Note – This entry from 2013 is the most personal of these lists. If you’re interested primarily in music history, this may be one to skip. But if you want to know more about me or if you are generally interested in one person’s life journey as expressed through music, read on.

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I have decided to begin a new Facebook song-a-day project. This one is going to be more personal than prior projects, because it is going to attempt to convey the story of my own life in song. It’s also going to be slightly longer than the one-month limit I’ve put on previous projects, because I am going to be posting one song per day for each full year of my life, ending on my birthday. That’s 39 years as of this November 20th. (I was originally going to do this for my 40th birthday, but I decided I didn’t want to be starting the project around the time of my wedding, so…39 it is.)

Each day starting on Sunday, October 13th, I will post a song and indicate the year that it represents. I will then talk a little about the song and its place in my history. I will do this for 39 days, ending on November 20th. Because my birthday is so late in the year, I will be starting with 1975, my 1st birthday, rather than 1974 when I was born. Each song will then represent the year that led up to that particular birthday. But as you may know, I like challenging myself with these projects, so I have added some rules and constraints:

1 – Each song must have been originally released in the year it represents. (Studio release – not live, not re-release.)

2 – Songs should be representative of their time period (although since this is my list, my interpretation of “time period” may differ from popular tastes).

3 – Each band or music source gets only one song on the entire list. No repeats.

4 – Each song must have personal meaning to me now, and ideally will also have had personal meaning at the time. Most importantly, there should be a story attached to it. Some stories may be lighter, some may be darker, but they will all have a story.

I thought very hard about these rules, because they will keep me from including some music that has had profound meaning for me and my family. Simon and Garfunkel, the Moody Blues, various gospel classics – these and others all predate me, yet have had an impact on my musical and personal growth. However, I think that I was able to come up with a list that still hints at these roots while focusing on my own timeline. Also, there are some notable gaps in the final list – bands (or other music sources) that were certainly very important to me at the time but did not have space for inclusion. I am not sure if I want to discuss those as they come up or afterwards, but I will mention them at some point.

Also, as you might guess, the first few years are going to be less of the “aware at the time” and more of the “looking back” variety, but don’t worry. That will change fairly quickly.

1975 – Bob Dylan, Shelter from the Storm

I think it’s appropriate to begin the story of a life with a reflection on the safety of infancy. But when I look back at the place where life and family begin, it is through the lens of the difficulties I have faced. This song, my favorite Dylan of all time, expresses that dichotomy perfectly. It is dedicated – as the beginning of a story should be – to my mother, Dottie Simon.

“Try imagining a place where it’s always safe and warm…”

1976 – Gordon Lightfoot, The Wreck of the Edmund Fitzgerald

Every story needs a setting. With very few exceptions, most of my years have been spent in the Great Lakes corridor. The north coast is my coast, and so I present it through its most famous folk song. The Edmund Fitzgerald sank shortly before my 1st birthday, and this song was written within the following year, so this story is as about as old as I am.

Other people might use a happier or more triumphant song as the theme of their homeland, but for me I think the melancholy is appropriate.

1977 – Bob Marley and the Wailers, One Love

(I went through a huge reggae phase in junior high, so I knew Marley had to be on here somewhere. Exodus is definitely the Wailers’ best album, so the choice of year was easy.)

My earliest retained memory is of lying down on the mats in the day care at Concordia Seminary in Ft Wayne during my dad’s first year there. I chose this song partially because it includes a line from the classic gospel number People Get Ready, which predates me and therefore could not otherwise be on this list. But it is a song I associate very strongly with my dad, Steven Simon, so I dedicate this one to him.

1978 – Kenny Rogers, The Gambler

This song really belongs on the “songs of my parents’ generation” list more than on my personal list, but it’s on here for a very important reason. Anyone who is as old as I am or a little older knows this song by heart. It was so pervasive that even a 3-year-old going on 4 heard it ALL THE TIME. So I present “The Gambler” as the first pop song that actually entered my young awareness. Ear worms have changed over the years, but I bet this one is still just as effective.

Also, at some point during the late 70s, almost every adult male I knew had that beard.

1979 – The Cure, Three Imaginary Boys

This is where we take a sharp left turn and explore a little bit of music history. Although it would be a few more years before I was aware of it, a musical movement called New Wave was being born in England. This movement rose out of the punk movement of the 70s but featured a more electronic and processed sound that would come to define much of the 80s. There were several branches of New Wave, one of which would later develop into the full-blown Goth movement. The Cure were one of the founding bands of that aspect of New Wave, and their music would end up influencing my tastes and views for decades.

I chose this song because it was this time or a little bit later that I began to experience what I as a teacher would now call “socialization.” During my earliest years I was protected from peers largely because all of my time was spent with family, particularly my brother and my cousins. It was only when I was forced into larger social situations that I noticed that I didn’t really connect with other kids. Their interests for the most part bored me, and I could not understand why they didn’t want to try things my way.

Almost immediately, I began to experience isolation. In small doses at first, and as I said, mostly protected from it through the presence of family. But that would change.

1980 – U2, The Electric Co.

The new decade begins. I start my schooling and immediately find it inadequate. My kindergarten teacher sends me off to the side and tells me I’m allowed to just read, and I descend further into my private world of imagination. PBS, the station that taught me how to read, launches 3-2-1 Contact to supplement their already existing educational lineup, which just happens to include a show I loved called the Electric Company.

