readers to be lazy and to assume that the end of the article isn’t worth the effort. Sure, the article may have a kicker at the end to revive interest, but how many readers really make it that far after reading articles in this format for years? Even in the hands of the best writers, it’s hard to create an interesting story in the inverted pyramid format. At the most basic level, the inverted pyramid guarantees a boring story.

But there are some suggestions that the danger goes deeper. As a writer, I can usually tell by the comments whether someone read an article all the way through. A lot of the time, few people actually make it to the end, preferring to read the first paragraph and skim the rest. In the past, the inverted pyramid format made that approach perfectly reasonable. Readers have been trained that this approach will get them through most reading material. It’s a bad habit to get into and it’s an even harder one to break, unless you see that you’re not getting all the information you need. Moving away from the inverted pyramid format won’t fix the problem, but it’s a step in the correct direction.

It creates an interesting problem for all those newspapers with paywalls as well: universally, they offer a few teasing lines of the articles that they want readers to pay for. But those first few lines, at least in an article written in the inverted pyramid format, contain the whole picture — for anyone who doesn’t want more than that, there’s no temptation to pay to read further. There’s no clear solution that that little issue, either.

The Alternatives to the Inverted Pyramid

There’s a concept in design called ‘skeuomorphism’ — it’s the act of adding characteristics of an old form or approach to a design that doesn’t necessarily need them. In technology, it’s made obvious by example: your smartphone may ring with the sound of an actual physical telephone ringer, despite not having one itself. In many ways, the inverted pyramid is the skeuomorph of the writing world. We’ve been trained to expect it, just like we’ve been trained to listen for phones ringing, but it’s a characteristic we’ve imposed on new channels of communication.

It’s time to look for some of the forms that these new channels point to. We’ve barely scratched the surface of concepts like hypertext and we have the ability to publish practically infinite lengths of text. These may not be universal opportunities, but why not play with them and see what develops?

Even if you aren’t working on writing anything that you can afford to take that far afield, there are still some strategies that you should employ other than the inverted pyramid. Writing for the web demands storytelling: when a reader can be gone as quickly as she can click ‘back’, putting everything in the first paragraph isn’t good for your page views or other metrics, let alone for getting the whole story across. A more traditional approach to storytelling (just tell what happened, in order) or an essay format (a hypothesis and then some proof) can work well online, at least in my experience. Both approaches do require the writer to make some effort to be interesting, but it’s easier to pull off than in an inverted pyramid-style article. But these formats are just starting points. It’s up to you to decide what works for a given topic.

The Place for the Inverted Pyramid Today

There is a home for the inverted pyramid today, despite my unwillingness to let it run rampant over all forms of writing. It’s perfect for reporting breaking news. When you need to get across the facts of a situation like a natural disaster headed your way, put all the important information in the first paragraph. No one wants to be forced to read several paragraphs in to tell if their particular town is in the path of a snowpocalypse.

For a situation in which there’s an urgency to get information across, the inverted pyramid makes sense. It should still be taught and used and generally be a part of the writing world — though we can limit its place in the educational process to one class on the form and use of the format.

But the inverted pyramid should no longer take precedence when deciding how to write an article. Rather, the question needs to be what the right format for each individual piece of writing: it may add some time to the writing process, but we’re likely to wind up with not only better writing, but a higher level of engagement with readers in the long run. If we’re willing to pour time into efforts like optimizing articles for search engines and to promoting them on social networks, why not put a little more time into crafting great work?

Image by Flickr user Stephen Carlile