Ep.79/ A Medical Diagnosis, a Law Degree & A Huge Pivot: Debbie Epstein Henry

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In today's episode, we have a special guest, Debbie Epstein-Henry. Debbie is a lawyer turned speaker, consultant, author, and communication coach with an expertise in careers, women, and workplace dynamics and the law. We dive deep into her journey from lawyer to entrepreneur, exploring the pivotal moments and strategies that led to her success. She provides valuable advice on effective self-promotion, networking, and communication techniques. Debbie emphasizes the importance of aligning self-promotion with the cause or organization (meaning how to brag the right way). Plus she talks about how to use storytelling to convey your successes and how to be a resource to others when networking.

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Do you want to learn to communicate better, including how to advocate for yourself?

Plus she talks about how to use storytelling to convey your successes and how to be a resource to others when networking.

In this episode you will learn:

Turning adversity into motivation
Monetizing your idea and turning your hobby into a viable business model
How to use storytelling as a self-advocacy technique

Quotes from our guest:

“I saw the market interest and then I was like, how do I seize on that?”
“If you want to be an effective public speaker, you have to know who you're speaking to if you haven't done your homework and if you haven't evaluated what is the problem that your audience is looking to solve, if you haven't figured that out, they're not going to like you because you're not bringing value to them.”
“tell a story. Let me learn about your life. Let me get insight into who you are and why this matters and why I should care. And then I'm going to remember you and I'm most importantly going to remember your message and how I can apply it to my own life.”
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GUEST LINKS:

Debbie Epstein Henry’s Website

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Kim (00:02):

Debbie Epstein Henry joins us to share how a medical diagnosis forced her to rethink her career, how she shifted from lawyer to entrepreneur and speaker Plus she offers tips on how to communicate better, including how to advocate for yourself.

(00:17):

Welcome to the Exit interview with Kim Rittberg. Do you work for yourself and want to supercharge your business while still having fun? Well, this is your go-to podcast part MBA Part Cheer Squad. Every week I'll be joined by top business owners who share the secrets to their success. After I found myself working during childbirth true story, I quit my executive media job to bet on myself fighting the fear and imposter syndrome to eventually earn six awards, an in-demand speaking career and features in Fast Company and Business Insider. Now I'm here to celebrate all you rock stars betting on yourself, and I want to help you win. Tune in every Wednesday to hear from remarkable founders and don't miss our Solo Friday episodes, a treasure trove of video and podcasting mini masterclasses with me. Exit the grind, enter success on your own terms. Don't forget to subscribe today and grab my free video tips at my website, kimrittberg.com.

(01:19):

In today's episode, we have a special guest, Debbie Epstein Henry. Debbie and I met through a women's networking group and we dive deep into her journey from lawyer to entrepreneur, exploring the pivotal moments and strategies that led to her success. Debbie's a lawyer turned speaker, consultant, author, and communication coach with an expertise in careers, women and workplace dynamics and the law. She'll take us through how she built a national network of 10,000 plus lawyers, which is incredible. In this episode, she provides valuable advice on effective self-promotion, networking, and communication techniques. Debbie emphasizes the importance of aligning self-promotion with the cause or organization, meaning how to brag the right way. She talks about how to use storytelling to convey your successes and how to be a resource to others when networking and I love, she basically connects networking with self-advocacy and building your business that it all works together in tandem, that they're not like isolated things that you need to think about the advocating for yourself and letting people know who you are and what you've done is just a small part of the bigger picture of giving, giving and offering value to people.

(02:20):

And that in turn we'll come back to you. I'm really excited to bring in Debbie Epstein Henry. She's a lawyer turned speaker, consultant, author and communications coach with an expert in careers, women workplace dynamics and law. She runs DEH consulting, speaking, writing, and she speaks at private events and retreats and has given nearly a thousand talks. She's been featured in New York Times, NBC Nightly News, wall Street Journal and National Public Radio, and she hosts programming with thought leaders that draws hundreds to thousand plus participants each quarter. So I met Debbie through the North Fork and I was so impressed with her and I feel like she has so much that we can all learn. So I'm going to bring Debbie in now and ask her so many questions. She has written two bestselling books and built a network, a national network of 10,000 plus lawyers. Debbie, thank you for joining us.

