In this episode of The Rainmaking Podcast, Scott Love welcomes Jordana Confino, founder of JC Coaching and Consulting and author of the blog Chronicles of a Recovering Type A+ Perfectionist, to explore “The Perfectionist Paradox.” Jordana explains that perfectionism is not about high standards—it’s a fear- and shame-based mindset driven by self-doubt and the need to prove worth. She reveals how this approach undermines both mental health and performance, blocking creativity, risk-taking, and authentic business development. Drawing on neuroscience and positive psychology, she describes how to replace the inner critic’s harsh voice with self-compassion, rewiring the brain through neuroplasticity to enhance confidence and performance.
Jordana shares practical strategies to help high-achieving professionals and lawyers break free from destructive perfectionism. These include “drawing your critic” to externalize self-judgment, practicing compassionate self-talk, and identifying core values to shift from fear-based motivation to values-driven achievement. By replacing self-criticism with self-compassion and clarity, professionals can perform at a higher level, strengthen resilience, and enjoy greater fulfillment in their careers and lives.
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Jordana is a certified professional coach, speaker, and advisor, valued for her expertise in positive psychology and well-being, and her unparalleled ability to connect with and inspire everyone she meets.
Seven years after graduating from Yale Law School, Jordana founded JC Coaching & Consulting to empower lawyers and other high-achieving professionals to transform their lives and work for the better. Having spent the bulk of her career working as a lawyer and in legal education at elite institutions, Jordana knows that many high-achieving, successful people hold limiting beliefs that prevent them from truly flourishing. For many years, she was one of them. Jordana transformed her life leveraging the science of positive psychology and human motivation theory, and she is passionate about helping others do the same.
Jordana is an Adjunct Professor at Fordham Law School, where she previously served as the inaugural Assistant Dean of Professionalism. Jordana teaches a course on Positive Lawyering, which educates students on how they can harness the insights and science-backed strategies of positive psychology to reach their highest potential and build meaningful, satisfying careers in law. She also teaches Peer Mentoring & Leadership, a one-of-a-kind course designed to equip mentors with the tools and training they need to optimally support their mentees and emerge as leaders in the profession.
Jordana was voted Fordham Law Adjunct Professor of the Year in 2021.
Website: https://www.jordanaconfino.com/
Blog: https://www.jordanaconfino.com/subscribe
LinkedIn: https://www.linkedin.com/in/jordanaconfino/
Values Discovery Guide: https://www.jordanaconfino.com/values
Self-Compassion Guide: https://www.jordanaconfino.com/self-compassion-guide
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[00:00:10] You're listening to The Rainmaking Podcast, hosted by high-stakes headhunter, author, and professional speaker, Scott Love. You're listening to The Rainmaking Podcast, and my name is Scott Love. Thanks for joining me on the show today. Ladies and gentlemen, you've got an exceptional guest today, someone that's going to help you grow personally, not just professionally. And the topic that we're talking about today is the Perfectionist Paradox.
[00:00:40] And our guest is Jordana Confino. Now, Jordana is a certified professional coach, speaker, and advisor valued for her expertise in positive psychology and well-being, and her unparalleled ability to connect with and inspire everyone she meets. Seven years after graduating from Yale Law School, she founded JC Coaching and Consulting to empower lawyers and other high-achieving professionals to transform their lives and work for the better.
[00:01:07] This was probably one of the more impacting conversations I've had, at least with me personally, and I hope it gives you that same benefit as well. Because she really goes deep into what is the Perfectionist Paradox. Why do we have that? And how can you overcome that? I hope you get some great ideas from my conversation with Jordana today. By the way, connect with her. Go to the show notes, because we've got her blog, her website, her LinkedIn profile, her values, discovery guide, and her self-compassion guide.
[00:01:36] All of those are resources that I think can really help you grow. As always, our show is sponsored by SurePoint Legal Insights, formerly known as Leopard Solutions. Turn legal intelligence into opportunity. Also, we recently launched The Rainmaking Magazine. This is a digital magazine on Substack that we produce, curating content related to those in professional services that are responsible for earning trust with clients.
