Welcome to UnF*ck Your Brain. I’m your host, Kara Loewentheil, Master Certified Coach and founder of The School of New Feminist Thought. I’m here to help you turn down your anxiety, turn up your confidence, and create a life on your own terms, one that you’re truly excited to live. Let’s go.

Hello, my friends. So I am really excited to be here today with an incredible woman who’s also been one of my students and clients, and I’m just obsessed with her career trajectory and story. And I think you guys are going to be too because like mine, hard left turn. And so I am just excited for you all to hear this story and hear about how thought work has helped her in her journey. I know I’m being very vague and mysterious because I’m going to let her introduce herself and explain what she’s up to. So, welcome to the podcast, Lisa.

Lisa: Thank you so much for having me. Delighted to be here.

Kara: So tell us a little bit about kind of your career trajectory and the point at which you came to coaching during it.

Lisa: Sure. So I have been a global women’s rights activist for the last many decades, and I came to coaching and to the Mastermind as CEO of a global women’s rights nonprofit that has been working for 13 years on a global treaty on violence against women and girls. And I don’t know how quickly we want to get into some of my mental noise around that.

Kara: Let’s quickly, just give us the overview now, and then we’ll dig into it.

Lisa: So, global diplomacy working to effectively get every nation on earth to commit to legally binding standards to end violence against women and girls. So basically, dismantle the patriarchy in every country on earth.

Kara: A small goal.

Lisa: Never mind the fact that I wouldn’t have been satisfied until it had been fully implemented in every country on earth also.

Kara: So you were doing that work. And then what was going on in your brain that brought you to coaching?

Lisa: Yeah. I had a tape going for years that I was a bad CEO, that I was unhappy, that I was in the wrong seat. And I came to the Mastermind about three weeks before my 50th birthday and had a lot of thoughts around turning 50 where I thought my life was going to be. I had undergone massive changes on the personal front as well just a little over a year before.

And so I had spent a decade feeling pretty much every day like I was showing up at work and failing and then going home and failing. That was the tape I was playing. And in particular, the big life change that had taken place some months before I came in really threw me for a loop, and so I was re-examining everything. And my objective coming in, the goal that I picked was to fall back in love with my job.

Kara: So just for context for our listeners, what Lisa joined was the Mission Impossible Mastermind, which is a small, high-end Mastermind that I lead personally. I do all the coaching in it. And so you come in and you pick a goal for your six months, supposed to be an impossible goal. So you picked falling in love with your job. Why was that the goal you wanted? Why do you think that’s the way your brain was going?

Lisa: I knew I needed to make a decision that I could not continue to have this kind of ambivalence around the role that I was playing, that I needed to either be all in or make a decision to move on. And I wanted to offer everything I could, and I had a lot of mental tapes about what it might mean to leave since I was the co-founder of the organization and had been in the role for 13 years. I had a lot of beliefs about how it would fail or that I would be giving up on something really important if I were to transition.

So I had a lot of tapes about what I was allowed or not allowed to do if I was truly a feminist, truly an activist, truly in solidarity with people around the world. And I also think it’s important to mention that our first Mastermind meeting took place on Inauguration Day. And so there was something there about what was happening in the world and what it meant at this moment to in my head, give up rather than thinking about it as shifting my role.

Kara: And it’s so interesting because especially for those of us who are like, fuck the patriarchy, it can’t tell me what to do, I don’t want to live by its rules. And then we’re like, so what I’ll do is invent my own set of rules to impose on myself about how I’m bad at everything and never doing enough, right? It’s like we just replicate that with different being a good activist, being a good feminist, being a good founder, being a good parent, being a good spouse, whatever, right? We are like trying to reject what society tells us, but then because we’ve been so conditioned to like be in that constant self-surveillance, we just come up with a different set of things to constantly police ourselves about.

Lisa: Absolutely. One of the things I had to realize is that I had lived my adult life believing that my entire value was based on what I was contributing and my achievements. And what I found in the Mastermind group is that was true of almost everyone who showed up there. This was a group of extraordinary women achieving extraordinary things and invariably feeling like failures no matter what goals they hit.

I also think it’s important to acknowledge that I had been doing the thought work. I had started listening to your podcast, maybe six months before some big life changes took place, and it had played an important role. I signed up for the self-coaching trainings and worked with it, found the tools incredibly powerful. But there was a lot I wasn’t scratching until we got into the process together.

Kara: Yeah, let’s talk about the process because it did not take you where you expected.

Lisa: No.

Kara: So what did you end up kind of experiencing? You came in wanting to fall in love with your job, and then what happened?

