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 wasn’t looking for an alternative career, because I thought I’d travel then go back to being a lawyer again. I never expected that this website, something I started as a blog to keep friends, family, 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 rather products or services that my readers said they needed or wanted. I didn’t set out to identify pain points that I could fufill; it happened bit by bit, by listening to what they sought but couldn’t find online.

For example, I am celiac, and struggled to find safe food as I traveled. I didn’t write about traveling with the struggle of gluten free eating when I started writing in 2008, but over time as I mention this was a condition I had for many years, readers with the same disease wanted help for their own adventures. So I began to build translation cards to support them (and me!) on the road. Other projects followed, like hand-drawn maps of food (built because a reader asked for one for Vietnam, but couldn’t find it). And more! You get the drill.

With time I realized that my ‘sabbatical’ would actually be a very different life than I had anticipated.

Back then, digital nomads were just getting started. I became one without knowing the term existed, by following my stomach to the next destination and writing along the way. As the concept was still relatively unknown, former legal colleagues and clients worried that I was ruining my life by taking this big leap and feared that I’d struggle to find work when I returned.

These days, remote work has skyrocketed, and so has a more flexible outlook toward professional careers, even ones as rigid as the legal profession. A few years into my travels, I created a “life after law” series called Thrillable Hours. The title is a play on billable hours, and it features lawyers who took the leap out of private practice into a more alternative career. People with a legal background seem to find the title funny; non-lawyers do not.

In that series, I ask the same 5 questions to each former attorney to see how they interact with the world after leaving private practice. 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 readers have told me that they’ve been a source of advice for lawyers and students alike. More recently, I supplemented this series with the resource page you’re reading. I wanted to provide a framework for students or lawyers to ask the right questions in seeking out alternative careers, and rethink the skills that may be transferable from the law to something else.

The truth is, law school and subsequent lock-step private practice sets you up with a very rigid flow for legal practice. Though things are changing year over years, often we come out of law school with the plan to graduate, take the bar, do articling if in Canada or start working in the US, practice, make partner or go into a corporate counsel role, and retire.

Modern legal structures have leveraged technology to soften the inflexibility of this path, and with the continued rise of large language models and artificial intelligence this will only continue. I hope this page gives you more confidence to reframe your education and training and find work that gives you meaning.

What to do when you don’t want to be a lawyer anymore?

Let’s start with the best questions to ask when facing fear and changing careers. These are a great starting point to make a big shift, but also help in mapping out some of the boundaries or consequences of that choice.

I find writing by hand works best for me and I used a new notebook to start going through the questions below when I made the leap my self. But for those who prefer typing, that works too, of course. The crucial part is to set aside quiet time to think these questions through thoroughly.

1. Make ‘love it’ and ‘leave it’ lists

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. Remote work is more prevalent and hybrid jobs are common. Do you want something like that? Is commuting part of what’s stressing you out? What about having to dress for the job? If accounting for 6 minute increments and/or billable hours are too much to handle, would a position as a general counsel satisfy your work ethos more? Maybe it’s time for a change.

For some, however, the ‘I hate it’ list may truly be the nature of the legal work itself. Not everyone will fall into this category.

So the first thing I recommend is to truly, really take stock of what you like and dislike so that you can use this information as a foundation for the questions below.

2. Why do you want to leave your career as a lawyer?

This question goes deeper than a cursory ‘I hate it’ list like the one above. What I’m asking you to get at here is the why. Do you have a sense of dread every Sunday evening (if you weren’t working all weekend!) knowing work is ahead? Do you feel like your work isn’t hitting at the fulfilment you seek out of life? Have you had something happen in your life that reframed things or changed your perspective about what is most needed to be happy?

In addition to these kinds of questions, the two that I want everyone to ask themselves are:

• What scares you most about changing careers?
• What do you gain the most by making this shift?
• What do you want out of life that you’re not currently getting?

This analysis and thinking 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.

3. Is there an emerging field of law that excites you?

Using the questions above with a focus on what you like and dislike, are there any newer fields of legal practice that pique your interest?