Meanwhile, in Ireland, a young band made up of energetic but arguably middling-quality musicians begins to make the case for fame with the album “Boy,” which includes this song. Within two years, this band would consume my awareness. U2 defined the 80s for me, not only musically but politically. They awakened activism and global awareness in me from a very early age. I’m sure many people will be amused that I still remember the “presidential election” we held in kindergarten. Knowing what I know now about how kids “vote” in such things, I assume that most of the adults in my life were talking about how tired they were of Carter, because I voted for Reagan. Or perhaps, knowing me, they wanted Carter and I just wanted to be different. Both scenarios are likely.

Regardless, that would be the last time my political views leaned that way.

1981 – Rush, Red Barchetta

1981 brought a host of life-defining changes. Although I had moved to a new house before, this was the first time that I moved to an entirely new city, an act that would become a regular practice in the first half of my life. In that new city, I was faced with an even worse academic situation – not just negligent but actively suppressing. The solution ended up being that I would skip 1st grade and go directly to 2nd. While this solved some of the immediate need for intellectual challenge and felt at the time like a new lease on life, it would forever relegate me to being the youngest (and for a long time the smallest) person in my class. This along with repeated moves served to further separate and isolate me from society and build a continuing pattern of reinforcement for my introversion.

It was in the same year that I became directly and actively aware of music. Thanks to my older brother Bentley, I was introduced to an album you may have heard of called Moving Pictures. To some extent I liked it because he did, but I certainly saw the appeal immediately. My favorite song on the album, though, was not the one that is its most famous (that would be Tom Sawyer), but this one. I definitely liked the music, but something about the story grabbed me. It was in effect my first experience with dystopian science fiction. When I discovered Bradbury and Vonnegut in my teen years, they felt just right.

I enjoy this video because it reminds me that 1981 was also the year of the Atari 2600. My early experiences with that gaming console would certainly have a long-lasting effect on my tastes and interests as well.

1982 – The Clash, Rock the Casbah

Back to Ft Wayne for one more year. Things felt somewhat normal again, but it was destined to be temporary. My dad was finishing up his last year at the seminary, and soon we would move again.

I remember this year as a year of listening to the radio and largely misunderstanding the songs. I have a distinct memory of my cousin Justin taking Queen very literally and thinking that “biting the dust” meant actually picking up some dirt and chewing. Similarly, I really enjoyed the first punk song I ever heard because I only knew “the Casbah” as some romantic place that Pepe le Pew promised to take that cat. So rocking it seemed pretty funny. It would be a long time before I understood how much more interesting the truth (and this video) actually is.

1983 – The Police, Synchronicity II

A few days ago I mentioned New Wave. By 1983, that musical movement was starting to peak, and The Police’s “Synchronicity” album was a perfect standard-bearer. This video in particular shows the look and feel of the more rebellious side of New Wave. It is…very 80s.Meanwhile, my family followed my dad’s first call to a place called Brazil, Indiana. (Indiana’s callous disregard for international names has led to a number of hilarious anecdotes in my life, including an early confusion over why anyone back in the 40s would have needed to escape from Warsaw.) Brazil was so small and remote that we went to Terre Haute to do any kind of “big city” things. Look it up and you’ll see what I mean. It’s not even on the interstate.

In a rare occurrence for my life, I actually managed to be big fish in a small pond for a while. But this particular pond was SO small, I didn’t really have anyone to connect to. The only reason I was marginally popular was because I was very quick-witted, and my school’s chosen mode of social interaction was “crack fights” or insult contests. I don’t know if many people actually liked me, but I didn’t care because I was getting attention.

The idea that insults are a way to gain notoriety is not a good lesson to teach an introvert, especially one who already secretly considers himself superior.

And that brings us back to Synchronicity II: a story about a man going through the motions, hiding the darkness inside.

1984 – The Smiths, Please Please Please Let Me Get What I Want

In the winter of 84/85, we abandoned that backwater town and headed north. We drove through our first of many Upstate New York snowstorms to arrive in a town called Utica. (Still international-themed, but this one at least made SOME sense.) It says something about where we had been that we considered Utica a major cultural step up.

For my part, I tried a little too hard to fit in and immediately failed. Moving in the middle of 5th grade is guaranteed to be tough anyway, and the personality factors that had accumulated against me were just too much to overcome: small, young, awkward, unathletic, introverted, smart, and let’s not forget trained in negative social feedback. Although I was academically better off at my new school, and I did have one or two friends, it became very easy to withdraw into solitude. My viewpoint became very dark. At 10 years old, I got a jumpstart on teen angst.

Enter The Smiths. Many people probably think of this song as “the museum music” from Ferris Bueller (much the way they think of The English Beat’s “Rotating Heads” as the “running home, jumping on trampoline” music). But for me it was one of many Smiths songs that spoke to where I was at the time. Their music was the perfect blend of morose wallowing and pleading optimism, and I dove into that headfirst.

1986 – Big Country, I Walk the Hill

This is an appropriate time to pause and have another look at the setting. I would end up spending a total of five and a half years in Utica, longer than any single place I have lived outside of the Chicago area. Upstate New York is very beautiful but cold. I had been water-skiing for years by that time, but the season there was so short that we needed to find something else to do as well. Cross-country skiing was a good fit for me, and there was certainly plenty of time each year to do THAT. We had an acre and a half of yard, so I could actually do it right out of the house. I also spent a lot of time climbing and hanging out in the trees at the edge of our yard.

