I was twenty-three years old with a hand-me-down diamond ring on my left hand, business cards, and a salary that was real this time, not a mere stipend. I took myself rather seriously at that point and felt like the tumblers of adulthood were clicking into place. Engagement: click; real job: click; living with Nate: click. I was only forward-looking, always pressed into the wind, craning my neck to see what I could achieve next, what more I could cross off of my unending list. I saw the present as my platform for launching into the future, not as something with any merit of its own. There was no resting on laurels or enjoying of the moment for me. Nate and I decided to renew the lease on his basement apartment in Cambridge because it was cheap and conveniently located. We agreed we needed to save money for our future, an amorphous concept, but one which we knew would require more than the combined $8,000 we had in the bank. We wanted to be together and we didn’t care that the only sunlight in that apartment snaked through the partially subterranean windows for about an hour every afternoon. It was like trying to line up a Stonehenge equinox to catch an ephemeral ray on your bare forearm.
I’d grown up hearing my parents’ stories of their first home, which was a tiny two-story in Denver furnished with hand-me-down furniture from my great uncle’s dental practice waiting room. In the summers, it was so hot in their unair-conditioned bedroom that they dragged their mattress down to the cool basement, which had a concrete floor with a drain in the center. Nate’s parents scrimped for years to put a down payment on their first home, a nine-hundred-square-foot, brown-carpeted bungalow in Miami with a back porch bigger than the entire first floor. These were the guideposts Nate and I followed. We had no expectation of hardwood floors or new paint or matching silverware. We were both taught that frugality is woven through your early years, that it’s integral to how you build a life together. Debt wasn’t something either of us ever considered. Living in wealth-saturated Cambridge—home to Harvard, MIT, and a lot of trust funds—Nate and I realized we weren’t doing as our peers were doing. They’d upgraded to two-bedroom condos with stainless steel appliances and newly refinished bathrooms. They ordered matching furniture to be delivered from West Elm and Pottery Barn, while Nate and I stuck with the once-white hide-a-bed couch that’d been in the apartment when he moved in. We went to IKEA in a rented car for the rest of our furniture and assembled it ourselves, which at the time I mistakenly thought was the height of frugality.
A month after Nate proposed, and a month before leaving New York City, I was hired as a development associate in the major gifts department at WGBH, which is Boston’s NPR and PBS station and the producer of many PBS programs. Since I’d started in development after picking that fund-raising drop-down option for AmeriCorps, I figured the quickest way to advance was to stick with the same field. I knew the terminology, I understood the basics, and I was pretty good at it. Plus, I had the golden résumé goose of “one year of relevant experience.” I didn’t consider fund-raising my passion, but I didn’t actively dislike it either. I was more interested in climbing through the ranks and increasing my salary than I was in doing something I “loved,” because I didn’t think doing something I loved would bring me any conventional recognition or notoriety. I wanted people to think I was successful and, as far as I could tell, the best way to get there was through a career. More to the point, I wasn’t even sure what it was that I loved doing in the first place. I liked to write, but that didn’t sound like much of a career to me. I thought getting a solid job was the consummate achievement, and development associate was a step up from AmeriCorps development associate. It didn’t occur to me that there was any other path to follow.
Sitting in my assigned cubicle at WGBH, all I could see was gray. The patterned fabric of the cubicle enclosure was gray, the weapons-grade edges of my metal filing cabinet were gray, my plastic desktop was gray, and the wall behind it, also gray. Staring at the unforgiving rectangle of my computer screen, I was trying to think of a synonym for “generous” while writing a thank-you letter to a donor. I’d opened with “thank you for your generous support” and I couldn’t very well end it with those exact same words. I could hear my cubicle neighbor clacking away on her keyboard. She sounded so competent, so decisive with each keystroke, and I imagined her flying through her daily tasks while I pondered the meaning of the word “generous.” I wondered if I was the only one who labored over each sentence, considering it an opus, a monument to the career I wanted to build. I settled on “meaningful philanthropy” and pressed “print.” My entire year in New York felt like one long, held breath. This was it; I’d finally arrived into adulthood.
