Ep #59: Design Your Career with Style with Estelle Winsett

The Joyful Practice for Women Lawyers | Design Your Career with Style with Estelle Winsett

I’m always looking for new ways to help you style a career that works for you. So, whether that means going down a different path as a lawyer, starting a private practice, or moving out of law altogether, my guest on today’s show has some valuable and unique insights to share about this process of developing a career that works for you.


My guest this week is Estelle Winsett, a lawyer turned Director of Professional Development, but she also happens to wear multiple other hats, figuratively and literally. She is a style coach, a mother, she comes from a family of lawyers, and she’s curated her own career with intention, creativity, and courage, and we’re talking about all of those things.


Tune in this week to discover how to be intentional about your career, and how to thrive professionally. We’re discussing the parallels between curating your style and pursuing a career you truly love, how to distinguish what you have to offer, and decide how you want to show up.



If you enjoyed today’s show and don’t want to miss an episode, be sure to subscribe and follow the show. And if you haven’t already, please leave a rating and review! Your feedback will help me create a podcast that’s tailored to your needs and goes straight to the heart of what matters to you. Click here to learn how to subscribe, rate, and review.


What You’ll Learn from this Episode:
  • How Estelle’s career in law developed as she decided she wanted to start a family.
  • The unique perspective and skillset Estelle has gained from her work in professional development.
  • Estelle’s unusual approach to finding and applying for her current role.
  • What properly preparing and proactively planning your career looks like.
  • Some questions early-stage lawyers should be asking themselves in order to thrive professionally.
  • Estelle’s advice for having intentionality around your style, and the parallels between being intentional in your style and your career.
  • Why feeling good in your clothes allows you to show up to interviews and pitch meetings with a higher level of focus and confidence.
  • How to embrace the trial and error required for styling your career the way you want it to be and distinguishing yourself.


Listen to the Full Episode:

Featured on the Show:
Full Episode Transcript:

You’re listening to The Joyful Practice for Women Lawyers Podcast episode number 59.

Welcome to The Joyful Practice for Women Lawyers Podcast. I’m your host Paula Price, lawyer turned certified executive coach. This podcast was created to empower women lawyers just like you to create a life and practice you love. Join me every week for a break from the hustle so we can focus on you, what you truly want, and how you can create it.

If you’re over the overwhelm, done with putting out fires, and ready to create a life and practice that brings you more joy, you’re in the right place. Ready for today’s episode? Let’s dive in.

Paula: Hi everybody. Welcome back to the podcast. I am so, so excited to be welcoming you all this week, and especially to be welcoming our very special guest. Her name is Estelle Winsett. She is a lawyer turned Director of Professional Development. She also happens to wear multiple other hats. She is a style coach. She is a mother of three boys. She comes from a family of lawyers.

What I think you will all find particularly interesting, not that those are not already interesting, but you’ll find particularly interesting about Estelle is that she has curated her career with intention, creativity, and courage. Today we are going to talk about all of those things, how to style your career. So Estelle, welcome to the podcast.

Estelle: Thank you. I’m so excited to be here.

Paula: Estelle, it is so nice to have this chance to speak with you. I was wondering if you could tell our guests today a little bit about yourself, including the work that you do now.

Estelle: Sure. So I started off as a practicing attorney. I come from a family of lawyers. So my dad was a very strong influence on me at a young age. I always just knew I wanted to be an attorney. So I kind of did the traditional path. I went straight from undergrad to law school and started practicing here in Memphis. I really enjoyed it. Practiced for about seven years doing employment law defense litigation.

Then I got married and knew I wanted to start a family. The one thing that was different from my experience, and my dad’s experience, is that I had a hard time separating work from home. I kind of got a little tired of some of the antagonistic nature of a lot of the matters I was working on. I just didn’t know if I wanted to start a family in that kind of headspace. I felt like I really couldn’t be home and not thinking about a case or a strategy.

So I started looking at options of ways I could use my law degree. I kind of stumbled into my first non-legal career, which was as a legal recruiter. So it was kind of a funny story. I went to talk to a contract company to see about maybe being a contract attorney.

The guy who was interviewing me ended up asking me if I would consider working for him for the company, which was never my original intention. But it was really cool as a way to keep my law degree active and then also work a part time schedule because that’s what I wanted to do. When I went to interview with him, I was pregnant with my first job.

So I ended up starting work for him when my child was three months old. I was working part time, and it was super fun. I interviewed lawyers and paralegals, and I placed them with law firms and in-house legal departments.

So I got into this career development space where I was looking at resumes all day long and trying to play matchmaker. So I started seeing ways that people could promote themselves better through the resume that maybe they weren’t adequately conveying what they did, and their cover letters weren’t necessarily persuasive. So I kind of started helping people with their resumes and cover letters.

I worked there for about six years. I ultimately transitioned from part time to full time. I heard about a position at the law school, my alma mater, because they had an opening for their director, or rather of their dean of career services. Several people reached out to me and said, “I really think you would be a good fit for this.”

So I started researching it. I started reaching out to people who held that position at other universities and law schools and started to kind of get my head around it and decided yeah, I really do want to do this. So I ended up taking kind of charge of it.

I set a meeting with the current dean of the law school, and I didn’t tell him why. I just set up an appointment. He’d been my professor. I’m trying to think what he taught. I think it was business law, but any event he was super nice. So I just kind of showed up and was like so I hear there’s this position, and I think I would be a good fit for it, and I wanted to talk to you about it.

So he ended up walking me down the hallway showing me where the office was. At that point, I don’t think that application has had closed yet. So I’d already submitted my application. Then it just kind of went from there. I was able to meet with him and the others that were on the recruiting committee.