[00:02:05] If you're someone that is intellectually driven, results focused, and you expect a certain degree of credentials and credibility, then that online digital magazine is for you. Go to therainmakingmagazine.com to learn more. Thanks for listening to the show, and I hope you get some great ideas from my conversation with Jordana Confino today. Thank you for listening. Hey, this is Scott Love with The Rainmaking Podcast.
[00:02:31] Our guest today is Jordana Confino, and we're talking about the perfectionist paradox. Jordana, thanks for joining me on the show today. Oh, it's my pleasure, Scott. Thank you so much for having me. That's great. I'm familiar with your work through the National Association for Law Placement, so I'm excited to have you here today. And first, I want to get some definitions in place. When we say a perfectionist, what is that, and why is that a paradox? Yeah.
[00:02:58] Well, I'm very glad that you're starting with this question because often when people, especially high-achieving professionals, hear the word perfectionist, they think, oh, that's the gold standard. Drive, determination, commitment to excellence, super high standards, meticulous attention to detail, all of the things that I need to excel in my job. But perfectionism is actually separate from all of those things.
[00:03:26] It is actually a fear and shame-based approach to achievement, where basically it comes from a fundamental feeling of self-doubt and insecurity and desperation to prove your worth.
[00:03:43] And so you're striving to achieve in order to validate yourself and prove that you're worthy, as opposed to striving for excellence for the sake of excellence and honoring that value of drive or determination or learning or growth that you have. So that is one distinction. Another very important distinction is the extent to which we accept or reject reality.
[00:04:10] So perfectionists will strive for total perfection and reject the constraints of reality, whereas what I like to call people who are non-perfectionists can accept those and work with them to achieve the most perfect option that's actually available. And then the last critical piece about perfectionism is how we treat ourselves as we're pursuing our goals.
[00:04:35] And so, again, that shame and fear and discipline, harsh discipline-based approach versus a values-driven and really intrinsically motivated, caring approach towards goal pursuit. This is interesting. So if I had known you're going to start our show off to the target market of high achievers, lawyers, people in private equity, finance, people that do deals.
[00:04:59] If you're going to start it off with fear, shame, self-doubt, and desperation, I'm like, I don't know if we should talk about this. But it seems like this is pretty important. So I would not have expected that. Can you talk more about fear, shame, self-doubt, desperation? Why is that a big part of perfectionism? Yeah. And if you're listening, please don't run away. If you haven't yet, it's so important.
[00:05:24] Because perfectionists think that they're going to render themselves invulnerable by just pushing harder and motivating them with this fear, shame, and blame. But they think that that's actually what makes them stronger and beyond reproach. And the problem is, well, the problem is twofold, at least. One, that destroys our mental health and well-being.
[00:05:48] And we think that we're hustling to achieve these outcomes that will bring us that feeling of security and confidence we crave, when the truth is, is that we're just perpetuating our insecurity and making ourselves more anxious and insecure by the moment. But let's put that aside and say we don't care about our health, our happiness, our well-being.
[00:06:08] And very ironically and counterintuitively, research shows that this fear and shame-based approach to achievement and goal pursuit is actually not very effective. So we have all been, not all, most of us have been raised to believe that the harder we drive ourselves and the more we try to whip ourselves or beat ourselves into submission, the better we'll perform. And that's actually not true.
[00:06:35] And there's an abundance of research showing that when we are doling out harsh self-criticism or stoking ourselves with self-doubt, we actually inflame the emotional part of our brain that encapsulates that shame and that anxiety and that fear so much that it consumes all of our brain's processing power and turns off our prefrontal cortex, which is a part of our brain that governs rational thought, and sends us into what they call amygdala hijacking mode,
[00:07:03] whereby we become completely consumed by our emotional reactivity and our shame and our doubt and actually lose our capacity for rational strategic thought. Contrast that with if we learn how to be kinder to ourselves and not be beating ourselves up on the inside, we can actually settle our nervous system, keep our rational thinking brain online, and strategically determine how to achieve the best possible results.
[00:07:31] Also, and I think this is especially relevant for this podcast because rainmaking, that involves business development, obviously, which is a higher and very different level of work than what most people who want to be rainmakers did to succeed in order to get to where they are. So there's, in the legal industry, for instance, there's a very big difference between being a rainmaking partner and what you need to be able to do that to being a stellar worker bee associate.
