Libby Moore is an international speaker, executive coach, consultant and founder of LoveX Global. Prior to this, Libby was Chief of Staff and Executive Assistant to Oprah Winfrey.

Libby Moore Oprah Winfrey EA Leader Assistant

Libby shares a bit of her life story, including the behind-the-scenes story of how she ended up working with Oprah. Libby’s energy and curiosity was so contagious she had me talking about parts of my story I’d forgotten about.

We talk about the dehumanizing interactions assistants can experience, especially when working with high-profile executives. We also talk about self-confidence, and treating people with dignity no matter their title.

Enjoy the episode and please do reach out to Libby via her links below to say hi!

Read a summary of our conversation here.


Download the first 3 chapters of my book for executive assistants, The Leader Assistant: Four Pillars of Game-Changing Assistant, for FREE here or grab your copy of the book on Amazon here.


I’ve learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.

– Maya Angelou

Libby Moore Leader Assistant Podcast Chief of Staff Oprah Winfrey

Libby Moore is an international speaker, executive coach, consultant and founder of LoveX Global. She is passionate about helping individuals and companies align with their higher self for a higher purpose.

Prior to this, Libby was chief of staff, EA to Oprah Winfrey, an executive assistant to Jann Wenner, publisher of Rolling Stone, and a personal assistant to Maury Povich. She spends her time in Vancouver, New York City and Cape Town.


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Libby Moore 0:00
Hi, my name is Libby Moore. And today’s leadership quote is from Dr. Maya Angelou. I’ve learned that people will forget what you said. People will forget what you did. But people will never forget how you made them feel.

Podcast Intro 0:20
Leader assistant podcast exists to encourage and challenge assistants to become confident game changing leader assistants.

Speaker 2 0:32
It’s episode 55 and heres your host my dada.

Jeremy Burrows 0:38
Hey, leader assistants. I’m very excited to be speaking with Libby Moore, former executive assistant and chief of staff to Oprah Winfrey. She is a very awesome person and I got to meet her in person several months ago, and just very excited to share her story and some of her wisdom from working with Oprah and others throughout her career. So yeah, stay tuned for an exciting interview with Libby. But first, I want to share some exciting news. As a lot of you know, I have been working on writing a book for assistants for the last few years. And I am very excited, it’s getting closer and closer to launch the summer. I don’t have the official date yet. But stay tuned for that. But in the meantime, I’ve put together an exclusive preorder bundle that comes with a signed hardcover copy of the book that comes with an assistants lead, tri blend premium t shirt. It also comes with a couple of assistants leads stickers. And then also access to The Leader Assistant online video course.It comes with a bunch of bonus videos, screen shares, training material to go alongside extra material and extra bonus content to go alongside the book. And then I also include the how to manage constant interruptions online course in that bundle. So you can get the book in hardcover, you also get the advance digital copy right away. So you don’t have to wait for the hardcover to come out that you can just go ahead and get the PDF and start reading it right away. So it comes with a PDF right away. It comes with the hardcover, a t shirt, stickers, online courses. And then also a 30 minute coaching call with yours truly. So this whole bundle is about a $500 value and I’m selling it for $149. And I’ve got a limited number of them available. So go to to check out the preorder bundle that’s Again, it’s $149 comes with the hardcover, the t shirt, stickers to online courses, a 30 minute coaching call and the PDF download of the book right away. So hope you can check that out. Very excited to release the book to the world but I wanted to put together this special bundle beforehand for those of you who are excited to jump right in and get some extra bonuses. So

Hey, everyone. Thanks for tuning in to The Leader Assistant Podcast this is your host, Jeremy Burrows and today I’m speaking with Libby Moore. Libby, how’s it going?

Libby Moore 3:23
Fantastic. I’m so happy to be talking with you today. Thank you, Jeremy.

Jeremy Burrows 3:27
Yeah, it’s great to have you. What part of the world are you in right now?

Libby Moore 3:32
I am in Vancouver, Canada right now. And it is cold and snowing and gorgeous out. I love it.

Jeremy Burrows 3:40
Awesome. Yeah, awesome. I got to go to Vancouver. I think it was like, a year and a half ago. For the first time. It was beautiful.

Libby Moore 3:49
Isn’t it gorgeous? I love the mountains. The water the islands, the city? Yeah, it’s really very cool.

Jeremy Burrows 3:55
That’s great. What was your very first job and maybe what skills did you learn in that role that you still use today?

Libby Moore 4:01
Okay, so you mean my very first job that I got paid to do?

Jeremy Burrows 4:05
Yeah, you can you can some people like to share their Oh, you know, I babysat or I sold candy bars. And then there may be first taxed job.

