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Practical and actionable information you can use to be a better lawyer.

The Resilient Lawyer podcast is inspired by those in the legal profession living with authenticity and courage. Each week, we share tools and strategies for finding more balance, joy, and satisfaction in your professional and personal life!

You'll meet lawyers, entrepreneurs, mentors and teachers successfully bridging the gap between their personal and professional lives, connecting the dots between their mental, emotional, physical and spiritual selves.

This podcast is about ordinary people making an extraordinary difference.

Dec 6, 2017

In this episode, I am excited to have Karen Gifford on to discuss co-writing our book, The Anxious Lawyer, her wellness routine, and life after law. Karen Gifford is COO of Ripple Labs, global leader on distributed financial technology. Previously, she worked in the financial industry, first as an attorney in the private sector and at the Federal Reserve Bank of New York, where she was Counsel and Officer in the Litigation and Enforcement Group. Alongside her legal and consulting career, Karen began meditating in a yoga tradition more than fifteen years ago, initially as a means of coping with the stress of her legal practice. Her executive coaching work incorporates meditation and mindfulness practices, placing a strong focus on the importance of inner skills such as detachment and resilience for effective leadership. She also teaches meditation, with an emphasis on bringing the insights of meditation into everyday life. Karen is active in the start-up world as a founder, investor and advisor. She holds a J.D. from Yale Law School and an A.B. from Vassar College.

Topics Covered

  • Karen tells us on her writing process with The Anxious Lawyer, her thoughts on the end result, and how living at a meditation ashram helped her find her inner quiet, which helped formulate the thoughts for the book.
  • How the internalization of the job that can lead to feeling burnt out and stuck in your career, and the importance of a wellness practice to create space and distance to stay motivated and vigilant.
  • The impact that distance and awareness can have on self-reflection, both personally and professionally.
  • Life after law: Finding joy in your work, always remaining sensitive to where you stand instinctually, and always looking for the obvious answer when it comes to making a transition in your career.


Questions? Comments? Email Jeena! You can also connect with Jeena on Twitter: @Jeena_Cho

For more information, visit:

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Karen Gifford: [00:00:03] Joy doesn't have to express itself with puppies and rainbows and flowers, it can also express itself in a great argument or a beautifully presented witness.

Intro: [00:00:18] Welcome to The Resilient Lawyer podcast. In this podcast, we have meaningful, in-depth conversations with lawyers, entrepreneurs, and change agents. We offer tools and strategies for creating a more joyful and satisfying life. And now your host, Jeena Cho.

Jeena Cho: [00:00:44] This is The Resilient Lawyer podcast, meaningful, in-depth conversations with lawyers, entrepreneurs, and agents of change. The Resilient Lawyer is inspired by those in the legal profession living with authenticity and courage. This podcast is about ordinary people making an extraordinary difference. This is episode number 37, I am your host Jeena Cho. Hi everyone. It's been forever since I recorded my last podcast, but I've been very busy with the launch of "The Anxious Lawyer" book and I have in studio with me Karen Gifford, my co-author.

Karen Gifford: [00:01:18] Hi Jeena, it's so great to be talking about our book together.

Jeena Cho: [00:01:24] I know, it's been such a long journey, it feels like.

Karen Gifford: [00:01:27] It sure has, it sure has. And it's just an amazing feeling to be not coming to the end of it. I don't think this is the end. But getting to the end of the work, of reading the book, creating the audio recording, going out into the world and talking about the book, that sort of thing.

Jeena Cho: [00:01:49] Yeah. So how does it feel to you?

Karen Gifford: [00:01:52] Well you know, when I first started practicing law one of the partners I worked for said about going to court, he said there's the argument you were going to make, there's the argument you actually made, and then there's the argument you would have made.

Jeena Cho: [00:02:07] Yeah.

Karen Gifford: [00:02:07] And I was thinking about that with the book, and I was thinking you know I do feel a little bit like I go back and read the book and I think, oh I should have said this, or I should have said that. But all in all I'm happy with it. I don't have a big feeling like it should have been very different from how it ended up being. We were talking earlier and discussing the fact that doing the audio recording has brought us back into closer relation with the content of the book. And as I read it, I really enjoy reading it. I like what we said, and I appreciate the insights that you have in the book, and I'm happy that I remembered to say some of the things that I wanted to say. So it's good, I'm feeling pretty happy.

Jeena Cho: [00:02:56] What was the writing process like for you?

