Sherry Mason: Ambition, Prestige, and Knowing When It’s Time to Leave Your Firm

By Elle Brusse on June 15, 2026

Stuck on the “wrong mountain” in your legal career but unsure what to do next? In this episode, career coach and former lawyer Sherry Mason breaks down how ambitious attorneys can separate prestige from true fulfillment, avoid burnout, and plan a smart, strategic exit instead of a panic-fueled leap.

In this episode, Steve Fretzin and Sherry Mason discuss:

Ambition vs. prestige in legal careers
Skills, situation, and identity as sources of dissatisfaction
Burnout, autonomy, and control for lawyers
How spending 20% of your time on aligned work drastically reduces burnout
A five-step framework for planning a career transition

Key Takeaways:

Many high-achieving lawyers climb career “mountains” chosen for them by others, only to realize later that prestige alone doesn’t guarantee a fulfilling life.
Career dissatisfaction typically stems from one of three areas (skills, situation, or identity) and it’s critical to understand which one is actually driving your unhappiness before you make a big move.
Burnout often reflects a loss of autonomy and misalignment between daily work and personal values, not just long hours or compensation.
Research suggests that if just 20% of your time is spent on the work that most lights you up, your risk of burnout can drop dramatically, even if the other 80% is less enjoyable.
A thoughtful, stepwise approach of clarifying your criteria, forming hypotheses, testing them through conversations, reaching the right decision-makers, and weighing trade-offs can turn a vague urge to quit into a strategic, lower-risk transition.

“You can do anything, but you can’t do everything, and a lot of times we work on climbing to the top of a mountain, and sometimes it is a mountain that someone else has told us would be the right mountain for us to climb. “ — Sherry Mason

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About Sherry Mason: Sherry Mason is the founder and principal coach at Daymark Career Coaching, where she has been advising and guiding professionals through career transitions since 2005. Grounded in an 18-year background in higher education, her experience includes serving as the former Dean of Students at the University of Maine School of Law, as well as a decade working as a Career Coach and Pre-Law Advisor at Bowdoin College and Tufts University. She holds a B.A. in Geology and Geophysics from Yale University and a J.D., summa cum laude, from the University of Maine School of Law, where she graduated first in her class. Sherry brings a deeply multi-disciplinary approach to her practice, holding credentials as an Accredited Financial Counselor alongside specialized training in navigating transitions, public speaking, racial equity, and intergroup dialogue facilitation.

Connect with Sherry Mason:

Website: https://daymarkcareers.com/

LinkedIn: https://www.linkedin.com/in/sherryfm/

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Twitter: @stevefretzin

Instagram: @fretzinsteve

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Website: Fretzin.com

Email: Steve@Fretzin.com

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Call Steve directly at 847-602-6911

Audio production by Turnkey Podcast Productions. You’re the expert. Your podcast will prove it.

FULL TRANSCRIPT

Steve Fretzin [00:00]

Hey everybody, before we get to the show, just want to remind you that the Be That Lawyer community is up and running and rock and rolling. We have a lot of amazing business developer and rainmaking attorneys in there. We’ve got incredible content, courses, live events, and all kinds of ways to help you to be that lawyer. Check it out today at Be That lawyer.com/community And other than that, please enjoy the show.

Narrator [00:29]

You’re listening to Be That Lawyer: Life-Changing Strategies and Resources for Growing a Successful Law Practice. Each episode, your host, author, and lawyer coach Steve Fretzin will take a deeper dive, helping you grow your law practice in less time with greater results. Now, here’s your host, Steve Bretson.

Steve Fretzin [00:51]

Hey everybody, Steve Fretzin, and welcome to Be That Lawyer. I am so thrilled that you’re here. We are now 620 some shows, and we’re all about helping you to be that lawyer, confident, organized in a skilled rainmaker. If you haven’t checked out the Be That Lawyer community, that’s a potential big mistake, because we’ve 85 lawyers in there in just under, I think, six weeks, and they’re all rainmakers, they’re all business developers, they all want to network with you, and we’re all learning together, working together, sharing best practices. What’s your problem? What do you need a new associate? Post it there. It’s this is just very thorough community that’s like, if you had a great Facebook community and this was all business developing attorneys around the country, you would probably want to be there. So check it out at Be That lawyer.com/community see what it’s all about, and that’s all I’ll say about that for now. I’ve got Sherry waiting in the wings. How are you?

