Dear Businesslady: Grieving at Work
by Courtney C.W. Guerra.
Dear Businesslady,
This is a personal problem that’s inextricably entwined with my professional life.
I’ve worked at the same place—in different roles—for eighteen years (!), and in many ways I owe my career there to a coworker who quickly became one of my closest friends. Not just a ‘work friend’ but a true friend—arguably a ‘best friend,’ even if that feels a little ridiculous when applied to someone you met as a full-fledged grownup. I initially felt intimidated by his smartest-person-in-the-room aura and the fact that he was clearly well liked by all my new colleagues (plus a few years older than me), but we hit it off immediately: two people who relished the opportunity to bust out a semi-snarky quip, but never felt competitive toward each other. I used to read in the lobby of our building so I could take my union-mandated hourlong lunch break without being inevitably interrupted at my desk (I was a receptionist), and whenever he walked by he’d faux-admonish me, “No reading!” Sometimes it was an invitation to talk that I took up; other times I’d just waggle my book at him in mock defiance. This form of interaction—a statement signifying something other than its literal meaning, an easy flow between conversation and individual preoccupations—became the framework for our friendship.
Within months we began carpooling to work, turning our epic commute into a beloved source of mutual entertainment. For over five years, we spent at least ninety minutes together every day, just … talking. We sometimes shared serious shit, but more often we were just developing an increasingly convoluted matrix of running bits and inside jokes—drive-time DJs with a loyal listenership of two. We had our occasional conflicts; punctuality is a struggle for me and he wasn’t shy about expressing his frustration when I made him late. But we never got sick of each other. We’d hang out on the weekends with our respective partners, and show up at each other’s office doors whenever noteworthy gossip emerged. We never would’ve used the terms ‘work husband’ or ‘work wife,’ but that was basically our dynamic.
Having him as a role model and ally unquestionably helped me get ahead in my job. I got promoted to a new position where my boss was another very good friend of his (and mine too; we made it work). Then I got another promotion and we started reporting to the same person. Because he liked and trusted me, he’d throw projects my way that helped me develop key professional skills, and because everyone knew we were tight, his stellar reputation reflected on me by association. He made me feel better about myself by association.
But nothing gold can stay. I ended up moving to a different city following my spouse’s can’t-refuse job offer, and although I was able to keep working at my org remotely—and meet up with my friend whenever I was back in town, which was often—we couldn’t possibly match the amount of literal closeness we’d once enjoyed.
Years passed, and this person who once embodied competence began slipping up.
He made bigger and bigger mistakes at work, including one that affected me directly. And in that instance—as opposed to those I could shrug off as none of my business or immaterial compared to his abundant accumulation of goodwill—I had no choice but to tell our boss. He’d made me look irresponsible in a high-stakes situation, and the alternative would’ve been to take all of the blame just to protect him. Not long after, in the wake of a growing disengagement that felt utterly bewildering to me, he lost his job in a massive round of layoffs. Then his distressingly self-defeating choices began to accelerate. He blew up his marriage to an awesome guy. He mentioned way too casually that he got busted for drug possession (not weed). I tried to do a mini-intervention—or whatever you call it when you psych yourself up to talk to a dear friend about their troubling behavior—but I could feel him shutting me out with every word. Then he suffered a horrible personal tragedy and moved away to live with his mom in another state.
Nevertheless, we kept in touch. I didn’t love the ‘I worry about you / you tell me something that makes me even more worried’ pattern we’d fallen into, and he stopped seeming to care what was going on with me, so it was easier to just send silly jokes and rehash shared references. To elide a lot of emotional turmoil on my part—again, please trust that there’s a lot of eliding in this letter, length notwithstanding—I learned to close off my deep affection for him. I didn’t think about our relationship too hard because it made me sad, but I never lost hope that my friend would someday emerge, phoenix-like, from this strange spot where he’d gotten stuck. Instead of saying “hey, I’m worried about you” I’d text a “Star Trek” meme and hope he knew that it meant I still cared. Sometimes he’d respond, and I’d feel relieved that he wasn’t too far lost. Sometimes he wouldn’t, and I’d try not to fear the worst.
I guess I’m starting to give away the ending. In May 2024, I realized that my every-few-months outgoing texts had gone unanswered since … scrolling up … last July? Shit, that’s not good. I broke my unofficial rule about keeping it light and sent a request for a proper catch-up—phone call or FaceTime, even. Ended it with “Miss you 💖.” Still nothing. Hunted him down on Instagram, but, after some brief back-and-forth there, more silence. Time kept doing its thing. In late July I almost texted him because I saw someone wearing a shirt that reminded me of a longstanding inside joke. (It said “It is what it is,” which we decided was something that only assholes say. This isn’t true of course, but it resulted in many faux-knowing looks exchanged between us whenever someone deployed it within our earshot.) But I got distracted and forgot to send that text. A little while later, I heard from his ex-husband that he had died. An overdose, while hospitalized with serious health problems. I’m told it was intentional. It happened the day after I came so close to texting him one last time.