Karen Gifford: [00:03:01] Well, the writing process really had two big parts to it for me. So when we first started out writing, I got into a nice rhythm where I was getting up early and writing for three hours every day. And that was pretty wonderful, I get really sweet memories of doing that. Then maybe six months into that, I had a big interruption there was a big crisis at my office, and you and I had talked about that and I just completely got pulled away from writing. And that's pretty stressful because the work situation was quite stressful, and I also felt like I was neglecting this thing I cared about a lot. And that was rough. And then getting back into writing again, I actually felt like a relief after that, when I finally had time again. It was just nice to be doing something that I liked and cared about and was sweet, instead of dealing with a lot of crazy work crisis issues.

Jeena Cho: [00:04:09] Yeah. Is the writing itself sort of peaceful? Did you feel like the content sort of flowed out or was it is a struggle to try to find the words? What was that process like?

Karen Gifford: [00:04:22] A lot of it really flowed. I think early on, you and I spent a bunch of time laying out the chapters and talking about the things that we wanted to cover, and also talking about how we wanted to frame what we were doing. And I think that was the important work, and it was really useful. I had never really had a chance to talk about meditation practice with another lawyer in so much depth as what you and I did. We had so many meetings over coffee, meals and stuff, and talking about not only our experience of starting to meditate while practicing law, but also the reactions of our colleagues. And who was excited by it, who was really like weirded out by it, why we thought that might be the case.

[00:05:14] Once we had talked all that through and talked about the way we wanted to present meditation to lawyers, so that maybe they wouldn't have to face some of the barriers that we faced when we got started, the writing itself I guess came pretty naturally.

Jeena Cho: [00:05:32] Yeah, well I guess for the listeners that don't know you, might be helpful to give them a little bit of a background, just in terms of like what you've done throughout your career and the work that you're doing now. I think you talk your career transition in the book, but I don't know that too many people actually know what you do now.

Karen Gifford: [00:05:55] I practiced law in the private sector, I practiced at a law firm for a while when I first graduated from law school. And then I was at the New York Fed for quite some time, for eight years doing civil litigation on behalf of the Fed and also civil enforcement actions, bringing of enforcement actions. Which is pretty similar to what the SEC does. It's bringing enforcement actions either against individuals or entities who've broken the banking-related laws in one way or another.

[00:06:31] So I did that for quite some time and then left and ended up doing regulatory consulting after moving from the East Coast to the West Coast, and worked for a boutique consulting firm doing that for quite a bit of time. And after the financial crisis I just really got burnt out doing that. I felt like some of the changes I was hoping to see in the financial industry were just really taking a long time.

[00:07:05] Especially, you do a consulting project and then you leave so you don't know what happened, you come back maybe to the same company or a similar type of company, and you see the exact same issue again. And it gets discouraging. So I left consulting, maybe like five years ago now. Since then have just been doing some investing in a small way, in the FinTech industry. And also advising, spent about two years working on the management team of FinTech company, getting their compliance program set up, also helped recruit a general counsel, kind of help to get the control side organized. So I wrapped that up maybe a little over a year ago now. And so I'm now just doing advisory work and working on the book, which has been terrific.

Jeena Cho: [00:08:08] OK so when you talk about FinTech, what does that mean?

Karen Gifford: [00:08:11] What does FinTech mean? You know that's a great question also, because it means a lot of different things to different people. So you could say PayPal is a FinTech company, because it offers financial services using technology. And really everyone uses technology, even if you're using an abacus that's technology. But delivering financial services through electronic means is really what is meant by FinTech. And I got attracted to working in FinTech because I saw a lot of really entrenched problems in the financial industry.

[00:08:51] In the case of Ripple, the company where I was working, around payments and how payments are executed, the way banks do it today is really slow. It's got a lot of operational problems, it's expensive. It makes it hard to serve the people who are poorly served by the banking community. And a technology like the one that Ripple has really represents a major improvement, a major step forward, particularly in being able to do kind of small value, high volume payments. Which is what we need if we're going to serve the billion people who aren't in the formal banking system today.

Jeena Cho: [00:09:44] So there's a billion people that don't have access to checking, savings account and what we typically consider as access to financial services?

Karen Gifford: [00:09:51] Up until last year, people were saying there were 2 billion people who were capable of having a bank account, who are adults with a financial life who didn't have one. And I think there have been some pretty big strides, particularly in India, about getting people into the formal financial sector. So it's not 2 billion any more, but it's more than a billion.

Jeena Cho: [00:10:14] Obviously in the book you talk about how you sort of started your mindfulness practice. But I feel like there's parts of your story that didn't make it into the book, like you lived in a yoga ashram for some period of time. Like how did that come about?