The area around Utica was filled with rolling hills, but it didn’t take much of a trip north to find much bigger hills. I had never lived anywhere that wasn’t flat, so this was quite the experience for me. I really enjoyed the variety of the terrain with all the hills and lakes, the quickly changing deciduous trees mixed in with the tall evergreens. Living in Upstate New York taught me to appreciate nature in ways I hadn’t yet learned.

1987 – R.E.M., It’s the End of the World As We Know It (And I Feel Fine)

Some of you are too young to remember the origins of the phrase “alternative music.” By the 90s, it had become a genre of its own, with record labels actually selling artists as having an “alternative” sound. But when it began in the 80s, “alternative” literally meant “alternative to popular” in much the same way that “indie” did in the 2000s. (Indie is on the way to becoming its own genre as well.) Alternative music was something you had to scrounge for, something you couldn’t hear on the major radio stations, something that your friends handed to you to check out, assuming they had good taste.

There were two major sources of alternative music in the 80s: college radio and MTV’s 120 Minutes. 120 minutes was more universal, but also tended to be more British. You may have noticed that even before this list crossed into the 80s there was not a lot of American music. College radio often supported up-and-coming young American bands (Dead Milkmen, Violent Femmes, Camper van Beethoven), but it was rare for any of these bands to make it big.

R.E.M. changed that. In many ways, R.E.M. changed the landscape of the music industry and paved the way for other bands that labels had been ignoring because they were neither British nor conventional rock. I would argue that in part it was “looking for the next R.E.M.” that helped labels notice the Seattle grunge scene. Later bands got discovered early in their careers, but R.E.M. had to fight for it. It wasn’t until well into their musical growth that they released an album that finally broke through. That album was “Document,” and this song is one of the anthems of my generation.

(On a side note, I also like this video because the kid in it reminds me of my brother Bentley, who even had that haircut at one point.)

1988 – Midnight Oil, Beds are Burning

In making this list, the mid-to-late 80s were full of tough choices – years where I really could have gone a couple different ways. (Howard Jones or INXS? Big Country or Simple Minds?) But 1988 was a lock from the beginning. I believe that Diesel and Dust is one of the best albums of all time, and this song and video exploded into my awareness and made themselves instantly prominent. My political awareness had been waning slightly as I settled more into personal issues, but Midnight Oil brought global concerns to the fore once again.

In 1988 I was settled into junior high (my school was 7th through 9th). Ending 8th grade and beginning 9th, I had a few decent friends that shared my musical tastes. I was playing saxophone and just on the cusp of playing it well. But I still didn’t really have a place among people. Even in the groups where I was welcomed (like the various bands), I felt like I was accepted as a group member but not appreciated as an individual. With the educational training I have now had, I realize this feeling is quite common at that age and that teachers have the power to support kids through that development.

It upsets me to realize in retrospect that my teachers in those years may have been fine academically but to a large extent failed me socially. But actually, that was a common theme throughout my K-12 experiences. I don’t know if teachers of that generation were less trained in social and psychological issues, or if they were taught to be hands-off, or if they just didn’t understand me in particular. Whatever it was, I can look back and see many examples throughout my schooling that I would’ve handled differently if I were the teacher. I try in my own teaching to bring that understanding, to help support my kids in ways that I wasn’t.

1989 – James, Sit Down

The transition to high school (beginning of 10th grade for me) allowed me to leave behind some of the mistakes of junior high (of which there were many, and I only got to leave some of them behind). I continued to put energy into the various bands, and there were a few good people that I got to know that way, but I also made my first foray into theatre, which helped solidify friendships with a set of folks that I hadn’t really met before. And suddenly I felt like I had really found my people. They were nerdy, they were political, they liked the same music!

That group of friends was at least partially responsible for initiating my shift from music and math concentrations to writing and theatre. They were activists, and even released an underground newspaper called the Funky Armadillo Pilgrimage (for reasons I won’t go into at the moment). They hated the jocks and cool kids as much as I did, so together we created “alternative dances,” which were our own gatherings where we played the music we wanted to dance to. And yes, we played D&D and Axis and Allies. But mostly, it really felt like they understood me. I had finally made it. And so I dedicate this song to all of the good friends I had in my last year in Upstate New York.

James, by the way, was one of the last of the original Manchester bands – a group which included The Smiths and New Order – but they also bridged the gap into the “Madchester” scene of the late 80s/early 90s. James and New Order were among the few of the old-guard Manchester sound to continue past 1990.

“Those who feel the breadth of sadness, sit down next to me. Those who find they’re touched by madness, sit down next to me. Those who find themselves ridiculous, sit down next to me.”

1990 – The Sundays, Here’s Where the Story Ends

And so we come to one of the worst years of my life. The first half of the year I tend to roll into 1989, as it was a continuation of all the things I described yesterday. But then on June 1st the world changed forever. My brother Bentley – my guide, my protector, my moral anchor – died in a hiking accident in New Hampshire.

Bentley was one of the best people I’ve ever known. His compassion even at a young age touched lives everywhere he went. After his death, people told me stories of the amazing things he had done for them. He was very different from me.

After he died, I was sort of shocked awake to who I had become. I realized that I had been channeling all of my anger and bitterness back at the world that had hurt me, and all that did was create a negative feedback loop. I didn’t know how at the time, but I began to change. I began to finally learn from the example Bentley had been setting throughout the tragically short time he was with us.