Most Mondays through Fridays I sat in my grayscale cubicle on the sixth floor, banging out thank-you letters, proposals, and reports on how our donors’ donations impacted the organization. But the summer after I started, I was tasked with planning the logistics for a fund-raising event at a donor’s second home on Martha’s Vineyard. I’d never been to the Vineyard before, but by this point I’d been inside a number of unbelievably wealthy people’s houses, mostly on Beacon Hill. Parachuting into the upper class is part of a fund-raiser’s job. Although I wasn’t senior enough to actually ask these people for a donation, my boss, Ellen, whom I worshipped, sometimes took me with her as a sort of note taker/posse member. I’m articulate, I don’t take up much space, and I have very neat handwriting and an ability to capture details from a conversation, all valued qualities in my profession.
I put together an invitation list, which entailed typing out the handwritten names the donor faxed to me, pulling lists from our database, and then mailing out the invitations. RSVPs trickled in and I dutifully recorded whether Mr. and Mrs. VanDam would arrive together or separately, and then made name tags for everyone with a WGBH logo at the top that took me the better part of three hours to line up correctly. Minutiae was the business of my days. Correctly spelling, and knowing, that Professor Rochelle M. Daughtry prefers to go by “Buffy” and that her investment banker husband, in all seriousness, goes by “Bick” was the currency of my role. I arranged for a caterer, unsure what canapés were until I googled them, and hoped that an open bar with only beer and wine didn’t reek of a middle-class suburban wedding reception (that being my experience with open bars up to that point).
Usually Ellen was the one to actually attend these events along with her boss, Win, the vice president of development, but Ellen couldn’t go and decided to send me in her stead. I did not see this as a good thing. There are so many elements to an event, all of which can go wrong, and all of which the event planner is blamed for. There’s a myth that being an event planner is fun because you get to attend an event. But I find that being an event planner is horrifically stressful because you have to attend an event. All of the guests are munching those canapés and throwing back that free beer and wine while you’re stress-sweating through your inconspicuous dress, praying that the sound system doesn’t crackle when the opening remarks begin, feigning polite conversation, and wondering why on this green earth you didn’t wear flats as you shift your weight from the front of your high heels to the back trying to decompress your toes during your fourth hour straight of standing on a concrete floor (every floor feels like concrete after standing on it for four hours straight in high heels). Despite my feelings on all that, I couldn’t very well say I wouldn’t go. So I tried to convince myself it was a chance to impress my boss’s boss—the doyenne of fund-raising, beautiful, stylish, and immaculate in speech and written word—Win.
Three weeks to the event and I already had sweaty palms and nightmares of me toppling a pyramid of wineglasses at a crucial fund-raising juncture. It was decided Win and I would arrive separately, so I left my apartment at 6 a.m. on the morning of the event to allow enough time to walk to the T station, take the train downtown, transfer to another train, walk a few more blocks, ride a bus to the ferry station, take the ferry over the ocean to the Vineyard, and then take a cab to the donor’s (second) home on “the island” (as it’s known by those in the know, which was most certainly not me).
I quite like traveling alone so while bumping across the ocean on the ferry, with the August sun on my face and salty spray hitting my powdered nose, I forgot where I was going and relaxed into it, smiling for a moment before self-induced pre-event panic weighed down the corners of my mouth into the grim line that constituted my event face. I turned away from the ferry railing and walked inside the boat to sit on a low bench where I could obsessively check the spelling on the name tags in my bag—not that there was anything I could do about an error at this point, being, as I was, on the open ocean.
When the cabdriver pulled up to the address I’d given him, I was certain he’d gotten it wrong. Similar to my arrival at my graffiti-laden Brooklyn walk-up, the property in front of me did not meet expectations. Our donors had described this—their summer home—as “a little Vineyard cottage.” In no way were “cottage” or “little” the terms I’d use. As I climbed out of the cab in my sundress and sneakers, which I’d worn on account of the many blocks I had to walk during my three-hour trek to get there, I stood back to take in the estate soaring before me. I walked up to the carved wooden front door, reminiscent of a Frank Lloyd Wright masterpiece, and hoped I was in the right place since there was no way I could hail a cab on this secluded street, and I didn’t have cell reception.
