Thanks to her gifts as a psychic and intuitive career coach for professionals, Jessie DaSilva has a knack for pairing people with the perfect career – and a new dream job to match within 90 days. 

She’s ideally suited to work with lawyers because… she used to be one… until she found a career that was a much better fit, one that inspired her to help others follow their passions.

In this episode, we discuss her career journey, specific ways she helps her clients (many of whom are attorneys), and more, including…

  • The biggest mistakes people make on resumes and cover letters
  • The right way to network to achieve career goals
  • Why you might already have more intuition than you think (and how to harness it)
  • How to handle the negative emotions of others
  • And more

Listen now…

Mentioned in this episode:

  • Jessie’s Website
  • Instagram
  • Facebook


Davina Frederick: Hello and welcome to the Wealthy Woman Lawyer Podcast. Our mission is to provide thought-provoking powerful and practical information to help you in creating your own sustainable wealth-generating law firm without overwork or overwhelm so you can live your best life. I’m your host, Davina Frederick, and I’m here today with Jessie DaSilva, CEO of Jessie DaSilva coaching. 

Jessie, formerly a practicing attorney, now is a career coach for professionals, including other lawyers, who uses her psychic and intuitive gifts to help her clients secure their dream jobs within about 90 days. Welcome, Jessie. I’m so happy to have you here on the Wealthy Woman Lawyer Podcast. I’ve been looking forward to it. 

Jessie DaSilva: Me too. Thank you for having me. I’m so excited. 

Davina: Great, great. So we’re gonna have a lot of fun today. And I wanted to start out by getting you to kind of tell us a little bit about your journey here to doing what you’re doing today. Because before you kind of committed to being a career coach, you were an attorney, a practicing attorney, and you worked some kind of fun, exciting jobs. Not a traditional, you have some things in there that we’re sort of untraditional for attorneys. So share with us a little bit about your story and how you went, you know, from being, deciding to be a lawyer and then where that led you to here.

How Jessie Became an Intuitive Career Coach

Jessie: Oh, okay, yeah. I know I’ve had a bit of an interesting career path. I like to say that I did everything you could do in the law before giving it up. So if I’m being totally honest, I went to law school because I didn’t know really what else to do. I had always wanted to be a journalist. And that’s what I studied at the undergraduate level. And then I graduated in the middle of the financial crisis. 

So of course, like news organizations were hit harder than anybody else. So I was trying to compete with people who had 20, 30 years of experience for entry-level jobs. There was just nothing. So I said, Okay, well what do my skills translate to? Where else can I go? So I went to law school. And I actually really loved law school. I think I’m the only, one of the only people who says that.

Davina: I did not really love law school, but I love how you get education, you know?

Jessie: Oh, yeah, I’ve always loved school. I love being in classrooms. I love homework. Like, I’m just a big old nerd. So I loved law school. Then I had come out and I had a short stint with an estate planning firm. It was a solo practitioner and it really just wasn’t a great fit for me. You know, in law school trusts and estates is like, oh, somebody comes in and they have a secret family and they have like four kids from them and like three kids from their real life. And then estate planning in real life was not as fun. It’s like here, open up this program and fill out this form every day. 

So I was like, Okay, this is not for me. I ended up moving into criminal appeals after that. And I had done moot court in law school and loved it so much. So to me, I was like, Oh, this is gonna be fun. And, you know, I’ve always loved criminal law. I’m a huge True Crime nerd. Even now, like I love watching any True Crime documentary that comes out. I’ve seen it. I can tell you right now. 

And working for the state, I was in Tallahassee, Tallahassee, Florida, and I just realized that, I was like, Oh, no, I have to defend all these convictions and there are serious problems here. But, you know, you do your job for the state. Like, that’s my duty was to uphold convictions and kind of take my orders and keep my head down. And I did that for a year. And on a personal note, went through a breakup around that time and I had taken inventory of my life because I realized I wasn’t happy. I was, had made a lot of my decisions around my partner at the time. 

Then I decided, Okay, I need to change because I don’t like this job. I don’t like this city. I don’t like what, I just don’t like what my life has become. I always wanted to move to Washington, DC. So I decided okay, Now’s my time. So I bought a one-way ticket, I quit my job. And I, yeah, I know. I’m still like, I’m still surprised I did that. But I had come up with a networking approach because I’m not a natural networker. I’m pretty introverted, even though a lot of people are surprised by that. But networking was, never came naturally to me. 

So I had come up with my own system that like literally involves a spreadsheet and all of these things. And I said, I’m going to network my way to a legal journalism job. My heart was set on it. I said, I want to go back to like my original dream. I want to use my passion for criminal law and I’m gonna find it. And I was able to land a job. I got a job offer my second week in DC. And in that one move, I doubled my salary, which is partially geography, but mostly just the fact that, you know, I found a good fit. 

I found what was then my dream job and successfully negotiated something that I felt was fair compensation. I was there. I was at Bloomberg Law for two and a half years and really loved what I was doing there. But after a while, I basically just outgrew it. I was like, Okay, this is getting formulaic. It’s not really a challenge for me anymore. And I’m somebody who needs to be in a place where I’m continually growing and I can change whatever I want at any time. I don’t do well with authority, just being totally honest. And

Davina: Yeah, entrepreneurs are like that.

Jessie: Right. Yeah. So I had this moment where I said, you know, I’m highlighting so many people who are doing really incredible things in criminal justice reform and I want to be part of the fight. So I networked my way to a job with the National Association of Criminal Defense Lawyers. And I loved the organization. I loved all the people there. But I knew fairly early on that it wasn’t exactly a good fit for me personally, as much as I absolutely adored my boss and everybody I worked with. It’s just I love that organization so much. 

