Why I Left Advertising, Part Two
Seasons Come, Seasons Go
The goal for me in exploring the varied seasons of my career is not to regale you with the tales of some illustrious advertising wünderkind (which I certainly never was) but rather to try and discern some themes that developed through them that led me as inextricably into the industry as out of it.
While I typically have a sunny disposition, I carried all the seasons – the sunny ones and the dark ones – into my work every day because I’ve only ever known how to be just one thing: exactly how I am at any given moment. Just ask my wife how well I can keep a secret. Sure, I hid not a few tears in the stairwell and an angry determination to simply walk in the door some mornings, but one question or probe into my welfare would have revealed just about everything going on behind my eyes (and even so, I’m still surprisingly good at poker).
My point is, I wasn’t able to compartmentalize work and life the way some people seem to do so well, and my personal matters just took up real estate in my 64 square foot cubicle, occupying no more space than my desktop menagerie of oddities when life was easy while other times really making the whole area feel pretty darn cramped with its long shadows and piss-poor attitude. My inner state and my life at work were one and the same, and while it makes me a genuine person, I sometimes wished it were easier just to tune my inner life out, put my head down, and do my job.
But throughout these seasons, I have discovered in hindsight these themes that revealed themselves, one graduating into the next in chronological order as I matured:
1. Learning the Discipline of Work
2. Believing in My Talent
3. Discovering my Agency
It was at long last when I discovered my agency (that is, my own ability to advocate and contend for myself) that I finally let my mind ask some questions I’d hidden for a long time and listen to my heart answer them honestly.
Season One:
Wide-Eyed Delight & Hapless Ignorance
The first season of my career was a paradox I’m sure none of us as beginners has ever experienced: being both starkly unprepared for and unsure of your very place in life itself and yet delighted and open to whatever it turned out to be. Things didn’t get delightful, however, until after I signed my first salaried contract. Before that was mostly just the chaos of becoming an adult.
I never was one of those people who knew what they wanted to do after college (or in college, or when I grew up). Ironically, I was a double major in two extremely challenging degree programs – a BA in Creative Advertising and a BFA in Theatre – in which I was literally surrounded by people who all seemed to know exactly what they wanted to do with their lives. I loved acting but couldn’t see myself in New York or starting a theatre company in Chicago like those in my cohort, and I loved being creative, but didn’t share the same passion for the One Show and would glaze over when someone pined longingly for an opening spot at Ogilvy or Crispin or wherever else. It all just didn’t interest me.
After graduating, I’ll never forget the feeling that the only thing I learned in school was who I didn’t want to be. But who did I want to be? I knew my future self was a creative sort of fellow, a maker, an artist, a writer…a something I couldn’t quite make out. Well, I didn’t know because I hadn’t met him yet. While that future me seemed to squiggle in the distance, what was loud and clear were my comparison-based insecurities.
This revelation of learning who I didn’t want to be had the opposite effect on me. It didn’t free me from the expectations of others, but rather, lacking a clear picture of what to strive for, I internalized a staggering self-doubt and tried hard to imagine myself into the passions of others. When that didn’t work, I simply berated myself into a haze of indecision for not being passionate or talented enough, and for a year or two floated by in a job with the art school I graduated from.
It seemed to me that not getting to do whatever you want in life was a first-world problem if there ever was one, so I put all my dreaming aside and focused on getting a ‘real’ job. When it came down to it, I had student loans and an advertising degree, so I figured I’d jump in and get a job doing that. While my BA in Advertising was in Copywriting specifically, I decided I wanted to be an Art Director instead, so armed with a decent book of my odds and ends from school and my art school job, I was amazed when my first Creative Director offered me not only a position but a salary with a round number attached to it.
I entered the advertising world as an exceedingly green Art Director in a big building downtown. Cue: my delight.
I was enraptured by my commute (on a train!) and the view (24th floor!) and our clients (they sold national things!). Working with good friends from college, I started to have a great time, and it felt so nice to put my creative muscles to work again. Maybe I did want a career with this whole advertising thing?
Paradoxically I was also absolutely under water. I didn’t know how to do anything, it seemed. Turns out, a degree in Art Direction would have prepared me for my job better than one in Copywriting. Go figure.