Debbie (03:05):

Thank you for having me. So awesome to be with you. Oh

Kim (03:08):

Wait, sorry, I forgot to mention she has a BA from Yale and a JD from Franklin Law, and so I'd love Debbie to, if you could first tell me about what made you decide to go from lawyer to working for yourself to running this network, all of that.

Debbie (03:20):

Definitely. So again, thanks so much for having me. So I was in law school actually my third year. I was a newlywed and I had this crazy health scare. I actually had a grand mal seizure and was rushed to the emergency room. Initially the diagnosis was a brain tumor and five days later I underwent brain surgery and the brain surgeon found this very rare parasite and basically I had to take some prophylactic antibiotics and I was going to be good as new. But being a third year in law school, 26 year old newlywed, it completely rocked my world. I felt super grateful that it was supposed to be a brain tumor. And then I really had that moment where I was like, I'm going to make sure that I love what I do in my life and the people I spend it with, and if I don't, I'm going to have the confidence to make change. So that really set me off on a different trajectory than where I was prior to that experience.

Kim (04:21):

And then so what was your first step? You go from lawyer, what next? How did you decide what would happen next? So

Debbie (04:27):

Fast forward, I ended up practicing law for a while and I just hated it. I, at the time, I had just had my second son and I was just like, I really don't love this at all. And all I was talking about with my girlfriends who were lawyers and other professionals was how do we play an integral role in our kids' lives and also be on an advancement track? So in 1999, I sent an email out to six lawyers, said, I'm starting this network on work-life issues. The first event will be at my firm forward, the invite to who's interested. Within a couple of days, 150 people email me back in response and work-life was barely a term of art. I'm like, there's something going on here. I'm clearly not the only one who is struggling here. And so I ran that first event. I was like, how do I make this into my career? I spent three years running what became monthly events on my monthly crisis and it just ended up morphing into this national network through visibility, et cetera. And after three years of doing it, I just had enough momentum that I left practice and never look back.

Kim (05:28):

Okay. I feel like a lot of people have these things where they're like, I have this idea, I want to gather people together, but how do you make it monetized versus it's a hobby basically.

Debbie (05:36):

Right. And let me just say it wasn't like I have some great idea. It was like I was unhappy. I reached out, I saw the market interest and then I was like, how do I seize on that? So for three years, to answer your question, I just did a pro bono. I just tried to read as much as I could. I tried to network with as many people who were interested in these issues. I just tried to really become immersed in the topic to see is this something I'm interested in? Do I like public speaking? Do I like work-life issues that sort of morphed into women's issues? Does this all interest me? And so I did not earn any money on it. The first three years I did it as a litigation associate on the side. After three years of doing it pro bono, I knew I had enough of a following and there was really nobody in the field.

(06:21):

And so I was like, there's an interest I can make this happen. And so what I did initially was I converted those monthly meetings. I was running into a membership organization and I developed a national membership organization at the time law firms around the country who basically would send their lawyers to my events as a way to gain information on what's happening on work-life trends in the legal profession. And so by having that membership organization, that was the first way that when I stopped practicing law on day one, I was profitable. But what really led to a viable business model was this membership organization was a very nominal expense for law firms to have their lawyers join and participate. But for this very nominal commitment, these law firms started not just sending their lawyers who are interested in these issues, but they're professional development types of people who are management representatives. Those people showed up and they started hiring me to speak at their retreats and their women's initiative, excuse me, women's initiative events and all that sort of stuff. And that's how it became a viable consulting model.

Kim (07:26):

And now how does it look now, obviously you're many years into it, how has that shifted?