[00:08:01] And that higher level business development work, like other higher level work, requires so much more creativity and also risk tolerance because you have to be willing to put yourself out there and make yourself vulnerable, which is terrifying. And perfectionist, they are so focused on, I need to look perfect. I need to, you know, come across as completely together and perfectly execute that they don't like doing anything
[00:08:30] that stretches them or subjects them to any form of vulnerability and risk. Because in their mind, if I make a mistake or if something doesn't go perfectly or if I get rejected, that will show everyone that I'm not good enough. And so what they do is they hold themselves back. They stay in their comfort zone and no one ever becomes a rainmaker inside their comfort zone. That's right. So it's really, really important to recognize these things. Because if we talk about the fear and the shame, it doesn't mean they're not there. It just means that they're running the show.
[00:08:59] That's right. So I like the fact that we went pretty deep right away, even going to the science-based approach of why these things happen and the impact it has on us. Before we talk about how listeners can manage these issues, let me ask you this. Have you met somebody, I wouldn't say they've got it all together, but they're doing really well in terms of their mental health. They're performing at a high level. They've learned how to manage the fear, doubt, shame, etc. Maybe we could talk about that person.
[00:09:28] How would you describe that? Maybe call that an avatar or maybe it's someone that you've actually met. You're looking at her. My book is called Chronicles of a Recovering Type A Plus Perfectionist for a reason. When I was a practicing lawyer, I was a raging overachiever and perfectionist who truly believed that the road to success involved running myself into the ground
[00:09:54] for the purpose of my work and tearing myself to shreds along the way. And it seemed to work really well at first until it stopped. And that, it stopped, it really stopped. And I had hit my mental, emotional, physical breaking point, all of the things. And that set me on a very winding road that led me to doing the work that I'm doing now.
[00:10:19] And it took years, but I learned how to rein in that really toxic perfectionism that I saw, I came to realize was holding me back and sabotaging me. And I will say, when I first learned the brain science behind all of this, I was like, oh my gosh. But one, these, I am, you know, off the charts in terms of all of these aspects of perfection in mind I told you about.
[00:10:48] And now I'm seeing, oh wow, like I thought this was helping me. I thought this was necessary. But actually, it's so destructive. There was a point, it was about a year or so, where I walked around describing myself, basically to myself and my therapist, as spoiled goods. I thought that because of my upbringing, which, you know, laid the foundation for this very deeply internalized perfectionism, I was a lost cause because this stuff was just so deeply ingrained in there.
[00:11:15] And then I learned about neuroplasticity, which is the human ability to literally rewire our brains through practice and concerted effort. And I have been doing that ever since and have gone from here to here. And do I want to be up here? Yes. And then some days, am I here and here? Yes. But the difference is mind-blowing. And now, first it was me.
[00:11:43] And now that's what I deal with all of my clients because I specifically focus on working with high-achieving perfectionists who need to get out of their own way. Because given my history and my training, I feel like that is really the person I'm best suited to serve. And so, yes, I have that avatar. I know a hundred of them. That's great. That's great. When did you know, when you started growing in that area, when did you know you were really making progress, Jordana?
[00:12:13] Oh, wow. It was actually way sooner than I thought. Because we'll talk about some of the most important first steps for beginning to reign in the perfectionism. And one is beginning to cultivate self-compassion, which is learning how to basically relate to yourself like you would a dear friend if they were in your shoes rather than just tearing yourself apart as many of us are naturally inclined to do.
[00:12:44] And when I first started practicing self-compassion, and literally the way that you do it is you come up with self-compassionate thoughts that you, well, this is the couple steps in, but you, this step, you come up with self-compassionate thoughts that you do not believe all at this point. And you literally start practicing them. And... Like with mantras? Like, it's kind of like a mantra, but you, it's not in the first person. So it's not like I am, I can.
[00:13:12] You speak to yourself as if you were another person. So for instance, like Jordana, I know you were super anxious about this assignment. I used to have raging writer's anxiety. So it's a journal, I know you're super anxious about this. You've written amazing things before. I know you can do it. Let's just take the pressure off. Try to write something. You can always edit it later. You've got this. Rather than, this is going to be such a disaster. Do, do, do, do. What do you think?