Now, I keep having to break the news to mutual friends (he connected me to so, so many people) and colleagues. We were such a coherent unit for so long that folks still ask me how he’s doing. Every time, I feel guilty anew—both for pulling them into the orbit of my own grief, and for the fact that I couldn’t somehow stop this from happening. There are other ex-coworkers I miss and want to catch up with, but then I realize I’d have to tell them too. And while I wish I could tell the whole world how important he was to me, and how painful it is to lose him, I don’t want to flatten his whole life into some sordid, pitiable tale of decline—he was still a person even after he left my professional context, still vibrant and alive, making art and grieving and showing flashes of his trademark wit and charisma. It seems so unjust and unreal that he’s gone.
Ostensibly I’m asking you for advice here, so I guess my question is this: How do I, I don’t know, deal? How can I honor my friend’s memory—who he was as a colleague, and his whole self too?
—Professional Widow
(My friend and I both loved Tori Amos.)
Dear Mourning Tori Fan,
Before I begin to write through an answer, I should caution that I don’t have a solution to offer—because mourning of this sort is unyielding and immense, because I am but an uncredentialed work-advice columnist, and most importantly because I wrote the above letter myself in an attempt to process my dear friend’s death. (I’ve pulled this schtick before.)
And while it is indeed long, it leaves so many things out. Like how, even though the acknowledgments in my book span two pages, this friend’s name is not among them, because I was still fixated on the aforementioned work fuckup(s) when I was finalizing the manuscript. I didn’t even think about how unfair that was—how if I owe anyone gratitude for the arc of my overall career, including this advice-giving side gig, it’s him—until after he was gone. I still remember sitting with him in a bar near our office, accompanied by one of the many friends I’d never have gotten to know without his remarkable capacity to connect people, and floating a wild idea: What if I pitched a column to that new website The Toast? The fact that he didn’t scoff at it gave me hope that it might work. So, it seems fitting to use this format to document who he was and what he meant to me—and to raise some questions about the professional world where our friendship flourished, even if he ultimately left it behind.
I couldn’t write about him for more than six months, and I’ve struggled through writing this for nearly six more. Even though I’m omitting his name, I fear that he’s recognizable enough from this description that people who knew him, reading now, are finding out about this terrible loss. I’m sorry about that, just as I’ve been sorry every time I’ve broken the news. “That’s so sad,” people say. And I agree. He was so fucking good at his job, and at being a friend, and I’ll never stop regretting that he’s been robbed of the chance to do either. But it brings some consolation to know I’m not mourning him alone.
I thought I’d use the letter-to-self device as a way to summarize our deep history, but it was still so difficult to tell a story that has so many tragedies in the lead-up to its awful conclusion. As this piece rattled around in my head, before I got up the nerve to start typing, I’d torture myself with questions like: Should I mention the drugs? The story doesn’t really make sense without them. (It doesn’t ‘make sense’ with them either, but you know what I mean.) Yet it felt wrong, tattletale-ish to reveal an illegal, approbation-inviting detail about someone I once viewed as a mentor in addition to a friend. Eventually I asked: What am I worried about? That it’ll affect his job prospects one day? He is no longer alive. And then—like I do so often anymore—I started crying again.
My grief is intensified by the fact that I’m mourning two losses at once: the loss of my friend as I knew him, and the loss of the hope that I’ll ever see him again. I got so accustomed to holding him in my heart in a kind of stasis—wherever you are, I love you and I hope you’ll come back to us one day—that I have to consciously remind myself that there’s no ‘coming back’ for him anymore. How can I not blame myself for that, at least a little? He’d pulled away from almost everyone else we both knew, but I still had a chance to try to reach him, and I didn’t take it. If you’d talked to me a year ago (or five years ago), and suggested another intervention-type talk, I know what I would’ve said: that I was dealing with my own shit, and that it wouldn’t work anyway. The first thing is true and the second probably is too—he was not, generally speaking, a big fan of opinions he disagreed with, especially if they were critiques directed his way—but for all my periodic worries that he’d go too far and hurt himself irrevocably, I never let myself fully realize I might lose him forever.
