Ranking Every Year of Your Life

I was bored and started doing a dumb thing over on Twitter: ranking each year of my life based on how, as I sit here right now, I think they went for me in the grand scheme. How I feel about them, mostly on a visceral level. I just ranked them on Twitter, but I have time to kill and more space here so I’ll add some brief, oblique, and sometimes stream-of-consciousness commentary.

Note 1: I couldn’t rank all 46 years of my life together as my 40s and my teens, for example, are apples and oranges. So I grouped them by decades 2010s, then the aughts, the 90s, etc.

Note 2: The rankings are strictly personal and relate to what was going on in my life and how I felt about it. Some pop culture may bleed into it as that affected me, particularly when I was younger, but don’t read in any political crap, current events, news, or whatever into ’em. 2001 was pretty bitchin’ for me overall. That I have it ranked high does not mean I was a big fan of 9/11. Get me?

Note 3: In case you need to orient yourself here, I was born in 1973.



It didn’t matter. I was too young. For me it was mostly a big blur of Toughskins pants, my bedroom, very large Buicks, TV shows and movies with lots of car chases, the vaguest appreciation that times were tough economically speaking even if I didn’t know what that meant, memories of my elementary school and my preschool which seemed gigantic and full of cinderblock and flecked linoleum and whatever else you probably imagine the 1970s looked like.

As an adult who thinks a lot about the direction of our country and society, I look back on the 70s now as a great lost opportunity. A time when Jimmy Carter told us that, maybe, it’d be a good idea to turn the thermostat down a tad and maybe wear a sweater to save some money and, in response, our entire nation threw a 40-year-long-and-counting temper tantrum in which it decided, screw that, we’d rather first bankrupt and then destroy the planet rather than sacrifice a single thing. But like I said, this is a personal list, so let’s move on.


1985: Playing outside all day. Living in a neighborhood that felt like living in a city in the 1940s, where I could walk to shops and school and the library and everything. I think there was even a damn news stand. Obsessing on sports in a way I hadn’t come close to doing before. Basically the perfect year for a kid. Assuming you, like me, often wished you lived in the 1940s.

1989: Driver’s license, first job, first real girlfriend who I could, like, go pick up and go make out with and stuff. All the freedom all those things suggest. Life totally changed, as it tends to do, when you turn 16. I did, however, experience what I know now to have been my first real depressive episode that fall. I didn’t know what to make of it at the time. It’d take therapy when I was in my 40s to actually process it. I wish I had been aware of it then. It might’ve made it easier to deal with the ones that would come later.

1984: Decades are artificial constructs. You don’t have to count 0-10. Culturally, this is when it felt like the 70s actually ended and the 80s began. Maybe it was in 1983, but 1984 is definitely when my memories switch from black and white to color and everything seemed to leap into what was then a new, modern era for me.

1987: Started the 9th grade. Crushes on girls began to transform into something more serious. Not that I dated anyone. Maybe I was just a proto-emo kid. Definitely the year I began to listen to sad love songs and imagine that EVERY SINGLE ONE WAS ABOUT ME AND WHAT I WAS FEEEEEELING, MAN. Not gonna lie, though, that’s not the worst feeling when you’re wired like I am.

1988: MTV all day, every day. Learned to deal with the emo stuff better. Maybe because I discovered beer. Got in a monster car wreck but didn’t get a scratch and assumed that meant I was invincible. Moved to Beckley, West Virginia and hated the idea until I actually got there and then I loved it.

1986: Played football for several years surrounding this one, but this was the one I felt the most like, yeah, I might play football for a long time. Was wrong about wanting that. Was probably just thinking that because I was awkward-looking, getting fat and kind of hated myself and didn’t know what else a fat kid who was kind of good at football might do.

1980-83: Kind of a blur, not unlike the 70s. I remember the TV shows a bit more clearly, though.


1991: Started dating the girl I’d end up marrying and having kids with which, even if that didn’t last, was good for a long while. Graduated high school. Went away to college. Turned 18. I do adult pretty well and this is where it started.

