Get Out: Loathing my Job, Lonely Without Friends & Hobbies

Hi Jennifer,

Thanks for taking questions.  I would love some advice on how to figure out what interests me so that I can determine what career to pursue. 

I fell into the law after working a few jobs out of college but not really knowing what I wanted to do for a career.  I’ve hated it since day 1 and, now 15 years in, I fear the law is going to be a life sentence! 

I handle regulatory compliance and mergers and acquisitions for telecommunications companies. I hate the subject matter because it’s very technical, constantly changing, and hard for me to ever fully understand or gain a sense of mastery. 

And finally, I’m an introvert and hate the business development, conference speaking, etc. aspects of my position. 

I’ve wanted to leave the law for a long time but I have no idea of what I want to do.  I went to law school at 30 and I’m a single mom of 2. Now at age 50 I have no hobbies or friends and I have absolutely no idea of what job or career would interest me or that I realistically could pursue at this point.  

I don’t feel that my skills transfer readily to other careers and I don’t want to go in-house to a telecom company.  I enjoy doing things where I can see immediate results, and listening to productivity and personal finance podcasts.  

I don’t see how I can turn those interests into a career and I just feel stuck.  

Thanks for letting me vent.


Uncertain Future

Dear Uncertain,

I applaud your desire to figure out what work would be interesting and rewarding for you. That’s a big step for someone who lurched into law and stayed with it for 15 years despite loathing it.

But, during those 15 years you ignored, stuffed away, and silenced your inner voice. Without that voice to guide you, you’ve missed out on important cues about what lights you up and makes life (including work) worth living.

Right now, your inner voice is bitterly hunched in a corner on her millionth cigarette, with a bottle of bourbon at hand. (Hopefully it’s Angel’s Envy, my favorite.) She’s a hardened cynic by now, and she isn’t going to believe your interest is genuine. Initially, anyway.

She has a point, after all. No one likes being ignored, especially not for a couple decades. So to get her to talk, you’re going to have to woo her. A lot.

Listen to the Voices in Your Head

The first step is simply get your inner voice talking. You’ll need to show up consistently, listen deeply, and act upon what you hear. 

Say you suddenly, urgently want to live in the middle of nowhere—pay attention. Maybe don’t pack up that second and bolt, but don’t automatically swat that notion away as impossible or impractical, either. 

Instead, honor it. Rent a cabin in a remote vacation spot. Or make plans to go hike/hang outdoors away from people. The important thing is action; simply agreeing, mentally, means next to nothing to your inner voice.  Show your inner voice you are taking her seriously.

Embrace the Crazy 

Spend a couple months, minimum, on paying attention to your “crazy” longings, and indulging them as much as possible.

As you are doing this listening and indulging, keep notes:

  • What pops into your head that you want to try/be/do? (Do not self-edit)
  • What does the full vision of that look like?
  • What did you do?
  • Rate how you felt before you did it (1-10).
  • Rate how you felt after you did it (1-10).
  • Would you want to do it, or something like it, again?

The point of this phase is not to discover what you want to do with the rest of your life. You may get lucky and have that epiphany, but that’s a bonus at this stage. Your initial goal is to tune into your inner voice, and trust that what it wants will benefit you as a whole person. 

You will get to the epiphany part. Trusting your inner voice’s guidance will get you there faster.

At the end of a couple months, you and your inner voice should be on decent speaking terms. Plus, your stress level should be declining.

Use a Really Big Net

What comes after this initial part of getting in tune with yourself again? Keep doing more wooing. Then also start looking at non-lawyer job ads. 

man repairing large blue nets

Photo by Harry Piqué on Unsplash

If you’ve stayed intrigued by productivity podcasts, for example, maybe you look at ads for corporate training or consulting companies, or any other place that highly values productivity. 

Cast your net widely. Think about jobs and industries that don’t necessarily have the label of your new favorite obsessions, but do contain their function. People who enjoy teaching, for example, perform that function in non-profits, in training new employees, and in leadership development, to name a few. You can get even more ideas of what jobs require the function you want in your work at, a brilliant little site developed by the Department of Labor.

