Thrillable Hours: Alternative Careers for Lawyers, Fear, and Life After Law

When I quit my job as a corporate lawyer in 2008, I planned to take a one-year sabbatical from the law to travel around the world. I never expected that this website—something I started as a blog to keep family, friends, and former colleagues and clients updated about my adventures—would turn into a bigger project, and eventually a new career.

That career change came thanks to technology and the creator economy; my income sources were not ads or sponsored content, but products or services that my readers said they wanted. I kept this site ad-free and turned down free travel. Instead, I built celiac translation cards for restaurants, hand-drawn maps of food, and and ran local “food walks” to accompany readers. With the exception of freelancing or public speaking opportunities I took on, I created income streams that were uncoupled from my day to day life, which allowed me to keep eating the world.

Over the years, I have received many questions about my journey from BigLaw to soup eater. I ended up creating a “life after law” series called Thrillable Hours, a play on billable hours, all about lawyers who took the leap out of private practice. (We found the title funny; non-lawyers did not.)

In that series, I asked the same 5 questions to each former attorney to ask them how they saw the world today. The interview also focused on advice for for people seeking to leave the law. Where should they begin? How to navigate that kind of change? These interviews are at the bottom of the page, and have been a great source of advice for lawyers and students alike.

As Legal Nomads grew, the “help I want to leave the law!” emails increased. My own shift into a much less structured career was one that fellow lawyers wanted to emulate or evolve from. So in addition to my interview series, I built this resource page to help you look for alternative careers, or reframe your education in untraditional ways.


Table of Contents

Thoughts on the future of legal work

Pre-pandemic, that unpredictability was there but the current landscape has only added to the expectation of all-hours-availability, even when working from home during lockdowns. So it comes as no surprise, then, that I have received many more emails about leaving the law in the last few years than in the decade preceding it.

As the pandemic ground on, lawyers started looking for ways to strike a better balance between work and family. A June 2022 Above the Law article notes,

While the legal profession is seemingly driven by big salaries and big brand recognition, over the past two years, many lawyers have openly discussed trading in the higher salary and the bragging rights of being in Biglaw or working for big name companies in exchange for more time with their families, fewer hours commuting, and a better corporate culture that honors those priorities. This means compensation or extra PTO just isn’t enough for those desiring a better quality of life.

Now that some companies are trying to encourage a return to the office, the legal profession is split. Per a 2022 ABA survey report called “Where Does the Legal Profession Go from Here?” (pdf link), 44% of lawyers that have practiced for under ten years would jump ship from their firms/companies if they received a job offer that allowed for remote work. In contrast, only 13% of lawyers practicing long-term said the same.

Where to go from here? Firms that refuse to consider flexible work may be the ones to lose out. “Companies that are trying to drag back time will lose some of their best talent, and that dynamic will force these companies to catch up,” says Raj Choudhury, in a piece about how the “work from anywhere” war is just beginning”.

For lawyers, however, dissatisfaction goes beyond flexible work. The 2022 ABA study paper also reported on a growing number of lawyers who want more work-life balance. It’s what I’ve said since I quit my job in 2008: that happiness is not contingent on monetary compensation alone, and that success does not only mean career advancement. In old age when we look back on our lives, it is unlikely that we will say, “damn, I wish I billed more.

The truth is that “BigLaw” can be a very harsh environment, even when we knew what we were getting into. Per a Business Insider piece from 2021,

“The hardest part about this job isn’t necessarily the long hours. It’s the unpredictability of the long hours. What looked like a free weekend or free night can quickly turn into an all-nighter. You quarantine for two weeks so you can see your parents, and, as much notice as you give, as much as you prepare for it, the realities of what you’re being paid for is that that can blow up at any moment.”

If working as a lawyer but doing so remotely interests you, please see my Resources for Digital Nomads and Remote Work page as well. I’m referring to “working from anywhere” not just “working from home”. The historical rigidity of the legal profession likely means that embracing long term remote work is unlikely. It’s a shame, because there are many extremely talented people who now want that kind of work environment.

For those who want to change careers, hopefully this page provides some guidance, comfort and help to figuring out what “success” looks like for you in the context of being a lawyer. Whether that means a hybrid work environment, leaving the law altogether, or trying something new, this era in the legal field is one where more avenues than ever seem possible.

