Sarah Cottrell: Hi, and welcome to The Former Lawyer Podcast. I'm your host, Sarah Cottrell. I practiced law for 10 years and now I help unhappy lawyers ditch their soul-sucking jobs. On this show, I share advice and strategies for aspiring former lawyers, and interviews with former lawyers who have left the law behind to find careers and lives that they love.

This week, I'm sharing my conversation with Emily Whelden. Emily is a former lawyer who now works as a life coach. Specifically, she works with people who have ADHD and chronic illness. Emily also has a chronic illness herself and I asked her to come on the podcast because I had received a number of requests from listeners to talk about the subject of chronic illness and lawyering.

Emily and I talk a little bit about her own experience of lawyering and then ultimately leaving the law, but also the experience of lawyering with chronic illness and some of the unique challenges and questions that you might have if you're a lawyer who's thinking about leaving law and also chronic illness. Without further ado, let's get to my conversation with Emily.

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Hi Emily, welcome to The Former Lawyer Podcast.

Emily Whelden: Hello, thank you for having me.

Sarah Cottrell: Why don't you introduce yourself to the listeners and then we'll go from there?

Emily Whelden: Yeah, my name is Emily Whelden. I am a coach for people with ADHD and/or chronic illnesses and I'm a former lawyer myself. I work at Dixon Life Coaching now and I primarily work with lawyers with ADHD or chronic illness.

Sarah Cottrell: Yes, and I asked Emily to come on the podcast because I have received multiple requests from listeners to have someone on to talk about the experience of lawyering with chronic illness because there are lots of people who find me either because they're someone who became a lawyer and have a chronic illness or someone who has been diagnosed with a chronic illness while lawyering and in many cases, it causes people to think through “Is this what I still want to be doing? Is this compatible, the level of stress of this particular role with the other things that I am balancing with my chronic illness?”

So there are lots of issues around thinking about what they're doing and whether they want to continue doing it that come up. So Emily is here to talk about that and also to share just a little bit of her story becoming a lawyer, then a former lawyer. Emily, can we start back at the very beginning and can you tell me what made you decide to become a lawyer?

Emily Whelden: We definitely can start there. It is a long way back. I was very fortunate to be in the gifted program at my elementary school. As part of the gifted program, I got pulled out of classes four times a week for enrichment and one of the things that we did was mock trial.

In fifth grade, I did my very first mock trial competition and just absolutely fell in love. I was obsessed with it. From then on, I went to college, I went to law school. I thought I was going to become legislative counsel, I went to undergraduate in DC, and I was like, “I want to write laws for a living.” Then I realized how boring that can be. But I got back on trial team in law school and did clinic in law school and rediscovered litigation and my love for trial work. So I went on and I passed the bar and became a trial attorney at a very small firm right out of law school.

Sarah Cottrell: It's so interesting. I think so many of us, so many people have come on the podcast, and people who I work with really developed the idea that they want to be a lawyer at a very young age, whether it was like your experience or just being told like, “You're really good at arguing, you should be a lawyer,” or whatever. Often, I find that for people, it's like their idea of what it is going to be like. Like for us, it's very much formed by our idea of what it would be like when we were much younger. I'm curious for you when you started practicing, what was your experience?

Emily Whelden: Well, my experience was very unique I think because in law school, I went to Catholic law school and they have a really strong legal clinic program. So by the time I graduated, I had three in-term semesters worth of legal clinic and a full summer of legal clinic. So I was really comfortable litigating and doing real trial work when I graduated because I had this amazing training program.

I knew I didn't want to go to a big firm because I've had chronic health conditions my entire life and I didn't feel like a big firm would be as accommodating or as understanding as a smaller firm. I can hindsight query that assumption but it was the assumption I was working with.

I had this amazing opportunity to do a wide variety of work. I did everything from family law and appellate advocacy, brief writing, even oral arguments. But the bulk of my work was with probate and guardianship. I ended up becoming the legal guardian for several people in the District of Columbia. I loved that, but it's a 24-hour-a-day schedule, possibly, when you are a legal guardian and my health started deteriorating.

I was no longer able to really give that the energy that I wanted to and needed to while also keeping myself healthy. So I decided to transition my practice from guardianship to state planning and administration. I ended up getting into a mid-sized firm in the Bethesda, Maryland area and was sitting at a desk for the first time in my entire career all day, every day, bored to tears.