Libby Moore 4:14
Yeah. Okay. I’m gonna go way way back because I think it’s relevant. So I like to think of this. I really didn’t put this together until probably about four years ago. But I really think my very first job was emotionally caretaking my mother as probably like a 7, 8, 9 year old and not that she asked me to do that. But I’m one of four kids. So there’s an I have an older sister then there’s me the second. I have a younger brother and a younger sister. So I wasn’t the oldest I wasn’t the only boy and I wasn’t the baby. And I think that is that second child I was kind of like where’s my place in the family and when because I was I’m super in tune to people and I especially as a kid. I think when I noticed my mom needed attention or needed to be taken care of, in some way Emotionally, I went right there and, and got rewarded for it because I could see how I could make her happy. And that felt so good to me. So it’s kind of interesting that intuitively understanding that as a kid, and just kind of doing that, and then it became, for my friends and co workers, it just kind of led up to what I do today, which is coaching people. So I like to start say, I started coaching when I was about eight years old. And then, as far as my first real job job, my brother and I started a lawn mowing business. My dad owns a landscaping company. And people always ask him, do you know anyone who cuts lawns? And he’d say no. And so he because my brother and I had to cut our lawn at home growing up when we were little kids. He said, Do you guys want to start this business? So when I had my license, I was 16, my brother’s 14, and we would drive around and cut people’s lawns and send invoices and everything. So that was my very first job job.

Jeremy Burrows 6:04
Wow, that’s awesome. So yeah, that’s, I mean, you ran your own business. When you became an assistant later on, and we’ll talk a little bit about how that happened. But did you kind of see the parallels of running your own business and being an assistant?

Libby Moore 6:21
I really didn’t. I mean, when I was doing it, honestly, I did not. And I think more so probably, it really became apparent to me when I really did leave my job with Harpo Productions as Oprah’s chief of staff and then went off on my own. And then when I started my coaching business, then it really kind of all came back to invoicing and things like that. But I will say also, because my, my, this did actually help me as an assistant when, as a kid, like I said, my my parents own this landscaping business, which was sod farms, lawn maintenance, stuff like that. And it was a small family owned business. So our phone at home had the the home line and the business line, and it was just like a slightly different ring. Well, if my parents were unavailable or not at home, we were instructed on how you properly answered the phone. So people would be calling on a Saturday or Sunday, sometimes complaining about their lawn, the phone rang, and you’d hear this little like, 10 year old voice being you know, good morning, we’re Sunfarms How may I help you? And someone’s thinking, like, why is it child answering the phone, but that’s what my mom really, like, taught us how to properly answer the phone, how you do it politely and how you take a message. So I was doing that at like, you know, 10, 11 12 years old and up. And so I think there’s, there’s kind of an interesting, I never in a million years thought I’d be an assistant. My first job was with Maury Povich as his personal assistant, once I got into that line of work. And it felt very natural for me to answer the phones take care of him, you know, like, kind of think ahead for him. So I would say that those things do relate. Connect.

Jeremy Burrows 8:07
Yeah. So let’s talk a little bit about your story about you know, I got to see you speak in Atlanta. And you talked a little bit about wanting to be a comedian I believe and wanting to get into that world and so maybe just kind of give us a snapshot of your career from the lawn business days on.

Libby Moore 8:30
Yeah, okay. Well, oh my god, there’s I’m gonna say this because I’m sure there are some people who are listening who think wow, I haven’t I did all this stuff before I became an assistant Am I too late in the game or something like that? I did so many different jobs Jeremy prior to becoming an assistant at 25. So from the lawn care was, you know, I worked summers, I worked as a waitress. I worked as a housekeeper after college, I again worked as a waitress I was always cleaning homes on the side if I needed money or needed to make ends meet. Again, my mom taught the three girls how to like clean a house properly. So you know, I kind of always fell back on that when I needed money housekeeping and, and things like that. I you know from once I graduated from college, I sold radio advertising. I sold newspaper advertising, I worked at a record label as an assistant to the graphic designers who are doing the record label covers Reiko disk was the name of the company. I worked, I wrote radio copy at WF annex outside of Boston alternative radio station and then I went to Boulder Colorado to ski my parents were freaking out. There. I walked dogs, I cleaned houses. I was a receptionist at REMAX of Boulder. I was like a, you know, Vegetable Chopper at the boulder salad company. I worked at the movie theater the Man movie theater. I think I was 23. All my co workers are 14-15. Nobody had their license but me. So I had done so many different jobs prior to getting to New York when I thought, Okay, I’m here, I’m going to be in comedy. I’m going to write for Saturday Night live. That was my big dream. And the truth is I really wanted to perform perform on Saturday Night Live, but I was too embarrassed to say that. So I would tell people, I wanted to be a writer. And my best friend from college was a writer for David Letterman. So I thought it just I was like, oh, yeah, I want to be a writer too. And then I thought, if I get into Saturday Night Live as a writer, then maybe they’ll discover I’m funny. And maybe I could get on the show, you know, that was kind of the workings in my head. And I was in New York City for about a month. And I reached out to my younger sister’s best friend’s mother’s best friend who was an associate producer at the Maury Povich show, and took her out to lunch and gave her my resume and said, If anything opens up, you know, would you please let me know, because I just got to New York, and I’m looking for a job and I really need to work. And I was working at like a temp agency just doing odd jobs at that point. And that’s how it all started.

Jeremy Burrows 11:10
Wow. Yeah, so you had a few jobs.

Libby Moore 11:14
I mean, I think I just went over the top surface too I haven’t even given you every nitty gritty, but we don’t have time for that.

Jeremy Burrows 11:19
Yeah. That’s awesome.