Please do feel free to use the contact form and reach out if you have questions that it does not answer.

Life after law: what to do when you don’t want to be a lawyer anymore

My “life after law” series wasn’t enough as resources go, because while case studies are helpful most of us need something more constructive. Personally, before I quit my job as a lawyer I focused on checklists and preparedness—stuff that helped me feel a bit safer in my decision to turn my back on being an attorney.

Preparing took the form of reading books and articles from lawyers-turned-whatevers, but more importantly to focus on understanding what my fears were and then how to face them without letting them control me. This meant setting up “plan B” if my initial decision didn’t pan out, but it also meant thinking long and hard about life goals and the meaning of work.

A quick note about my story

In 2017, a routine medical procedure left me disabled with a chronic spinal CSF leak. Sadly, that meant my alternative career in travel and food came to a quick end. But the benefit of my business model paid off: I was able to shift focus and write more about chronic illness here on the site and on social media, and have been able to help raise awareness for my condition via freelance pieces in the process. The celiac cards and maps continue, and I also started a Patreon monthly membership where readers can support me since I cannot work like I used to because of the ongoing spinal CSF leak.

I mention all of this because one of the main fears in quitting a traditional, lock-step career like being a lawyer is that if life changes drastically there is nothing to fall back on. While my journey has never been conventional, the systems, communities, and projects I built prior to becoming disabled still support me today. That can be the case for anyone.

The best questions to ask when facing fear and changing careers

These are a great starting point to make a career shift, but also help in mapping out some of the boundaries or consequences of that choice.

1. The most important one: why are you leaving your career as a lawyer?

Before choosing to leave the law, it’s important to sit down and make two lists: a list of what it is that dissatisfies you with your current job, and a list of what you enjoy. The “I hate it” list may be long, and it may be very easy to write; many a disgruntled lawyer has no problem providing a litany of things that they dislike about their profession. But for some, doing this exercise may spotlight ways that they can still work within their profession’s limits, but in a more appealing way.

For example, in the age of COVID, office work is not the default everywhere. If ‘commute time’ or ‘dressing up for work’ is on that list, perhaps a remote position may fix that problem?

If the billable hours are too much to handle, would a position as a general counsel / in house work satisfy you instead?

For some, the issue may truly be the nature of the work itself. Not everyone will fall into this category. So the first thing I recommend is to truly, really take stock of what you dislike.

Ask yourself:

  • What scares you most about changing careers?
  • What do you gain the most by making this shift? This can be personality-based or lifestyle, or more.

Then, move onto what you like. If you feel convinced that you do not want to be a lawyer anymore, turn to your “likes” list. This will give you a thorough map for what you need to look for as you move into a new career or job, and makes the process less overwhelming.

2. Is there an emerging field of law that would work instead, and help you feel like you’re working on something exciting and different?

With both the rise of remote work and actual “legal nomads” (as opposed to me, who quit law practice to focus on the “nomadic” part), there are some shake ups in the legal industry. Opportunities to work as a lawyer in unconventional ways are increasing daily.

There are also new opportunities to work in emerging fields of law that did not exist when I was in practice or in law school. Fields like:

  • Blockchain and cryptocurrency laws & regulations, whether related to taxation or otherwise.
  • Cannabis laws, especially here in Canada where it has been legalized. Many jurisdictions are also decriminalizing and/or increasing access for medical cannabis.
  • Geomatics and other spatially-referenced or location information, like LIDAR, drone use, and more. One of my favourite courses was international air and space law, something I would interested to go back and study now with the current landscape.
  • Advertising and technology law, which includes false advertising, gaming, apps, and intellectual property. This was the area of law I practised in during my last years, and it was really interesting. Likely even more so now with the widespread use of new technologies.
  • Medical law and ethics, especially as the pandemic continues.

These areas may not interest you, but for those who aren’t fully ready to leave the law they may provide a lateral move that keeps you excited to learn each day. If that’s the case, perhaps it’s worth exploring first.

A resource to help you figure out what this sweet spot may be is Design your Delta, a site that offers some brainstorming help via the existing “Delta Model”. The Delta Model goes through three areas that can be helpful to examine for lawyers seeking change: practice area, people, and process itself. You can read more about their model here. I have not engaged in their toolkit/process myself, as I am now very far away from the practice of law, but others I’ve recommended it to have found it helpful. (I have no affiliation at all with the Delta site, for clarity!)

