A few years ago Libby Moore ventured on a new journey she called ‘The Libby Moore Gypsy Tour’, which consisted of 365 days with no plan at all – other than to simply follow her heart. Fast forward to the here and now and she is a private coach, speaker, connector and mentor to high achievers who are looking for deeper meaning in their lives. She’s a quiet force; the epitome of positivity.
For 11 years she was talk show host and entrepreneur Oprah Winfrey’s chief of staff and executive and personal assistant.
I ask how her journey to such an opportunity unfolded. “My journey to Oprah was a pleasant surprise. I started working professionally at 20 years old, after I graduated with a degree in radio and television from Endicott College outside of Boston. I sold radio and newspaper advertising, and I was a copywriter for another radio station. Then I moved to Boulder, Colorado and skied for two years while doing odd jobs, which included babysitting, cleaning houses and office buildings, and working at a movie theatre. My mother was freaking out!
“At 25, I moved to New York City because I had a dream to write for Saturday Night Live, a popular sketch comedy show in the US. About a month after I landed in the city, I got a job as personal assistant to Maury Povich, a TV talk show host. I was with him for three years, and then I left to pursue comedy. After about two years of struggling to make ends meet, I took a job as an executive assistant to Jann Wenner, founder of Rolling Stone magazine. I was a second assistant, and did that job for four years.
“During that time, I had an opportunity to interview with the head writer of Saturday Night Live. I left that meeting knowing that I would never be a writer there. So I refocused on becoming a writer for the Rosie O’Donell Show. After 10 months of sending writing submissions to the head writer (with no reply), I finally gave up on my ‘dream’ of being a comedy writer.
“One morning while taking the subway to work I said a prayer; ‘Okay God, clearly you do not want me to write for Rosie O’Donnell – and you know how badly I wanted it. So whatever it is that I am supposed to be doing, every atom, cell and molecule in my body, mind, soul and spirit is open to it. Show me what it is. Shine a big fat spotlight on it, and I’ll do it.’ I meant that with all of my heart, and I completely opened up to ‘the possibilities’ that were out there for me.
“About four to five weeks later, the opportunity to be Oprah’s chief of staff came along. I knew immediately that that was the job for me, and that’s why the other jobs didn’t work out. I got the job, and worked with Oprah for 11 years. So essentially, I had to give up my ‘dream job’ of comedy writing to get my dream job.”
I’m sure that none of you reading this will be surprised to hear that her days were long and full-on from start to finish. “I typically arrived around 7.30am and got home around 9.30pm. First thing in the morning I would do a briefing with Oprah while she was getting ready for the show. Then I would pull my team together to pass along the information and delegate action items.”
Libby managed a team of five assistants “who were all excellent at their job. We worked together as a team, and that was the only way to handle a life of that magnitude. Throughout the day there was a constant stream of meetings, phone calls, questions, and I received about 250+ emails a day. So it was non-stop from the moment I walked through the door until I walked out late in the evening.”
So how did she stay on top of the steady stream of demands? “It was the team of assistants that I worked with. Without them, I would not have lasted six months. It was truly a team effort.”
And how did she handle the stress? “Meditation, prayer and journaling.”
She describes her working relationship with Oprah as “excellent. It was built on a foundation of trust. It was something that organically developed over a period of time.
“As the years passed I felt more and more comfortable voicing my opinions, concerns and ideas. At times my input was in opposition to her own opinions/perspectives. That was an important part of the reason she grew to trust me. I was not afraid to stand in my truth, even if at times it was wildly uncomfortable for me. At the end of the day, she knew I had her best interests in mind.”
So what did she enjoy most about her role? “Being able to have an ‘apprenticeship’ with one of the most extraordinary people of our time. I also loved travelling – meeting people from all walks of life – and the numerous life experiences that expanded me in so many ways. And getting to watch tapings of The Oprah Winfrey Show for more than a decade was a pretty sweet job requirement. It was like getting a PhD in inspiration.”
What would she pinpoint as the most challenging part of her role? “Having very little personal life outside of work” resulting in “missing a lot of major life events with my partners, family and friends.”
We chat about the future of the PA role and what it will be. “It is becoming a more strategic partnership role, with direct impact on the business, which impacts the bottom line. I know many EAs/PAs could be running some of these companies.”
And her words of wisdom to PAs today are “stay true to yourself; take the high road in all circumstances; and try your best to create quality time for yourself, partner, kids, family and friends.”
I’m intrigued to hear about her new role as an executive coach and speaker and what it entails, as it’s seemingly so far away from her previous professional position. “I help high achievers reconnect to the important things in life, and reignite that ‘spark’ that has dulled under the swirl of ‘life and career.’ Many people I work with have ‘made it’ yet feel hollow and empty. Other people just feel a little ‘off track’ in their life or career and need inspiration to get back on track. All of my sessions are done on the phone, and I feel that people move forward a lot quicker that way. It is truly what I am most passionate about – helping people reconnect with their higher self. As a speaker, I love using my own life story/career path to help inspire and reignite people’s own passion in their life.”
When in search of down-time she says: “I love spending time with friends – laughing, connecting, telling stories. Exploring New York City is always exciting. Spending time in the country and taking endless road trips. I also enjoy spending time alone contemplating life, mystics, spirituality.”
So, what’s next on the cards? “More international speaking engagements, and I’m very open to creative collaborations with out-of-the-box thinkers. I am also currently working on a project that will be super exciting once it is announced.”
We play a round of quick fire questions to close the interview. Who would play her in a film of her life? “I have no idea, but I would hope she is gutsy, brave and funny, and probably a bit of a tomboy.”
Her dream dinner party guests would be? “My closest friends, with Oprah, Michelle Obama, Lauren Hutton, Adele, Amy Poehler, Tina Fey and Kristen Wiig.”
Which book changed her life? “A book that Oprah had recommended early in my time with her – Discover the Power Within by Eric Butterworth. It was published in 1968, and it’s about finding the ‘divine’ within ourselves.”
What qualities does she most pride herself on? “Integrity, authenticity, loyalty and humour.”
And, if she could pick anywhere in the world, where would she most like to be right now? “At home in the West Village, New York City. Entering autumn, my favourite season, and on the verge of so many possibilities that are coming my way. I feel very grounded here, and I can feel an electric current of excitement in the air. It’s maybe the first time I haven’t felt the desire to be somewhere other than where I am.”
The epitome of positivity right there.
This interview originally appeared in the November/December 2016 issue of PA Life. Read the full online issue HERE