Because guardianship is really the emergent practice of law. What's the biggest emergency right now? Who do I need to help right now? That was really a helpful structure for me. However, it was masking undiagnosed ADHD. When I went to a “regular” office job, a regular law firm job, a lot of the cracks started to appear and I ended up getting diagnosed with ADHD on my 31st birthday.

Sarah Cottrell: Yeah. I know you and I were talking a little bit before this that ADHD comes up on the podcast quite a bit because many, many, many of the people who I work with and know and love and live in the same house with have ADHD, and because it is so prevalent amongst lawyers, especially I think prevalent and often undiagnosed for a variety of reasons that we've talked about on the podcast before, it really has a significant effect on so many people's experience of the practice.

Emily Whelden: Yes, and there are various numbers floating around but the CREEL Report, which came out admittedly in 2017, so this is very outdated, estimated that 12 1/2% of attorneys in the United States had ADHD, or rather they were self-reporting that they had ADHD, which at the time is more than twice the average of the general adult population and almost none of them are open about it at work.

Sarah Cottrell: Yeah, which is wild to me because it's already twice and just my own experience, working with lawyers tells me that 12% were self-reporting and probably another, I don't know, I would probably estimate another 10% to 12% are undiagnosed. That might just be because I see a disproportionate number of people who ultimately end up with an ADHD diagnosis.

But anyway, that was like an ADHD aside. I would like to go back to something you said. You said you originally decided that you wanted to go to a smaller firm because you thought it potentially would be more accommodating for your chronic health conditions and now you're not sure that that's completely accurate. Could you tell me a little bit about that, about how your thinking has evolved about that over time?

Emily Whelden: Yeah, so I work primarily with lawyers now and lawyers in all different practice contexts: government, big firms, small firms, solos. One thing that the big firms have, which small firms cannot provide is resources. When I worked at a mid-sized firm, I had an assistant. I didn't have an assistant when I worked at a boutique firm. I mean, we didn't even always have somebody to answer the phones who wasn't an attorney.

That type of support can be very useful and helpful when you have a chronic health condition because it takes the things that aren't necessarily your area of passion or genius, however you want to phrase it, and it gives them to someone else. Not all of them, of course, lawyers at big firms still have admin, but the support that a larger firm can provide is backed by the resources of a larger firm.

That being said, my initial assumption that by being at a smaller firm, I would be a little bit more humanized, my bosses would be able to make more individualized decisions about me and would have a better understanding of my work and value that I brought to their organization as an individual, those were all true, I think, but whether it was as dispositive about whether I would be best fit at a small firm versus a larger firm, I think is up for debate.

That being said, my chronic illness when I chose to go to a small firm was primarily chronic migraine disease, which is historically very stigmatized and not necessarily treated with the seriousness that it deserves, and in my case, the seriousness with which it impacts me. But it's unpredictable.

That's the struggle with chronic illness. Most of the time, the chronic illness impacts you in ways that are clear and obvious to other people, but which we cannot be forecasted. So you come across potentially as unreliable, maybe not able to handle the pressure, not able to handle stress well, or something like that because we know that stress produces rising cortisol levels, and that produces real physiological impacts on people who have a chronic illness and makes you more likely to have a chronic health condition flare up.

Sarah Cottrell: I was just going to say, I think that is so important and it's a huge piece of why I got the request to have someone on the podcast to talk about chronic health conditions multiple times because one, lawyering in many contexts is stressful and so by its nature often is something that might cause someone who has a chronic health condition to flare.

But also to your point about predictability, I think this is one of the things that is the most frustrating for people who have these experiences because so often, the unpredictable nature or the fact that they can't forecast when they're going to have a migraine, when they're going to have some other type of flare, or when they're going to need some additional support is not seen as treated in a way as though it says something about them as a person and their desire to work as opposed to just part of being a human being.

I think that's a big part of the question that people have of, “Okay, I am experiencing this, I'm seeing that it is having some adverse effects on me because the stress itself is causing problems for my health.” But then also there's the psychological burden of feeling like, “And also people are not fully understanding me, what's going on, and why these things are happening.”

