50 Conversations To Transform Your Life

Lindsay Ratowsky by Daniel Johnson

Ten years ago, I came across a blog called "fifty coffees”. The idea was simple yet profound: a woman in her early thirties, navigating a career transition, decided to have coffee with fifty people to help inspire her path forward.

I loved the idea and shared about the blog countless times, never imagining that I’d find myself sitting across from its creator in a mutual friend’s living room a decade later.

That’s how I met Lindsay Ratowsky, founder of Nicely Done, an agency that helps thought leaders build sustainable businesses around their expertise, and co-founder and former COO of Esther Perel Global Media.

The story of fifty coffees illustrates a valuable insight: In moments of transition, our instinct is to rush toward certainty. Yet, it’s when we dare to pause in the unknown, that we can unlock the possibilities that transform the trajectories of our lives.

The Power of Pause

In the spring of 2014, Lindsay found herself at a crossroads. For a decade, she'd been the person behind powerful people — a celebrity assistant in Los Angeles, then executive support at a fast-growing nonprofit called charity: water in New York. When her role there ended, she faced a familiar question: What’s next?

"I remember coming home and calculating how many days I could survive on oatmeal before I needed to find a new job," she told me, laughing at the memory. Even so, she resisted rushing to apply to positions. Instead, she decided to have coffee with fifty people to inspire her next steps.

The genius of fifty coffees is that it went beyond traditional networking. Intuitively, Lindsay approached each conversation prioritizing her relationships themselves, not just where they might lead. She focused on genuine curiosity, deeper connection, and inspiration, not getting referrals or introductions.

This approach wasn’t just refreshing — it was powerful. Lindsay created space for these coffees to unfold naturally, allowing each one to be an exchange of ideas, perspectives, and possibilities.

Through her conversations, Lindsay tapped into a sociological concept I first learned from professors Jon Kleinberg and David Easley fifteen years ago: the power of "weak ties." It’s often our broader network, not our inner circle, that introduces us to new possibilities. While we often share circles and perspectives with our close friends, acquaintances bridge us to different worlds.

As I reflected on this with Lindsay, we realized how much her project embodied this principle. By widening her world with intention and openness, she uncovered an opportunity that propelled her journey forward in a surprising and profoundly transformative direction.

An Unexpected Partnership

Years ago, a seasoned executive told me something that forever changed how I think about career transitions: "I've never applied for a job." He explained how opportunities often move through networks before they're posted publicly. Through building relationships, he’d uncover and even help shape roles that were a perfect fit for him.

When I shared this story with Lindsay, she smiled. "I actually haven't applied for a job since college either," she said. This wasn’t just luck — it was the result of consistently investing in her network and creating conditions where serendipity could flourish.

In moments of transition, there’s a temptation to hide away until we figure them out. With fifty coffees, Lindsay did the opposite. She opened herself up to exploration and connection, embracing the unknown as a canvas for creation.

Eventually, the project led to a pivotal moment: her unpublished coffee date with psychotherapist Esther Perel. They'd crossed paths before — at one point, Lindsay had even helped review job descriptions when Esther was hiring. But, it was their fifty coffees conversation that opened the door for their acquaintance to become something more.

When they sat down, Esther was at an inflection point: Her viral TED talk had introduced her to a global audience, and her therapy practice had a waitlist far beyond her capacity. She needed someone who could help her support more people — someone comfortable with uncertainty and ready to build something new.

"Within five days, I was looped into her whole world," Lindsay reflected.

Over the next five-and-a-half years, they built Esther Perel Global Media from the ground up, creating new revenue streams through digital products, releasing the hit podcast Where Should We Begin?, and launching Esther’s second book The State of Affairs.

Their partnership resulted in an exponential leap in both of their careers. For Lindsay, it transitioned her from administratively supporting high-profile individuals to building a global media company. For Esther, it evolved her work from one-on-one and couples therapy to supporting millions through digital channels.

Through their collaboration, they created something neither could have alone — something far beyond what either imagined when they first sat down for coffee.

Building Bridges

Lindsay's career trajectory reminds us of something essential about transitions: They don't have to be solitary acts. While there's often pressure to figure everything out alone, the richest possibilities emerge through connection.

The original fifty coffees never reached fifty. After fourteen published conversations, Lindsay found herself swept into the next chapter of her story. Yet, a decade later, the blog still draws thousands of readers monthly — perhaps because it captures something timeless about navigating uncertainty.

At some point, we all face the question: "What's next?" The answer rarely comes from a perfect plan or a singular flash of clarity. Instead, it often emerges through opening ourselves to possibilities — through the messy, beautiful, and unpredictable exchange of ideas with others.

Perhaps the most powerful question in times of transition isn't, "What do I do?" but rather "Who can I talk to?”

Because your next step might not be waiting for you in your current thinking, but in the serendipity of your next conversation.

Love,
Levina