Your Most Challenging Client: You

Self Reinvention Requires Objectivity, Using Your Super Powers For You

“The Cobbler’s Kids Have No Shoes”

Chances are, you’ve heard some iteration of this phrase if you’ve ever worked for a company where you had to spend your professional time dedicated to an internal project. “The Cobbler’s Kids” is corporate shorthand and derived from some variation of an original saying that went something like “the shoemaker’s children go barefoot.” The universal translation implies that the shoemaker is so busy making shoes for paying customers that when it comes to their own family—needs get overlooked.

The first time I had both heard and lived a version of this, I was a Creative Director for one of the world’s first and long-defunct digital agencies, Agency.com. The opportunity to get involved with one of several versions of our own business Website was too good to pass up, so when I had a chance to lead one of the teams—I jumped at it.

Naivety has its advantages.

In the end, we got a version of our Website launched, which lived for a while both in the public domain and in my portfolio, but it took months of learning just how difficult it was to muster resources and, even more importantly—objectivity. And in retrospect, how I now miss the resources I had… a motivated and talented team who would put in evenings and weekends and leadership that made it a point of pride that our office was leading the internal charge that would benefit the agency more broadly. It’s difficult enough when the company you work for becomes your client (especially when your business is servicing paying clients). Still, it takes on an even more daunting challenge when the client is actually you, yourself—the individual.

Since my Covid-disrupted career transition began nearly a year ago, I’ve been chipping away at client me—and I’ve come to realize that I am probably the most challenging client I have ever had in my career thus far. A recent meeting with a well experienced recruiter put a fine point to it:

“You have to do what you’ve been doing for your clients, for yourself now—and that’s not easy.”

Wow, was this the understatement of the pandemic. Clients pay me to be a strategist, creative problem solver, marketer, team leader, etc. I come in with an instant advantage—a degree of experience, a willingness to ramp up quickly on their business, and most importantly—the ability to remain objective. There is simply no way to remain objective when the client is YOU—it’s pretty much impossible. So you rely on others, those you’ve worked with, those you’ve never worked with, and you pay extra attention when others are talking about you.

They are objective when it comes to the brand of you—you are not.

The Golden Rule of Reinvention: Lean Into Your Superpower(s)
People will tell you what your superpowers are, but they won’t always articulate it eloquently. I’ve gotten validation on my ability to synthesize complex information so it’s something you can take action toward vs. analysis paralysis. As I was thinking about my own personal challenges in career reinvention—I realized that I have a problem to solve. My experiences have been both broad and deep, but varied.

I’ve been a designer, a UX lead, a Creative Director, a Managing Director, a chief strategist, which can be almost anything—most prospective employers want to know pretty much where they are going to place you and in which department. They write job descriptions that, at least on paper are designed to fit into their org even if they need skills which transcend organizational silos. So, I decided to do what I do for others. I simplified my varied career narrative into a single visual, focusing on the three things that I do best and have the most depth in (below):

My intent here is to distill the three things that I am really good at. There’s a magical element to the “rule of threes”—something that helps our brains more easily wrap our heads around and retain information. Instead of looking at my breadth of experience as a challenge for an organization, it’s positioned as what it is—brand, communications, and the digital experiences that underpin them are more intertwined than ever. Organizations need translators and silo navigators who can help connect, integrate and align touchpoints. Synthesis and simplicity are superpowers for me, so I have to use them for myself, not just others.

I’m still learning. Life is, if nothing else, a teacher that we choose to learn from or tune out as we advance our years on this planet. I’ve worked with challenging clients before, and even if I am the most challenging—I know I can deliver for myself as I’ve done for others.

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I write about the business of building brands and life—by design.