This is idea generation time. Right now, you’re looking for ads that pique your interest, regardless of pay, location, or any other logistical concern.

Bright Shiny Objects: YES
Clenched Body: NO

Notice what draws your attention. Notice what makes your stomach or shoulders clench. The jobs that make you clenched or depressed, or that you are talking yourself into considering? Stop entertaining those as ideas for your next gig. I don’t care how well they pay or how much sense they make on paper, because for YOU, they don’t make sense.

At the same time, you need to talk to people about your ideas and their experiences. Yes, even if you’re an introvert. Bear in mind that one person’s story isn’t the entire truth about a job, industry, or your prospects in it; it’s a data point. Make sure you gather many of those before you decide anything.

Plus, you need a tribe of people that likes some of the things you do, and who have a similar mindset. You know, like friends. Showing up regularly to do things you like with nice people is a good way to find some tribe members, and gain perspectives that lawyers usually lack.

The Right Stuff

Most importantly, worry about the practicalities of a new career (pay, location, transferable skills) only after you’ve identified the direction you want to head. Otherwise, you’ll end up in a situation much like your current one: You make the money you want and have the “right” skills and experience for the job, but it’s a terrible fit for your soul. 

field notes phone sharpies

Photo by Kari Shea on Unsplash

Once you know your direction, then you can start considering the nuts and bolts of how to get there. Identify your ideal job(s). Then compare your current skills, experience, and knowledge base with what those jobs ask for. (Also: You don’t need everything on the list. Promise.)

Instead, use your problem-solving moxie.

Ask yourself, and others, how you can get the items you lack?

  • take an online class?
  • make connections you need through volunteer work?
  • find a job in your current industry that would give you experience you need to make that jump?

You had a life before law school, and you’ll have a rich and wonderful life after law, too. Once you’re back on speaking terms with your inner voice, you’ve totally got this.

Jennifer Alvey is a recovering lawyer and advice column addict. She has made connections at crafting classes that led to actual paying freelance gigs. 

What’s your most pressing question about changing your career? Send it to Or, if you want a personal consultation, you can email Jennifer to set that up.

Get Out: I Hate People!

Dear Jennifer,

I became a lawyer entirely because I needed more schooling to get a job that would pay enough for me to pay my child support, kids needs/fees, and still survive.  My hope was regular pay and possibly health insurance at some point.  After 4 years in private practice, I closed shop, because my mental health was shot and my clients weren’t paying anyway.
While I did find a job working in-house corporate, I’m really just Done with people.  And other lawyers.  Who I mostly despise (with limited exceptions).  I do love helping people, but it stresses me out to the point of badly affecting my mental health.  Still. Again.
I will finally be able to live where I want to once my baby graduates from high school in a year and a half.  Problem is, I don’t know that I can find work where I want to live, so I’m looking at exclusively online employment.  There are a thousand and one posts on Pinterest about “not a scam” “work from home” jobs, but seriously…which/what/where does one find one of these jobs that actually pays, that I can use those skills of brief writing, or reviewing documents…that’s an actual real work from home job.  Not that I don’t totally trust Pinterest, but ya know…
Done With People

Dear Done,

You seem very certain that telecommuting will solve your dissatisfaction with work and law, but I’m not convinced.

I’ve worked from home for a decade. In addition to coaching, I have also kept my hand in freelance writing and editing. Trust me, you will be dealing with people. Often, it’s harder to do that remotely, because you can’t always soften a message with just an emoji. Also, isolation can be a real problem, even for introverts.

Care and Feeding for Introverts

Introverts do not achieve nirvana simply by exiling people from their lives. We all need connection with others, even if the amount of it varies. Reading between the lines of your letter, you do seem fairly introverted.

So I’m wondering if you are neglecting your legitimate introvert needs, and that neglect is making your miserable?