Libby Moore 11:21

Jeremy Burrows 11:22
What do you love about and what did you love about the role of an assistant?

Libby Moore 11:26
Um, what I loved about it, is making people feel that they’re taken care of making them feel safe, like, okay, everything’s under control. It’s taken care of, I love, love, love that. And I would say, this is really important. Because I worked with Maury for three years as his personal assistant, he was phenomenal. One of the best bosses I’ve ever had. And I had no experience Jeremy, I mean, I failed typing in college. Okay, so I was not like, the classic executive assistant. I mean, at that time, even personal assistant, it was like 91, or 92, when I moved to New York, and the term personal assistant was even kind of unusual. It was you were a secretary or an administrative assistant or an executive assistant, but I had never even heard the term personal assistant. So I was like, what is that, it sounds like you give someone a sponge bath or something like it sounded so odd to me. But I got the job. And it was really just your, it was really more of an executive assistant with some personal assisting in there as well. So, you know, I think I was better at being a people person really being a great like collaborator, with everyone in the office really being there for Maury whatever he wanted, it was happy to do it. But as far as the tasks of that role, I never felt great. And I like to feel as we all do, like we’re really good at something. So even with Jann when I went to Rolling Stone, and I was the second assistant to Jann Wenner, the founder and publisher of Rolling Stones, Mary McDonald had been there for oh my god, like 20 25 years when I got there. And she said, I’m not going anywhere. I just needed a support person. I was like, great, because I don’t want to be the number one, I’m going to be in comedy. I just need something to pay my bills right now. So that was kind of how I went into that job. But again, I didn’t feel great at the administrative tasks, like people would call and I’d forget to write it down and then say, Oh, God, Mary, you know, your husband called, like, three hours ago, like I was kind of that person. Yeah, it’s embarrassing, in a way. But now I’m like, 53, and those years are way behind me. So who cares? Because I ended up going to Oprah, what I realized is when I got that job with Oprah, as her chief of staff, executive assistant, and I ended up managing, I think there were three people on the team when I went into that role, and then it expanded five, so I was there for 11 years. And and of those people, the team, were exceptional at what they did. Everything that you needed to do as an assistant, they were exceptional. And I was the key liaison between Miss Winfrey and the team and different departments and our, you know, family life and friends and the kind of like filtering everything that went in and out of our office. So she would delegate she would give me things to do, I would delegate it to the team, whoever is best at what they did. That is the first time when I really felt like oh, I’m a really good assistant. Because I didn’t have to do the things that I wasn’t good at. I could flourish in the things that I was really good at. reading people’s energy, great communicator, confidant, you know, traveling companion, taking care of whatever she needed taken care of. That’s what I’m really good at and it felt amazing. So I was 34 when I got that job, and it was 45 when I left. Yeah.

So can you tell us a little bit about your story of getting that job?

Yes. Um, so as you heard me say, I was with Jann for, I mean, Maury for three years. And then I like ended up giving him a five week noticing, you know, it’s time for me to move on. He said, I’ll make you an associate producer. I said, Well, I really like Thank you but I cannot produce this kind of television because it was kind of when it was getting a little cheesy and exploitive in the 90s. And, but I said, I appreciate it. And I’m going to hire someone and train them and replace myself and I did. And then I think, five days before my five weeks is up, a job came along that I took as an associate producer, on some horrible show called USA live with the People’s Court and love connection. I was terrible because I had to type transcripts. And you know, I failed typing in college. So I got fired from that job after two months, you know, was collecting unemployment emailing my friends saying if anybody needs a housekeeper, you know, I’m available. So this is like, I went from being Maury’s personal assistant to this other job that I was horrible at got fired, and then was back to cleaning houses and doing odd jobs. And then I thought, well, while I’m doing this, I should really give the comedy thing a try. So I did that for two years, I was taking stand up comedy sketch comedy improv classes, I got into a little tiny sketch comedy group in the West Village in Manhattan. But you know, struggling and trying to make ends meet. And so a friend of mine, who was working as an assistant to Barry Diller at the time said, Hey, I heard that Jann Wenner at Rolling Stone is hiring a second assistant. You should go try it for it. And I thought, well, you know what, I know how to do it. Maybe I should just go interview. So I went met with Mary McDonald. O’Brien is her married name. She’s phenomenal. We had a great interview, we totally connected. I got hired. And I ended up staying there for four years. So about three years into that. Am I going on too long, by the way?

Jeremy Burrows 17:04
No, you’re great. You’re great.

Libby Moore 17:05
Okay, good. I like giving the whole backstory so that people listening, if they’re not happy in a job that they’re in right now can file this away and know Oh, okay. So that’s how it happened. And that means that that it can happen for me as well. You know,

Jeremy Burrows 17:19
it’s not because some overnight success story.

