The Cost Of Career Coaching For Lawyers with Annie Little [TFLP 110]

Annie Little is an ICF-certified career coach and a former lawyer. Her company is called JD Nation, which was founded in 2012. In 2013, Annie left her position in real estate finance. Since then, she’s been offering career coaching for lawyers, helping former lawyers land and succeed in their ideal jobs.

On the latest episode of the Former Lawyer Podcast, I was joined by Annie Little to talk about a topic that isn’t covered enough. The topic is what you can expect to pay when you’re looking for career coaching as a lawyer.

In this article, I’ll be reviewing what we discussed about the pros and cons of one-on-one career coaching and working in a group. We’ll also be sharing our own experiences in career coaching for lawyers and what we’ve observed.

One-On-One Coaching Versus Group Career Coaching for Lawyers

There are two ways that you can get coaching, either one-on-one or in a coaching program. Let’s look more at one-on-one coaching for lawyers vs coaching programs for lawyers.

One-On-One Coaching For Lawyers:

If you’re looking for one-on-one coaching, you should expect a series of at least six sessions with a career coach for lawyers like Annie. Each session may cost you $500.

One-on-one isn’t a pure hourly model, but it’s close. It’s very similar to a lawyer’s hourly rate model. It’s very tailored and unique to your needs. But it’s also very expensive and isn’t a fast-track kind of program. It might take up to a year of sessions for you to get a specific outcome.

Career Coaching Programs For Lawyers:

Having a process for coaching lawyers in groups can be much more efficient, and more affordable as well. When a coach has a framework that people have gone through it and has people in the coaching program at the same time as you, there are so many intangibles that you don’t get from one-on-one coaching. 

One of the biggest benefits of coaching programs is the fact that you are having this experience with other lawyers who really understand what it is like. Anne shared one thing she talks a lot about in her group calls was sharing wins and rediscovering what a win really is. Someone who may think they’ve lost will be supported by the group who sees things as a win.

What Factors Into The Cost of A Coach’s Expertise?

Part of the reason career coaching for lawyers costs so much is because of the baked-in value of a coach’s expertise. You really do get what you pay for in career coaching for lawyers. 

It’s not like becoming a lawyer; going to law school and just getting the title without any practical work. You have to coach to get certified, you have to have a specific amount of time coaching to even qualify.

Experience in Career Coaching For Lawyers

A career coach that’s relatively new to the field may charge around $50 for a session and a follow-up, but your results will vary wildly. If they haven’t been in it a long time, they likely don’t have a framework process or experience. 

It could go over great, but the results are going to vary a lot more in terms of time and efficacy. A coach who has more experience and a little bit more training, and just has more of a process, they’re going to charge more. 

Of course, this depends on the results you want and the timeframe in which you want to achieve those results. That’s where you’re going to see the dollar amount climb towards the thousands.

Baked-In Costs:

How much of your billable rate ends up going into your bank account? The rule of thumb is usually about a third of your net income. If you’re talking to a one-on-one coach and they give you their fee and you’re thinking, “$500? That’s bananas!” Just remember, the coach isn’t putting the full $500 in their bank account. They’re paying for their overhead.

You’re paying someone for their expertise, not just time spent with you. Think about someone who’s hiring you to do their legal work is paying for your law degree, what it took for you to pass the bar, and all of your continuing legal education. It’s all just baked in.

The Cost Of Desired Results

You want to be mindful of what the promised results are for a coaching program. Can this coaching program do what it promises? Does the coach have the knowledge or expertise to provide those results?

Lawyers have some unique obstacles when it comes to making a change in our career or just wanting to level up in our career. Regardless of who you’re working with, you are going to get better results from someone who understands your industry and the experience that you’re having. 

Finding The Right Career Coach For You

Finding the right career coach is a process. Part of that process is just getting a feel for that person because, in addition to the answer to your question, you’re going to get to know this person a little more during your first few calls. If they have a podcast or a YouTube channel and just their website and their social media, you already have a sense of what this coach is like.

But when you’re interacting with them on your issue, whether it’s over email or phone, or video call, you can get a sense of whether or not that coach is going to be the right fit for you. And it’s the same for the coach. You may not be the right fit for them. And, if you’re not a good fit for each other, that’s okay. You can go find someone else because we’re not a fit for everyone.

Whether you’re planning on working with a coach one-on-one or joining a career coaching program, remember to see beyond the cost. Look into expertise, the framework, and the promised results to find out if this program or coach is right for you or not.

And, if you’re not quite to the point where you need a coach, and you’re just thinking about leaving the law, I invite you to download my free guide: First Steps To Leaving The Law or join Annie’s program Make Your Next Move.