Karen Gifford: [00:10:29] How did all of that come about? Spending time at the meditation ashram came about really through my husband, who this particular retreat center, they wanted to change their business model around a whole lot. Which sounds like a funny thing to say about a meditation retreat. And I think it was funny for them, but they had been very big and had thousands of people coming to stay there every year. And what they were finding was it had gotten bigger than they wanted it to be, and just having it be quiet and a place where people can come and be contemplative and really build their meditation practice had started to be threatened by the size of the center itself.

[00:11:20] So they were trying to downsize, not because they were having problems but because they had kind of drifted away from what they felt their core mission was. So my husband has an MBA, so he went to help with that. And it was outside the city, we were living in New York City at the time. So I really had a chance to go, I mean I did do some work in the communications department but I wasn't really.. compared to having a full-bore litigation practice, it was a chance for me to really step back a little bit. And it was terrific. It was terrific.

[00:12:02] And also while we were there, even though we're both doing some work and we had kids who were in school so there's a lot of ferrying children back and forth and the normal responsibilities of parenting, we also did get to follow the ashram's schedule, which involved daily meditation practice twice a day, a lot of quiet. There was one TV set in the whole place, you know people talked about whether we would turn the TV on or not, mostly not. There weren't a lot of magazines. It was really a very, very, quiet place intentionally so, and that was terrific. That was terrific. One thing that I experienced when I was there, and I know you're going on an extended retreat coming up next year so we'll have to compare notes.

[00:13:00] But one of the things I experienced, was when you do the same thing every day, when you are on the same schedule every day, day after day, and you're not getting a lot of outside stimulus and the kind of stimulus of every day, the internet, television, movies and even newsprint media that way. After a while, your mind gets really quiet. And in a way that I had never experienced, maybe as a kid but certainly not as an adult. And it was lovely. It was a very, very sweet experience.

Jeena Cho: [00:13:41] You say your mind becomes quiet. What does that mean, what does that feel like?

Karen Gifford: [00:13:46] So, if you notice how your mind is most of the time.. most of the time, even though you and I are talking right now, both of us I'm sure I know, if I pay attention I can see this. My mind is going, I'm thinking about what we will say next, what time I have to get home, how much studio time do we have. All of these thoughts are just kind of in the background, it's not like they're taking up my attention particularly but I know they're there. And they're just kind of buzzing you know, all the stuff that's been in the news in the past few days with the election.

[00:14:26] There's just this whirl of thoughts in the background, and I always thought that was just the environment of a mind. And it is, it's fine. There's nothing wrong with that, but it's great and lovely to experience a mind where your thoughts are whirling less. And there's just more space between each thought, kind of like when we closed the doors of the recording studio and we were both noticing how lovely and quiet it was in this room, it's kind of like that.

Jeena Cho: [00:15:00] Yeah, yeah. And I always feel like these types of experiences are really difficult to try to explain in words to someone that hasn't had it. It's like trying to explain how does meditation change your mind or how does meditation feel in your own mind. It's hard to describe it in words.

Karen Gifford: [00:15:22] It's true, it's true. Because it's just like any felt experience, right? One of the things, an analogy that I have is the taste of ice cream, right? You can describe it as much as you want, with as many words as you want, but until somebody picks up the spoon and tastes ice cream they don't totally know what you mean. And the experience of having your mind get very quiet is a very particular experience, and you can ironically use words to describe it. But it's in the experiencing that it really becomes clear.

Jeena Cho: [00:16:04] So you've obviously gone through a lot of career transitions, and big career transitions really. And I think you and I have had conversations about this, but how do you think your meditation practice helped you through those pretty big transitions, or life transitions?

Karen Gifford: [00:16:24] Oh I would definitely say it helped me, probably the biggest change that I made in terms of how it felt was to stop practicing law from practicing law. I was very, very identified with being a lawyer.

Jeena Cho: [00:16:39] As most of us are, yeah.

Karen Gifford: [00:16:42] Yeah, I don't know what it is about practicing law, probably practicing medicine is similar. It takes up so much of your day and also your mental space, your energy, and it's such a peculiar stance towards the world, right? That after a while you just start to identify so deeply with like, I am a lawyer, I fight for my clients. The whole framework just gets internalized, and for me to step away from that was really difficult, way more so than I thought. You think on a day when you're frustrated, you've had a fight with your opposing counsel, that's it I'm never doing this again. But then to actually stop doing it, you're not just giving up that fight with your opposing council you're giving up a whole you worldview really.