Sherry Mason [01:46]

I’m great. I’m so glad to be here. It’s fun, and I’m like starstruck, Steve. I’ve been listening to you in my earbuds for a while.

Steve Fretzin [01:52]

Yeah, people see me in their earbuds just shoot out of their ears because they’re so excited, and that’s how that’s what I see every day when I walk down the street. Yeah, you

Sherry Mason [02:00]

know, everyone would be a star for 15 minutes or in a really narrow niche.

Steve Fretzin [02:05]

Well, listen, I, you know, I have my moments. My teenager’s home from college, and, and he’s just a.. it’s like, you know, I’ve complained. I mean, look, over the last six years of doing this show, I’ve probably complained about my teenager more than anybody, and I love the kid more than life itself. But

Sherry Mason [02:19]

I know how to

Steve Fretzin [02:21]

go.. I grew, he doesn’t listen to the show, so I goof on him behind his back. If someday he does listen, he’s gonna get mad at me. But he comes home, you know, 50 pounds lighter and straight A’s, and like he’s asking, can he help with this, or can he help with them? Like, what have you done with my son? And I’m okay that you left him the other one behind. It’s okay, but life goes on, things change. So happy that you’re here, and I’d like to.. I know we’re going to get into such an incredible conversation today. And, as most people that have been listening to this show know, I love, love, love the quote of the show. So, here’s one.. never been on the show before. This quote is fantastic. So, let’s go through it. Here we go. Between the ages of 20 and 40, we are engaged in the process of discovering who we are, which involves learning the differences between accidental limitations, which is our duty to outgrow, and the necessary limitations of our nature, beyond which we cannot trespass with impunity. And that’s wh odd. And so, Sherry, welcome to the show. And tell us why you love that quote so much. I have a feeling I know, but I think it’s really well written.

Sherry Mason [03:21]

Yeah, I had that quote on my wall for a while. I think that the challenge for really smart people, especially as they are building their careers, is how do you get good at something, and then people come to me, right, which is what is the right thing to get good at, right? So, where you can do anything, but you can’t do everything, and a lot of times we work on climbing to the top of a mountain, and sometimes it is a mountain that someone else has told us would be the right mountain for us to climb, and you know, I’m thinking of an attorney who, you know, spent years climbing to the top of a very hard to climb mountain, and then said, you know, this question of, do you want to stay on that mountain top, or like, is it just cold and lonely on the top of that mountain? Sometimes people are like, wait, I know how to succeed at things, I have a great sense of my own self efficacy, but like, what is the quest I should be on? What is the mission of my life, and that I think there are turning points where we are learning that, but I also think, like, you leave your son, you leave for college, and you suddenly are like, oh, not all families are like my family, not all high schools are like my high school, like,

Steve Fretzin [04:34]

yeah,

Sherry Mason [04:35]

I can choose, what should I choose, right? So that quest that a lot of people are on and attorneys, right, like, get head down, they are like they have the blinders on, they’re the horse that’s running the fastest down the lane, but every so often they get to go, am I running in the right race, like, is this the race I want to devote my energy to?

Steve Fretzin [04:55]

Yeah, well, everybody, you are in for a treat today, we’ve got Sherry Mason, a career coach. Much working with lawyers, and there’s so much to unpack here today, but take us back and give us your story, and how you came to be and working in this amazing industry, doing what you do.

Sherry Mason [05:10]

Sure, you know, I think I’ve been doing this for many years. I went to law school, and I practiced law for a short time. I was a bankruptcy attorney, and I do think that’s the most fun, I there’s a little part of me that would love to be still be a bankruptcy attorney with a tax attorney right next door, that’s the nerdiest part of my brain.

