Lean Out with Bestselling Author and Leadership Speaker, Marissa Orr

In this week’s episode of The Leadership Habit podcast, Jenn DeWall talks to Marissa Orr, a former Google and Facebook executive, bestselling author, and leadership speaker. Spending 15 years working at today’s top tech giants, she’s conducted talks to thousands of people in the US, Europe, and the Asia Pacific at companies and universities such as Google, Twitter, Pace University, New School, American Express, and more. In this exciting episode, they discuss Marissa’s book, Lean Out: The Truth About Women, Power, and the Workplace.

Full Transcript Below

Jenn DeWall:

Hi, everyone, it’s Jenn DeWall. In this week’s episode of The Leadership Habit, I am so excited to be talking to former Google and Facebook Exec, leadership thought leader, author, podcast host, Marissa Orr. Marissa, thank you so much for joining us on the podcast today.

Marissa Orr:

Thank you so much for having me. I’m excited to chat.

Jenn DeWall:

Yeah. Well, first of all, let’s just go ahead and do that introduction. I know some people obviously heard a little bit about you from our intro, but they want to hear it from you. Tell us a little bit about yourself, maybe what you do and what you would want to share with the world, or I guess what inspires you?

Meet Marissa Orr

Marissa Orr:

Well, I was born on a warm summer day now. No, just kidding! So I am, I worked in the corporate world for 15 years, and people are sometimes surprised to hear me refer to Google and Facebook as corporate because they do kind of have this very progressive, like new wave image of companies. But they were very corporate, especially Google toward the end. So I worked there for about 15 years, and then in 2017, after leaving Facebook under extremely strange circumstances, which I detail in the book, I decided to start a whole new career and devote all my time to pursuing my dream of helping women and speaking and writing full time. So I now do that.

I live in New Jersey with my three children. I’m a single mom. My older son is about 12, and my twins are 10. And I’m originally from Miami, Florida, which right now my background is very academic looking on purpose so that people take me seriously. You know, it’s lined with Finch trees, but right now, I am on a little bit of a beach vacation. So it’s reminding me of home. I am on the beaches of Delaware. So yeah. Good stuff.

Jenn DeWall:

That sounds so lovely for those that may not know you wrote the book Lean Out. I have really loved the book. It’s something that I feel like really spoke very much to me and some of my philosophies, but what inspired you to write that book?

What Inspired the Book, Lean Out?

Marissa Orr:

A few things. One, I’ve always been very passionate about the topic of gender and women women’s issues. And so back in 2013 or 2014, around the time Lean In came out, by Sheryl Sandberg, it really ushered in the space of programs, workshops, and leadership initiatives at Google that were really aimed at helping their female employees succeed. So one thing that book really deserves credit for is bringing this conversation really to the forefront of so many companies and having so many resources devoted to women and its and its weight. So that happens at Google, and I, of course, attended everything because I was super interested and passionate about this topic. But after a while, I became really kind of disenchanted, I guess, is the word because the conversations never resonated with me. I couldn’t identify with the female leaders they chose to talk to us on stage. I just didn’t connect with them. I felt like the challenges of being a working mom, there wasn’t a lot of honesty in the conversation, and the advice wasn’t really practical.

And I just felt like we were getting something wrong. And so, I started to write my own perspective on the topic to deliver as a presentation, which eventually grew, and it served as the basis of Lean Out. But I wrote this book to make women like me feel heard and understood because I never heard anyone talk about my specific challenges or my journey. And I felt like something was maybe wrong with me. And after a while, I realized there was nothing wrong with me, but there are no voices like me talking about, you know, the things that I care about or are concerning for me. So I wrote this to make other women feel heard and understood by giving those stories and challenges of voice. The other, the other reason I wrote it, I really wrote it.

I wrote the book I needed to read when I was starting out in my career because I spent the first ten years of my career really not understanding what game I was playing. I thought it was one thing, and it wasn’t, and it took ten years for me to really understand what that game was. And I wish I had known that when I started, I would have played it very differently. Not because I felt like I would have played it better and gotten to the top. I would have taken it for what it was and not have invested so much of my self-worth into my work, knowing that, you know, it’s just, I always felt like around a square peg in a round hole. And so I didn’t know why. And I think this book really is sort of like my Mea Culpa, understanding the world that I was operating in. And like I said, it was the book I needed to read starting out.