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.
• Laws around cannabis or psychedelics, especially here in Canada where it has been legalized. Many jurisdictions are also decriminalizing and/or increasing access for medical cannabis, and some states and jurisdictions are also doing the same for psychedelics.
• 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. (See also the American Bar Association’s page on the evolving landscape of legal tech law in South Africa, Australia, India, and the UK.)
• Medical law and ethics, especially as medical technology is supplemented by AI.
• Technology law specific to large language models and how they are implemented, including what is legally permissible as the law scrambles to adapt to their proliferation.

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.

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

When readers who are not lawyers write me about career change and fear, I direct them to this question. A personal risk assessment helps give voice to the nebulous fears many people have, allowing them to be countered, minimized, or even dismissed. Or, sometimes this process yields consequences we didn’t even know may be an issue until we sat down to do the exercise.

The reason for doing this is that once we have a handle on our worst case scenarios and have ways to manage them, they become more manageable and less of a threat. 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 you quit and do something else, and then things go pear-shaped? This question relates to both the practical (money, location, etc) and the emotional.
• What skills do you have to mitigate that worst case from happening?

Despite what my career change may look like, I didn’t just leap to ‘follow my passion’ and turn my back on the legal progression. I made lists like these, of what could go wrong and how I could fix it, and what I could do if things fizzled out. While I never expected a new career, I wanted to make sure I knew what my ‘plan B’ would be if at the end of my sabbatical I was unsure of what to do next. So this risk assessment that I did pre-departure didn’t even factor in a new career in writing and ecommerce. It wasn’t within the realm of my possibilities at the time. Instead, I set out what skills I had and how I could be hired to utilize them. Doing so gifted me the mental space and freedom to make decisions about next steps 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.

Is there any shame in leveraging skills toward a non-dream job, if that allows you the flexibility to build a life you want? Absolutely not. 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 2025, 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:

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

Next up in this process is to 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, one that made it harder to figure out how to relax. Overall, though, my 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. The question should not be “what is the passion that I can follow?” It needs to be “what do I want to become more skilled in?” We all risk losing the shine if we just follow passion to career. Thinking about topics with the time and effort required to get skilled in them is more realistic.

So: are the thing you love things that you want to get better at, enough to flip them 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.

If you’re struggling to find topics to answer this question, another approach is to do a life audit and 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 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.

If that process of discerning your goals also 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 six 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!

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

Ok, you know what you like and don’t like. You understand what you want to get better at. You see what topics you can be an expert in without hating your life.

Now, you need to figure out how good you need to be so that you can leverage those skills to build the life you want that you identified qualities of earlier on. E.g the life I wanted was to work for myself, not other people; to not go into an office; to be able to eat as much street food as possible; and to learn as much possible each day. I therefore needed to get better at the skill of writing, enough to pitch for freelance work. Better at the skill of coding to make sure I could maintain my website. Better at the skill of public speaking, enough that I could charge a keynote fee. During my years of wandering, I kept trying to improve those skills to increase my bargaining power.

Unfortunately, my life got fully derailed in the process of continuing to deepen those skills — see below for more about my story. But the skills that I’d gained expertise in during my decade of round-the-world travel and writing served me well even when I became disabled. They were far more flexible than my legal skills, it tuned out, and when I could only work a very little bit each day they supported me and my new bed-bound state.

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?

Here is a graphic I made with some of the tasks you had as a lawyer, and how you can describe or recognize those skills when looking at job postings for a post-legal job:

7. 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 queries.

Looking at this question 7 helps map out a plan for moving your new life forward with less fear.

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

We identified our worst case scenarios above. So the next question to ask is: if you get there, then how can you interact with that spot and still keep yourself afloat?

Being stuck in a worst case scenario isn’t failure when it comes to this process. It’s simply a backstop for your fear, and a way to look differently at the risks you plan to take. Prior to my injury, for me, the worst case of working in the law — even if not as an associate again, contract work or consulting was still a much better case than doing nothing.

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.

Another type of analysis: the “Paint Drop” method

Even if you went through the long process to become a lawyer, you’re on this page because you may want a change. My friend Taylor Pearson wrote a post about how people can figure out what they should do with their lives, and how they can get better at it. 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?”

This is a more concise version of the analysis above, and one that may be more resonat to some of you. Pearson 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 refer 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.

A quick note about my story: a lesson in what ifs

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. My notebook of “what ifs” and questions is the backbone for this post.