Feeling like a disheveled, overaged Girl Scout, I knocked. The donors could not have been more gracious as they gave me a tour of the grounds and fed me lunch. Mercifully the caterer showed up on time. I dragged a not-too-priceless-looking table in the massive foyer (larger than my apartment) into service as my name-tag command center. There were several hours to go until the event. Having already set up the chairs, arrayed the handouts, and organized the name tags alphabetically, I awkwardly loitered in the donors’ cavernous kitchen, where they’d told me to “eat anything you like.” I furtively took a bottle of water and an apple because they were the closest items to me and the only things that wouldn’t involve me digging through their $20,000 refrigerator; which, by the way, I couldn’t find for ten minutes on account of the fact that the exterior was handcrafted wood to match the rest of the cabinetry. I had no idea people had handcrafted refrigerator exteriors. I put the empty bottle of water and the apple core into my backpack because I couldn’t find a trash can, figuring it was probably custom-built into a wall somewhere.
Win arrived as scheduled, an hour before kickoff, and I took that opportunity to slip into the guest bathroom and change my clothes. I’d brought my “event outfit” with me, a sleeveless, knee-length, black Ann Taylor dress with a pleat at the back and a demure neckline, which I wore to every single one of these dreadful things. I put on a strand of faux pearls. I think of this as the uniform of fund-raising professionals because it’s classic enough that it could be something really expensive, but plain enough that it doesn’t stand out, so you’re unlikely to upstage or offend any donors, and it works in all four seasons. It’s the vanilla ice cream cone of fund-raising events. Or so I’d thought. I was now melting, in both a physical and an emotional sense, from the following combination of issues: it was August on the Vineyard; I was alone at an event with my boss’s boss; and I was the one who’d selected the food, made the handouts, gone with only beer and wine, and spelled all the names on the name tags. After mopping off my sweaty self with toilet paper and applying as much deodorant and makeup as I deemed logistically possible, I slipped out and stationed myself behind my name-tag table.
A stream of pastel linen began to arrive. The foyer was starting to resemble a Ralph Lauren ad campaign of fit grandparents with yellow sweaters tied around pink-polo-shirted necks alongside a floral Lilly Pulitzer magazine spread with a few stragglers who’d very clearly walked straight off of a golf course. Not a speck of black fabric among them. I stood like an out-of-place beacon behind my table, the youngest person in the room by a good thirty years and the only one in a formal dress and heels, with my hair pulled into an unfortunate, severe bun on account of an inability to cope with frizziness. Ridiculous as I felt, I knew what I was doing. I’d memorized as many faces as possible ahead of time (thank you, google) so that I could greet guests by name, by preferred nickname at that, and hand them their tags while gesturing toward the cater waiter holding a platter of something vaguely shrimplike to my right. I wondered if I could hide behind the name-tag table for the entirety of the event because I dreaded walking into the cluster of billionaires stationed in the circular living room underneath the timber-framed skylight rotunda.
Win jabbed a glass of white wine into my hand and I wondered what I was supposed to do with it. Pretend to drink it? Pour it into a plant? Hold it aloft and try to exude casual wealth? I decided to mete out tiny sips over the two hours of the event in the hopes that this was what a person was supposed to do with a glass of white wine on the Vineyard. I exhaled with relief when the caterer had a question for me. I hurried into the kitchen with her, hoping Win thought I looked industrious and capable, and that I might somehow be able to stay in there for the next hour or so.
As the event drew to a close, and nothing cataclysmic transpired, I wondered why I’d endured so much anxiety over what amounted to a cocktail party with a few remarks. For the first time ever, I questioned what the purpose of my job was. To facilitate social events among really rich people who mostly already knew one another, in the hopes that they might one day write us a check? I was relieved it’d gone smoothly, but I wasn’t sure I felt any sense of personal accomplishment. It was more that I’d done what my boss had asked me to do. I’d executed a straightforward list of tasks. Pressing my back against the donor’s designer wallpaper (who knew that was a thing) just to the right of a Picasso, clutching my empty wineglass now fused to my palm via sweat, I felt a sense of vertigo. I envisioned decades of me doing these events, of gradually inching toward the age of most of our donors, of eventually progressing to Ellen’s level, and then to Win’s, and I wondered what the point was. Would I ever feel like I was doing something meaningful and not just incurring ever-higher levels of anxiety? It’s not like I’d changed anyone’s life or created something lasting or profound. I spent most of my waking hours at my job and after this harrowing fifteen-hour day, which ultimately resulted in nothing concrete I could point to as an achievement, I started to question why.