Anyway, so I got that role. What really appealed to me about that role was that it was a reinvention. My predecessor had been there for 15 years, and the office actually had been vacant, I think, for about 10 months. So I was able to start from the ground up and create a really strong career services office in the way that I felt was the best way. I wasn’t hemmed in by things that having to be done a certain way. So that was super fun. I did that for about three years.

About that time, we had a new dean that started at the law school. It just wasn’t as good of a fit for me anymore. So I started looking at other options. That’s when I decided I wanted to take the part of career services that I loved, and parlay it into a law firm position. So I started researching all the options out there and figured out that what I really wanted to do was professional development at a law firm.

So I kind of my feelers out, and then a position became available where I am now for their first Director of Professional Development. It was perfect. I was very excited. So I did a lot of research again and just put my best foot forward about how my skills were transferable because I had talked to other people in that same role and other firms. Just positioned yourself to start this new role at the firm. I’ve been here now for about seven years. So that’s kind of a long winded way of explaining my career path.

Paula: Beautiful. No, I’m so glad you explained it like Estelle. It wasn’t long winded at all. I think it was quite concise relative to all that you’ve done. A few things that I would love to highlight about the path you’ve taken is number one, I think in that contract role, you had that position of the recruiter. I think that’s such a neat perspective to have.

Because, like you said, you’re seeing the CVs come in. You’re seeing the cover letters. You’re seeing how different candidates distinguish themselves and how they can distinguish themselves better, which I think is a very unique perception to have. Because not everybody sees that same amount of volume, right? Each of us is writing our own materials. We don’t necessarily have the benefit of comparing them to other people’s materials and doing that analysis. So I think that’s a really neat skill set that you have.

Then to bring that to the role in the law school. I didn’t know that you kind of sought out the dean and had a chat beforehand about the position because I think you’re so great at this. I think you really have a knack for looking at something and deciding okay, what is a really great approach for me to do this? Like how can I learn more about the position? How can I figure out whether this is the right position for me? So I just love that.

Then you talked about the transition into the position that you’re in now. There’s a story, I’ve heard it before, and I’m gonna ask you to share it with our guests because it’s so good, about how you approached your interview for your current role. Please be sure Estelle.

Estelle: Sure. So as I was looking into finding a role in a law firm setting that would be best suited for me, I talked to a lot of colleagues that had been presenters at some of the conferences I had attended. So the thing about career services for the law firm and law school setting is there’s an overriding organization called NALP. There are conferences every year that speak to both the PD role in the law firm setting in the PD role in the law school setting.

So I had attended a lot of presentations that have been from law firm PD professionals. As I always would tell the law students, I reached out to them because anyone who takes the time to do a presentation cares about the topic. When you follow up and tell them how much you enjoyed that conversation, you’re creating a relationship. So I then parlayed that further into having informational interviews to find out a little more about what they did.

So I surveyed a bunch of different people who did both recruiting and professional development at law firms. I looked at LinkedIn job descriptions of people who were at law firms. What I always would tell the law students to do is if you’re interested in a position, go look and see what job descriptions you can find. Because that’s going to tell you what skills are most important for that role.

So, after doing all that research, I landed on wanting to do PD at a law firm. I know I wanted to stay in Memphis because I have three boys, and my husband here and my in-laws and my family live in Memphis. So at that point, the boys were young, and I didn’t want to look somewhere beyond Memphis.

There wasn’t many opportunities for PD in law firms in Memphis. It was a relatively newer area that was taken off more in bigger cities, more northern cities than in the south, but I also kind of have my feelers out. Like this is kind of what I’m looking for. So someone let me know that there was a new position that this firm. It appealed to me because it was the first time they’ve ever had a director in this role. It was a whole new department.

So what I did is I went back to all my notes that I had made for my informational interviews. I’d asked what are transferable skills from a dean of career services to a director for PD. So I had an ability to craft a resume that was really pointed and relevant to this role.

It’s kind of a funny story because by the time I went to apply for the position, they had taken it down. So the job posting was not online very long because they got flooded with resumes from attorneys who were like that sounds good. I can do that. But they weren’t targeted resumes. They weren’t thoughtful. They were just overwhelmed. They’re like okay. I’m shutting this down.

So I had to go about finding someone in the law firm to pass my resume on to because I could no longer post. So I found a friend of my sisters who practiced in the Mississippi office, sent her my resume, and she got it to HR. So that’s how I got my first interview at this company. So I distinguished myself that just having a very targeted, thoughtful resume.

Then when I went into the interview, I’d also talked to other people who did PD at the law firm to say okay well if you were starting a new position, what would be some of the first things you would do? Like in your first three months, what’s the most important thing to do? In doing those calls, I realized that you really needed to do a needs assessment and determine, from the leaders in the firm, what’s the most first priority to work on for someone who’s a new director of professional development?

So I just laid out a business plan for what I anticipated and what I would do as the new director in this role for the first three months. During the interview, I at one point just pulled it out of my briefcase. If I were to have this role, this is what I would do in the first three months, and this is why. So I think they weren’t expecting that.

These are little things that I tried to teach the law students when I was at the law school, and what I try to teach attorneys at the firm is you got to be proactive about your career and distinguish yourself because no one’s going to care about your career as much as you do. So I distinguished myself from the other applicants because a lot of people have just said well, why not? I’ll apply for this role. That sounds good, but they hadn’t done the research. That’s what I did.

Paula: Estelle, I love every step of that story. Thank you so much for sharing it because you have literally shown how to step by step right from the very beginning, attending the NALP conferences, listening to the speakers, following up the speakers to tell them that you enjoyed what they talked about.

I mean this is something that I encourage everyone to do, especially now with Zoom you can watch all these seminars. There are people speaking. These are opportunities to meet and connect with people where what they’re talking about resonates with you. As you pointed out, probably resonates with them as well because they’re talking about it.