How do you make a banner ad? How do you work with Flash (RIP)? Am I front-end or back-end? I didn’t even know any keyboard shortcuts other than ‘Copy’ and ‘Save’. I lost a few hours in Adobe Illustrator once when I accidentally hit the key command for ‘Outline Mode’ and couldn’t begin to understand how to change it back. I was hamstrung by my lack of experience, and limped by the first few months.
It was so unlike school, it jarred me: real money was on the line, and yet it seemed like the whole thing was just a 100mph production of half-baked concepts dressed up with decent copy and passable design acumen.
Thankfully, I did work around some talented folks with experience whose ability to produce quality concepts and quality design in breathtaking speed fascinated me. It wasn’t necessarily that they were the most creative ideas but that they were well-crafted and fast, and while I might have a brilliant idea buried in my mind somewhere, my ability to commit it to paper and then to the computer and then to a client felt like a kindergartener imprisoned with finger paints when he was dreaming of a Renaissance masterpiece.
I realized that advertising demanded something more than just raw talent or even the tenacious desire to work hard, both of which I had in deep amounts: it demanded an industry-proficiency and even efficiency in which both I was but an amateur.
It was clear: I had a lot to learn, and, suddenly, a desire to learn it. I didn’t think much about doing something else with my life in those days; I was just too busy growing in the present. Future me could wait.
Season Two:
Self-Deprecation & The Long Road of Learning
Awash as I was in my new found career, my focus during this season was on what was right in front of me, and what seemed to stare me in the face day after day was the fact that I didn’t know what I was doing. I had to get better.
I figured, you don’t know what you don’t know, and so I started learning. Most critically, I needed the proper ‘hand-skills’ of the day: Keyboard shortcuts, workflow philosophies, iterative procedures, even ways to use layer styles and other CPU-generated graphic elements that were anathema in school but almost a necessity of time in the industry. I absorbed tutorials and mimicked the look of things I liked until I could produce them genuinely myself.
My process had to be stripped back from expecting the level of finish in my mind to producing ideas one step above “good-enough” for client buy-in and then hopefully having time on the back end to really polish them up before the deadline. And yet, it was really tough for me to see my ideas turn into anything resembling the concept I could see in my head, even if I should work all night. Once I even stayed the weekend and slept in my cubicle for a turkey-themed Thanksgiving Facebook app design concept that maybe looked to me 60% of the way. I would get tunnel-vision and, as many forthcoming annual reviews would tell me again and again, miss the forest for the trees and pour everything in to one amazing-looking portion of a design to the neglect of the whole thing.
With all my learning, I was getting better at my job, though I couldn’t see it so well at the time. Before, I’d I’d limp into most meetings with one decent idea and a few wonky stragglers that I had to introduce with, “Okay, so what I was going for here was…” but soon I was bringing two or three solid concepts I was more able to design and defend. I even came around on a website concept for a well-heeled client who loved my layout above those of my seniors, and I got the project. Glad as I was, I still suffered from severe “imposter syndrome” and had trouble feeling like I was talented enough to stick around.
It wasn’t only that I didn’t believe in myself—that much is clear—but I had let my old sense of comparison from my college days linger on and deflate me entirely. I’d survey all the abilities my coworkers seemed to have and belittle those that I possessed. ‘Pretty good’ was as much as I dared believe about myself, for all I could see were the many ways in which my skills were in deficit and my ideas shoddy. So, I’d decided, I deserved to remain at my level of Art Director, always be agreeable, to never ask for anything—especially a raise (I didn’t deserve one!)—and to be content with what others freely offered me.
However, before I could learn to advocate for myself, I needed to learn to believe in myself.
Season Three
Cynical Despair & Nearly Getting Canned (Thrice!)
I include this season, well, because it happened, but also to highlight the value of mental health. I lived it and came out on the other side, and if you’re in a low yourself right now, please reach out to someone, even me. You’re not alone.
The winds of my life had shifted, and I began to succumb to an interior life which had slowly but surely descended to the point where I felt simply burned alive every day by anxiety and depression, the specifics of which I’ll save for a discussion over a beer sometime. This was, while not the lowest point in my life (I’m looking at you, 23!), certainly the lowest in my career, and the darkness led me to the work crisis I soon found myself in.