[00:17:42] So I was surprised by that, I wasn't thinking about the fact that that would feel so big. And my meditation practice I think gave me spaciousness around it, and let me see that being a lawyer is an idea. It's not real, it's not a room that you literally move into. It's just something, it's a room you've made in your mind. And you can walk out of it and you're still all the qualities that you think of yourself as having, you still have those qualities. I think also another thing I went through is thinking, okay I'm never going to work again. I think a lot of litigators go through that, because we're jacks of all trade. We don't really know anything deeply. I used to say I only know something if somebody's been fighting about it.

Jeena Cho: [00:18:38] Which is so true, yeah.

Karen Gifford: [00:18:39] Right? And I thought, well who wants a regulatory lawyer? I'll never find a job doing what I was doing, and that turned out to just totally be my own trip. It was actually pretty easy to find work, and I didn't even know that regulatory consulting was a thing. But it's actually a pretty big thing that happened during the time I was practicing law. So it wasn't just my thing, my meditation practice made me open to trying something and realizing the difference between not knowing what was going to happen and disaster happening, right?

Jeena Cho: [00:19:31] Right, your mind thinks, oh my god I'm never going to work again, I'm going to become homeless. But that's not the reality of the situation, yeah. So when you decided you were going to leave law, was it a particular moment or was it a transition, or was it a set of experiences where you were like, okay I think I need to leave. And then a year later, you finally made that decision. How did that process come about? Because I feel like this is something that I talk to a lot of lawyers about. They sort of know that being a lawyer is no longer the right career for them, but they don't know what's after that so then there's that fear of what am I going to do, what's my livelihood going to be? And I guess I'm curious about that decision-making process. Or maybe it's a felt experience, I don't know.

Karen Gifford: [00:20:23] It certainly was a felt experience, for sure. And for me, it was something that unfolded over some time. So, part of it was trying to reconcile legal practice with parenting. So I was doing litigation, so there were always all these deadlines and I had done this big trial and promised my family that I was going to have time for them after the trial was over. Well, no sooner did I come back from doing the trial than six weeks later I was at this pre-trial conference that was meant, I thought was a scheduling conference. So we were going to be talking about something that was going to happen in a year, and my opposing counsel gets up and is like, "We want this to go right now!" And I was like, whatever. And the judge is like, okay fine, you're on for in two months. And I just watched my whole life, all my plans for hanging out with my kids and everything, go up in smoke. So that was big, that was a big part of it.

[00:21:38] And then, I tried working part time and I didn't really like being a part time lawyer for a lot of different reasons. So that was that was going on, and then also I think this is a big thing that happens with lawyers, we just get to a point where we've done what we've come to do in practicing law. I had done a couple of big trials and some smaller ones, and I'd written a lot. I'd written a lot of briefs, I'd written position papers, written speeches for different Fed officials, and it just felt like it was of a piece, like I wasn't going to make it more complete than it was.

Jeena Cho: [00:22:30] Yeah, yeah that makes sense. Yeah. And I think just that knowing requires a lot of awareness you know, almost like a day-to-day or week-by-week. So many of us just end up in this habitual pattern, where we just get up and do the thing that we're supposed to do. And all of a sudden years go by, and then we wake up one morning like wait. We don't really pause to assess our life and actually have those kinds of reflections. I mean for me, that's where sort of the day-to-day, having that moment of quiet has been super helpful because it's not like I get up one morning and think, I think I'm going to quit practicing law today. But you're actually making a little bit of space to have those thoughts about, oh well you know like what you said, now I feel like the work that I came here to do feels more complete than it did a year ago or two years ago.

Karen Gifford: [00:23:26] That is such a good point, that is such a good point. I certainly have that tendency to just get caught up in the day-to-day, and not step back and sort of look at what am I doing. That's probably one of the biggest changes that meditation has brought in my life, and it has so many implications. Certainly for career, and also for relationships. In terms of seeing my own nonsense, you know? They pay me to fight, right, so like I'm a righty person so I'd always want to be right with my spouse or my kids.

[00:24:07] And stepping back from that and going, wait a minute. Just look at this from the other person's perspective. I wasn't that capable of doing that years ago, and I feel really happy that it's not my first instinct, but it does it does come up. That, oh this other person might have a point of view here.

Jeena Cho: [00:24:32] Yeah. Something I've been thinking more about is, obviously we both practiced litigation, this idea of knowing joy in the work that you do on a day-to-day basis. And whether that's possible when you're a litigator, especially in the context of the litigation system; the way it exists now, or has sort of been very traditionally. I find so many lawyers, like I talk about happiness and joy because you know, why else are we on this planet? I don't mean it in a trite sense, right? I don't mean it like, I get to have a bowl of ice cream so therefore I'm happy. But more of that deeper sense of feeling like the work that you're doing is meaningful, and finding joy in that. And I'm curious, when you're doing litigation do you feel like you had a joyful life? Is there a way you can have both?

