This past weekend, I sat, and refreshed my Twitter feed as a whole host of people I admire from the Internet gathered in Portland for the XOXO Festival. Some were speaking, others just attending. They include: C. Spike Trotman, Virginia Roberts, Merlin Mann, Zoe Quinn, Myke Hurley, Anil Dash, Alex Blumberg, Dan Benjamin, and a bunch more. I’ve eyed XOXO longingly for the last couple years, but the buzz around this year’s was tremendous. Even despite #Gamergate nonsense trying to flood out the #xoxofest hashtag, Twitter was the best way to keep up from three hours ahead and a continent away. Lucy Bellwood’s livesketches, though I only saw them after the fact, were also incredible.

One of the things I find so compelling about XOXO, despite both never having been, and being unlikely to go (cross-country travel and accommodations are not cheap) is that it’s only nominally an “arts and technology conference”—the focus of the talks is on the human side of all of it. They’re chock full of personal stories, and that’s important. The talks from 2014 that stick out at me, from watching the videos are Anita Sarkeesian, Justin Hall, and Darius Kazemi. (So much Darius. I need to re-watch that.) Of 2015’s talks, Spike, Zoe Quinn, and Anil Dash’s are at the top of my list—in particular Zoe’s exploration of the nature of Internet Trolls—a topic she’s very, and unfortunately, well qualified to discuss.

Probably the closest I’ve come to an experience akin to XOXO is the recent, inaugural Facets Conference in Brooklyn this past year. I wrote my thoughts on the event back in May, and I swear by them. There is, all-too-often, a human story that gets lost in technology, and the tendency of technology people to focus on the object and the occasional, high-profile creator thereof. We get hagiographic biographies of rich CEOs, and lip-service to what their creations can enable us to do.

Every speaker at XOXO, and every speaker at Facets, used technology to make something. They picked up a megaphone, and used it to find a voice that would have, perhaps otherwise, not been heard. Wanting to be heard is an inherent human desire, after all. We write, we speak, we draw comics, we code, we make physical goods, and we want others to see them, touch them, maybe pay for them. Technology gives us the leverage to get our things in front of potentially millions of people with a lower, and lower cost of entry.

Every post, every podcast, every app, every piece of home-crafted jewelry is a lottery ticket for potential future success (Darius Kazemi again!). And success doesn’t necessarily mean striking it rich. One talk that looks interesting, at least from Lucy’s livesketch, is Bryce Roberts, who “wondered if another [VC] model was possible, helping to fund long-term, sustainable independent businesses without selling out.” After my own experiences with Venture Capital, this really speaks to me (as regular readers might know. Just flip through my writings on the business side of technology to see. This is a relevant one I’m proud of.

Perhaps one day, I’ll make it out to XOXO. Or, perhaps Facets will become the East Coast XOXO. (It’s certainly off to a killer start.) Even staring at it from afar, through a Twitter feed, and anxiously waiting for the videos to go up, I’m inspired to pick up my megaphone again, try to find my voice, play a lottery ticket, and get heard. It’ll take time, but as Veronica Belmont says, “Time means nothing on the Internet”. I know these people are all speaking my language: let’s make things and tell stories. We have the tools, let’s use them, instead of fetishizing the companies that make them.

A dear friend of mine is an public school art teacher with decades of experience on the job. She’s been bemoaning the push in public education towards what she describes as “left-brain” thinking—a focus on hard knowledge, facts, and skills over creative, “right-brain” thinking, the sort she excels at and teaches. [1] While much can be said about the miseries of the public education system in the United States, standardized testing, and its effects on students, that’s far out of my realm of knowledge. I think of my friend’s complaints in the terms of a technology essayist, and she’s on to something.

There’s a huge, aggressive, push to teach people to learn programming. It’s enough so that, even President Obama insists “Everybody’s got to learn how to code”. Never mind that that there’s jobs in technology that don’t require writing a single line of code. Programming is one of those skills that’s viewed as extremely “left-brain”: logical, linear, and direct. It often is. It’s also, often, something that requires huge amounts of creative thinking, problem solving, and “right-brain” style thinking. The best programmers are often ones who have wild, creative ideas and try to build them with the tools at hand—or making their own, new tools.

I’m not trying to write a polemic against learning to code. It’s a polemic that learning to code is not enough. Programming is a great way to empower people to create new, innovative things, stuff more innovative than writing the latest front-end to another miserable sharing economy service, built on around a pre-existing framework. Without education that teaches children both how to write code, and how to think creatively, they’re only getting half of the tools they need to make awesome things. Coding is a tool. The way you use it is what matters, and only with creative, “right-brain” thinking can you find new ways to apply it.

Far beyond just programming, being able to think creatively is essential to solving the problems that face humanity. The ability to create new ideas and implement them, is what has the greatest chance to save our species from itself. It’s hard to quantify the success of creative thinking, and harder to teach. The best tools we have to teach creativity and problem solving are things like art, music, and creative writing. [2] It’s a form of education that is hard, if not impossible to quantify, and that’s what makes it so easy to ignore, and to cut from our education budgets. Doing so is dangerous, and sells our futures short.