Steve Fretzin [05:30]

Yeah,

Sherry Mason [05:31]

but I remember, you know, I didn’t love the work I was doing, and sometimes I felt like, you know, a trained monkey could be doing the work, and then I would go, well, I’m really highly trained, very verbal, like discerning monkey with a lot of specialized knowledge, and you know, and I asked myself, I’d always thought the thing I could get paid for was being smart, and that the icing on the cake was that I was nice, right, that people liked me, I could connect with others, but I asked myself a question, what if I tried to get paid for being warm, for being nice, for connecting with others, and that being smart was icing on the cake, not the cake itself, and all kinds of helping, coaching, you know, connecting professions sort of opened up, and I felt in my body this sort of like, oh, that’s way more fun, that’s much more my calling. And so I have been in coaching and cultivating and supporting others’ roles within higher, you know, I became an athletic coach, and then I worked in career coaching at a Bowdoin College, a sort of highly selective liberal arts college. I was a pre-law advisor. I helped students go to law school and get highly selective internships and fellowships and White House things. So I got good at helping really talented people figure out where they wanted to go and then get there. And then I, you know, I worked for a national organization called Access Lex, where I taught law school administrators and lawyers who are figuring out, you know, what career to go into, how to pay off their student loans, and still, you know, get the value out of law school.

Steve Fretzin [07:13]

Yeah,

Sherry Mason [07:13]

and I was the dean of students at my own law school for a little while, and then I finally hung out my shingle in 2024 to just work with individuals on their journey.

Steve Fretzin [07:23]

Yeah,

Sherry Mason [07:23]

long story.

Steve Fretzin [07:24]

Yeah, no, I mean, that’s great background, and you know, understanding the law and understanding the lawyer mindset, I think, is really important to how you, you know, think about working with them and helping them through it. And you know, I’m dealing with a lot of lawyers around the world who seem to be, you know, highly ambitious. The question is, is are they ambitious or are they looking for prestige? Are they looking for control? Are they looking for money? Like, there’s all these different motivators. And how do you sort of distinguish between ambition and prestige?

Sherry Mason [07:57]

Oh, I love that question, and I think it is a question that a lot of the lawyers I work with are struggling with, I think that I think there is that between the ages of 20 and 40, quote, I come back to, because I think there are some life stages where you reexamine the game that you’re playing and what you, you know, how to win or how to go to the next level to create the life that is happy for you, so I think that when you are younger, ambition and prestige are often intertwined, because what you are building is a reputation as a smart person with high standards, and you know, a high work ethic, and the ability to deliver quality, right? Those, they are not exclusively found in, you know, highly selective law schools. They’re everywhere, or at, like, big law, but reputationally, if someone sees that on your resume, they stop asking those questions. They’re not asking, like, “Well, is Steve actually smart? Is Steve going to work hard? They believe they know the answers, so you can actually work on having a more sophisticated conversation as you get further along. Those, the question might be, am I building the life I want, and do I need to borrow credibility from the name on my letterhead or from the place I went to school. And then you, you know, and like, why am I playing this game? Am I trying to impress? I was talking to a lawyer who’s thinking about going back to her, you know, law school reunion, and is thinking about, like, what am I going to tell them, and do I care what they think of me.

Steve Fretzin [09:34]

Yeah,

Sherry Mason [09:35]

and you know, my feeling is, if you have a deep conviction that you understand the game you’re playing and why you’re playing it. Other people will hear that conviction and be like, oh, cool, that’s a cool quest that you’re on, and if you don’t, you are sort of relying on, like, I’m impressing someone because of the brand name that’s outside my door, not on the core thing I’m bringing. So, but I think it’s. Challenge,