Ironically, things fell apart during what should have been a high point in my career. I had just gotten my first raise (which I hadn’t asked for) after I had come up with a truly fabulous idea with my creative director which guaranteed a bright future with a new local client. It was shooting through the agency and ended up bagging us lots of awards and accolades, as well as the brief admiration of our city. I got to work on its foundational campaigns, including new perks like photo shoots, nontraditional signage, first dibs on website concepts, and more – a real home run, and I’m proud to say I was a part of it.
I, however, didn’t try to claim credit for it or let it improve my self-perception for a reason that went deeper than just sheer humility – it was that latent thesis from my college years that had bubbled up into my subconscious again: I don’t want to do this. I kept it under lock and key but it started to be baseline hum that would follow me around.
Numbly, I watched everything bloom around me while stuck fast in a growing shadow.
This was also during the Bangladesh factory collapse, the Boston Bombing and the Syrian war, and my new cubicle, which was placed rather alone next to a TV flipped to the news on silent all day, afforded me a compulsory front row seat to the barrel bombs and devastation.
By contrast, I was also in the thick of a campaign for a big tech client to try and repackage an unpopular product as some kind of whole lifestyle upgrade in the hopes of pushing surplus. What a perfect dichotomy, I thought, compared to suffering world just beyond the window, what a perfect reason to hate what I’m doing.
So, my work began to suffer - severely. I stopped trying, I wasn’t present, and I simply had a tough time walking in the doors most mornings. My internal life took up most of the space in my cubicle in those days.
Just quitting my job didn’t seem right, so I really had to come to some conclusions so I didn’t lose my mind: why was advertising allowed to exist in the world, why did this work matter, and why should I keep doing it?
Now picture me sitting in front of my two creative directors who had just given me a raise after career-advancing work, wondering what in the world was wrong with me. How could I explain to them that everything was burning around me, that I wasn’t sure any of us deserved to have jobs, that the whole industry we were in seemed like a giant, evil lie driving mindless consumerism and distraction from the reality of human suffering going on all around us? Instead, when they asked me what was wrong, I mumbled, “I’m sorry. I’m not sure.”
Needless to say, I nearly got dismissed. While in this probationary period, it was my dad whose wisdom made a difference. After laying out my grievances, he simply asked me, “Yes, but are you really there when you’re there?”
Of course, the answer was no. No, I was not there. No, I wasn’t really trying. Not at all.
But before just putting my head down and working, I had to reconcile with advertising. For a start, I came to realize that the comparison between an ad campaign and chemical warfare was unfair, immature, and too easy. I could stack anything up against suffering like that and it would lose every time. But to what end? What could I do about it?
It’s an unanswerable question which casts doubt on literally everything–how did anything at all justify spending your brief amount of time on it? As Elaine in an episode of Seinfeld says when the gang is discussing death and how not to waste their lives: “Can’t I grab a cup of coffee with friends? Is this wasting my life?” I could interrogate anything into meaninglessness if I tried.
So I came to two important conclusions:
Advertising is not evil (most of the time). It is a (potentially) wonderful, daring and creative agent of capitalism which is a democratization of wealth by which common folks around the world earn money to put bread on the table. That fact alone helped me walk into work every day.
I knew for certain in my heart of hearts that I didn’t love advertising. I still hadn’t given myself permission to ask what I did love to do but I could finally accept that one fact.
With these things settled in my mind, I resolved to truly be present when I came to work each day, and to my surprise and delight, on the other side of this discipline I found enjoyment in my work again.
My efforts were noticed and my job was saved, but it was a close shave. There were two other times I nearly got canned in unrelated circumstances (and if you’re someone who thought about laying me off, thank you for not doing that), but it bears mentioning that my nearness to losing my job wasn’t terribly surprising, as layoffs are nothing special in advertising, as we all know. If you lose a client or go through a merger or, I don’t know, endure a global pandemic, there are bound to be layoffs; the Angel of the Pink Slip lingers thickly some weeks or even months. But my brushes with losing my job were all my fault.
Once in my earlier career, when I was floundering in the midst of knowing nothing, I resolved to get better by learning. Unbeknownst to me, my boss at the time was just thinking of cutting me off as dead weight. Then, some months later, after I’d improved my work, he stopped by my cubicle randomly and said, “Glenn – you used to suck and I nearly fired you, but then you got better. Good job.” His honesty truly was refreshing, and his words haven’t ever left my mind.