So, but I knew it wasn’t the right fit for me. It was just, I had it built up differently in my mind. And so I just kind of realized, Oh, this isn’t really a good fit, but I’d stayed because I networked my way there. I never sent in like a cold job application. It was all through like my personal contacts. And they were so happy to have me and I was so happy to be there. And, you know, I was making good money and I just, I felt like I needed to stay. So I stayed for a while. 

And while I was there, I was saying like, Okay, well if this isn’t it, and I know everything from where I’ve been isn’t it, I need to figure out where I’m going and what I actually want for myself. So, I had been in the midst of it, I had been really deep into like my own fitness and my fitness and health journey and I had been helping others with that. So it had given me a taste of what it’s like to coach other people and I really enjoyed it. But I felt like it was too limited. Because I was often giving advice on everything else because it’s all, it all fits together. 

So by that point, I said, Okay, you know, I think maybe I actually want to be a life coach, which sounds really, really out of nowhere, except that I realized it was the thing I had been doing for free my entire life. I’m the oldest of four kids so I’ve been, like those were my original three clients were my younger siblings.

Davina: Whether they liked it or not. 

Jessie: Absolutely. And I had also, I’d always adopted interns at my job. I was always like, helping them get jobs. I do volunteering as a mentor with different organizations. I was always helping my friends get jobs. Like, I had it down to a science and I was teaching people, teaching it to people and it like dawned on me out of nowhere. I was like, I’m doing this for free. I wonder if people would pay me to do this. So yeah, I meant, you know, I’d always had friends like joke and tell me like, you should be a life coach. You’d be such a great life coach. But you know, that wasn’t really a career I was told is acceptable. 

So for many years, I just thought like, well, no one actually does that. Life coaches are a thing people laugh about. It’s not like a real career. And so I said, You know what, I think if I’m giving away this information for free and it’s working for these people and I’m helping them so much like, I think I could get paid for this. So I started before leap, before I like made any kind of jump, I took on a couple pro bono clients just to see how do I like this? 

Can I help them? Can I get them results? And I did. And I was lit up in a way that I had never been lit up in my life. So I knew that like, Okay, I think I nailed it. I think that this is it. And then oddly around the same time, I was going through what felt like a spiritual reawakening. So when, like, I’d always had, let’s say, like a sixth sense. I mean, I was one of those little kids who made adults uncomfortable because I could like talk to them on their level. And I would like tell them what to do and stuff and they, it was always very, like, I learned to shut that down because of like the looks I would get and like, Oh, well, you can’t really say that and things like that. 

So, and ao around, this was 2019. I’d had this feeling in early 2019 like something’s coming. Something big is coming, like I know it. And I felt like this need to just clear space. I went and I’d always been somebody who is a bit of a hoarder, not literally, but like I place emotional attachment on a lot of things. So I felt this need to just like get rid of all my junk. So I went in it, I went into it full blast, like I did nothing but that for like, every weekend. And I completed that within two months. 

And all of a sudden, once I had all of this room and all of this space, it was like that sixth sense kind of started getting weirder. So I’d always had this thing where it’s like, if I was thinking about somebody a lot, they’d call me or text me or something. But this was, I was starting to see more synchronicities around me. So not just that, but I would have dreams about pretty mundane things and then they would happen a few days or a few weeks later. So that’s kind of weird. 

Or I’d have a conversation with somebody and then I’d have a separate conversation like days or weeks later where somebody said my exact words back to me. I was like, Okay, this is like too weird. So I did some research like, Okay, what is this all mean? And I realized that intuitive gifts are just like any other skill. It’s just like singing. Everybody’s capable of singing if you were to undergo some training. Some people are naturally gifted and some people have to work at it a little more, but everybody has it. 

So I decided to like follow it and deepen it. And I’d always been, despite being a Catholic for like, going to Catholic school for 13 years and very devout for a lot of my life. I got to this, like I’d always loved psychics, I’d always loved like astrology and tarot cards and things like that. And I’d had a couple of tarot decks but hadn’t really read before. So I said okay, let me see if I can, like direct my skills into like certain channels, right? So I started reading tarot and I started doing automatic writing. And it just popped off. I started doing it for friends. 

I practiced a lot with friends first. And then after a few months, when I hired a business coach because I was ready to like, actually start getting people to pay me for my life coaching, I happened to hire somebody who also had intuitive gifts. And she was saying, like, you know, you can’t just show up as half of yourself. You know, yeah, and I’d had a lot of shame and embarrassment around, like calling myself a psychic, calling myself an intuitive. I’d been a lawyer, like I went to law school like and I had all of these people who’ve known me for so long. They’re gonna think I’m nuts if I come out and say this. 

And she was saying, like, you know, you can’t show up as half of yourself. You can’t just, you can’t keep the like, the life coaching separate from the readings because that’s just two different parts of you and like, you’re all of it. You’re the whole deal. You need to like, bring it together. So I started doing exactly that. And I started taking on paid clients. And what happened along there is as my passion for this grew, frankly, I just wasn’t showing up in my job like my nine to five job in the same way. And I ended up getting fired. Well, I was asked to resign, which I did. 