Steve Fretzin [10:00]

yeah. I’m seeing, I’m seeing people transition faster than in the past. I mean, I’ve been in this space for 20 years, and I think you know the prestige and in the big law name, and that’s going to get you in the door, and all of that. And then there’s so many big law lawyers that went out on their own or transitioned to mid market, where they still use it right. I’m a big law attorney, and now I’m this, and whatever, and I charge lower rate. I tell them not to say that, but you know, as a lead, but ultimately, you know what I’m running into is, you know, the motivation is control, freedom, and independence. You know, that’s if they don’t want to be told what to do every day, they don’t want to have, you know, 12 bosses, right, five internally and seven clients all running their lives right, so when we talk about why their people are in stress and what what lawyers really want, it’s not always money, yeah, right. Sometimes it’s just the autonomy and the knowing that hey, I have a career path where I can control it, versus you know, maybe not really knowing even like how do I elevate or what the comp might be, or what am I even like? Do I bring something in? Is it even going to matter? Like, it’s like a problem.

Sherry Mason [11:06]

Yeah, I mean, I think that feeling of, you know, there is sometimes it is a, you know, in comp alone, you know, this sometimes comp is about like the grocery money and the mortgage payment and the, you know, retirement savings, and you know the goals that you have personally for your family and the kind of life you’re building, sometimes comp is about recognition and feeling valued for your contributions, right? like money is a way of keeping score and of like it is a very practical embodiment that’s different than a like atta boy Steve, right? like that can feel empty if you’re like, well, this doesn’t feel equitable, and so sometimes comp is about respect, right? Or sometimes comp is about control, sort of like I want the ability to decide what happens to this, or to allocate the comp in a way that that rewards effort or proportionality, and so even things like comp that seem straightforward, we put meaning on these things, and that meaning is like how we make decisions, and so I think you can’t, if you don’t know what script you’re running, or what you know, strings you’re pulling, or what assumptions you’re making, you’re going to have this vague feeling of unhappiness or dissatisfaction, but you know there’s the like the resume meeting that I, one of my clients talked about, where you like you have this feeling, this meeting, this interaction that’s so bad, and just you walk back to your office and you’re like, I gotta pull up my resume, I start like rage applying on LinkedIn, but like you’re not necessarily going to get something better or different if you don’t actually know what you want.

Steve Fretzin [12:45]

Yeah, this has to be planned out. I want to get into that, the planning of an exit, but I also want to have you talk through what are the signs that an environment that a lawyer is in is unlikely to change, and that they need to start evaluating the pros and cons of leaving, because if this isn’t going to change, and this is what my life’s going to be, or can I, are there things that I can insert into this to identify that I can change, or I can maybe, you know, better decide my course before making a dramatic exit.

Sherry Mason [13:18]

Yeah, I think there are, you know one of the questions I ask clients right is, is this skills situation right? And I think you know business development is one of those pieces where it’s like I’m just not good at business development, they’re treating it as an identity when in fact like this is a skill, this is a learnable skill that you can intend to get better at, and lawyers know how to get smarter and better and do things right.

Steve Fretzin [13:43]

Yeah, is

Sherry Mason [13:43]

this a situation issue? Right? Is this like, oh, and sometimes situations change if you just wait, and sometimes situations you can kind of negotiate or push back on the situation. You have agency, and sometimes it’s, you know, sometimes a situation, you’re like, I’m looking at the situation, and yeah, I could, you know, try to roll the stone uphill, but it’s never gonna change, and my best plan is to change my situation, or is it an identity issue, where it’s like this is not the kind of person I want to be, like I can’t do this work and be, you know, consistent, there’s a line called Moral Injury, which is, you know, sometimes you see it in criminal justice, where people are like, I sort of no longer believe that my role in the system works, like I got into it to do a thing, and I just kind of can’t believe in that anymore.

Steve Fretzin [14:36]

Yeah,

Sherry Mason [14:36]

and so it’s not, I need to get better at it, and it’s not, you know, I need to change the people I’m doing it with. It’s like this no longer feels like work that’s that I wish to do in my life.