1990: Dated multiple girls and passed a — er, um — personal milestone in the process, but let’s keep this clean. Smoked weed for the first time and, since it was pretty neat and I never developed a drug problem of any kind, I can look back at it as an unambiguously good thing that I’m glad I did. Got into a lot of punk and alternative music that set the course for my tastes in that regard for the rest of my life. Started DJ-ing at a top 40 radio station and got a bunch of leads in school plays, both of which caused me to became fairly popular which was quite a trick for a kid who, on paper, did not have any right to be popular. Damn, maybe this should be ahead of 1991?

1993: Shook off a bad fall of 1992 (see below), found myself in a very happy place, and hit my stride academically in college. Took all kinds of classes I loved and which helped form the person I am today, all while getting great grades. Stayed up on campus over the summer rather than go home and, as it would turn out, would never live at my parents’ home again. Got my first apartment.

1994: Just college. Less fun than 1993 because I actually had to start deciding what I wanted to do with my life when, actually, I just sorta wanted to stay in college forever. For that reason I thought hard about grad school but then I realized I’d have to pick something specific to study and since I’m a dilettante at heart that seemed like a drag. Started thinking about law school which also seemed like a drag but a faster, better-paying one in the long run. Broke my collarbone in a bike wreck that summer. Went to a lot of rock shows.

1997: Summer clerkship at a law firm between my 2L and 3L law school years, spent in a sublet studio apartment. A great, pretty relaxed and drunken summer at, probably, the last age and the last time in my life when that would be socially acceptable. On either side of that I was getting used to life in D.C. and rather enjoying it. Probably because none of my friends had anything to do with my law school. Went to California for the first time to visit my brother and other friends. We’re on 23 years and counting of me being convinced that I should live in California and not the places I’ve actually lived. Maybe one day.

1995: Graduated college, got married, moved to Washington for law school, started law school. Busy, eventful year. Maybe if that marriage had lasted and maybe if I still practiced law I’d rank these milestones higher.

1992: Spent the summer after freshman year back home and didn’t really know what to do with that. Had a rough patch with my girlfriend, who had joined me up at college that fall, that was hard on us both and that I still think about sometimes. Experienced my second depressive episode for sure. That entire fall was steely gray and the sky felt heavy.

1998: Graduated law school, moved back to Ohio, passed the bar exam and started practicing law. There was enough that was new and exciting and kinda scary that I think it distracted me from noticing how unpleasant a world I was entering.

1999: The unpleasantness started to dawn on me. I distracted myself by doing things like buying a house and getting into expensive wine and crap like that. I mark 1999 as the beginning of a bout of sleepwalking from which I did not emerge until I managed to actually leave the practice of law in late 2009. I’m 46, but I often feel ten years younger. I think that’s because I was basically in a coma for a decade.

1996: Law school and a summer clerkship at the DOJ. Both were drags. I wasn’t used to D.C. humidity and felt like I spent most of the year sweating. Kinda like 1999 except I was poor all the time.


2009: Got my dream job and came out of my coma. I once wrote 8,000 words about that. I put my law license on inactive status where, frankly, I hope it stays until I’m buried in the ground. But before that came a month and a half of shockingly clarifying unemployment during which I got to pretend to be a stay-at-home dad and rather loved it. Played with the kids and read to them all the time and read a bunch of graphic novels after they went to bed. Kind of a law firm detox. Then I got a job with the State of Ohio — we had to eat — and that kicked off an eight-month stint in public service which did a hell of a lot to restore my faith in the legal profession and made me realize that I did not fail as a lawyer. Rather, the private practice of law failed me and served as a poor use of my skills and my temperament. If the dream job had never happened I would’ve been OK. All that adds up to 2009 being a truly transformative year for me that continues to be — and likely always will be — one of the most important times in my life.

2003: I became a father. No, I am not ranking the experience of becoming a father below getting my dream job. Being a dad — the now 16+ years of actually being a dad, not one single moment or one single year — is the greatest part of my life. I’m just ranking years here, and since my daughter wasn’t born until December it’s not like I was a father for most of that year. I did take a fantastic road trip, though, during which I’d find out I was going to become a father and that was all pretty cosmic and life-changing. I also got a job at the last law firm I’d work for which, even though that’d end poorly, was pretty good for a while and definitely seemed pretty good in 2003.