Preparing took the form of the questions above, but also reading books and articles from lawyers who left the law. More importantly, it also let me focus on understanding what my fears were and then how to face them without letting them control me. As noted above, 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.

After a decade of travel and food, in 2017, a routine medical procedure left me disabled with a chronic spinal CSF leak. This condition means I can only get a few hours of ‘uptime’ per day to work, bathe myself, feed myself, and exist out of bed. Four repairs to fix the spinal CSF leak did not hold. And sadly, that meant my ‘alternative career’ as I knew it came to a quick end.

As I noted above, though, 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.

Becoming disabled to this extent also was a lesson in choices.

How would I have felt about my life had I not taken the leap to travel? I learned a big part of my condition presently is a genetic component I’d never heard of. Had I stayed working as a lawyer all that time and then gotten this sick, I’d have never lived the life I dreamed of. Losing my mobility and much of my identity was hard enough, but the grief would have likely been even worse had I never taken the risks I did.

I am not saying that you ought to simply quit and never look back. I followed the processes I mention on this page before I was ready to leave. However, I share my story because it is a lesson in what ifs. I got to travel and eat my way around the world for a decade, building a business I loved in the process. I don’t regret that one bit, but I know I’d have regretted it if I stayed in the legal field and then gotten sick.

Thoughts on the future of legal work

Pre-pandemic, there was some unpredictability in the future of legal work, but the combination of Covid plus technologic advances have shifted the landscapes of many professions, and the legal field is not exempt.

On one hand, the expectation of all-hours-availability has only risen: we have the technology to be connected to work anywhere, at all times. 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.

On the other hand, the role of lawyers and in-house legal teams is changing even more quickly than most anticipated as businesses move toward a digital environment propelled by technology — especially AI. At the same time, there is a lot of pressure to cut costs and be ‘efficient’ in work, and AI is filling those gaps with a speed that has surprised some in the profession.

GenAI and legal work

In a 2024 report about generative AI and the future of legal work from Deloitte, they note that the legal industry is standing at a genuine inflection point. In a survey of 43 major clients, 79% reported that GenAI will have a moderate to significant long‑term impact on how legal work is performed, and while 88% cited efficiency and productivity gains as the biggest expected benefit. 87% predicted adoption within 2–3 years.

Within their report, Deloitte notes that with transformative potential comes with some hurdles: most legal teams struggle to move beyond pilots to scalable impact, held back by data quality issues, resource constraints, and the need for robust AI governance frameworks to manage emerging legal, ethical, and regulatory risk. They nonetheless note that change will come, swiftly and soon.

Many law firms are already integrating tools like Harvey AI, Copilot, ChatGPT Enterprise, and internal platforms to rewire their workflows. This has cut due diligence time by 40–70% at firms like Allen & Overy, per a 2025 report on AI and UK legal practice. This efficiency is fuelling a shift away from billable-hour models toward value-based or subscription pricing structures that offer clients greater transparency and predictability.

As routine tasks fall to AI, lawyers will need to evolve into strategic advisors, focusing on high-impact legal analysis and client collaboration and other areas that AI can’t take over with as much expertise.

While transformative, the rise of AI in law is far from risk-free. Courts have penalized attorneys for citing fictitious cases generated by ChatGPT, including fines and AI-training mandates. Judges have even withdrawn AI-tainted rulings, flagging challenges around factual accuracy and court policies. Courts are not seemingly ready for AI-generated briefs or evidence.

In response, new professional guidance has emerged. The ABA released formal ethics rules in July 2024, stating that to ensure clients are protected, lawyers and law firms using GenAI must “fully consider their applicable ethical obligations,” which include duties to provide competent legal representation, to protect client information, to communicate with clients and to charge reasonable fees consistent with time spent using GenAI.

In addition, the EU adopted an Artificial Intelligence Act, which classifies AI according to risks ranging from unacceptable (which are prohibited uses of AI under the act), to high-risk (which are regulated), and minimal risk (currently unregulated and will remain so under the Act. The majority of obligations in the Act fall on providers (developers) of high-risk AI systems, including third country providers where the high risk AI system’s output is used in the EU.

Where to from here?

