I didn’t set out to be a writer. Like countless others who’ve gone on to carve out a living in cultural commentary, my youthful dreams centered around making art myself; at first, I only wrote about others’ work because it was easier than working past the obstacles that kept me from doing the stuff I really wanted to do.

This is (obviously, I hope) not to say that I didn’t love music, or that I wasn’t passionate, one way or the other, about any of the albums I reviewed. But observing pop culture was, in my younger mind, a gateway that offered a fun interlude between daydreams about learning how to play guitar and making enough money to afford session time in a recording studio. Like the majority of the career decisions I’ve made in my life, it was a lark.

Eager to avoid hard work and emboldened by the arrogance of youth, I didn’t give any serious thought to developing my voice or refining my message. For years, everything I wrote was little more than blurting — like any major fan, I was always chasing the dragon’s tail, looking for that next big high, and the writing was just a byproduct, a chronicle of that journey. It was mine, and as long as I was honest, I felt like I was doing my job.

That was true enough on one level, I think — I kept getting paid, anyway – but it was a fundamentally flawed approach. Absorb enough of anything, and you’ll acquire a level of context that allows you to discuss the subject with a facsimile of intelligence; top that off with a heavy layer of opinion, and you’ve got yourself a safe fallback position for a critic. You can make reasonable arguments from here.

Yet — like my reasons for taking the gig in the first place — it’s a shortcut. It has the form of cultural criticism (and it seems to be plenty for a lot of entertainment writers), but it doesn’t serve the function. It has no insight to offer; it lacks the ring of truth. It’s missing empathy. Like a bad soul singer, it tries to use volume to cover up for a hollow core.

It was probably a decade before I started feeling these twinges — caught the first real glimmers of what my writing lacked. While serving as the music critic for a local paper in 1997-’98, I temporarily abandoned reviewing new releases, embarking on a weekslong quest to explore the essential spark between yearning music and the receptive listener. I framed it under the Latin question “Quem quaeritis?” — “who do you seek?” — trying to sum up, somehow, the echo in the human heart refracted by the works of art that truly speak to us.

A foolhardy endeavor, to say the least, and one doomed to sputter into oblivion in 500-word chunks by a haphazardly edited, hardly read weekly. When the paper puffed out of existence, fartlike, I figured the quem quaeritis columns were about as good a place as any to call it quits — the phrase is most commonly associated with a liturgical drama, a question posed to Christ’s followers after they show up at his tomb, and any thoughts I’d entertained regarding a writing career were buried.

It took a lot longer than three days, but they eventually came back — although again, there wasn’t much in the way of foresight or true dedication. While working as a graphic designer and prepping for a teaching career, I started keeping a LiveJournal that eventually expanded into a forum for ruminating on pop culture, which in turn bulged out into Jefitoblog…all while a series of unexpected job opportunities lured me further from the classroom and kept me at the keyboard.

That was roughly 10 years ago, and it’s been a decade of decidedly good fortune for me — I don’t think a day has gone by without me pausing at some point to reflect, however briefly, on how incredibly goddamn lucky I’ve been. I’m good at what I do; I know this. I turn in clean copy, I don’t miss deadlines, and my lengthy obsession with pop culture has qualified me for a wildly eclectic array of assignments (including a book about One Life to Live and a book about beer).

Against all odds in a mean freelance economy, I’ve managed to pay the bills through writing for a very long time. Maybe that should be enough. And yet.

I don’t know anyone who doesn’t struggle with self-doubt to some degree, and as writing slowly revealed itself as my calling, I’ve grappled with plenty of my own. Again, I didn’t have a plan for this — and when my semi-private musings about the music, books, and movies that moved me attracted an audience, I found myself increasingly unsure of how to proceed. Why were people reading this stuff? What were they responding to? What next?

Following the muse through a feedback loop is one thing, but keeping track of it while earning a living is something else entirely. I haven’t always done a very good job of maintaining that balance — in fact, much of the time, I’ve been completely lost. Faced with the opportunity to start a new website after Jefitoblog went under, I spearheaded the development of Popdose, a site whose staff was initially comprised of my favorite fellow pop culture bloggers — but as time wore on and it became increasingly clear that turning a profit was never going to happen, some of those writers fell away and new ones climbed on board, and along the way, the site’s overall aesthetic no longer really fit the style of writing that had put me in position to found it in the first place. More and more often, I’d consider pursuing a piece, only to decide it wasn’t a good fit.