Steve Fretzin [14:48]

Yeah. Hey everybody, your next big client might call it 8pm on a Saturday night. The question is, who’s picking up with Lex reception, a real person, and. Use every call 24 hours a day, seven days a week, so you never miss a lead, no matter when they reach out. No AI agents, no voicemail, just professional legal literate receptionists representing your firm the right way around the clock. And right now, be that lawyer listeners get 250 off their first month. Visit www dot Lex reception.com/partners/be that lawyer to claim your offer, that’s www dot lex reception.com/partners/be that lawyer. Hey everybody, Steve Fretson here. and@lawyer.com they don’t just market law firms, they help them grow from connecting millions of consumers to trusted lawyers to smarter intake and industry leading events. They’re building stronger connections across legal visibility intake events growth. That’s lawyer.com Check them out today with proven SEO and digital marketing strategies that drive actual clients to your firm rankings.io prides itself on proof not promises mentality. The best firms hire rankings.io when they want rankings traffic in cases other law firm marketing agencies can’t deliver. Get more rankings, get cases, and schedule a free consultation@rankings.io today. I mean, I think there’s research that can be done to identify where you may want to go, but I think you should give staying a chance, and something I would recommend is, you know, leverage the relationships you have, or create new relationships to identify, to share your challenges, and to identify the path through, because you might just not realize that you’re just not, you know, leveraging relationships to get where you need to go within a certain system, and you’re just trying to bump your head into it to figure out, like, hey, what can I put my head through that’s going to be, you know, softer than a brick. And so, understanding identifying calm, understanding identifying way a ways out, you’re being fed work by people you can’t stand or work that you don’t enjoy. How do I stop that, and how do I get into a different practice area? How do I leverage it, so you can actually make your own change before you actually leave to go somewhere else? If you take some steps, so can maybe..

Sherry Mason [17:15]

Oh my gosh, yeah, this is such a rich vein, and it’s really interesting. People come to a career coach when they’re like, I gotta leave, right? And sometimes they’ve waited so long to come to me that they like, they are taking the action, and they feel like, yeah, I’m finally doing something about it. I talked to them the next week or two weeks, and they’re like, yeah, I quit my job. Well, okay, now you’ve really created some urgency here. So, okay,

Steve Fretzin [17:40]

wow,

Sherry Mason [17:41]

but you know that feeling of powerlessness. You know, I do think when you take a step and start saying I am making a plan, that can just give you that sense of autonomy that you’ve been feeling is lost. But you know, so people come to me when they’re unhappy, and I do think this question, Should I quit my job? You always have four choices, right? There’s wait it out, which is like, you know, is it going to be different in six months? Are you going to be different? Is this is the matter that you’re on that’s, you know, going to be different? Can you get, you know, you can tune it out, which is the mindset, like, how does this not bother me? Like, what do I work on with myself? And I think that piece in a high demand, rigorous, right? Like high productivity, responsive, you know, environment is, you know, how do you let that not bother you? Because you may jump into another situation that you know it’s different humans, but some of the same expectations. You can work it out, which I think is what you’re talking about, which is you’re going to negotiate with the people around you to get more to nudge it to be more like what you want, and then you’re going to get out, right? Like, so those are the four options, and each of those have some complexity. I want to tell you about this research that the Mayo Clinic did, and the Mayo Clinic, it’s about physicians, right? And physicians are different than lawyers, but physicians have some similarities, I think. They’re, you know, it’s highly regulated, highly educated, you know, these are not people with time to waste, and it’s about burnout and job satisfaction. And the Mayo Clinic was like, it’s kind of like what you were saying about the associate problem, like this is a problem for our industry, this is a problem for healthcare, this is a public health problem. If physicians are all exiting, so why are they exiting, and what? And there are a whole bunch of reasons, and some of those reasons are under individual control, but physicians, like lawyers, get really exasperated if you tell them you need to do yoga or you need to do a mindfulness app, like some of it is about your firm and its structure, and some of it is about you and the decisions you make, and some of it is about the industry and the client expectations, right. So physicians have the same kind of constraints, but this study said if physicians, you know, spend 20% of. Their working time doing the things that are most aligned with what brought them into the work in the first place, that they love the most. Their burnout numbers went way, way, way, way, way down. And it was not the case that it was like 20% is good and 50% is better. It was like 20% you hit 20% you did it. So that means 80% of their work can be stuff that there’s like a headache they don’t really love, like it’s a drag, we all use, why they pay me, right? If 20% is that like that stuff that lights you up, so the thing that, so like that’s really promising, but the other thing the Mayo Clinic said is that physicians need to know what that 20% is, and most of them didn’t, like they couldn’t articulate the parts of the job that they loved.