2005: Became a dad for the second time. My son being born props up what was a really damn hard year otherwise, though. My father-in-law, who I loved dearly, died. The dark side of my law firm — and the dark side of my personality, which for a brief period my law firm brought out of me and which I did not fight — really began to show itself that year. Anxiety, fear, and having too much disposable income caused us to move to the suburbs which, nearly 15 years later, I’m still stuck in even if I wish I wasn’t. Seriously, Carlo: you being born REALLY saved 2005 for me. It’d be near the bottom otherwise.

2001: Went to Europe for the first time. That was cool. I think I’ve blocked out everything else that happened that year, personally speaking, even if I think of it as being kind of pleasant most of the way through. I really got into yard work. One of the lamer non-tragedies of my life is that I have always very much enjoyed mowing lawns yet, since that move to the suburbs, I live on one of those new-urbanist communities with houses on small lots and, what little grass exists, is maintained by the HOA. I haven’t mowed a lawn since the summer of 2004. It’s basically Greek tragedy.

2007: Started Shysterball, my little Blogspot baseball blog that would, over the next two years, turn into my new career. At the moment all I wanted was an outet where I could think about and write about things that were not unpleasant. With that I began the process of mentally checking out of the law, even if I didn’t quite realize it at the time.

2000: A total blur. I remember going to see “The Road to Perdition” at the theater one night with some friends who were visiting from out of town. Otherwise I was just in my office or home mowing the lawn or reading books. I think I leased a car that year. I have no idea why I leased a car. I have no idea what in the hell I did with myself beyond that. Like, I’m sitting here drawing a total blank.

2002: Basically an identical year to 2000 except I saw different movies and read different books. I went to Las Vegas at some point. I dunno. I was neither young nor old. I was not yet a father but I was not living a particularly free-wheeling life. I worked too much at a time when other people my age were still figuring out their life and that figuring-out-their-life thing seemed kinda cool from where I was sitting. I imagine they thought me having it seemingly figured out and owning a home before 30 seemed kinda cool. I wasn’t much for self-reflection at this point in my life. If I had been happy with my work instead of increasingly disillusioned by it, this is probably the time when I’d begin a 30-40-year stretch of just being some guy whose life could be summed up in a montage full of Midwestern professional class cliches. Like I said: kind of a coma.

2004: Was trying a lot of my own cases in court at this time but a great many of them were out of town. Had one in January in Great Falls, Montana. When I landed it was -22 degrees before windchill was taken into account. Had a month-old daughter at home I missed terribly. Had another in Portsmouth, Ohio, which required me to stay in a hotel in Portsmouth because my client insisted I do so rather than drive down. Between all that and adjusting to life as a father it was a hard year. One day in the fall I came home from work. It had been a rough day and I was grumpy. The baby had been crying all day and cried for an hour solid as I held her. The dishwasher had broken and leaked water everywhere. My wife suggested we order a carryout pizza. I called it in. When I got off the phone she said “I’m pregnant again.” I looked at her blankly, kind of in shock and unable to really process it. I said, flatly, “Um, I’ll go pick up the pizza.” She said, with genuine fear, “Are you coming back?!” It was that kind of year.

2006: The depths of my private legal practice which, ironically, coincided with my greatest success in legal practice. I made pretty great money — and I bought a BMW with it because, dammit, that’s what I was supposed to be doing, I thought — I was told I was on partnership track, and I was handling important cases and all of that. But it was dark. My wife had quit her job to be a stay-at-home mom, and that didn’t really suit her, which made things tense. My coworkers and I were at bars most nights after work which obviously didn’t help. I never did anything  truly irresponsible. I didn’t drink to the excesses that some of them did, I didn’t cheat on my wife or behave in ways that made people think I wanted to like some of them did, and I didn’t neglect my kids like some of them did, but I felt like I had to act, basically, like they acted if I wanted to put the ball over the goal line, career-wise. I wasn’t ultimately willing to do that, but it took me some time to get my mind around that idea. In the meantime I felt like I was being asked to choose between being a good husband, father, and person on the one hand, and, on the other hand, being a successful lawyer. It was tearing me apart.