 Connect With Annie:





Mentioned In This Article:

Annie’s Program: Make Your Next Move:

First Steps to Leaving the Law:

Sarah Cottrell: Hi, and welcome to The Former Lawyer Podcast. I'm your host, Sarah Cottrell. On this show, I interview former lawyers to hear their inspiring stories about how they left law behind to find careers and lives that they love. Let's get right to the show.

Hello everyone. This week on the podcast, I invited Annie Little back to talk about a topic that I think is not talked about enough and there simply isn't enough information out there, which is what can you expect to pay when you are looking for career coaching as a lawyer, whether you want to work with someone one-on-one or in a group and also what is it like, and what are the pros and cons of working with someone one-on-one versus working in a group. Annie has been coaching lawyers for nine years, so she has been a part of this industry for quite a long time and has seen a lot. We both each have group programs and she's also done a lot of one-on-one coaching. I've done a bit of one-on-one coaching, so we share a lot from our own experience but also the things that we've observed and heard from other people. I hope that this will be helpful for you as you're thinking about whether or not you may want to invest in career coaching. Of course, if you have any questions after listening to us, feel free to find us on all of the socials or shoot me an email at [email protected] I would love to hear from you. Let's get into this conversation with Annie Little.

Hello, Annie Little, welcome back to The Former Lawyer Podcast.

Annie Little: Sarah, hi. Thanks for having me back again.

Sarah Cottrell: I am so excited. We are going to talk about something today that I think is something that many lawyers have questions about. But first of all, can you just introduce yourself for the listeners, for anyone who has listened to one of your two prior episodes?

Annie Little: Sure. I'm Annie Little. I am an ICF certified career coach and a former lawyer. My company is JD Nation, which I founded in 2012. In 2013, I left my practice area, which was real estate finance at a boutique firm in the Philly suburbs. Ever since then, I've been coaching exclusively lawyers to help them land, lead, and succeed in their ideal jobs and never looked back.

Sarah Cottrell: I love it. I love it. I asked Annie to come on the podcast to talk about something that is a little bit of a black box for people and that is the cost around career coaching for lawyers because it's just been my observation now, running Former Lawyer for just two years, that there is a lack of information and people don't really know what to expect or even what they're looking for. Of course, Annie mentioned she started her company in 2012, so she has vast amounts of experience much more than me in this industry, so I thought she would be a great person to come on and talk about this. The other thing is she has done one-on-one coaching. She also has a program called Make Your Next Move, which we'll put the link to in the show notes for this episode. We want to talk about pricing and the cost of career coaching for lawyers. Annie, do you have any initial thoughts that you think people should hear before we jump into the specifics?

Annie Little: I just want to reflect what you said. Black box, that resonates so much. I think it's because there's a black box around so much in the legal industry. Part of what's going on here with the coaching industry and how it can be a black box because it's on the newer side, I feel like lawyers accept that it's a black box. They're just trying to find, “Do I find someone cheaper or someone better? What does that even mean?” I love that you have identified this as an issue because the black box is not okay in the legal industry around salary, promotions, and all that. Let's bust it wide open here for the coaching stuff.

Sarah Cottrell: I like it. I like it. To start, let's just give people a sense of ranges. If someone is thinking, “I need one-on-one career coaching.” Either, “I'm a lawyer who's wanting to leave the law” or just, “I'm a lawyer who's wanting to find another position.” What can people expect in terms of pricing, packages, all those sorts of things?

Annie Little: Great question. If someone's looking to switch practice areas or figure out what they want to do or something, because I'm helping lawyers find other lawyer jobs or something else, and yours are like want to find something other than law, so that kind of thing, if you're looking for one-on-one coaching for that, that is not going to look like a one-off session. That's probably not going to look like a two-off session. That is something that I found over these nine years of coaching that a group program is your best bet there because with one-on-one coaching, the best that I could do once I had honed my process and I was working with attorneys through the process that I use in my group program now, it was a minimum of six one-on-one sessions over the course of three months, sometimes, stretched out longer because lawyers get busy but that was the most condensed period in terms of number of sessions because there's the part about figuring out what you want to do, making sure the stuff you want to go into is what you really want to go into. Some of us just really don't have any idea, so that can take a couple sessions in one-on-one, depending on how much work you're doing on your own and if you're getting stuck in the meantime, then there's finding where the jobs are and not just job posting, then there's the networking part of it, then there's staying on track and not getting sucked into the complacency outrage cycle. You're like, “I hate my job,” so you start applying, then you're like, “Oh.”

Sarah Cottrell: You’re like, “Oh, maybe it's not that bad.” “Oh, maybe it’s terrible but I'm too busy to actually do anything about it.”