Via Design Your Delta

3. What is your worst case scenario after you quit your job as a lawyer?

When readers who aren’t lawyers write to ask me about career change and fear, I often go back to this series of questions about risk assessment. Once you’ve got a handle on worst case scenarios, your fears eclipse a lot less of your heart and mind. 

To get to your worst case scenario strategy, you need to sit down and think though some some tough fact patterns to get to the heart of your career change.

As yourself:

  • What’s the worst case scenario for you if things go pear-shaped, for your life or emotional state?
  • And (this is important!) what skills do you have to mitigate that worst case from happening?

I’m not of the “find your passion and take the leap” school of thought, despite my trajectory from BigLaw. While it may look like I just leapt into the unknown and said fuck it to the man, what actually happened is that I saved up to take a sabbatical because of a love of travel. During that trip, this website took off, I got offers for freelance writing, and a new career began to take shape. I did some risk assessment first, of the kind I am advocating here, and it allowed me the kind of mental space and freedom to make ‘next step’ decisions based from a place of calm analysis and not unprepared panic.

In an April 2021 piece called, Dream Jobs Are a Myth, and More Wisdom From ‘An Ordinary Age’, Rainsford Stauffer writes about the pressure to find one’s purpose. The piece is in Teen Vogue, so it’s geared at a younger audience, but this paragraph stood out:

[I]t feels backward to define ourselves by what we do anymore, as if job titles are status symbols and dream jobs don’t incite their own version of turmoil: What if everyone else knows their dream job, their calling, their purpose, and you don’t? What if you end up unable to get a job in your chosen field, or get your dream job and realize it’s not at all what you want? When these notions get encouraged in young adults, it feels like undercutting more realistic expectations around what work is, and how it feels. Maybe if so many of us weren’t only focused on defining ourselves by dream jobs, it would give us freedom to reimagine our meaning, purpose, and what matters to us in other facets of our lives.

As technology has changed, as more and more work moves online, finding work as a digital nomad or remote worker becomes more feasible. Is there any shame in leveraging skills toward a n0n-dream job, if that allows you the flexibility to build a life you want? I don’t think so. BigLaw’s ruthless hours and punishing schedule are part of why it private firms remain a difficult structure to ever change your life in the ways you want. But in 2021, there is a lot of room for creative legal work, or non-legal work, that isn’t a “total dream” in terms of day-to-day but does give some financial comfort and a much less restrictive schedule.

Cal Newport summarizes this conundrum of ‘dream jobs’ well in his The Passion Trap essay. A video version of Cal Newport’s essay below, for those who prefer it:

4. What can you become more of an expert at doing? What do you want to become more of an expert at doing?

Figure out what you could happily invest more time in learning how to do better. This is a great “brain dump” kind of exercise to truly examine what kinds of skills become stale when you contemplate deepening them.

As a travel writer, I did for work what most people do for vacation. This left me with a very different relationship to travel, but overall working on the writing skills, editing, photography, and public speaking did not curdle the joys of travel. It meant I needed to rethink how to relax, but travel remained a joy for me.

Is the thing you love something you want to get better at enough to flip it into a career? Or are there skills you have that you can deepen, broaden, become additionally certified in that you can use to change your law career into something different. Had I decided to focus primarily on writing without the travel, I could have become a freelance writer, fiction or otherwise. But the thought of becoming more of an expert on writing itself did not sit well; ultimately I opted for the area that working on my skills ad nauseam didn’t make me, well, nauseous.

Another way to approach this question is to do a wholesale “life audit”, to brainstorm the values and goals you have and how they align with both your dreams and the timeline that you hope to attain them. The life audit process lets you dream “mondo beyondo” dreams (all the things you might not have put to paper prior), then helps you reorganize them alongside your values and your life plans so that patterns can emerge.

I’ve found that getting all of these thoughts “out” and on paper (or post-it notes, as the process below suggests) truly helps lift a weight off. Doing so also let me be more creative (skydiving instructor? really?) and detach from the expectations of others as I thought through my own trajectory.