Lisa: Well, we had six months, and after three months, I decided I was going to leave my job. And it’s interesting, here’s what I would share. There were two thoughts that I ended up working on. One was simply that it was possible my transitioning into a different role would be of greater service to the work and the movement. Just that it was possible, not that was a guarantee, but that it was possible that was true.

And then secondly, I had a whole set of thoughts around turning 50 and what society tells us about what’s possible economically. Like, if you’re over 50, you’ll never get another job. You’ll be living in a van down by the river, as you like to say. And so the other thought that I practiced was it’s possible that I could generate more income and economic stability in a next chapter of my own crafting.

Playing with those two thoughts were really helpful, and then some health issues were also cropping up. And with international travel, which was a big requirement of my work at the time, and I think being able to approach that with compassion and curiosity was incredibly important. That’s kind of the heart of what I was working on in that first Mastermind, looking at my own thoughts around what it meant to be a good activist, a good person, someone who’s showing up in the world right now and exploring the possibilities for what does it mean for an organization to have a second chapter being really aware of founder syndrome and that actually stepping out and sharing leadership can be a very powerful form of service.

I still absolutely love the work, but I didn’t love the job and the role. And so being able to distinguish between those two things and start the process in motion. I think I also became aware with stresses that I was carrying that the fact I was not in the best place maybe negatively impacting the work and that attending to myself could be an important part of that work.

Kara: Yeah, I mean, one thing I love about your example is that it was like, once you were able to start questioning some of your stories about who you had to be, you ended up seeing so many different options, right? So we just were talking before we started this that you just got back from Geneva because you actually were able once you sort of got out of that like binary, black and white thinking, I have to do exactly this or I’m a bad person, you were able to see like, oh, there actually I could do this. I could be a consultant. I could help with the transition. I can work the amount I want and ask for more money for it, which I think you did, right?

Like, you were able to see so many more creative solutions. And I feel like that’s part of what is so it’s so hard to appreciate when you’re in it. When we’re in it, we’re like, no, I understand this. I’m living it. I get what my options are. I know what’s what. There’s no solution to this problem. And then part of the beauty of coaching is like it really, I think, helps you with that cognitive rigidity. And all of a sudden you see, oh, there are a lot of options open to me.

Lisa: Absolutely. So I was able to have a conversation with the board and effectively really zero in on what are the roles only I can play for a time? And how can I support the organization in the transition while using my gifts, using the things that are actually my sweet spot, rather than, before, there were pieces of it that felt kind of like clawing my way to average rather than just my highest and best contribution. And so, yeah, I just came back from Geneva.

I was there with board members and donors working out systems for people to be able to go to Geneva, see what’s happening, support the human rights system there without me being there. I don’t need to be in every room in order for impact to be had, right? I remember actually a couple of years before, I had come back from Geneva, sitting in my backyard in the middle of the night, jet lagged, just crying because I felt so much like when you hold a suitcase that’s too heavy and you set it down, it’s hard to actually open your hands because it’s painful because you’ve been holding it so tightly. It was like that. That was sort of how I was approaching the work. And it was just unnecessary and actually not the highest and best. So, yeah.

Kara: Yeah. And everyone needs to know what else you’re doing now. So you are working to transition your organization and…

Lisa: And I’m starting a dahlia farm.

Kara: It’s my favorite, one of my favorites.

Lisa: I’m a farmer, friends.

Kara: But it, tell people why, because it was such a good example, I think, of you like letting something be easy and building up your belief in your own strengths.

Lisa: I love flowers. I love dahlias. They make me happy. When I would be stressed at home, very often, I’d be going out into the yard, in my backyard, attending to my flowers, between things.

Kara: One of the things that came up in your transition to the dahlia farming, or quasi transition since you’re still doing your other work as well, was we did a lot of coaching around money and believing you could create money. And I think it wasn’t just for me, that coaching is important because it wasn’t just about the money, but it was about this thing I see often happen with women that’s like, I know I can do these things for other people, but I don’t believe I can do it for myself.

So in your situation, we talked a lot about like, well, you’re an epic fundraiser, and you have created a ton of money for your organization and always drawn money to you and had a business before you became, got involved in this work. And then did all of this work, but it was like there was this disconnect in your brain that’s like, oh, I can do it for the cause but not for myself. And so I’m curious if you can talk a little bit about that transition for you.

Lisa: Absolutely. I was terrified that I would go broke and that I would make bad decisions. And I had a kind of tape going about being bad with money. And of course, as we talked and reframed it, it was like, no, I’m actually very good at raising money, making money, financial planning. So it was a little bit of a hilarious aha moment when I actually was in contract on a farm and I was trying to decide whether or not I could make that work.