Annie Little: Exactly.

Sarah Cottrell: Exactly. The endless cycle.

Annie Little: Exactly. Then there's that element, then once you do find stuff you want to apply to, sometimes, there's this panic of, “Oh my God, I haven't used a resume in a long time. Let's revamp my resume.” That's a whole other thing, the cover letter, then apply, then there's the waiting after you've applied, which enters the outrage complacency cycle again. Then there's the interview cycle, then there's the negotiation process after that too. Just describing that, you can see, even if things move in a pretty lock step fashion, it can get pretty protracted.

One-on-one, it's not a pure hourly model but it's close. It's very similar to a lawyer's hourly rate model. Maybe part of why it's important that we're talking about this, Sarah, is that there isn't group legal services. There are places where you can go for as a resource to get legal services but you're not sitting in a group and getting a lawyer talking to a group about their their legal problems because the assumption is that everyone has very unique separate, and private legal problems whereas in coaching, that's not always necessarily the case, especially when there's a process. When there's a process or a framework, a common problem that people have, what I have found for my coaching practice and what I have seen in so many other coaching practices with other coaches in all kinds of different niches is that having that process in a group format, and laid out in a curriculum or framework is much more efficient and much more affordable. That's something that I know we're going to talk about today because the one-on-one feels very special, very tailored, and very unique but it is also very expensive, both in time and in money.

Sarah Cottrell: It's interesting. Part of why I created my program the way I did was because I wanted it to be as affordable as possible for as many people as possible. But I have found that it seems to me there is sometimes a misperception. Some people, some lawyers, I think have this, I mean the price of my program, it's available. You can see it's currently $1496 or there's a payment plan. I've found that there are people who look at that price and think, “Wow, that's a lot,” and have expressed to me that they think that if they found someone to work with one-on-one, that they could do so for less.

To me, that has been a real example of this black box idea because for me, I'm putting together the program. My goal is to make it as affordable as possible because, I think you would agree with this, you're really not going to be able to find quality one-on-one career coaching for even necessarily the same amount. Certainly not for the same amount of time but there is somehow this perception with some people that you could find that. You've been in this industry for many years, so tell us what you think about that.

Annie Little: This is the TLDR, just in case you don't want to hear my whole spiel, you really do get what you pay for in coaching. That is not meant to be a dig. Here's why I think it's important to get into this. It's because unlike when you're a lawyer, we go to law school, then boom, we're lawyers. You don't have to do any practical work as a lawyer to call yourself a lawyer and to be a lawyer. You learn on the job. If you want a certified coach, you can't become an ICF certified coach without coaching. You have to coach in order to get certified. That is why you will find coaches, at the very beginning of their training, charging not very much. When I started my first certification courses, I was still practicing law—so it was a side thing—I was doing nights and weekends, and I was charging my friends from law school $50 per session, then that included prep work. I would send them a packet to fill out ahead of time, then we would follow up via email and accountability stuff—$50 for all of that. But that's because I was new.

For me, it was something I actually wanted to do. That's part of my process for helping people figure out what they want to do. You got to try it. You gotta actually see what it feels like. Then as you coach, you become better. As you take more certifications, you get better. It's possible you could find someone like me who was charging $50 for a session or you'll even find some people who are giving away sessions. There is absolutely nothing wrong with that. I love when people do that. I give stuff away for free too but if somebody is making it a practice of offering a whole free hour session, it's usually because they're at the beginning of their coaching journey, let's call it. There's nothing wrong with that but if you are going to find someone who's a one-on-one coach and they're offering you a session for let's say, $100 or less, they are new. They are new. They will be lovely but your results will vary wildly because if they haven't been in it a long time, they likely don't have a framework process, experience, all that good stuff.

They can still be helpful for sure but comparing someone like that to the Former Lawyer Collaborative, it's night and day, apples to oranges, it's not even close because it's like, “Okay, even if I have this person that charges $100 per session, I could have 15 sessions with them rather than do Sarah's program.” You could. Do you want to? Do you really want 15 sessions and there's no real guarantee of what you're going to get? Of course, we can't guarantee anything in your program, I know that. But you have a system, you have a framework, you've had people that have gone through it, you have people who are in the program at the same time, so people can support each other, hear each other, and get all these intangibles that you don't get in one-on-one coaching. That's where the starter is and where people might think, “Oh, I could get one-on-one cheaper.” Because you might have seen people advertising for that kind of stuff. Those people tend to be early in their coaching careers and early in their business. Then you'll scale up to the other end of the spectrum and that's where you're going to get the real pricey but go ahead, I think you're going to say something.