Libby Moore 17:21
Yes, exactly. So, about three years into Rolling Stone, I really was feeling like, I’m not happy in this job. I love Mary. I love Jann. I love Rolling Stone. I love the vibe of this place, but I don’t like being an assistant. So while I was at Rolling Stone, I got an interview with the head writer of Saturday Night Live, I left that interview knowing I will not be a writer here because these are all white guys in their 40s who went to Ivy League school, and they all know each other. And they have a ton of writing experience, which is not me. So then I started setting I gave up that dream. I released that dream of Saturday NIght live. And I thought, well, Rosie O’Donnell, she has her own show. She was doing really well. I mean, she was like, right up there. One of the top talk shows at the time, and I thought I would be a great writer for her. You know, I like her humor. She’s gay, I’m gay. You know, she respects older people and kids. I respect older people and kids, like I really liked her vibe. And I thought I’d be a good writer for her. So I started sending writing submissions to the head writer and never got a reply. I mean, FedExing it one block away from Rolling Stone to you know, her show across the street and never got a reply. And I want to. So I want to tell this part of the story because I feel it’s very important. In that process, I had this laser focus of I’m going to write for Rosie O’Donnell, that’s I wouldn’t look or be open to anything else. I just thought this is what’s going to happen. So when other signs of other things came my way, I blew it off because I thought if it’s not Rosie, then it’s not for me. So on my birthday, April 17 2000 Oprah’s magazine, Oh magazine, the premier issue hit the newsstands on my birthday. And I bought the issue that day, I had taken the day off from work, and I read the whole thing cover to cover and loved it. I just feel lit up when I read that magazine. So after talking about it for a month, my mom said why don’t you just send your resume to Oprah. And I said, Well, mom, first of all, whoever is Oprah’s Assistant, why would they ever leave and to I love living in New York, who like I don’t want to move to Chicago and my friends are here. I love living here and I just shut it up. I shut it down and I kind of blew off my mom. And I like to say I blew off God or the universe because I believe that was God universe, whatever you call it working through my mom to give me a sign to do that. But I blew it off. I ignored it. So Six months later, I’m riding the subway to work to Rolling Stone. And I was really not happy in the job. And I said this prayer was sitting there on the subway, I was like, Okay, God, clearly you don’t want me to write for Saturday NIght live or Rosie O’Donnell. Because you know how badly I wanted it. So whatever it is, you want me to do every atom cell and molecule in my body, mind, soul and spirits open to it, show me what it is be clear, and I’ll do it. And I just release that prayer that intention to the universe. And I think it was five weeks later, maybe six weeks at the most. This email came in through a woman that was in a networking group and assistance networking group in New York called New York celebrity assistants, it was 100 assistants to high profile or celebrity people in New York. And it said, Hey, I was just contacted by a recruiter, they’re in search of a chief of staff, executive assistant to high profile person in Chicago responsibilities include, and the first thing said, coordinate private plane pilots Aviation team, second thing, coordinate hair and makeup team. And I swear to you, Jeremy, in that moment, I the thought was, oh my god. This is Oprah Winfrey, because Jenny Jones and Jerry Springer cannot afford a private plane. And I thought like a lightning bolt as I asked it, to be clear, it was so clear. This is why I did not get Saturday Night Live or Rosie, this is the job for me. And I went home that weekend. I updated my resume, faxed it on Monday. And it was like boom, boom, boom, boom, boom, the recruiter called. Then we did another call. Then it was another call with the president of Harpo and the director of HR. Yeah, so that’s, that’s, that’s how it came to me. Do you want me to continue?

Jeremy Burrows 21:50
Yeah so I want to, I want you to tell that’s, that’s awesome. I want you to tell about the interview. And kind of what how you were honest with Oprah and just kind of laid it out how it happened. Instead of trying to just like, oh, you know, I’m gonna be professional. And I’m gonna, you know,