Jenn DeWall:

Yeah. I feel like it’s the book that I also needed to read when I started out. I think, you know, when you’re an early leader, I don’t think college prepares you to consider things like emotional intelligence. You might know what it is from a textbook, but you don’t really know what it is as it relates to politics or you’re your own executive presence or when you can speak or not speak as a really, as you know, in relation to that culture. And I think why your book resonated so much with me is that my first job out of college was a position at a huge corporation. And I would say it offer it operated. I mean, it was a huge company like the corporate culture, but if you went against the grain, if you didn’t fit their mold, then you were kind of deemed an outcast. And it felt like the worst feeling, especially for being such an ambitious person and wanting to do these things. But I, I felt like, I mean, if I gave you an example from mine and I know our listeners have heard this before, but I got feedback that I needed to be more of a yes, man. That’s, you know,

Marissa Orr:

That’s actually surprising that they were so honest with you about that because a lot of times, no, I’m serious. Because a lot of times people get dinged for that, but it’s not said as honestly, is that because, you know, you’ve got to fall in line, that’s the structure of the organization.

The Confidence Gap Myth

Jenn DeWall:

But it’s, we know we know today there just aren’t enough voices, I think. And I think we’re seeing more like more voices come in and talk about this different perspective, this different way to really create an inclusive culture. But I still think we, you know, we kind of just tend to go with the flow like, Oh, this is what it’s supposed to look like. So I’m just going to follow these rules instead of saying, should we look at changing the rules? So we’re going to be talking about a few different chapters from your book, lean out, and you know, you hit the first one, and this is what we’re going into. We’re talking about chapter three and The Confidence Gap, which you even touched on it briefly how we attach our self-worth based on the title that we have, the organization, and the prestige of that organization that we work for. But let’s talk a little bit about the confidence gap because this is something that even on our show, The Leadership Habit, we don’t necessarily always bring it back to self-worth, even though it’s incredibly essential to how you’re going to lead your organization, your team and yourself.

Marissa Orr:

Yeah. So this, the chapter you’re talking about really debunks the myth that men get ahead at work because they have more confidence than women. And I feel like the conversation is changing because I feel like saying that today is actually a little more provocative than it used to be. Even it was kind of accepted, you know, following Lean In, and that the conventional wisdom of the day about men having more confidence in women, wasn’t seen as something provocative to say, but now maybe that’s changing. But anyway, I really debunked the myth in that chapter by explaining, like starting with, what is confidence really, right? Because when we, a lot of these, right, these authors or speakers or executives that make that claim, because a lot of researchers do as well. And they make the claim that men have more confidence. They really aren’t defining confidence very clearly.

And it actually seems that their version of confidence is the ability to think- you really think that you’re great. So they refer to research that showed that men and women were given a test on scientific reasoning. And before the test, they were each asked, what do you think you, how many do you think you’re going to get? Right. And the women let’s say, I don’t remember the exact numbers, but you’ll get the gist of what I’m trying to say. Let’s say women said, I think I’ll get six. Right. And men said, Oh, I think I’ll get eight. Right. And it turned out that they, you know, an average, all got seven right. Or something. And they use that as evidence to say that women are less confident and that we should be more confident in ourselves. But actually, that’s not what confidence is at all. First of all, they use research that focuses on these really specific themes, like scientific reasoning. Right? Well, I mean, I don’t know. Maybe I would put myself worse on scientific reasoning. Changed the topic, and I more quote-unquote confidence, but that’s a whole other issue. Really.

But the point really I was making is that the definition of confidence is really having a realistic assessment of yourself. It doesn’t mean it should be overinflated and it shouldn’t, it doesn’t mean it should be lower than what you actually are. It’s an honest relationship to reality and an honest relationship with your strengths and weaknesses. In other words, it’s a lot about self-awareness. And when we’re aware of what we’re good at and what we’re bad at, and we can own our strengths and own our weaknesses without having this insecurity to try and, you know, make up for them, that’s really rock hard, solid confidence. And when we say men have more, what we’re really mistaking is the arrogance and bravado for confidence.

So that is not something I think that we should be holding up as a value in society is overconfidence. And it’s confusing because overconfidence and confidence are not exact. If the wording is, it is really confusing, but overconfidence is this tendency to be blind to reality. Think that you’re amazing and the best. And when you have that sort of attitude, you’re the person that’s always talking in meetings. You have to talk over everybody else. It’s, it’s bluster, it’s bravado. And it actually stems from insecurity in the same way that somebody who’s overly timid and doesn’t own all the great things about them. And always trying to cut themselves down to make others look, you know, that’s also a result of insecurity. So bravado and sort of this inferiority, they both stem from insecurity. They just manifest these different behaviors. True confidence is really owning who you are, and that’s really the definition. And as far as I know, I did so much research. There are no studies. There is no research that using that definition shows that men are in any way more confident than women. The problem is in the corporate world. We reward bravado. We reward arrogance, we reward these behaviors and then call them confidence when that’s not at all what they are.