Then at the same time, and I know we can talk some more about this, there's this sense of “But I also don't want to have to tell everyone all of my private health information in order to feel like I'm somehow ‘justified’ in needing accommodations or that sort of thing.” That was a lot of thoughts altogether. But I'd love to hear your thoughts about that and what you've seen with your clients and your own experience.

Emily Whelden: Yeah, so I think what you're speaking to is this level of stigma associated with being not 100% yourself in the legal field. We see this in all different contexts within the legal field, but for better or worse, there is still this ethos of strength that you want to project as an attorney. There is, in many places, a culture that does not promote vulnerability or any kind of weakness.

Many people think of chronic health conditions as weaknesses: You're unreliable or I don't want to push you too hard because then you'll just get sick and be out. So there certainly is a large stigma around it. Many of my clients are not open about their health challenges at work either. They spend a lot of energy masking and covering over those physical limitations.

That's for a variety of reasons. One of the big ones is it's not everybody's business. It is uncomfortable for people to ask you how you're doing and say, "Oh, I'm not really feeling that well," and then have them ask more probing questions. You don't necessarily owe that to people.

There's also a risk that you say something and then the company will say, "Oh, well, you're no longer able to do your job. We can't accommodate you in a way that will allow you to do your job, so we have to let you go." Or, "We can't accommodate you and so now we're going to create a situation where you can't effectively do your job and you'll quit." That's a very real concern.

People with chronic illness or disability are more likely than their non-disabled peers to have a negative employment outcome, to be fired, to have to quit, or to have their job reduced if the firm is going through a reduction in force, just have their position cut. That is, it doesn't necessarily rise or rather the statistical rates of employment discrimination suits do not match what people report that they've experienced.

There's a real legitimate fear that being open about your health or your health limitations will cause you to lose your job. For most people who have jobs and are working, they want to continue working. Most people want to have some sort of purpose in their career, and many people tie a lot of their self-esteem to their career. So when you are faced with the potential of a negative career outcome, employment outcome, that's really scary and can make you pull back.

Sarah Cottrell: Yeah, I'm curious as you are working with clients or just thinking about it for yourself, a lot of people, I think, will come to this episode potentially looking for ideas about how to think through “Should I keep doing what I'm doing, or should I change something about what I'm doing?” Emily, I'm wondering if you have thoughts or questions that you think would be helpful for people to think through as they're trying to identify what is the right path forward for them.

Emily Whelden: Yeah. One of the things that I asked myself and I've asked several clients is if you carry on this path with no changes, what does next year look like? What does five years from now look like? What does 10 years from now look like? If that answer is not good, if it's not, "Oh, I've made partner and I'm thriving. I'm so happy," or it's not “I've hit this career milestone I've been working towards and I'm killing it on billable hours,” and all of those things, but instead, if it is like, "Oh, I'm burned out or I'm sick and disabled," or, "Thinking about 10 years, doing this 10 years with nothing changing makes me want to cry," that's a sign that something is not fitting, that something has to change.

Then you want to do that deep exploration of, "What does change look like? Am I ready for that? Are there smaller incremental changes that would help, would improve what's happening? Is this the right organization for me?” Because sometimes it's not the job itself, it really is the organization that is supporting or, in many circumstances, not supporting. Do I just need to change supervisors to someone who's more humanizing?

Those are the kinds of questions that can help clarify the path. When I was thinking about what to do after deciding that I didn't want to be a lawyer anymore, one of the things that my coach at the time asked me was, "When you think about a position that you're looking at, would you want to be that person's boss one day?"

The reason that question was so informative to me was that it said, "Okay, this job looks interesting, but what does the path look like? Is this something that is going to keep you engaged and interested and is sustainable for you?” Because if you don't want to be the boss for the position that you're going towards, then you've just hamstrung your upward mobility.

You're going to be there for however long you're there, but eventually you're going to get bored, or you're going to stagnate, you're going to stop learning. That is where people really struggle. Because when you're stagnant, you're unsatisfied. No one likes to be standing still, doing the same thing over and over again, then it becomes a grind.

When you're in transitions, maybe sometimes it's okay to say, “No, this is just a transitional job. I just need to work this for six months, a year, two years, and figure out what I want, but I need to pay my bills and support myself during this transition. I know going into it that this is not going to be my permanent place,” that's okay too.

