If you don't know Merlin Mann, you're in for a treat. In the most recent edition of his Bulk Bag Newsletter, Merlin ran down five of his favorite talks, all available in handy online video format. I have rearranged the videos in chronological order (Merlin put them in order of awesomeness), so you can get a better sense of Merlin's public progression from "tips and tricks guy" through "realizing the entire internet has somehow become a tips and tricks guy" to his current position of "heart-on-his-sleeve brilliant rambler."
Merlin is a polarizing figure in nerd circles -- people tend to love him or hate him, and I think a lot of people (probably on both sides) misunderstand him. He's best known for his Inbox Zero talk (which is widely misunderstood to be about having zero emails in your inbox), and the majority of his deep thinking is about the problems of creative work, though many who follow him are not themselves in creative careers. Merlin has a tendency to ramble and riff -- which you may find charming or infuriating, depending on whether you get the jokes and like the guy. One of his most compelling (and/or confusing) traits is an increasing tendency to make meaning out of meaningless words and jokes (like "blue-sky solutioneering"), occupying an existentially and linguistically awkward space in which it's up to the listener to determine what, if anything, a given statement means -- some jokes are jokes, some jokes are sincere statements. It's an exercise for the reader to discern the difference. I think this is great; your mileage may vary. Watching the videos below, you can see this clear progression: he starts with a fully prepared, "professional" talk that's light on digressions, but as time passes he wings it more and more, showing more emotion as he goes.
I think Merlin is the single most interesting Internet Person I've run across. He is incredibly vulnerable, and he shares that vulnerability in a way that demonstrates fortitude. He's also a terrific singer and guitarist, but you wouldn't know it. Check out these videos, and beware the sporadic f-bombs.
Inbox Zero, 2007
Creating a distinction between "checking your email" and "processing your email." In retrospect, this talk is Merlin at his most practical and systematic -- he's talking about managing a particular technology (email) with a particular system (Inbox Zero). If your inbox doesn't represent a pain point for you, this talk probably won't matter much for you. But if, like me, you get hundreds of emails a day and live in an indetermine "world of pain" when surveying that influx of crap, this is a way to deal with it.
Worst Website Ever - 'FlockdUp,' 2008
In this talk from SxSW 2008, Merlin shares his "worst website ever" concept: FlockedUp™. It is a beautiful six-minute riff of meaninglessness, using the terminology of bizdev BS. For example: "FlockdUp™ is really uniquely positioned at this juncture to suck all of the oxygen out of this vertical. [A full two minutes of corpdork pseudowords continue.]" Featuring FlockBux™: "Like Money, but Monetized.©"
Makebelieve Help, Old Butchers, and Figuring Out Who You Are (For Now), 2009
Slightly NSFW (for language) at the beginning, somewhat rambling, and super-honest. On internet-based lists: "Little nacho chips of information that are really addicting." In general, this is a discussion about self-help, "life hacks," what real help is, why "knowledge work" is hard and encourages a particular form of help/hack-consumption, and (wait for it) old butchers.
Time & Attention, 2010
I'll let Merlin explain:
One afternoon in New Jersey, I was anxious, and screwed, and under a lot of pressure. First, the gig started really late because of three different grave technical problems. But, I had to get up there and Do My Thing. Unfortunately, my slides wouldn’t work, the mood in the room fell somewhere between total death and roiling hostility, and, so, I had to wing it. For 90 minutes. Lotta winging here.
This is basically where Merlin talks about the underlying issues (time and attention) that were the underlayment for most or all of his previous work.
Scared Sh*tless, 2011
At Webstock last year, Merlin gave a highly emotional talk about being scared. Note that this came shortly before the apparent collapse of an Inbox Zero book deal that had been occupying him more than full-time for years. (While discussing Springsteen's Born to Run saga: "Why is this meaningful to me? Ask me in a few weeks." Ahem.) Also, that mic is really not fitting in his ear properly. I just want to warn you again, this is really emotional and might make you cry if you watch for long enough.
Check out the excellent podcast Back to Work.