So what is a life audit? Author Ximena Vengoechea describes at as:

An exercise in self-reflection that helps you clear the cobwebs of noisy, external goals and current distractions, and revisit or uncover the real themes & core values that drive & inspire you. Also known as: spring-cleaning for the soul.

Ximena sets out step by step instructions for a life audit here, which will require at least 100 post it notes, a few hours of your time, and a dedication to your imagination.

Current time spend vs. desired time spend, from the life audit process, useful for lawyers looking for an alternative career.
An example of a chart from Ximena’s Life Audit process, of current time spent vs. time desired for a specific area of life.

If that process of discerning your goals doesn’t feel like a good fit for you, another option is to follow the “What Do You Actually Want?” process from Adam Westbrook.

He suggests five steps, including the following:

  • Disconnect from social media: self evident, no need for me to elaborate!
  • Reconnect with your entitlement: by this he doesn’t mean the “do you know who I am” kind of entitlement, but rather the core of who you really are BEFORE people got to you and started molding you into who they wanted you to be. You have “as much right to reach for you want as anyone else,” says Westbrook. Reconnect with what that may be.
  • Answer the question, “what do I really want” every day: he suggests that consistency is key, doing so every day for at least a month. What are the patterns that emerge? 
  • Write your future Wikipedia page: Everyone has a different way of visualising success, and writing your future Wikipedia page is a bit less morbid than the often-suggested “write your own obituary.” Maybe it’ll spark some new ideas for your future!

5. What skill level do you need to be valuable enough for the bargaining power you want?

Ok, you’ve got expertise down pat. Now you need to figure out how good you would need to get at those things in order to leverage them to build the life you want to build.

For me, this meant working for myself, not going into an office, and being able to eat as much street food as possible.

In a piece about law practice in 2019, Mark Cohen interviewed a 1L who noted, “I regard law as a skill. I plan to leverage my legal training and meld it with my passion for business, technology, and policy. For me, law is not about practice.”

What skills can you leverage too?

6. What experts can help you grow those skillsets and aggregate more leverage? What professional support is available to get you there?

In today’s digital world, access to experts and their knowledge has never been easier. Who can you engage with to double down on your skills? Who can provide a snapshot of their own path to better inform you own? This includes professionals within the emerging legal fields I highlighted above. The more info gathering you can do on a one-to-one level, the more you will be to make an informed decision.

Approaching people in a quiet way – not “here are some times for a call” but rather “I’d be grateful if you could spend a few minutes of your time helping me understand your trajectory” – goes a long way toward answering your questions.

7. How can you ‘fall back’ on your worst case scenario in a graceful way?

For me, the worst case of working in the law, even if not as an associate again, was still a much better case than many. Think about what happens if your shift in careers does not work out. Is the ‘worst case’ you’ve established something you can’t see yourself doing at all? If so, you need to reframe things and figure out a better, more palatable means of returning to some form of stability before you set out. It goes a long way toward grounding you in confidence before you take that leap and leave the law.

The “Paint Drop” method to figure out what to do after leaving the law

My friend Taylor Pearson wrote a post in April 2019 about how people can figure out what they should do with their lives. Even if went through that process to become a lawyer, you’re on this page because you may want a change. Among his advice is to keep asking yourself important questions, such as “what do you do well?” and “what do you find interesting?” while seeking a Venn-diagram overlap between the two and the very important question of “what will people pay for?”

To do so, he focuses primarily on skillset, because it is your unusual  knowledge that will set you apart in today’s world. Taking a rare skill and combining it with a creative application is far more important than simply fitting into an existing mold.

I referred to this as the sweet spot between your wants, your skills, and the pain points out there that need to be solved.

Per Taylor:

What is valuable today is not learning how to be normal or common, but the opposite: developing a unique, uncommon skill set that is in high demand. The internet has massively broadened the possible space of careers by allowing you to scale almost any niche obsession or interest. The fundamental property of the internet is that it connects every human on the planet to every other.

