To say that discovering Merlin Mann’s podcast Back To Work was a revelation to me both undersells the value of what I got out of listening, and oversells the pedestal upon which I already put Merlin Mann’s online persona, in some ways an entirely separate subject.  True, it is through Merlin that I discovered John Siracusa’s work, and while I covered some of this story over there, this time I’m on an entirely other tangent, one about tangents, one about a shared past, and one about learning to believe in myself.  I think I share some embarrassing jokes about how poorly behaved I used to be, too, so you can at least tune in for those.

Like many people in America, I had a job that did not require any brainpower, took place in a cubical (and later, a “quad” with three other “teammates”), involved the use of dedication to “knowledge work” performed digitally on an out-of-date computer, all with the management allowance that we could listen to whatever we wanted while we did our work.  It was, in many ways, the only benefit the job offered, and as I quickly found myself caught up on every podcast I have ever cared about, I began to find large periods of the day filled with free time that I wanted to fill with something interesting, lest the horror of the drudgery of this job I hated would become too apparent.

I was, in fact, miserable at that job.  But this was nothing new.  I have hated most jobs, and I have never felt the kind of loyalty that most employers seem to be look for in staff that they want to pay a living wage to.  I have explored much of the shitty-job market that is available to people without a college degree: factory work, fast food, janitorial, musician, columnist, computer IT, production engineer, library staff, retail, teaching, farm hand, radio personality, aviary assistant, office detective, etc.  All of it felt like I was being punished for some past sin of which I was very guilty.  I couldn’t stand the rote dependence on arbitrary systems and middlemen to get something done that could be handled so much better in other ways, and I am still astonished at the pittance we receive for the lion’s share of work that keeps our world functional.

I had attended too many meetings, been a part of too many office chess games, have listened to far too many people have their personalities ground down to a nub, and found myself becoming a person I hated being every day when I would go to work.  I assumed – wrongly – that a degree would open doors that could take me to a new class of mediocre jobs, but I soon found that aside from a small bump in pay that barely covers the cost of living increases we’re constantly besieged by, even this six year odyssey toward academic enlightenment was only ever held against me as being too much or not enough to meet the requirements of the job I was looking into.  Most of the time, I spent all my off hours dreading going back, exploited every sick day I could on those mornings when I was about to cry at the thought of going in, and miserably scanned job listings as all of the same things came up again and again and again.

I have never done well with jobs.  And this ennui about my direction in life and my need to add new podcasts to help fill the void overlapped with the 5by5 Network that was always popping up on my phone as a “recommendation” based on the kinds of other shows I also enjoyed.  The name ticked some part of my brain that I enjoyed, and I felt like I had even heard a recommendation, or saw a link once?  Hard to say.  I added several shows, including Back To Work, described as a productivity and creativity talk show.  I (nominally) consider myself to be an artist – or, at least, an aspiring one – and felt maybe the trick to my own work was to start looking at it like work, so I could be more productive.  Having listened to enough NPR, I have surely overheard even stories about successful people who approach their creative lives in a very disciplined way, and my hope was that I could organize my creative work in a way so I could exert a little bit of effort to make it look like I was more productive that I really was.

Up until that point, I really looked at my creative life as a disorganized mess, with little regard to making it easily accessible or available were anyone to want to check it out.  I would make something, I would hand them out to people directly, talk about it a little bit on my blog (occasionally – when I remembered to do so), and then move on.  It was sort of the ephemeral nature of radio and ‘zines.  They are, ultimately, disposable and temporary in nature, fixed in time.  But if I was ever going to live the dream of making these creative works sustainable – somehow – I would need to start getting a little more serious about it.  If I just had some advice – some simple tricks I could use to be more productive – maybe my work would be better, because I was making more.

I fully anticipated listening to Back To Work as being a way to get some hands on, in-the-moment advice on how I can simply apply that one tid-bit and see it have a ripple effect through my creative work.  A sort of magic bullet, that once fired would see results that I could really use to my benefit.  I would listen with a pad of paper next to my desk at work, waiting for a chance to capture something amazing.

I was not at all prepared for what Back To Work actually was.

Admittedly, I did not exactly love it after the first episode.  I find this is common for media with which I become very interested.  I can’t even remember where I jumped in; probably with the then-current show, something from late 2013 or early 2014, maybe?  But in going back through the old episodes – largely in reverse order, humorously – I started to figure out the rhythm of the show, and really came to appreciate both the wit and wisdom of Dan Benjamin, but the wickedly funny Merlin Mann, who play off of each other very well.

