"Strategic insight only comes from well-informed chaos..." - Michael Lopp, Being Geek
Keeping up with software development is difficult. Blog posts, forums, articles, conferences, user groups, Twitter -- there's so much to filter. But it's vital: I believe that to be a successful generalist software developer over a long span of time (10+ years) you have to be ready to reinvent yourself at any time. The trick is to recognize when you need to do that. And that requires knowing a little about a lot.
For me, podcasts are a great way to maintain loose context around a number of topics. There are many articles (even industries) out there telling you how to optimize every 10-minute chunk of your waking day. But you probably have extended periods where you're either doing something physical by rote (shoveling snow, washing dishes, chopping vegetables) or just passing time doing simple things (commuting, in line at the post office, grocery shopping).
Podcasts are excellent for those times. Your brain is pretty good at both doing this sort of task and maintaining a conversation at the same time, so there's nothing dramatic to learn or re-learn. The only habits you need to pick up are how to listen, and what to listen to. And I'm here to help you bootstrap those.
How I Listen: Filter After Filter
Caveat: my setup may not be for you. It's probably too fiddly for most. But I've evolved it over time to work for me.
Rather than listening to my subscriptions based on publication time (most recent first or oldest first), I'm much more likely to listen to blocks of a particular podcast for days at a time. Some days I may feel like general interviews, some days like history, and others I want to hear technical presentations.
For that reason I don't use a podcasting app. In my experience, they strive to make things easier for you by downloading podcasts in the background and queueing them up for you so you never have to think about it -- you just hit the 'next' button. But, as you'll see, I actually like thinking about it, filtering the podcasts I listen to on my desktop before getting them on my phone is part of the process of establishing context. Here's how that works.
Filter 1. I get notified of new episodes via old-school RSS, using NewsBlur.  I've accumulated (and discarded) subscriptions over years through podcasts themselves, peer suggestions, tweets, talks over beers, and who knows where else.
Filter 2. Notification for a new episode comes in. I skim the show notes and, if it's something interesting, the file gets downloaded to a 'Podcasts' folder on my laptop. I'll typically augment the filename based on the content, especially since most podcasts are terrible about generating meaningful filenames.  For example, I might change a Fresh Air episode from 'npr_259377169.mp3' to 'fresh_air_netflix_microgenres.mp3' so I have some idea later of what it's about. That episode will sit there until...
Filter 3. I move files from the 'Podcasts' folder to a separate (dated) one and sync it with my phone. Deciding when to do this is another fuzzy filter, triggered when:
- my on-phone supply dwindles, or
- I have the feeling that a few perishable podcasts have accumulated in that folder, or
- I just have an itch to listen to something I know I've recently downloaded, or even
- my continuous integration job has taken longer to finish than I expected and I want something to do for 90 seconds
Once on the phone, the episodes go into an automatic 'Last added' playlist in the default Play Music app. From there...
Filter 4. I'll move podcasts to a 'Weekly' playlist, which holds the list of things I'll listen to at any time. Again, when this happens is up for grabs. For some podcasts I'll move large groups of them over at once -- Back Story tends to be like this, I'll listen to a half-dozen episodes one after the other, then none for a couple months.
Many InfoQ presentations are like this as well -- I'll accumulate three or four about NoSQL databases, or cloud architectures, or deployment strategies, then listen to them all. This helps establish a deeper context than listening to them one-off.
All those filters may seem like a lot of work, but they're not. I've done them so many times I don't have to think about them. Now, onto content.
What I Listen To: Technology
Note: all the links here are to the websites of the podcast rather than the iTunes store since, for now, I'm an Android user. Most sites will have links to both the RSS feed (what I use) and the page in the iTunes store.
Interviews and presentations:
- InfoQ has a fantastic set of interviews and presentations about general software practices and specific technologies and their impacts on architecture. You can create a custom RSS feed of topics you're interested in so you're not flooded by notifications. And most presentations handle the transition to audio-only (no slides) better than you might think.Some standouts I have saved in an 'All Star' playlist:
- Embracing Uncertainty from Dan North, on how risk aversion and uncertainty interact with management and agile development
- Optimized for Change from Kellan Elliot-McCrea on specific practices and general guidelines for scaling both technology and teams at Etsy
- Acknowledging CAP at the Root from Eric Evans on how the CAP theorem can impact your domain model design
- A number of presentations from Stefan Tilkov on REST and design.
- Software Engineering Radio: This comes out every month or two, and a typical show is not so much a back-and-forth interview as an opportunity for the interviewee to speak for long periods of time. But going through the back catalog will be highly rewarding: Rich Hickey, Grady Booch, Jay Kreps, Eric Evans, and Dick Gabriel are just a few of the fantastic discussions.