And it ended up being the biggest blessing of my life because it gave me a clean slate to dive into my business and start out. I just took it as an invitation to really trust myself and trust my business. And like the rest is history, as they say. This is what I’ve been doing now for about six months. And I can’t imagine doing anything else with my life because I feel so aligned. And I love my clients so much. And I love all of the results I’m getting them. And it just, I make my own schedule, I’m my own boss, which, you know, having an issue with the story. It’s like the perfect arrangement. So yeah, that’s the Reader’s Digest version.

Davina: Yeah,  that’s a wonderful story and intriguing journey that you’ve been on. And I, there’s lots to unpack there. So one of the things that comes to my mind is, you know, you, a lot of your clients are other attorneys who you’re helping them to find the right career, the right path for them. And, you know, attorneys, generally speaking, are and I’m being general, are a skeptical lot. What has been the reaction that you’ve gotten from that and how do you handle it?

Jessie: Well, I actually welcome the skeptics. I love it because I know my gifts and I know like how good I am. I’m very understanding and I’m very open. And I think it helps that I fully believe like, especially lawyers, I think are naturally in tune with their intuitive gifts. And especially anybody who’s like working with clients or having to do litigation, like you have it. You have intuition. The thing that makes you, that gives you that like hunch, like, I need to ask this question or I need to like file this kind of discovery, like those little hunches, that’s exactly what a psychic gift is. It’s an extra-sensory capability that you can’t quite explain. 

You just know, you just feel it. Or, you know, if you’re like somebody who when you go into rooms and you can like feel the emotion and kind of get a vibe, if you’ve ever walked into a room and been like, woof, I need to walk back out, you have intuitive gifts. So I love the opportunity to explain it. And then the other thing I have found is that y’all are a bunch of closeted woo people, okay? 

Davina: We are, I know.

Jessie: Everybody has a craving for something that’s a little spiritual, a little magic. And so I have found that like, there aren’t as many skeptics out there as there are people who are open to it. And I think that that’s, I think lawyers are, I think the reason lawyers are more open to it is because they know that they themselves have spiritual gifts as well. They just didn’t have a name for it. It’s like, Oh, I’m just really good at guessing or I’m really good at reading people. All of that, that’s all psychic gifts. 

Davina: Right, right. So how do you transform, you talked about this a little bit in your own story, but how do you transform your, those sort of sixth sense feelings of intuition and things like that, that have evolved over working with a lot of people and getting that idea, you know, where you can just tell immediately red flags are popping up all over the place when you meet certain people. Other people you meet, you’re just like, oh, wow, this person is awesome and we’re gonna do great things together. How do you translate from that into a psychic gift? Can you go a little deeper into that?

A Sixth Sense is a Practiced Skill

Jessie: Sure. It’s really, it’s practice like anything else. So for me, what was really helpful was learning how to get grounded and learning how to trust myself. So a big part of it is self-care and like not burning out and managing your energy, that’s a big part of it because you can imagine that if you’re like stressed to the nines, you’re not gonna be able to listen to that little voice inside you as much as you’d like to. So part of it is getting grounded getting rested, learning how to manage your energy. 

The other part of it is just trusting that whatever comes to you is correct. And that was a weird one for me to embrace when I started doing, when I would start doing like readings for people, I started doing a lot of free readings. And the, I was afraid to read for strangers at first. I was also afraid to read for my friends. I’m more afraid to read for friends now than I am strangers because I would say things like something would pop into my head like specific things and I would say like, I remember one time I was saying like, Oh, some guy you’re seeing or something, I was like, he’s got some kind of thing to do with fish. 

I don’t know if that means he’s a Pisces, or I don’t know if that means like, he’s into fishing. I don’t know what it is. And this person was like, What the fuck, he just left to go on a fishing trip. And I was like, oh, like weird. So I just had to adopt this feeling that anything that pops into my head, I need to say. It’s not my place to decide if it’s relevant. It’s just my place to say it and, you know, the other person’s interpretation is just as important as mine is. So I just conveyed the information. That’s what I’ve learned. 

Sometimes things come out very, like sometimes things come out like very, I’ll say blunt. So sometimes I get not so nice messages to pass along. I’m like, Oh, I can’t see it like that. And I feel like, and I’ll like avoid saying it. Like I’ll just like, start talking about other stuff and it’s still nagging, still nagging, still nagging and I’m just like, oh god, I gotta say it. I was like, I’m so sorry. This is gonna sound mean but here you go. And normally those people are like, oh, oh my god, like I really needed to hear that but damn that was harsh.

Davina: George is sending me that message. That was the way he used to talk.

Jessie: It just it’s like, feels like a nagging feeling. So a lot of times people like I’ve tried to describe what it feels like and so, because my two strongest gifts, as they say, are its clairsentience which is emotion and feeling. The way that feels is like I feel emotions as if they’re mine. Like as if I’m experiencing what’s going on. So for example, I was watching like the Love Is Blind finale, which is amazing. It’s so good. If you haven’t watched it, it is totally binge-worthy. But and I, like these people were going to the altar with, you know, people they’ve been like dating for six weeks. 

And I looked down and I was sweating through my shirt. I was like, why am I, like I don’t even know these people. What is going on? But it’s like, the best way to describe it is like if, when you know it’s gonna rain, but there are no clouds yet, like there’s no clouds, there’s no wind, but you just like walk out in the morning and you’re like, ooh, the air pressures off. It’s gonna rain today. It feels like that when you’re feeling other people’s emotions, which I think a lot of people can relate to. 