Matt Gemmell has stated the case for supporting, monetarily, the creators whose work we choose to follow.

The reality is that creative output involves cost – whether it’s at the professional end, with staff and materials and print runs or editing suites, or in the spare-bedroom office of the independent artist, where the cost is time, and what else might have been accomplished during it.

If we don’t support the things we love, with actual money, those things will go away. If we ignore the kickstarter campaigns, and block the ads, and read the content without supporting the author, and pirate the apps, sooner or later we’ll lose those things altogether.

So many of us in the technology space bemoan the rise of clickbait articles engineered for maximum virality on Facebook, top lists on App Stores of shitty, whale-chasing games loaded with In-App Purchases and ads, and then—in the same breath—gripe about the New York Times paywall and how noble print magazine brands are being shuttered because they can’t pay the bills. We groan every time we see “a change in a privacy policy, or a string of banner ads, or a new newsletter you never had the chance to opt out of.” These are all symptomatic of a greater cancer, and that is the rampant devaluing of creative work.

It’s not a new problem. People have been asked to work “for exposure” since time immemorial. What make things more problematic now is that awful mixture of too much “content,” too few ways to make it easy for people to pay for it, and the jury-rigged solution of maximizing ad views to make ends meet. It’s particularly galling in the face of “free culture” wonks that played a major role in defining the Internet we use, and still define a large portion of discourse in the tech sphere. They’ve done some good, of course—campaigning against Digital Rights Management, for example. But until we reach a Star Trek style post-scarcity economy, creative people will still need to eat.

The typical reply in these sorts of arguments is: “Hey! I gotta work a day job too. What make you so damn special?” I subscribe to the theory that an artist makes their best work when they can focus entirely upon it. A world of permanent part-time creatives, banging out everything from apps, to albums, to novels, to podcasts on nights and weekends is a recipe for a world of half-assed, sub-par creative work. Without the ability to make one’s craft their primary means of income, we all suffer for the loss. An artist or an artisan need not be “rich” but they need enough to make a comfortable living, to support themselves and, ideally, a family.

If any of this is going to change, it has to start with us, the people who read, listen, and use the amazing creative things that people make every day—from full-time, and part-time creators alike. There needs to be a real understanding of the value of creative work, and a rethinking of the relationship between artist and audience. I know my own relationship, as a music fan keen on cheap, easy piracy, changed when I made close friends who are professional musicians. I want them to succeed, make art, get paid, and use the money to make more art. It’s hard for any creative person to do much of any work when they’re scrambling to pay bills, put gas in the car to go to the next gig, or even put food on the table, so I go to their shows, buy their albums, and do my best to be a good fan.

And it would be disingenuous of myself to say I don’t have any skin in the game. I would love to make enough money from writing out my thoughts about technology and culture to pay the bills. Hell, I’d be happy if I was making enough per year to cover hosting and domain registration. [1] I can’t even afford a “spare-bedroom office.” I’m typing this up in the combination living room/dining room of my one-bedroom NYC outer-borough apartment. Sure, I have ways of getting paid for what i do, and i’m not shy about asking for someone to stick a buck or three in my tip jar. The tricky part is proving that what I do has value for a patron in a world where thousands, if not more, are giving it away for free. Including people are better than I will ever be.

I don’t want to come off as if I’m calling sour grapes. Even if I don’t make a dime more than I already have from writing, I’ll keep doing it in some form or another until I can no longer make the words come. The creative staff of Macworld and MacUser will land safely somewhere, and the non-creative staff—whose roles are just as valid—will probably find work of their own in time. They won’t all be Jason Snells, parlaying their status in the community into (what looks like) a successful solo career, but they’ll do fine. Even if he has to take a straight job somewhere, he’ll probably keep writing for himself too.

I do worry about the scaling of a patronage system. Maybe it works if your niche is just the right size to bring in your one thousand true fans, or whatever number times price of entry leads to making a living. Not everyone is going to want to take the solo route, and the more people you need to bring forth your vision, the more patrons you’ll need. I don’t think Dan Benjamin would ever be able to run 5by5 at the level he wants from Patreon donations alone. I would suspect Matt agrees. There’s no easy way to cut through the Gordian Knot of creators getting paid, especially independent ones. Patronage seems a good way to start.

A few weeks ago, I bemoaned the state of my personal data. While I’ve only made inroads on that front since then, thinking about my data problem, and how to solve it, gave me cause to look at my task management system, and the piles of crap and cruft that have built up within. Part of the problem I have with task management, along with notes and bookmarks, is my desire for a universal solution. I want something I can load in all my personal projects, my work projects, my day job projects, my writing… and I’d settled a while back on OmniFocus, the 800-pound Gorilla of Task Management.