Those are the things I often think while I’m crying. But I know that the self-recrimination is a coping mechanism—a misdirection, a mental trick. If his death is my fault, then it was in my control. If it’s within my control, I can divert my attention inward, identify the flaw, and fix it. I can find the perfect formula that, once applied, ensures that no one I care about ever dies again. Not on my watch!
It’s easier to bemoan my own inaction (and overlook the thorny complexities that prevented me from acting) than to accept there’s no clear reason, no acceptable explanation. He’s not here anymore, and it’s not and never will be entirely okay.
As I was working on revisions for this piece, I went back to Chicago for work, where my ‘office’ (more of a closet, ideal for a remote employee because no one else needed it) had been packed up to make room for a recent hire. Some of my old stuff was waiting for me in our newly designated ‘swing space,’ but a box was missing—a box that contained, among other things, a post-it note my friend had left for me welcoming me to my old office back when it was new. I have a photo of that post-it (I’d already been back to Chicago since he died) but that’s not the same. What I wanted was not the image-memory of his welcoming gesture, but the material that made that gesture enduring, yet precarious—its presence rendered powerful by its potential to be lost.
So, I found myself rummaging alongside our facilities guy (one of the very few people who’s worked at my org longer than I have) through boxes in the basement storage space that used to be my friend’s domain. I’d open box after box wondering, “Is this it?” only to see that, no—it’s just a bunch of promotional materials my friend helped design a decade ago, or some now-obsolete paper files I made the labels for in the nascent days of our friendship. My spouse and I have a saying, “God is a hack writer,” that we bust out whenever something happens in our lives that would feel like unreasonably overwrought symbolism if we encountered it in fiction, and … yeah. It was like being in an escape room about my own grief.
I thought about saying something to my colleague—someone who I’ve known for nearly 20 years, a good guy I’ve always been fond of—if only to explain why I was so insistent on finding this box filled with mostly junk. But then I thought about how odd it was that he hadn’t asked after my friend; he usually did. While I can’t say for sure, it felt like his silence—and his shared determination to help me track down this random memorabilia—was a sign that he already knew. And whether or not he did, his being there was important, in a way that’s rarely acknowledged in a professional culture that venerates maximum mobility. He did know my friend, and that couldn't happen with someone who was new, endlessly mobile, incessantly ephemeral. No disrespect to folks who’ve enhanced their careers by switching jobs, but dislocating us from communities of time, and forcing only communities of pre-recognized affinity, is one of the ways contemporary workplaces and society keep us as empty as possible. You can’t benefit from the bedrock of ‘that person who's been here 20 years’ when ‘being at a place for 20 years’ is seen as a sign of stagnation, not steadiness worth celebrating. (And you certainly don’t get to keep that person around amid an ethos of laying off the long-timers to hire blank-slate replacements at lower salaries. But I digress.)
My friend worked closely with our trusty facilities guy, but he made an impression on people who knew him far more tangentially—fleeting acquaintances have surprised me by remembering him. Even so, it’s hard to express what made him special. How do you condense a legacy of accreted moments into a few paragraphs? I can’t help but describe him as charismatic, but that’s so often used as a shorthand for ‘charming, but an asshole,’ and that’s not what I mean. He didn’t wield his charisma as a weapon. He was fundamentally kind—he just quickly lost patience with anyone who didn’t earn or return that kindness. He was critical, not in the sense of ‘judgmental’ but as in ‘critical edition’—a source of focused, well-informed assessment. (And, during the time we worked together, in the sense of ‘essential.’) He was a problem-solver, the person you’d call if an esteemed guest was coming on short notice and you had to pull together a fancy dinner with an engaging cadre of attendees who wouldn’t embarrass themselves or our organization. He was the guy who looked at a clunky analog registration process for a major event and developed a tech-based solution that’s still in use, essentially unchanged, a decade later. When I picture him at work, I remember him as a kind of roving orchestra conductor—arms out, hands gesturing, sharp blue eyes sparking, stylish shirt coming untucked from his trousers as he rotated around sketching out ideas in the air: The flow of people, the placement of chairs and posters and lecterns. (I wrote “podia” at first, before remembering that he taught me the difference between a lectern and a podium. Good-natured pedantry was another of our commonalities.) Even though he had a firmly white-collar job, his thick fingers evinced some ruddy Irish-peasant ancestry, always cracking during our dry Chicago winters no matter how many times he slathered them with his little green tub of Working Hands.
We never would’ve met without work and work was where we forged our friendship, but we talked about so much that had nothing to do with our jobs. We had a rich tapestry of shared bits, ritualistic phrase mantras we’d repeat endlessly—like pretending to correct one another in flagrantly incorrect ways (e.g., I’d reference St. Louis, he’d say “I think you mean ‘St. Louise’”), and doing it constantly, whenever certain trigger words were mentioned. Another was from the reality show “The Hills,” which I never actually watched, but which was featured heavily on the clip show The Soup, one of our shared cultural affinities. It’s an exchange between two protagonists observing some fashion item with a feather motif.