Debbie (07:30):

So in 2024, it'll be 25 years that I've run some iteration of these events. Now they've morphed into quarterly events that are hosted still by different law firms around the country. Since the pandemic I went virtual, we have enormous participation. Sometimes we'll have over a thousand participants per quarter. I bring in different thought leaders, I interview them and we talk about life and work and everything in between. So it's still a membership organization for law firms. It's still a way that law firms see me and then hire me as well as other companies. But it's now a virtual model that people participate, they get recordings of. And I bring in different New York Times bestselling authors and thought leaders to interview on different topics of interest.

Kim (08:15):

And what advice would you give for someone who wants to do their own thing and wants to grow a business similar to how you did it?

Debbie (08:21):

What I would say is, first of all, pilot, what I shared about my story is that for three years I was working as a litigation associate and I was doing this gaining information, reading, networking for three years on the side until I knew number one, there was a market need. And number two, I was somebody who could fill it. And if you don't have answers to those questions, you don't want to quit your day job unless you're positioned to do that. I was not. And so piloting is really important. You're not just assessing whether you are strong in those areas, you're considering whether you're interested in those areas, but also is there a market need? And again, are you the one to fill it? So that would be the first thing I would say is really focus on that. And after that, I mean part of what you want to do is hedge your risks. You want to assess what is the risk. I've taken a lot of significant risks in my professional life, and again, part of what gave me the confidence was that crazy health scare, but I'm not reckless about it. I look and I see, can I straddle my old job at a time where I can assess is there really interest? Am I the one to fill it? And then I do it from there.

Kim (09:34):

Yeah, I hear from so many other entrepreneurs is making sure there's market fit, making sure you're providing something that people want. I think we talk so much about passion and passion is great, but if you're passionate about something that there really isn't an audience for and there's really not a market fit, then maybe follow a different passion. I think that's a helpful assessment. And then you now are a communication coach, so how does that play into all of it?

Debbie (09:56):

Sure, and that's something that's evolved later. So I mentioned, I've been speaking for nearly 25 years, I've given almost a thousand talks in my career. And about five years ago, people started seeking me out and saying, you've done this. I'm terrified of public speaking, or I don't know how to run a meeting, or I can't build a team and inspire people or I dunno how to present to business leaders. And so through that, I just started doing this communication coaching. And now interestingly, I'm doing at companies and firms, sometimes in groups, sometimes one-on-one, but then also I'm getting asked to, if somebody just reached out to me over the summer and was like, I'm officiating a wedding and I am going to be in front of hundreds of people and I'm not confident. So I work with them throughout the summer to edit their remarks and have them do practice sessions and all these sorts of things. Public speaking is the number one fear that people have and it impacts 75% of the population. So for some people it's actually getting on stage and that's something they're really fearful about. But for others it's just about communicating with confidence and that is incredibly important for how you relate in the business world, how you relate personally and everything in between.

Kim (11:04):

What are the biggest things that you see people getting stuck on when they're struggling with speaking?

Debbie (11:09):

I think the biggest mistake that people make is that they don't know their audience. So if you want to be an effective public speaker, you have to know who you're speaking to if you haven't done your homework and if you haven't evaluated what is the problem that your audience is looking to solve, if you haven't figured that out, they're not going to like you because you're not bringing value to them. So if you've done your homework, you know who your audience is, that's critical to effective public speaking. The other thing I find is really a big mistake that people make with public speaking and communicating is they hide behind the data. They are focused on either charts and graphs and data solely that or they're really focused on corporate speak, which is just these ridiculous words that mean nothing and people's eyes are glazing over.

(11:59):

Instead make it personal, and this is something that a lot of people are still fearful of in the business world, but tell a story. Let me learn about your life. Let me get insight into who you are and why this matters and why I should care. And then I'm going to remember you and I'm most importantly going to remember your message and how I can apply it to my own life. So if you can get personal, get to know your audience and really then tailor your messaging and see how you can be helpful. The other thing is I find so many people are very me focused. And if you can instead flip it and see how can I be a resource? How can I help? Again, what is the problem this person needs you to solve and are you the one to solve it? If so, convey that in your messaging. Don't make it about you. Make it about them.