Sarah Cottrell: I was just going to say just for people who are listening who are like, “Okay, Sarah, but I want some hard numbers,” I do very limited one-on-one work. If I work with someone one-on-one, it's someone who's already in the Collaborative. I have done a little bit of that but it is not a big part of my business model at least at this point. If someone comes to me, emails me, whatever, and they're looking for one-on-one, I have a list of people who I will recommend that they go to. I'm just going to say that the people who I am referring out, and these aren't affiliate relationships, it's purely me wanting to help people who the Collab isn't a good fit for but who are looking for one-on-one, there is no one that I would refer you to who I actually think is going to be helpful and get you the results that you're looking for, who you're going to be paying less than like minimum $2000. That's just minimum, minimum for one-on-one in terms of people who I feel can get people the results, basically, who I am willing to recommend.

Different packages work in different ways but that is just in my view. In terms of your expectation, if you're looking for one-on-one support, that is the minimum that you need to be prepared to spend. The only exception is if you are looking for a very specific, very limited thing. Let's say you have a specific interview and you want to do some specific interview prep, you may be able to find someone who does a one-off session where you're specifically prepping for that specific thing but even then, you're coming to them with lots of information like, “It's this job, it's this way, blah-blah-blah.” Or if you're specifically looking for an answer to, again, a very specific question, not like, “What should I do next?” you may be able to find someone who can do a one-off session with you where it will be helpful. But even then, I think that you should expect to be looking in the $500 to $1000 range.

Annie Little: 100%, because that's how I was doing stuff until recently because I have my group program and it makes so much more sense for my clients to have this framework laid out in modules. I can say, “Start here, then once you've completed module one, let me know what you need. I can point you towards all the other resources and you can have all those resources at your fingertips 24/7. Then if you need me, send me an email. We have other mechanisms in the program where you can reach out for help and get feedback from me. We have calls, all the stuff.” Whereas with one-on-one, I don't give people access to my whole program. You don't get all my entire framework. You have to pay for that separately.

I might send people a worksheet here and there but like you said, that's exactly how it would work. I would have people apply. I make people fill out applications for my one-on-one coaching no matter when I'm offering it or for what purpose. It would have to be for a very specific purpose. The lowest price that it would come in at is $500 for a session with a little bit of follow-up. Like you said, the interview stuff, that's really, really common but because interviews go multiple rounds, I'll often get people who do more than one session, so boom, you're at $1000 right there.

Sarah Cottrell: I just want to say for people who are listening, we're talking about our own stuff because we know our own stuff and can be more like I'm willing to disclose etc., but part of why I had Annie come on is because she has been in this industry for nine years. These things that we're talking about, we are not like special exceptions or the things we have observed are not special exceptions. Annie, I think you would agree, this is the landscape, this is the lay of the land.

Annie Little: Oh, for sure. Another thing, just for reference, we are in this little tiny niche. We help lawyers with their career stuff. That's very, very specific. Yes, there's a whole cottage industry around that but because it is so small, we all know each other and I am hard-pressed to find someone who offers the same type of thing for price points lower than what we do. I honestly can't think of anybody. At this point, my program is a year and it's $2500 but I run promos, like limited time offers throughout the year, so you can get it for $2000. You just get tons of stuff from it. With the exception of the Collab, which comes in just under that, I cannot think of another resource that's cheaper. I can think of resources that are shorter in time and about twice as much as what we offer, if not more, for lawyers. But if you look in the online business community, like how you and I, how we learn how to do things in our business, I'm always in group coaching programs and I rarely do one-on-one because I don't see as much value there, but do we want to talk about how much we pay in broader industry?

I don't even know if I want to go there but it's just to say, to your point, we're not outliers by any stretch of the imagination. If anything I find that you and I, our services are on the lower end of things, whereas I joined a group program last year for my business and it was $10,000. I paid for it and it was worth it. It was 1000% worth it. Just for a frame of reference, and I don't know maybe another way to think of it is in terms of legal services. Think about if a client is looking for help, are they going to go to a big law firm for it? Are they going to go to a boutique firm for it or are they going to go to just a general practitioner? Think about the range of costs involved there.

You can think about that similarly with coaches. You can find someone who is perhaps a more general career coach and they're newer, they may not have any certifications and so they're going to be much more affordable. They'll be able to help you, they're not going to hurt you, but the results that you want are going to vary a lot more in terms of time and efficacy. Whereas you move up into somebody who’s got more experience and a little bit more training and just has more of a process, they're going to charge more and so on. Depending on the results you want and the time in which you want to achieve those results, that's where you're going to see the dollar amount climb.