I was proud of the work NPR and PBS did, and I believed deeply in the mission of WGBH, of bringing unbiased news and information to people. But I was having a hard time seeing my own contributions to that whole. I was a small cog in a mammoth corporate machine and I didn’t feel like my work had an impact that meant anything to the overarching end result. My thank-you letters and my name tags seemed like nothing more than stacks of paper people pushed aside as they reached for the more important things of their lives. I didn’t suffer self-aggrandizement and I knew WGBH would keep on going without me. It’s not like NPR would go off the air without me occupying my development associate cubicle. I wanted so badly to climb that proverbial ladder, but this event had me questioning why, and if I could slog through another few decades of name tags in order to get promoted to a position that would comprise a crucial element of the system. Would I ever derive personal satisfaction from this type of work? From being a worker bee focused on improving someone else’s hive? I’d always pictured myself as part of a team, as someone with a name badge and an identity defined by where I worked, and by what I did. But I was starting to question if that was what I actually wanted to do with my time. I was unfulfilled. I was in turmoil.
Win and I left the donors’ home together in a cab and then caught the ferry back to the mainland. Sitting side by side in the plastic chairs that make up the front row of the boat, facing a window overlooking the darkening sky above the ocean, I sensed an opportunity. Win wasn’t reading or looking at her phone and we’d already debriefed the event during our cab ride. I decided this could be what I mentally termed a “career advancement conversation,” since it was rare I had time alone with the boss of my boss.
Emboldened by that solitary glass of wine on an empty stomach—and while inhaling the almonds I’d packed in my bag since I thought it would be rude to eat canapés during the event—I asked Win something along the lines of, “How do you measure success in your life?” I said the word “life,” I remember very clearly, but I assumed she’d discuss how she measured success in her career. Win exudes confidence and professionalism, and I thought of her and Ellen as my ultimate career destination. What I hoped was that we’d steer this around to discussing how I could advance and find fulfillment in my career.
Win told me she measured her life through her personal successes; through the milestones in her family and their accomplishments. She went on to explain that ultimately, you have to look outside of your job in order to create a well-rounded life. Her reply was the only thing I hadn’t imagined her saying. I’d assumed that everything would come from, and through, my job. College had filled that role, as it’d given me a purpose, a social outlet, volunteer work, the opportunity for accolades, a community—it had constituted my entire life. I’d been trying to engineer my job to serve that same function, and now I had confirmation that it wasn’t ever going to do that. Between Win’s words and my feelings of disappointment after the event, I felt unmoored. This thing I’d held up as my paragon, my ultimate goal—my career—was turning out to be quite a bit less inspiring, exciting, and holistic than I’d imagined.
A few weeks later, as I read over my to-do list one Wednesday morning in my cubicle with Starbucks in hand, I slumped down into my ergonomic office chair, tapping my red patent leather flats against the plastic mat the chair rolled around on. This list could’ve been from six months ago or even a year. I had a ton to do, but I just kept toggling down my list from top to bottom, and then bottom to top, vainly trying to divine some purpose, some meaning from all this interminable busywork that I was supposed to do. My job had evolved into an exercise in repetition. Sure there was variation, but essentially, I did the same things over and over and over again: assist my bosses in asking for donations, thank donors for making donations, steward those donations, then ask those same donors for another donation, and rev up the gristmill all over again. It was an endless loop of development associate déjà vu. I’d had this job for only a year and a half and I had no idea how I’d do it for the next forty.
Worse still, by the time I got home every night I was exhausted and didn’t have the energy to do anything remotely creative or interesting. Most days I went to a yoga class right after work, then Nate and I ate dinner while sitting on our secondhand couch (lacking as we were in a table and chairs), and then it was time for bed. Weekends weren’t much better because they mostly constituted a race to prepare for the next week: grocery shopping, errands, cleaning the house, preparing meals for the week, doing the laundry. When was I supposed to figure out what I was passionate about? When would I do something that mattered? Where was the space in my life to uncover deeper meaning? Did a deeper meaning even exist for uninteresting, real people like me?
