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Getting Over the Career Slump, with Kathy Caprino

Getting Over the Career Slump, with Kathy Caprino

Episode 10: Getting Over the Career Slump, with Kathy Caprino

Kathy Caprino is an international career success consultant, speaker, writer and trainer dedicated to the advancement of women in business. She often talks about dealing with professional crisis, finding personal and professional fulfillment, and leaving toxic environments. In this episode, she talks to Kristy Wallace about how women can find their true potential by stepping back and acknowledging what isn’t working in their current career paths.

Episode Transcript

00:13 Sallie Krawcheck, Interviewer: Welcome, everybody, to the Ellevate Network Podcast. Sallie Krawcheck here, the Chair of Ellevate Network, joined by Kristy Wallace, our President, who today, is talking to Kathy Caprino who I think is... I call her... She's my bud! She's sort of my, I wouldn't say BFF, I'm not even sure I'd go to bestie, but we're buds. I really like her. She is an international career success consultant, speaker, writer, and trainer dedicated to the advancement of women in business. That's a mouthful. So Kristy, how'd it go with her?

00:46 Kristy Wallace, Interviewer: It was great! Kathy is just so interesting. She talks about dealing with professional crisis, finding personal and professional fulfillment, and leaving toxic environments. Have you ever been in a toxic work environment, Sallie?

01:01 SI: Oh, yes, I have! You want me to talk about it? [laughter] Yeah, this is the issue. I think as women, we just don't wanna quit. We have this idea that if I can have one more conversation, if we could just get together with my boss, and we can just understand each other, it's gonna be okay. And sometimes, I think we just need to quit.

01:26 KI: I imagine it feels easier to just deal with the negativity or the toxic environment than the prospect of moving away from it. Maybe we're afraid of failure, uncertainty.

01:36 SI: Oh, uncertainty, uncertainty. I think it's 'cause we love to get A's, that we feel like we need to be successful in everything we do, and we just stay. But so, okay, so...

01:48 KI: Did you love to get A's, Sallie?

01:49 SI: Oh, I did. Oh, didn't you love it, Kristy, when you turned over your test and there was an A?

01:54 KI: Yes.

01:54 SI: I know. And didn't you hate it when you turned over the test and there was not an A?

01:58 KI: Yes.

02:00 SI: Yeah.

02:00 KI: Yes, A's were something I... Very, very, very near and dear to my heart. I remember in college, I got my first D, and I called my dad, hysterical. I was like... I remember it still to this day, that's the impact it had. But never again, that was one time.

02:14 SI: Although it's funny 'cause boys are so different. My son brought home a D in French. I'm gonna say it was in middle school, maybe it was sixth grade, and we've had a talk, and said, "You are capable of so much more." And then, he brought home a D again. And I remember him saying, "Well, my teacher says it's okay, other people get D's." And I sort of pride myself on not losing my temper. I picked his French book up and I threw it across the kitchen, and said, "Not in our family." [chuckle]

02:45 KI: Throw the book at him, Sallie.

02:47 SI: He never got a D again, ever.

02:48 KI: There you go. Yes.

02:50 SI: So speaking of toxic environments like my kitchen was that day, so we asked the women of Ellevate Network, "Have you ever worked in a toxic environment?" 73% said yes. 73%, unbelievable! 16% said, "Somewhat, I had a difficult boss," so that's 89% have worked in a toxic environment or somewhat tough environment. And then, 8% said, "Yep, I had difficult colleagues." That should be 100%. I cannot believe that there's anybody who hasn't had difficult colleagues except for this 1%, "No, I've been very lucky." I would guess maybe they're 22 years old?

03:30 KI: Or they own their own business.

03:31 SI: Or they own their own business and they think they're terrific themselves.

03:33 KI: Yes, there you go! Well, we're gonna hear today about Kathy's toxic environment, which actually led to chronic illness. It made her physically sick from being in this environment, and so, it's very interesting to hear her story.

03:46 SI: Yeah, it's a very interesting story. She and I shared it over a glass of wine, so I know that listeners are really gonna enjoy it.


04:09 KI: Thank you so much for joining us here today!

04:11 Kathy Caprino, Interviewee: Thank you for having me, so happy to be here!

04:12 KI: I'm really excited! So I wanted to start, because I think your career is very interesting. So I'd love for you to tell us the story of your career path.