Describing what Back To Work actually is sort of requires a brief overview of You Look Nice Today, a show that is so good that the rare and amazing moments when they do – randomly – post a show after having been dormant for over a year – you are pretty stoked to suddenly see a new episodes materialize out of nowhere.  In this show, Merlin, Scott Simpson and lonelysandwhich produce a fairly impressive satire of the kinds of douchy business and office conversations that we’ve all come to loathe.  The genius of the show is in the editing; each episode relies on the razor-sharp jokes that are made possible when you consider the digital nature or recorded Skype calls.  And it makes sense; the show was largely born out of their Twitter exchanges, where people would tracked this sort of thing had been entertained by all three of them piling on each other with 140 barbs that breathtaking in how note-perfect they ring in this age of “everyone’s a comedian.”

You Look Nice Today is a show that, even if largely dormant, works perfect as a document, and probably will for years to come.  It is a kind of comedy – like the work of Kasper Hauser – that will stand the test of time, but was born out of and is a part of The Inter-Web-A-Tron.  You Look Nice Today needs to live as a podcast; it doesn’t fly any other way.  I know that they do live performances, but the pacing of the editing, the Title Sequences by John Hodgman, the music that is used throughout, it is all of a piece that highlights and exploits the best of how a podcast works as a medium, and allows these three personalities to deliver not only the best joke for the show at hand, but the best meta-joke to complement it, and the joke about not having a joke, and another about how all of that wasn’t a joke, it was real, guys.  You Look Nice Today seems so much of the language of podcasts that there is a chicken or the egg quality to it, and certainly the way people produce new shows is influenced by some of the tone they set.

Part of this is owed to the way that Merlin Mann plays a very deadpan office meathead go toe to toe with anyone who wants to spew management bullshit-isms until nearly all meaning is drained from the sentence in the most hilarious way.  The character of Merlin Mann is that of a beleaguered office specialist, a person who has been hired to run a project he knows nothing about, and instead chooses to shuck and jive with tech world and office jargon that barely makes sense, even to those who know half the references.  And – like most tech-world hipsters who are always looking for the next trend to blog about – Merlin interlaces his nonsense with ’80’s and ’90’s indie-rock references, a boatload of Marvel Comics references, mangled malapropisms, 50 shades of “huh” that he punctuates his sentences with, and sprinkled with an incessant request for everyone to watch The Wire over and over and over again.  You Look Nice Today was a stomping ground for Merlin’s hipster’s hipster character to run while, delivering hilarious null-set constructions that perfectly reflecting the bullshit that tech world folks are all uncomfortably familiar with.

It is probably worth mentioning that I understand, intellectually, that this is a character Merlin is adept at playing.  Like John Cleese, Merlin has figured out a way to wear the discomfort of being and outsider in a world of intellectual one-ups-man-ship and let that character unfurl in a variety of ways, to create a comedy persona that – and I should emphasize this – is not Merlin Mann, the guy who goes home to his family at night.  Like Cleese, Merlin can play this character perfectly, from having lived and worked in that world, and having been a part of it since the very early days.  Merlin’s early web presence when the Inter-Web-A-Tron was still only the playground of a handful of nerds is well documented, and he – along with a handful of other early nerds – became the people that set the tone for the way media and the web would work together.  Merlin developed a personality that was informed by self-help and nerdy pursuits, but very clearly drew a line in the sand between his personal life and his “online” one.  For him, the web is his stage, and with each iteration of the outlet he chooses to use, he finds a way to make it uniquely his own.

To tell the story of Back To Work, I have to mention Dan Benjamin, founder of the 5by5 Podcast Network.  Dan is another one of those old-school tech-nerd guys, and after having tried his hand at office work, realized that his real passion was radio and video.  In 2009 he began the 5by5 Network, a place were the people who had been a part of the original web media landscape could develop podcasts that suited the kinds of geeky topics that listeners were looking for.  By 2009, the world of podcasts was still largely undeveloped.  You Look Nice was around very early, and there were some people getting involved, but networks were still something unheard of, and many people were looking to get discovered in podcasts so they could move on to something else.  Unlike Dan, they weren’t thinking about the long-term picture.

Dan began assembling a slew of personalities and shows that featured a number of people who were already a part of the tech media world in some form or another, and Dan even interviewed Merlin early on in an effort to get Merlin to join forces with him.  Merlin held off at first, as he was already quite busy with his own projects.  (Merlin performs seminars for businesses to help motivate staff and improve morale.)  But when a particularly lame presentation came to an end, he made a decision on the flight home to launch Back To Work, a new outlet for the more playful side of Merlin to find a home.  You Look Nice Today was on a hiatus, and the time seemed right.