Lawyer Susan Cain discussed in her book Quiet: The Power of Introverts in a World That Can’t Stop Talking, that introversion is about stimulation levels. Introverts can get overwhelmed quickly by noise, movement, and ideas, for example.

pink water lily against backdrop of leaves, with reflection of it on water in the foreground

One big key to introvert happiness is managing those stimulation levels to prevent frequent overwhelm. We can’t completely avoid overstimulation, but we can recognize where it routinely happens, and plan accordingly.

The bottom line: Make sure you get the alone time you need, starting today. I don’t care if you feel like you need “too much.” We wouldn’t tell water lilies they don’t need so much water; it’s the same for our own nervous system wiring. We can’t change our wiring, but we can find strategies to function better and more happily.

Really Helping People

As one helper to another, I’m going to share an important reminder: It is not your job to fix people!

Helper types tend to believe that if we just fix people’s upsets, everyone will relax and be happy. (I’m a charter member of that club.)

But fixing emotional upset for people—instead of helping them learn to self-regulate—often does them a disservice. We steal their chance to grow and learn, in favor of calming things down for us in that moment. Because conflict stresses us the hell out!

Yet what if the impatient head of marketing needs to learn some patience and self-reflection to be both better at her job, and at her life? Taking on the job of diffusing her impatience does neither of you any favors. She doesn’t learn to self-regulate, and you will deal with her impatience again and again.

vivid blue door with yellow sign saying Visitors must stay within designated walkway bounded by yellow lines

If colleagues and clients (and friends, for that matter) try to make their emotional work your problem, decline. Setting a boundary like that usually makes people even more persistent for a while, i.e., they become a huge pain and you wish the ground would swallow them.

Eventually, if you are firm and consistent, they will either learn what they need to, or find someone else willing to do their emotional labor. Either way, you are out of the crosshairs.

Logistically Speaking

I’m not saying telecommuting isn’t a good plan. But the leap from “I don’t know if I can find work where I want to live” and “I must therefore telecommute” ignores a lot of possibilities.

For instance, are there any kind of writing jobs, not necessarily legal writing ones, in your new locale?  If yes, but you lack experience/training, there are plenty of online courses that can get you up to speed.

close up of hands typing on Apple laptop

If you enjoy law practice, but not the people, what about handling local attorneys’ overflow? Many small/solo practitioners don’t like writing briefs; maybe you could take that off their hands.

It’s easy enough to set up searches on Glassdoor or LinkedIn for telecommuting jobs, too.

The point is, there are many avenues you can explore.

I see some wonderful opportunities for you to add some magic and zest to your life with this transition. Open your eyes and heart to them, and see what happens. You got this.

Jennifer Alvey is a recovering lawyer who has never taken a psychology class, but knows a thing or two about being an overwhelmed introvert and switching jobs. She has been coaching unhappy lawyers on career change for a decade. You can email your question, or set up an individual consultation, by emailing her at

Get Out: Old, Burned Out, Few Skills

Dear Jennifer,

I’m a 56 year old woman who graduated law school in 1993. I’ve spent 25 years in public interest law, the first 5 as a public defender and the last 20 as a guardian ad litem for abused, neglected, and delinquent kids. I have enough credit in my state pension plan to retire with a pension check of 60% of my monthly salary.

I am extremely burned out from 25 years of heartbreaking situations and feeling often unable to help these people. I feel like I’m barely a lawyer anymore, and the niche of child protection is so narrow. I need a new kind of work, but I have no ideas and few skills.

Dear Barely a Lawyer:

The first thing I need to say is that YOU. ARE. AMAZING.

woman jumping crevice sammie-vasquez--unsplash

Photo by Sammie Vasquez on Unsplash

Most people who work in public interest law and deal with heartbreaking situations daily usually don’t last more than a few years. Compassion fatigue and depression drive them out. The fact that you’ve lasted 25 years in this area speaks volumes about your resilience and commitment to those in distress.