Kim (12:46):

Yeah, I love that. It's funny, what we were talking about market fit earlier is in the same way that what you're passionate about has to align with what people need. When you get up on a stage, only speak about something that you're passionate about, but make sure it's at the right place with the right audience. And it's funny, coming from being a journalist or former journalist, whatever, I always say to people going on TV or doing any sort of interview, ask the producer what they're going to ask you about, be prepared. And I think that's the idea of sometimes people are, I don't know, worried or reticent or shy to ask for more information. But when I speak now, I've started asking who's going to be in the audience? Can you give me the breakdown? What's the breakdown of entrepreneurs versus corporate folks? Because it is different and it does change, and I want to bring the most value I can. I'll have fun no matter what, but I want them to feel that they really walked away with such value. And so I think I really like that point of understanding your audience. And by the way, the corporate jargon I have, and I'll ask you later, I would love to know what is the corporate jargon you hate the most? I have such strong feelings about this.

Debbie (13:49):

I mean, this is not even corporate jargon, but when people are giving the talk and they talk about folks like F-O-L-K-S, I'm like, who uses that term? And do you ever say like, Hey folks. I mean, it's just people get, I don't know. They go into this other scripted mindset and it's so inaccessible and it just makes no sense to me. I don't get it at all. But really I think when you're thinking about communicating, you're thinking about really doing your homework, like I said, and figuring out what people want. And if you can figure out what people want, you're going to bring value to them.

Kim (14:26):

Awesome. Now switching gears, I would love to know, so one of the things I advocate for, and I have read that you agree with some of what I think is that a lot of us don't brag, especially women to be honest, but a lot of us aren't really showcasing our competence well. So talk to me a little bit about what's some advice you have to give about how someone can show up showcasing what they're great at without coming off as obnoxious?

Debbie (14:50):

And it's a fine line and the research shows that women are punished much more when they are on that tight rope. So one of my favorite recommendations is about aligning your own self-promotion with your organization you're working with or your business or some value or purpose that's beyond you. So let me give you an example. So, and let's say you do some nonprofit work and for this nonprofit, let's say it's an arts organization, you do a video for them. And so that is, let's say it's promoting let animal rights, let's say you are using your skill and your expertise in something that is volunteer. So for you be able to showcase your video showing animal rights, let's show, let's say, and then use that as a way to promote the work of this amazing nonprofit. But you also are putting yourself in that context because of course the video is yours.

(15:50):

And so the more you can align your own self-promotion with ideally a great cause, but for those people who are listening who are still employed with an organization to align it with their employer. So let's say I won some 40 under 40 award and I am working at an accounting firm, rather than go into the marketing department in my accounting firm and saying like, Hey, aren't I fabulous? Can you share this with our clients? Say some of our clients really seem to emphasize the importance of outside recognition and stuff. Can we use this new award that I got as a way to really show our clients that we're working outside of our company, not just inside of it? So it's a way to really tailor this exposure that in this case I just got, let's say, with something that is a client opportunity. Whenever you can do that, that's really powerful.

(16:41):

My second favorite tip around self-promotion is if you're comfortable storytelling, it can be a really effective way to be able to self-promote. So let me give you an example of that. I did an event many years ago, it was actually my first book tour and I was at a firm and the day after the event, the client who had brought me in, she said, we're getting all these accolades from our clients. They love the event. They thought it was amazing. I don't want to forward these accolades to the head of my firm because it'd be like, oh, it's so obnoxious. I said, well, give me a better sense of some of what's coming in from these clients. And she said, well, one of the clients, we've been trying to do their corporate work for many years, we just do their environmental work, but their real big ticket items are their corporate work.

(17:33):

I said, well, why don't you forward these accolades to the managing partner and then say, looks like Jim was really enthused about last night's event. Maybe now is the time to pitch him on the bigger relationship. And so that's just what happened and that's what occurred. Now, that example I just provided is again, that client of mine using her own success as a way to promote the firm by getting more client work. But in telling that story that I just told, I used my second technique, which is I did storytelling. So as I told you that story, I snuck in there that it was my first book tour. So now I have two book tours. I also said there were tremendous accolades about the event. I was the speaker. I indicated I came in for that event. Hopefully you were engaged in the learning of that story that you weren't like, oh, why is Debbie so self-aggrandizing that she has to stick in?