First person: “I love that it has feathers.”
Second person: “We love feathers.”
This call-and-response was so embedded in our intimacy that I told him I was pregnant by texting a photo of the label from a pair of leggings, featuring the brand name “Feathers Maternity,” prefaced by “some personal news🧐🤯” (There were many, MANY other iterations of this joke over the years, but that was arguably its culmination.)
A few days after I learned he was gone, I found a feather on the ground behind my house, which was miraculously still there a day later—I was shocked it hadn’t blown away in the wind. But it stayed. I took it as a sign, cleaned it off, and kept it. So that’s one piece of advice, from me to me: Hold on to whatever talismans give you comfort as you grieve. I found more from my own archives too, gathering digital photos, rereading all our text messages, getting out the homemade card he sent after my kid was born.
One of my many regrets is that he never met my kid, who’s newly 5. But my kid knows his name, and that remembering him makes me sad sometimes. While his understanding of death is age-appropriately nebulous, he knows my friend is gone—that I “lost him,” which I think in his mind means we got separated in a crowd and never managed to find each other again. In a way, that’s not too far off. While driving up Lake Shore with my family—something I hadn’t done since he died—I told my kid it was the route we used to take home together during the carpool days, and got choked up; he sagely explained to my mom that, “Whenever Mommy talks about [her friend], she gets emotional.” I hadn’t expected it to hit me like that, but being in that physical space again—the car, the road—was overwhelming. So many drives, so many days. It was typically him behind the wheel, and I can still picture his hands gesturing against and around it, see his face in profile narrating some complex quotidian ordeal or crinkling his eyes as he laughed at a tossed-off comment—mine or his own.
I’ve been trying to find ways to remember and celebrate the things he loved—he had so many nerdy passions, some of which we shared (LOST; TNG, and he was right that I should’ve gotten into DS9 sooner; Tori) and others that were his alone, like Legos, which I hadn’t been particularly into since childhood. But now I have a child of peak Lego-enthusiasm age. Through a combination of parental indulgence and mournful sentimentality, our family visited the Lego store and bought a ridiculously complicated train set, which it turned out our kid was surprisingly proficient at assembling. It came with a little diorama of a rainforest, one of those ‘adult’ Lego kits aimed at people like my friend. I thought putting it together would make me feel closer to him, and it has—although my kid, remarkably, was the one who actually did the construction (with some attentive project-management on my part, I’ll concede). It has a little toucan figurine, and when my spouse saw that, he quipped, “I love that it has feathers.”
This column is about my friend because this column [gestures broadly at over a decade’s worth of posts across three different blogs] is about my friend. All the things I’ve come to appreciate as true measures of career success—building relationships, achieving things that inspire you, finding true companionship and camaraderie amid the mandatory capitalist hellscape of employment—are things he modeled for me. He helped me create a career for myself that felt like home, and once I achieved it I wanted to help other people find the same thing. I’d managed to leverage a double-major in English and visual art into a financially sustainable job I enjoyed, working alongside my best friend and a bunch of other colleagues I genuinely, sincerely liked, many of whom I’m still close with today. That made me feel qualified to position myself as, if not an expert, a reasonably well-informed discussant on employment and workplace nuances—to become a version of my friend, but for a much wider audience. My job is where I realized that a ‘work friend’ could be more than just someone to commiserate with—that it could be someone who made your work better. Not every workplace lends itself to friendships, and not every coworker is cut out to be a friend. But there are still opportunities for connection, for something more than siloed simultaneous labor, and there's value in forging those connections where you can. The friendships, if they happen, can’t develop without a baseline sense of community, of camaraderie, of mutual care.
But the downside of finding a job, and coworkers, that you connect with emotionally is the downside of any emotional connection: You can get hurt. And it also means things get thorny when your work friend starts causing problems at your workplace, or effectively drops out of the workforce entirely. It’s already tough keeping in touch with folks who depart an org before you do, or who you leave behind when you find a new gig—it’s harder still when they start going down a path that feels fundamentally foreign to your understanding of who they are, and who the two of you are together.
The responses I’ve heard from current and former colleagues—it’s such a loss, how sad, what a waste—were already part of the chorus when people asked me for updates about him in recent years. For some people I’d just demur entirely, but with genuine friends I’d be more candid.
“Is he working anywhere?”
“Not really—delivering for Instacart last I heard.”
“Oh, what a shame.”