Depression Talking

Lawyers who say they lack skills are usually either 1) very new lawyers, or 2) very depressed lawyers. I think you know where you might fall.

If you aren’t seeing a therapist, please do. I may be completely off-base here, but it wouldn’t hurt to find out from a therapist that I’m totally wrong. And if I’m not, then you will get some great support during your transition to whatever is coming next.

More Law?

If you’re after a lawyer gig, one possibility is opening your own family law practice.

Yes, it’s daunting, but many resources exist about how to do it. Your experiences would be highly valuable to a divorcing parent who is worried about their soon-to-be ex’s (in)ability to be a custodial parent. You could be a fantastic advocate for those kinds of divorce situations, or negotiating modifications of prior custody agreements.

Skills, You Have Some

But let’s say you want out of law completely. Even though we’ve never met or talked, I am willing to bet you have most of these skills:

  • Keep composure in high-stress, high-stakes, volatile situations;
  • Mediate in the same types of situations;
  • Successfully handle/juggle competing priorities;
  • Pivot quickly when circumstances suddenly change;
  • Stay focused on end goals of client;
  • Evaluate complicated, emotional fact patterns objectively and compassionately;
  • Keep track of complex details in multiple cases simultaneously;
  • Interact with judges and other public officials frequently; and
  • Staunchly defend/argue client’s needs in variety of contexts.

I’m sure there are many more items that could be on this list. These skills are desirable and highly transferable.

Emotional Intelligence

While you may be thinking, “OK, but doesn’t every lawyer do these things?” the answer is no, they don’t.

Lawyers are usually poor at handling situations where emotions fly fast and furious. As a group, lawyers score below average in emotional intelligence. Many of the skills I’ve pointed out require an above-average amount of emotional intelligence.

Between your social/emotional intelligence and your lawyer training, I could easily see roles for you in non-profits that advocate for abused children, or for related areas like healthcare, justice system reform, or groups that support the less fortunate in our society.

Bypass the staff attorneys roles. Instead, seek out jobs in community engagement/education, or advocacy in state and local government settings. I could see you in an executive director role or operations chief, too.

Get Out—Into Nature

Regardless of what path(s) you decide to pursue, one important thing you need to do right now is start taking better care of your soul.

I understand that you are exhausted and grieving for those you couldn’t save. But have you ever stopped to count those whose lives are better for your actions? That can be very healing.

Another key way to heal the exhaustion and heartbreak is adding doses of nature to your daily routine. Gobs of data vouch for the importance of outdoor time for calming the mind and lowering stress.

You don’t need to go on hour-long hikes; a visit to your own backyard for even 15 minutes daily can make a huge impact on your wellbeing over a few weeks.

Go Have Fun

At least weekly, do something fun and frivolous for an hour. The important thing is that whatever you do, it’s fun and festive for you. This is not something calculated to get a job or likes on social media, OK?

And yes, you must leave your dwelling. The more you immerse yourself in a different space, the more refreshed you will be. Our homes are comfortable refuges, yes, but also nagging reminders of undone chores and projects. Leave that burden behind for a little while.

Will this be easy? I doubt it. Changing a mindset rarely is.

But will it be worth it? Absolutely.

Stress kills us by triggering health problems that might have lain dormant. Plus it robs us of joy. Who wouldn’t want to trade poor health and misery for a chance at something much better?

Work on healing, gather your courage, and be open to possibilities and synchronicity. You got this.

Jennifer Alvey is a recovering lawyer who has never taken a psychology class, but maybe should to understand her affliction with plaids. She has been coaching unhappy lawyers on career change for a decade. You can email your question, or set up an individual consultation, by emailing her at


Get Out: Artist in a Lawyer Suit

Dear Jennifer,

I’m three years out of school. I lasted 18 months at my big law job, where they inexplicably placed me in IP litigation despite the fact that I’d never indicated any interest in IP law and had no experience in IP law.

I jumped ship with no plan, and miraculously landed in a federal clerkship lasting slightly longer than two years. I have less than a year left now and am panicking over what to do next. 