I started walking over to the office cafeteria at 10 a.m. every morning to buy a coffee and again at 3 p.m. for a muffin, just for something to do, something to break up what was becoming my monochromatic workday. Nate and I got married that summer and with the wedding behind us, I felt like I had nothing left to look forward to. I had everything I’d wanted, namely a husband and a career, but I didn’t know how I’d maintain this routine and this monotony for the rest of my life.
I was promoted to senior development associate, accompanied by a raise, and decided to start getting my hair cut at a chic salon in Harvard Square that a woman in my office recommended. They massaged my neck, brought me herbal tea, washed my hair, and cut and styled it, for just $120. The fact that I used to eat for an entire month on that same dollar amount didn’t register at the time. I worked hard, so I reasoned I deserved to treat myself. What was the point of this job otherwise? I told Nate he should buy the stereo equipment he wanted, we got Thai takeout every Thursday night, and went out to dinner every Saturday. This lifestyle inflation we slowly layered on didn’t feel like anything noteworthy at the time. After all, we were still way more frugal than everyone else we knew. We didn’t have any debt, we lived in that dungeonlike basement, and we took our lunches to work every day. Nevertheless, our expenses were rising month after month. I’d heard the phrase “lifestyle creep,” but I didn’t think it applied to Nate and me.
The problem was that spending all this money didn’t make me feel any better. It didn’t get me any closer to feeling like I had a purpose. I mean it was nice, but I realized that aside from the basic improvements it provided of living in a safe neighborhood (with an in-unit washer/dryer) and an ability to buy healthy groceries, this extra spending wasn’t increasing my happiness at all. I thought Nate and I needed to aim higher so we decided to buy a house. Or rather, to save up to one day buy a house. That gave us a goal, a long-term joint project that we could discuss and plan for and work on together. Nate and I are at our best when we’re collaborating, and buying a house in one of the most expensive real estate markets in the world was a darn good project.
We started going to open houses every weekend to give our dream some substance. We couldn’t afford a single thing on the market in Cambridge, but the knowledge that our money was going toward something tangible made all the difference. I still got my fancy haircut and we still ordered Thai takeout every week, but we thought twice before going out for drinks or shopping at Whole Foods. When we first moved in together, I’d managed to save $2,000 of my $10,000 AmeriCorps stipend and Nate had $6,000 in the bank. Sharing this crystallized goal of a home had a tremendous impact on our financial behavior. In 2008 alone, we saved $29,100 of our combined take-home salary of $69,730, which gave us a savings rate of forty-two percent. For two twenty-four-year-olds, we were doing pretty well. We made a lot of money for our age and we managed to save a lot of money for our age. In retrospect, we could’ve saved even more, but since we were still unaware of the powers of extreme frugality, this was pretty decent. We were on a mission.
In a weekly staff meeting that fall, I chose a chair on the far side of the conference room so that I could stare out the window overlooking the parking garage, which was a better view than the blank whiteboard on the opposite wall. I always got to meetings early, not because I was keen, but because I wanted to pick my seat. Plus, it was an easy way to brownnose. I was sizing up my colleagues around the table, wondering how they all did it. How they looked so engaged and genuinely interested in what we were discussing. I was pretending to take notes in order to stay awake and, since I have such neat handwriting, I realized anyone could read what I was writing, sitting jammed up next to each other as we were so that everyone could have an equal place at the table and didn’t have to hug the wall in a folding chair. I wrote down every other word Win was saying while thinking about where Nate and I should go to dinner that Saturday.
Then I heard Win say the word “layoff.” I reared my head up and wondered what we were talking about. Why hadn’t I been listening?! She went on to explain that every department was being required by management to lay off a specified, but undisclosed to us, number of people. My body temperature rocketed and my face burned with anxiety. The last time I felt this level of concern in public was when I almost fell off a chair in front of my entire fifth-grade class, boys included, while tacking up my drawing of a leaf to the bulletin board. I was cemented to my swivel chair and clamped my eyes on Win, my pen frozen midword above my notebook. I was afraid to glance around the room, thinking that might implicate me somehow. Don’t guilty people avoid eye contact? Or do they make eye contact?!?
