Craig Cannon

I write Python and run hackathons at Cultivated Wit. Previously I made Joe Biden photoshops at The Onion. I post here and edit a blog called The Infrastructure Observatory, which recently crowdfunded its first publication, The Container Guide.
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2013 was fun. Here’s a big handful of things that started to make more sense over the past twelve months.

1. Living through an experience is the only way to understand it. 

My bad for undermining the entire post on the first point but I’m pretty sure this is a truth.

Before I moved to SF last January I thought it was 100% candy canes and gumdrops: tech everywhere and killer outdoors access. People told me there were downsides and though I understood the logic of their points I refused to really believe them. Turns out they were right. SF’s pretty good though.

2. Criticizing other people and their projects is a waste of time.

If something makes people happy, it’s great. Too often I find myself making fun of people that like to dress up as though they’re seasoned alpinists when in reality hiking to the Tourist Club (super rad, you should go) is the upper threshold of their experience. Total waste of time - your time and energy are both fixed resources - plus the aspiration towards becoming a serious outdoorsman in particular keeps stellar companies like Patagonia in business.

3. Figuring out what you really want is hard though essential to your own growth and happiness. Letting other people tell you what you want is easy and won’t encourage growth or happiness.

When I lived in NYC I didn’t feel this quite as much but in SF where nearly everyone works in tech I’ve found it dangerously easy to mistake industry-defined success with what I actually want, which is, as always, more burritos.

4. You need way fewer things than you think.

I’ve spent the past 18 months with only four shirts and two pairs of pants. Almost everything I need, outside of outdoors gear, fits into a 36L backpack. The experience has been way easier and more satisfying than I expected it to be. Over the past few months I’ve begun to accumulate more stuff and dress more like a grownup but I’m trying to maintain the spirit of simplicity.

5. An untethered life is both totally awesome and totally not awesome.

I left NYC in the summer of ’12, moved to VT, then SF, then Oakland, then back to SF because BART != NYC MTA. Each step was so full of excitement that it took me a while to realize how the lack of a constant home was taking a toll on my happiness. As with my minimalist streak, my plan is to maintain a lighter version of this lifestyle going forward.

6. Physical activities are mostly mental.

In August I hiked the John Muir Trail in eight days. My prior single day max distance was 18 miles yet I managed to do 27+ miles per day for eight consecutive days. Realizing how much control you have over an experience through believing in an outcome was empowering.

7. Commitment increases satisfaction. Constantly trying to optimize decreases satisfaction.

This includes everything from where you live to where you work to where you get coffee to what you order at the coffee shop. It’s easy to make a simple decision way too complicated and waffle endlessly while everyone else is busy actually doing things. My advice: take a friend’s recommendation and if it sucks, don’t be friends with them. Reverse optimization strategy wins.

8. Don’t wait for external factors to align before doing something.

I’m totally a sucker for this kind of thinking. “If X works out, then I’ll really go heads down on Y.” Dumb. Just commit and do the thing or don’t worry about it at all.

9. Speaking at conferences makes attending them way better.

Hilary Mason was the first person I heard say this and she was totally right. As a more introverted guy, I don’t particularly like conferences. I find “networking” anxiety-inducing, awkward, and not all that fruitful. However, when you give a talk the people come to you! Plus they know what you’re about so they’re usually much more relevant.

Thanks to Chris and Cameron for giving me the opportunity to present at Brooklyn Beta and Brady for letting me give an Ignite talk, twice.

10. Schedules are good for you.

Keeping a schedule - especially when working from home - is massively helpful in both maintaining sanity and increasing your satisfaction with your work. Instead of focusing endlessly on shipping code - usually with diminishing value - I’ll block out a three hour chunk and when the time elapses, I’m done. Afterwards I can point at the slot and say, “this is what I did” and hopefully feel good about it.

11. NYC and SF are both cool places. Please everyone, stop trying to pick a winner.

NYC has more diversity and culture. SF has more nerds and nature. There. Done.