Is it Confidence or Bravado?

Jenn DeWall:

Gosh, I think it sounds like almost the reliance on the notion that perception is reality. If you look like you are the part, wearing the nice attire, or you drive in, you drive the fancy car, or you have XYZ, that you have what it takes.

Marissa Orr:

It’s an image. It’s image and perception. And look, that’s the way that world works. I’m not taking a sort of a moral position on it. What I’m saying is let’s just all be honest about what that world requires of people in order to advance, instead of pretending that, you know, it’s a meritocracy where, you know, the best employees, the highest performers are the ones that get promoted and that this world works in any sort of rational way or that what should happen does happen. It doesn’t. It’s you know, and again, I’m very passionate about this. I can go on forever. So I’m not taking, I just want to make the point not saying, Oh, from a moral standpoint, it’s wrong that, you know, that bravado is rewarded. I’m just pointing out that we’re not honest about that.

Jenn DeWall:

Yeah. And that we need to also look at ourselves instead of maybe comparing ourselves to that bravado and using that as an aspirational goal, that we’re looking at ourselves, what value can I bring to this?

Marissa Orr:

Right. And my problem was always that we take these traits like bluster and hold it up as a benchmark and say, well, when you act like this, you get promoted. Well, it doesn’t mean that we should act that way. And everybody has to make that decision for themselves, of course. But you know, the benchmarks were just, they made no sense to me. We were holding up like certain qualities and values that I don’t know. They, they were just never me.

Jenn DeWall:

Yeah. Well, and I think that it’s actually not a lot of people. I think we never felt like we could actually share that though because if I speak from my own experience, it was always kind of, I think the comfort that I got in terms of being a young person in the corporate culture is that using that did help me, you know, determine my roadmap, but help me determine my career trajectory. It was, you know, that was the aspirational goal. But the thing is there’s so much going into that, that it’s not really attainable because so much of it is rooted in, in that perception versus it’s not, you know, whether or not you’re adding value, it’s kind of the pomp and circumstance of it.

Marissa Orr:

Yeah. And if that, if that appeals to someone, like more power to you, you know, I just was thinking that it was the game was something it wasn’t. And had I known that that’s what gets rewarded and that’s what makes you a manager. Maybe I would have played the game differently. So yeah,

Jenn DeWall:

But we have to note for like our leaders here. It’s got to start with you, you seeing your value, you understanding how or what you bring to the table. And also the areas that you can ask for support. So, you know, I think in that same type of culture, you then feel like you have to do it all and you can’t do that either. And that just further creates a gap in your own confidence.

Marissa Orr:

Exactly.

Lean Out – the Power Reward

Jenn DeWall:

So in chapter seven, you know, you’re talking about in Lean Out you’re talking about The Power Reward, and its kind of based on the notion that we want to get promoted, or we have these aspirational goals because we’re seeking positions of power. And tell me more about that. Like where, what inspired you to say that and kind of debunk that notion that that’s what everyone wants.

Marissa Orr:

Yeah. So it started, I start that chapter with this story about a personality test that I did in an offsite at Google. And we all were given like one of four colors to represent one of the four major personality types. And I was a Green, which meant that I have a strong drive for harmony. I prioritize, I have a strong drive to help people. I strive for harmony, and I prioritize my relationships. And the opposite of green, by the way, because it was like a very hippie one. They called it Forest Green, and then the opposite was red. They called it Fiery Red. Reds are competitive. They strive for power and control, and they prioritized results over Greens like me, who prioritize relationships. And then when they asked us to get in groups by color, this question, I just blurted out loud. It’s really. It was ended up being a tremendous insight for me on this journey to understand what’s going on at work. I asked, “what are the colors of our senior executive team?” And the HR person running exercise she didn’t want to answer it, but then everyone’s so curious, and it turned out nine out of 10 were obviously, but do you think Red or green?

Jenn DeWall:

I mean, I’m a Green, so absolutely not a Green?

Marissa Orr:

Yeah. They were Red. So nine out of 10 were Reds, and then like the 10th was like a Yellow or something or whatever. And it was a tremendous insight for me at the time around motivation because you know, what is the reward at work? Well, every raise that you get incrementally becomes less satisfying because it’s a smaller percentage of your base. So a 25K raise when you’re making 50K years life-changing. Right? But if you’re making 250K, it’s hard for money to be like the thing that’s pushing you to work harder and harder. And so many people in the corporate world are very comfortable. They don’t need more money. So like what, what motivates people to want to get to the top? Keep climbing, pushing every day to work harder. Well, what comes with the promotion? Money and power, more power over more people in the form of being a manager, right? Now, if you’re a Green like me, having formal authority over people like that is not only unsatisfying. It can be uncomfortable because authority and relationships are in tension with each other, and everybody’s more motivated by one or the other.