And with like the, my other one which is clear cognizance, that’s a just intuitive knowing, which is a little, it’s a little weird to describe because people are like, Well, how do you know like, when I really like focus on it my thoughts like, I don’t feel anything in my head when it, when I’m thinking it’s just you know my natural like biology. Like, I can’t tell you like, my thoughts I don’t feel anything in my head. But when I am getting like a channeled message I do feel a little dull sensation like in my head it’s like in the back of the head. It’s almost like it feels like my thoughts, I just feel something. I call it like a brain tickle. 

Davina: Like your spidey sense?

Jessie: Yeah, yeah, exactly. I used to call them spidey senses before I had any idea of what these were. But it’s just like how and I think a lot of lawyers will relate to this, when just a thought pops into your head and you’re like, I don’t know how I know it, I just know that it’s true. That’s really what it is. 

That is like, that’s what psychic knowing is. It’s just, and I think that that’s what a lot of lawyers are familiar with are probably those two, knowing that like feeling the emotions of your clients of other people and then probably just knowing, knowing what’s going on in this case, like knowing what that person is saying, it, knowing whether someone is lying, knowing whether someone is telling the truth, all of that. Like, it’s the things we can’t really explain away.

Davina: Right, right. I certainly have had the experience of sensing client emotions to the point, you know, because I, when I’m coaching my clients and I have a, I have a client who is having a lot of negative emotions around money or a lot of fear or something going on in their life that’s causing, you know, I’ll be talking to them and if I don’t shield myself, if I don’t do some shielding and some cutting and things like that, then I will notice, in my own, you know, the next day I’ll be sitting there or later in the afternoon, I’ll be sitting there and I’ll be worked up and feeling very emotional about something and upset and then I’m like, wait a minute, this is not mine. 

This is not me. This is not going on in my life. But you absorb those emotions, you know, from other people sometimes. And then, and I think that happens with a lot of people and we don’t realize what it is. Like, we’re not calling it that, you know, it could just be, you know, thinking, Okay, I was around somebody earlier, and now I’m in a bad mood.

Jessie: Right. And I think women, it’s like, you know, everybody talks about women’s intuition. And I think it’s, I mean, part of it may be a predisposition to it. But I’d say it’s also socialized as well. We are raised to think about everyone else other than ourselves. So we have literally grown up trying to guess the emotions of other people, which is why we end up performing a lot of emotional labor and our relationships. 

It’s why like people talk about like women being nurturing and natural mothers. I don’t think that’s true for every single person, but there’s definitely a societal influence that’s like taught us to take on the emotions of other people and to presume like to try to fix them. So when, and a lot of times what we need to do is exactly what you’re talking about which is releasing those emotions because they’re not ours. And so yeah, I think it becomes, it’s something that naturally dogs women and women attorneys more than other people.

Davina: Right, right. Well, and it could be too, you know, a lot of it depends on your family environment and that kind of thing and how you grew up because, you know, you might have in your, your position in your family of origin, may have tamp down gifts, you know? Particularly if you grow up in a religious family maybe, you might have that experience where you’re like you mentioned earlier about being Catholic and yet you still have these other beliefs there. You know, and I’m sure growing up to the Catholic Church, you were told, well, no, that’s, this is not something that’s acceptable, right?

Jessie: Right. Yeah. Oh, for a long time, it was, it felt very taboo to me and I wouldn’t explore it at all. It wasn’t until I was, you know, in my 20s when I was like, Okay, I’m allowed to enjoy this. And I’m allowed to do this anyway. Like, it’s like, I’m allowed to enjoy these things. They’re not mutually exclusive. And then I just kind of got to a point where I said, I don’t want to have two different sets of spiritual beliefs. 

I want them to be together. So that’s like, kind of how I left the church in the past. But, you know, it’s I still, I mean, I still carry a lot of those beliefs with me. It’s just I don’t, you know, have I’m not part of an organized religion, which I think is just, again, having problems with authority, probably best suited for me.

Davina: Well, let’s talk about how your gifts have helped you help your clients. Because in addition to, you know, you do things like help them with a resume and help them understand how to make connections and networking and all of that you might associate with a career coach, right? So, what kind of, how do you use your gifts to put a different spin on that, let’s say?

How Jessie Helps Her Clients

Jessie: Sure. So it, you know, I’m gonna I’ll tackle the written materials first since that seems like the weirdest one to combine the two. But basically, when I read people’s resumes or their cover letters, I’m able to get a sense of the mindset from which they’re writing it. So a lot of times I see like by how someone’s written their resume how they view themselves. So a lot like, for, I’ll use my sister as an example. So she had, when I had originally looked at a cover letter she took a crack at, I had said, am I allowed to curse on here Davina?

Davina: Yes, you are. That’s fine.

Jessie: It’s a small one. Okay, so I

Davina: I don’t think it’s like, you know, we’re not governed by the,

Jessie: I read her cover letter and I had said to her I was like, do you know what a pick me ass bitch is? And she was like, What? No. And I was like, okay, it’s a new term. I was like it basically describes a person. It tends to be like a woman but it’s like a woman who puts down other women in order to look more desirable in the eyes of a man. 

She’s like, so desperate for his attention that she’s just like, Oh, I’m not like the other girls or she says, she like changes our personality to be more desirable. And I was saying your cover letter has major pick me ass bitch lines, but for an employer. It was like we were like so insecure here that it sounds like you’re bragging from a place of insecurity. 

Like, it does doesn’t match. And she was just like, oh my god, I’m so embarrassed. I was like, it’s not a big deal. It happens. I just want to explain to you what it, why I’m going to rewrite it. And so then from there, I, you know, I always do like a session with somebody to like, talk with them while like to do a cover letter or resume because I want to hear how they describe things because my goal is not to write anything in my voice. I want to write it in somebody else’s voice. 