04:21 KI: I would love that. So to make a very long story short, I had an 18-year corporate career in marketing and publishing and membership services. And I would say from the very beginning, it was not the right path. But like so many thousands of women, and I know this now 'cause I've worked with over 10,000 women, we get on a path in our early 20s and 30s, we're thinking about achievement, we're thinking about moving forward, we're thinking about, "How do I get ahead?" And we're not stopping and saying, "Oh! Is this aligned with who I really am? Is this what I really wanna be doing?" So I had a lot of outward success. Made a lot of money, managed $30 million budgets, global initiatives, but inwardly, it was not successful. And when I hit 40, and I'm 55 now, those bumps turned into full-blown crises. So I faced chronic illness, infection of the trachea every three months for four years, but the trachea, of all things! I faced discrimination, I faced sexual harassment, I faced zero work-life balance. My kids were little then, and I lived in a different state from where I worked. Toxic colleagues. But I promise you worse than all of that was waking up everyday saying, "Is this really what I'm gonna be doing with my life? Is this it?"

05:45 KI: But here's the deal: I knew I needed help. So I saw a therapist, I went to a career counselor, took $1,000 of assessment tests, nothing moved me forward. And this is what I see in so many mid-career women. You know you want something different, but what is the practical plan to get there? I don't just wanna say, "Woo hoo! It's all gonna work out! It's all gonna come true!" How? How, how, how? So I couldn't find that plan, and I didn't do anything. So one month after moving to a bigger home, more financial responsibilities, was 9/11, and I was laid off in a brutal way. And that's another thing. Anyone who's been laid off, even if you hated the job, it's devastating. It's devastating.

06:26 KI: And at that moment, I was in my therapist's office, and I tell the story all the time. He said to me, I was crying, and he said, "I know that from where you sit, this is the worst crisis you've ever faced. But from where I sit, it's the first moment you can choose who you wanna be. Now, who do you wanna be?" And I remember saying, "I don't know, but I wanna do what you're doing." He said, "What does that mean?" And I said, "Help people, and not hurt people, and not be hurt." And from that fateful conversation, I became a therapist, trained as a coach, started talking to women around Connecticut. And what would happen is after these workshops, they would literally line up, some crying, some shaking, saying... Now, this was in '08 and '09, "No one is talking about women's crisis like this. No one." It wasn't in the national conversation. There wasn't a Sheryl Sandberg with Lean In. And so to me, that became the calling. How do I figure out what is this underground epidemic of crisis for women in the workplace, and how do I bring new solutions to the table? And that's my world now.

07:33 KI: You talk a lot about some of these warning signs, the physical illness that you're going through. Was that all at once? Was it gradual? 'Cause I know we were unhappy, but we don't always recognize it because it's something that just gradually seeps into our lives.

07:49 KI: Absolutely, and let me share something: I'm gonna talk about women here and I don't mean to paint every woman with the same brush, or every man, but I've done a lot of research, a year-long research with women overcoming professional crisis. So I really believe that what I'm sharing is research-based. But the reality is this: Women are warriors. Women are survivors. So they don't understand that what they're going through is a true crisis. They go, "Oof! This is a rough patch. I'm gonna soldier on. I'm not gonna give up." They do say, "Something's wrong with me. Let me tweak it some more." So there are warning signs absolutely all along the way that they're not seeing. What are they? Absolutely chronic illness, and exhaustion, and depression. A lot of the women that I work with are highly successful mid and senior level women, but there's depression. There's an energy suck, an energy drain that they don't know how to handle.

08:50 KI: The second thing is when they're crushingly working and they cannot be with their families. And I have a whole... My book, 'Breakdown, Breakthrough' has a whole chapter on balance. I get it. I run my own business, my kids are now 18 and 21, balance is hard, but balance is not impossible, but there are things you have to do. You have to stand up for yourself. You have to prioritize fiercely and live with the consequences. So some of the signs are toxic bosses. I've written about narcissism. If you're surrounded by toxicity and narcissism, it's a sign you're either in the wrong direction or the wrong job. Waking up feeling like, "What is the meaning here?" And I really wanna drive this point home: You cannot be happy in your work even if you love the function of what you're doing, but you don't like the outcomes... And this was me. There were many things I liked about my work, but the outcomes, what I was killing myself to achieve meant nothing to me. So for instance, I never really enjoyed marketing until now. Now, I'm marketing my own programs. And now, I read everything I can on marketing. I remember my husband used to say, "You don't read a book about marketing. What's that about?"

