Is That What My Aspirations Look Like?

When a friend knows you need (life) glasses before you do

It’s the end of another busy dinner service, and Chef Shawn emerges from behind the kitchen doors to chat with customers. When he stops by our table, we compliment him on the food and ask how he started the restaurant. But he’s in a giddy mood and doesn’t linger on the origin story, soon talking about bidding farewell to the industry to pursue his bucket list.

Chef Shawn leans in, as if to tell a secret. “I’m gonna do all the things in that movie—you know, the one that takes place in Vegas? The one with the tiger?”

“The Hangover?” I ask, eyebrows raised. Didn’t see that one coming.

“Yes, that’s the one!”

When he later learns I’m from California, he says gleefully, “I’m also gonna go out West to become a software engineer. At Facebook.”

My business partner Reed and I laugh alongside the Chef and exchange a look of “why not?” Who are we to doubt someone’s goals, however far fetched? When we first met years ago, no one could have predicted that we’d someday have a successful business together. Life can be delightfully surprising.

We’re on Mackinac island, between Michigan’s Upper and Lower Peninsulas, and it’s like we’ve stepped back in time. There are no cars or chain stores on the island, which is mostly covered with Mackinac Island State Park. These days it’s primarily a tourist destination, though for decades beginning in the 1700s, the island was once the strategic center of a bustling fur trade.?

I’m intrigued by the idea of fur traders—indigenous people, the French, British, and, eventually, Americans—coming together, paddling by canoes for hours to exchange goods against a backdrop of negotiations and hustling. This commerce represented the culmination of months, if not years, of perseverance, risk taking, and fortitude.?

It’s amidst this history of entrepreneurship that Reed and I are aptly holding the annual strategy planning session for our agency. The three-day offsite had been on hold due to the pandemic. I’m quickly reminded that despite our frequent Zoom and phone check-ins, often multiple times each day, they’re no substitute for connections that are made stronger through in-person visits. We use the time to share gratitude for our successes, take stock of lessons learned, and re-visit our intentions as an agency, co-owners, and individuals.

A couple days earlier, as I was waiting for my flight at SFO, I pressed play on a podcast I’d recently gotten hooked on: Dolly Parton’s America . In episode two , she describes the origins of her relationship with Porter Wagoner , the country music singer who first introduced Dolly to the world on his TV show. He gave her the opportunity, but she created her own spotlight. Soon enough, Dolly and her ambitions outgrew the show and Porter himself, who became threatened with her success. “When he hired me...he didn’t know that I was a serious entertainer, a serious writer...He didn’t know how many dreams I had,” she explains.

Dolly knew she had outsize dreams, but what about those times when we’re not even aware of our own aspirations? Whether you’re afraid, bogged down in the day-to-day, or held back by self-doubt, there’s no shortage of opportunities to stay on the treadmill, putting one foot in front of the other, overlooking that there’s possibility out there, on a different or new path.

I’d been working at a company called Doctor On Demand for about three years when it hit one of its many inflection points of growth. We had a new CEO and a trajectory that required more leaders at the helm. At the time, I was VP of Enterprise Marketing but the company didn’t have a marketing leader overseeing all of marketing, including consumer and corporate marketing.?

When the CEO discussed at an all-hands meeting that we’d be opening up a search to hire the company’s first Chief Marketing Officer, I was heads-down, focused on my area of the Doctor On Demand world. My colleague and friend Frank, who was VP of Sales, sent me a simple text during that announcement: You’d make a great head of marketing, he began. And he went on to list the reasons why it made sense to him and his team.

That one moment gave me a sense of clarity, like when I got glasses for the first time as a 7 year-old. The world around me was the same but I saw everything differently. It was as if something was holding me back earlier (myself, perhaps?) and now I could give myself permission to dream bigger.?

After giving it some thought, I pitched the CEO on giving me the interim-Chief Marketing Officer position (he did) and then sometime later went on to be head of marketing at Freenome, another fast-growing healthtech startup. Sometimes, you don’t know you need glasses until a friend hands them to you.?

Several years later, that encouragement from Frank and others along the way helped me start Best Friend Jack with Reed. Throughout my life, I was always drawn to work that involved creativity and creating things, and it was time to combine that with my experience in marketing, advertising, and even as a practicing physician—into a boutique marketing and branding agency for high-growth healthtech companies. Over several years, it came into focus—just how much the process of creative ideation fuels me.?

Each time, I’m filled with anticipation. Cultivating a creative project—like a rebrand—painstakingly, until it begins to take shape and grow in meaning, and then launching the project into the world to motivate people to take action, change their opinions, and even change their lives. Along the way, there’s always fear of a creative project not fulfilling its potential, but even the fear is energizing. I’m certain it’s because we’re experienced enough now to recognize the patterns of the creative journey and to use our tools and approaches to work through the blockers—a thrill every time.

JJ Abrams, the film director, producer, and screenwriter, talks about how he was missing that thrill early in his career. He was stuck as a junior writer working on re-writes for movie scripts, feeling like he’d “lost any sense of purpose or joy.” Right around that time, he met Katie McGrath (who later became his wife) and “she reminded me to write things you care about, write what you love.” Soon after that he wrote the pilot of the TV series Felicity , and he would go on to co-create Lost and direct Star Wars: The Force Awakens .

In an interview , JJ discusses how being uncomfortable is part of the process, and that “All creative endeavors are a leap of faith.” Creating things—whether it’s a TV show, ad campaign, new brand, new company—requires faith that something deep and meaningful will be borne out of truth telling, insight mining, hard work, and experience. Faith that the end product that you put into the world will enrich people’s lives and minds.

It would be ideal if you were always your most abundant source of faith. In reality, we all have moments of self-doubt, which is why it should be non-negotiable to surround ourselves with people who will support us when those times arise. When I was training for a marathon , I paired up with a running partner who kept me motivated when inevitable fatigue set in, and I was able to do the same for her as we logged mile after mile. Our respective burdens were made lighter by our mutual support.

Strong partners—in work and in life—sustain you through times of uncertainty and fatigue, both mental and physical. When Reed and I were naming our agency, we landed on Best Friend Jack because best friends help you achieve your goals, through good times and bad. Best friends are there for you. They tell it to you like it is. They bring out the best in you.* And it’s with that philosophy that we work with clients and, frankly, conduct our personal lives.

Each time I explain the meaning behind our agency’s name, it’s a reminder to check in on the kind of life I’m building and nurturing. Is it a life in which I’m helping people push past self-doubt and tunnel vision to achieve their dreams? One that involves people helping each other take those leaps of faith? One in which people hand each other glasses when we need to see the world—and ourselves—in a different way??

*P.S. If you're wondering why the name “Jack” is in our agency name, that’s a story for another time. :)

---

For my latest articles and updates, follow me on Substack . And, as always, drop me a line . I’d love to hear about the last time a friend helped you see clearly.