So I see how they describe their job duties. They describe what they do, what their goals are, how they explain like successes they’ve had or achievements and I just take notes on all of that. And then I just translate it to basically come from a place of quiet confidence of like, I know I deserve this job. I know my worth. And like, this is how I’m showing it. It’s just, it’s not show offey, it’s also not too humble. It’s like striking that balance of self-assurance. So that’s how I handle it with like written materials. When it comes to the

Davina: Before you go on to the next part, let’s address that. Because I think that that is something that is again making, you know, we’re making general statements when we’re talking about women versus men or whatever. But it is something you and I both work a lot with other women lawyers, and one of the challenges I’ve seen is that, is confidence as compared to working with men. 

When I’ve worked with men, the level of confidence is different. I mean, we’ve all heard the joke about, you know, like, I wish I had half the confidence of a mediocre white man, you know? But and so there’s some truth to that, and particularly when it comes to sort of tooting our own horn and talking about what we bring to the table and negotiating our salaries and things like that. 

I think it’s a very common issue with women and I think women sometimes, like, go totally to try to overcome that, they’ll go totally the opposite of that. And they come across as more like, I’m a boss baba, you know, and it comes off as a little bit more arrogant. And like you said, sort of from that place of insecurity instead of from a place that’s just being really confident in who you are and what you bring to the table. So I think that’s a huge, huge point that you brought up.

Jessie: Right. One thing I always say is that we’re so much harder on ourselves and it’s not unique to women but we are also much harder on ourselves than we need to be. And I say that it’s, you are just viewing your life through shitstain glasses, just like you can put on rose-colored glasses and see the world’s like all rosy and beautiful and full of blush, and opportunity. I think women, especially, but lawyers, even more so. Like, law school trains us to think in worst-case scenarios. We have built an entire career on key, on like managing other people’s expectations. So it’s like, oh, I don’t want you to like, I don’t want to over-promise anything. 

I want to like, tell you what the most likely scenario is, not the best-case scenario. And what happens is we start to internalize that with our lives. So we’ve basically been conditioned to think that way so we bring it into our futures. Well, I need to manage my expectations. I may not get that job or I need to settle. I need to be, I’m probably not going to make over X amount or they probably won’t accept this counteroffer or, you know, we start to manage our own expectations and I’ve seen a lot with lawyers. 

Generally, we almost turn off that part of us that allows us to dream, that allows us to have high expectations and high hopes and believe that we can achieve something. That we can get to the point of, Okay, I can change the world and I can make money doing it. We tend to think it has to be one or the other. We have to like, think that, okay, well, I have to work really hard to get there. All of those things, those are all limiting beliefs. Those are all things we’ve told ourselves and so we create that reality to give ourselves proof.

Davina: Right, and it’s also a very competitive field. And so I think a lot of people always, you know, I’ve talked a lot about with my people about their being more visible, being visible and putting yourself out there. And there’s a lot of fear around judgment from other attorneys. Like if I go out and create this video, I’m gonna say something and other attorneys are going to come on my thread and go, nuh-uh. 

And I’m gonna be embarrassed and ashamed because there’s this high level of competition and just, you know, by virtue of the practice of law, right? We tend to put that, project that too onto ourself. That comparisonitis, you know, when we start going, no matter what I put here, there’s going to be somebody out there who, you know, Yes, I did moot court, and, you know, I got this trial experience. And there’s always gonna be somebody that’s, you know, was president of this and did that and the other and I’m going to come up short.

Jessie: Right. And the thing is we don’t realize that when people criticize us, they’re criticizing themselves. Like, secure people don’t do that, okay? Like, secure people do not, they’re not out there putting you down because they are so good at what they do and They’re so confident. They’re putting you down because they’re insecure and they feel the need to like correct people. It’s all projection. 

Just like, one of the things I sometimes give people as an assignment is to keep a judgment journal because the most insecure people, yeah, you judge other people and typically the way we’re judging others is the way we judge ourselves. So like the example I like to use is, you know, I’m blonde and I have highlights, one thing I will, I’m like can sometimes judge people for like, oh, her highlights are so brassy. Which for those who don’t know, brassy is like when the highlights start turning like a brass color at the root of the highlight. 

Davina: Not a compliment.

Jessie: Not a compliment. No. I’m like, Oh my god, like, if I’m judging people on how brassy their highlights are, it’s because I’m so worried that my highlights are brassy. That’s like literally it. I’m so hyper-aware of it. I’m so concerned. It’s the same thing if you’re judging somebody on how, on their appearance, it’s because you’re preoccupied with your appearance. So it’s actually a really powerful tool to look at the way people judge you. 

And, you know, like, if you need inspiration, I’m out here calling myself a psychic. And, like, I, that was not an easy thing to do, especially when I have such a huge legal community as like part of my following. But you just got to do it. It’s like, it’s not, courage isn’t as they say, courage isn’t the lack of fear, it’s moving through that fear. That’s what it is.

Davina: Right. Right. And after a while, you get to a point where you’re just like, Oh, I’m just gonna flip on the camera and just see what happens. In fact, I saw one of yours with a bathrobe and a towel on your head. So

Jessie: Oh yeah. Somebody had, I was on a, I was a guest on another podcast recently where they were like, I saw a podcast, I saw a live of you where you were like, post-gym really sweaty, your hair was crazy and you were talking. And I was like, yeah cuz that’s what you get with me. I’m just, I show up as I am. I’m a real person. I don’t like, you know, sometimes for coaching calls, I’m in pajamas because I’m like, Listen, I need like, I cannot wear clothes, I cannot wear tight clothing. 