And this thought sort of popped into my head, which is like, oh, I can’t make a wrong decision because no matter what happens, I’ll handle it. It was as though it was my thought. And then I laughed out loud because I realized I’d heard you say that probably 20, 30 times, and then it just kind of bubbled up like it was my own. And honestly…

Kara: But that’s the beautiful moment though, right? Like, that’s what I want for all women is like…

Lisa: Whatever it is, I’m going to handle it.

Kara: Full integration.

Lisa: Whatever it is, I’m going to handle it. And so what had been at the beginning of the process kind of waking up in the middle of the night sweating, terrified, just like instantly, the anxiety was gone because it was like, no, I’m good at making money. So, if I do it this way, I’ll monetize it this way. And if I do it that way, I’ll figure out some other way to make it work, but there’s no wrong decision to be made. And what was fabulous about that is it wasn’t even just limited to the question of the financial model around Kaya Blooms. It was, it really has penetrated almost every area of my life now.

Just feel like, no, there’s no wrong decision. I’m happy. There’s no disaster to be had because whatever comes up, I’m going to handle it. And that is new for me.

Kara: Yeah, and that is, I mean, I think that’s what makes me able to take risks or do bold things, is like, I’m going to handle it, right? And not I’m going to handle it like, oh, I’ll survive it, white knuckling and in burnout, but just like, it’s cool. I got it. I’m going to figure out whatever happens. I’m a human. Probably some stuff’s going to happen. I’m not going to enjoy.

But it’s not going to sort of make me throw myself under the bus or berate myself or blame myself. It’s like that resilience. And I think that part of the work we did on the money stuff around creating this new flower brand and the farm, is I think that I want everyone else to take away from it is like, because women undersell their own accomplishments, and they always have these other reasons that they succeeded at things like, I’m just a hard worker. I just, people were being nice. They were just doing me a favor, whatever, right?

It’s then when they want to do something new, they don’t see all of the skills they have that would transfer, right? So it’s like they may have the identity of like, oh, I guess I’m successful in this career, but it’s because of X, Y, Z, all these like discounting reasons as opposed to like, well, I’m successful because I’m a successful person, and I have these skills and talents and abilities that will transfer to my next venture. And like taking ownership of what you’ve created in one space, and then I feel like that’s been a big theme of the Mastermind. Not everybody coming in is changing something. Some people are like, are learning to love the job they have, right? Or are doubling down in their relationship or whatever else. But for the people who are making a transition, I think a lot of the work is like, how can I draw confidence and inspiration from what I’ve done already and really owning that?

Lisa: Absolutely. So for me, a part of that was like, I’m actually a very good entrepreneur. I’ve solved a million problems. And then I also had this thought, wait, if I’ve helped move nations toward addressing violence against women, I can grow some dahlia tubers and it will be just fine. I’ve done much harder things than this. So that part of it, the idea of something that’s just kind of practical, tangible, and then a learning curve and adventure, but thinking in innovation is something that I’m good at. My brain is very well suited for that, even though it may not be well suited for particularly things, the entrepreneurial and innovation space is something that I’m good at. And I’m bringing that to the dahlia party.

Kara: Yeah, I love that. And then in the work that you’re continuing to do in the movement, you’re able to show up with the parts that are, like you said, the best use of your brain, like the parts that you’re best at, right? Sort of like as opposed to having a job where you’re like, half of this is not really my strength, but half of it is. Now you’re it’s like two half jobs, each of which are your strengths and that’s possible that you can like forge your own way.

Lisa: The creative, the storytelling, the fundraising, the framing of issues up front, all that stuff. The idea that I would spend my time playing to my strengths just unlocks so much joy as opposed to drudgery. And that is my highest and best service of the movement, whether it’s through a book that I’m going to write or podcasts or dahlias or consulting, all of that is playing to my strengths and it feels so much better.

Kara: Yeah, and I think that’s really powerful because women, there’s so many strands of socialization that make women often have a hard time doing that. It’s like not believing they have strengths, believing that they should be good at everything. So if there’s stuff they’re not good at, then that’s like bad and wrong and they should keep trying and get better at it, or it’s shameful to have these areas they don’t like. So it’s such a good example.

Lisa: It’s interesting you say that too. I’ll just add one other thought that I practiced from I’m a bad CEO. I switched it to I am a classic founding CEO, which was a little bit of a joke to myself because like freaking crazy in some ways, but entrepreneurial and all the zippy little neurodiversity that comes with that party just puts me in the same company of a lot of men who are celebrated for those reasons. But women…

Kara: One hundred percent.

