What I Learned From A Boss Who Was The Best Teacher I Ever Had
I did it. I made it.
I was barely 26 years old and after graduating into a recession, working peripherally in my industry for four long, hard years as I struggled to even write for free, I was finally, finally a full-time writer. A copywriter, to be precise, for a tiny but mighty family-owned ad agency in the middle of a small village on Long Island, New York.
It was a time of flux at the agency. The creative director who had just hired me the week before was gone in the poof of the chemical reaction you get when you mix a hot temper and a few too many cold drinks. Succession was unclear; there were two art directors, one of which was a tall, athletic, handsome guy with a charming smile who wouldn’t look out of place in an Abercrombie catalog, and another equally tall but heavyset man whose small patch of ringlet curls and wide-eyed focus reminded me of Will Ferrell’s Zoolander character, Mr. Mugatu. He had a booming voice but in the pitch of Seth Rogan’s, a laugh that erupted like it surprised him, and an earnestness that belied his gleeful penchant for minor mischief.
But more than that, he was mad-scientist brilliant.
"His name was Bryan Hynes and he was a visionary with visuals, whole-picture thinking, multichannel-campaign strategizing, and subliminal design, where every pixel and carefully selected word conveyed more nuance and emotion than the sum of the parts."
His name was Bryan Hynes and he was a visionary with visuals, whole-picture thinking, multichannel-campaign strategizing, and subliminal design, where every pixel and carefully selected word conveyed more nuance and emotion than the sum of the parts. But more importantly, as he was appointed the department head, he was a man of the people always.
He called us — himself included — a merry band of misfit toys. Roughly 90% of us were career infants, our professional development arrested and, for many of us who had graduated into a recession, stagnant for years before we were able to finally get back into the game under his leadership. A lot of us were just like me — struggling in related or not-so-related fields for years as we tried to pay off student loans in a creative industry that just wasn’t hiring. We were all, in his eyes, a little broken … but not irredeemable. Not unfixable. Just a little behind.
He himself was a New York City exile, banished to the commuter ’burbs in the family way, and with a tough home life situation that made a chaotic office of untried green youth a refuge. He had a few other things that made him consider himself “broken,” but he taught us down-and-out 20-somethings how to have grace about things like that. He approached his perceived flaws with humor and acceptance without complacency.
He was open about his ADHD, and his use of medication and therapy to manage it, taking the stigma out of what’s categorized as a mental disorder. He acknowledged it and how it impacted his work/life balance and how it made his creative process unique. Then, he encouraged us to also plumb into our differences to find what makes our thinking special.
In this, he made me a better writer. He challenged me to go beyond what was natural and easy, to explore styles that were not my own. He taught me to craft and win pitches and contracts. He forced me to learn about new technologies, and pushed me out of my comfort zone in ways that would bolster my creativity, from introducing me to evolving music to new social apps and media channels.
Also, through his vulnerability in a male-led agency, and at odds with ownership, he rejected the concept of leadership by fear. Instead, he led with compassion and by example — and inspired loyalty through it. No one in his team was in the trenches deeper nor longer than he was. When we were up against a deadline for a campaign pitch, a catalog launch, or an RFP response, he was the last one out the door in the wee hours. His hard-and-fast rule was to never ask of his staff anything he himself wouldn’t do. There was no task in which he was above; rather, he did much of the least forgiving grunt work himself, hacking away in the thickest of weeds, to allow rawer talent to shine.
"After three years of fruitlessly hoping, asking, then begging for a raise, I received a job offer that would change my life. It was client-side, a cushier gig than the high-stakes game of per-project survival played by ad/marketing agencies and professional freelancers."
And so from this, I learned from him how to manage, with kindness and confidence. An open mind and encouragement. But most importantly, with an eye for potential — for what could be and not what was.
Experience and a highly decorated résumé was not as important to him as passion and a thirst for the craft of creation. As a man in his early 40s managing a flock of mid-20s at the time, taking graphic designers, copywriters, project managers, and production artists under his gargantuan wing, he was most focused on giving his ducklings the courage to fly.
It was perhaps this that hurt the most as the hardest lesson I ever had to learn from him.
After three years of fruitlessly hoping, asking, then begging for a raise, I received a job offer that would change my life. It was client-side, a cushier gig than the high-stakes game of per-project survival played by ad/marketing agencies and professional freelancers. It was in travel, a dream industry that needs no further introduction.
When I handed Bryan my lengthy, heartfelt letter of resignation, I immediately sat down on the little orange stool I had spent years sitting on as he coached me through copyedits, creative strategy, then as time went on, grief, loss, natural disaster, relationship collapse, and more. I sat down and I cried as he read it, feeling like the end of an era, because three years at one job is a long time for an Xennial and a lifetime for a 29-year-old. I teared up hoping that he would ask me to stay and knowing that he wouldn’t.
He didn’t. He told me it was time and the opportunity was right. That I outgrew his island of misfit toys, and that he was proud of that.
He told me the same when I asked him why he never tried to hire me again when he reassembled most of the team in his next role, after the agency we worked at together folded due to nepotistic mismanagement. I was hurt that he didn’t want me back, but he said ever so gently, “I have nothing more to teach you; you need to live a big life, bigger than what I can give you.”
I have now been friends with him for nearly triple the time I worked for him. He’s watched my life grow bigger since … just as he wanted. Just as he set me up for as my teacher. My mentor. My treasured friend.
This post is part of a series honoring beloved teachers who make a difference with their kindness, love, and wisdom each day. Thank you to all of our educators from all of us at CircleAround.com. To read other stories in this series, please click here.