So the example I always use is let’s say you’re on a team with two of your best friends and you’ve been on this team together for years, and then suddenly you’re promoted to be their manager. And let’s say you like to flex that position of authority. You know, you’re like, I’m the boss lady now, blah, blah, blah. What happens to your relationships? They suffer. Right? But what happens if you act like nothing’s changed, you’re still their best buddy. You know, you’re talking crap about your coworkers with them. Not that I would ever do that, but I’m just, you know, saying. Well, what happens in that case? Your authority is undermined. And that’s what I mean by relationships and authority are in tension with each other. And everyone’s more motivated by one than the other. Now the issue I’d begin confronting in my career at Google at the time was I was an individual contributor by choice.

And in order to get promoted to the next level, I had to start managing people. And I, I didn’t, I just didn’t want to be a manager. I really didn’t. But I was, I didn’t want to be honest about that with my manager, because I knew it would be seen as like, Marissa lacks ambition. Or, you know, I wouldn’t be taken as seriously. But through the lens of color, suddenly, I totally understood this in a brand new way, which was, I mean, I’m just simply not motivated by positions of authority. I’m more motivated by creating connections, relationships. Like I always want it to be a coach or a mentor, but never an official manager. So I was pretty naive. I brought these new insights, my manager thinking, Oh, she’ll totally like understand that this is an issue with Google, not me. Like they should. I mean, everybody likes different things.

This is something we learned in kindergarten, and we teach our kids so naturally, she will understand that. And not, you know, that management will be more of a punishment than a reward, and I’ll get exempted from this policy. That was my thought. And she was great about it. But she said that despite having heard all these arguments before, our VP was adamant about the fact that you needed to manage people to grow your career. Now, when that happened, I was really dumbfounded. I was like, why wouldn’t they want to keep their best performers and keep them happy, being motivated by giving them something they actually want. And so something they don’t want.

But with time and experience, I really started to understand and learn, but no business book ever told me. And that is what I saw as a simple difference in personality. Other people saw it as a weakness, and it was a huge insight. It just never occurred to me that that’s how that, that’s why the perception is what it is. It’s viewed as a weakness. And a lot of people will ask me, how did you not like know that it’s just, you know, better late than never just took me a while to understand how other people looked at these things. And you know, really kind of taught me that- and it was very obvious working in the corporate world that a certain kind of person is the person that advances to the top. It’s, it’s a really narrow profile of personality traits. You don’t see, you know, hippies as the corporate CEOs. There’s just- you just don’t, you don’t see it. But it doesn’t mean that I lacked ambition. And that was really the point I was making in the power reward, which is relationships are a huge form of power in this world.

I mean I, and I go into this whole thing about Bonobos, which are female-dominated societies and their primates and they, their currency is relationships. Whereas, like apes, which are chimpanzees, which are male-dominated, their currency is brute strength. So my point is both are a form of power. And if you’re more motivated by relationships, that doesn’t mean that you can have any less of an impact in this world. It just manifests differently. And I think a lot of women- this framework helped a lot of women understand themselves better. And at least that’s what the, you know, the messages I get. So hopefully, that was a long-winded explanation, but it’s worth giving the details to really fully understand what I’m talking about.

Differences not Weaknesses

Jenn DeWall:

Yeah, no, I think that this is such an important thing. That’s a topic that’s not talked about very often because it is so accepted to say your natural career trajectory should include leading a team. And then you have organizations that say, this is the expectation for that but in the air and the era today where I think many companies are really facing that talent scarcity where they can’t get the right people, why risk losing them by forcing something that’s not in alignment with their values or their personality or their aspirations? And they can still have that. But I think you’re bringing up a really strong conversation that actually needs to happen in many organizations because they’re in some way, by having that expectation that people need to do that. They’re then not respecting the art of leadership. That actually is a really difficult skill set that not everyone is very communicative or empathetic or meant to be a great leader, but they could be lovely, like an individual contributor.

Marissa Orr:

Yeah. Well, there’s a difference between leader and manager too. And I think we’ve conflated those terms to the point where, I mean, we use them synonymously, but they’re not the winners of the corporate game are the ones who play that game best, doesn’t mean that they’re leaders in the way that we think of like a Martin Luther King as a leader, right? He, he didn’t have anyone. He wasn’t a leader because everybody followed him because they worked for him, right. They chose to follow him because he painted a vision that they felt passionate about following. And that is hardly the job of a manager these days. So I think that it’s important to make that distinction or that millions of managers, but few of them are true leaders, right?