I thought I might go back to a firm for a year or so, but talking to a recruiter caused me to have panic attacks & sudden suicidal ideation.

I want nothing to do with the law. Just thinking about staying for a minute longer makes me feel endlessly hopeless. But I feel stuck because I don’t think I can find a job that’ll pay well enough to let me make the jump. I just bought a house (not brilliant, I know), and my partner and I combined have around 180k in student debt. 

woman in ombre suit napat-seang

Photo by Napat Seang on Unsplash

I was really good at law school, and I’m smart, but it was a terrible fit and an awful choice. I hate sitting in an office all day and doing what feels like nothing. I love the judge I work for, but the actual work I do feels like doing the same repetitive IRAC. I’m bored to tears most weeks. 

I’m an artist. I minored in studio art in college but gave it all up during law school. Six years later I picked it back up and the love for it is still there. I’m a good teacher. If either felt like a viable career option, I’d be gone in a heartbeat. But teaching requires another degree/certification, which I can’t afford, and even if it didn’t, there’s the 50%+ pay cut I’d be taking… and we all know about starving artists…

I just feel really stuck in this job and completely hopeless about my next steps. Am I doomed to go back to a firm? Is there no other way?

Artist in a lawyer suit

Dear Artsy,

There’s a lot to unpack here.

Usually, when my clients’ values/priorities are profoundly misaligned with law, it boils down to not having a good reason for going to law school. The common denominator is not knowing yourself well enough, and not believing enough in yourself.

That might sound accusatory and judgmental, but it’s not. Unhappy lawyers do not have the lock on lack of self-knowledge and confidence at the tender age of 21 or 22, when they choose law school.

That means at some point, you’re going to have to tune in to your actual wants, needs, and preferences.

There is no shame in recognizing that who you are and who you want to be is profoundly misaligned with any version of practicing law. Don’t let anyone gaslight you into feeling weak or ashamed because you “can’t cut it in law.”

Find Your Core Self

So who are you, really? What are you here to do “with your one wild and precious life?”

What I see from your letter is that art and teaching are some of the core of who you are. I doubt those are the only things; sometimes our dearest desires stay in hiding until they feel it’s safe to emerge.

What I’m NOT saying is you must therefore become an artist or a teacher. Instead, you need to look for jobs that include a significant dose of teaching and art.

Those functions won’t necessarily be found in a job title. You’ll need to dig.

Look Past the Job Title

Teaching, for example, can be a part of corporate training, of community outreach, or of grassroots activism—for starters. The key is to dissect job listings for functions that involve teaching and art/creativity.

curious gecko philipp-lublasser

Photo by Philipp Lublasser on Unsplash

Check out, a site developed by the Department of Labor. This ingenious tool lets you select a job family, and then drill down into specific jobs for types of skills and knowledge needed. It’s an idea goldmine!

Once you get an idea of a job type or industry, start looking for meetings where your possible new tribe congregates. If you like these folks and what they to do, get involved in one of their projects. Working together like that is a fabulous way to build really meaningful connections, and those are important for your career switch.

OMG I Have to Figure it Out as I Go?

Doubtless this all sounds fairly terrifying if you are the typical introverted lawyer. Start slow, but start. Accept that not every effort will pan out. It only takes a couple to pan out for this strategy to work.

If you want out of law, you’re going to have to join the majority of the workforce who live just fine without a predetermined career path.

Question Your Assumptions

Lawyers usually look for the magic ticket out, that one ideal job that will transform their career. Sometimes it works like that.

To make your leap from law work, consider taking on a couple different types of part-time work. Maybe assemble a mix of one thing that’s entrepreneurial and takes a lot of marketing and promoting, and another thing that is stable and predictable but might not pay all that well.