Sarah Cottrell: Yeah. I think people can definitely get benefit from a more general career-coaching program if they're a lawyer but just anecdotally, I have many of the people who are in the Collab previously did some either worked with a career coach one-on-one who is not a lawyer, didn't have experience in the legal profession or some program that was more for people in all different types of careers and repeatedly, I will hear, “Yeah, it was helpful to a point,” but they didn't really understand the specific things that I was dealing with and the unique challenges that I was facing and so a lot of the advice was not completely on point, etc.

Not that you can completely get a sense of this on the front end if you're considering either working with a coach or joining some program but I do think that you want to be mindful of what is the program promise, that's the thing that people talk about in the online business industry often. What are they telling you they can do and do they actually have the knowledge or the expertise that they need in order to provide that result to you? This comes up on the podcast all the time. Lawyers, we have some very unique obstacles when it comes to either making a change in our career or just wanting to level up in our career. Again, this isn't even to be promo for Sarah and/or Annie, this is just all lawyers, regardless of who you're working with, in most cases, you probably are going to get better results from someone who actually understands your industry and the experience that you're having.

Annie Little: Think about it in terms of recruiters, would you use a general recruiter to get another lawyer job? No, you'd use a legal recruiter because they understand the difference and what your resume needs to look like. Because some of the general career advice, like you said, it's not that it can be completely opposite and hurtful to your legal career.

Sarah Cottrell: Yeah. Also the other thing I wanted to say is number one, yes, every business coach I have is always like, “You should raise your prices. You should raise your prices.” That's my own thing. But also, I recognize that $1500, objectively, that is a lot of money. I'm not trying to say, “Hey, if you want career coaching, you should be able to just pay $1500 or $2000 or $2500, or whatever, for a program and that shouldn't be a big deal.” It is a lot of money, it is an investment. I don't want it to come across as though we're saying, “This is the amount that people pay and you should just get over it,” or whatever, that is not the message I want to communicate. But what I do want to communicate is that I want people to be able to have a realistic expectation in terms of if they're wanting this kind of help, what they would be looking at. Does that make sense?

Annie Little: Oh. Absolutely, because I feel the same way where I'm like, “All right, it's $2000. I've got payment plans. I've got all this great stuff,” and you're going to get so much value but it's like, “Hey, I get it, it's a big investment.” But that's also something that I find helps people, helps lawyers really think about “Why do I think I want to work with a coach? Why do I think I need a program? Is it because I've tried and I don't know what to do next? Or I've tried and I can't stay on track? Or I don't even know what I want to do?” When people are applying to programs or talking to me about coaching, the money thing really helps them to bring into sharper focus what they're looking for and what they really need. Because sometimes, it's just a different issue and it's something where they should probably just go to therapy instead. I can't tell you the number of times, especially many years ago, I would do one-on-one consults and I'd say, “Hey, if this makes you uncomfortable, please tell me and I'll shut up, but have you ever been to therapy?” Most people would be like, “Yeah, yeah, yeah.” I'd be like, “Okay, well, that might be a better place to start for the issues that you're coming to me with.”

Sarah Cottrell: All the time, I'm like, “Hey, I would love to have you in this program but for someone in your position, what I recommend is that you find a therapist and work with them on some of these things.” I also will tell people, “Listen, if you have to choose between my program and therapy, please choose therapy.”

Annie Little: At least your insurance might help with that.

Sarah Cottrell: Yes, all day every day, because that is something that is going to be extremely important regardless of where you end up or what you end up doing. In fact, I was just talking to someone in the Collab this week about the fact that they were telling me that they've done other work related to their career but it was all various free things like books and whatnot, and they were telling me that they have had so much more success being part of this program, which is paid, because for them, it was like, “I'm making an investment in myself and therefore I'm getting better results.”

Annie Little: Oh, yeah. When I referenced that $10,000 program I did last year, a big reason why I picked that program is because I knew it was the best for what I wanted to do in my business that year and I knew if I spent $10,000, that in and of itself was going to motivate me to stay on task because I understand how I'm motivated, and a lot of us are. We've paid how much to go to law school? That's a huge investment so we understand, at least, on some level what it's like to spend a lot of money to further our careers and to better ourselves. I say that as a way to not be like, “Oh, you need to spend money to do what you need to do,” but if that's something that you know motivates you, there's no shame in that. That can actually be a feature, like what we've been saying, of investing in yourself. It's like having skin in the game because when we do have free resources, it's like take it or leave it, or when I feel like it, or is this really that helpful? If it's so helpful, why is it free?

