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Above The Law


The following post was written by Leave Law Behind reader, Chris Jones, formerly of Cadwalader Wickersham & Taft and now VP of Content for AppointmentCore, a scheduling automation software company.

Take it away Chris …

Every year, I try to do something that scares me.

In 2011, that meant jumping off the world’s highest bungee bridge in South Africa.

In 2012, I put on a parachute and jumped out of a plane.

In 2013, feeling that my fear of heights was more or less conquered, I turned inward and focused on something that’s always been scary: saying no.

Last year, in 2014, I confronted my fear of vulnerability and performed 10 minutes of stand­up comedy.

This year’s challenge was something just as scary and just as rewarding: leaving the law behind. While each of these personal challenges of the past five years presented a new fear ­and a new opportunity for growth, ­both bungee jumping and leaving BigLaw especially reinforced my understanding that fear is illusory and that big challenges can only be conquered through small steps toward a goal.

I’ll never forget the feeling I had when I saw the Bloukrans Bridge for the first time and gazed down to the sleepy river below­­ 708 feet, 8 inches below to be exact. At that moment, the task felt insurmountable. As I sat on the canyon’s edge and looked across at the bridge, I had a clear realization: the only way I to conquer the bridge was to take small, manageable steps. So that’s what I did.

Step one: buy the ticket.

Step two: strap on the harness.

Step three: walk across the bridge to the staging area.

Independently, these were all reasonably easy steps to take. And while none of them required any real fortitude or courage, each step brought me just a little bit closer to the edge.

Pretty soon, the queue disappeared and it was my turn.

Step four: strap on the cord.

Step five: walk to the edge.

As I shuffled out, I heard something unexpected. The man who strapped the cord to my legs said, “Remember brother, you’re in the safest place in South Africa. Millions of people have jumped and no one has been hurt.”

Just like that, the fear vanished. I put my hands in the air and shifted my weight forward.

Step six: take the leap.

The freefall only lasted about 10 seconds, but it was the most beautiful, most peaceful, and most exhilarating 10 seconds of my life. The adrenaline heightened my awareness of all around me: the rush of the river below; the songs of the birds in the canyon; the tension from the bungee cord against my legs. I waited in blissful silence, bouncing up and down, until the crew hoisted me back up to the bridge.

“That was the greatest thing I’ve ever done,” I tell them. “I feel like I can do anything!”


Leaving the law was a lot like jumping off that bridge. Once I decided to leave, I was overcome by fear, anxiety, and frustration at the task ahead. But once those feelings settled, I realized that the same principle that facilitated my bungee jump applied here. With small, manageable steps, I could take the leap.

Step one: envision the life I wanted.​

I invested the time and energy to really think about how my personality, work style, skills, talents, and interests would align within a different professional environment. I discovered that I was drawn to entrepreneurship, start­ups, and early­stage businesses. I liked working in collaborative environments. I liked the creative process required to build a business. And I liked knowing that my professional trajectory was tied to my ability, not my years spent in the profession.

Step two: forget about the money.​

I had to let go of the anxiety and fear surrounding both my paycheck and my student loans. Once I realized that there was no correlation between the size of my paycheck and the size of my happiness, the inevitable pay cut became just more more small, manageable step. I also accepted that while it might take me a bit longer to pay off my student loans, I will not have to sacrifice some of my best professional years working in a job that was misaligned with my talents, interests, and values.

Step three: network.​

Once I focused on a professional path and prepared myself mentally for the change in financial circumstances, I got to work. I reached out to friends. I asked them to introduce me to their friends. I found mentors. I went to happy hours and meet­ups with other entrepreneurs. I sent emails to bloggers, former lawyers, and total strangers asking for advice. I hunted on LinkedIn and Facebook for other people in my network who could help. In the end, I sent very few resumes and spent almost no time answering traditional job posts. My new opportunity came thanks to people in my network.

Step four: take the leap.​

Leaping off the world’s highest bungee from a bridge was not scary once I realized how safe I really was. The fear was illusory. In the same way, leaving the law is not something to fear. It’s an opportunity to seize. Leaving the law gave me a chance to examine my life and my professional trajectory and make deliberate decisions aimed at creating a future I envision for myself. And leaving the law has given me a chance to do work that I find meaningful, challenging, and rewarding.

My transition away from the law has been exhilarating and yours can be too. Like the man who strapped me into the bungee, I can tell you that you’re safe. Millions of people have taken the leap without getting hurt. Many of those people are lawyers who have jumped to something else. And those of us on the other side are ready for you to join us.

Remember, too, that delaying any of these steps will only make it harder to leave the law behind. It will be harder for you to envision a life that is different than what your habits have created after years spent narrowing your legal specialty. It will be harder to take that pay cut as your salary continues to outpace those in other professions. And your network will increasingly be filled with other lawyers who do the same work you do.

Now is the time. Start today. With small, manageable steps, you can come to the edge, look out at the future, and take the leap.


Chris Jones is VP of Content for AppointmentCore, a scheduling automation software company in Austin, Texas.​ Before that, Chris was an associate in Cadwalader Wickersham & Taft’s White Collar Defense & Investigations Group in its Washington, D.C. office. Before working in BigLaw, Chris spent time working as a hostel receptionist in Chile, a news anchor in Iowa, and a Swedish professor at Brigham Young University. He received his law degree from Duke University and his bachelor’s degree from BYU. If you have questions for Chris, you can reach him at




I love reading the submissions I receive from Leave Law Behind readers through the confidential survey we have on the site. It is a great way for readers to send me anonymous thoughts and ideas and feedback and to flat out vent. And I find it an extremely valuable insight as to what the community is thinking – I always stop what I’m doing when a new one arrives.