The other time was later on, when I had become distracted and lazy in my career. Less humorous was this occasion, and I once again had to learn discipline and focus to keep my job.
As to the absolute wildfire of personal anxiety I was lost in, it would still be some years yet before I let myself get some help, and in the end Jesus and therapy would get me through.
Season Four
A New Passion is Born & Finally Asking for a Raise
My first thematic lesson was learned: the discipline of work. Sure, I’ve always been a very hard worker, dedicated to going above and beyond often to the point of needing to be dragged off of projects just so they could be done. Yet, the big difference is that discipline will prevail when motivation is gone, as I learned through a very difficult time in my life. That dark season taught me other lessons as well, but learning first hand that joy could live on the other side of a commitment to work gave me a new ability to finally learn my next lesson: to value my talent.
My new resolve renewed my zeal for working again, though my subconscious restlessness with what I was doing with my life simmered below the surface. It was enough in this new season that I loved these people and this company, and I decided I could do my best for them by showing up each day and learning what this time of staying put had for me.
I knew it wouldn’t be forever, but for the moment it was where I was. It is valuable and right to be faithful where you are sometimes.
During the forthcoming time I went on to create some of my best work and I found a team within the agency that I would happily reside with until my exit from the company some years later. This team taught me to see myself better.
The volume and quality of work we were collectively producing at times seemed vast and even insurmountable, but such a challenge was just the proving ground I needed. I became nimble, quick, and reliable, able to handle longer lists of projects and capable of the kind of productivity and polish I had so admired when I was a beginner. My ability and my self-perception finally were beginning to meet one another.
It wasn’t the awards that I or my team earned, or the praise of our agency’s CEO or any other external appraisal that made the difference for me–though some specific words of encouragement I still recall warmly–but rather the camaraderie, positivity, and shared commitment to making excellent work. As I esteemed my teammates’ contributions to our work, I began to esteem my own. As I saw the value and quality of work that our collective efforts produced, I began to value my own ability within that. I could look back and see all that I had learned in previous years to get to where I was, and I could also notice what strengths I brought to bear and what vision I had to offer. This clarity was invigorating!
With this belief in my talent came a sudden valuation of myself holistically, and suddenly I realized that what I wanted and what I knew of myself could functionally matter to me. This meant I could finally accept the objective differences between myself and my coworkers. Before, in my more fragile youth, I was only able to bear comparison with another in the negative – either trying to discount or demean their passion or talent so I could feel “off the hook” for not sharing their ability, or, as we’ve already seen, berate myself for not being talented in that same way. At last, I could freely admire another’s passion and talent with objectivity and joy, and weigh the differences I saw within myself without judgement.
I didn’t care for illustration while my contemporary was enamored with it; I wasn’t great at hand-lettering while another was just stellar at it. A creative director would pine often about art direction when they were off work, giving themselves extra projects to practice an idea, just for fun. Whereas before, that would have been an invitation to belittle myself for not doing or even wanting the same, I instead thought to myself, what is that thing for me, which draws my imagination and passion outward?
Enter woodworking.
It all started over a Christmas week off. I had a pile of old shiplap my dad and I had found rummaging through a favorite reclaimed-stuff-from-old-houses store (yes, I do have a favorite one of those). At this point, I only had a few trysts with the shop life in college, briefly working in the scene shop as part of my theatre major and even doing a small stint as a technical director of a theatre summer camp (where I spent the whole time building one furniture set piece instead of teaching my little techies what to do), but I had never really built anything substantial or lasting.
So, I had decided to build a dining table with those pieces of shiplap, and the amount of thoughts and ideas that started to come to me about it were staggering. I filled a notebook with configurations of the wood (did I want them staggered or even, horizontal or vertical or even angled?). I considered for hours as to different leg styles, table aprons, wood joints and more. I photoshopped different ideas with real textures and tried to model it in 3D, just to see it. I didn’t know it yet, but this is what it was like to be obsessed with something.
In my parents garage with a rented miter saw, I feverishly spent the entire week building that table, maybe 8 or more hours a day. In a state of flow which I had never before experienced and with no less than 10 trips to Home Depot, I iterated ideas and built with my hands, talked my parents’ ears off about my discoveries, problem-solved and trusted my gut, cut wood and glued and screwed and puttied and brushed until I finished my first ever piece of furniture, fully conceived of and built by me. It was beautiful to my eyes.