Check out his full piece here to try the Paint Drop Method for yourself.

paint drop method helps you drill down on the best jobs for lawyers leaving the law
Part of Taylor Pearson’s Paint Drop Method
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Books and articles to support a career change

Books about alternative careers for lawyers

  • Life After Law: Finding Work You Love with the J.D. You Have, by Liz Brown (2013). Book summary: the book” provides specific, realistic, and honest advice on alternative careers for lawyers. Unlike generic career guides, Life After Law shows lawyers how to reframe their legal experience to their competitive advantage, no matter how long they have been in or out of practice, to find work they truly love.”
  • The Unhappy Lawyer: A Roadmap to Finding Meaningful Work Outside of the Law, by Monica Parker (2008). Book Summary: “The Unhappy Lawyer will help you uncover exciting alternative careers with a unique step-by-step program that will make you feel like you have your very own career coach. With chapters containing real letters from lawyers who are desperate to leave the practice of law, tales from lawyers who have shut the door on their legal careers, and powerful exercises.”
  • Leaving Law: How Other’s Did It and You Can Too, by Adele Barlow (2015. Note, I worked with Adele at Escape the City). Book Summary: “This is the ultimate companion for lawyers who want to escape their profession but are sceptical about career counsellors. It is based on years of experience helping hundreds of confused lawyers at Escape the City, a community of motivated corporate professionals who want to do something different with their careers.”
  • The Official Guide to Legal Specialties (Career Guides), by the National Association of Law Placement (2008). Book Summary: “An inside look at what it’s like to practice law in 30 major specialty areas, including appellate practice, entertainment, immigration, international, tax, and telecommunications. This book gives you the insights and expertise of top practitioners-the issues they tackle every day, the people and clients they work with, what they find rewarding about their work, and what classes or work experience you need to follow in their footsteps.”
  • 24 Hours with 24 Lawyers: Profiles of Traditional and Non-Traditional Careers, by Jasper Kim (2011). Book Summary: “This book gives you a unique “all-access pass” into the real-world, real-time personal and professional lives of twenty-four law school graduates. These working professionals each present you with a “profile” chronicling a typical twenty-four-hour day in their traditional and non-traditional careers.”
  • The Law School Alternative: The shorter, more affordable path to a law-related career, by Jolene Blackbourn. This book is an interesting read if you’re thinking of law school, but not sure if it’s the right move. It runs through alternative education paths within the legal world, but not dependant on a pure JD.
  • What Color Is Your Parachute? A Practical Manual for Job-Hunters and Career-Changers, by Richard N. Bolles (2022 Edition) Newly updated, and included in this section instead of of the general career change books since this is the world’s most popular job-search book.
  • The Creative Lawyer: A Practical Guide to Authentic Professional Satisfaction Paperback, by Michael F. Melcher (2007). Book Summary: “Starting with self examination, readers will be able to analyze their personal values and then create their own personal fulfillment plan. Create a step-by-step plan for life and career that will get you back on track with your personal definition of happiness with this important book.”
  • The new ‘What Can You Do with a Law Degree?’ book, by Larry Richard (2012). Note: more expensive textbook pricing for this book. Book Summary: “This book contains career exercises, practical career-finding techniques, and a compendium of 800+ ways to use your law degree inside, outside or around the law.”
  • Lawyer, Interrupted: Successfully Transitioning from the Practice of Law–and Back Again (2015), by Amy Impellizzeri. A good read for both the practical and the ethical considerations of leaving the law. What I like about this book is that it doesn’t only address people leaving because they want to, but also those practitioners who have to leave for life reasons, for example leaves of absence, taking care of family, retirement, and more. A useful book that covers a wide variety of circumstances.
  • Given the rates of addiction and depression in the law (see Vice Mag’s anonymous piece here), I wanted to also include Brian Cuban’s The Addicted Lawyer.