Steve Fretzin [20:47]

Yeah,

Sherry Mason [20:47]

and their practice group needed to ask, right? And I think that that applies a lot to lawyers, or like, where is the part that lights you up? How do you just structure your work so 20% 80% can be, you know, not that great,

Steve Fretzin [21:02]

yeah,

Sherry Mason [21:02]

but if you get your 20% that’s a huge win, but you have to know, and your, you know, your partners or your practice group has to ask, and neither of that is that hard, but a lot of people are so down, I don’t do

Steve Fretzin [21:16]

it, yeah, I don’t know that that’s happening in any kind of level, but I mean, look, you’re spot on in the sense that you know, look, you’ve got to find your happy place, and if you’re doing other people’s work with clients you don’t care for, if you’re bringing, doing work that you’re, that doesn’t bring you joy, it’s not the area of focus that you, that you want to work in, and you’re dealing with internal politicking, and he said, and she said, and feeling you know, lesser than all of these things are going to add up to dissatisfaction, and it’s up to the firm to sort of help you through it, and it’s also up to you to recognize, is this something that is fixable, and is this something that is not, and you know, burnout with lawyers is, is a major, a major issue, nobody’s going to argue that point, and so, whether it’s business development, finding the area that you want to focus on, finding a better home on your own, or with another firm, you have a lot of options. You just got to make sure, and I think this is your lead in again, is you just have to make sure that when you decide that you’re going to make a change, that you don’t just quit, and then you got to wonder, like, all right. What do I do next? I think this needs to be thought out three six months ahead, and it’s like my dad always told me, don’t ever quit a job until you have another one lined up. I mean, Larry, the lawyer, the late great, you know, lawyer from Be That Lawyer fame, you know, that’s just another piece of wisdom that he gave me as a kid, and I, and I never did that, I never quit a job until I had something lined up, because that really stuck with me. So, maybe take as our kind of maybe one of our final topics today. Let’s unravel that a bit. How do you prepare to exit, and what are the best strategies

Sherry Mason [22:53]

to do it? Yeah, I mean, I think that lawyers are risk-averse, lawyers are planners, right? So, I don’t see a lot of lawyers acting impulsively in this matter, but I do see lawyers sort of overthinking, right? They’re like, I can’t do anything until I know exactly what I need, and so they’ll, they’ll, you know, or they’ll sequentially be like, well, what else could I do, and they’ll think about a thing, and then they’ll be like, well, I don’t, should I do that thing, I don’t know, how, I don’t, you know, like that would be hard, maybe it wouldn’t work, and like, it’s risky, and so for a lot of people it’s like you have an idea, then you bring your lawyer brain, and you sequentially like analyze it to death, about like, okay, now you know everything that’s wrong with that idea, like, better not do that idea, I need a new idea, and you go around in that loop, and you can stay there for a really long time, yeah, I think there’s a better way to sequence those inquiries where you don’t have to stay paralyzed, and you know, I think, like any lawyer knows, you can take a very big complex matter and break it into steps, each step makes the next step easier, and you know, I do think I bring a lawyer’s brain to the dread and overwhelm of, like, what do I even like, what do I want, how do I figure it out, what if this is the only thing I can do. You know, there’s a lot of it, just breaks my heart to see smart people like trapped in a cage that they’re just making up, and so, you know, so I think of it in five steps, and my little way of remembering it is the word chart, right? C is for criteria. You can’t get what you want till you can name what you want, and that includes, like, what are the activities, what are you working on most of the time, what’s the culture of the firm, right? Are you here hearing your heels click in the marble foyer while you go up swooshing up the elevator, or are you, you know, bringing your dog to work, and what is the purpose? What’s the big why, right? What’s the sort of like, even on a bad day, like I’m moving closer to this thing that that matters to my family, or to me personally. The H is a hypothesis, right? Like, oh, I think I could get my what I want at these kind of places, I’m not sure, but like I’m pretty sure. Like I have a this could work, and then the A is where you’re analyzing and assessing and adjusting your hypothesis, you’re gathering data, and that’s mostly networking, it’s conversational research. Looks like in house would be really good. I want to talk to some people in house and see what assumptions probably 80% of your assumptions are right, but 20% of them are unfounded, and like you’re going to be a lot smarter after you’ve had some of these conversations, and there is reputational risk. A lot of people are afraid to do that, because they don’t want to be like, well, I don’t want to look like a hot mess when I talk to Steve and reveal that I don’t know that much. So a lot of the work I do is about sequencing and coaching those conversations, so that you are impressive without needing to be decided, you know, you can be in a really impressive discovery conversation rather than a persuasion conversation, so you’ve got Cha now, the R is to reach the right person with the right message. Right, this is who’s the decision maker. What do they care about, and how do you show them that you’re the person who can solve their problems? And then the T is the trade-offs, right? You get the offer, you negotiate the offer, and you’re kind of like, all right, this is, is this perfect? Like, how does this relate to what I wanted. Am I going to hold out for something better, or I’m going to get to take it and be excited about it.

