The Office & PA Show
Remember: being yourself will always lead you to the life you were meant to live
We had the privilege of interviewing Libby Moore (Former EA and Chief of Staff to Oprah Winfrey), and discussed her role with Oprah, her most memorable moments and stories in her career so far, what inspires and motivates her today, and the best piece of advice she could give PA’s, EA’s and Office Managers.
1. How did you land the role of working alongside Oprah?
Libby: So the short version is that I found out about this position through a networking group that I was in which is called New York Celebrity Assistants (NYCA). One of the members sent an email to the group saying, “I was just contacted by an executive recruiter in Chicago and they are in search of a Chief of Staff/Executive Assistant to a high profile person", and it had this list of 150 responsibilities. The first two things said “co-ordinate private plane/pilot/aviation crew” and the second thing said “co-ordinate hair and make-up team". I knew in that instance it was Oprah because I thought “hair and make-up" - that means this person must be on TV, and “private plane” means this person has a lot of money! That must be Oprah. So that’s actually how it came to me.
The back story is I moved to New York to be in comedy. I really needed to go forward in my comedy career because I was in a little sketch comedy group and stuff, and so I started sending writing submissions to The Rosie O’Donnell Show. After 10 months, it just wasn’t happening. So one day on the subway to work I just said this prayer and I sent this intention out to the universe. I said “clearly you don’t want me to have this job with Rosie so whatever it is I’m supposed to do, every atom, soul and molecule in my body, mind, soul, show me what it is and be clear, and I’ll do it". Then it was maybe 4 or 5 weeks later that this job with Oprah came in.
Even though it’s that classic story that we’ve heard a million times, there's something in you that says I believe I can do this. The power is in the belief of it, and when I finally released that Rosie job - I did everything in my power to try to get that job - but once I kept hitting a wall, hitting blocks, hitting a wall, hitting blocks, I said “clearly this is not meant to be”. So when I truly released it, that’s when the amazing job came in. It’s like I opened myself up to something bigger than I could ever dream in my whole head. That’s when the big fish came which was Oprah.
2. Tell us about some of your most memorable moments, and some of the biggest lessons you’ve learnt along the way.
Libby: There are so many memorable moments. The absolute number one, most extraordinary experience of that job was getting to know Oprah Winfrey as a friend. As a human being, as a friend, she is one of the kindest, smartest, funniest, most generous people on earth. I mean, she truly is an extraordinary human being on so many levels. And in addition, she is exactly that, a human being, who is working on her own self and overcoming her own stuff in her head. We’re all trying to manage ourselves, including the Pope, including Oprah, and she’s a human being who’s really striving to work on herself and make herself a better human being. That is hands-down the most extraordinary thing. It was getting to know her for 11 years. And I would say helping the team that created Super Soul Sunday which is her show on her own network. That was extraordinary.
I would say there were so many regular people doing extraordinary things who either came across her path or came through the Oprah Winfrey Show that I met. Mattie Stepanek, who was a little boy who had a rare form of muscular dystrophy and he died two weeks before his 14th birthday. That kid, who was basically 14 when he passed, he taught me so much about life, and the importance of a simple breath, when he eventually ended up in a wheelchair and oxygen tank to breathe. He taught me so much. Meeting him and his mother, who has the same disease, taught me so much about human resilience, and the human heart that was hands-down one of the most incredible experiences of working with Oprah.
Also I would say, this goes back to Oprah as a person, the lessons that I learnt from her through her achievements and her mistakes. Those inner circle lessons.
3. Why did you decide to leave and how did you come to this decision?
Oprah gave a 2 year announcement before the show ended. So she let the entire company know "in two years, this show’s ending after 25 years, I’m moving on and I’m launching the network". So maybe 3 months after she gave that announcement, I said to her one day “Look, I’m with you 1000% until the end of the show, and I’ll help you transition into the network, it’s going to be a massive change for you”. She was moving from Chicago out to her home in Montecito, California, and that was going to be a big change. I said “I am with you in this role as your Chief of Staff until you feel settled and stable. Once you feel settled, it is time for me to move on from this job” because it will be 11 years at that point. I was absolutely fried, which is the answer really. I was just burnt out. It was 24/7 for 11 years, I had managed a team of 5 assistants, the security team, the aviation team, and I was her key liaison for every point of business. I was the last stop before anything went to Oprah. It didn’t mean I was running everything, it just meant everything filtered through me, so I never saw my family or friends, I went through 3 relationships when I was in the job, and I realised I was turning 45. I just thought I want a life, and I really don’t want to get cancer - like I really felt like if I’m going at this pace, it’s unsustainable!
So basically, she said “I get it”. And I said, “My dream is to stay in your Oprah universe in some capacity - I don’t want to leave you or the company, I just need to move on from this job and I’d like to roll up into some other position”. She said “I totally get it - we’ve got two years, let’s decide what that is”.