I am on my period and I am not putting on pants. So that happens sometimes, I’m just you know, I’m somebody who keeps it real all the time. So I, that’s what you expect to get with me. So that’s how I show up. That’s the main thing is you just have to be you. That’s, and that makes the entire difference. Especially like, even though you’re practicing law, you are the product at the end of the day. It’s not just the fact that you specialize in an area or you provide certain services. 

The reason people hire you versus other people versus anybody else is your personality. It’s just like being a life coach. It’s the fact that you are the product. They’re not hiring, they’re hiring you for who you are, not just what you can do because there are other bajillion people they could hire instead. What resonates is who you are and your identity and how you present and you never know what’s going to resonate with people. And anybody who doesn’t, yeah, anybody who doesn’t resonate with you, they’re not your people. That’s just how it goes. 

Davina: That’s right. That’s right. And you know, the worst thing you can do, as you and I both discovered because we both had been attorneys and then chosen other careers is, and I was in a different career part came an attorney, so I’m like totally a career jumper, is that finding yourself in a career, in a job in a situation where you’re miserable. I mean, better to be you and in all your glory, whatever that is, and be doing something that makes you happy, that defines yourself, you know, in a career where you’re checking all the boxes and you look good on the outside, but on the inside, you’re miserable. It’s not gonna last.

The Law of Attraction In Business

Jessie: Right. And I’m a firm believer that when you do what you love, the money follows. It’s just the law of attraction. I think that when you’re in your element and you’re aligned and you’re feeling like so good about your life and what you do, you become so sparkly and attractive to people, they naturally want, they naturally gravitate towards you. 

And what do they bring with them? They bring their money. They want to invest. It’s just I have so many female lawyers who come to me because they’re like, I don’t know what I want to do. I don’t know what my path is. I don’t know what like, what area of law I should be in or whatever. And then I say like, well, what’s your dream job? Because to me, that’s all I care about, really. And then they’re like, Okay, well, yeah, my dream job is to open a bakery but that’s like not real. And I’m like wait, hold up, hold up. Why is that not practical? 

Like there are bakeries that make money out there. Like it’s not like it’s your, it’s not like some shameful practice. You’re not trying to like sell cocaine, you’re trying to sell cupcakes. Like, that’s not crazy. But again, it’s because we’re viewing our dreams through the lens of our own insecurity. So I tell people, I’m like, do not come to me with your dream job if you’re not ready to pursue it. Because if you come to me as a lawyer, and you say, like, well, I’m like, unhappy in my legal career. 

So I think I’m going to try this area of law, but my dream is actually to open a bakery. Bitch, you’re opening a bakery. Like, we’re gonna work toward that. Like, I’ll get, I’ll help you get into a better legal job so you’re not as drained, but the next thing you’re going to do is you’re going to start catering. Like, I’m gonna like, that’s what I’m going to lead you toward. So don’t come to me for like, reasons why, like your dreams aren’t practical, like no, we’re going all in.

Davina: Yeah, yeah, I love that. So I don’t want to let time get away without talking about networking and making connections because I know I jump from one thing to the other, but I want to make sure that we cover that because I think so many, is one of the things that I hear the most from women attorneys who, you know, say I hate networking. I hate marketing, I hate whether it’s marketing themselves or their business, right? 

I hate going small talk. And they’ll hang it on things like, I just hate small talk or I hate other people. You know, but I don’t really think that they do hate other people. I think that they, it is a fear with, so there’s an expectation on what it means to network that is different from what it actually is. What do you, and maybe it’s a thing that people feel like they don’t want to, they don’t want other people to know that they need something or want something.

Proper Networking isn’t Supposed to Be a Drag

Jessie: Totally. Yeah. So when I say like, I’m not a natural networker, you know, my brother is a really great example of someone who’s naturally a good networker. He’s so charming. He’s outgoing. He’s like, just very naturally friendly, has a way of making you feel like you’re the only person in the room. Every Christmas he like, sends out cards and gifts and things like that. Like I am blown away perpetually by that. I’m not like that. I’m a little weird. 

I have very niche and strange interests. I’m like a closet goth. So you know, I’m like, Oh, yeah. Edgar Allan Poe in the permanence of death. Wow. So I get it. Like networking feels very weird. But what people say when they say that I hate networking is that they hate networking events where you have to go and talk to strangers and like have cheap wine and like, you know, you stand by the snack table because you don’t know what else to do.

 Yeah, I hate that too. Everybody hates that. But there’s no like there’s, that’s not networking to me. I always say if there’s networking in the name of an event, don’t go because the only people there are other people looking for jobs. Like there’s no point in going. Networking to me is literally just making professional friends. And when we make friends, we tend to make friends with people we like. We’re not making friends with people who we can’t stand. So that’s why my networking approach it’s like three prongs. 

So it starts with tapping into your current network. So you start there so you can get some easy wins because it’s all about like building momentum. So it’s about getting back in touch with everybody who’s in your industry, related to your industry, may know somebody in your industry, getting coffee or lunch with them, chatting them back up. And I don’t like to say like, Oh, I’m looking for a job. I hate that phrase. I always say like, I’m looking to transition into blank because it takes off the pressure. 