12. Every list should always have twelve extremely important items.

Just like this one.

Happy 2014 everybody!

If you want to put creative stuff online you have a ton of options. If you want to consume creative stuff online you have even more options. But what if you want to be creative online? And what if you’re not technical? The list shrinks quickly. I’m hashing out ways to solve this problem and I made a discovery at this past Comedy Hack Day that I’d like to share.

I’ll pause for a second to mention that after the first CHD I realized how few sites there were that encouraged playfulness. I mean this in two ways: playfulness in how a user interacts with a tool and playfulness in why a user interacts with a tool. Either quality could exist on its own within an app but I’m suggesting that both benefit from the other’s presence such that the whole is greater than the sum of its parts.

Playfulness in how a user interacts is pretty straightforward: the app is fun to use. The app takes common design patterns and fiddles with them just enough so as a user you experience a neat interaction then stop and think, “oh, that was nice. I want to do that again.” If you focus all here you’re in game territory and games are awesome but I’m interested in play as a creative and constructive exercise and games don’t always accomplish that.

I think baking playfulness into why a user interacts with a tool moves you closer to that creative, constructive online environment. Industries all have their own word for this playful construction - riffing, remixing, forking - but it’s in large part the same concept: you find a thing you think is cool and try to make it better then throw it back into the ring. A commitment to encouraging those constant permutations around a thing feels like an essential component of any future creative platform. What I discovered through the most recent CHD was that there might also be reason to encourage a level of remixing and modification above individual items of content.

Going into the most recent CHD I made a commitment to help at least one of the teams turn their hack into a more lasting and hopefully useful product after the weekend concluded. I decided to work with Matt Klinman to help him expand his project, Clickstrbait—a site that generates clickbait headlines and traps users in endless loops of annoying UpWorthy-esque overlays. Here’s his hilarious demo. After the event we decided to make a Chrome extension that functioned like AdBlock for clickbait. We call it BaitBlock and you can find it here.

It’s pretty simple. After you install the extension, head on over to Twitter where you’ll see small buttons injected into each tweet’s div. You can use those buttons to flag any tweet as clickbait, which will block it from your feed. Once a tweet passes a certain number of blocks globally it will be blocked from the feeds of everyone with the extension installed.

While demoing it among friends and then at Brooklyn Beta last Friday, I was happy to see that people had fun using it and wanted more. Their first question was invariably, “where else can I block stuff?” They wanted to modify the interfaces of their favorite sites and leave it for their friends to see. The notion resembles an odd sort of digital graffiti/geocaching that, to me, looks and feels like play.

I’ve yet to come to any hard conclusions as to how—or if—a more versatile modification tool would be useful, but it seems like engineering a way for a non-technical person to mod the web could be fun.

If you want to chat more about this stuff, shoot me an email.

Special thanks go to Kevin Foley and Jon Ferrer for helping out with Clickstrbait and BaitBlock, respectively.

Like most projects I work on, Comedy Hack Day started as a joke.

At the time I was living in NYC with one foot in the comedy scene and one foot in the tech scene, working at The Onion and spending my nights and weekends at tech events. The more friends I made in tech, the more I realized they were strikingly similar to the ones I had in comedy. They were creative, nerdy*, and hilariously awkward. One day I was walking down Prince Street and thought, wouldn’t it be funny if you forced them to work together? A few beers later, Comedy Hack Day became a thing.

Also, the answer is “yes,” forcing comedians and developers to work together is super funny, both for the wonderful awkwardness—my actions included—and the final demos.

We held the first-ever Comedy Hack Day in NYC last September, a second in SF last April, and today I’m announcing the third, this time at the MIT Media Lab. The dates are September 21-22 and you can go here to sign up for the event mailing list and click a button that may or may not do something terrifying when you press it thirty times.