2008: In 2007, after making the decision that I didn’t want to be a part of that ugliness — a decision I made via my actions, not consciously, by checking out mentally, spending more time at home with my family, and diving into more positive things — I was basically marginalized at the office for the next year and a half. I didn’t really realize it until September of 2008, though. That’s when the financial markets started crashing, tens of thousands of people were getting laid off each week, and the partner in charge of my firm took the unusual step of accompanying me on a trip to Kansas City to visit one of my clients. It became clear to me that he did so in order to get up to speed on my case because the firm was about to fire me. Which they did in October. That was bad. How certain people in my life reacted to it was worse, but we’ll leave that for another time.


I don’t talk much about work in this decade’s entries. It was the same job the whole decade. And, since I love it, it doesn’t cause the sort of agita that the old gigs did such that it might impact my year. For the most part career stress has been absent. And when it has suggested itself, it’s been in the form of high-class problems like “I wish I was more famous” or “why won’t someone give me a book deal.” As Joe Walsh said, I can’t complain but sometimes I still do.

Also: there’s not a ton about the kids here. Mostly because they’re smart and great and I’m constantly proud of them and that’s the sort of consistency which does not lead to annual variance. They were, and continue to be, the best things in my life.

Back to the years:

2013: It occurs to me that if you are reading this and do not otherwise know the general narrative of my life that you might not know that my wife and I split up in 2011 — I often think the seeds for that were planted in 2008 — and we finalized our divorce in early 2012. In between those two events I met a woman named Allison who would become my girlfriend and, eventually, my wife. Well, that did happen, so now I hope the fact that the worst but most explanatory years of the decade are at the bottom of the list won’t be as confusing. Anyway: Allison moved up to Ohio to live with me just before Christmas in 2012 and 2013 was a wonderful year in which we built a life together and with my kids that, after a few bumps here and there, we’re still enjoying.

I also got in pretty damn good shape that year. I had ballooned up to like 210 pounds in the mid-aughts but lost 25 pounds in 2011 — some stress-induced weight loss, but also a lot of time on my treadmill — and by 2013, the year I turned 40, I found myself lighter than I was in high school. That shouldn’t be as big a deal as I’m making it in this rundown, but I’m not gonna lie: there is a very strong connection in my mind between my physical health — with an unfortunately large emphasis on my weight — and my mental health. That’s probably also something else left for a better time, perhaps with my therapist.

2017: The year Allison and I got married. It was cool. I also began writing on this site a whole lot, particularly about political stuff, social issues and the like. It sucked that I was inspired to do that by Trump — definitely not worth it — but the process of writing more, and about different things, was and continues to be good mental stimulus for me, whatever the inspiration. Indeed, part of the reason I’m writing this now is that I was bored and feeling some mild ennui this afternoon but these days I now know that writing — writing anything — will almost always pull me out of it.

2012: Allison and I maintained a long distance relationship — her in San Antonio, me in Ohio — and we spent a lot of time in airports and hotels in the process. At the end of the year I flew down and the two of us drove her car back up here as she moved. They’re all good memories. This year is below 2013, of course, because being with her is far superior to being 1,300 miles from her, even if the travel was fun.

2010: My first year in the new job, during which I adjusted to being a full-time writer and working from home. I also transitioned nicely — and enjoyably — into being, for all practical purposes, a stay-at-home dad. I still dig it even if the kids don’t need me now the way they did when they were six and four years-old. People at the grocery store know me. For a long time I’d get put on every volunteer list at school and would be the only dad there among the moms. There are some folks — some teachers, some moms, and, like, ballet instructors and stuff — who don’t know how to deal with a dad doing these things. For a while it made life a bit awkward and I felt marginalized by the stay-at-home mom industrial complex at times, but I eventually got over it eventually and realized it was their problem, not mine. Anyway, a pretty fantastic year, probably the best I had had since I had been in college. Hindsight tarnishes it, though, knocking it down this list a bit, as I know now that it would be the last year in which my marriage was healthy — if it even was; I still don’t know — and I know now what was right around the corner for me.