So I just love how, and then you have your notes for your informational interviews. Then you distinguished your CV, your cover letter, and then you showed up the business plan. I just love it. Pulling it out of the briefcase, here’s your first three months. I just think this is such a compelling story. Because there’s so many lawyers out there who are thinking about making transitions, who are going through the process, who are wondering why am I sending my CV and not getting anybody responding to it?

It’s like because when you approach it with that level, like you said, that intentionality right? Distinguishing yourself and showing how this is such a great opportunity for both of you. Right? That’s when the magic happens. So I just love that. Thank you so much.

Estelle: Of course.

Paula: It’s so wonderful. I know everyone listening is like oh, that was so valuable.

Estelle: Oh, good.

Paula: I love it. Estelle, so you are working with, I gather, students and associates and helping them all with their professional development. You’ve worked with students in a law firm context helping them figure out how to navigate those early stages of interviews and finding the right firm. So what I would love to ask you is what questions do you think early stage lawyers should be asking themselves in order to thrive professionally?

Estelle: Oh gosh. Such a great question. So I think early stage lawyers should be asking what are the skills I need to have as a junior associate? Really drilling down into what that means and talking to partners. Finding out what it is that they’re looking for the associates to provide them. What are their pain points, and how can they satisfy them in a way that’s very intentional?

I think as that associate rises within the ranks, those expectations change. So it’s important as a mid-level associate to find out okay, what are the expectations of me now? How can I meet them? If some of those expectations are substantive skills or having certain miles terms that they’ve done within their practice. If they haven’t done that, they need to go out and get that. That can mean several things.

If say that one of the skills for litigators, you need to have taken a deposition by your third year in practice. If you haven’t done that, find people that will allow you to shadow them as they take depositions, even if you can’t build for it.

Then be a resource for that attorney, after the deposition. Before find out okay, how did they come up with the questions? Afterwards tell them your thoughts, what you notice, what you thought was helpful. Because when you’re giving a deposition, it’s hard to both ask the questions and receive the information and process it. So make yourself an asset to that attorney, learn the skill that you’re trying to learn, and just be really proactive about it. That’s just one example that comes to mind.

Paula: It’s an excellent example. Thank you. So you think it’s really being intentional, asking for input from the lawyers in your department, whatever department you’re in. What are the expectations? Because sometimes it’ll be written down. Sometimes there’s a whole flowchart of here’s where you should be, but not always. Sometimes it’s more organic than that.

So just making sure that you’re tapped into your relationships, that you’re asking those types of questions so that they can give you that feedback. Because like you said initially, Estelle, I think you’re right. I think each of us is most concerned with our own careers relative to—I mean others will care about you, but they will not necessarily do that extra level of work that it’s sort of incumbent on each of us to do. So I love that being proactive.

You mentioned earlier in terms of career planning, again, it’s that idea of being very intentional about it. What else do you recommend in terms of an approach for proactively planning your career? You might look at your own example in terms of okay, looking at the different stages. When one thing didn’t fit, it was time to move on to something else. So what would you recommend to others, to lawyers who are thinking about their own career planning?

Estelle: You know I think being able to tap into are you happy is a really good question to ask.

Paula: It’s such a great question. Yes.

Estelle: I know that sounds kind of elementary, but it’s so easy to get in a pattern of just okay, here’s an assignment. Something is given to you, and you do the task. Then there’s a new assignment and you do the task. It’s very easy to look out five years later and think I don’t even like this task. You’ve been doing it because it’s what you do, and you haven’t—That’s, again, kind of working in a career by default instead of by intentionality.

So when you have those moments or those red flags of you know, I know I started doing this kind of practice, but I’m not really sure it’s giving me the same satisfaction or the satisfaction that I hoped it would. if that’s the case, then you need to pivot. Because if you don’t, if you don’t take charge of it then you could be stuck in a career.

Then you get to a point where it’s really hard to switch gears. If you’ve been practicing in one area for 20 years, it’s kind of hard to reinvent yourself in a different area. It can be done, but it’s harder. So having maybe these checkpoints along the way to see am I happy? If not, how can I either improve the situation or change it.

So there’s just some things that have been kind of guiding principles for me. I haven’t always been as intentional, but later on in life I started doing that. It’s made a big difference in my personal satisfaction in learning and growing in my profession and helping other people.

Paula: I think it’s such an important point to highlight, Estelle, and so thank you. I think just checking in with yourself and asking are you happy? I don’t know that that’s the first question that people typically ask themselves. Yet, if they did then what is the answer? What does that lead to? So I think that’s fabulous insight.

As I look at you, I’m thinking you seem very happy. I think what you’ve also done, and we’re gonna start talking about this too now, is I mentioned in the introduction that you are a style coach. So you wear all these different hats. One of them is some personal professional style. I’ve followed some of what you have on your website. I’ve joined your Facebook group, which I will talk about.

One of the things that I heard you say is that when you go out to shop, for example, you don’t go out shopping without a list, right. That you need to have your list. You need to know in advance what it is you’re going to buy. Not doing that is kind of like going into the grocery store where you’re hungry without a list. We all know where that ends up.

So, to me, there’s this real intentionality that you have in your approach to style. I see this intentionality in your approach to career planning. So I’m wondering if you might be able to talk about some of the parallels that you see between being intentional in your career and being intentional in your style.

Estelle: Sure. So like what you wear, how you show up in a law firm or in your job says a lot about you before you really ever open your mouth. So as I was mentioning earlier, I think it’s really easy in our style or in our career to just go about by default. There’s not necessarily anything wrong with that except for you can lose sight of your bigger goals.