(18:24):

That sort of thing. The idea is you are noting those details that I just provided. It's fine if you noted them, but you're not distracted or feeling put off by it because you're so engrossed ideally in the story. So those are my top two favorite tips around self-advocacy. And some people like that term better than self-promotion. Self-promotion feels like more negative, but one is align your own self-promotion with a cause or an organization you're affiliated with. And number two story tell, put these details in that show your gravitas or some success you've had, but still use that story as a teaching so that people hopefully won't be put off by it.

Kim (19:04):

That's super helpful, thank you. What do you recommend for a self-employed person or a business owner meeting a person for the first time in a networking event? I feel like so many times people are like, I'm a coach or I'm a lawyer. That's fine. That's technically what you do, but it does not help you stand out. What would you recommend in a networking situation where you're introducing yourself?

Debbie (19:24):

My most important recommendation here is based on a piece I wrote number yours ago is called make your ask a give. So you're in a networking situation and you do want to distinguish yourself and you're introducing yourself and hopefully you have a bit of an elevator pitch, and so you're able to say who you are, what you do, but the other piece of what you want to do besides ask that other person who they are, and what they do is you learn what that other person does and who they are, and then you think, how can I be a resource? So for example, we're having this conversation, you're interested in self-promotion techniques. Right after this call, I can shoot you an email, which by the way, I've done before when we originally met, you indicated an interest in this topic, and I sent you an article I wrote on this about striking the self-promotion balance.

(20:16):

Now, that was a resource you needed, but it was also a way for you to learn more about my work and ultimately you invited me to be your guest, which was super generous of you, but that's part of showing yourself as a resource. So when you're in a networking venue, rather than just focus on getting people to know who you are and what you do, you also want to again hear that information from them and say, how can I be a resource? What does this person need and am the person who could fill that need? And by the way, if I'm not, maybe I'm going to connect them to somebody else who does. I actually, another member of web, how we originally met the women's entrepreneurial business, we met through a mutual friend Emily Warren, and she said, oh, Kim's doing amazing work. You two may enjoy meeting each other. So in this case, Emily was the connector. So even if you can't provide that need, it's such an act of generosity to put two people together who may be able to help each other.

Kim (21:17):

I love that. What about just straight up, I struggle with this to be honest, because I have won awards and I'm like, I'm going to mention that I won awards. And sometimes I struggle with, I don't know a non obnoxious way to say it, but sometimes I just do it with a laugh. It depends. Now they're literally in my background. So I'll be like, and I won awards and I'll do a Vanna White thing, but I'm showing it because I'm making light of it. I'm acknowledging that it's a little awkward to say this, but also it's true and how can I help you do it? So I try to use the techniques you were saying when I say I was so proud to have partnered with this nonprofit. The project went really well and we were awarded with these trophies. So I would love your opinion on if you have some really good accolades, how to say them.

Debbie (22:01):

So again, coming back to knowing your audience, so you asked me before very generously about my work as communication coach. The way that I have legitimacy as a communication coach is because I've given nearly a thousand talks over the last 25 years. It's not an award, but it is a data point that informs why somebody may be able to benefit, ideally from my communication coaching. So what I've done there is I've used that as a data point to be able to answer in your case, your question, but if somebody said to you, look, there's a lot of people in video these days. I mean, why should I consider you and not somebody else? Again, you could use it just the way I use those nearly a thousand talks. You could say, there are a lot of people out here, but some are good and some are not so good.