Lisa: If you’re not like super detail oriented and have a meticulous accounting, like filing system or whatever…

Kara: Oh my god, right. Can you imagine like, is the head of Anthropic AI being criticized because like he can’t keep track of details or like he doesn’t like to file expense reports or whatever? No.

Lisa: Exactly. Exactly. Well, and also, I think this is an important point too that we talked about early on, but one of the things that was really hard for me in my job was the idea when you are running a global nonprofit, you sometimes have to make hard decisions and you don’t make everyone happy. And there can be a little bit of a double bind in the global feminist movement where you’re expected to be this soft, nurturing, enlightened, 100% horizontal management structure. And if you do anything less than that, you’re a bad feminist.

And so one of the things that came up in our very first Mastermind was the notion that it’s impossible to move through the space without a teensy beensy bit of harm.

Kara: I didn’t say teensy beensy. I just said without harming some people.

Lisa: Okay, well I’m trying to be I’m trying to be delicate here. There’s going to be harm and I think that as a movement, we tend to hamstring ourselves this way where there’s this expectation that unless you’re just like the most enlightened, both powerhouse and soft mommy cuddle buddy with…

Kara: Soft mommy powerhouse.

Lisa: Exactly. That you are a bad feminist. And I think it paralyzes us because we don’t really allow women leaders the full range and complex little bundle that is being a human being trying to do something good and stumbling while we do.

Kara: One hundred percent. And like, I have a new COO and on my team, we had like no turnover for like four years, and then we started changing things up. And now like, we’ve had, you know, we’ve had to change a lot of our team. So it was like all these new people coming on, which is an, you know, chaotic but an amazing opportunity. But it was really a relief for me to be hiring this new COO.

So like moving away from changing up our structure, having, you know, a different leadership team, hiring this new COO, and being at such a different point in my career as a boss and as a COO and as a founder and more comfortable with myself and just being like, hey, I don’t want to do XYZ. Like, I want to hire someone who cares about this. I think it’s important that people care about this in an organization. I do not personally really care about it. I mean, I care that it happens, and I will pay someone else to do it. I don’t want to do it myself.

I don’t want to have to think about these kinds of issues. I don’t want to have to solve these kinds of problems. I’m not interested in spending time thinking about X, Y, and Z. Like, and some of those are things that were, you know, aligned with what society expects of women, and some of them were not. So that was just so freeing and to know she was the right person because she was like, cool. Yeah, that’s great. I’ll do that.

Lisa: It’s interesting you say that because the very first thing I did with Kaya Blooms is hire someone to do all those sorts of things as well. Like operations, plant science, she’s an ecosystem scientist, awesome, go.

Kara: Yeah, in men, that’s strategic leadership, and in women, it’s like, oh, who do you think you are or like, oh, you don’t care about this? You think you can just outsource that? I’m like, yeah, I’m a CEO. That’s literally my job. So I we could talk about this forever, but I would love for you to share a little bit about, we’ve talked a lot about the work you did in the Mastermind, but I would also love for you to share a little bit about kind of your experience with the Mastermind yourself. So had you been in a Mastermind before? Was this your first kind of coaching experience?

Lisa: Very much my first Mastermind, first coaching experience, group coaching experience. Yeah.

Kara: And so what was different about being in this container versus kind of being in The Feminist Self-Help Society, my membership, doing the work on your own?

Lisa: One of the things that’s different from being in the bigger coaching sessions, et cetera, is you have a community who’s going on that journey with you. A lot of them, you get to track their journeys and see them circling around similar things, being coached multiple times on issues in kind of bundles, watching their breakthroughs. And that was incredibly powerful. Particularly because you pretty quickly figure out you have a lot in common with a number of the people who are there. So watching their coaching feels like getting coached. I can’t tell you how many times I would sit through and write down sentences, names, et cetera.

A couple of other things that I think are really important. In the Mastermind, I will admit to being surprised at how incredibly available you were. So some people did well in live coaching sessions, but we could always go in and post, here’s the model I’m working with, here are my questions, and you were on it. So for me, one example around that would be I didn’t completely understand or grasp the results line.

I often was crafting the results line in ways that were kind of almost like a judgment of myself. Well, damn it, if you think this, then you’re going to just have this result where no one likes you and you’re a bad person.

Kara: You’re like, this coaching model’s great. It’s showing me what a bad person I am. I love this. This is really useful.

Lisa: Exactly. And you know, and you’re like, you know, that’s actually never the objective here. So it was funny over the course of the two Masterminds that I did, I was still being coached on getting the results line tight up until the end. I think it also created a structure for me. So I remember early on, and perhaps this is why I hit my goal so quickly. And I know you’ve talked about that before too, when you’ve invested in coaching programs because you’ve made the investment, it makes you take it really seriously.