Libby Moore 22:09
yeah. So, so that’s how it came to me when I you know, I released it. And I wouldn’t call it giving up on my dream. Like a quitter. I just released the dream because it wasn’t working out. And I thought, Oh, the universe has a bigger dream for me like Oprah, Oprah would always say, the universe, God, or the universe has a bigger dream for you than you can dream for yourself. When it’s not working. If you’re going for your dream, and it’s not working, then there’s something bigger waiting for you, outside of what you think it is. So. So that’s, that’s why I wanted to tell the details of that when I released what I thought was the right thing for me. It it opened a space for something phenomenal to come in, which was the opportunity to work with Oprah. So after a series of phone calls, which lasted about a week, the President of Harpo and the Director of Human Resources said, Oh, Oprah is going to be in New York next week. Can you meet her at such and such a hotel for meaning for an interview? And I said, Yes. So I got to this hotel early. And I found a quiet space in the lobby. And I sat down, and I said this prayer, and I said, you know, thank you, thank you, thank you for this opportunity to meet Oprah Winfrey. Wow, like, This is crazy. This is amazing. And if I am meant to have this job, make it clear to her and make it clear to me and if I’m not meant to have this job, well, thank you, thank you, thank you for this opportunity to sit and meet Oprah like that. That was it. So it was a win win. In my mind, it was I was giving gratitude for what was about to happen, regardless of the outcome. And I also said this, set this intention, thank you for flowing through me and helping me to be calm, cool, and confident and 100% myself. And I do believe that words have power, intentions, have power, prayers have power, it’s all the same thing. So I don’t want people to get confused, like shut down. If they don’t call it God. Stay open to whatever it is for you call it energy, it doesn’t matter. Because the lesson in it is what’s important. So I went in to the host station, they said I was the first one there. I sat at this reserved table. It was it was like Friday, Thursday. I think it was that Thursday or Friday. I can’t remember bustling with people. And then Tim Bennett came in the president of Harpo and said hi, I’m Tim Bennett and we spoke on the phone last week. Oprah is on the phone with President Clinton. She’ll be right down. So yeah, I was just like, wow, this is amazing. And I just had this Flash in my mind of oh my god, you know me, little Liddy Moore from Berlin, Maryland population 3000, you know, failed typing in college, my parents weren’t even sure I was gonna be able to graduate from high school with my grades. You know, I’m about to meet Oprah Winfrey, and she’s on the line with President Clinton. It was just a really amazing moment. So Oprah came in and introduced herself sat down, Tim and Miss Winfrey, I called her Miss Winfrey room at the time. We were all talking for about 35 minutes. And I remember at about 40 minutes, she said, Okay, so what’s your plan? And I said, What do you mean? What’s my plan? And she said, What’s your plan? What’s your plan for your life? And in that moment, Jeremy, I had that moment of like, Oh, do you say what you think you should say in an interview with Oprah Winfrey? Or do you tell the truth and in that nanosecond of thought I went with the truth. And I said, Well, you know, like, five weeks ago, I was, I had been sending writing submissions to the head writer at Rosie O’Donnell, I never got a reply. I said this prayer on the subway, Okay, God, God, clearly, you don’t want me to work there, whatever you want me to do every atom selling molecule and my body, mind, soul and spirits open to it, show me what it is be clear, and I’ll do it on then I released it. And then here I am five or six weeks later sitting here with you having a glass of Chardonnay. So if you leave this interview, and you feel that I’m the right one for this job, then I would be honored to take it because it would match my seven years of experience as an executive assistant with what I’m passionate about. And what I’m passionate about is what you’re doing on your TV show with your foundation, helping women and girls throughout the world. So it would be just an honor to take that job. But if you leave this interview, and you feel like oh, she’s nice, but I don’t think she’s the right one for the job. That’s okay, too. Because that means there’s a better chief of staff coming for you like a better fit, and they’re coming right around the corner. And for me, you know, if this isn’t what God has planned for me, I cannot wait to see what’s next. And we just kind of held eye contact for like, a beat or two. And she looked at Tim and said, Okay, Tim, let’s bring her to Chicago. And you know, Tim was like, whoa, whoa, let’s slow this boat down. Because he knew, you know, we need to slow it down. He said, Why don’t we bring Libby out to Chicago to meet our folks. And that’s exactly what I did. I went out there, I had meetings with people at Harpo from 6am to 6pm. And when I went back to the airport that night, I went into a bathroom stall at Chicago, Chicago O’Hare and I just started crying. Because one I was exhausted from, you know, the interview process just being on and, and it was really intense. And too because I knew I was going to get that job, am I and I knew that my life was about to change dramatically. And I just kind of had this moment in the bathroom stall of like, oh my god, this is the most exciting thing. And the most I think there was little like sadness in it. I knew I’d be living in New York and my friends and my partner, you know, there, there was like, a lot mixed into it. So that’s, that’s how I got that job.

Jeremy Burrows 28:31
That’s great. Well, thanks so much for sharing that. All the all the details that kind of behind the scenes that people think, oh, you know, you just got the job and whatever it’s like, it’s, it’s so refreshing to hear kind of the real, honest, authentic version of the story. So I appreciate it.

Libby Moore 28:50
I love that you said that. Because, you know, I could say, oh, I got it through a recruiter in Chicago and did that. But if I don’t share all the little nooks and crannies of it, then people won’t be able to relate how it relates to them. Because that’s how we’ve all like I could say, how do you start your podcast? How do you get the job where you are right now? And that’s where like the magic is in the behind the scenes and the details of how did it come to? what was happening before it came? How did you feel about your current job or were you not working and and how did you create this energy to draw to you an energy that matched where you are right now? So I love telling the details. I think the the lessons and the magic and the golden nuggets are in the details.

Jeremy Burrows 29:36
Yeah, it’s it’s funny, I you know, just think about my transition to my current executive and it’s just like I had worked with a guy, longtime friend. He was my youth pastor when I was 12. I ended up being his it’s funny. I ended up being as an executive assistant for six years or so. And at one point his his wife was Like, hey, you remember when you were 12 and we went to summer camp, and you would always come up to me, and this is my former executives wife, and ask, what are we doing next? Where were we going now? What are we doing next? Wow. And you know, 20 years later, they were they were coming to me saying, Where are we going next? What are we doing next?

Libby Moore 30:24
Wow, I love that.

Jeremy Burrows 30:27
So anyway, just

Libby Moore 30:28
interesting. Right? Yeah. Just crazy. So

Yeah. full circle moment.

Jeremy Burrows 30:35
Yeah. So let’s talk a little bit about while you were in that role, with Oprah, obviously, pretty high profile role. Have you experienced what I call dehumanizing interactions with people, specifically, when you’re in those higher profile roles? In other words, did people try to get close to you? In order to get close to Oprah? Or did people befriend you and then later, you realize they were really just trying to get the inside scoop on Oprah? Does that make sense?