[00:13:38] And what research shows when we speak to us ourselves in that second person voice, it actually activates a different part of our brain than the part of our brain that is activated when we do mantras. So if I said, I can do this. I'm a great writer. I am strong. And it activates the part of our brain that is activated when someone else speaks to us. And we take other people's reassurance more seriously than we take our own. And so when you practice this, you practice these thoughts when you do not believe them yet.
[00:14:08] And the wild part is that so neuroplasticity, basically they say neurons that fire together wire together. And this is because every time that we perform an action or think a specific thought, the connection between the neurons that fire to facilitate that thought literally grows stronger, making it easier and more instinctive for us to think that thought again. This is why our self-critical and our self-doubting thoughts are so sticky because we've been thinking
[00:14:37] them on repeat for decades. But if we can learn to, and we'll talk about this other step, see that inner critic when it arises and see those self-critical thoughts, mindfully observe them, give that little critic a hug, thank you for trying to help, but then turn the volume down and replace them with self-compassionate thoughts. Even when we don't yet believe them, those thoughts will start to slowly, but not that slowly, get stickier and more instinctive.
[00:15:07] So going back to our initial question, I started doing this and I started writing it out, dialoguing with my critic. And I would say within a month, I was seeing those self-compassionate thoughts, which when I started doing this were so hard for me to pull up and I was writing them down being like, this is ridiculous. I don't believe it at all. Popping up as plausible alternatives all of a sudden, within a month of practicing this and then they were getting stronger. And it's so bizarre.
[00:15:34] It's almost like we only have so much radio band wavelength in our head. And so if we grow that self-compassionate voice by practicing, it pulls the power away from those self-critical thoughts. So we still see the critic pop up, but we can see it and then separate ourselves from it. Whereas most perfectionists, the critic just like washes us away in this tidal wave of shame or gives us this anxious directive saying, you must do this in order to get rid of this
[00:16:03] anxiety I feel. And the problem is that usually its directives are not actually constructive. And so if we grow the self-compassionate voice, one, we prevent ourselves from getting lost in those spirals of shame, self-doubt, what is it? And we can also see that perfectionist directive and ride the wave of our anxiety or surf the urge of our anxiety recognizing, oh, I don't have to yield to that command.
[00:16:29] I can actually make a wiser, more intentional values and logic-based decision rather than giving into that impulse. And the word impulse is really important because what perfectionism really is, it's almost like an addiction to achieving and perfecting and performing. And in moderation, that's good. But when it gets on overdrive, which it is for perfectionists, then it becomes harmful.
[00:17:00] I think you've hit on several nerves for a lot of people listening, myself included. I hear this and I'm like, wow, what a great idea. What a great idea. What a great idea. I like the fact that these are simple things people can do. I'm proud of you for what you've done and the impact you're making for other people, Jordana. Yeah. And I like the fact that this is a vulnerable thing that a lot of people are dealing with all the time. And it's like you're giving people permission to give themselves grace. And I like the fact that it's-
[00:17:29] Not only am I giving them permission, I'm giving them a prescription because I always speak to the professional who doesn't even care about their health and happiness. They just want to perform because the people who care about their health and happiness, they absolutely should. I care about your health and happiness. I care about my health and happiness. But when I needed this the most, I didn't care about my health and happiness. I just wanted to perform. So even if you just want to up your game, give yourself grace because it will actually
[00:17:56] make you better at everything that you want to do, which is so counterintuitive. So thank God we have actual science proving it because- Right. Otherwise, I wouldn't have paid attention. So what are some of the other building blocks of your formula, so to speak? You talked about giving ourselves, how did you entitle it? Self-compassion, is that coming? Self-compassion. So there's a couple steps to this. I shared one. The first thing I want to do, it's going to sound so woo-woo, but I promise you it is backed by hardcore neuroscience.