Jenn DeWall:

And we need to acknowledge that and start making that, you know, really owning that differentiation and training people appropriately with respect to that differentiation. Let’s go into chapter eight. It’s the System, Stupid. I love that name! I love your book because it’s just, so the language that you use and how you describe these concepts really are- I know we talked about this- that I feel like you could be my best friend. I do align with the corporate rebel or wanting to see things be different and wanting to kind of push the status quo. So let’s talk about It’s the System, Stupid. We’ll be best friends after this.

Lean Out or Lean In?

Marissa Orr:

The best friend’s necklace is in the mail. It’s on its way. Yeah. I tried to maintain a lot of irreverence and not take myself too seriously with this book. So I do tell a lot of stories that they’re just real and people relate to them. And I think that’s why it was easier to get a bit of a more provocative message across because it’s just imminently relatable. So, It’s the System Stupid. So that was my explanation for that chapter title. So at the end of the day, the real difference, well, there’s so many differences, but one core difference between Lean In and Lean Out. And that perspective is Lean In really blames stereotypes and culture for the lack of women at the top of corporate America.

And it, you know, it’s sort of, it’s built on this premise that women are oppressed by culture and stereotypes. And if we weren’t, we would be at the top as well. Whereas in Lean Out, the perspective is really that this is not a women problem. It’s not a female problem. It’s a systems problem. Like women are not broken. The system is broken. And what I mean by that is- so I’ll give you an example. Compared research shows that women prefer and perform better in collaborative work environments. Whereas men prefer and perform better in zero-sum competitive work environments and work is a zero-sum game by its nature. Its that triangle, the corporate hierarchy. He wins a promotion. I win a promotion.

At Google and Facebook, we were ranked relative to each other. You’re either you have to be either better or worse than your coworker. You can’t be equally great or equally terrible. And so really a lot of it was just this cutthroat competition. And the reason we use this structure is not that it’s inherently better than anything else. It was designed a few hundred years ago by a man in the industrial age. And if you’re Rockefeller or whoever, you know, the history of that piece is not as familiar to me. But if you’re a Titan of that era and you’re trying to design an organization, and this was really the first time in this country, we had to organize hundreds and hundreds of workers around these business goals and production. Naturally, if your view is that you like competition, you’re going to set it up as a competition, thinking that that’s the way to get the best performers to rise to the top, but it’s been a few hundred years. And since then, the entire fabric of our economy has transformed.

We’re not a production economy anymore. And the composition of the workforce is completely different. You know, it’s half women at the entry-level. And yet these systems are the only things that have remained exactly the same. Not one thing has changed, even though everything around it has. And so what makes more sense like rewiring women’s personalities to conform to this outdated system or rewiring the system to better meet their needs? So that’s really what I mean by, Oh, it’s the, you know, the system stupid. I follow up, and I go into a whole chapter and all the changes that would be necessary at work to make it a more level playing field for everybody. But I think at the end of the day, all we really want is a feeling of control over our careers and our happiness and our satisfaction. And I don’t think you need to wait for huge power structures to change in order to do that.

You can either change the rules of the game, or you can change how you play it. And changing how you play is all about defining success on your own terms, like being honest with who you are, what you want, and owning it. And, you know, that’s eventually how I came to terms with that environment, which is yeah, getting a manager feel good at the moment because that’s what my peers are doing. That’s what I’m supposed to want, but if I’m going to be unhappy, you know— so in the book, I suggest orienting around wellbeing instead of winning. And that really, it lets people account for their own individuality when they’re designing sort of the, their, their life and how their career fits in. Because honestly, for so long, 15 years, I was working for things I didn’t necessarily want. I was just following a script of what I was supposed to want. And that’s really what I mean by, you know, taking a step back and making sure, you know, you’re the author of your own story.

Jenn DeWall:

Yeah. I think it gets it’s easy. And again, I think a lot of this I felt trapped in earlier in my career, but still even right now, because the comparison is, is real. You look at what your peers are doing, or maybe that person that you’re kind of competing with because you want to get that next role. And you can get really caught up in goals that aren’t your goals like that becomes shoulds. I know early on in my career, I had, you know, my first few promotions, the next one, I didn’t necessarily want to do it all. But I felt like, well, that’s the only way that you’re going to get ahead. That’s the skill or role that you need to have, even though it’s not where I brought the most value, but again, it was the most expected one. Well, you have to do this to get to the role of this. Right. Okay.