My friends helped support me through the first couple of months of grief. I believe I was actually at Mike Heffron’s house when I saw this video for the first time. But then by the end of the summer we were moving again. We had to; there were too many memories. So for the rest of the year I re-isolated and withdrew into myself. I had a lot to think about.

This song for me becomes self-descriptive: “It’s that little souvenir of a terrible year…” You may notice that it is also the first band with a female vocalist on this list. At the time there was one other in my collection, and you’ll see that one soon, but it is true that the shift into the 90s also marked a shift towards female singers for me. Not completely, of course, but definitely a lot more than male singers.

Bentley Simon: 1970 – 1990

1991 – BoDeans, Good Things

I had a bit of a shaky start after the move, but then we switched school districts and I ended up in a fairly large school in the western suburbs of Chicago. The size of Lyons Township allowed me to ignore a large portion of the school population and find the small percentage (but still sizable in number) of folks with shared interests. I soon had a decent array of close friends and even started a band called Mockingbird Underground (for reasons I won’t go into at the moment).

However, despite my apparent improvement in social skills, I was still a bit stunted from my heavy introversion, years of isolation and bitterness, and recent upheavals. This meant that I was particularly behind in one area fairly important to a teenager: romantic relationships. I made all the classic mistakes: mooning over girls that wouldn’t give me the time of day, being oblivious to those that would, and (when I managed to date) picking the wrong person for the wrong reasons. These trends would continue through college and at least a bit beyond, as I failed to gather enough experience to learn quickly. Shakespeare and John Hughes would both have found me too sappy for their tastes. “Unrealistic,” they would have said.

I present this song as a musical illustration of that intense sappiness. To get the full experience, you need to know that when I sang this song alone in my bedroom, I replaced the word “over” with a certain girl’s name (one who did give me the time of day but that’s all). But I will say no more than that here. You’ll have to ask me in person sometime if you really want to know.

1992 – 10,000 Maniacs, These Are Days

High school ended with a pretty wide mix of very good and very bad experiences. Since one of the bad ones (prom) came very close to the end, I would say I was quite ready to move on. I had found people to connect with twice now, and I felt like maybe I was ready to do it again.

It turns out I didn’t need to worry about that at all. I had set myself up quite well to become part of a community that was more like me than not, and the connections began the very first day I arrived at Northwestern and went to my orientation. (Because apparently, similar majors + last name starts with S = instafriends.)

Even better than finding a community was finding a home. I chose to live in something that NU calls a “residential college,” which is basically a dorm full of people who have interests around a particular focus. Most of the friends that I made and kept were all part of that home: the Jones Fine and Performing Arts Residential College. So today’s song is dedicated to all of my fellow Jonesians, and there are quite a few of you here. (Not tagging everyone out of paranoid fear that I would forget just one.)

I mentioned a couple days ago that there had been one more female vocalist in my collection already by 1990. This was it. Sadly, this would be the last album the 10,000 Maniacs would ever do with Natalie Merchant before she went solo. I am very glad I got to see them on their last tour.

1993 – New Order, Regret

The title of this song will not be used to refer to some of my ill-fated attempts at romance in college. Nor will it refer to how I suddenly gave up on math (almost forever) when Calculus III seemed to require too much effort. Nor even my ridiculous mountain-man beard at the beginning of my sophomore year. It COULD refer to all of those things, but it won’t.

In the summer after my first year at Northwestern, my dad took a call to a church in Houston. For my entire life, I had looked forward to each major move as an opportunity to start over, to leave the bad things behind even if that meant leaving a few good things. But this time was different – this time I did not want to go at all.

Although I was beginning to develop a family at college, I still had friends from high school. Most of my best friends were a year behind me, so they were just celebrating graduation and preparing to pause for the summer and then move on. It would have been a great chance to spend time with all of them and make that transition, but that chance was taken away by the move. I ended up losing touch with just about all of them, including all of the members of my band, Mockingbird Underground.

Houston was not a good fit for me. I immediately discovered that I was not a hot-weather person. If I have to choose an extreme, I choose COLD, and Houston summers are about as miserable a thing as I can now imagine. But also it just did not feel like there was anything there that I enjoyed doing. And there was really no one who got me, and no real opportunities for meeting anyone more like me. Suddenly I was isolated again, and for the first time in my life I resented that.

I don’t blame my parents for this. I was beginning my independence, and they had to make choices that were most appropriate for them. It was right that I was no longer a major factor in the decision. But it affected me. I began to yearn for more complete control over my own fate.

1994 – Indigo Girls, Least Complicated

It took a surprisingly long time for me to get into the Indigo Girls. Part of this was the fact that Rites of Passage was the album that came out when they first entered my awareness. Even to this day, only about a third to a half of that album actually appeals to me. The other part was that the friends I knew who tried to introduce them to me were doing it the wrong way – they were being overly impressed by things that did not impress me. (“Isn’t this song a clever take on Romeo and Juliet?” “Sure. I’ll tell the Dire Straits you thought so.”) So for a variety of reasons, I was able to enjoy individual songs but never considered myself a fan.

The album that changed my mind was Swamp Ophelia. Here was an album that actually brought the musical and lyrical depth that other people kept touting. And even the lighter songs were ones that I could respect. I followed Swamp Ophelia with Nomads, Indians, and Saints, and THEN I became a fan.

College is about making mistakes on a grander scale. It is about facing more serious, sometimes even permanent consequences. For me in 1994, it was about the lesson that even my most well-intentioned actions can do harm to others, to my friends. And I know I’ve been forgiven for that, but it is something I reflect on to this day.