10:03 KI: So what are the other signs? When you're truly dreading going to work, when... Here's another thing: We can be very skilled, but if you don't enjoy using those skills, if it feels like a drudge, or a drain, or it's not authentic, or you feel like an imposter, these are signs you're in the wrong. And I call them 'four buckets,' and I ask everyone listening to think about it. Number one, you might be in a job but you want more. You want more juice, leadership, money, reward, value. You might like what you're doing, but not with this employer, that's bucket two. You need to be interviewing. I tell everyone: Interview every three months. I don't care if you just got a promotion or you're thrilled. Interview because you understand your value in the workplace. Bucket number three is, "Nope, I'm ready for a completely different way to use myself in service of the world." That's a different career. And the fourth is, "You know what? I'm ready to launch an entrepreneurial venture."

11:03 KI: But one thing I would share too, I call it the 'pendulum effect.' So many people, so many women are in a breakdown mode, and when you're in that mode, you wanna run. You wanna run to the farthest end of the world, and I did that. "I'm done with corporate," and what is the farthest thing I can think of? Marriage and family therapy. The thing is, if you do not address your challenges in your current moment in this toxic job, with this toxic boss, these challenges will follow you, and they did for me. The same kinds of challenges reappeared five years after being a therapist. So address your challenges. It's not easy. We wish that we could just leap and everything would be magically delicious. But it doesn't work like that.

11:50 KI: Not that easy, no. So how did you identify what you wanted to do? You said marriage and family therapy, but what was it that was the calling for you in that?

12:00 KI: Yeah, and let me tell you how I did it, and how you need to do it; they're not the same. How I did it was the minute therapy became... My therapist said, "You'd be a great therapist. Explore it." I went home and downloaded the curriculum from two universities near me. So it was personal development, and spiritual development, and communication theory, and systems theory, and family dynamics. I said, "Wow!" And there was in my mind, no question, that I was gonna learn this and become a therapist quickly and make $100,000. The problem is, what I did wrong... And I really don't believe in mistakes, but I believe in missteps that take you on a detour, I did try on the direction by interviewing a few people. But I interviewed only successful therapists who were making hundreds of thousands of dollars. I didn't interview the social worker in the agency who was burnt out. I didn't let myself truly try it on. And I'll never forget the minute I said I was gonna be a therapist... We had a couple over for dinner, and the wife, who was a musician said, "You're gonna be burnt out, miserable, and broke." And I went upstairs in the middle of dinner and cried.

13:13 KI: However, I'm not saying that every therapist is burnt out, miserable, and broke, but I wanna tell you what happened. I adored the three-year Masters, it was life changing. But I became a therapist, and what I was gifted at working with is depression, rape, incest, pedophilia, drug addiction, suicidality. And the crowning moment where I knew I was in the wrong place was putting the kids down for dinner and that... You know how kids often are just pure sweetness and light. The phone rings and my client says, "I'm gonna kill myself. I'm gonna wrap my car around a tree now." And that night, I knew this was not the right place for me because deep in my heart, I wanted to help professional women who had the ability to impact thousands of other professional women. So to answer your question, it was a journey, and one of my mistakes was I waited too long to pivot.

14:13 KI: So this is what I tell everyone: If you're getting the feeling it's not working, don't be in denial, and don't put all your eggs in one basket. I had put all my eggs in the basket of therapist. I had not been doing any marketing work. I was training as a coach, but my identity in my mind was I will be a therapist. So to re-pivot again was an enormous deal, instead of all along having a Plan B. And a lot of people say, "Mm-mm, if you have a Plan B, you'll never make Plan A." I don't agree with that at all. We need to be incredibly flexible. We need to be fluid. We need to really understand what's holding us back. And if I had done that, I would have realized coaching, and career coaching, specifically, was really the amalgam of everything I love.

15:02 KI: So I like the idea of pivoting. When you're a solo entrepreneur, do you have a personal board of advisors, a personal group that helps you through that, and helps maybe look at what you're doing from an outside perspective, and provide that insight?

