Four years ago, when I moved back to Boston with my wife, I started teaching an advertising class at Endicott College (I even got an MBA mostly as it would be a requirement to teach at that level).
Spending time with young people does have a way of keeping you young, at least spiritually. College students have their finger on the pulse of what’s happening and an eagerness to do well and to do good, not yet jaded by the “realities” of the world. And being in the posture of teaching helps me keep my eyes up, looking for ways to bring live industry dynamics into the classroom to expand beyond the traditional academic lesson plans.
I have enjoyed crossing paths with so many students in part because they are usually quite clear on their why. Though they might not know where their careers will take them, they’ve signed up for a class and a major because in some way, it speaks to them. And I may be older but I’m not too old yet to remember why I chose to study marketing and psychology when I was in their seat. I loved the idea that storytelling could be a career. That you could create products and experiences that mattered to people, and by understanding them well, you could build businesses that thrived. In high school, taking a marketing class and helping to run the “school store” during lunch break connected me with some of my favorite people; we had fun, got to travel for class events, and shared in our success and failures together – though we never failed at selling homemade cookies.
We all have a similar memory, regardless of the path your career has taken you. Perhaps you wanted to help save people before you studied medicine and became a nurse, doctor, or researcher. Or you wanted to protect people, so you went into law enforcement or joined the military. Or you wanted to help people find their homes, so you got your real estate license. But somewhere along the way, the pressures of life and the necessary administrative burdens of our jobs have a way of bubbling to the surface, taking up all the oxygen in the room and making us forget why we wanted to do this work in the first place.
This week, I had the privilege of being in Madrid to speak at the Transformational CMO Summit. Ostensibly, my talk was about aligning brand ambition with a modern infrastructure, with typography and design at the center. Predictably, much of the conversation centered on AI, best practices for implementing it across organizations to drive transformation, manage costs, and scale productivity.
And yet, surrounded by accomplished executives I was consistently reminded of the why. Jesse Morris, Head of Marketing at Schneider Electric, sent me a message before the event saying how much he was looking forward to my talk because he had started his career as a graphic designer. Like my colleagues he had learned typesetting on a Letraset machine. Then, during the presentation Dan Barber, Group Chief Communications Officer at OCS, raised his hand and shared that as he prepared for a branding project, he had found an old typography book his grandfather had given him years earlier. Leafing through it was both inspirational to his work and a personal connection to his family.
Marketing and business leaders today are challenged by the same economic, geopolitical, and technological issues as counterparts in all industries. And as a result, in forums like this most of the conversation rightfully centers on how brands can leverage technology like artificial intelligence to grow faster, with more efficiency, staying ahead of whoever their relevant competition may be.
Don’t get me wrong, leaders have difficult mandates, and getting together to wax poetic about brand and creativity may be a tad idealistic – the primary takeaway for leaders was spending time with their peers and capturing ideas on how to better take advantage of emerging technology. And yet, throughout the two days, even though I am not a designer myself, many folks came up to me to express how design and creativity is what kickstarted their careers.
You may have heard the mantra: “we overestimate what we can accomplish in a day, and underestimate what we can accomplish in a year.” It’s quite true, and as a result it is a useful exercise when feeling stuck or in a rut to look back five years. What is different about your role or your life? It will shock you how far you have come, whether at a job or in a relationship or with a particular hobby or talent. By the time we’ve reached a particular place in our careers, it’s easy to forget the moments of serendipity that led there. Very few people end up on the path they thought they would be on when they started out. For those who do, I can’t decide if doing so is a blessing or a curse. Part of the fun of a career is never knowing where it will take you. And I’ve certainly found myself in some surprising places, with some surprising people, as the result of a happy accident - working in the field of design. My current role is very engaged in relationship-building, and I’m traveling frequently to speak at or host events. I don’t think of myself as particularly engaging in this effort, but colleagues are kind enough to tell me I am. If this is true, it must be attributed to the 15 years of comedy I’ve performed and studied in Boston, New York, and Los Angeles. As I like to joke, “I’m a failed comedian, which makes me an excellent MC.” As Steve Martin once said, “you’ll use everything you’ve ever learned.” And it’s likely that wherever you find yourself now, even if you’re not consciously aware of it, the way you got there and how you approach the position is likely driven in some part by your original “why.”
As I’ve gotten older, I’ve determined that the people who do it best are the ones who – in the face of the very real challenges of work and life – are able to magically retain the optimism, curiosity, and passion that pushed them toward their career in the first place.
This is, undoubtedly, one of those “easier said than done” tasks. And I know it’s not something I’ve always been able to do myself. Maybe we all need a small reminder to push our heads above the noise in our respective markets and recall a time when we dreamed of the ability to tell stories for a living, or to help people, or to open a business, or to travel, on and on. Those small reminders matter, and I got one this week in Madrid.

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