1995 – The Innocence Mission, Speak Our Minds

We go to college ostensibly to learn the skills we will need in the workforce. However, there are many life lessons to be had for those who are paying attention. I think the balance between “work training” and “life training” varies somewhat depending on your major, and I definitely had a major heavy on the “life training.” In particular, many of you who were theatre majors at Northwestern will agree that acting class really was life class.

My acting teacher was Mary Poole, and she kicked our butts physically, mentally, and emotionally every time we were in that space. I once wrote a short sketch for a writing class called “There is a Fire,” which began with this description of her:

There is a fire in Mary. It bursts from her head, and her white-blonde hair flares out in countless stray strands as if she were a scientist who plays too much with lightning. It shines in her eyes, and when they are turned towards us we find it hard not to flinch from the heat. It fuels her movements – her wild, full-bodied gestures that sometimes frighten and sometimes inspire. There is a fire in Mary, and she wants nothing more than to spread that fire to her students.

Today’s song is dedicated to Mary Poole, and to the several of you here who shared my experiences in her acting class. I think of her every time I listen to it.

1996 – Mazzy Star, Look on Down From the Bridge

My cousin Justin was born 36 hours before me. Growing up, we were as close as cousins could be. The last time I saw him, I could not have felt more distant. Paranoid schizophrenia had driven him so far away that I felt like he was lost behind his eyes, and I didn’t know what to do. The day I graduated from Northwestern was also the day that I found out he had gone off of his medication, wandered out into the night, and apparently laid down on a dark road where he was struck by a car.

Justin’s death was in many ways harder for me to handle even than Bentley’s. My brother’s death had been a clear accident, and though we felt robbed of his life we understood that there was nothing we could have done. With Justin I wondered for years if I should have paid more attention, should have given more time. I wondered if there was some way I could have helped but I was too wrapped up in my own minor problems to try.

It is still something I cope with. A few years ago I was able to write a poem about him, but I have yet to share it. It’s very raw and personal, and it hurts every time I read it. But it also hurts just a little less every time I read it, so I know I’m healing. I understand grief all too well.

Justin Blessing: 1974 – 1996

1997 – Sarah McLachlan, Sweet Surrender

I apologize in advance about this entry. One major goal with this project is to be brutally honest with myself, but I have to be very vague about 1997. Although none of you here were directly involved, some of you do know the folks who were.

Suffice to say, I made a number of mistakes, became very irresponsible about my life and my career, and generally made a huge mess of things. On the other hand, becoming irresponsible did mean that I spent a lot more time gaming, which is how I got to be friends with a number of you. So there is always a positive to take out of it.

But the overall takeaway from 1997 is that I was losing myself. I was directionless and unfocused. I didn’t know what to do, and I let myself fall into emotionally destructive situations again and again. It was this state of being that would lead me to make one very large mistake in the coming years…On a side note, I have had a number of occasions in my life where the band or singer I was listening to the most suddenly released some song right after a traumatic event in my life that was eerily similar. Dar Williams in particular has done that several times. In this case, it was the video. Being a huge Sarah McLachlan fan, I had bought the “Surfacing” album immediately and really enjoyed this song. Then I saw the video, and the first minute was a punch in the gut in how much it reminded me of what had just happened the previous year. (Please take that as a warning.)

1998 – Barenaked Ladies, Light Up My Room

Following a steady decline in attitude and ambition, I began to abandon my dreams. I found that I just couldn’t work steadily enough as a theatrical electrician to pay the bills, and my other part-time job just wasn’t cutting it. So I switched over to office work. Gaming continued to occupy a large part of my focus, and I met even more people that way. I consoled my artistic drive with guitar-playing in the apartment.

It is a decent illustration of how I interact with music to see what songs grab me from an album like Stunt. This is the album that brought the world “One Week,” a song that appeared in every teen comedy for the next several years. It also included “It’s All Been Done,” which would be used as the opening theme for the cartoon version of Baby Blues. The album was such a bro-happy pop album, and yet in the middle of it there is this gem. I really like when BNL goes introspective, and this makes for a good theme song for a lost and lonely 23-year-old who didn’t really have a plan for his life.

1999 – Tara MacLean, Jordan

Did I mention that I had also gotten engaged in 1998? Are you surprised? So were a lot of people. I had only been dating Jerusha for 6 months when we got engaged, largely due to her pressure. That should have been one of many warning signs to me, but as you have seen I was not in the best state of mind or life to be making these kinds of decisions. With everything that had happened over the previous years, I basically jumped at the chance to marry the first person who actually wanted to, no matter how much of myself I ended up compromising.

Other than shifting my career to contract IT work (almost but not quite completing the selling of my dreams), most of what happened to me in 1999 was wedding planning. We spent almost all of our time together getting ready for the wedding, which was planned for June of 2000. (More warning signs. In my life nothing good happens in June.) It should have been obvious to me that Jerusha was much more interested in getting married than she was in being married.

For today’s music selection, I offer a promising musician who also had her career interrupted soon after this. Tara MacLean was one of several Canadian acts that I got into largely because of the Sarah McLachlan and Nettwerk Records. I was lucky enough to see her live the following year, in a show actually opened by a coworker at one of my IT contracts who has now gone on to her own music career. This should be a nicely soothing interlude in the list.