Libby Moore 31:10
Oh, my God, Jeremy 100%. I love that you were asking this question. No one’s ever asked this question. And in my own mind, I’ve kind of thought, why don’t people ask this question? Like, you know, it’s so interesting. So I wouldn’t. It’s interesting, I wouldn’t. For myself and my own experiences, I wouldn’t use the word dehumanizing. And I also think I’m a little naive. You know, like, I’m always, I always really expect that people like trusted people are good until they show me otherwise. I’m, so to answer your question. There were some people that energetically I could just feel they’re being inauthentic. They’re trying to befriend me to get a connection with Oprah, which anybody who knows me like in that role, I was like, the moment I went in, I was just like, very hardcore with my boundaries around, you know, asking anything of her number one, like rarely, I mean, when my mom came to the show, I don’t know how many years and I was like, I really, you know, I never asked you this, um, you do not have to do it. My mom is here, she’s going to be in my office afterwards, if you would like to come in, it would mean a lot to me. You do not have to, you know what I mean? I was so where most people are like, hey, Mom’s gonna be there, will you come in and say hello. Like, I was so hardcore with my boundaries around protecting her, Miss Winfrey and our time and our space. So and I was very, like, my, my personal life was my personal life. And they were all my friends. Be Oh, before Oprah. You know what I mean? Like, that’s all I had time for. I didn’t even really have time for new friends. So it’s like, if I had time I was with the people that knew me before I got that job. But I was in Chicago for 11 years. So I will say that there were maybe two people that I that I really thought were like, really good friends of mine, that later either said something or did something. And I realized, oh my god, this is all about them wanting to be in alignment, or one step closer to Oprah, which made me just feel icky and gross and sad, because I really didn’t think that was the case. And then there were some people at work that that were really were my great friends and still are today. And then some people who I thought, Oh, this is like a friend. And in hindsight, I’ll just stay away from the details. I realized, oh my god, this was all about them getting ahead. And it was super, They weren’t close friends of mine, but in hindsight, it still hurts you know, like, oh, man, I thought they really liked me, but it was really about them getting ahead. So yeah, I did experience that and because I think I’m I was more naive, and just trusting that I didn’t see it when it was happening.

Jeremy Burrows 34:17
Yeah, I honestly didn’t see it really when it was happening for a long time either. It’s just now that I’ve kind of come out of my former situation and just reflect spend some time off and reflected on it that I really saw the damage it did to me like emotionally. Yeah, just just helped contribute to my emotional closure, if you will, or just my lack of wanting to be vulnerable because I was I used to be pretty vulnerable and then you know, when it burns you so much that it’s hard to it’s hard to open up again. So once you realize that Was there anything that you maybe took away from that realization? To kind of like, like I just said, for myself, I kind of shut down emotionally to be honest, which isn’t necessarily a healthy way to deal with it. But, yeah, was there something that you did to kind of prevent that from from happening again, or something that you would encourage those listening who are currently experiencing that?

Libby Moore 35:28
Well, I think that if you’re, you’re in it, and you’re experiencing, like, Oh, my God, this person, I thought they were my friend, but they really just want to get ahead or they want to get to Oprah, then you can manage that yourself like, Okay, I’m going to pull back because I realized this isn’t what I thought it would be. So so it depends on the situation. But I would say for me, what’s interesting is, because I left eight years ago, and as you know, from hearing me in Atlanta, I took that year off or did the Libby Moore gypsy tour 365 days of following my heart and then I ended up getting my coaching certification to life coaching and then went into executive coaching and then launched Love X Global, which is bringing the energy of love back into business. And the the irony of what did happen with me where people may be, well, where people did use me to get ahead. I am more open and more loving, and more open to receiving love than I’ve ever been in the past eight years. So it didn’t, I understand why it would close you, and I would say every day, you know, take that step to open back up because that’s them stealing a piece of you. That’s not you, you are love we’re all love at the core meaning energy, this beautiful, brilliant positive energy. And there’s so many little things that nick away at that, but we cannot let it close us down. What the world needs, It’s such a cliche, is love. That is really what we all need. So we cannot have people like you, who is such a beautiful person with a big, beautiful heart to close that down at all. You must continue to open it up. So I would say that’s what I got from it. Honestly, it didn’t. In the moment, I was like, Whoa, that’s weird. And and I did hibernate for a year. I mean, my partner and I at the time, did a road trip up the west coast from LA to Seattle to visit friends. They said hey, this cute little college cottage came out for a for rent, they never do. We looked at it. We loved it. We rented it for a year. So I went from Chicago, 11 years, Santa Monica, California four months while helping launch Super Soul Sunday on the Own network. And then when I left, it was like road trip. And now we’re in a cottage on a lake in Seattle. And I know nobody but two people and my partner. So I think that maybe was my healing time. You know, from all of that, like I wanted to get out of LA I didn’t want to be near entertainment. It wasn’t a bad thing. I was just like, done. You know, I was like, I need to get back to myself and figure out who am I now if I’m not Oprah’s chief of staff?

Jeremy Burrows 38:05
Yeah, that’s yeah, it’s very, very similar to my situation where I took like, seven, eight months off, traveled, sold our house sold our, most of her stuff, or gave it away and travelled the country with our two boys. And yeah, it’s just kind of rediscovering my myself and nature and God and family and just kind of hitting reset on life.

