Thrillable Hours:
Career Change, Fear, and Life After Law

When I quit my job as a corporate lawyer in 2008, I thought that I was taking a one year sabbatical to travel around the world. I never expected that this blog, something I started to keep my family and friends updated about where I was going, would turn into a bigger project, and eventually a new career. I also never thought I would be aggregating a ‘law after law’ case study series, to help people find alternative careers for lawyers.

I called the series Thrillable Hours — a play on billable hours, which I found hilarious (and non-lawyers found baffling) — and the fruit of my efforts are at the bottom of this page. I posed the same 5 questions for each former attorney to ask them how they saw the world today. The interview also asked each participant to provide advice for people seeking to leave the law. Where should they begin? How to navigate that kind of change?

But as Legal Nomads grew, I received more and more emails from lawyers and law students confused about what options existed for them with their background. Some were miserable, some were bored, others were just curious. My own leap into a much less structured career was one that fellow lawyers wanted to emulate or evolve from, and I built this resource page to help lawyers look for alternative careers, or reframe their education in untraditional ways.

Alternative Careers for Lawyers: Contents


Career Change and Facing Fear
Resources to Support a Law Career Change
Resources: Books and Articles to Support a Law Career Change
Case Studies of Life After Law

life after law: resources for alternative careers for lawyers

Life After Law: Career Change and Facing Fear

But the series wasn’t enough for my resources, 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 how to face them without letting them control me.

The 5 Questions to Ask yourself Before you Quit Being a Lawyer and Change Careers :

1. Most important one: what is your worst case scenario? 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.  This means asking yourself:

    • What scares you most about changing careers?
    • What do you gain most? This can be personality-based or lifestyle, or more.
    • What’s the worst case scenario if things go pear-shaped, 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. I have a draft rant on this topic, but until I hit publish see Cal Newport, who summarizes it well in his The Passion Trap essay.

While it may look like I did just leap into the unknown and say fuck it to the man, what actually happened is that I saved up to take a sabbatical. During that trip, this blog took off, I got offers for freelance writing, and a new career began to take shape. Because I did some risk assessment first, of the kind I am advocating here, I wasn’t in a panic when that happened.

A video version of that essay here:

2. Figure out what you could happily invest more time in learning how to do better. What can you become more of an expert at doing?

3. Figure out how good you would need to get in order to leverage that skill 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.) What is the skill level you need to be valuable enough for that bargaining power?  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?

4. What experts can help you grow those skillsets and aggregate more leverage? 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? 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.

5. 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.

How to Figure Out What to Do in Your Life? The Paint Drop Method from Taylor Pearson

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.

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 assists in finding alternative careers for lawyers

Part of Taylor Pearson’s Paint Drop Method

Resources: Books and Articles to Support a Law Career Change

COURSE: Leaving Law Behind with Casey Berman and Adam Ouellette

I started my Thrillable Hours series to inspire lawyers feeling deadened by their job options to find the courage to think more broadly. I created it to help with fear, career change, and life after law. Though I also had plans to make a full course to help lawyers take a leap, I didn’t get to finish it. Readers kept asking me to build one, but my health kept interfering.

Casey and Adam have built such a course, so I’m partnering with them to fix the pain point those readers have. Their “Leave Law Behind” course will help lawyers through the process of career change, if that’s what you are interested in. And it will also support you leaving the law in a myriad of ways, including by working through the blocking beliefs and self-sabotage that can get in the way. The course also offers students interview and résumé help, as well as connecting with fellow career-changers – all to allow lawyers to hone in on what alternative career is best for them.

Basically, if I can’t help you I feel that Adam and Casey can at Leave Law Behind.

The plan is to hopefully record a video interview with them, too, for Legal Nomads readers.

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.”
  • What Color Is Your Parachute? A Practical Manual for Job-Hunters and Career-Changers, by Richard N. Bolles (2017) Newly updated; Included in this section instead of above as 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. From Amazon: “This book covers both the practical and ethical considerations for lawyers taking a break in service for a variety of (voluntary and involuntary) reasons, including temporary leaves of absence, taking care of family, changing careers, disciplinary actions, and retirement.”
  • Given the rates of addition 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 / 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.
  • 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.

Blog Posts 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.)

Resources and Articles to Support an Alternative Law Job

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

Case Studies of Life After Law

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.