Jenn DeWall:

Well, that does it have to be that way? Like why do you think we’re so cemented in, and some of these systems are in some of these ways of doing things like it’s, it’s so interesting to bring it back to just the industrial revolution and that era and knowing that today, even though the landscape is dramatically different, that we still have not altered things like what the heck we have changed, like the type of shoes that we wear, the cars that we drive, everything, but yet we just were ignoring this one.

Changing Perspective on Navigating Careers

Marissa Orr:

Yeah. Well, I think that’s human nature, really. People get comfortable in a certain way, and momentum builds and just keeps going in that direction. And then, you know, inertia sets in, and I think it’s hard to step out and see the bigger picture to be fair. So, for example, a friend of mine read my book, and she was dealing with this issue in her company. Now she’s the owner of the company where this woman wanted to promote her, but it was a similar situation. She didn’t want to like to manage the whole team. So they were going to give it to this other guy, but they were concerned that he would undermine her. And she said to me after, so she had been struggling with this challenge, and she didn’t know what to do about it.

And then after reading my book, like she had this insight like, Oh, I’ll just give her a raise commensurate with that position. And I’ll make them partners in decision making, give them 50/50 weight. And if there’s an issue, you know, she’ll step in, but he’ll do the day-to-day management team. And what she said to me was like, it was so weird. It didn’t even occur to her that she could think outside that structure in that box.

And I think that’s a big part of it is, you know, another friend of mine, when I was explaining to her the premise, while I was writing the book, she’s like, well, then what would happen? It would be anarchy. Like you need people. And I was just like, it was, I was like, Whoa, no one saying you don’t need people. I think change- one, and we’re sometimes so stuck in our own perspective, we don’t see other ways out. And two, you know, people can’t see what you see from the bigger picture. It’s scary. They think it’s a threat. And so I think those forces combined, and we just remained stagnant, which is why its a mistake to wait for everything to change in order to be happy. You’ve got to just figure out, you know, right now today, how you can navigate in a way to make yourself happy.

Jenn DeWall:

Yeah. So call to action would be for the individual, figure out how you can be that author of your own story or what makes you happy. And maybe a call to action to the leader is to challenge these systems, figure out if they are helping or hurting you know that the origin may not actually be relevant anymore, or even prove a valuable case to actually keep these systems in place.

Marissa Orr:

Or just know what your employees are really motivated by and try and give that to them instead of relying on, you know, what the system spits out as the reward. Sometimes people just want recognition, and it doesn’t have to be this like, you know, and sometimes people do want the big title, to be the big manager, great. Like that should be available too, if that’s what you want. But right now, that’s all we have. So expanding the scope of rewards and, and you know, how you motivate and acknowledge your team can make a big difference.

Jenn DeWall:

I know. I really appreciate you just going into Lean Out. And for those that are just even curious, you know, go out there like you, you have a great way of looking at how we can maybe assess and analyze our work culture, our role as leaders, how we look at our own aspirations and goals. But one of the things that we had talked about offline to bring in because we don’t often talk about this. You made the shift from the glamorous corporate world, right? Of Google and Facebook. And we know because if you aren’t at those companies, those are oftentimes the companies that you would aspire to work for. So then how do you make that? Or let’s talk a little bit about that transition from working for the big corporate organizations to then rolling into the land of entrepreneurship, which is definitely something that is, you know, shiny object, but it comes with its own host of challenges.

Going from Facebook to Entrepreneurship

Marissa Orr:

Yeah. The grass is always greener for sure. So the best way I’ve ever heard this play, I wish I remember where I heard it, but it just captures the journey from, you know, being in that world to starting your own thing. When you do that, you trade depression for anxiety. The best, most concise way that fully captures what this journey has been like for me. Because in that world, you know, I was safe. I was secure. I had a paycheck every two weeks. I had a really nice life, like as a single mom of three kids. Like I made a great salary and life for my kids and me. And I live in a great school district, you know, no matter how bad my workday was, that paycheck was there every two weeks, I had benefits all like I worked at Google and Facebook. I had the prestige, the massage appointments available, the food, like everything you could possibly want.

And I have to say— I really did enjoy Google. I, you know, I grew up there, some of my best friends in the world or from the time, you know, that I work there and there’s a lot I missed about it, but there was this something inside of me looking for something more. And I knew I had all this potential and talent in me that could not be expressed in that world. I was limited. And I think when I went to Facebook, part of me was searching for, you know, maybe a smaller company. I can make a bigger impact. Because I just understood, there was a part of me that needed to be expressed that wasn’t, and then it’s Facebook. It was like, ha-ha, the jokes on you. You think this was the place for you while like we have a hole and I go into this story again in the book, but it really was a terrible experience at Facebook and forced me to come to terms with, you know, I was in a dark place, and I was like, you know, who am I, what do I want?