The parallels that I see when it comes to style is how you present yourself matters. A lot of people think that well, I should be appreciated for my intellect. I’m a lawyer. I’ve worked really hard to be here. While that is true, there is a part of you that that’s important for you to convey your intelligence or your mastery of the skill set. You’re also giving an impression though, and you’re giving an impression to someone before you ever open your mouth. You can’t opt out of it.

Paula: This is true. Not even on Zoom. So I think it’s one of those things where if you’re like okay, so it actually does matter how I show up. The good news about it is you can craft the message. It’s totally within your control to figure out the message you want to send, and then to find clothes that support that and to find a style that is representative of the message you want to send. If that’s not something that comes to you naturally, or if you don’t have the time to do the research, then hire someone. Outsource it because it’s important.

So when I’m shopping, or working with someone, I want to find out first what are their style preferences? I help them go through some exercises to tap into that. Because instead of just going shopping immediately, you’ve done that before likely. You’ve kind of bought things. Well, this is on sale. Why not? Or oh, someone gave me this, and it may not had been as intentional.

But when you’re crafting your message, you want to start with where am I headed? What do I want to send? Then you reverse engineer it, and you find the clothes that support it. Then you create the outfits. So that’s my approach.

So as part of that, once we identify where you’re headed, the style you want to have and the message you want to send, well then you have to get the closet and say okay, what do I have that supports that? You need to have a foundation. Because if you don’t, you can’t mix and match and make tons of different outfits. You’re gonna end up just wearing the same thing every day.

So then I help them shop for those pieces. We have a shopping list. Then we create outfits. So, yeah, it’s kind of a methodical process with the end goal being this is where I’m headed. That’s going to be my guideposts to getting there.

Paula: I love that so much. As I’m listening to you, Estelle, I actually can’t wait to hear the recording of this because I think there’s so much parallel. What came to mind me is you’re asking your client to define for themselves what that style is for them and what fits with that style. What do they want to wear? What do they want to do? What are they choosing on purpose?

To me, there’s such a parallel to that, taking your own story, right? Where you talked about this very intentional career planning where you saw the jobs and you went, and you researched the positions. You were very attracted to this idea of places where you could go in and reinvent. Start from the ground up and design and create.

So, to me, there’s this real creative process that comes along in the way that you’re approaching style, the way that you’re inviting your clients to approach style, and in the way that you’ve approached your own career and how you’re, I think, recommending that we all approach our careers, right? How do we want to design them on purpose? So I just love that analogy.

If I think about, for example, if you’re a lawyer and you’re looking at job postings on a board, or you’re at a law firm and you’re looking at all the different lawyers around you and how they practice law. It’s being intentional for yourself about thinking about your career, the jobs that you want. Yes, these are other examples of what’s available or what’s been done in the world.

But what if you were to start that process from the ground up and think about okay, if I started from scratch, what would my perfect job look like? Okay, here’s a bunch of lawyers around me. They have these different practice styles. What practice style resonates with me? So I just think that the way that you approach, the way that your mind works, is gold. I’m loving talking to you.

Estelle: Oh, thank you.

Paula: I think this is an approach we can all take. When we are more intentional, I think the answer to the question that you posed, are you happy where you are? That question will start getting answered more and more in positive yes, right? Because you’re being intentional about it. To draw another parallel.

If I look at you and the work that you’re doing currently, you are wearing multiple hats. So you’ve styled not only the role that you’re in within your law firm, but also you’ve styled this role that you have outside of your law firm where you’re developing this community of professional, powerful women who are all getting together and talking about style and figuring out for themselves what that looks like. You’re working with them one to one, and I just love that you’ve done that for yourself so that you seem very happy love. Nobody else can really see us talking, but we’re both smiling. This is so fun.

Estelle: It is fun.

Paula: Estelle, you see him very happy. I think that’s not an accident. I think that comes from designing what you want to do through your professional work on purpose, and then doing that in alignment with how you’ve defined it. So.

Estelle: Thank you.

Paula: Yeah, I just think that is amazing.

Estelle: Can I say one more thing? It just came to me when you were talking. I think another thing to think about is like the career, like the style, it sometimes takes a lot of trial and error. You may not nail it the first time. That’s okay. I always like to say fail forward.

But one thing that came to mind when you’re talking about the law school settings, is if you’re trying to figure out okay what area of law do I think I want to go into? You may think you want to go into an area and then when you actually try it, you may decide you don’t like it. So I always encourage law students to try to obtain those internships in the areas that they’re most interested in. Because it’s much better to find out as a law student that actually I don’t like this than five years later and in the practice of that area. So be open to the trial and error aspect.

Paula: I love that. It hinges on another question that I have for you, which is when you try that out, right? Like maybe it’s style, and you’re trying on something that is bold. It’s different. It’s not what people are used to seeing you in. You know you’re going to have comments or reactions. Or you’re starting out and you’re trying different types of work. Whether it’s beginning stages, and you’re trying to decide between solicitor or litigator, or you’re further into your career, and you’re getting more nuanced.

How do you know? Like because there’s sometimes that initial imposter syndrome, right? Most lawyers who make that transition from student at a law school to law firm, I think so many experience that initial impostor syndrome. Then eventually we kind of build on that and get over it. But how do you know whether you’re weathering? How do you deal with that imposter syndrome? Whether it’s weathering through it and realizing this actually does fit with me, or this really isn’t a good fit for me, and it’s time for me to recalibrate?

Estelle: Oh my gosh. That’s such a good question. I think the way I would answer that is to go into it, whether it’s trying on new clothes or new style or trying out a new practice area. To go into it with a growth mindset. Because you may originally think eh, not really sure about this, but don’t dismiss it  so easily. Try it out, give it a good faith to try. Then if you’re just like you know what? I’ve tried to embrace this. The more I’ve done it, the more I realize it’s not for me.