[00:18:24] I want whoever's listening to this, if it's resonant to you, I want you to actually draw your inner critic slash voice of self-doubt. So imagine that loop of blame, shame, catastrophizing criticism that's going all day and close your eyes and just imagine a little being that is in there screaming at you, these admonishments,
[00:18:50] and then actually draw that little person thing, whatever it is, however you personify it, draw it. Because what this is going to help you do is when it pops up, when you hear that, you didn't do that good enough. What is wrong with you? Or you're not going to be able to do this. You know, this is going to be such a disaster. Everyone else is better than you. Any of those things. Or you're weak. You're lazy. Whatever. When you hear that, then you can start imagining that voice coming to you from this separate
[00:19:20] being. And that creates the psychological distance that will empower you to separate yourself from that thought and recognize, okay, that's an anxious thought. That doesn't mean it's true. That doesn't mean it's fact. It certainly doesn't mean that it's constructive. And in all likelihood, it absolutely is not. And then choose to show yourself some compassion in that moment. And we'll talk about that in a second.
[00:19:48] And just settle your nervous system, which will then empower you to take a step back and take the most constructive action. And what I want to say is, so step one, draw the critic. It's going to sound ridiculous. I can't tell you how many very high up partners have begrudgingly done this and rolling their eyes the whole way. Fine. And then email me being like, oh my gosh, this was so helpful. I'm just so powerful. Well, that's the first step.
[00:20:16] And I want to just make clear, self-compassion is not self-indulgence. Self-compassion does not mean I just made a big mistake, but I'm perfect. It was wonderful. You know, like Pollyanna rose-colored glasses. No. There is always value. If we just want to come out the way that we want, we can say, oh, I messed this up. I'm feeling really bad about myself right now. That's a really normal reaction to this. I'm not the only one that's ever messed something up.
[00:20:47] And this is not going to destroy me. I will be able to get beyond this. This does not make me a horrible lawyer, professional, whatever. And then that is very different than, oh, this is perfect. I'm great. You know, just carry on. It's also very different from, that was terrible. What is wrong with you? You don't deserve to be here. No one's going to want to work with you again. You should just give up now. And what happens with that latter response, then you feel ashamed, demoralized, defeated.
[00:21:17] What are you not doing? You are not taking a step back, looking at that situation and determining, well, how can I, you know, rectify this and make the most of this right now? And also, what's the lesson for next time? That is exactly what you can do if you give yourself, show yourself that self-compassion. You validate the hard feelings, but you don't, you know, swoop them up into a shame smoothie.
[00:21:39] And then your nervous system relaxes, your rational thinking brain stays on, and then you can take that constructive action. So that is step one, drawing the critic. Yeah, right. Step two is the self-compassion. So giving yourself the encouragement and support that you would show to a friend. And step three is practice, practice, practice, practice, practice.
[00:22:03] And so a great way to practice this is by practicing it when you're not in the heat of the moment. So practice just writing compassionate messages yourself in the morning and at night so that when your critic pops up, it's a little bit easier for you to access in real time. Are there any other examples of compassionate messages that people should give to themselves? Oh, yeah. I mean, it really, it really depends.
[00:22:30] I mean, give me a scenario and I'll give you a compassionate message because it's not, the whole point is, it's not just, it shouldn't just be blanket mantras or affirmations. It's really, it should go to the things that are really coming up for you. So what I say when I'm encouraging people to practice, I say, think about, usually people have their tender spots where like there's someone thing that I'm really insecure about,
[00:22:59] or there's something I have brain imposter syndrome about, or like there's something I've been tearing myself apart about for the last, gosh knows how many days. Think about that thing. And then on those things that are real for you, not just, you know, generic, give yourself compassion. So if you give me an example, I could, I could give one for you. I don't know.
[00:23:22] I mean, there's so many of them out there, but I like the fact that the whole concept itself, I think it just lets us give our, get ourselves off the hook, so to speak. I can give you an example. So this is one, for instance, we'll think about business development type things. Sure. But like I mentioned, I have writing anxiety. And also whenever I post something on LinkedIn, I feel like I'm going to vomit afterwards, which I think is really normal.
[00:23:50] And I never, ever, ever thought that I would start a blog or anything like that for these exact reasons. And interestingly, as I did the work on my perfectionism, I saw my creativity and also my courage bubbling up. And I sort of, and I sort of wanted to share them more. And, but still, I get this huge imposter syndrome and anxiety. So something around this, when my inner critic is anxious and stressed and saying, no one wants to hear from you. You have nothing interesting to say.