But if you're really trying to think through “What does sustainable work look like with a chronic illness?” you have to be thinking two and three steps ahead in order to work through what characteristics you really need out of a job.

Sarah Cottrell: I'm wondering, because I know this is a question that comes up for a lot of lawyers for many different reasons, but how do you suggest people think through the question of “Is it just this particular place of employment or is it this type of job? Is it just my particular law firm or is it being a lawyer in general?” Because I know that for many people, they can identify like, “This isn't working,” but it can be a struggle to figure out like, “Is it just because this particular place is a problem or is it the entire thing?”

I imagine that with chronic health conditions, there's that additional question of how to work through and discern which is true. So what would you recommend people think about?

Emily Whelden: I would suggest people get information from their peers at other organizations or other formats. Do you know a friend who's a government attorney or do you know a friend at a really small firm, a really big firm, or just a different big firm? Talk to them and ask them what the culture is like at their job because figuring out whether it's culture or career path is a really difficult line to walk. That being said, there are wildly different cultures across different organizations so it might very well be just a cultural shift is needed.

Another thing to do is connect with, if you don't have people who also have a chronic health condition and can give you the inside scoop on an organization or a company that you're considering switching to or trying to discern whether this is culture at your organization that's the problem or whether it's the career, join your local bar organization for the disabled bar because those attorneys have an analogous or a similar experience to you, or at least they will have some nuggets that you can take away and how to figure out whether it's culture versus career.

The other thing to think about is, do you love the work? Is the thing that's making you feel questioning about your current position, is it the work or is it the people around you? Can you get in the zone and do whatever your specialization is and enjoy that?

Then what's preventing you from getting in that zone? Is it the partner who won't stop pinging you because they're asking you for something and never giving you enough time to finish your work? Or is it the fact that the billable expectation is such that you have to be working an eight to 10-hour day every day and that's physically unsustainable for you? What would an accommodation of a reduced billable do for you there?

It's like playing chess in that you have to predict, you have to make your current move based on the predictions of what might happen in the future on the board. That's not easy to do but you can do that by getting more information and figuring out what your needs are in a more crystallized and clear way in order to answer the question of is this culture or is this career?

Sarah Cottrell: That's really helpful. I'm wondering, I think there are a good number of people, including people who have reached out to me, who experience some chronic health condition and they're asking themselves, “Can I even be a lawyer with this condition?”

When I have conversations with people, of course, I tell them the most lawyerly answer ever is also the correct answer in so many of these contexts, which is, "It depends." But I'm wondering if you have anything that you would say specifically to people who are in that position and are feeling discouraged and they don't know, but they're not sure whether they can continue lawyering.

Emily Whelden: Yeah. This isn't an answer, but it is a question that is an answer. Because I asked myself this, “Can I do this? Can I handle this format?” I would say that that's part of the question, but it's an incomplete question. The first fundamental thing has to be, “Do I want to?” Because you can modify, you can accommodate yourself in any number of ways.

People can do almost anything. It just might look differently than the way everyone else does it. If you want to be a lawyer, that doesn't necessarily mean you're working full-time as a lawyer. It doesn't necessarily mean you're even working for your job as a lawyer. Maybe you do a more low-key nine-to-five job because that's what your body can physically handle and then two or three times a month, you go and volunteer at a legal aid walk-in center, providing brief information for free to indigent people.

There are different ways to be a lawyer. But if you don't want it anymore, then that's really more instructive and informative than “What do I need to do and can I do this anymore?” Because I would hazard a guess that if you're asking yourself, "Can I do this anymore?" the answer is almost always going to be “Not in this way.” Then the question is, "Well, what way works for me?"

Sarah Cottrell: Yes. First of all, I think the question of "Do I want to do this?" fundamentally, for any lawyer who's thinking about not lawyering is a huge part of the question. Often, for various reasons, those of us who became lawyers don't think of that as the primary question.

In fact, a lot of us have been conditioned through our life experiences and other things to actually feel like even if we don't want to do it, even if it doesn't feel like the right fit, that we have this sense of “But I need to prove that I can.” I think that drives many of us who became lawyers, even in situations where we're realizing “This isn't necessarily a great fit. I don't even necessarily want to do this.”