Kara: Yeah, it’s just a known psychological bias you can use to your advantage. Like, that’s how people are. You buy a thing, you’re more invested in it.

Lisa: There you go. So we can talk about that drive toward accomplishment. But I think one of the things that many of us come in with is kind of layers underneath layers is shame. That kind of one of those bedrock feelings is shame. And I had all kinds of stories, thoughts that would produce shame, but stories that I believed kind of framed up why in my unique case, I should feel shame.

Kara: Right, of course. No one else should feel ashamed.

Lisa: No one else should feel ashamed. I think about this a lot too. Pema Chodron, this Buddhist teacher talks about how the fear underneath all fears for many people is actually the shame, like, if you knew me, if you really knew me, you would run. And when she said that, it blew my mind because I was like, oh my god, how did she know? Because everyone feels that way, right? But I felt so like seen and known. And yet, knowing that didn’t change it. And the work that we did actually did shift that.

I don’t want to skip too far forward because I’m sure we’ll get there, but I, you know, I have to tell you, it’s like, I wrote this, and I don’t know if people passed it on to you, but let’s just say by the end of the Mastermind last year, I realized that I have had this kind of version of myself in my head my whole life. And I thought if I could just kind of fix myself, I would get there. And I felt like I had spent the first 50 years of my life in like a prison yard up against the fence with the barbed wire looking at the hills, wanting to go there, imagining what it would be like but not knowing how to get there.

By the end of this Mastermind, I felt like I had finally gotten my get-out-of-jail-free card, and I was running for the freaking hills. Honestly, I finally feel like that person I always imagined I would be. So who I am now, it’s funny, I’ve had this experience, and I haven’t had a chance to share this with you. Just like that one thought bubbling up where it’s like, oh, I can handle it whatever. Now, recently, I have had this experience of every time I walk past the mirror, I’m like, damn, she’s cute. She’s beautiful. Oh, girl. It’s hilarious because I’ve never thought that way about myself before. I was always picking myself apart, and now I’m like, oh, honey.

Kara: And we didn’t even work that actively on that. I mean, you may have done your own work on it, but like, you and I didn’t even really talk about it much.

Lisa: Sure didn’t. Sure didn’t. It was funny actually, and I think this kind of ties into, let’s say, the objective and the result or the thoughts and the results or my objective for the Mastermind. I went to a poetry class recently and they were handing out different prompts. And the one that I got is my latest crush is dot. And I wrote about me. My latest crush is me. And I don’t mean in a really arrogant way, but I really genuinely love who I am.

I am the person I always wanted to be. I had this picture of someone who had aplomb, self-possession, and I didn’t know how to get it. And they worked 50 years to try to get it, and I finally have it. I finally have it. So that’s immeasurable. In terms of the transformation and the result…

Kara: So much good stuff. But let me just ask you this, so we could talk for hours. Did you have any hesitations before joining the Mastermind? What were they? And how do you think about them now?

Lisa: If I’m being honest, my biggest hesitation was the expense, was the price. To invest in myself that way, to invest in coaching for myself that way was not something I had ever done before. And I, like I explained, I could feel a little panicked about wanting to make sure I took full advantage. And the way I think about that now is it’s one of the best investments I’ve ever made. I can’t imagine any other path that would have gotten me here to a place of feeling genuinely free. I feel like I set myself free, basically.

Kara: With some good coaching.

Lisa: And there’s just no price to be put on that. And it’s the platform for the whole second half of my life. So very grateful for that.

Kara: Which I would love for, kind of our last question to just talk a little bit about because I think a lot of other people have that of like, I think for a lot of people, like, it’s not so much investing the money. I mean, obviously, if you’re investing this Mastermind, you have the money to invest in it, right? So it’s like the thoughts around it. And I think a lot of people have that same thing of like, but my fear is really like, oh, I won’t take full advantage. What if I sign up for it, and then I don’t do it perfectly, essentially, is what that means, right? And so you went from having that fear to being able to like take a nap during the in-person retreat and not worry about what you were missing. So how do you think about it now, like that fear of what if I don’t take perfect advantage of it?

Lisa: There were many ways people could take advantage of it. It was drinking from a fire hose. Like you were available in chats online, there was one-on-one coaching, there were the days at the beginning and the days at the end. So you were wildly available during the process. So anything we needed, we were going to get. And that also really put me at ease.

Kara: I love it. All right, Lisa, thank you so much for sharing your experience with us.

Lisa: My pleasure. My pleasure. Thank you, Kara.

Kara: I’ll see you soon.

Lisa: Okay. Sounds good.