- This Developer's Life: Inspired by This American Life (more below), Rob Conery and Scott Hanselman produce thoughtful interview/thought pieces on a particular topic. Sometimes the topic is directly technology related, other times around careers, and then there is an incredible episode like Cancer that defies categorization.
- Accidental Tech Podcast: John Siracusa (one of my favorites), Marco Arment and Casey Liss talk about technology -- much on Apple, but lots of other topics too. All three are software developers but come from different arenas so while their opinions often converge, the divergences and discussions around them are great.
- Back to Work: Merlin Mann (huge fan) ostensibly covers productivity and work-life issues. And while it doesn't focus explicitly on software development most of the topics are spot on. But it's also "The Merlin and Dan Show," like listening to a couple of your favorite people knock around for 90 minutes a week. Getting dropped into that as a newbie is disorienting, so you should check out the Back to Work Starter Pack to get into the flow.
- Herding Code: I listen to these a few times a year since they're more focused on the Windows ecosystem. They do an excellent job of annotating each episode with not only show notes but time-stamped descriptions of the discussion
- Ihnatko Almanac: Andy Ihnatko is an astute technology writer who's not afraid to challenge industry and his own assumptions. He also likes comic books, movies, talking about Boston, and is very funny.
- The Talk Show: John Gruber writes Daring Fireball and, while he focuses on Apple technology and strategy, he's got a sharp eye (and tongue) for other areas as well. He cycles among different guests, all of whom are excellent in different ways -- his recent talk with John Siracusa was like hearing an old married couple go back and forth over topics they'd discussed for years.
- Java Posse: Grandaddy of language podcasts. Most of their episodes these days are recordings of their yearly open spaces conference, and in some of them you can even hear from Summanoids who have attended.
What I Listen To: Everything Else
- The Flop House: Snarky movie talk.
- Fresh Air: If you want to learn how to do interviews or elicit thoughtful answers from people, listen to Terry Gross. Her ability to interview people from so many walks of life and careers is incredible.
- The Incomparable: Groups of geeks talk about books, movies, comics, TV shows, and even have nutty but amazing draft shows. So much fun.
- Roderick on the Line: Merlin Mann and musician/raconteur John Roderick have a weekly wide-ranging discussion about everything and nothing in particular.
- You Look Nice Today: Adam Lisagore, Merlin Mann (again!), and Scott Simpson riff hilariously for a half-hour or so. I think has ended for the second time, but will probably rise for a third.
History, news, policy, and popular economics:
- Backstory Radio: Three history professors, each with a focus on different periods of US History, discuss perspectives over time on a topic. Sometimes they'll be topical -- for example, the recent federal government shutdown inspired Splintered Parties on how political parties have changed over time.
- Decode DC: Andrea Seabrook got tired of traditional reporting and created a show to spend 20-30 minutes on a fairly focused topic -- such as how money distorts politics and unintended effects of paperwork reduction.
- Freakonomics: Authors of the book of the same name discuss a different topic from the behavioral economics point of view.
- Planet Money: Great NPR show focusing on news from an economics perspective. Recently they commissioned a t-shirt which spawned a whole series of shows on how it's sourced, made and shipped, putting a face on what we say when we talk about globalization and how it can work the way it does.
- Slate Political Gabfest: Weekly discussion of US politics, typically taking on three topics a week. The three participants have been doing it for a while and have a great banter while keeping things moving along.
- Strong Towns: In another life I worked in a planning department so I still enjoy hearing about planning issues. This group has a strong opinion on modern land use development practices and how they work against what most people consider to be planning goals.
- The Moth: Recordings of people telling stories before a live audience. Warning: some of them will make you cry.
- Radiolab: Similar to This American Life but with more focus on a single story that tends to have more of a science viewpoint. Incredible editing and sound, and it's actually worth listening to an episode to focus on how they do transitions, cuts, and effects.
- This American Life: Weekly topic broken down into one to five stories on it. Over nearly 20 years they've mastered this format. Good place to start: their favorites page.
Other Places to Look
If you're looking for sources of new material you might try:
- The Podcast Awards is a great jumping off point, listing nominations in 22 categories
- A couple of technology-focused networks are also great sources: 5by5 has three dozen, and TWIT does as well.
I'm interested to hear about your podcast listening workflows. Do you use some sort of speed up to plow through your podcasts more quickly? Does your podcast app do a better job of letting you customize your listening flow than I've given it credit for? Comment away!
 My replacement for the unfortunately discontinued Google Reader.
 Look at the download link at this Michael Lopp interview: 'episode19.mp3'? Seriously?