Sherry Mason [26:25]

And so I help people with all of those, but I find that my lawyers, the high achievers, the smart people that I work with, when you have done the C and the H and the A, the R and the T take care of themselves, right? Like it, like you’re not going to start with your resume until you know who’s reading it and what they care about, and probably relationships are going to be the more persuasive thing. And the resume is just something that shows up eventually, and HR has to put it in a folder somewhere.

Steve Fretzin [26:55]

Yeah, I’d much rather find a job through a relationship and one where they can give me the inside scoop, and I can really understand the culture, the comp, everything, because they, they’re just going to tell me what’s going on, versus, you know, resume, you know, dump, yeah, even working with a recruiter, I think a recruiter is a great thing, and it’s free for, you know, lawyers, however, you know, they’re plugging you into cultures and places that maybe you’re not able to find out as much about ahead of joining than if you have a relationship or two or people that can get you in with relationships, so really, really great stuff, Sherry. Of course, we have to ask, what’s Sherry’s big mistake?

Sherry Mason [27:36]

There are so many, Steve. I think there are a couple I want to say, and one is it’s not a mistake, but it was shortsighted, and I learned so much from it. So I want to, I want to give it as advice. I was way back when I was a baby lawyer, and I had two firms. Neither of them were quite making me offers, but we’ve been going through the interview process, and I was just like, oh, it felt like pushing string uphill, like I couldn’t, couldn’t get the offer to come on my timeline, but I, I also realized I didn’t know enough to choose between them, and so I, what I did this thing that you know seems genius in retrospect, but it was just sort of accidental, I reached, I was like, I want to talk to experienced lawyers who know more than me about these two firms, and who don’t work at them, so will speak the truth to me, like what you were saying, you need the gossip, right, especially when you’re like you can’t quite see inside, you need people to tell you the truth. So I reached out to this lawyer, and I was like, listen, I’m interviewing these two firms, I’m just early in my career, you’ve been at this for a long time. You like, what do I not even know to ask that I should be asking? And how would you think about this, right, if you were me? And so he answered my question. He was like, what, this is very interesting. Why are you, you know, but he was, he had not been asked that before, and he was happy to talk to me. But then he left at the end of the conversation, he was like, “Can I talk to someone else about you? And I was like, “Sure. And, like, he told his friend, who was looking for an associate who hadn’t posted anywhere, and suddenly I was interviewing for a position that I didn’t have any competition with.