2000 – Cirque du Soleil, Love Leaves Someone Behind

My wedding to Jerusha was a bit of a fiasco, not only in terms of ridiculous spectacle (ask any of my friends who were there), but also in terms of the chaos it left in its wake. Several relationship shakeups happened there, including the beginning of the end for someone else’s marriage. I only found out about these later, so I can’t be blamed for not taking them as immediate bad signs. But on the other hand the reason I was oblivious was because I was in Ireland on what can only loosely be designated a “honeymoon.” It was more like a backpacking trip with a friend, as that was about the amount of affection present.

Yet ever optimistic, I believed Jerusha when she said that what she really needed was a new start on more equal footing with our friends. She felt like all of our friends in Chicago were really MY friends, and she wanted to move somewhere that I wasn’t already established. So we headed off to Portland, Oregon. This would end up having two effects: first, it would heighten and accelerate the problems that were waiting to tear us apart, and it would remove me from any kind of support network that I might have had.

By this time, I was also getting heavily into Cirque du Soleil. We actually played a different song from this soundtrack at the wedding itself, but when I look back in reflection, this one seems the most accurate. In particular, one line seems very appropriate for describing Jerusha:

“Unconsciously people are drawn to things that feel strong.”

2001 – Lange (feat. The Morrighan), Follow Me

So for a while, we managed to distract ourselves with the newness of Portland. We spent our weekends at the Saturday Market, we tried out all of the Thai, Chinese, and Japanese foods (with especially fresh fish), we headed out to see all of the nearby nature, and so on. It was also during this time that I got heavily into anime. The seeds of my collection began in 2001.

Unfortunately, my favorite anime themes couldn’t make this list, because I discovered them well after they were released. So this song will have to be our stand-in. But that’s fine, because this song has its own anime-related story.

In 2002, I first went to SakuraCon, the Seattle-area anime convention. At the opening ceremonies, someone had made a very nice anime music video to this song. I was hooked immediately on both the song and the concept of AMVs. Within a few months I had made my own first video.

I also ended up staffing SakuraCon the following year. In my role as Gaming Manager, I oversaw a number of transformative changes that have stuck with the con to this day: we added go, we added a video/LAN arcade called “The Wired” that also played AMVs at all hours of the day and night, and we brought in the Penny Arcade guys. They won’t remember me because it was guest relations that actually made the contact, but it was my idea to invite them to their very first anime convention.

2002 – Peter Gabriel, More Than This

Jerusha and I spent over a year in couples counseling. It taught us to communicate, and through that communication I realized just how stilted and immature her views on love and relationships were. She could not give up the idea that love was a feeling that just happened, and if you stopped feeling it you didn’t love anymore. I tried to explain that love is an action that you choose, but she just couldn’t make that choice.

In September of 2002, we took an ill-fated trip to Philadelphia to see a bunch of my college friends and also to see Varekai (still one of my favorite Cirque shows ever). My friends really tried to be nice to her, but she just went out of her way to be pushy, selfish, and arrogant. Within a few weeks of our return, I let her have the decision of what would happen to us, and she chose separation.

I had already bought tickets to see Peter Gabriel up in Seattle in December, and we ended up parting as friends (largely because of the communication skills that counseling gave us), so we went together anyway. And here’s an illustration of Jerusha’s approach to life (and a story I haven’t actually told anyone before now because most of my friends already have enough reason to be annoyed with my ex):At the concert, she insisted that Peter had looked directly at her, and that they had somehow shared a “spiritual connection.” We were at the front of the upper decks, pretty much in the middle of the audience. I let her have her delusion, since we were already separated and there was no point in arguing. But that was the core of what she believed at that point in her life – that everything that happened was just for her, and that she had connections to things that other people did not. It was a very adolescent egotism.

For my part, I took this particular song to heart – not because it was “for me” in some stupid mystical sense, but because I really listened to it and took away my own message. I was losing everything I had, but I realized that what I had was not all there was. I could still go out and find more.

2003 – Dar Williams, The Beauty of the Rain

And so I prepared to leave Portland after just a few short years. I decided it was time to reacquire my dreams, so I aced the GRE and applied to the MS Ed program at Northwestern. I took a few months to finish up the divorce paperwork (even with an amicable divorce there’s still a lot to think about), and then I moved back to Chicago, and actually back in with my parents.

Before I leave Portland, I do have to say that I loved the rain there. It was exactly the right kind of rain to be out and about in, and I enjoyed walking around outside even though it rained a lot. So when my favorite folk singer, Dar Williams, came out early in 2003 with an album called The Beauty of the Rain, I thought “How perfect.” But then I heard the title track, and I realized the 2nd verse was about me:

And there’s nothing wrong, but there is something more
And sometimes you wonder what you love her for
She says you’ve known her deepest fears
Cause she’s shown you a box of stained-glass tears
It can’t be all, the truth about the rain
is how it falls, how it falls, how it falls

That was my relationship with Jerusha in a nutshell. She kept imagining that she was deep because she had pain in the past, but she didn’t understand how to move through the present. She refused to show vulnerability or admit weakness, both of which are essential to emotional growth. And I have often wondered why I loved her. Upon reflection, I take it not as a sign that she was worthy of it, but rather a sign of how unconditionally I am able to give it. It took me a few years to stop feeling like I had been a fool (although there’s still a bit of that) and start feeling that my dedication even through all of those trials was a sign of my strength.