Our minds can play these funny little tricks on us too, whereas if you plop down some money you're like, “Okay, this is the real deal. I'm going to do it this time.” If you're going to do that, I really encourage people to ask questions before you get involved. If there's anything that you have a question about, ask the person who's leading the program. Of course, if you're doing one-on-one, you'll be talking to the coach individually, but ask all that stuff up front, like what are your biggest, I don't want to say fears, but what are your biggest concerns or hang-ups or what have you struggled with in the past? If you're dealing with a coach who is in integrity, they're not going to use that against you because I find that, at least, many years ago when I was doing this, people would be very guarded when I would ask them, “What's been holding you back? What's been a struggle for you to accomplish this on your own?” There was this sense that they were like, “Well, I don't really want to tell you because then you're just going to tell me that you can do it, that you can help me with it,” which is so lawyer.

Trust your spidey senses on that. I hear this from you too, Sarah, if you tell me that this is something that's held you back in the past and it's not something that I can help you with or that my program will address, I'm going to tell you, because I'm going to feel horrible. If I start working with someone and realize that I'm not the best option for them, that is the worst, that is the absolute worst. If somebody asks you or if you have a concern, asks you, “What's holding you back? What has made it so hard for you to make progress in the past?” and you tell them, listen to their answer. If it feels smarmy and scammy and they're trying to suck you in, listen to that because if that's how you feel, you're not going to trust them in their program or while you're working with them. But you may get someone who tells you like, “I don't really know if I can help you with that.” That's a much better answer in my opinion than someone who's like, “Oh, yeah, totally, I can help you with that and here's how,” and you have the sense that you don't believe them. You can trust that sense that you don't believe them, but I guess I'm saying trust yourself enough to be vulnerable so that you can figure out where the best fit for you is. Does that make sense?

Sarah Cottrell: Yes, totally. I think asking specific questions and seeing if you actually get specific answers to the specific question; if someone asked me, “Does your program have X or Y,” and it doesn't, I'm not going to say, “Oh, yeah,” or “My program is great,” and totally ignore the question. I'm going to say, “That's not a piece of it. Here's someone who I know who does that,” or “Here's a resource.” In other words, a real conversation that's actually answering the question, that's definitely something that you want to look for and keep in mind when you're thinking about “Do I want to work with this person one-on-one? Do I want to be a part of this program?”

Annie Little: Yeah. Part of that process is just getting a feel for that person because, in addition to the answer to your question which is very important, the way in which it's delivered, you're going to get to know this person a little more and because you know them if they have a podcast or a YouTube channel and just their website and their social media. You already have a sense of what this person's like. But when you're interacting with them on your individual issue, whether it's over email or phone or whatever, you can get a sense of, “Oh, yeah, this person, I really connect with and it's going to be easy for me to work with them. It's not going to feel like a struggle. It's not going to feel like they're making me do this.” If you have that feeling around someone, go find someone else because we're not a fit for everyone. That's why there's so many of us. I'm not for everyone and that's okay. Not everyone is for me either.

Sarah Cottrell: If you don't want someone to tell you that you should go to therapy, then I'm probably not a good person to be working with. I'm sure that's not a surprise to anyone who listens to the podcast. Annie, is there anything else that you think people need to know specifically around pricing, working with a career coach either one-on-one or program?

Annie Little: Yeah. Maybe two things, because on the one-on-one side, if you're still having a hard time wrapping your mind around how expensive it can be for the one-on-one, I want you to think about, if you've been in private practice ever, think about what your billable rate is. It is what it is. If you're in a junior position, you don't have any real say in what your billable rate is. How much of your billable rate ends up going into your bank account? Rule of thumb is usually about a third. I just want to say that because if you're talking to a one-on-one coach and they give you their fee and you're thinking like, “Oh, my God, I'm going to do an hour-long session and yeah, I get some feedback or whatever for a couple weeks,” $500, that's bananas. The coach isn't putting $500 in their bank account. They're paying for their overhead. They're paying for all kinds of stuff, and also you're paying someone for their expertise, just as someone who's hiring you to do their legal work is paying for your law degree and what it took for you to pass the bar and all of your continuing legal education, it's all just baked in.

Sometimes that can help me get some perspective when I'm looking at other coaches that I'm thinking about working with and I'm like, “Oh, they've been doing this for a really long time,” and there's this element of—this will segue into the group thing—where I always like to tell people, “You can figure this out on your own. You can figure out what job you want to do next. You can figure out how to write the best resume. You can figure it all out. But at what cost to your mental health? How long is it going to take you?” When you work with someone who has experienced themselves going through it and/or having developed a system, a framework, and having their own sorts of training behind it, you're going to compress your timeline for seeing results. That's a big component of what you're paying for there in the same way that legal services work. The more you pay for legal services, the more people you've got working on your matter or you're paying people more presumably the more experience they have and so it's going to have a pretty big price tag but you're probably going to get the result you want quicker. That's just generally.