Just like trying on clothes and saying well, so many times. I love this. I love recommending something to a client, and they say I’d never in a million years would have thought to try this on. Or I’m really not so sure about this. I just say well humor me and try it on. Because you think in your mind that you want something, but until you actually try on the clothes or you actually do the task, you may not realize that–I feel like there’s this kind of internal compass that tells you yes, this feels like me, or no, it doesn’t. But it may not always happen until you’ve tried it a couple times.

Paula: Yeah. I love that you drew the link with a growth mindset. For listeners of the podcast, I talk about growth mindset from time to time. So it may not be a new concept. But if you’re not familiar with that concept, what it really means is kind of like Estelle has said. It’s keeping an open mind, but it’s also giving yourself that grace, right? Looking at it as a first step.

So maybe you only ever wear black, and all of a sudden you show up in red. So you might use that as a learning experience, or as an experiment, right? Not I’m going to try red and it has to be a big success, or I’m never going to wear red again. It’s okay what would it be like if I showed up wearing red? Do I like that?

Same thing with your work. If it’s taking on a different type of file, it’s like okay, I’m gonna take this on, and I’m going to experiment with it. I’m not going to hold myself to the standard of having it go perfectly, having to love it the first time. Because I think that’s where we can really stop ourselves from taking steps is when we put those expectations and it has to be perfect or else. So I love that you approach style and work and all of it with a growth mindset. It is such a useful concept.

I am still sending. I have clients that I work with where we haven’t really talked very much. I find in the last week I’ve sent out to a couple of people that link to the TEDTalk that Carol Dweck did. If nobody has listened to that, highly encourage. We’ll link to it in the show notes. I highly encourage everyone to listen to it. So.

Estelle: I’m sorry. One other thing that came to mind. It’s something that I always encourage law students that are here, some are associates, is when you’re given a task to do a research project, it’s really tempting to want to say well, it could be this way or it could be that way and provide evidence for both but not necessarily take a stand on what you think is the best approach.

I always encourage law students like give an opinion, state your opinion. Even if you’re wrong, the partner is going to be so impressed that you actually took a stand and you supported it. They may say okay, that’s completely wrong, and here’s why. But they’re going to respect you more for having taken a stand than if you were waffling.

So I think if you can embrace that fail forward, I may be wrong, but I’m going to try to add value and I’m gonna try to think through it in a way that I can support why I think that attorney should go one way or the other. It’s going to help you grow that much more because then they can tell you, well actually, this is what I disagree. Then you learn instead of just being like, oh, no, no. I’m not going to make an opinion. I’m not going to assert myself.

Paula: I love it. I love it. I think on at least a couple of levels and thank you for sharing that example. Number one, I think just practicing giving your opinion, right? Practicing the skill of what it feels like to take a stand.

Because you’re going to start out doing that in a memo that goes to a partner that’s going to get reviewed before anything happens to you being that person who is making the decision, who’s stating your opinion to the client, and then living with that decision. So I think that the sooner you can jump into just practicing, the better because you’ll get used to it. You’ll get better at it. You’ll grow.

I think that second piece of it, which is let’s say you do state your opinion and you are wrong. The resilience you will develop from learning that failure is not the end, right? Failure is a step. If that happens, you get to move on from there having learned what it feels like to fail. For lawyers, especially litigators, I was one of them. In every case, there’s going to be a winner, and there’s going to be a loser. Rarely do you ever see a situation where there’s not one or the other. Sometimes you’re going to end up losing.

So if you can develop the skill of resilience and realizing okay, this is not the end. Maybe I didn’t win in the case, but we won some strategic advantage, or there was an upside here, or there’s closure or whatever. So it’s really just developing that skill set because that will give you resilience that will help you whether you stay on as a lawyer, whether you decide to do something completely different, but those are serious life skills. So that is such a great example. Estelle, thank you. Thank you for sharing.

Estelle: Oh sure.

Paula: Love it. You’ve talked a little bit about this, but I would love to know what you love about coaching professional women in particular about style.

Estelle: Oh my gosh. I love empowering women. Because I think for people who don’t easily know how to style themselves, it’s an impediment. It’s one that a lot of those people just don’t talk about. So they just feel bad about it. They worry about their style.

They either wear something that they saw on a mannequin, which happens a lot with my clients. Well, it looked really good on the mannequin, and then I bought it when I did not like how it looked on me. Or they buy a blouse that is styled a certain way on a mannequin. They’re like I don’t know how else to style this. I was only showing that one way.

But the whole point in all that I guess just what I’m trying to say is I think that like anything, style is a skill. If someone can show you that skill, it’s like let’s just remove that impediment. Not only does it remove the impediment when you wear something that you look and feel great in, but it’s the ripple effect of how it impacts your life. Your husband will smile at you more. The barista will compliment you on your outfit when you’re getting your coffee. It’s just fun. It’s a fun way to be.

It’s something that was such an easy tweak. Unlike going on a diet that may take you three months, you could put on a new outfit, wear it, and automatically elevate yourself. It may be kind of awkward when you first start. You’re like I’m not used to getting compliments, or I’m not used to attention. But once you embrace it and step into it, it’s just affects everything in your life, and it makes everything better, and it makes you feel more confident and then pursue those goals that you want to go after instead of shrinking.

Paula: Totally. Here’s my question for you. Because I always found as a lawyer, and less so now, but also I’ve mostly been virtual in the past two and a half years. As a lawyer, I always felt very constrained in terms of what I could wear and still appear as being professional. So my closet was full of black suits, gray suits, blue suits, pantsuit, skirt suits, conservative button down blouses. When I had kids and couldn’t iron things anymore, it became something comfortable underneath a blazer like a sweater or whatever. Conservative shoes, conservative jewelry.