Honestly, over those two years, I think we kind of ignored it the first year because it was such a crazy thought, because we’d gotten into such a fantastic groove for both of us. Then in the last year, things I offered really didn’t work for her, and things she offered were wildly generous but I had no interest in being a TV executive. So that’s it! We couldn’t confide on what is was. So I hired someone, I trained the new Chief of Staff for 4 and a half months. And when she really felt good and Oprah felt good with her, then I moved out to LA and helped launch Super Soul Sunday on her network - that was probably another 4 or 5 months. Then January 1st 2012 I left amicably.
It was really hard for both of us. But I had said to her also when I gave that notice, “I want to stay with you but if we can’t agree on what the role is then that means it’s God’s universe saying you need to go out into the world and share this experience in another form.” And she understood that.
But we both thought at that time “This is so easy! Of course we’re going to figure out what I’m going to do next” which was another great lesson. Honestly I was like “Are you kidding me?! I’ve given like 11 years to this and you can’t just magically make a (position)?” That’s how I truly felt. But in hindsight, 5 and a half years later, I look back and I go “this is so perfect” - so beautiful. So that’s why I’m able to work with people, coach people now, or just talking to friend or whatever, it’s like I’ve been through it. It’s okay, it’s going to be amazing.
4. What inspires you and motivates you today?
Libby: That’s a great question! I am inspired by spirit, the universe, God, source, the divine - number one. Whatever you want to call it. I believe we are all talking about the same thing, and we’re arguing over what to call it, and in many cases we’re killing each other over what to call it. Therefore, we’re missing the power and the magic, and the message of “it” because we’re all talking about the same thing. So number one, that’s what inspires me - that source, that divinity, that divine thread that threaded throughout every single person in every living breathing thing on earth. That inspires me.
Human beings inspire me, the human spirit inspires me, creativity inspires me. Surfing - I used to surf when I was like 14 or 15 and then I picked it up again when I was 45 which was the year that I left the job. I turned 45 and my girlfriend gave me a surfboard and I picked up surfing again and started doing it, and I felt so vibrant and alive. I took a year off after I left, or I took a year “on” as some people say, and I just said that I’m going to follow my heart for 365 days and see where it leads me.
And at the end of that year, people would say “what are you going to do now?”. I’d say “I’m doing exactly what I did this year” which is connecting with people, heart to heart, energy to energy, soul to soul, and if it feels right, I go for it, and if they don’t, I don’t. Even with clients, there have been some amazing business opportunities that have come my way to coach some global businesses that would pay great money, but there was something in me that was like “it doesn’t feel right”. So I just trusted that passing on something that doesn’t feel right, something even better will come.
Interviewer: I think that’s a great lesson to learn - just knowing what your gut feeling is, and going with that, and being inspired by that as well. I think everyone knows deep down when something doesn’t feel natural, and then when you do go for that thing that you feel is right, everything just falls into place.
Libby: Exactly. And, it’s not only just business right? It’s not just opportunities and jobs - it’s relationships, it’s friendships, it’s partnerships, it’s all of that.
The other thing that truly inspires me a lot is people that are living in a new paradigm. People that look at the world today, and clearly the old way of doing things is breaking down globally, the old structures of government and the Middle East too. Our president - hello! It’s so crazy. It’s like everything as we knew it is breaking down. So there’s two kinds of people. There’s either people that look at the world today and go, “Everything’s in disarray, everything’s crumbling, this is horrible” and they’re focusing on that and they’re therefore creating toxic energy in their body and that’s what they ripple out. Or people who go, “Everything is breaking down as we know it - this is an incredible moment in time and opportunity to create exactly what we want”.
5. What sort of advice would you give to EAs, PAs and Office Managers?
Libby: Here’s a piece of advice that I tell everybody - be yourself, with all people, at all times, in all situations. If you do that, even when it’s uncomfortable, being yourself will lead you to the life you were always meant to live. That is what will lead you to the partner that’s right for you, the job that’s right for you, on and on and on. When we try to act like someone who we’re think we’re supposed to be, whether it’s like a new relationship and you’re trying to act all perfect for your new partner, that’s where we screw things up because it’s not you. The truth is, I’m still working on it at 51 years old. It’s not like just because I’m doling out that it means I’m perfect and it’s no problem for me! There are definitely still times that I feel wildly insecure, or uncomfortable. Or a whole table has one opinion and you feel differently. I’m either quiet, or I subtly say how I feel, or I just don’t say anything at all. So it’s a learning curve.
Interviewed and written by Lena Taylor, Marketing Executive, Conferenz. For more updates on Office and PA events, go to conferenz.co.nz