OmniFocus is a fine piece of software, and well worth the price. However, it wasn’t working the way I needed. The problems I had with OmniFocus as a task management system were as follows:

1. My day job forces me to use Windows, so the only way to view my OmniFocus data at work is to either lug my iPad in, or use my iPhone. Neither of these are elegant, easy, or look great in front of the boss.
2. So much of my day job work is cranking out widgets. A task comes in (by email), and often needs to be done that day. if I’m not already working on something, I tackle it immediately. There are some projects that are longer in duration and scope, but not many. Either way, the pain in the butt of entering those tasks into OmniFocus, even with MailDrop, is too much.
3. OmniFocus is absolutely crap for creative tasks that don’t have well-defined “Next Actions.” Something like “Write blog post” is too vague, “Write 500 words” is too specific. It’s a pain in the butt, and no good for tracking my progress on many creative tasks.

Then, Nick Wynja turned me on to Trello. I’d used Trello (very) briefly while working for The Startup, and it didn’t click with me. Something about the UI, the multi-dimensional scrolling piles of lists, and the general visual chaos of the office Trello boards left me scrambling for another solution (OmniFocus, natch). With Nick’s praise, I decided to give it another try, and after a day or two of experimentation, I found Trello to be perfect for my day job, and pretty good for tracking my writing.

I use Trello like a simple Kanban board. At the day job, I keep one list of cards for Future tasks, and stuff I’m waiting on. I keep another for stuff I need to do today, and another list of whatever is done. When something comes in to my inbox that needs doing, I either create a new card, or just forward the email to Trello. At the end of each day, I archive the cards on the Done list, and add whatever upcoming stuff needs doing to the “Today” list so it’s ready when I get to my desk. For my writing, it’s even simpler: A list of idea cards, a list of works in progress, and a list of what’s done.

What Trello sucked at, at least for me, was letting me manage any other sort of task. This left OmniFocus for just tracking day-to-day todos, and that seemed… excessive. I played around, first with Reminders. When that proved too simplistic, I went back to Things, enticed by the Mac version’s gorgeous Yosemite update, and the iPhone version’s new UI as well. A week and a half of using Things reminded me exactly why I switched away: Things doesn’t work the way I work. I like the ability to view things by project, or by context, and Things just doesn’t have that. The path was clear.

Saturday, I launched OmniFocus, selected everything, and deleted it all. I grabbed my notebook and pen, pulled up the “Trigger List”, and scribbled away all the stuff I need and want to do. I came up with new contexts, and I set them up. I loaded all my tasks, projects, and (non-day job) professional obligations into OmniFocus, built them out, and now I’m starting with a clean slate. Whatever was important carried over, but that’s because it was still on my mind. The majority of stuff I thought I needed to do vanished into the digital ether, and if any of it should become important again, I’ll know about it.

There’s a lesson I’m opting to take away from this experience. It’s never a bad idea to audit yourself. Thinking about the tools I use, and how I use them, gave me insight into where I was falling down, and helped me put together something better suited for what I do and how I think. I’ve been trying to cram square pegs into round holes when it comes to just keeping track of what I need to do. It’s true, one should never focus on the tools over the work, but it was worth the disruption to figure out what works best for me. We’ll see if this sticks, of course.

I just watched this excellent talk by Darius Kazemi, from XOXO. If you have 20 minutes, I suggest you do the same.

Done?

Good.

Darius is on to something. When we hear successful people talk about what made them successful, our instinct is to follow their lead. The thing is, there’s no magic formula. It really is about luck. And the bigger the success we want to model our careers upon is, the more luck it takes.

Spike, a comic artist I’ve long followed, posted an excellent 24-hour comic for aspiring cartoonists called “This Is Everything I Know”. If I had to single out one page, it would be this one. Once you buy your lottery ticket, getting to that point is just luck. End of story. Why, then, do we keep sucking down someone else’s success stories, and trying to model our careers on them? And why does it hurt so damn much when success doesn’t come after putting in the work?

Part of the problem is survivorship bias. When all you see is the people who succeeded, talking about how they succeeded, and all you try are the things people did to succeed (in implementation, at least), and you don’t succeed—what then? When I worked for The Startup, I saw this sort of thinking play out on a monthly basis. Someone—usually the founder—would come up with a new feature that would drive user growth and revenue, and the technology side would rush to get it together. And, universally, these ideas were almost always something another, popular Internet Company in an adjacent space was already doing. They often didn’t get traction, and soon we were all distracted by the next shiny object. Looking back, this was the technology equivalent of buying scratch-off tickets.

For two years, my friends and I did a podcast that I was quite proud of. We pushed it to our friends, and we did our damnedest to make it great. In the end, we had double-digit download numbers, and eventually I sunsetted the whole darn thing when it was clear that the work of making it wasn’t worth what I was getting out of it. That was a lottery ticket, and it lost. Instead of trying to win the Podcast Lottery, I’m trying to take the money I spent on those tickets and am using it to buy more tickets in the Blogging Lottery. So far, it’s worked out better, and doing it is a lot more enjoyable.

Instead of success stories, I want to hear from people who failed, especially if they failed by doing the “right” thing. We have more to learn from those who lost the lottery than we do from those who won. I suppose, in the meantime, the self-aware stories from folks like Darius, and to a slightly lesser extent, folks like Justin Hall who succeeded by some measure, and then failed. That’s where the true lessons lie, not about success, but about life. One lesson I have learned, however, is to keep buying lottery tickets, and this is my latest one.