You know, I thought this would be the fix for those empty or void feelings that I had at Google, but it actually made them worse. So what is it? What am I really looking for? And it really had to go through how, in order to make the commitment to change direction and take a huge risk by going and pursuing my dream, which was to write a book and speak full time to women. And the summer I was still working at Facebook in 2017 is when I really decided I made that commitment. And I wrote the book proposal that summer, while I was still working at Facebook, wake up like godly hours in the morning to work on it. And then, when I left Facebook, I had already almost finished the book proposal. So I had proven to myself that I was taking this seriously, and I ended up, you know, pursuing it.

And here I am three years later, almost exactly doing it right. I have the book published. I’ve been speaking full time now, and it’s extremely rewarding. It’s also extremely, extremely difficult to really, it’s very risky. I’m not a financial risk-taker. And I really put my life savings on the line to say, okay, I have like a year and a half to make a buck. Like that’s the runway, I had. I’m very fortunate. So I’ve had that, but you really, like, it’s not easy to just completely blow your life savings when you have three kids. And so it was a big risk, and it comes with tremendous anxiety, total uncertainty. You kind of question yourself all the time. Am I crazy?

And I feel like I’m really on the other end of that sort of period that, you know, the, I was going to call it the dark nights. No, that’s a movie. I mean, like the terms that come to me like a dark night of the soul, maybe I thought it was, but it’s not easy. It’s been really tough. I wouldn’t trade it for the world because I learned, talk about confidence when you do something like this, and you sort of survive, and you get through it, that’s confidence because you start to trust yourself more. So that’s something no one can ever take away from me is, you know, this thing that I pulled off by myself on my own, of course, I’d help from people like, you know, that supported me. Not financially, unfortunately, but like, you know, in general, my friends or whatever. But when you do something like that, that confidence just is joy, and it can’t be taken away by anyone. So it’s worth it. And I still feel like I’m at the beginning of the journey, I’m at the base of I’m at the summit, getting all my terms confused, like the bottom of the mountain, what do you call it?

Jenn DeWall:

The base.

Work On Your Plan Before You Jump Careers

Marissa Orr:

The summit, the base, whatever. I’m still at base camp. I know that I can use it, so I have a lot more to climb. But it’s definitely, you know, there are days I miss so much about Google, and I know there were days at Google. I would be sitting in meetings, like really feeling like I was wasting my life. And so there’s a trade-off. And as long as they’re willing to accept that trade-off. I always tell women that asked me, like, they’re thinking of doing that, you know, kind of transition from corporate to entrepreneur. My advice is always to first work on what you want to work on before you leave that world. Like, give yourself some space to try things. Just jumping ship is tough. And it doesn’t mean you shouldn’t do it, but I think sometimes we think of it as an all or nothing, and it doesn’t have to be.

Jenn DeWall:

Yeah. I love that. You know, the grass is always greener, but really thinking that you can try to do whatever you want now today. You don’t have to just quit your job. And I mean, but, but that also doesn’t mean to stay at your job. You opened up talking about a lot of the reasons that people choose to stay in an organization because of the benefits package because of the salary, because of all of that security. Of course, that makes sense. But how long are you willing to put off being happy? Because there’s also, I’ve had a job where I have gotten great pay, but you know what? Then, I guess, the consequence that I had with that great pay comes down in terms of low confidence, not feeling good enough, not feeling like I’m valued or that I’m contributing, or allowing myself to kind of see myself through the lens of that culture, whether that culture was even worthy of that, of applying that. And they think, how do you even get the courage to jump? Because that’s, that’s one of the biggest ones.

Marissa Orr:

That’s kind of what I mean by don’t just have this idea and quit. Because I think having some sort of creative goal— because the underlying problem is we’re really relying on work to fulfill our need to be happy. And when our job sucks, we blame our job. But the truth is there are ways that you can take the initiative of fulfilling your own needs. That doesn’t rely on work because then you’re, you’re giving work too much power over your life. And it’s hard. Look, I’ve been there. Works made me miserable more times than I can count. But what I learned at Facebook was having that creative project, that book proposal, where I worked on it every morning. And look, I know it’s tough to find the time. I mean, again, I’m a single mom of three kids. I had an hour and a half commute each way.