Libby Moore 38:33
Yes. Wow. I didn’t know that Jeremy.

Jeremy Burrows 38:36

Libby Moore 38:37
I love that.

Jeremy Burrows 38:39
Yeah, it was a fun little, fun little trip once I kind of had that couple months to decompress and reset a little bit. And then we’re like, alright, let’s sell our house and let’s just simplify our life. And yeah, so anyway,

Libby Moore 38:56
cool. kindred spirits.

Jeremy Burrows 38:59
Yeah. So let’s talk about assistants for a couple minutes. If you could snap your fingers and instantly give all assistants, more of something, what would it be?

Libby Moore 39:10
Self Confidence.

Jeremy Burrows 39:14
What do you think is the number one reason assistants lack self confidence?

Libby Moore 39:22
It starts in childhood. I mean, as a coach now and coaching people for the past seven years, I get, realize, oh, wow, I’m not the only one. You know, you know what I mean like coaching men, women, young, old, rich, poor, unemployed CEOs, international companies. You know, it’s, it’s fascinating because when you do therapy, you’re just talking about yourself and you’re like, oh, maybe share it with a few friends. But you just kind of think you’re the only one but then when you get on the other side, it’s like oh, wow, everybody’s pretty similar. Yeah. And, and it’s that whole lack of self worth. There’s kind of like three core things. it’s I’m not worthy. I’m not lovable, fear of abandonment, you know, and those translate into lack of self confidence. And I mean, based on my own experience from working with people, every human being walking the earth had some trauma happened to them between the ages of zero and about 13. We could even scoot it up to 15. But usually it’s zero to 13. That’s where the trauma happened, whether it was, you know, you’re sexually molested, or you your parents got divorced, when you’re young, and some core part of you thinks it’s your fault, which it’s not, you know, did there’s there’s a billion things that we could list off in that area, where that seed of I’m not worthy, or I’m not lovable, started. And then when little things would happen to reflect that seed of thought, I’m not worthy, I’m not lovable. See, I, my teacher doesn’t like me, that’s because I’m not worthy, or I’m not lovable. Anything that comes to feed that false belief, it just becomes bigger and bigger and stronger and stronger. And I think that as assistants, we most of us get our value by being able to take care of other people. And even if those people don’t, don’t appreciate it, or don’t say thank you, it’s just like giving, giving, giving, giving, taking care of people supporting them, that gives us value we’re like, and again, I’m speaking in a very broad way, it’s like, I’m going to make myself indispensable. And the more that feeling of I’m not worthy, the deeper that is, in some cases, in some cases with people, the more indispensable they make themselves, almost to the point of being sick, where they’re working around the clock, they’ve put their entire personal life on the back burner. You know, it’s like, there’s never, they can’t do enough in this role. So I think there’s an element of people that take on this type of role of at the core that might be like, I’m not worthy, or I’m not lovable. And I mean, that’s a pretty bold thing to say, but based on my experience, my own personal experience, number one, and with all these people, I’ve worked with not just assistants, but even CEOs and all kinds of people. So many people have that, that thing. So if if you could wave the wand and people would have self confidence, maybe self worth, actually, that’s even better self worth the Self confidence is a byproduct of healthy self worth.

Jeremy Burrows 42:42
Love it. One other thing I would love you to share if if you don’t mind is the story about the janitor. Oh, yeah, I love I love that story. I’ve always, I don’t know if I learned it from, I think I learned it from my former executive, he was really good at this. And then my dad was good at this as well. Just always like being kind and talkative or sociable with, with whether it’s a janitor or cashier or the person, you know, washing your car or whatever it is, like, just treating them with respect and dignity no matter what their title was. You know, you told the story, that agenda that I’d love for you to share real quick, if you don’t mind.