I'm curious, Emily, if you have found or experienced that yourself or find that that's something that comes up in the experiences of lawyers that you know with chronic health conditions, because I find across the board that's often a piece of it, like “I don't really want to do it, but I feel like I need to prove that I can.”

Emily Whelden: I don't know. I'm not sure if it's to prove that you can, but I certainly do hear from people surprise when the question is raised or you tell someone you don't want to be a lawyer. Often the response you get from external people is surprise, shock, maybe anger. Because for a lot of us, we've spent most of our life and certainly a large portion of our academic career working towards becoming a lawyer.

There's a lot of debt associated with becoming a lawyer for most people. It seems, at least, for example, when I told a family member that I was no longer going to be practicing as a lawyer, that I was going to become a life coach instead, they laughed at me and they said, "What on earth are you talking about? You've been working towards this since fifth grade. You love being a lawyer."

I had to tell them, "I did love being a lawyer, but I don't love it anymore." And that's okay. But it's hard to see something that you've worked for, for most of your life, especially because a lot of people go to law school straight from undergrad and say, "You know, my needs have changed and this may have fit me before, but it doesn't fit me now. It doesn't fit who I am today."

That's a big thing to say. It's a big thing for anybody to say, almost about every major life choice that we make, but career included. I think for a lot of my clients, there's a certain grief associated with that, that what you thought it would be isn't what it turned out to be. That takes some time to process through and to acknowledge and accept.

Sarah Cottrell: Yes, and in the show notes we'll link, I did an episode a while back that was about grief and how grief is part of the process of deciding to make a change for all sorts of reasons.

On the podcast before, we've talked some about disclosure to employers about ADHD and mental health issues and some of the factors that go into deciding whether someone is going to do that or not. I'm interested to know if you have anything that you think the listeners should know or think about when it comes to chronic illness and asking for accommodations or deciding to disclose.

Let me just say one of the things we've talked about quite a bit is the fact that for many people, they decide not to disclose and there are many reasons why that decision is extremely understandable. What thoughts do you have around chronic illness, disclosure, accommodations, etc?

Emily Whelden: This comes up a lot with my clients both in the ADHD context and in the chronic illness context. I want to acknowledge, and you've touched on this, that disclosure is a very personal question and no two people will come to the decision in the same way and also all decisions about it are valid. So if you choose to disclose, that's valid. If you choose not to disclose, that's also valid.

One of the things that people in the chronic illness or people who have a chronic illness or are in that community talk about regularly is the cost of not disclosing versus the cost of disclosing.

The cost of not disclosing is that for a lot of them, they choose to pretend as though nothing is wrong and that they don't need any additional supports. They just power through until they burn out and have a major health crisis. That's not sustainable. It's also not supportive of yourself. It's not self-supportive.

There's a group who chooses to disclose because they cannot but disclose, the very obvious physical manifestations of illness or I have a very unique type of migraine that mimics a stroke so when I am getting a migraine, it's really obvious to people that I'm not well. So I have to tell my co-workers, “Hey, I'm okay. I don't need to go to the hospital right now, but I do need to go home. But please don't be worried about me. This happens all the time.”

There are those two camps: the “I choose not to disclose and I will hide it to my detriment,” and “I choose to disclose because I can't avoid people figuring it out and knowing.” Then there are people in the middle who could disclose or they have disclosed but only to a select few people.

Maybe they haven't formally disclosed, but they've confided in an immediate supervisor or a co-worker and they are okay enough that they muddle through and get what they need to get done finished and with various levels of success, progress through their career.

Whether to disclose or not really comes down to what you need out of the disclosure. Do you need a formal accommodation? Then you're probably going to have to disclose. A formal accommodation might look like a reduction in billable hours. It might look like a more flexible work-from-home schedule versus work in-office schedule. It might look like additional time for projects, administrative support, or something.

Then there are people who don't feel like they need formal accommodation, but they would like informal accommodations. For those people, I always say, “Think about how to frame it as a support without framing it as an accommodation.”

A great example of this is when I was working as a lawyer, I needed to have some sort of visual, external reminder of all of the work that I was doing. With ADHD and chronic migraine, I really struggle with working memory and brain fog. Sometimes I would forget what I was working on while I was working on it.