Either way, I decided the best course of action was to remain stationary. I whirred through all of my transgressions: being late on occasion, missing edits in letters, forgetting to sign donor files out of the file room; but most of all, most dangerous and damning of all was the clawing, growing apathy I felt about my job. Was it obvious? Did my bosses know my inner thoughts? Had I let them seep out, unfiltered, in word or in deed? When the meeting ended, everyone filed out silently, like you do at a funeral when it seems boorish to make small talk. I looked at my feet and hid in my cubicle for the rest of the afternoon, gossiping covertly with my colleagues, which was hard to do since our cubicles weren’t offices.
A week later, Nate’s boss made a similar announcement and that night, I stewed in our combination living room/foyer/laundry room while drinking Trader Joe’s imitation prosecco. I shouldn’t have been surprised. It was 2008 and all the news ever talked about was the Great Recession. Until now, it’d seemed like a problem for other people in other places with other jobs. I was grateful Nate and I had set our goal of buying a house because it meant we had a bunch of money saved up. Unlike all these investment bankers we kept hearing about who’d lived paycheck to enormous paycheck, Nate and I could afford to lose our jobs but still eat and pay rent. We calculated we could last at least a year without either of us being employed, and probably longer.
But it wasn’t the money that I was most worried about. It was the shame. How would I walk out of my office with my framed wedding photos and stash of desk snacks in a cardboard printer paper box and admit to everyone that I’d been the one laid off? That I was the worst employee? What would I do? No companies were hiring, and it’s not like I had decades of illustrious experience to fall back on. I called my parents and asked if we could move in with them if job Armageddon happened and they said of course. I’m a worst-case scenario-ist, but also a pragmatic planner. I needed contingencies.
Every time Ellen called me into her office for the next few weeks, I was certain this was it for me. One afternoon I heard her calling my name and I just didn’t move. I could feel sweat in unfortunate places. After a self-indulgent minute of allowing my short career to flash before my eyes, I stood up and, ready to pass out, walked what felt like a perp walk the ten feet to her office.
Turns out, I’d overreacted, as perfectionists are wont to do, and neither Nate nor I got laid off. But it scared us. The idea that our jobs could be pulled out from under us with little warning ushered in a new way of thinking about money. Our parents had raised us with the assumption that jobs are secure, that they provide for you and that if you work hard, you’ll always be fine. It didn’t feel like that was the reality anymore. And it wasn’t. We started to save even more of our take-home pay every month. Just in case.
Back in college, my life changed every semester and I’d thrived on that diversity. Now, I’d been in the same job for three years, we’d been living in the same basement apartment for three years, and I wanted something different. In my infinite wisdom, I decided the solution was to go to graduate school. Since college had been such a complete, wholly satisfying experience for me, I wanted to re-create it, to regress into the comfort of student life. I also saw a master’s degree as a hedge against potential future layoff scenarios since I’d be more senior, with a richer résumé and an MA after my name. I goaded myself on with the promise that it was another thing to achieve, another gold star. Another external accolade I could stash away in my arsenal of empty successes that I assumed would somehow, someday transmute into happiness.
Nate and I liked Cambridge, a lot more than Brooklyn or Kansas, but we craved adventure. We’d been traveling abroad for vacations every year over the Thanksgiving week (because international flights are cheap then), but that wasn’t enough. We wanted to test out living in a new city. Washington, DC, seemed like the best candidate. It had universities where I could go to grad school; it was urban, which was what we were now accustomed to; and Nate’s organization was interested in sending him there to be their Capitol Hill presence. I did some research and learned I could go to grad school for free if I worked full time at a university. Since I had zero intention of going into debt for the first time ever, that sounded perfect. I was getting in the habit of up and moving any time I wanted a change, but it didn’t bother me because I was young and wanted to experiment with living in different places, with different iterations of myself. Nate and I were twenty-six, unencumbered, and unsure of how we wanted to spend the rest of our lives. It was time for us to move on.