Karen Gifford: [00:25:39] I like to think that. I do see a lot that isn't consonant with that, in the way that litigation is practiced today. There's a lot of just you know, things get personal really quickly unfortunately. And kind of the level of professionalism has declined unfortunately. So that's a problem, that's hard you know. I don't want to say that you can just joy your way through that.

Jeena Cho: [00:26:19] It's not like a, fake it til you feel it kind of thing.

Karen Gifford: [00:26:21] No, and there is a real joy in expressing who you are. And sometimes who you are is a great litigator, right? Joy doesn't have to express itself with puppies and rainbows and flowers. It can also express itself in a great argument or you know, a beautifully presented witness. I've certainly had those moments where I felt that way, and interestingly I think those moments when you really do feel very deeply joyous or contented or happy with how things go in a work setting, they're not the ones where you're saying the nasty thing or scoring a cheap point. They're the ones where you feel like not only are you making your self shine, but you're making the whole system shine. Like if you think about those really big moments in your career, everyone felt uplifted.

Jeena Cho: [00:27:33] Regardless of who won or lost, yeah. And I've also had experiences where the client didn't get the outcome that he or she wanted, but felt deeply cared for throughout the case. And somehow they didn't feel more.. You know I think a lot of times when you come out of the litigation system you can feel more broken than when you went in, I think that's the majority of the case. But if you can sort of help your clients through.

Karen Gifford: [00:28:03] Oh absolutely. And I can't imagine that for you in a bankruptcy practice, that must have been a huge challenge. Because it's just such a rough time that people are going through. And you've spoken so eloquently about the really heartbreaking sides to a bankruptcy; it's not just a money thing. I think making people feel that the system at least cared about them is a huge step forward.

Jeena Cho: [00:28:41] Do you ever miss practicing law?

Karen Gifford: [00:28:46] You know, not enough to go back to it. I really loved it when I was doing it, but when I think about practicing law I have that feeling that I was saying before, like I really did with it what I wanted to do. I don't feel like oh, if only I had X, Y, or Z. But it was great, it was great when I was doing it.

Jeena Cho: [00:29:15] So for the listeners out there that are considering some sort of transition, either staying in law or out of law. Any particular advice that you might want to offer them?

Karen Gifford: [00:29:33] Well, when I was thinking about these changes and they did feel momentous to me, one thing that I told myself was I'm going to make a decision, and it's going to be obvious. The answer is going to be obvious. And I just stuck to that. And you know, there are pluses and minuses in everything you do. And looking back, I think maybe I stuck to practicing law like six months or a year longer than maybe I probably should have. On the other hand, I have the satisfaction of knowing that it was obvious by the time I made that decision, and that worked for me. And so if that's how you're feeling, you're really unsure and you're not comfortable with that, I think you can have the confidence to know that your instincts are going to take you in the right place. And that you can get to a place where you're absolutely comfortable with whatever decision you make, whether it's to stay with the practice, leave, go part-time; whatever variation makes sense for you, your own instincts are going to guide you well.

Jeena Cho: [00:30:46] I love that. So the name of this podcast is called The Resilient Lawyer. What does it mean to be a resilient lawyer to you?

Karen Gifford: [00:30:55] Oh, that's such an interesting thing to reflect on. I think the practice of law has a lot of challenges. And really, if we take the practice seriously, those challenges can really implicate our core values, implicate what kind of people we want to be, and being resilient in the face of those challenges to me means engaging with them fully, and also staying anchored in our core values and our commitment to ourselves, as well as to all that we want to accomplish.

Jeena Cho: [00:31:36] Beautiful, I love that answer. Karen thank you so much for joining me.

Karen Gifford: [00:31:42] Thank you Jeena for having me. It's just such a huge pleasure.

Jeena Cho: [00:31:48] Thank you for tuning into another episode of The Resilient Lawyer podcast. If you've enjoyed the show, please consider telling a friend. It's really the only way we have to grow the show. Also, why not leave a review on iTunes. It only takes a minute, and really does help with the visibility and promotion of the show. If you have any questions, drop me an email at Until next time.

Closing: [00:32:14] Thanks for joining us on The Resilient Lawyer podcast. If you've enjoyed the show, please tell a friend. It's really the best way to grow the show. To leave us a review on iTunes, search for The Resilient Lawyer and give us your honest feedback. It goes a long way to help with our visibility when you do that, so we really appreciate it. As always, we'd love to hear from you. E-mail us at Thanks, and look forward to seeing you next week.