So I asked for an additional whiteboard to be installed in my office that was in my direct line of view so that when I looked up from my computer, I could just see the whiteboard, and it wasn't very big, it was like poster-sized, and I would write what I was working on, on that whiteboard so that when I looked up, I would just go, “Oh, I was working on this accounting,” or “Oh, I was drafting this brief,” or whatever it was and that would help cue me back.

That wasn't through a formal accommodation process. I just asked the office supply person if I could have another whiteboard. There are ways to do that. Also, what is the cost of disclosing? If you're the type of person who feels very shy, hesitant, or embarrassed about your condition, disclosure might come with a really high social cost for you.

People might find out and they might ask you about it and that might feel very uncomfortable. Or you might ask for accommodation and suffer a negative employment outcome and put a target on yourself. There are a lot of things to consider about whether to disclose or not. I think one of the primary things that you have to think about is “What is the accommodation I'm asking for? And do I need to disclose to get that?”

Sarah Cottrell: I think that's all really great advice. As we're getting to the end of our conversation, Emily, I'm wondering if there's anything else that you would like to share from your story or about lawyering with chronic illness that you think people need to know.

Emily Whelden: Yeah. I think one of the things that I often see with clients and admittedly, I work as a coach so my entire job is helping clients see things from new perspectives, but I often see that people are stuck in "should" mode: I should be able to do this. I should be able to work on this project without getting distracted or without needing a break. Or I shouldn't need this support. Or who would even think to ask for that? That seems unnecessary.

I would say that it's only unnecessary if you don't need it, if it wouldn't be helpful for you. Ask for the extra whiteboard. Are you going to use it? Yes, great, you need it, ask for it. Are you struggling to make it in on time regularly because you can't drive when you're not feeling well?

Or maybe you have diabetes and you have to get your lab work done regularly and you need a more flexible work schedule for that. Do you need it? Then ask for it. Accommodating yourself, which by that I mean doing things to support your own needs, is fundamental to a successful life with chronic illness. You can't be successful in your career if you're not doing that in other areas of your life.

I coach a group coaching program about how to manage chronic health conditions with ADHD because there's a high comorbidity rate and one of the things I teach in that group is energy management. So how can you preserve your energy in order to be able to give more or give your better energy on the things you really value, like your career or your family, as opposed to the things you don't necessarily value? And really questioning and querying what are your values, then how can you support your health through those values?

Sarah Cottrell: Yeah, I think that's so good. I think in particular, many of us who became lawyers for all sorts of reasons are not great at recognizing our needs as needs. So whether you're someone who's listening and you experience a chronic illness or you are a lawyer who doesn't have that experience, there is a pretty good chance that it may be a bit of a struggle for you to recognize that you do have legitimate needs, which is one of the many reasons why on this podcast, I so often talk about going to therapy and seeing a therapist because being able to recognize what you need is going to make a huge difference in terms of how you're able to approach your career and is something that is good to address in therapy.

Emily Whelden: Yes. And I'll double down on that and give a small plug for coaching, which is different than therapy, and any coach who tells you they're comparable is not within their scope of practice.

Sarah Cottrell: Highly questionable.

Emily Whelden: Highly questionable. Don't use them, but the thing about coaching that's different than therapy, so if you've already done therapy and you're not really feeling it, coaching is forward-looking. Coaching is all about figuring out how to problem-solve, how to see maybe from a different perspective, but from a complementary perspective.

I like to describe coaching as a mirror that lets you see things in a light or from an angle that you haven't seen them before and think about things in new ways. Therapy can do that too, also really great. But sometimes people don't feel comfortable with therapy and I'm also a coach. So, just a small plug for coaching in addition to therapy in exchange.

Sarah Cottrell: Love it. Okay, Emily, if people want to connect with you, where can they find you online?

Emily Whelden: Yes. You can go to dixonlifecoaching.com. I'm one of the team coaches featured there. You can also find me on LinkedIn.

Sarah Cottrell: Amazing. Okay, well, Emily, I really appreciate you joining me today. This has been a highly requested topic, and I really appreciate you sharing all of your own experience and your expertise.

Emily Whelden: Thank you for having me.

Sarah Cottrell: 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 formerlawyer.com/first. Until next time, have a great week.