In terms of the group dynamic, because there are group programs and the Collab for one, and mine, Make Your Next Move, you have the sense, “Oh, but my situation is so unique. How can I be served in a group program?” The group program isn't going to be “This general free-for-all.” I'm going to insert a caveat real quick, when you hear the word mastermind, that's where it's a more general free-for-all. Masterminds generally don't have a curriculum or a set framework, it's just people coming together and sharing ideas, which is great and there is a time and a place for that. But if you're looking for a specific outcome like Sarah has said, what is the promise? If the promise of the program matches the outcome that you want, I encourage you to take a look at it, a very close look at it because you're going to have access to a proven framework. Let me just tell you, as an entrepreneur, you cannot just create a group program and launch it without having tested it and tried it. It just won't work. It's not something you just throw together and, “Yay,” that's what we all think and hope and that's not how it works.

If somebody has a group program out there, it's because it has worked in the past. It doesn't mean it's necessarily for you but it means that there is a tried-and-true framework process where people are consistently getting the result that they came to get. Although you may not be getting the one-on-one access that you're thinking would be most helpful, you will still get a level of one-on-one, I talk to people one-on-one over email or voice messages and on our group calls, I'm not just lecturing to my group calls and I know you're not doing that in the Collab either. You get to ask specific questions and we have different modalities and both of our programs have confidentiality clauses that our clients sign when they enroll to help with that as well. But when you have other people in the program who are going through it at the same time, if that's an element that you want to avail yourself of, that is where there is just exponential value on top of what you would get from one-on-one.

Because with one-on-one, I'm happy to do that stuff in the right circumstances but I almost feel like people are getting short changed a little because I don't have, they're not star students, but my enrollment is rolling in my program so I've got people at all stages of the process and so people are able to see what's possible. Those people who are landing interview after interview after interview and someone new comes into my program and they're like, “Oh, my God, I feel so out of my element. I'm so far behind.” That person will say, “Oh, my gosh. I was you. I was you six months ago. I felt the exact same way.” Or people will tell me that. They'll send me an email and be like, “The calls are great but I feel bad about myself after I hear all the successes people are having and how far along they are and I'm like, “Oh, thank you for sharing because that's totally normal and I'm glad you said that. Please keep coming and also reach out to these other people in the program directly because they were you.”

Being in that container makes it a lot easier for me to connect people with each other because we already have the shared confidentiality arrangement. Whereas if I'm working one-on-one with someone, I'll be like, “Okay, let me see if I can reach out to this past client and see if maybe they would want to talk to you. But I can't really give you a lot of information. I'll email them and then they'll email me to let me know whether it's okay and then I'll email you if they're not busy.” Whereas I'm like, “Go into the LinkedIn group, you're already connected to them,” or “I'll do a LinkedIn intro or whatever.” That's one of these intangibles that I'm still working on; how can I better explain this to people?

Sarah Cottrell: That's so funny you say that because literally, for me, when I was creating the program, one of the biggest benefits in my mind was the fact that you are having this experience with other lawyers who really understand what it is like. I find, however, that most people are drawn to it because of the fact that there's a framework that you can work through and then they'll come to their first group call and then they'll be like, “Oh my goodness. I didn't even think I would care about the group call piece of it but it was so amazing.” Like you said, it's interesting because it is so helpful and yet I find that it is very hard to fully articulate why that piece of it is so helpful until people experience it.

Annie Little: Yeah. It's hard to “sell” because I don't want to be like, “Well, you won't know until you come.”

Sarah Cottrell: Yeah. Lawyers are like, “Hmm, really?”

Annie Little: I know, like, “I have testimonials and also it's just, ugh, how do I explain this?”

Sarah Cottrell: It’s just magical.

Annie Little: It's just magical and with people who are shy about that, I totally respect that. I think you do too, you have recordings and so people can go back and listen and I've had people be like, “Wow, I'm pleasantly surprised by how helpful it was even listening to a call that I wasn't on,” because you get to hear what other people are going through. One thing that I like to talk about on our group calls is having people share wins because for lawyers, it's really hard for us to identify what a win is because we take our wins for granted because we tend to be such high performers. I'll have someone be like, “Oh, I don't really know if this is a win, but…” Then they're like, “I had four interviews with four tech companies last week and I got to the second and third round but I haven't heard back from this other one.” I'm like, “What? Wait.” Zoom said they decided to go another direction so I don't know what to do about that. I'm like, “But wait, but you were talking to Facebook and TikTok and you're in the third round.” I'm like, “Are those the same jobs you emailed me about asking if you should even apply? Okay. This is a win. These are wins,” those kinds of stuff.