2004 – They Might Be Giants, Experimental Film

It turned out that because of my narrow academic experience the first time around (theatre majors don’t have much in the way of external class requirements), I was missing a lot of core topics that I would need for my teacher certification. I had nine “deficiencies” that I needed to take care of, although I managed to cover two in one class. But those eight extra classes meant I would be in school a fair bit longer than the minimum 1-year plan. It also meant that I would be splitting my time between graduate and undergrad classes.

That was an eye-opening experience to say the least. I definitely learned that I had come along way as far as personal responsibility goes, especially when I think about how much those undergrads complained about pretty minimal work expectations. I believe that waiting 7 years to go back to school was probably right. If I had tried to do grad school right out of undergrad, I would have struggled through those extra classes, possibly even blowing them off like I used to do. As it was, I aced all of the classes during my MSEd program, both the deficiencies and the graduate classes.

It helped that I didn’t have much of a social life. I worked, studied, and that’s about it. I spent a fair bit of time on the internet, and was already a big fan of Homestarrunner when they came out with this collaboration with TMBG. This video was one of those great synergy moments where two things I liked got together. Like Lego and Star Wars. I use it here to represent my re-immersion into academia.

2005 – Over the Rhine, Lookin’ Forward

During grad school, I had entertained some idle hopes of stepping immediately into my own classroom. This turned out to be more difficult than I expected. I couldn’t apply for the jobs that were looking for more experienced teachers, and schools with openings for starting teachers were less inclined to hire folks with Masters degrees because of the higher pay requirements.

I ended up in an assistant position that did not initially start out well. At first they severely underutilized me, and I even had my supervisor (a reading specialist) tell me to my face that men could not be nurturing. Thankfully, after a few months they were able to swap me with one of the other TAs so I didn’t have to work with HER anymore. That’s how I ended up working with gifted pullout – grabbing kids out of their various classrooms for additional enrichment in math, writing, and social studies. This ended up being an important first step, but I was definitely itching for more.

I should mention that I did have an important relationship experience during grad school. (Not positive. Important.) I dated a woman with whom I thought I had a deep connection. I felt it, and she claimed that she did too. It felt like the times before when I thought I had fallen in love. But that was over in just a couple of months, and I was left reflecting that that “connection” had misled me somehow. It was that relationship that made me finally realize that I was the one who was doing that. The deep connection I kept feeling in my more intense relationships was just something I was bringing to them. And yes it affected the other person, but it wasn’t there because we somehow “got” each other on some spiritual level. It happened because I was so focused and aware, but NOT necessarily because she was.

This realization caused me to abandon many of my assumptions about relationships. I realized that the “connection” I had experienced could not be used as a sign that a relationship was going well, or even that it was a strong relationship. It just meant that I was in it. This clarified many of my past experiences, but also left me without direction for the future.

2006 – John Gorka, Unblindfold the Referee

It is incredibly disheartening to have to admit defeat in something very important. I had done it before – with my divorce – but at least there I had someone else I could hold responsible. In the summer of 2006, I had to admit defeat in my own personal endeavors, at least for a time.

A year as a TA is not unusual for new teachers, even those coming out of grad school. But as my job search dragged on and on I was faced with the prospect of a second year. I tried so hard that spring and summer, made so many inquiries and put in so many applications, but I could not even seem to snag an interview. I pushed it as hard as I could, but couldn’t come up with anything. And so by August I had to face the fact that I wasn’t going to get my own classroom and would have to try again the next year.

The situation felt a little bit similar to that of 9 years before. I felt somewhat lost and directionless, and I was even escaping into games again. (Less LARPing, though. More World of Warcraft.) But this time was different. I was more determined and even more hopeful. I knew that I WOULD succeed. I really believed it was just delayed. I even started working for the Center for Talent Development, which gave me a chance to have my own classroom in short bursts. I had a plan. I was still moving forward.

2007 – The New Pornographers, Mutiny, I Promise You

Finally in 2007 things picked up. Through a connection at the school where I was a TA, I managed to get a phone and in-person interview even without an application. That’s pretty typical, and it’s why it can be so difficult for the folks putting in applications. I went to interview at this private school for gifted children, and I happened to show up on the day when a middle-schooler was Head-for-a-Day. She asked me some amazing questions, and I was so impressed I immediately knew I wanted to work there.

I started working at Quest Academy that year and have taught there ever since. I have continued to work for CTD mostly during the summers but also sometimes on their Saturday sessions. At this point I can safely call my teaching career solidly established.

The joy and relief was palpable and continued well into the school year. It was in this spirit of optimism that I decided to take a chance and buy a CD based on a couple songs heard on NPR. The New Pornographers was an instant hit for me, and this song was one that I would play more than once when it came to that point in the album.

2008 – Dr. Horrible’s Sing-Along Blog, Freeze Ray

So, with everything else in place, it would seem to have been a good time to get my romantic life back in gear. So I got very heavily into online dating. (Well, heavily for me. I was nowhere near the frequency or intensity of some people.) I soon discovered that online is a great way to meet people…that you have much less in common with than you thought.

I approached meeting people online in what I think was a constructive way: looking for connections from which to build. With all of the information you’d get about someone up front, you would think this would be a very positive approach. But what I faced was a serious checklist attitude from most of the women I met. And I don’t mean a checklist like “You must have all these things.” It was more like the blood donation checklist – “Do you have any of these things? Because any one of them will disqualify you.” And of course with someone like me who has a huge list of interests, many of which are outside of the norm, it wasn’t hard to disqualify me.

I ended up going through phases over the next couple of years – a few months on and a few months off of online dating. I kept trying, but sometimes it just made me so tired and cynical.

