My Biggest Lesson: Stephanie Caruso on 'Bridging the Gap'

A maker by nature, insightful, agile, inclusive, and collaborative, Stephanie Caruso, VP, group creative director, Jack Morton, is an eternal student. She consumes massive amounts of content - from pop culture and TV, to fine art and podcasts. 

LBB> Is there one event / piece of wisdom from your career that's always stayed with you? What is it? 

Stephanie> My best advice? Bridge the gap.

In 2014, Ira Glass wrote a brilliant piece called The Gap that validated the first decade of my career. 

“All of us who do creative work, we get into it because we have good taste. But there is this gap. For the first couple years you make stuff, it’s just not that good. It’s trying to be good, it has potential, but it’s not. But your taste, the thing that got you into the game, is still killer. And your taste is why your work disappoints you. A lot of people never get past this phase, they quit…. We all go through this. And if you are just starting out or you are still in this phase, you gotta know its normal and the most important thing you can do is do a lot of work.” — Ira Glass

LBB> Set the scene! How old were you when you learned this insight, where were you working, how long had you been there, what year was it, what was your role and how were you feeling generally about your career at this point?

Stephanie> I guess you could say this insight was drilled into my head at the impressionable age of four when The Karate Kid came out in 1984. I had three teenage siblings at the time who were obsessed with the summer blockbuster, and it was a household staple. The message was clear - –you need to paint the fence before you can kick Johnny’s ass. 

An idea that would be reinforced throughout my life by my family and teachers, especially my mom. 

4-year-old Stephanie 

LBB> Tell us about the chain of events that led to you learning this insight… be as specific as you can!

Stephanie> In 2002, I was living in Boston and had landed my first agency job. I would call my mom often with life updates, and any hint of complaining about my job she would tell me to be grateful for the work and do whatever they asked of me – that it was an opportunity. So that’s what I did.

I was at a small IPG agency called Marketing Drive where I worked as a designer in a studio making barcodes for Gillette mailers and did tedious file preparation for printing. I made complicated clipping masks, retouched images, formatted PowerPoints, resized banner ads. The traffic manager would drop off a pile of work orders on my desk in the morning and I’d stay well after everyone else had left till they were done. I didn’t always know what I was doing, but I always figured it out. I did all the stuff other people didn’t want to do, and I asked a ton of questions to the people I thought already “had it all figured out”. 

I was part of a real creative team. I worked in the Park Plaza building in Boston. It looked like the Flatiron in NYC, we had a cool doorman that played the trumpet at Wally’s Cafe and the Cantab Lounge, we got free lunch sometimes and I was living my dream of getting paid to make “art”.

My hard work in the studio got me noticed by our CD, who discovered that maybe I wasn’t going to be a designer after all. I was conceptual and funny, and I could even write a line or two. I had a point of view that sparked ideas with other creatives in brainstorms and resonated with clients. I remember one of my first headlines that got published was “Get into a relationship where you won’t get hurt”. It was for a new running shoe line from New Balance geared towards female runners, and the print ad got a placement in People magazine! In my mind, I had totally made it. But I didn’t stop there.

I took on more work using different skill sets – I had painted the fence long enough and now I’d moved on to waxing the cars. If you didn’t understand that last line do yourself a favour and watch The Karate Kid. Today.

LBB> And if you got some words on wisdom from a particular person or there’s a key, influential person in this story – tell us about them! What was your relationship to them, what were they like, how did you feel about them (admiration, awe, respect… disrespect)…

Stephanie> My mom is a total force. Her work ethic is 100% the reason I work the way I do.   

LBB> Why do you think it struck such a chord? 

Stephanie> Working hard always resonated with me – you could measure your personal growth. 

I started with tangible skills like learning all the keyboard shortcuts for the Adobe suite. Conceptual success is more subjective to measure, but it came in the form of good client meetings and the respect of my CDs and peers I admired.

LBB> How did it change you as a person and in your career? 

Stephanie> I don’t take my career for granted because my success is a result of two decades worth of hard work. 

LBB> And as you’ve progressed in your career, how have you re-evaluated this piece of advice? 

Stephanie> We work in an industry that is always evolving, so you need to be prepared to always put in the work. Really knowing the fundamentals makes taking on new challenges a lot easier, but it’s a job that once you stop being hungry you should probably walk away.

That said, I don’t say yes to every opportunity that crosses my path now and I try and focus on ones that will help me achieve my more evolved goals as a leader and not just as a creative.

LBB> Is this insight or piece of advice something you now share with other – if so, how do they respond to it?

Stephanie> I share this advice a lot with people on my team struggling with their level or development. Everybody wants to start working on the big campaigns right away with a director title. If you really put in the work, you’ll be truly prepared when those briefs pop in your inbox and you’re running a team of your own.

Taking the time to learn your craft not only improves your work, but it also gives you empathy to lead and manage a team that you can relate to on multiple levels. You understand their role because you’ve been there.