[00:24:20] You're a bad writer. Everyone's going to see it. They're probably going to think your post is stupid. Da, da, da, da, da, da, da, da, da, da. Even just compassion would be, Jordana, I know that you're nervous to post on this because you worked really hard on it. And you're scared that people are going to judge you and think that you're less than. And, you know, that will make you feel kind of worthless, useless, you know, not, not good enough.
[00:24:49] And I also know that basically for your entire adult life, you've been feeling like you're kind of getting one over on everyone and feeling like you're somehow sneaking in and looking good, even though you don't actually deserve the credibility and the legitimacy you've given. Those are such normal thoughts. Do you know how many people believe them? So many. And do you know that the strength of those thoughts is in no way correlated with their accuracy? C-E-G, Michelle Obama has imposter syndrome.
[00:25:17] So please know that you have so much value to add and that people will benefit from reading this post. And even if just one person benefits, this will be worth it. So I am so proud of reading this. You can hit post on this. That's great. As opposed to sitting there and just spiraling in my, well, what if they think this? And what if they think that? And what if they think this? Because guess what? Then I'll never hit post.
[00:25:45] And then no one will ever know what I do. And no one will ever find me. And I'll never generate business. And, you know, there goes rainmaking. Yeah. Well, Jordana, I feel like we're just scratching the tip of the surface. And I know there's so much more to talk about, but we're running out of time on our show. So I want to have you back on here in the future to kind of go deeper on this with me. But in the meantime, if we could kind of summarize this like three action steps, like you talked about, if people want to start on this and their journey to increasing their mental health with this issue,
[00:26:14] the perfectionist paradox, how could you summarize that in three action steps, so to speak? I'm going to recap two, and I'm going to give you a new one. So one, draw your critic. Draw your critic and start imagining that voice coming from this separate being. Two, start giving yourself these self-compassionate messages. Again, you won't believe it. Imagine what you would say to a dear friend in your shoes and practice even when you don't believe it. Over time, it will grow stickier. The critic's voice will get less powerful.
[00:26:44] And the third one is, and this is different. We haven't talked about this yet. Identify what your core values are. So what is really most important to you? Because perfectionists often lose sight of their values because they become so consumed by their fear. And so perfectionists are never really playing to win. They're always really just playing not to lose.
[00:27:10] So they're playing to avoid feeling more shame and anxiety than they're already carrying around with them. And that's a really unsatisfying feeling because we never actually feel that pride and achievement. When we get something, we just kind of recalibrate, feel some relief that we didn't fail and embarrass ourselves, and then set the goalposts further.
[00:27:30] But if we can identify what our core values are, which is different from our fear of failure or fear of not looking good, and set that as our motivation for whatever we want to do in our work. So whether it's growth, whether it's providing for our family or love, or whether it's learning or leadership, whatever it is. And we set that as the goal, as opposed to avoiding embarrassment or avoiding failure.
[00:27:56] Then we can actually start playing to win as opposed to just this playing not to lose. So that's the last step because I've been telling you what not to do, what not to strive for, what not to do. But how can we still motivate ourselves? And it's through that values-based motivation that we can push ourselves to excel, but in a different way, which is not only healthier, but also actually way more effective. That's great, Jordana. And tell us and our listeners about your services, your offerings. What do you have?
[00:28:26] What do you do that you'd like for people to know about? And for everybody listening, make sure you connect with Jordana on the show notes wherever you listen to this podcast. Sure. So I do one-on-one coaching with high-achieving professionals who want to rein in their perfectionism, get out of their own way, and just enjoy greater satisfaction and sustainable success in their lives and work.
[00:28:50] And I also do trainings on reigning in perfectionism as well as positive psychology for well-being and peak performance more broadly. So if you're interested in coaching or training for your organization, please reach out. And then also I have my blog, Chronicles of a Recovering Type A Plus Perfectionist, which is basically exactly what it sounds like. And it's where I share my tools and strategies for all of these things that we've been talking about.
[00:29:18] And so you can find all of that on my website, as well as a self-compassion guide and a values discovery guide, which will help you with those steps that we just outlined.
[00:29:58] That's terrific. For more international law firms, visit our website at attorneysearchgroup.com. To inquire about having Scott speak at your next convention, conference, sales meeting, or executive retreat, visit therainmakingpodcast.com.