So I still struggle with this wanting to express myself in a way that’s more individual. I work with lawyers. I’m also thinking well, I want to appear conservative. At the same time, I think the world is shifting, right. We’ve got with the move to more Zoom and traditional and lawyers working remotely and in the office along with just general societal changes. I feel like the framework is shifting.

I’d love to know your thoughts on how a professional woman lawyer can show up in a way that maintains whatever level of traditionalism she wants to maintain while at the same time having that unique self-expression that I think is a part of, what you mentioned earlier, distinguishing yourself right. You want to yourself in your professional work, the writing, the speaking, all of that, and how do you want to show up for that? So I’d love your thoughts Estelle.

Estelle: Yeah, I love this. I mean that’s actually why I started doing style for, in particular, women attorneys. Because so many of my friends were coming to me, and they were struggling. I kind of think of it as you progress within your career, I’d say you would probably first start off wearing the black and navy suits that your career service office told you to wear as a new associate, maybe blending in a little more.

But I find that at a certain point, you realize that you’re sick of blending in. You’ve reached a certain status in your career where you’re sick of looking like everyone else. What you’re putting on doesn’t even feel authentic to you. You look at your closet and say this doesn’t even feel like me. So I think that there are definitely ways you can distinguish yourself and still remain professional. In fact, it’s what I love to do. It’s how I’ve expressed myself.

You can wear bolder colors, but you don’t have to jump into wearing a red suit head to toe. You can try some red heels. You can try a red lipstick. You can have a little black dress, and then some red heels. Or put like a little black dress and some animal prints. You can dip your toe in the water and see how you feel with it. But I think there’s nothing more powerful than a woman who knows herself, and her personality shines through in what she wears. You can totally do that and look like a professional doing it.

Paula: I love it. I think that phrase of getting tired of blending in, that is it. Right? It’s you’ve reached that, and you do the parallel so beautifully. When you first start out, you’re playing it safe. You’re doing what everybody else does, what is expected of you. At a certain point, when you’re tired of blending in, love it. That’s when you get to develop and own your own style. Just like you would as a lawyer, right?

Just as the way that you would speak in court, the way that you would speak to clients, the way that you would decide what kind of relationships do I want to have? How do I want to show up on the phone? How do I show up in person? Like what is the way that I’m going to deliver the good news, the bad news. I think all of it is developing your own style, and finding a way—Well, first of all, figuring out what that style is, and then expressing it. So I just love that. Thank you so much.

Estelle: Yeah. The other thing to mention too is if style is not your jam, like I mean I love it. My husband is always amused, but I will scroll through shopping while we’re watching TV. It’s relaxing to me. He’s like I don’t understand that. I don’t get you. So if that’s not your jam, find someone who does understand it.

Because what I always tell women is that there is a world of brands out there that are great for professional women, and it’s not confined to the stores that are in your mall. There’s a huge wealth of online brands and stores that you may not have been introduced to. That’s my favorite thing to do with clients is introduce them to a new go to brand.

But don’t constrain yourself. Research the options that are out there. If you can’t do it or you don’t have the time, hire someone to do it for you. It’s a limiting belief to think that well all I can wear is something from Ann Taylor or J.Crew.

Nothing wrong with those stores, but there’s other brands out there that carry blazers that might have some kind of detail that makes it look a little edgy. Or maybe there’s a cool zipper, or maybe there is an asymmetry in a blazer that’s fun that feels a little fresh and edgy like you. You don’t have to go all crazy and walk into court with a motorcycle jacket. You can get the middle of it with a slight asymmetry in the jacket.

Paula: I love it with like a mohawk to match. I love it. I love it. Estelle, one of the things you just said reminded me of something. The way you talked about if you don’t want to do it yourself, you can always bring somebody else in to do it for you. What I love about that idea is that sometimes we are so used to seeing ourselves a certain way, and the people around us are so used to seeing ourselves a certain way.

I remember a career strategist talking about the difference between warm leads and cold leads. So when you’re looking for a job, a warm lead is somebody that you already know who you can reach out to who can help connect you to somebody else. A cold lead somebody who has never met you before.

So this particular strategist was saying you want to talk to your warm leads. If they can help you and they want to help you great, but those warm leads are going to see you in a different light than the cold leads. So what you really want to do is put yourself in front of people who don’t know you, who don’t have a preconceived notion of who you are and what you’re capable of and what kind of a role you’d fit well into. Because they might see you completely differently.

So to draw that parallel back. If you are seeking out style advice from somebody who is just seeing you for the first time, they might be able to imagine and have the vision for you that is so much more in alignment with who you are now versus who you think you are. So I just think that’s a really neat idea for anybody who’s curious to just experiment with, right? See what other people come up with.

Estelle: Exactly. I always say have fun or go experiment in your own closet. Put things together that you wouldn’t think would look good together, and you may land on something fabulous. There’s no harm no foul. Play with it, see what you can come up with. If playing with it is daunting or scary then find a guide. It’s just clothes. It is just clothes, but at the same time, the impact of how you feel when you wear clothes that make you feel amazing is huge.

Paula: I love it. Question for you. So one thing that I think is really powerful as a professional, and we are talking about women professionals, is presence, right. When you’re in the room with somebody, and they just have a way of being present. I’m wondering what your thoughts are on how women can use style to enhance their presence.

Estelle: Oh my gosh. I have so many thoughts about this.

Paula: I love it. I’m excited to hear them. So is everyone else.