One recently caught my eye. To the question “What challenges are you facing in leaving the law behind?” a reader answered that he or she is having a lot of trouble in deciding and determining exactly what career to move to once he or she leaves the law.

And I know this reader has voiced what many of us think: If I only knew what I wanted to do, if I only knew what I was good at, if I only knew what new professional area would be a good fit for me, I’d leave the law right now.

Before we do anything, we lawyers want it all figured out.

That sounds great, doesn’t it?

But that’s not how it works.

And that’s due in part to a prevalent issue we have in starting to leave the law: We struggle with the disconnect between how we lawyers think (risk averse, fear of the unknown, stuck in our ways, prioritizing security) … and how leaving the law can actually turn out to be (full of unknowns, full of risk, and full of creativity and exploration and adventure).

So … it would seem that our status quo mindset and the inherent chaotic nature of a life change are complete opposites and don’t seem to fit at all.

So how do we make these fit so we can make a needed change? Here are three helpful ways of thinking that can reconcile these seemingly incongruent factors so we can better prepare to leave the law:

1. Realize we are going to keep our day job. We worry a lot about money and how we will support ourselves once we leave the law. But what we need to realize is that leaving the law is a second job we take on. We’re not quitting our day job just yet.

This viewpoint enables us to not have to stress out about how we’re going to pay our bills. No matter how much we may not like it, we do not want to quit a stressful, unhappy job as an attorney just to be put into a stressful, anxiety filled spot worrying how to pay our bills.

And while taking on a “second job” of leaving the law can at first be overwhelming, with patience, diligence, and motivation, we find the free time and energy to do it.


2. Realize we are about to enter the unknown and that we will be just fine. Leaving the law is unique and new for each person. It is full of surprises, new people to meet, new skills to optimize, new opportunities, new failures, and new tests.

This is very scary.

And also very exciting.

We mainly perceive the unknown as scary because we’re just not comfortable with it yet. As a wise sage one said, Today is the Tomorrow we feared Yesterday. And guess what? Today turned out just fine.

The unknown will come soon enough, and we will see that we can handle it very well.


3. Realize that there is a structure to leave the law. While whatever will happen to us and whatever opportunities will be created by us is unknown at this point in time, the steps we will take to leave the law are not. They have been done before.

First, let’s focus on our relationship with money and plan and forecast our finances responsibly.

Then let’s really explore our identify as a lawyer and what might be keeping us tied down to remaining as an attorney in our mind and soul.

Then we will explore our skills and strengths (Unique Genius) to inform what jobs and roles we should research, assess and pursue in alignment with what we’re good at.

Fourth, will then work on mitigating the nagging fears associated with leaving the law.

And finally, we will then plan next steps for matching jobs and roles to our Unique Genius traits, and networking and “getting out there” to find a new role in our life.

Gain focus, momentum, courage. Opportunities will arise. The unknown will soon become the familiar. Rinse and repeat.


It’s funny, but once we realize that there is no way to have it all figured out … we then are closer to having it all figured out.


Here’s how going to the dentist and jumping to hit a store sign can inspire us to leave the law

February 25, 2015

I got inspired going to the dentist. One of my best friends is a top dentist in Marin County, right north of San Francisco. We grew up together, and once or twice a year, myself and two other buddies drive up, have our teeth cleaned, head over to the gym for a workout and then [...]

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How to get that (non-legal) hiring manager to take us seriously

February 15, 2015

One major theme in the feedback from the last post on Leave Law Behind is a sense of loss and confusion of how to even get started in leaving the law. This is mainly because some  of us have already tried to leave law. And it didn’t go well.   Some real life hurdles we face when [...]

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What we fear is actually what we need

January 30, 2015

I spoke with some of the winners of last week’s post contest – they carved out time in their schedule to leave the law, sent me a picture of it on their calendar and we spent 30 minutes on the phone discussing whatever was top of mind for them. It was great. Some were long [...]

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3 ways to finally take action and leave the law

January 19, 2015

What’s keeping us from leaving the law? I know, I know … we have a lot to do. We’re not sure where to start. We don’t want to tell anyone we’re unhappy. We don’t know of any jobs that pay as much as we make now. We don’t know who outside of the law would hire us. We have no time. It’s [...]

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The most important new year’s resolution you can make right now

December 29, 2014

It’s the end of December, and many of us are making new year’s resolutions for 2015. Carrying through with these resolutions, however, can be difficult. This happens because they can be too demanding, unrealistic or vague. By the end of January, our discipline often wanes. And if we specifically aspire to leave law behind in 2015, [...]

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The 5 main reasons why lawyers leave the law to join a startup

December 22, 2014

Quitting your job as a lawyer is hard. No one should ever tell you otherwise. As an associate at a law firm, you have a  stable career and an almost bullet proof trajectory to making six figures each year. Despite the freak-outs you may have about whether or not this is what you want to [...]

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You can begin to leave the law right now by closing your eyes

December 14, 2014

For something to happen, for us to be able to accomplish something, there are a lot of initial things we can do. Set goals. Define requirements. Issue spot. Rally up resources. Identify who else can help. Sketch out a budget. Lay out a timeline. These are all tangible manifestations many of us feel comfortable with. [...]

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She recruits lawyers who want a change in their life. Here are 5 things she has to say.

November 27, 2014

When Casey asked me to write a guest post, I thought it might be good to critically think about what is driving you to explore leaving the law. Before declaring to the world that you’re ready to leave law, it’s worth confirming whether you’re actually ready or if you’re just expressing frustration with your current [...]

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