Steve Fretzin [29:17]

Yeah,

Sherry Mason [29:18]

because this guy had thought I was asking good questions,

Steve Fretzin [29:21]

yeah,

Sherry Mason [29:21]

and it, I, to me, it reveals this thing that I think it’s like we know in our hearts, but when we get stupid and go on LinkedIn, we just think the only jobs are the jobs that are posted,

Steve Fretzin [29:33]

yeah,

Sherry Mason [29:33]

when in fact all the jobs are gossip before they ever get posted, and by the time they’re posted, they’re too late,

Steve Fretzin [29:39]

yeah, it’s something going on in real estate, where homes are being sold ahead of them being listed, right? So, I think I’m.. I feel like that seems like what’s going on. It’s like, how did that happen? It was.. it was.. I was.. I saw it like a sign up, and then it was gone, and it was like, you know. So, I think finding that that hidden treasure is really brilliant, and again, this is why.. I were talking about on the show all the time, relationships, relationships, relationships. This is where business development happens. This is where careers can be changed. This is what gets us out of, you know, the resume. I think you call it like anger resume, would you call it a rage applying rage, resume rage or something. Well, really fantastic, Sherry. Everything shared today, really brilliant. And I’m just so happy that you’re here. Let’s take, of course, a moment and thank our wonderful sponsors, Lex Reception. Don’t answer your phone, give me a break. Come on, there’s people that can answer it professionally. Make sure that you get the appointments, and in day or night, you need to have that phone answered. lawyer.com great directory, and of course, Pym Con coming up in October, the number one personal injury mastermind event of the year. Sherry, people want to know how to get in touch with you, they want to work with you, they want to figure out, like, you know, their career. What are the best digits for them to find you?

Sherry Mason [30:56]

Yeah, my business is called Daymark Career Coaching, and that’s where to find me, Daymark careers.com What a pleasure to talk to you.

Steve Fretzin [31:07]

Yeah, yeah. Oh, it’s so great, and I just appreciate, you know, all this wisdom for lawyers, especially. This is like this is like the time where people need to start really thinking about their career. I mean, that is, there’s always every time you should be thinking about their career, but like there’s going to be a lot of change and disruption in the marketplace in the next couple years, whether people believe it or not, that’s that’s on them. Yeah, so I think thinking about your career, how AI is going to affect it, how you know your firm is going to be looking at it forward or backward, all these things, the culture you’re in, going out on your own, like there’s so many choices and options, and so I think now is the right time to start thinking about if you haven’t.

Sherry Mason [31:44]

Yeah, and I think that that piece, that you know, for lawyers, the path to becoming a lawyer is really structured and really clear, right? You have to get the grades, you have to take the test, you know, it, you have to, you know, often it’s OCI at your law school, right? It is really there are no, you know, there are pretty clear milestones and pretty clear metrics to know if you’re doing well or poorly.

Steve Fretzin [32:11]

Yeah,

Sherry Mason [32:11]

but then in your career it gets a lot fuzzier, and the question of how to even decide what practice area or what firm to join, like suddenly all of those clear metrics go away, and I think that that makes lawyers feel like, wait, I don’t even know how to play this game.

Steve Fretzin [32:29]

Yeah,

Sherry Mason [32:29]

it’s not a hard game to play. You just need to know the rules, and you need to sequence the questions in the right order.

Steve Fretzin [32:35]

Well, some would say knowledge is power, right? So that’s what, yeah, what we do.

Sherry Mason [32:38]

Yeah. Well, thank

Steve Fretzin [32:40]

you so much for being on the show. Really amazing, so appreciate it. And you know, I’m looking forward to, you know, putting this out on the, I know, on all the media channels, and then just helping more lawyers figure out their careers, helping them to be that lawyer, confident, organized, and a skilled rainmaker. Take care, everybody. Thank you so much for hanging out with us today. Be safe and well. We’ll talk again so very soon. Bye. Thanks

Narrator [33:05]

for listening to Be That Lawyer, life-changing strategies and resources for growing a successful law practice. Visit Steve’s website, fretzin.com for additional information and to stay up to date on the latest legal business development and marketing trends. For more information and important links about today’s episode, check out today’s show notes.

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