Lessons in Success From the Rich and Famous

Photo-Illustration: by The Cut; Photo: Getty Images

Sometimes we meet in person in sprawling hotel suites or homes with panoramic views. Other times, we meet onscreen, their images appearing from rumpled beds or infinity pools or boats bigger than my apartment. The dynamic is always different, ranging from stiff and transactional to warm and intimate, but in all cases, our interactions are largely one-sided — they share, I recede. Good ghostwriters are invisible, giving away our best lines without leaving a trace of ourselves.

As a celebrity ghostwriter, my career has been an unintentional master class in ambition, offering intimate glimpses of those who are The Best at what they do. Over many hours of interviews, I gather their memories, histories, and personal philosophies and spin them into cohesive narratives, often without credit. I’ve worked with an array of talent, from entertainers to athletes to entrepreneurs, many of whom unironically refer to themselves as “game changers” and “thought leaders.” Together, we’ve penned memoirs, how-to guides, and self-help manuals, all promising their secrets for winning at life.

My friends are always after the gossip. “Who’s nice, and who’s a monster?” “Why did they really break up?” I never write and tell — not only out of professionalism but because those stories aren’t that compelling. Tabloid fodder can never compare to the wonder that is witnessing their drive in action.

In my experience, there are core tenets of the Über-ambitious — gall, grit, and gumption — but their motivation is never fame or fortune, even if those are welcome by-products. There is always a deeper why, an emotional force that keeps the engine running. Often it’s invisible, some gnawing desire or inner conflict that can never be resolved. It could be an absent or critical parent or a bully whose words cut deep. To honor a beloved mentor or uphold a family legacy. To increase representation, to become the role model they wish they’d had as a kid.

Once their eyes are trained squarely on the prize, all else is weighed against it. “The most important thing is to get clear on what you want,” explains one wellness mogul. “It creates instant boundaries and helps remove distractions. Before I agree to anything, I ask, ‘Will this get me closer to my goal?’ If the answer is no, I don’t do it.”

I once stumbled across a to-do list of sorts while using an actor’s bathroom. (For the record, I wasn’t snooping; it was taped to the mirror and impossible to miss.) Where we mortals may list things like chores and errands, this read like a step-by-step plan for world domination. It included winning awards, directing a feature film, and launching a lifestyle brand along with the power players to appeal to in order to make it happen. I’ve seen this attitude time and again, albeit in different forms: approaching life like a video game, a challenge in which one perpetually tries to level up. One entrepreneur told stories of jumping from job to job to job, thinking nothing of blowing up her résumé and reputation when something didn’t align with her tough-to-meet ideals.

Of course, all that striving comes with a fair amount of sacrifice. “I haven’t seen my kids in weeks,” sighs one multi-hyphenate, whose social media bursts with heartwarming photos actually taken by their nanny. Missing out on big life moments is par for the course — holidays, formative experiences, family milestones, even postponing one’s own wedding to accommodate a grueling work schedule. Where balance is virtually nonexistent, relationships often suffer. I’ve watched similarly driven partners grow apart, as each is off chasing their goals, while dissimilar pairings can leave one partner feeling left behind.

For many reasons, ambitious people often keep like-minded company. As one Hollywood heartthrob told me, his inner circle is carefully curated. He surrounds himself with people who are relentlessly positive, motivated, and energetic, essentially recruiting a full-time hype squad. “Their energy rubs off on me,” he explains. “Their success gives me focus and makes me want to get things done.”

I can attest to the power of proximity, because sitting on the sidelines of megasuccess made me want to get in the game. For years, invisibility provided a safe, cozy place to land without putting myself on the line. But when you spend time with those who reside in a spotlight, you can’t help but feel drawn to its glow.

One morning, I met a beloved TV personality for breakfast. As we sat tucked in a corner booth, his cap and sunglasses doing nothing to curtail curious glances, the conversation veered into unfamiliar territory. “What’s your dream?” he asked, cutting into a stack of pancakes. I hesitated, unsure if I’d heard correctly. “I mean, you can’t just want to do this forever, right? What is it you really want?”

As his kind face waited for an answer, I realized it would be easier to divulge my deepest fears or strangest sexual encounters. I knew the shape of my dream, its outlines as sharp and clear as his features before me, but I couldn’t will my lips to speak it. Like many people, I’d internalized the belief that giving voice to my aspirations was gross, obnoxious, and egotistical. Especially as a woman.

Until that morning, I’d always thought I was ambitious. Now I saw I wasn’t even close. How had I failed to notice that my own desires were mired in shame? When people asked what I did for a living, I’d often put “writer” in air quotes, even though it was my full-time job. Who was I to want a voice, an audience, for my name to grace a book’s cover? Who was I to pursue the same things I routinely helped others create? As I made my way home from breakfast, I decided it was time for a change.

The most powerful tool of the truly ambitious is that they harbor no qualms about voicing or pursuing what they want. It doesn’t mean they never struggle with insecurity or impostor syndrome or even the fear of failure. But when opportunity presents itself, they never ask, Why me?

One of my favorite questions to pose to clients is if they were surprised by their achievements. I have never been met with false modesty. “Honestly …,” they always begin, before confessing to some hunch about predestined greatness.

I’ve been writing more as myself these days, but their words still rattle around my mind. I hear their stories of detours and stumbling blocks and how they forged ahead anyway, ever in pursuit of what makes them feel alive. I’d like to believe that’s possible for all of us, whether your definition of success includes yachts and Oscars or nachos and relative sanity: to grant ourselves the permission to try.

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Lessons in Success From the Rich and Famous