Not with a little sadness, I returned to work the next week and couldn’t stop thinking about the table, and while it wasn’t overnight that I decided to leave my job and change my life with a dramatic vow in a moment of clarity, that week in the garage had changed me.
Two lessons down, one to go: finding my own agency.
What began this final lesson was working up the courage to ask for a raise for the first time. It wasn’t wrong to value myself and I finally knew what I was worth and what quality of work I offered to our agency, and it was a liberating and shockingly un-scary conversation I had with my creative director who honored my request with a “yes”. After their answer, I couldn’t help but wonder what I hadn’t done that years ago.
I was about to enter my final season in advertising, and for the first time in long time, I knew what I wanted and could actually ask for it.
Season Five
Seniority & Saying Goodbyes
My final season saw the most confident, mature, and seasoned Ryan-as-designer that I’d certainly ever met. It was amazing to learn the difference between arrogance and confidence, cowardice and patience, arguing and advocating, distraction and diligence. With these distinctions clear in my mind, suddenly I realized I wasn’t long for the advertising world and I had permission from myself to pursue what I wanted. My inexplicable penchant for woodworking had started to blossom and soon that one-week distraction truly was becoming a passion that I could build a future on (not a hobby—big difference).
What I initially loved about woodworking was simply that I got to see my ideas through to completion, in physical actuality. After a career of pushing pixels so long with very little payoff as to the final product other than awards and acclaim, I was hungry to actually expend my labor and get to hold the finished result in my own two hands. It was a nice break from the digital world I lived and breathed in to smell the sawdust in the air, feel the grain against my fingertips, wipe the glue from my wearied hands.
I soon saw, however, that I could apply my design acumen to my furniture. Sure, anyone could build this or that in their spare time in a garage but my passion went deeper. I was good at this, and I could really make something of my talents here! I had instincts about wood, balance, tension, and materiality that I didn’t even know existed before, and yet here they were, bustling and crowding behind a door I had just discovered within myself.
But if my career had taught me anything, it was to look objectively at my skills and take an honest assessment of where I was lacking. Once again, I had a lot to learn.
Putting my passion for woodworking aside, it wasn’t yet time to leave a good career in advertising, however. Or maybe it was, and I was too scared. Regardless, the first step in figuring out the rest of my life was to leave the nest where everything started, so it was with a full heart and no regrets that I resigned from the agency where my career began.
I accepted a Senior Art Director position with a much different agency than the one I left. I had worked in consumer advertising and now was in the business-to-business world; not to mention, my previous agency had satellite offices in multiple continents and hundreds of employees, and now my whole company was less than half the size of my last client team. This company felt truly like a family–a raucous, extremely hard-working, well-earning, good-time-having family. Trust, personal value, and generosity were paramount to every decision the leadership made, and their desire to take every teammates’ needs into consideration was astounding. What a joy and challenge it was to work there!
It was my intention to stay longer, but global events pushed the timeline on that decision sooner than expected. Circa January 2020, one of my company’s owners wisely foresaw the coming tsunami of the global pandemic and we transitioned to working from home right away, though at the time I for one thought he was being a little overly cautionary. Well, that I was obviously wrong is quite the understatement, as we all know how we soon found our collective selves hunkered down at home as the world endured wave upon wave of everything the last two years have been. Some months later and just shy of my two year anniversary with the company, the owners had to make the gut-wrenching choice to let me go—a decision I will always and forever respect them for. It was unexpected, that much is true, but I also found myself suddenly leaving my second nest, and this time it wasn’t my decision.
It would not have been difficult to find new work in advertising, but I couldn’t help but feel that it was time, whether I was ready or not, to learn to fly. I had truly been given a chance that was, in its own way, a gift. Every season of my career had led me to that crossroads, and on the first morning of unemployment as I took a long aimless walk in the unseasonably crisp air, the freedom and confidence I felt within me was electric. I could stay safe and find another nest or I could really take a chance and see where my passion could take me.
So, gathering my agency about me with a firm belief in my talent and a fervent desire to put my hands to work, I leapt.