The online landscape altered, too, with an influx of corporate cash and an attendant wave of buyouts, sellouts, and consolidations spilling over into a cascade of changes — the slow death of RSS, the rise of social media-driven traffic and subsequent dispersal of many comment-section communities, the coronation of the almighty SEO, the birth of #content. These developments dictated a style of writing that demands quantity over quality, conformity over creativity. I piled up more and more assignments that required less and less thought.

The only alternative — as far as I can tell, anyway — is to hustle after bigger freelance fish. I admire the hell out of writers who do this, but I don’t have the stomach for it — a realization I came to while I was in the thick of writing my first book and I truly didn’t have time to contend with editors whose favorite method of declining a pitch was to simply not respond at all. If your choices are to crank out tons and tons of work that you’re not always proud of or to risk going broke while darkening the inboxes of strangers, what do you do? Again, I often chose the path of least resistance — a decision repeatedly reinforced by the minimal reception that greeted the stuff I really did put a lot of thought and effort into, like podcasts, longform pieces, and editorials on the state and future of the music business.

I’m not apologizing for this. I have a family to feed, and just as importantly — I can’t stress this point enough — I love the people I work with. I’m not naming my steady gigs here; I’ve had them all long enough that if you’ve bothered to read this far, you probably know what they are. They’re outlets stewarded by good, compassionate, creative people who understand the pressures of the marketplace and bear their responsibilities with more dignity and grace than I’d ever be able to manage. Of all the lucky breaks I’ve caught over the last 10 years, ending up with this group of editors might be the luckiest.

All of which is a very long way of leading up to some of the underlying factors contributing to the deep professional funk I stumbled into last year — and the guilt that mingled in with my self-loathing, steeping into a pungent brew that kept me drunk on a state of terrified misery for much of the last six months of 2015. It started, as these things do, with a relatively minor setback — the majority of some work a publisher commissioned for a book ended up being held over, leaving me with a relatively minor contribution (and payment) instead of what I thought we’d agreed on — but it triggered an emotional landslide.

Again: I didn’t have a plan for any of this. Even if I was no longer the callow kid who lacked an understanding of what goes into creating art, even if I’d spent years stripping my writing of inessential parts and trying to honor my craft, my career was still, in a very real way, something that had happened to me instead of something I’d built. Stung by doubt, I looked around and wondered if I’d strolled blithely into a dead end. Would I ever make enough to retire? Would I end up a 70-year-old hack, setting aside weekends to churn out copy whose eventual publication was always subject to the whims of executives I’d never meet?

Would I ever write anything that really mattered?

And what in the world would I do if I wasn’t a writer?

Or maybe I wasn’t even a writer after all. I’d unmoored myself from Popdose, I hardly ever write here, and whatever audience I ever had has long since dispersed. I watched friends and peers contribute to the pop culture conversation, weighing in on this and that via social media, posting pieces and publishing books, and I sunk deeper into my emotional hole. There was a part of me that wanted to claw my way out and see if I could elbow a path back into the discussion, see if anyone was interested in what I had to say, but I stayed in the mud, wallowing in fear and envy.

I didn’t really talk about these feelings as I was experiencing them, partly for the same reason I’m having a tough time writing about them now — it’s difficult to articulate the source of my misery, and even harder to describe them without feeling like the world’s whiniest man. I only try because of the small but persistent voice telling me I’m not alone, saying freelancing can be lonely by nature, reminding me of the delicate blend between faith and doubt whose tension fuels creative work.

I’m not an unhappy person. I’m happily married, I have two smart, well-adjusted, healthy kids, I’m a homeowner in a nice neighborhood in a beautiful part of the country and lots of family nearby. By any measure, I’m incredibly fortunate — and I spend a lot of time thinking about this fact and feeling fortunate for it. So if I’m susceptible to wandering into a dark place and risking the unlucky Zork explorer’s fate of being eaten by a grue, then I suspect it’s probably high on the list of occupational hazards.

I wish I had some words of wisdom on the subject — a map out of the dark places — but of course, it doesn’t really work that way. All I can say is that I spent months feeling lost, convinced I wasn’t writing a word that made a damn bit of difference, wondering whether I was qualified for any of a hundred khaki-clad office jobs. Wondering whether it would be better to turn the creative impulse into a hobby, or tamp it out entirely. For me, the light came through another of those countless fortunate twists of fate — one that opened a window of communication I didn’t even know existed, which in turn exposed professional possibilities I had no idea were there. It offered me a reminder of my value when I needed it most.