(22:54):

And even I've gotten recognition and awards for the quality of my production, and having done it originally as a journalist and then done it on my own, I've been able to get that recognition and distinction, which hopefully will convince you why I'm better to be hired as a video in the video space than somebody else. What you've done there is you're basically using it as an explanation. It's similar to, I have a real pet peeve about resumes. Sometimes you'll see resumes with these self-proclaimed qualities that they have. We'll say team leader, great communicator and all this ridiculous stuff as if your resume is some objective piece of paper. I'd rather not see any of those self-proclaimed qualities that are really self-promotional and have no basis. In fact, instead to show in the first bullet in your job description, led a team of 30 people in the successful acquisition of this company. I'm like, that's a great leader. That's a great communicator to have achieved that for X amount of money to me. So if you can get factual, it takes it away from it being obnoxious, and it's like, let me explain how it can help.

Kim (24:06):

I love that. I also advise people that I think sometimes people think that things are bragging when I'm like, you're actually just stating a fact. I think it was you and I or someone else. We met with someone and they were a food stylist and they had mentioned that they worked on Bobby Fla or something else. To me, that's not a brag. I work in media. She's telling me I am not an intern. I'm a very experienced producer, and this is a show I worked on. I did not see it as bragging. I saw it as a data point, and I think a lot of times people get hung up on the concept of accolade, and I train people on how to be thought leaders through content, and one of the things I say to them is, an accolade can be anything. How many people read your recent blog post?

(24:45):

It can be the school you went to. It could be any academic institution that you're related to. It can be clients you helped, it could be clients. You've helped them earn more money, get more confident. It can be anything all the way up to winning the top award in your field. I think of accolades, it doesn't have to be so huge, but it's a part of what separates you. But I agree with your point of we sometimes make it this big braggy narcissistic thing, and it doesn't have to be. Sometimes it's just, oh, this is the thing I'm doing. I used to have a jewelry company in my twenties and people would say, oh, you make jewelry. That's so nice. So does my grandma. I'd be like, oh, yeah, great. I have a trunk show at Bloomingdale's this coming weekend. And they're like, what? That's not a brag. That's a statement, a fact. You will then take away, wow, your jewelry must be good. That's not for me to be like, my jewelry is so amazing. That's just to say, Hey, this is the level I'm at.

Debbie (25:34):

Right? Coming back to make your ask a give, it's explanatory, but it's also that's a give. Let's say the holidays are approaching. I've got to knock out some shopping, and then I'm like, oh, you're going to be at Bloomingdale's. Let me just bang out all those gifts I have to get. So it's again, if you see yourself as bringing value, if you see yourself as a resource, it's really just being descriptive and coming back to our friend who's a chef, Sarah. I mean, in her case, it's not just that she wasn't bragging, she was, again, it was a fact, but also part of what we do when we communicate effectively is we shortcut. So we could quickly be like, okay, she's working with Bobby Flay, okay, and she was in the New York City restaurant scene and she worked here. You can just be like, okay, this is what a food producer looks like, who is in these spaces? And it's a shortcut. So sometimes referencing those kinds of things or an award or something, it's like, okay, she's in this category and it helps us shortcut in our brain. Okay, next time I need somebody on video. I'm going to reach out to Kim because I know she's got X, Y, and Z.

Kim (26:40):

Amazing. Debbie, you're such a wealth of knowledge. How can our listeners connect with you, find out more about you?

Debbie (26:45):

First of all, thank you so much. It's great, and I will be having you on my podcast, so I'm looking forward to learning more from you. I'd love for people to check out my site, debbieepsteinhenry.com, and if anyone needs a speaker at a retreat or needs a communication coach, they should reach out. So thank you so much. This has been wonderful.

Kim (27:02):

Thank you. And you can connect with debbie at debbieepsteinhenry.com.

(27:10):

Thank you for joining us. Don't forget to exit the grind and enter success on your own terms. This is the exit interview with Kim Rittberg. Don't forget to grab my free download, how to Grow Your Business with Amazing video at kimrittberg.com and linked out in the show notes. I love to hear your feedback. Make sure to submit to me what you learned from the show and how you are crushing it on your own terms. Connect with me on Instagram or LinkedIn at Kim Rittberg, R-I-T-T-B-E-R-G. And this show is edited by Jillian Grover and produced by Henry Street Media. I'm your host and executive producer, Kim Rittberg.

Kim RittbergDecember 13, 2023Comment