2016: It started poorly. The worst depressive episode of my life began the previous summer (see 2015 below) and I got to a point where I couldn’t handle anything or deal with anything and I foolishly decided that that included my relationship, so I broke up with Allison. It was a terrible decision, caused by brain patterns which convinced me that if I eliminated anything even remotely difficult in my life, nothing could cause me worry.

Have you ever read an account by someone who jumped off the Golden Gate Bridge but survived? Almost every one of those people express some variation on the idea of “I realized as I was going over the railing that I could, actually, solve every problem in my life . . . except this one.” That’s kind of how that all went. I spent a month trying not to think about it at all but then two months realizing I had made a big mistake and trying to fix it.

But something else happened too: after a couple of abortive attempts at therapy in the previous few years I found a therapist who I connected with and who helped me understand what the fuck I was doing with my life, why I was doing it, and who taught me how to deal with it. I wish it didn’t take me descending into depression and screwing up my relationship to get that breakthrough, but dammit, it did. Yet, pushing four years later, it’s a breakthrough which still teaches me and pays me mental and emotional dividends. Whatever doesn’t kill you makes you stronger, etc.

Anyway: Allison and I got back together. Then we got engaged. Then she moved back in. The rest of the year was a wonderful time for me. I’ve not felt lost like I did early that year since. I feel like I have the tools and the strength — and the support from Allison — to handle whatever bad comes my way.

2018We went to England and followed James around on tour. Best vacation ever.

2019: It’s been a mixed bag. I had to put a cat down way before her time. I had a book deal in place that fell through for reasons that had nothing to do with the quality of the book nor the willingness of the publisher, and we’ll just leave it at that for now. There have been some financial challenges and pressures that I wish weren’t there, but as 2006 demonstrates, being in a financially secure position is absolutely no guarantee of happiness for me, so we just roll with the punches, right?

2014: Some growing pains with Allison. We didn’t break up but I asked her to get her own apartment because, after a honeymoon-like 2013, I was having a hard time of trying to balance dad life and boyfriend life and was worried that I was being a worse dad and a worse boyfriend than I needed to be. Even if we still spent a lot of time together we’d not live together for the next two years. We somehow made it work. Mostly because Allison has way more patience with me than anyone else would, God love her. This year ranks below 2016 because the bad stuff was not balanced out by any breakthrough or any enlightenment. I was just sort of flailing and wasn’t yet aware of the less-than-productive ways in which I deal with psychological stress.

2015: Depression hit me hard. Maybe it was coming on its own. My therapist thought it was because, even four years out, she said I was still not fully over my divorce, even if I truly thought I was. That wasn’t consciously on my mind at the time, but she was probably right. In the event the bad stuff hit after a series of little setbacks and disappointments, none of them particularly bad, but all of which just built and built until I got to a place where I caused myself not to care about anything or hope for anything. It was just a dull, flat, feeling that was so out of character for someone like me. I never want to feel it again. In any other decade it would’ve been the worst year of my life. But . . .

2011: My marriage imploded. And hell, it didn’t really start imploding until the spring and the imploding was done by October, so it was all packed into a shitty six or seven months, which somehow makes it worse. I’m past it now but I still don’t like to think too much about it. It was the most dreadful and traumatic experience of my life. The only things making it even tolerable to think about: (a) I ended up meeting Allison after everything went to hell, and she’s a hell of a woman; and (b) The next decade won’t have an entry this crappy. At least I hope.

Happy New Year!

Craig Calcaterra

Craig is the author of the daily baseball (and other things) newsletter, Cup of Coffee. He writes about other things at Craigcalcaterra.com. He lives in New Albany, Ohio with his wife, two kids, and many cats.

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