Be sure to research options for restructuring your student loan payments. A whole niche industry exists to help you make loan repayment possible without starving.

questioning guy andre-hunter-

Photo by Andre Hunter on Unsplash

More importantly, rethink every financial area of your life. What do you pay for now that you can do yourself/learn to do, with the extra time you’ll have? Or, that house you’re saddled with—can you sell it now? Can you rent it out while living somewhere cheaper? Is there part of the house you could convert into a guest quarters and rent out online?

What about driving for ride-sharing services, or finding something in other parts of the gig economy?

Before you say no, really question why not. If your deep-down answer is something like, “but what will _____ think?”, keep questioning. Those people aren’t living your life, so their opinions aren’t relevant.

Listen to That Shrieking Inner Voice

You’re going to need a little bit of courage and belief in yourself. But if the idea of doing whatever you dream up does NOT make you “have panic attacks and suicidal ideation,” surely they are worth trying?

Your soul and your body are screaming at you to run from law. Listen to that wisdom. Have faith in your creativity—aka problem-solving skills—and your ability to learn and be resilient. You got this.

Jennifer Alvey is a recovering lawyer who has never taken a psychology class, but maybe should to understand her deep obsession with craft supplies. She has been coaching unhappy lawyers on career change for a decade. You can email your question, or set up an individual consultation, by emailing her at

Get Out! Advice for Unhappy Lawyers

I’m an advice column junkie. One of my favorite ways to avoid tedious things like bookkeeping and administrative tasks is to read advice columns, especially any chat transcripts.

updated get out blog post sizeBut I’ve never found an advice column solely for miserable lawyers who want to leave law. Then it hit me—I could do that! After a decade of career coaching, a decade in publishing, and almost a decade in law, I have a few pearls of wisdom I can throw out there.

We can talk about things like:

  • Can I find a job that I really, truly like, which doesn’t require a vow of poverty?
  • What can I do? I don’t have any job skills except reviewing documents and writing research memos.
  • I don’t want to do anything I’m good at any more. HELP!
  • I’ve invested so much in law, I can’t just walk away. But I’m miserable. HELP!
  • How can I even put together a resume and hunt for a job when I can barely get out of bed most mornings?

My hope is that I can help people with their law career problems. In particular, I hope I get letters about problems that many unhappy lawyers share, and let all you unfulfilled/ unhappy/ miserable lawyers out there know that you are FAR from alone. You have lots of company, hiding behind (pasted on) smiles and (fake) enthusiastic attitudes.

Sending in Your Letter

This is the easy part:

Drop  me an email ( about what you’re struggling with in making a job or life change. 

Be as specific as possible. Include what you love and what you hate (cats, dogs, iguanas, working at a computer, coffee, tea, late nights, bingeing obscure British TV shows, early morning runs—anything and everything unique to you). The more specific you are, the better answer I can give.

I’ll post a question and answer at least monthly, or more often if the volume and interest warrant it.

Don’t worry that everyone will know it’s you! First and most importantly, I will only use pseudonyms, and any personally identifying information will be deleted or changed to protect the guilty and innocent.

Also, I’ve been coaching for a decade; trust me when I say that your struggle isn’t as unique as you probably fear. It’s important, definitely. But I strongly doubt that no one else has ever had similar experiences and feelings. And if I think something could identify you, I won’t include it, or I’ll change it.

I hope y’all are as excited about this column as I am!

Truth be told, I’m scared the response to this lawyer advice column is going to be crickets. I literally have no idea how it will turn out. I think this is what we call in coaching, “Feeling the fear and doing it anyway.” Gulp.

pale woman from mid-nose down, biting part of her lip and looking unsure and afraid

So here I go, stepping out of my comfort zone. Please join me there. (pretty please?)

Jennifer Alvey is a recovering lawyer who did all the right things—Top Ten law school, federal appellate clerkship, job in Biglaw—and hated just about every minute of it. She did like some of the people, though.
For the last decade, Jennifer has been coaching unhappy attorneys about changing their careers. In addition to advice columns and true crime shows, she also has a slight craft supply addiction problem. You can send letters, or set up a discounted sample session, via email at