Dr. Horrible was a great illustration of the dark side of my romantic experiences throughout my life up to this point. It’s kind of funny, because back in junior high kids used to call me “Doogie” to make fun of how smart I was. I didn’t really see it as an insult even then, and nowadays being compared to Neil Patrick Harris is all kinds of awesome. So there.

2009 – Living Colour, Behind the Sun

It is around this time that I spent a year and a bit living a sitcom. I was the wacky, chronically single, socially awkward upstairs neighbor to my best friends from college – a married couple which included the straight-man-who’s-actually-funny IT guy/musician and the wisecracking Jewish lawyer from New York.

It was a good reminder that getting older doesn’t stop people and life from being awesome. In fact, things were definitely on the way up. Sure, my online dating hijinks continued (including one woman who I think was trying to subtly proposition me for money), but overall it was good times. And in another reminder that some things may even improve with age, Living Colour released a new album that year.

If I were to choose a theme song for that sitcom, I’d probably go with LC’s cover of “Bless Those” by Little Annie. But that’s a cover so I can’t put it on this list. Instead I’ll just use this song to show off how amazing this band still is. I just saw them again a couple weeks ago and not only do they “still got it,” but they got it more than most.

2010 – Natalie Merchant, If No One Ever Marries Me

[Yes, I’ve already had 10,000 Maniacs on here, making Natalie the only double entry on this list (both band and solo). But she deserves it. In 2010, she released an amazing double-album called “Leave Your Sleep.” It is a bunch of poems she had selected and set to very different styles of music representing a broad range of American folk. The liner notes include the original poems as well as discussions about the poets themselves. At the time I said – and still believe – that it is accurate to say that the album is curated as much as it is written.]

After a few years of online dating, I was getting to the point where I felt like everyone I met just wanted to find someone that would be easy to choose. There was a distinct lack of the willingness to try and to put effort into relationships. They wanted it to just work. They wanted to do the work of meeting people but not the work of really getting to know someone to make an accurate assessment. Being an introvert, I was very much the opposite, and so I realized this was just not going to be for me. I hung up my online dating hat never to pick it up again.

I had just a few years to go before I would turn 40, so I decided that I would shift my focus and stop trying altogether to find someone. Instead, I figured that I would continue working on creating a life that I enjoyed. And maybe somewhere when I was in a good place for it I would see about adopting and raising a child by myself. (Thus the song selection.)

Things were going great otherwise. I was generally happy with my work and my free time, and I got to hang out with lots of great people. I even started playing a new Vampire LARP. And yes, at the LARP, there was this one girl who was very cute and interesting, but I was way too old for her. I mean, there was no way she could be interested in an older guy like me. That would just be silly.

2011 – Laura Marling, Sophia

It turned out that this girl who was named Jasmin (spoilers) was having thoughts that paralleled mine: “Oh no, I’m too young! He’d never be interested in a younger woman like me!” So after having danced around each other awkwardly for months, we fell fiercely into dating.

Our first year together was what I call the year of discovery. The first few months were filled with almost constant realizations of how in sync we were. Given my past obliviousness I really didn’t want to screw this up or be fooled by misleading signs. Occasionally I tried to step back and think about our relationship more objectively, but the evidence seemed to support the overall right feeling. I was torn between wanting to give us time to be sure and really feeling like I already was. I questioned myself constantly, and always came back with yes. I still do.

One thing I love about Jasmin is her depth. Although we definitely notice our 12 year difference in some areas of experience, she has insights into many things (including me) that I would not have thought of myself. And so to represent her, I offer Laura Marling – a musician of profound depth herself despite her very young age.

2012 – Carly Rae Jepsen w/ Jimmy Fallon & The Roots, Call Me Maybe

Note – Sorry that this one has to be just a link. The YouTube video has been taken down, and I can’t find an embeddable version anywhere.

https://fb.watch/aP7lYILix9/

On February 29, 2012, I proposed to Jasmin in the sandbox of the playground nearby. This was because of our long-running joke about how we really weren’t different ages – we were both 5. If you haven’t heard Jasmin explain the full story yet, you should ask her in person. The voices she does are essential to the effect.

Being engaged to Jasmin has been the most joyous experience of my life. I think of this video as a good visual representation of that joy. The Roots are absolutely the classiest band on TV.

Also, we took a trip that June to California (I had won the plane tickets in a raffle at Actors Gymnasium.) This song had just come out, and Jasmin had picked up the album because it was so ridiculously catchy. We blasted it out of the windows of our rental car as we drove up into the mountains out of the Sacramento valley, away from Mt. Shasta and towards the coast.

2013 – Vienna Teng, Level Up

And so we arrive at the present. It is from this place of security and comfort that I am able to push myself further – to stretch into new dreams, new risks, and new triumphs.

2013 is not the year that I became a writer. However, I have come to call it the year that I showed the world that I was a writer. With a play successfully produced and a book successfully published, I look forward to more projects and a new life path.

Today I turn 39. It has been a long and bumpy road to get to this point, but I hope that you can see how that road has shaped me and guided me to where I am now. I am happy and excited about the future, including of course my upcoming married life that will be much better than the first try. (Save-the-date announcement coming soon, but keep your eye on next fall.)

Thank you for your patience and kindness throughout this project. I know it has been sometimes sad, strange, or frustrating, but that is indeed my life. There are many things I would change about it if I could, but since I can’t do that I will simply accept and move on. Not just to live…to level up.