The historical rigidity of the legal profession is bumping up against technology in fascinating and disruptive ways. With companies offering subscription-based contract tooling, AI training, and blended client services that straddle law and tech, and firms themselves training and developing systems based on AI, there is significant change afoot.

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.

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.”

Articles about fear and resilience

• Tim Ferriss’ Fear Setting exercises, with good questions to ask before undertaking decisions you’re afraid of. Bonus: the interview is with Hans Keeling, a former lawyer.
• Strategies for Overcoming Fears of Change and Failing FindLaw (This is an excerpt Career Change: Everything You Need to Know to Meet New Challenges and Take Control of Your Career, by David P. Helfand)
• How can I face my fear of making a career change? A list of questions relating to fear.
• Five Science-Backed Strategies to Build Resilience. 12 of resilience practices (squeezed into five categories), which can help you confront life changes more skillfully. Building resilience through mindfulness and habits is an excellent backstop to career transition, as it allows you to act from certain place, one less clouded by fear.

(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:

In Canada

• For Canadians, careers at the Department of Justice are an option if opting out of private practice is the main concern.
• The Canadian Bar Association’s alternative careers page, with their publication The National also hosting a long page about alternative careers, including skills that are transferable to other professions.
• The Ontario Bar Association also has a page on alternative careers for lawyers.
• Simon Rollat’s piece about alternative paths in the Canadian system. Simon runs DALA, an alternative careers group at my alma mater, McGill University. The piece also quotes from Dean Robert Leckey (who was in my year at McGill) about a non-traditional path.
• Life After Law: What to Do When You Don’t Want to Be a Lawyer Anymore, by fellow McGill grad Devo Ritter.
• Alternative careers for lawyers (PDF) from the Skilled Immigrant Info Center, specific to the province of British Columbia
• University of Toronto in Mississauga also has a long (44 page) PDF about alternative careers for lawyers, here.

In the United States:

• Georgetown Law’s alternative careers page.
• The Advocate’s list of high paying alternative careers with a law degree.
• The American Bar Association’s (ABA) career center made a 2017 video about career changes and alternative tracks for lawyers.
• The ABA also has a landing page for alternative careers for lawyers, here.
• Life After Law’s job board.
• Get Educated has an alternative careers page with salary listings, focusing on high-paying alternatives (America-focus).
• Pepperdine’s alternative jobs for law school graduates page, here.
• For those who want to make a lateral move to a non-firm environment, Corporate Legal Operations Consortium (CLOC)’s job board includes a lot of general counsel work.
• University of Toledo’s list of resources for nontraditional law careers options.
• Loyola University School of Law’s alternative law careers resources page (several resources in here).
• Work-as-An-Attorney-from-Home job suggestions from an American perspective.
• National Associates for Law Placement has a few PDFs of note, including on emerging legal jobs (2015). The others are here.
• “Alternative Uses for Your Law Degree” – article from the Missouri Bar Association.
• Marc Luber’s JD Careers Out There site has an alternative careers for lawyers page with some of the obstacles that attorneys may feel hamper them from taking the leak.

Generally and internationally:

• Cambridge University (UK) has a 22 page alternative opportunities for lawyers PDF with a specific EU and UK focus.
• Chambers, a UK company that aids studies and lawyers research law firms and law schools, also has an alternative careers page, here. Emphasis on UK opportunities.

• Escape the City’s job listings board for many alternative careers that don’t involve a fixed location.
• From a different perspective: someone who opted to become a lawyer at later in life.
• Also from a UK perspective, All About Law’s alternative career’s page here.
• And a less conventional route: a US-based lawyer who quit to start her own Only Fans page—and now makes more money than she did as an attorney, and says she is happier too.

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. 

• I wrote a piece in 2015 on Redbook about why I quit my job to travel, and what to think about if you are considering doing the same.
• Simply Sweet Justice has a long, loooong list of lawyers who are now bakers here. Seriously, there are a LOT of lawyers who became bakers.
• Above the Law’s Alternative Careers page.
• New York Times recently featured Rob Friedman, former lawyer who became a baseball pitching “whisperer” and adviser. “People have come up to me to get my autograph,” Friedman said. “I’m like, what the hell is that? I’m a freaking lawyer!”

Thrillable Hours: my interview series with lawyers who changed careers

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.