And it was. But is someone obligated to maintain a particular professional profile just because they excel at a specific set of tasks? When your life goes off the rails, shouldn’t you be allowed to retreat, to move back in with family, to leave behind the kind of work that entails international travel and massive logistical coordination and late nights ensuring that everything’s just so?
Steeped in the ‘line going ever upward’ compulsions of capitalism, we’re trained to identify a worthy, productive life through the continual conferral of raises and promotions. Anything less is either a challenge to be eventually overcome with a return to that same trajectory, or a failure. I can’t pretend my own career didn’t begin as an attempt to succeed by those same metrics, and when my friend’s brilliant productivity began to falter, I can’t pretend that I didn’t spend time feeling furious that he’d failed not just himself but our whole organization. I’m still a little angry with him, if I’m being honest, because he bears some responsibility for the fact that I don’t get to talk to him anymore. And I’m angry at myself, for letting our ‘work friends’ origin story get in the way of reaching him as he began his descent, for failing to fully connect with the person he became. But I’ve become far angrier at the larger system, for shoving him out of the way when he started stumbling, for scrambling his friends’ ability to help and his ability to help himself. If there’s any truth in the idea that ‘it is what it is’ is an assholish saying (beyond the snarky joy it brought us as an allegation), it lies in the implication that we have to just accept our shittiest circumstances, absolved of the endless, thankless work of fixing them.
There are plenty of people who find themselves struggling in their jobs, for whatever reason, and as a society we have precious few support systems that allow those people to take a break. And our workplaces tend to replicate a systemic relish for relentlessness. We talk of ‘resume gaps’ in hushed tones, as though a period spent raising a child, or caring for an ailing loved one, or contenting with one’s own health problems (mental or otherwise), or simply not being able to find a job for a while is somehow a personal failure—one that will, and moreover ought to, follow you around and diminish your professional prospects forever.
I hate this, and I hate it even more now that (as you may have heard) there’s an unprecedented wave of incredibly competent, dedicated federal employees who are newly unemployed and likely traumatized. I hope they all manage to keep going, find new gigs, tap their savings accounts, lean into healthy ways to cope. But some won’t. What are we imagining we can do for them? For us? Because none of us can know what alchemical combination of life events and brain chemistry will send us into a deep, self-defeating spiral.
Back in Chicago on my work trip, I came back from a meeting to find the missing box sitting on my loaner desk. My colleague in facilities, clearly, had kept up the hunt on my behalf. An act of care. In it were the sentimental totems I expected, from my friend and otherwise—that post-it, swag from a visit to the NEH offices in 2019, a sticker from Hillary Clinton’s presidential campaign. I realized, looking at them, that I was mourning much more than just my friend, that his loss is amplified by so many other overlaid losses—the broader social and societal ones I’m aware of, and all the granular, personal collateral damage I’ll never know about. But there were treasures in there too, like a laminated version of the paper forms (!) we used to fill out when processing expenses. My friend had made it for me as a guide in the early baby days of my admin job, back when we first met—a simple collegial kindness I never would’ve remembered without a physical memento.
It's my practice, in these columns, to end on an optimistic note. But this is not an optimistic story. It’s not an optimistic era. “These programs that are gone, they can’t just be built back,” observers warn, and I am all too aware of how precious things can be suddenly lost forever. Yet no nebulously empowered government agency can take away our capacity to care about other people, and to make that care durable. To show that they are loved. That they deserve support, and respect, no matter the distance between their present circumstances and the life they might have once imagined for themselves. And in the showing, we must do what we can to create something—a document, an impenetrably ridiculous inside joke, a piece of art, a law—that allows the world you shared to persist.
In a Facebook post right after the 2016 election (one of his last before he largely disappeared from social media) my friend wrote, “Are we going to get through this? Yes, by taking care of each other.” I wish I could’ve taken better care of him, and I wish he’d taken better care of himself; the bitter irony of that statement is not lost on me. But he’s right. As we fight for the future—of the workplaces incentivized to ignore the humanity of their resources, of whatever country we inhabit, of the planet that we desperately need to protect—we will need people to share and lift our burdens. To interject levity into the most bleak and stressful of situations. To extend grace and compassion for our mistakes. To see us as more than the fruits of our labors, paid and unpaid. To keep us from losing hope and giving up. We need work friends for the work beyond the workplace, as well as within it.
To quote Emily Dickinson, even though my friend would’ve rolled his eyes at me for it: “‘Hope' is the thing with feathers.”
(We love feathers.)
This edition notwithstanding, Dear Businesslady remains an advice column for actual people. Need help with a career conundrum or workplace woe? Send a letter to dearbusinesslady@gmail.com.
Comments ()