Some people are. It's been useful for me to just take a moment to realize what a win is and to be in a place where you've got other people who will chime in, in the chat like, “Oh, my gosh. Congratulations.” Also, here's one thing that has come up, I've had my program been running over a year now so I've had people come and go, so I've had people come and they go through the process—and you and I both know how crappy the hiring process can be both within the legal industry and outside—and I've had people go through six-seven rounds and they're totally being led on and the whole community is invested in this person getting the job and then they don't get it. Once they've gotten that far into the program, they have learned that they can trust the environment and that it's safe and they can be vulnerable and come, but they have been able to say that they come to the call, they say that it didn't work out and everyone is able to say to them, “Listen, you were not wrong to think that you were going to get this job.” They strung you along. This is unacceptable yeah and we are so here for you and you deserve to be angry and sad and you can vent right now.

We talk about it as being a grieving process because you go through those stages. I don't think we think about having that support when things don't work out because we're so used to suffering alone when we're lawyers. Somebody said a couple months ago, “My real struggle right now after not getting this job is resisting the temptation to just put my head down and start applying all over again.” I'm like, “Wow, that's some really amazing awareness there.” Because we have this tendency to just white knuckle it and keep going and people are learning these new sorts of skills and ways of looking at their experience both in terms of wins and also what happens when we don't “win”, that we're allowed to have that process and that we're allowed to have support around that process as well. That's been one of the most unexpected things and again, I don't know how to communicate it so that's why I told this huge story here.

Sarah Cottrell: Yeah. No. I agree completely and I think part of it is it's what Brené Brown talks about all the time. It's the shame piece. Often, people who choose to become lawyers have a personality that is very perfectionistic or if not perfectionistic, just very high achieving and there is a level of “If I'm not doing everything exactly the way I think that I should or getting exactly the jobs that I think that I should, there's just this extreme amount of shame,” which is often very hard to handle because most people don't feel they are in a an environment where they can actually be honest about those experiences. I think the power of having other people who really know what it is like to be in the legal profession and be dealing with that and have them just empathize, true empathy I think goes such a long way towards dispelling some of the needless shame that lawyers carry around all sorts of things with their career.

Annie Little: What you're saying about lawyers and that empathy and being in an environment where it's okay to feel that way, we've talked about this where a big part of the value in our programs, whether they're one-on-one or group, is that lawyers are not used to being heard, they're not used to being listened to in a real way. I find that a sizable amount of the work that I do is really listening and hearing lawyers when they're talking about their experience. It's something where I find they'll say a little piece, “Well, this happened and this is how I feel about it,” and if I don't say anything, they'll keep talking and it's the first time that they've actually said something out loud about how they're feeling or about what their experience is like. Then once they start, they can't stop. Then when they get the thought out, if it's one-on-one, it's me, and if it's in the group, it's even better because people are like, “Yeah, me too,” or “Yeah, that's bullsh*t. That you went through that and someone said that to you, that's not okay. I've experienced it before. I've seen it before, you're not alone.”

There's just so much of when we're in our lawyer bubble at work just trying to get through the day. When you do think you have someone you can confide in or whatever, they're either going through the same thing themselves or their own stuff and they're just not equipped to handle it either. I'm just like, “Well, I mean, it's work. What do you expect? It's a job. Jobs suck. It's work for a reason.” You're like, “Okay, I guess I need to handle my sh*t better.” Whereas when you can come into these sorts of environments where that's allowed and it's actually part of the process and will enhance the results that you're going to get, it's a really big change for lawyers to have that.

Sarah Cottrell: Yeah. I literally could not agree more. Okay. As we're wrapping up this conversation. I'd love for you to share where people can find you online and find information about working with you and your program and anything else that you think people need to know.

Annie Little: Yeah. You can find me online at I’ve got a YouTube channel, JD Nation, Annie Little, Instagram. LinkedIn is where I really play around a lot and my program is called Make Your Next Move, it's a 12-month program. It's not because you have to work 12 months, it's because life with career stuff and jobs, there are cycles and there are things that come up so I feel the need to put that out. It's not so that you can feel like you're falling behind and it's not so you can feel like you have to be working for 12 months. But come hang out online. Hang out with me, ask me questions. I'm always around.

Sarah Cottrell: Thank you, Annie. I really appreciate you joining me and sharing all of your wisdom and experience. I hope that this has been really helpful for people.

Thanks so much for listening. I absolutely love getting to share this podcast with you. If you haven't yet, I invite you to download my free guide: First Steps to Leaving the Law at Until next time, have a great week.