15:17 KI: That is a fantastic question, and I wanna tell you I'm going through an incredible turning point right now. You absolutely need a board of advisors. But the thing is, as you grow and change, they need to change. And sometimes, we stay stuck with the same level of people, and with the same feedback. So it's important that you're expanding, and shifting, and evolving that base of advisors. But I do wanna tell you this: I'm going through something right now. I'm gonna be really transparent. I started out as a one-on-one coach, then it has morphed into my business being writing, speaking, leadership training, advising. It's huge, and it's many-faceted, so I have to have a team. There's a lot of PR. There's a lot of branding. In order for me to have the reach that I want, there's marketing. There's online marketing. And there are courses that I'm developing so that I can scale impact. I call it scaling transformation. So for me, there has been a shift that I don't... When I'm on a call for an hour, my dream is to have a thousand people on that call. And I do. I have webinars with a thousand people. But regularly... Now, it doesn't mean I don't love one-on-one work. I feel that that's where the rubber meets the road, that I'm really in someone's life helping them. But in the future, I'm wanting a thousand people on the call.

16:45 KI: Well, what has happened is I've moved into the world of online marketing, and there's some pieces of it that aren't a good fit for me. And I am beginning to... Just today, was writing an email to one of my advisors that what we have to do is stop very frequently along the way, and feel how this feels to be engaged in these directions. So for me, do I wanna spend 50% of my time in online marketing? No. I can hire a team to do that and be the advisor of that team, but what feels the happiest for me is writing, and making an impact, and coaching at a very deep level. You truly, as the owner and founder, you have to look not only at the external factors that are gonna generate money, but you have to also understand what is the best place for me in the world.

17:41 KI: It sounds like you've really found meaning and purpose in your career and what you're doing. How do you work with women to help them find meaning and purpose?

17:50 KI: Love that question! So let me just give you my process, which I do think is somewhat unique. When someone reaches out... And I do only work with people who are a fit. And here's the fit: They have to be ready to do the work, and millions of people are not. So what does the work mean? I've developed something called the 'Career Path Assessment,' 11 pages of questions I wish someone had asked me 30 years ago. And if I had answered them, I would not have made the mistakes I made. And it's fascinating to me how, I would say, 90% of the people in my courses, and my clients cannot answer these questions. So number one, it's about connecting all the dots of everything you've ever been. So it asks every job you've ever had, what you loved, what you hated, what was a struggle, what you wanna take away from it, and what you never wanna do again. And it also asks, "What are your natural gifts and talents? What's the legacy you wanna leave when you're 90, looking back?"

18:49 KI: And here's another question: What are you uniquely gifted at? You have a special amalgam of talents, gifts, traumas, histories, perspectives, filters, values, things that mean something to you, that mean nothing to you. If you don't marry all that up, you're wasting who you really are. But we cannot see this on our own, period. Einstein said, "You cannot solve a problem on the level of consciousness that created it." So people will say, in these questions, I'll say, "How are you different? How do you stand out?" I don't know. "Okay, so we start there," and truly, because I've seen thousands of these assessments, 'cause I've worked with so many women, and we just go right to where you're stuck. And often, it's gonna be these things. Human beings only look at what's at the tip of their nose. So if you have a toxic boss who's telling you you're crap, that's what you believe, you forget. You forget how... When I was laid off, and it was brutal; for years, I forgot what I had achieved at this job. I brought in million-dollar bank clients. I turned fading businesses around. But I just remembered the toxic end. So we only look at that, and we need to stand back.

20:08 KI: Number two, we've forgotten who we really were. When I look at when I was 18, here's who I was: I was a writer, I am a singer. I performed on stage in big roles. I was a very competitive tennis player, I like competition. People would come to me, boys and girls, and say, "Can you talk to me, I have a problem?" And I would say to my mom, "Why are they asking me, I'm the same age? I don't know." She said, "Well, you got the gift." And I remember my dad, who was a scientist and a chemist, said, "Wow! You really always wanted to get to the bottom of things." So I was always very good at taking chaos, and making it crystal clear. Flash-forward all these years, it's exactly what I do every day now. But I didn't see those as talents or special, and that's another thing. The things we're naturally gifted at, we don't see because they come so naturally to us.

