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 law after law case studies, to help people find alternative careers for lawyers.

As the site 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 started to include resources for those who are restless in their fields of law.

Alternative Careers for Lawyers: Where to Begin

resources for alternative careers for lawyers

I started these resources with a Q&A series on alternative careers for lawyers, one that used 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?

I called it Thrillable Hours, a play on billable hours, which I found hilarious (and non-lawyers find baffling). You can find those interviews at the bottom of this page.

On 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.

Questions to ask yourself: 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 pearshaped, 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, I wasn’t in a panic when that happened.

The  most important parts of that process were:

  • Figuring out what I could happily invest more time in learning how to do better / become more of an expert at doing.
  • Figuring out how good I would need to get in order to leverage that skill to build the life I wanted. (For me, this meant working for myself, not going into an office, and being able to eat as much street food as possible.)
  • Continuously trying to learn from experts about growing a business that was new to me.
  • Understand what my worst case was (for me, becoming a lawyer again – which is still a ‘better case’ than many).

Resources for Career Changes and Facing Fears

  • 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?”
  • 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.
  • For a bit of a woo woo option, 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.

(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.)

Resources and Articles for Alternative Law Jobs

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

Books for Non Traditional Law Careers

Case Studies

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.