Libby Moore 43:28
Sure. Happy to. I love this story. So so when I moved to Boulder, Colorado at 23, I was there for two years again, do it, I thought I’d go for years ski and then move on to New York to do the Saturday Night live thing. But it ended up being two years and you know, doing all kinds of odd jobs. And at one point, I was a receptionist at REMAX of Boulder answering phones and then at night, I don’t think it was every night but let’s say two or three times a week, maybe it was, it probably was every night actually we would go in and I would work with this cleaning crew that would go into this big building called it was called the US west building which doesn’t even exist anymore like a big a&t type phone company. And I think we went in from 9pm to about 10 11 Maybe like eight to 11 something like that. And we would be the cleaning crew 12 of us we break into six groups of two people and it was you know, mopping the bathroom floors emptying the trash cans, cleaning everything and then in the office spaces vacuuming empty trash cans, dust the the computers and desktops. That was it, boom, boom, boom. And so one night, I was in the Executive area and there was this woman in this glass office, obviously a high level executive and she was working late. I think it was around 10 10:30 At night, and her door was shut and I went to her door and I knocked on the door and opened it and said Excuse me, may I Empty your wastepaper basket. And she just snapped and was like, Who do you think you are knocking on my door when I’m in here, I’m a very important person. And when you see me in here working at night, you, you do not come in. And I was just shaking. I was so shocked by her outburst. I was shaking, you know, just shaking. And I said, I am so sorry, I apologize, it won’t happen again. I shut the door. And as I turned, this thought crossed my mind. And I really want to slow down on this part of the story. It wasn’t like I thought, well, someday I’ll show her. Not at all. It was a thought that just like whizzed through my my mind in a couple, a second two seconds. And the thought was, someday, you’re going to be a big executive working in a glass office. And when the maintenance person comes in, and you’re gonna stop, look them in the eyes and ask them how their day is. Boom, just like that. Like, through my mind, that’s it. I didn’t think about it. As I continued cleaning, it was just a thought that passed through my mind. I was 25 years old when that happened. 10 years later, really, nine years later, I’m now 30. Oh, I was 34 35. And I’m Oprah Winfrey’s chief of staff executive assistant. My office was glass. It was like, you know, one whole wall was glass that looked directly across the hall to her office. And I remember, you know, that first year, I would work until my god anywhere from 10 to midnight, just trying to get my head around the enormity of this role and trying to figure it all out, and what was I supposed to do? And I remember, the first time the maintenance guy came around, his name’s Billy Adams. And he would, you know, come in and say, excuse me, hi, you know, I’m Billy. I’m the maintenance guy, or whatever. I’m Libby, hi, we met each other. I was like, how are you doing? And we would chat. And he would always be that, you know, coming around at night. And I’d always say it wasn’t even like, Hey, here’s the guy. Now I got to do this. It just came naturally. And I would, you know, say, how are you? How’s your family? How’s it going? And so again, it didn’t occur to me the first time he came in, it wasn’t until later I thought, Oh, my God. I remember when I was a janitor in Boulder, and that woman yelled at me. And I had that thought that someday I’m going to be an executive in a class office, and you’re going to stop and look this maintenance worker in the eyes and ask how they are. So to me, that’s extraordinary. How did I know at 25 years old? When I was working two jobs, you know, janitor night that? How is who is going to be an executive and an office? Like what? I don’t think so. You know, it just it was so bizarre. And what’s interesting is that for 11 years while I was there, and working late, and Billy would come in, and we really created this lovely friendship, and he would confide in me with certain things or like, really, he helped his team members in ways they will never know. He was phenomenal. And I also realized, in hindsight, he was a prophet that was coming in because when I would complain about the weather or the workload or things like that, I would say, Well, how are you doing? He’s like, I’m good. Libby. I got I love my wife. She loves me. All of our kids are healthy. I love love, love my job. I’m so happy to be working here for Oprah and at Harpo. I’m good. God loves me I’m good. He would say that every single time I asked him so what he was doing he was like that beautiful prophet in disguise in a way telling me over and over this is what’s important Libby, your health your family a job you love being grateful for what you have. So yeah, I just you know, there’s so many prof prophets in disguise if that’s the right word messengers is probably a better word all day long throughout the day waiting to deliver a message for us if we’re open to hearing them. Yeah, that’s the Billy story.

Jeremy Burrows 49:29
Awesome. Well, your your Billy story pretty much could be the answer to this next question, but I’m gonna ask it anyway because you version but my last question for the interview is what makes an assistant a leader?

Libby Moore 49:49
I would say it’s two things. It’s being 100% yourself at all times with all people and all situations to the best of your ability, because that’s going to change day to day. But that’s it really is like being yourself. And being the leader, that you would like your manager to be. Being the leader that you would like to do the things, say the things be the things that you would like your co workers, your manager, your boss to be, especially coaching, I hear so many people complaining about how their manager or their boss doesn’t do this. The question would be are you doing in that? How are you doing that in your life, personal life in your professional life? And how are you managing up? How are you helping that person to be a better version of themselves? Yeah, that’s it.

Jeremy Burrows 50:45
Love it. Well, Libby, thank you so much for again, taking time out of your day. It’s been a great, great conversation. I love hearing your stories. Where can people find you online? And how can we support what you’re up to?

Libby Moore 51:02
My website is, which I have not updated in all honesty in probably five or six months. So now that I’m saying that on your show, I’m going to go in and update that. I’m on Instagram, it’s Libby Moore gypsy tour. And I’m on LinkedIn that that’s it. Now I’ve never been on Facebook or Twitter or anything else. That’s where I am. And I would say that anybody that’s interested in having me come to your company and do a talk or coaching or bring love x coaching into the workplace, which is bringing the energy of love back into the workplace. I would love to do it reach out to me. I’d love to have a chat with you. And Jeremy, thank you. This has been so fun. It went way too quick. Maybe I talk too much. I’m open to a part two anytime with you. So thank you for inviting me. I really appreciate it, Jeremy.

Jeremy Burrows 51:59
Awesome. Well, you’re welcome. And yeah, thank you for being on the show. And we will. Yeah, we’ll see about a part two later.

Libby Moore 52:07
Thank you. Thanks, Jeremy.

Jeremy Burrows 52:09
Well, thanks again, Libby for a great conversation. Please do check out the show notes at That’s, and reach out to Libby connect with her on LinkedIn. Follow her on Instagram. And if you’re interested in the exclusive preorder bundle for my new book, go to to talk to you next time.

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