I was waking up at 4:30 in the morning, and it was tough. But at the same time, having that thing, I was creating increase my wellbeing and sense of security in ways I never would have expected. Because I go into work and the slights and the undermining, all the terrible things that were happening suddenly didn’t affect me anymore. Like I was like Teflon because I had this thing that I was making. And it was like I was taking control back. I was going to be the author of my own story. This wasn’t going to be how it ends for me. That’s a tremendous sense of power. It doesn’t have to be a book proposal. It could be any sort of project or goal that gives you a sense of control and ownership over your life. And I think if you’re thinking of leaving that world to start your own thing, what do I know?

But my advice, because, based on my own experience, I just feel like it’s a caveat. Because it’s not, you know, you have to take everyone’s advice with a grain of salt, including mine. But working on that while you still have the safety security of a job, one it gave, at least for me, it made me take this pipe dream seriously. Cause if I would’ve just left and then started writing a book, I would have been too anxious. And I, and I don’t think I would’ve trusted myself, but showing myself that I was serious about it. Not only just improve my day to day wellbeing at work, but it gave me the confidence to then make the jump. So that’s my advice to really don’t think of it as an all or nothing right away, but to kind of dabble and create these projects in the direction that you want to go.

And then once you get some momentum or you feel better, more confident that then you can leave, you know, it’s, it also helped me because I saved that money that I was sort of riding out Facebook as long as possible to, you know, use this money then to then start this other project. So there’s, I think a lot of benefits to both trying to do both at the same time, at least for the short term,

What is Your Leadership Habit for Success?

Jenn DeWall:

I think that’s a great closing perspective or call to action. Inspiration. If you will to, you know, take the reins to just try and let go. Maybe not jumping off the cliff, but like just slowly going and dipping your toe in where we close every single podcast with one final question, and I need to hear it from you. Where is the, what is your leadership habit for success?

Marissa Orr:

Oh gosh. I’m like, I’m thinking of my habits in general. I mean, I meditate every morning. Does that count?

Jenn DeWall:

Absolutely. How long do you meditate? Or, what benefits have you seen from meditation?

Marissa Orr:

Well, going through my experience at Facebook turned me into a straight-up Buddhist because I needed some ways to like manage my emotions, and I felt so out of control, I kind of was turning to different things I can do to get a hold of myself and be in control of my own emotions. And so meditation sort of kept coming up. So at first, I said, I was still working at Facebook, and I promised myself I would just five minutes a day, no matter where it can get it. And that was my first small goal. And there were times I would have to go into a bathroom stall and lock the door and do it for five minutes because I knew if I didn’t do it, then I wouldn’t have time the rest of the day.

So once I was doing that, then all of a sudden, you know, it became more of a then when I started writing the book proposal, I made it more of like my morning routine. So it started with five minutes a day. Now I try and do 20 minutes a day, usually ends up being 15. And I also try and practice it like in the car, in line for the grocery store. So it’s, it’s kind of like I pepper it into the day, but I have pretty much a 15 minute dedicated time every morning.

Jenn DeWall:

I love that. Again, carving out time for yourself, figuring out what you need. I feel like even that habit brings our whole podcast to a close, just starting with us. How do we want to show up? What changes do we want to make? What type of leader do we want to be, but starting with meditation and kind of getting awareness around how we’re showing up in the world. Marissa, thank you so much for just coming on to the leadership habit podcast. I am so happy that I’ve got to interview you, so happy that I got to read your book. I look for the best friend’s necklace in the mail.

Marissa Orr:

Hey, Oh, one more thing, I want to just let viewers know that I started my own podcast. It’s called Nice Girls Don’t Watch the Bachelor, which again is kind of lighthearted in a Reverend and into the title. I’m actually a huge fan of the show. But it’s on app podcast, Spotify, wherever podcasts are. So people want to check that out. That’d be great. Well, thank you so much for having me.

Jenn DeWall:

Yes. Thank you. Thank you so much for listening to today’s episode of The Leadership Habit podcast. Now, if you want to connect with Marissa Orr, you can go to MarissaOrr.com or follow her on Instagram, connect with her on LinkedIn, follow her on Twitter. Bonus- If you want to get more, she actually has a host of her very own podcast called nice girls. Don’t watch the bachelor, but you can find in your favorite podcast streaming services. Thank you so much for listening. If you enjoyed today’s episode, go ahead and purchase Lean Out. Her book was an excellent read. I found a lot of value in it. You can find it on Amazon or wherever your books are sold but purchase Lean Out by Marissa Orr. And also, if you enjoyed this share with your friends, you sure to write us a review on your favorite podcast, streaming service. Thank you so much for listening until next time.

Episode 41: Lean Out with Bestselling Author and Leadership Speaker, Marissa Orr