This all leads me — in a very, very roundabout way — to the album of the moment here at headquarters: Emitt Rhodes’ new Rainbow Ends LP. Announced late last year via a successful crowdfunding campaign and attendant Wall Street Journal single premiere, Rhodes’ latest 11-song set snaps a drought of more than four decades between releases from the cult-hero singer/songwriter. As he explained to the WSJ, an artist can have his creative back broken whether he’s a middle-aged monkey at a keyboard or highly regarded recording act:

“I worked very hard, and it was as if I wasn’t working hard enough,” he shrugged when describing the days after his last album, 1973’s Farewell to Paradise. “I just burned out, is what I did.”

The time off turned him into something of a legendary figure for fans of sophisticated pop with a bittersweet tinge, but it also clearly did him some good: Rhodes sounds like time stood still on Rainbow Ends. This makes a certain amount of sense, given that a number of the songs are compositions he started cataloging in manila envelopes starting in the late ’70s, but this is no retro endeavor. It’s rooted in the lush arrangements and classic songcraft that listeners of a certain age will forever identify with his heyday, but it doesn’t sound dated; the songs are brought into fresh three-dimensional relief by producer Chris Price (who spent 10 years shepherding the record to its conclusion, and is the hero of this project) and an all-star band of L.A. session players that includes veterans of Wilco, Jellyfish, the Bangles, and New Pornographers.

It’s a tricky thing, this business of hearkening back to an earlier era, but Rainbow Ends pulls it off with aplomb. As I told my dear friend and musical brother Jason Hare, it sounds like a lost Andrew Gold record — musically, melodically, and definitely lyrically, with lots of lines about broken hearts and lost loves. It’s an album out of time — Mellow Gold for a new era.

That last bit might sound a little dismissive, but it isn’t meant to be. Not that you’d know it after I spent 2,000 words talking about my insignificant problems, but I think it’s tough to sing sensitively about heartbreak without coming off like a simpering doormat. Rhodes does it again and again on Rainbow Ends — if you’re the type of person with a soft spot for this stuff (and I obviously am), and if you have memories of spending your own miserable nights wondering what the errant object of your affection is up to (scroll down a couple dozen entries here; yep, that’s me too), listening to the album is liable to fill you with bittersweet recognition. Rhodes captures longing, self-recrimination and regret — and indeed, he’s said a real-life heartbreak sparked this album — without making it feel like a wallow.

“I had a spurt there, you know. I just wrote a whole bunch of songs. I’m just gonna write what my heart tells me, because that’s the only thing that really matters, isn’t it? Sometimes you don’t know, and then the light goes on and you do know,” Rhodes explained in the press release announcing Rainbow Ends. “The music is very good on this record. I think that these guys are all wonderful players and there’s all sorts of interesting stuff. I hope people like it, and I want you young guys to be able to get your due. I think whenever it happens, it happens on time.”

I don’t even want to try and speak for Emitt Rhodes, and I’m not trying to equate my own experience with his long hiatus. But writing this while listening to Rainbow Ends, I couldn’t help imagining what it may have felt like for him to be persistently persuaded back into action, to hear his songs being brought to life by this talented crew of musicians, and to watch the PledgeMusic campaign reach its target. I’m sure he must have known, on some level, that people missed him and that there was an audience waiting for new music, but I don’t doubt he was pleasantly surprised by their number, and gratified by the enthusiastic wave of press that greeted the announcement of the album’s release.

Sometimes you don’t know, and then the light goes on and you do know. Whenever it happens, it happens on time. There’s obviously more to the story than that, but even after devoting all these words to my own recent struggles, I’m not sure I can sum it up any better than Emitt. There are lessons in the darkness, and the breaks, bumps, and bruises we incur while fumbling blindly for them may make us stronger in the broken places — and leave us with deeper empathy for our fellow travelers — after we’ve healed. I’m personally still sorting out the steps that led me in and out of crisis, but they’ve left me with a renewal of purpose and a clearer idea of my creative path’s shifting contour. If you’ve stayed with me thus far, I hope you’ve been able to make some sense of the journey. Whichever parts of you are in shadow as you read this, I hope the light goes on, and I hope it happens on time.