Everybody wants to help other people. I genuinely believe that. And they want to help when it requires as little work as possible. Giving advice is like as close to no effort as you can get. So I always tell people start with Do you have advice? Send out like a list of places where you’d like to work. Like, do you know anybody here? And then just ask who should I talk to? That is the magic question to ask everybody because your contacts will give you their contacts. Ask them to do an intro. It’s that simple. 

And then when it comes to networking at places where you’d like to work, using that phrase, like never saying, like, Oh, I’m looking for a job, but using email to get in touch with people, like, I make a spreadsheet. And this is a free tracker that I have on my website. I call it my networking tracker. You have a spreadsheet and you fill in any kind of company organization, firm, whatever where you’d like to work, and then you go on the staff and see if you can, you want to find somebody you have something in common with. And I like to go personal if you can. 

Like, alma mater, same kind of heritage, maybe like you’re from the same place or, you know, you are in the same kind of volunteer group or professional organization, find a personal connection. And you want to aim for like middle management, I mean, depending on where you are in your career. But you don’t want someone entry-level and you don’t want someone so senior that they don’t have time for you. So find somebody that you can relate to and then just reach out to them via email. If their emails are on the website, great. If they’re not, it’s really easy to find the configuration. 

Most companies and firms have the same kind of like first initial last name thing. So I like to check the press section because most press releases have a specific person you need to get in touch with. And I check events as well, because again, most of the time they have someone on staff that you need to contact for events. See what the configuration is there and send an email. And if you, if there’s really no email you can find anywhere, you can’t find anyone on LinkedIn, then guess and just use the bounce backs to guide you. 

But when I send an email, I just say like, Hi, I came across your name while doing such and such research. I noticed we have the same thing in common. I’m really intrigued. Like, I just was wondering if I could pick your brain for some advice over coffee, my treat. I’ve attached my resume so you have a better idea of my background and just try to set something up. Most of the time, and when I say like coffee, like I also say if you’re not available, I’d be fine with a 10-minute phone call. 

Most people will say yes to free coffee. And I say that like a $4 latte goes a long way. You’ll get a lot of info. And just me them. Like, meet them somewhere close to their office, pay for their coffee and just ask for advice and ask for a lay of the land in the industry and ask them for other people to talk to you. Because if you go in there and you’re like, Oh, do you know of any jobs, they’re gonna feel really uncomfortable and they’re gonna be like, Oh, no, I don’t. 

But they all know people and they all have advice. So if you go and you have, you contact three people that you didn’t know before this, and each of those three people gives you three more names, you just went from having zero contacts to having 12. So the whole point is just exponentially growing your network. And that way you, yeah, you’re like just recruiting people to your team for them to all like keep their ears to the ground. And when they find something, like, you want to be on their mind, so they send it to you. 

So after I meet with people, I always send a handwritten thank you note to them. And I try to like strike the balance between like, complimentary and personal, but not creepy. So you want something that’s not basic, like thanks for your time. I really appreciate it. You want something that’s a little unique to them and complimentary so they keep it. The point is that you write something nice enough that it either goes in their desk drawer or they put it up on their bulletin board. You want to stay in their like line of sight. So

Davina: I like that you say personal and complimentary, but not creepy. 

Jessie: Not creepy. 

Davina: What creepy is, I had so much fun. It was hearing about your pet.

Jessie: Yeah. You know, it’s like, it’s, I mean, it’s harder to be like creepy than you think. But like, for one example, somebody who was a little cold with me, I was like, ohh, I didn’t really get a lot from them so I said, I really admired your quiet confidence. You know, something like that where it’s like they’re not super animated. You just like want to, you want something, want to write something nice enough that they hang onto it. 

That’s the goal. So, because the next time they hear about a job opening, they’re going to see your name and they’re going to remember you because you have that, they have that thank you note from you. And then when it comes to events, I say focus on things you love to do. Focus on hobbies. So don’t go to networking events that are aimed at like, you know, professional development and stuff like that, unless you genuinely like the information and want to go. 

But it’s best to network in social settings because people there already have their guard down because they’re there to have fun. So like football watch parties for your alma mater, or say you like kayaking, so you find a group on that’s just like a weekend kayaking group, things like that. Everybody knows a lawyer. And it’s like, it’s one of those things where, you know, when your mom was like, Oh, so my friend’s son’s wife’s aunt is a lawyer. Like I, like she’s a lawyer. Maybe I can get her phone number, your mom is a great networker. Don’t turn that down, okay? So everybody knows 

Davina: It’s so funny that you said that about because when I, I remember when I had my own practice, and I was, you know, at networking meetings like traditional ones. And I would say, I was a lawyer and people would ask me some other questions unrelated to it, they wouldn’t want to talk about me being a lawyer, or they would say, Oh, you oughta meet so and so, and so and so did exactly what I did and was really of no use to me from a referral standpoint or anything like that, right? 

But what I found is when I started doing coaching, I would network and I would say, I’m an attorney and I’m a business coach, or, you know, to help other attorneys or other business, whatever, and they would always, or at the time, I didn’t focus just on attorneys. So I would say I’m a business coach, and people did not want to talk with me about being a business coach because they were afraid I was going to sell them something. And that’s what happens in networking functions. 

So they would always ask me about being a lawyer. Oh, what kind of law do you practice? So it’s really interesting how psychologically in networking situations, traditional ones, people kind of have their guard up because they’re afraid you’re going to try to sell them something. So financial advisors and the insurance people, it’s going to be, you know, and everybody there has got, we’re trying to make sales. 