Estelle: Well one of the things that I think is when you feel amazing in your clothes, you are no longer thinking about your clothes. You are thinking about your argument. You are trying to be persuasive with your words. You’re not fidgeting in your chair wondering if your skirt is hiked up too much when you sit down or worrying if oh gosh this was really a bad choice on the neckline. I’m really hoping I’m not actually flashing opposing counsel. So I’m going to keep fidgeting with it and moving it around because I’m really uncomfortable. Then you’re not focusing on the task at hand.

So that makes you less powerful, less persuasive. So when you have it dialed basically style then becomes a non-issue. You can use your mental capacity in being persuasive in your job or in making a pitch or something like that.

Paula: Yeah, I love it. A few things seem to mind to me. Number one is fabric. As you were talking about, I’m hyper allergic to anything that is scratchy, like those wool sweaters. If I’m warm and I’m wearing a wool sweater, I’m immediately uncomfortable. I have such a hard time focusing on what’s going on in the room because I’m so itchy. I’m just like don’t scratch your face. So there are certain things.

At the same time, thinking about what we were talking about earlier, being intentional with your style when you want to appear crisp and clear and non-distracted. I mean that might be the look that you’re picking when you’re going to court versus you’re having a meeting with a client and you’re delivering some news that you know is going to be difficult. What is the approach you want to take? Do you want to be wearing the hyper black polished power blazer, or something a little bit softer because that’s the relationship you’re having?

So I just love that idea of what you wear being sort of that initial milestone. Once you’ve cleared it, you can move on and focus on what you’re there for. So I think that’s a really powerful way to think about it.

Estelle: Right? What you just said too is you can have different styles based on the occasion, like you just said. Thinking about who’s the audience, and how am I going to project? Do I want them to feel comfortable with me, like you mentioned?

Like I’ve worked with people who are family attorneys, and they don’t want to come across as these hard charging people all the time because their clients are telling them really sensitive personal information. So they want to come across as relatable, as kind and yet knowledgeable. So there’s so many different personas that you could create, but you can also tweak it depending on your audience.

There’s a whole other line where I can get into the psychology of color, but I won’t because that’s a long discussion. But there are ways that you can also pick colors intentionally based on the message you want to send. If you want to send a powerhouse message, maybe you’re gonna wear red or black. But blue is a color that’s very relatable, and you come across as responsible and reliable.

Paula: No, I love the psychology of color. I wish we had more time because I would totally ask you to go down that route. Because for all of us these are things that we don’t necessarily think about consciously. But once you are aware of it and you start making those choices on purpose, you might realize okay now I understand why it is when I’m meeting with this particular client, I want to show up a little bit differently. Because the message that I’m sending is of a different nature.

Not just at work, right? Like this is also with our families and with our friends, and how do we want to show up in different relationships? If it’s a weekend or if it’s Monday morning? Speaking of Monday mornings, sometimes it’s dressing the part that you wish that you felt as opposed to how you actually feel.

So you might be feeling like this is going to be a tough day. I’m not really feeling very motivated. Whether you can shift that, and I think you can, by choosing to show up intentionally in your most professional setup versus if you’re working at home, rolling into your pajamas and just saying okay, I’ll just try to make it through the day. It does have an effect on us. So.

Estelle: And the whole look good, feel good. If you’re in kind of a bad mood and you put on a bright green, I mean you can’t help but smile if you’re wearing something fun like that you know? It can help you turn your need around. As much as the message is that you’re sending to other people, you’re also sending a huge message to yourself. You see yourself in the reflection everywhere you go. You send the message that you care. You care about yourself, and you care about how you show up. It matters.

Paula: I totally agree. You said this initially, but I think it’s worth highlighting again. It’s not as though style is one certain way that we need to show up that is the way that everybody looks on Pinterest or on the cover of the magazines or anything like that. I think it’s, again coming back to ourselves and thinking about how we like to show up? Do we like to show up sort of—

I mean I’ll use the example I never paint my fingernails. I love it when other people paint their fingernails, I don’t do that for myself. That, to me, feels right. That’s my style. So it’s not necessarily have to do something. It’s that we’ve chosen it on purpose, and we feel good in owning that decision. So I just think for all of us, again, it’s not looking like somebody else. It’s being intentional and who we are. So I just love that.

My next question for you Estelle, and we’re getting close to time. So I don’t know how many more questions we have. But here’s one. How do you recommend letting go have an old identity? How do you move from, say, playing it safe to taking on a more bold or a more distinct identity for yourself?

Estelle: Yeah, I think it takes a lot of intentionality because we’re just creatures of habit. So if you’re not intentional about it, you’re gonna feel more comfortable going back to old faithful. So there are a couple ways I think you can go about curating or creating this new elevated look. The first is having a visual.

So when I’m working with clients, I do an exercise on Pinterest. It’s really just for them to kind of not think a whole lot about it, but just to kind of find things that they’re drawn to. They don’t know why, but they just are and just make these quick decisions. Then you can have a Pinterest board or do the good old fashioned vision board, right. Where it’s something that you can refer back to whether it’s a vision board that you put on poster board and you have it in your closet, or it’s a Pinterest board that you look on your phone.

When you’re making shopping decisions and trying to purchase new things, you can just say does this look like where I’m going? You can literally look at the Pinterest board be like no. No. That that would be old me not new elevated me. That can be a good check in point just to be like nope. We’re not making future decisions based on my old persona.

But another thing that I do when I’m working with clients is so after you figure out where you want to go and you’ve come up with this new style statement. When you’re going through your closet and you’re trying to decide what earns its way back in the closet, a question you can ask as you pull up a garment is does this say badass professional or dumpy housewife? Okay, that’s gotta go.

Paula: I can tell you what’s in my closet right now. But that’s totally off topic.

Estelle: I’m using this as an example. There are many things I’ve said okay, that’s a dumpy housewife. Gotta go. So no judgment. But like asking the question does this go—Paring down. Like just do your skirts one day. Do your blazers one day. You don’t do this all in one fell swoop but go through and just ask this question.