As someone who grew up in Boston**, I couldn’t be more excited to return home and throw the most awesome CHD ever at the coolest place in town. For those of you that don’t know what the Media Lab is or are unsure of what actually goes on in E14, the Media Lab is a graduate school at MIT that encourages faculty and staff to reinvent “how humans experience, and can be aided by, technology.”(1) In short, it’s an incredible place full of smart, creative makers. Also, drones.

Given that we’ll be at the Media Lab, this edition of CHD is going to be slightly different. For starters, we’re expecting way more hardware hacking as we’ll have a room full of talented Media Lab students, faculty, and community members. Second, like always we’ll have space available for local comedians and developers to participate, but because of limited capacity we’ll be offering up those slots on a first-come first-served basis. Sign up here to stay informed on when those slots will be open. Third, and most important of all, drones?

I’m super excited and can’t wait to see what’s built during this Comedy Hack Day. If you have any questions or think your company might like to sponsor the best event ever, you can email me.

See you in September!


*I’m using the term in the classic 1980s sense, not in the 2013, “Oh my god, we’re totally nerding out over Game of Thrones!” sense. Also, no you’re not. Everyone watches Game of Thrones. And everyone knows that the House Lannister official words are actually “Hear Me Roar!” and not “A Lannister always pays his debts,” but what’s more interesting is that when House Baratheon sieged… uh… never mind. Let’s get back to the announcement.

**Read: tiny town of 6,000 people 45 min north of Boston, but come on, it’s pretty much Boston.

1. Yup, a citation on the Internet. Who can spot the English major?

Every maker I know has a handful of side projects they’re thinking about building. More often than not, the projects don’t end up completed. Here’s a handful of the excuses I’ve heard and definitely used at times:

  1. It’s already been done.
  2. The market’s too small.
  3. It’s not solving a “real” problem, i.e. ending world hunger, reducing our dependance on fossil fuels, or making burrito delivery drones affordable for the masses.
  4. I don’t have a team.
  5. I don’t have the time.
  6. And the ultimate excuse, “Oh yeah, I’m not working on that anymore; I’m working on X instead.” This is the ultimate excuse because ditching old incomplete projects for new incomplete projects gives you the illusion of forward motion, but in reality you’re standing still, not building. 

Many of these excuses stem from the notion that the idea doesn’t feel exciting and innovative anymore. In my experience, the best ideas are the ones you work towards and not the initial concept. You’ll never know if it’s a really great idea until you build it. At The Onion, that took the form of riffing on jokes. In tech, it’s iterating on software and design. They’re really the same thing—creative construction towards a better product. But you have to start.

It’s important to remember that for the most part, side projects are just that, side projects. They’re for learning new skills, they’re for meeting new people, and they’re for fun. Assuming those notions, excuses 1-3 fall away. Excuse 6 is bs but there’s an easy fix, just build stuff. Once you start building projects, you quickly stop using that excuse. Excuses 4 and 5 work in tandem. You need a team to stay committed and find time. The best way to find that team is to share your project ideas. Too many people are too secretive about their ideas. Relax, nobody’s trying to clone your nonexistent side project with zero traction.


Here’s an example of how sharing ideas can help your projects get off the ground. This Saturday I was taking a 3D printing class at TechShop when I mentioned to a classmate one of the concepts I wanted to prototype—a bike light with a rider-facing LED panel that displays GPS and notifications from your phone. He paused and said, “You know there’s a team at the Makeathon working on almost exactly that, right?” I had no clue until then, and these guys were literally working one floor above us.

After the class I met Carter, the team lead, and we discovered that our concepts were in fact highly similar. I dropped my plans for the weekend, joined the team, and we ended up winning the hackathon - pretty awesome. What’s more awesome is that our prize was a commitment from IndieGogo to help us launch the product. So, in less than 48 hours we went from what was just another side project idea, to a real device that’s going to be made. Here’s our landing page with more info. 

In short, openly sharing your side project ideas is an excellent means of vetting concepts and finding a team to help build the prototype. And really, stealth startups are just lame.