21:00 KI: So the process for me, back to your question is, I help people understand who they really are, but then, you need the practical process, and that's LinkedIn. That's building a network. That's speaking up for yourself. That's negotiating hard for what you want. That's building a case for what you want. That's finding the right people. So it's this special mix of depth, and then, practicality.

21:25 KI: That's great! That's very really...

21:28 KI: I don't see it out there then. And you'll hear that I'm not overly humble. I know what I've got, and I know what I give. But I really don't see that mix very often. I hear, "Let's fix your LinkedIn profile," which is an essential step. But if you don't believe in yourself, and you don't have any idea what you're gifted at, your LinkedIn profile's not gonna do it for you. You're not gonna be able to connect in a powerful way to opportunities and people.

21:55 KI: And so, it sounds, from what you're saying, women might lack in confidence.

22:01 KI: One thing that really makes my head explode is when we take a very complex situation, like women's situation today in work, or in life, and we boil it down to one simple thing. It's not simple. The confidence... And there is a confidence problem with women today, unequivocally. But it's multi-faceted, it's how we're culturally-trained. Different generations are very different. I'm a Boomer Generation, my daughter who is 21, very different. It's even rigid gender roles. Gender is more fluid now today, the way younger people look at it. But the way I was trained, and I work with a lot of midlife women, you do not talk about yourself powerfully. You do not put yourself first, that's selfish. Today, women tell me, "I feel guilty investing in your course."

22:51 KI: A woman told me just the other day, "I just plunked down $3,000 from my son's tuition payment without blinking an eye. And I will not pay for my own coaching training." So it's incredibly complex, and it does us a disservice to just say, "Come on, women! Step up!" Because we are trained all our life. We're trained from childhood. I know even my own training was, "Don't shine too brightly. That makes people uncomfortable." I have to just share this one story. I adore my mom. She's the staunchest supporter, she's 92, she always said, "You can do whatever you want," but I was a top-level tennis player. All the boys, I was number one on the tennis team, the girl's tennis team. All the boys would wanna beat me, all my friends. So all my friends, I go out, and I wipe the court with them. And my mother would say, "Don't beat the boys. Don't beat the boys. They won't like you." These lessons get in deep. I do have to say, my therapeutic training, I don't do therapy in coaching, but I'm able to feel and hear when you've had messages from childhood that told you, "You better not shine." The reality is, you can't just superficially address this. You have to go inside, and you have to look at your mindsets and your beliefs, and you have to shift them, and that does not happen in a second.

24:11 KI: So I wanna shift a little bit to your book, 'Breakdown, Breakthrough,' and I know in the book you referred to 12 hidden crises working women face today, and how to overcome them. And love for you to tell us a little bit more about that, and your learnings there.

24:29 KI: When I began to write this book, which was a few years out of being in the corporate world, I truly thought I knew everything. Research never occurred to me. I thought I can write the book on crises. And I wrote a book proposal and showed it to a wonderful Janet Goldstein, an editorial consultant. She said, "Look, you're a fine writer, but this is not the big idea. I want it to be in the national conversation about women." And I said, "Really? Well, what is the big idea?" She said, "You have to research." And I truly left the meeting thinking, "What does she mean? Go to the library with index cards? I don't get it." And then, I used to do market research in the marketing world. I had this cosmic 2x4, "Wait a minute, I can interview 100 women." And this was really before social media made it so easy. And now, I can interview 1,000 people, really, at the drop of a hat. But I put it out there. I remember 9:00 AM, "I'd like to do a research study with women who have faced professional challenge and overcome it." I went down and had a cup of coffee, and I came back, and 50 women said, "I don't even know what this is, but I wanna do it."

25:33 KI: So I interviewed 100 women, and from that, what emerged are 12 crises that fall into four areas of disempowerment. And that word is kind of very overused, but I mean it. I mean that we have lost the ability to feel empowered. And those four levels are: Your relationship with yourself, others, the world, and your higher self. And I don't mean that religiously, I mean it as a spiritual concept. So in talking to these women, what started to happen was their story started to group into these 12 crises. Some of them are chronic illness, which I believe is inextricably linked with what you do every day. "I can't speak up, I can't break this cycle of mistreatment," and they were talking in that language, "I can't." "I can't use my real talents in life and work. I can't break out of this crushing competition." It went on and on. So after, I remember after interview 32, it really crystallized a model for change that formulated these crises into these groups. And what they offered was concrete strategies and exercises, practical things to do and think about to overcome these challenges. And I really do believe with that when you're stuck, it's very hard and very confusing to find a path that gets you unstuck, and that's what this book aims to do.