Books about career change and finding creativity

  • The War of Art: Break Through the Blocks & Win Your Inner Creative Battles, by Steven Pressfield. I’ve found creativity and fear are two sides of a very similar, shiny coin. This book helps you get more comfortable with that gnawing fear of impending change, because (as Pressfield argues) that fear is actually a very good sign — it tells us what comes next. The more scared we are of what we are excited about work-wise, the more we need to give it a shot. Instead of being held back by that deep, powerful resistance, Pressfield tells us to face it head on.
  • The ONE Thing: The Surprisingly Simple Truth Behind Extraordinary Results, by Gary Keller and Jay Papasan. I’m including this one because lawyers have a good, trained tendency to focus on all of the aggregate problems or obstacles – it’s what we’re paid to do, after all. But in times of change, you need to reframe with narrower focus so as not to drown yourself in anxiety. The premise is simple: in a world with dizzying amounts of options and distractions, those who can focus will achieve meaning and depth that is unparalleled.
  • Own Your Career Own Your Life: Stop Drifting and Take Control of Your Future, by Andy Storch. I’m including this book because the mindset we often find ourselves in when we are feeling “stuck” ends up simply grinding us further into the mud. The book helps plan actionable steps to get out of that rut, and get in touch with how you want to live your life less clouded by the (understandable) resistance that feeling stuck lets fester.
  • Designing Your Life: How to Build a Well-Lived, Joyful Life, by Bill Burnett and Dave Evans. The premise of the book can be boiled down to: when we get mired in problems that seem unsolvable, we need to reframe our relationship to them and try again. The book gives you tools to do that, and ways to craft a life that is fulfilling and meaningful regardless of our myriad backgrounds. While personal mindset matters most, the I found the book interesting at providing practical ways to rethink big problems like “what is the life I want to lead?”
  • Take the Leap: Change Your Career, Change Your Life, by Sara Bliss. Case studies of people who have made unconventional career changes, transforming their lives in the process. They aren’t all lawyers – there is, however, one lawyer who went from billable hours to surf instruction – but the interviews are interesting and the wisdom inspiring from entrepreneurs, writers, artist, athletes, and more.
  • Pivot: The Only Move is the One You Make Next, by Jenny Blake. This book is — as the title would suggest — all about the pivot, a startup term that can also apply to changing our lives. Blake, a public speaker and career coach, aggregates her advice about taking small steps to move in new directions and modify goals and careers in the process. Actionable and interesting.
  • How to Be Everything, by Emilie Wapnick. Having a lot of different interests, projects and curiosities is something I was told “makes you an all-around gymnast – not a gold medal winner. Wapnick, who studied law at McGill University, argues that the narrowed experience theory is an outdated one. Instead, she urges people with many creative pursuits (multipotentialites, in her words) to leverage that diversity and passion as their biggest strength. The book teaches you how to build a life that you love, not because you ‘follow your passion’ but because you come into who you really are – which allows you to find meaning in whatever work you do.
  • For a bit of spirituality braided in, see Design the Life You Love: A Step-by-Step Guide to Building a Meaningful Future, by Ayse Birsel. It’s an interactive journal – which may not appeal to all of my readers! But if doodling and listicles help you think stronger, this may be a good start for getting a better handle on changes you want to me.
  • Big Magic: Creative Living Beyond Fear, by Elizabeth Gilbert. Some may argue that this book belongs elsewhere but I firmly believe that entrepreneurs and changemakers need to have a strong and brave creative streak, and this book speaks directly to creative pursuits in a linear world.
  • Seth Godin’s Linchpin, about making yourself indispensable in creating new businesses and products, and Purple Cow, about transforming your business to make it remarkable, are both highly recommended. From Linchpin: “Your art is what you do when no one can tell you exactly how to do it. Your art is the act of taking personal responsibility, challenging the status quo, and changing people.”
For more books and resources relating to entrepreneurship and location independent work, please see here.

Articles about fear and resilience

(For those not seeking a change at the moment, check out Associate Mind’s long list of online resources for new lawyers, from books to articles and much more, as well as Hastings College of Law’s New Models of Legal Practice publication.)

Articles about alternative law jobs

There are also a few other sites around the web that provide resources for lawyers seeking a career change:

Case studies from former lawyers

Before I quit my job as a lawyer, I found it really helpful to read through case studies and details from former lawyers. This both bolstered my courage, but also showed me how many others have taken the leap and landed on their feet. It’s a daunting prospect in a career that tells you that lock step salaries and billing units are the absolute norm. It’s a lot harder to think of something different when you’re exhausted and everyone else is keeping their eye on the prize they want: partnership. But making partner isn’t for everyone. It wasn’t for me, and it wasn’t for the people below.  Hopefully these former lawyers give you more encouragement and steps to think a little differently about your life and what it can hold. 

Thrillable Hours: my interview series with lawyers who changed careers
alternative careers for lawyers case studies
Case studies below!

I hope this series is helpful. I know I have learned a lot from the interviewees, and look forward to continuing to interview and highlight these smart and interesting people.

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