Does this convey whatever that style statement you have? Or does this convey relatable knowledgeable professional when you’re looking at your work clothes. If it doesn’t, then that’s like a really good litmus test, and just make quick decisions. Be like, nope, nope, and get rid of it. Then you start filling in with the new clothes that you then, again, base your decisions on that visual or that Pinterest board.

Paula: Estelle, I’m like nodding my head and in so delight with everything you said. Again, I’m thinking about your closet. I’m also thinking about all of us in our work, right? It’s how our jobs evolved. The things that we did five years ago, for example, maybe those are no longer in our work closet.

Estelle: Yes, exactly.

Paula: And someone else gets on. I just love that idea of being intentional and having that future vision. Okay. Here’s the Pinterest board that reflects how I want to show up. There’s also that notional Pinterest board of where I want my career to be going.

So in your practice in terms of your own style, in terms of your career, how do you gauge how far out you want to go, right? I mean we’re all evolving, and the world is changing and the styles change and the jobs change, ways that people work change. So how far ahead do you recommend looking when you’re creating like a signpost? Whether it’s a style guidepost, whether it’s a career guidepost, and maybe it’s different for each of them, but how far out do you recommend looking?

Estelle: Yes. That’s such a good question. You know they always say you could do the different approaches where you could have what’s my 20 year approach, what’s my 10 year approach, what’s my one year approach? So there’re different ways of looking at it.

But just in my own career, I think that I’m always wanting to grow and learn and see how I can improve or hone my skills. I think in other positions where I’ve been in, there comes a point where you’ve kind of maxed out. I don’t know, I like a new adventure. How can I parlay what I’ve done to then pivot and learn and grow even more in a different direction? So I don’t know if there is a concrete it’s at this moment. I just feel like it’s a gut check. That you feel.

Paula: Yeah, I feel like that’s how it happens, right? It’s like we’re on a path things are going. They’re fine. Then it’s almost like you hit a wall. You start to see wait a second. It’s time.

Estelle: Yeah. Oh, sorry. Like you said, you can embrace where you’ve been. It’s not a rejection. Everything you do builds on each other. It just gets you closer to that next big decision. So it’s not a rejection per se of where you’ve been or what you’ve done, but it’s like you’re building a tapestry, right? Every piece has its part. But if you want to be intentional sometimes you just shift and pivot.

Paula: Totally. I think for going back to what you said earlier, having those different points in time. I think sometimes I love doing the 1-3-5. I love the 20. Each of them brings to mind a different stage of where you’re going to be, right. It’s a lot more accessible to think a year from now.

So maybe if you’re doing it with your notional Pinterest board, how you look or how you practice or what you’re doing five years from now, it’s a bit harder to define because it’s further away. But with a year you can say okay, I know where I’m wanting to go, at least notionally. What does that look like with more granularity?

Both in terms of style, so picking what that’s going to be, but also in your work. Okay well, I know that the nature, the substance of my day to day isn’t going to be completely different unless you completely change jobs or do an overhaul that has a quick transition point. But for most of us, it’s building what we already have, and then deciding okay, I’m going to weave in more of one thing, and I’m going to let go some of this other thing. So I just love chatting with you Estelle. I wish we had… You’ll have to come back.

Estelle: I feel the same.

Paula: You’ll just have to come back. I’ve got ideas. So one last question for you, and then I would love for you to share where everyone can find you in terms of your Facebook group, in terms of the type of work that you do. If you could go back in time, right? Estelle who is graduating law school. You’ve gotten those black caps on, and I don’t know if you throw it in the air. I can’t even remember if we did such a thing. What would you share with her going back however many years that is for you?

Estelle: Gosh, I think I would tell her that it’s not as serious as you think it is. Because I think when you first start, that whole imposter syndrome. Like I’m gonna ruin this. I’m gonna mess this up. I would tell her to have fun, to explore, but to have intentionality and create her path. That it doesn’t have to be created for her. That it’s okay if it changes and pivots along the way as long as you’re true to yourself, and know that you will get there, wherever there is, and just enjoy the ride.

Paula: I love it. Estelle, you’re such a gift. Thank you. For everyone who would like to have more Estelle in their life, which I think everyone listening is probably like yes, please. Where can we find you?

Estelle: Yeah, I think the best place to find me is in my free Facebook group. A long time ago I tried to constrain and figure out okay where on social media don’t want to have my presence. I really focused on the Facebook group because it’s a lot of women attorneys. It’s women who care about their careers and who want to be more intentional.

So it’s called Powerhouse Style. I’ll send you the link. You just have to answer a few questions so I can kind of get a feel for what it is you want. I just provide a lot of encouragement, style tips and advice, and just share things. Share things that I’m finding that I like that maybe it benefits others. There’s just a lot of other badass women in the group who are professional and like-minded. It’s just a really fun almost a curated group of women badasses. I’ve said that a lot. Sorry, I probably shouldn’t keep saying badass, but that’s the word that comes to mind.

Paula: That’s okay. It’s one of my favorite words. I love it. Estelle, thank you so, so much. It has been such a pleasure. We will provide that link in the show notes. So for anyone who’s looking for it, you will find it. If you can’t find it, you can always send me a note, and I will send it to you. It has just been such a delight and such a pleasure. So Estelle, thank you. Thank you again for joining us. It was such a pleasure to have you here.

Estelle: Thank you. I’ve had a blast. This has been so much fun.

Paula: Oh, me too. Thank you for everyone who joined us this week. I hope everyone’s having a fabulous week. Yes, I think we will have to find ways to bring Estelle back for more. Take care everybody, and we’ll see you again next week. Bye for now.

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