27:07 KI: Starting your own business, being an entrepreneur, is a leap. So what are your tips for inspiring entrepreneurs? And I'd also love to hear what was the hardest lesson you learned?

27:18 KI: So I went from therapist coach to, "Wait a minute, I wanna offer more services, products, programs." Just because you have corporate experience doesn't mean it applies. You're not immediately gonna hit the ground running as an entrepreneur. Very different. Get help, you need a very sound business plan and a transition plan. Do not just think that this is gonna happen. You need intense, competitive analyses. So let me tell you, I interviewed the head of AmEx OPEN a few years ago. I believe her name is Susan Sobbott. I asked her what are the differences between male and female entrepreneurs; and she's fascinating. She said, "Number one: When you ask a man why he started his business, it's about making money. If you ask a woman, it's almost always about, 'I wanna be of service.'" Well, it's awesome to wanna be of service, but you have to know how to make money as well. "Number two: Scaling. If you ask a man, do you think this can scale? And no male says 'no.'" Yeah, I see this huge. A woman will often, and not every woman, but will often say, "Oh, I don't know. I'm not sure." And that's often because a balance issue, they're afraid of it getting too big. They're afraid of delegating and doing what's required to scale.

28:39 KI: The third thing is numbers. Men are comfortable with numbers, and even if they're not, they often don't admit it. Women will say, "I'm not comfortable with the numbers. I've gotta hire someone." That's the kiss of death as an entrepreneur. You have to live and breath the numbers. So one of the big pieces of advice is you have to heal your money situation. Well, how you do money in your personal life is how you're gonna do money in business. You've got to get powerful with money. And there's a lot of tips about that. Heal your money story. A lot of women are not trained and comfortable with money, they have to be. So those are just some trends that I see. The biggest mistake I made was the wrong business model. I started as a one-on-one coach, and thought I could fill that pipeline. Well, I wanna make hundreds of thousands of dollars. That's a lot of coaching hours.

29:29 KI: There's only so many hours in a day.

29:30 KI: Right, now, Tony Robbins makes a million, I think, a client. Okay, I'm not there yet, but I realized, "Okay, this is not the right model," but I waited 'til I almost lost my house to open my eyes and say... But you know what? The signs are there. It's beleaguering to fill the one-on-one pipeline. I then, in the end, didn't want to do it but I waited too long to pivot, to get the right help. Another thing is look at role models who are actually doing something that's in alignment with what you want. I wasted a lot of time looking at online marketing gurus, only to wake up and say, "What? I don't want that. I don't want that."

30:15 KI: Yeah, and I do think that that gets back to your earlier point about knowing your numbers. So if you, when you're setting out to do your business, and you say, "Okay, here's how much I'm gonna charge per hour. Here's how many hours a week I'm going to be billing." Then there's other hours where you're running your business, you're doing sales, and prospecting, and everything else. So, "If I am booked 100% of the time, this is how much I make. If I'm booked 75% of the time... " And you really have to model it out, and look at the different scenarios, and then based on that, say, "Is this something that I'm comfortable with?"

30:55 KI: But there's a problem within that. Even when women do that, or men, they say, "Okay, I have to work 50 hours a week with coaching clients." What they don't understand is, for you to fill a pipeline, you have to reach millions of people, millions. And that is another thing. Today, in any venture, you have to leverage social media. You have to be a thought leader in many of these entrepreneurial directions.

31:19 KI: That all takes a lot of time and energy.

31:22 KI: You can't say, "I'll let someone else write for me." It's noticeable when it's not your authentic voice. Yeah, so I really don't mean to be doom and gloom; it's a beautiful world, it's so exciting. But you really have to know what the challenges are, and you have to get really expert help. And there's a lot of expert help that is not expert. I truly believe that everyone listening, and everyone on the planet is amazing, and has gifts that no one else has. And it's time now to do the inner work to pave the way for the outer success of knowing who you are, knowing what you have to offer, and being courageous enough to go for that.

32:05 KI: Thank you.

32:05 KI: Thank you for having me.


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