We’re trying to get referrals. We’re trying to, and so they want to talk about anything but that in networking situations. And I had the same advice that you do, I think people limit themselves by thinking I have to network means I have to go to a BNI meeting. Why not, if you play soccer every week in a league, you know, if you love that, you’re getting the joy out of that and you’re gonna meet people.

Jessie: Right. Absolutely. It’s the same thing like with dating. Like it’s, you know, plenty of people like, everybody’s forgotten what it’s like to date without apps, you know? And it’s the same thing with networking and finding a job. We’ve become dependent on websites to like connect with jobs. But my thing is that if the stat is that 75% of jobs never make it online because they’re filled by referral, then why can’t they fill those jobs? 

Either because they have high turnover or nobody on staff wants to refer their friends to work there. That’s what I think. So my whole goal is like, I want you to be the person who knows someone, the person who has the in. I want you to be the person who’s benefiting from nepotism. Like, that’s the whole point. Because that’s where the good quality jobs are.

Davina: That’s your new slogan. Benefit from nepotism.

Jessie: Right. Like, I want you to be the person who has the in. That’s the entire goal because that’s where the good jobs are. The good jobs don’t need to be posted because they get filled. Like, people refer to their companies, if they love where they’re working, they’re, people are gonna actively refer their friends and their colleagues there. That’s just how it is.

Davina: Well, and if you become the connector because you’re out meeting so many people and talking to so many people, imagine what a resource you then become, like the kind of value that you add to relationships, because you’re out, you know, seeing people and you’re like, Oh, you know, I just met so and so the other day, let me introduce you to them, you know?

Jessie: Right. If you do like a successful networking run, you really only have to do it once because then it’s just upkeep. And I’m not, again, I’m not naturally good at this. So for me, I use spreadsheets and my planner and a calendar. So basically, seasonally, well, you know, when I was a reporter, I did seasonally with like my contacts. But in my professional life, every six months, I’d be like, Alright, it’s time to go down the list of everybody who’s in my network and try to set up coffee or lunch just to like, meet up with them again, say hi. Like, you know, keep those contacts fresh. So if you do it once like, you’re golden, then

Davina: And it can be fun. If you enjoy, you know, if you like to, if you don’t like small talk and you say you like real relationships, that’s what this is about is creating real relationships.

Jessie: Exactly. My whole thing is like, you know, there’s no, you don’t have to talk about small talk. You can get into the nitty-gritty. Like, there’s nothing holding you back. You have to show up authentically you, which is why if you’re looking to connect with people on a personal level, then you have a better chance of liking the people who are getting into your network and you want to keep in touch with them. That’s the entire point of this. And, you know, I say all the time, my goal is for all my clients to fire me. I don’t want them to need me more than one job hunt. If they do it right the first time, they can replicate it every single time. 

So that’s like, that’s my whole approach. Like I, I’m confident in what I offer, I’m confident that I can guide people through it. But the reason I have, like I created an online class just for networking, and the reason I created a group program for it is because most of the time people just need a little bit of accountability. And they need a little bit of support from not just a coach, but other people who are in the job hunting boat. Because it can be a really demoralizing and lonely process when you’re trying to find your dream job because you’re unhappy with where you are and you are doubting whether you can connect with what you really want. 

And then you have your friends were like you’re beautiful and amazing. And like it’s gonna happen when you least expect it and you’re like, cool, that doesn’t really help me. Also, you don’t get it because you like your job and you actually make money doing what you like, so you don’t really understand my struggle. That’s why I created an accountability system because, first of all, I’m a course junkie. And a lot of times I abandon my course halfway through, I forget about it, then I come back to it months later and like finish it up, but it just extends the process. 

So by having an accountability buddy, like accountability buddies who can like, you can come in and say, Oh man, like I’m feeling really down about this. I agreed to go to some kind of social event and I really don’t want to go but I know I should go. And then you have people who say like, I did it, I did that. I know how you feel. I did that last week. And I actually was glad I went. Like, this is what ended up happening. You need that to keep going because it’s hard, it’s hard to do it by yourself. If you could do it by yourself, you would have done it, you know? Like, that’s just the reality.

Davina: Right, right. Well, this has been really fun today, Jessie. I could probably talk to you for another hour at least. But we’re gonna wrap up right now so tell us where we can find you and find out more about you and your coaching services on the interwebs.

Jessie: Sure. So you can follow me on Instagram. I’m very active there. I post all the time. I do card readings and stuff, like card polls for people. My username there is J_DaSilva and that’s DA, as in apple. And I do have a website, it’s just And my Facebook profile is pretty open. Like I share everything. Like I said, I’m an open book. So I’m showing up there in my robe and my bath towel sometimes, showing up there post-workout. And I’m also showing up looking cute with a red lip. So, you know, you get all sides of me on social media.

Davina: Yeah, yeah. I saw one with you where you’re wearing a wonderful red coat and I was like, Oh, I had coat envy. 

Jessie: Oh, yeah. I love that one. What you didn’t see is that there’s a button missing on it. I need to sew it back on.

Davina: Okay, so I just saw the backside, so that’s the good side of the coat. 

Jessie: Oh yeah, I got that on a deal. Calvin Klein, but I got at Burlington Coat Factory. So, you know. 

Davina: Nice, nice. Well, thanks so much for being here today and sharing with us. I think people are gonna really enjoy this podcast. It’s a little bit different from some of the others we’ve done. But there’s a tremendous amount of valuable information in here as well no matter what perspective you’re coming from. So I really appreciate you being here and talking with me today.

Jessie: Yeah, me too. This was really fun. Thank you for having me.