Attorney to author really isn’t too much of a stretch. Many people have done it, and a few have even been successful in the transition (John Grisham and Kristin Hannah of course come to mind as the gold standard). But even so, as I prepared to leave my (relatively short) career as an attorney, I knew I would get a lot of questions: “Why? Are you sure? Have you always known you wanted to leave the law? Do you regret going to law school?” The answers to those questions weren’t all black and white. Indeed, they were in that troublesome little grey area that seems to rear its ugly head when we’re faced with big decisions, providing just enough discomfort to allow doubt to creep in.
Nowhere was that doubt more present than when I was preparing to leave. In my mind, the big questions I needed to have answers for were, “Why are you leaving? Why not stay while you write your book? Can’t you do both?” I thought I would get these questions from every partner at my firm, every boomer, every older family member. I agonized over my answers, gaslit myself plenty on why I couldn’t “do both” (i.e., big law and my book), and almost backed out plenty of times. I bent my friends’ and families’ ears (probably until the point of breaking—many apologies) on this point and would hear their counter-arguments, agree with them in the moment, and then anxious thoughts would creep in and I would be right back to the question, “Well, should I just stay and do both? I mean, I’ve done it so far?”
And I had. That was the sticking point for me. I had done the wake up at 4am, work on my book, go to work, work a full day, come home, log back on, and answer emails through the evening while trying to write. I had done the weekends where I didn’t close my laptop so I could progress a chapter that had been barely moving due to a client’s recent crisis. I had “done both” while in law school, while studying for the Bar, while doing my clerkship, while doing big law, and while planning my wedding. If I had been doing it, and not dropping the ball in any of those areas, why leave?
Now, there’s probably a whole blog’s worth of content why I chose to write a book, why it was meaningful for me and impactful and why I knew I wanted to share my stories. That was never the question. I was solid in my answer. But the question of whether to stay or go was different. It was, at times, all consuming. Even as I write that, it sounds silly. People take leaps of faith all the time. People come and go from jobs, move to different careers, make calculated (and often not-calculated), decisions to change paths. Why did this feel so monumental? Why did this feel like the hardest decision of my life?
Well, I think it comes down to what you are trained to believe from a young age. You are trained to do well in high school so that you can get into a good college. You get into a good college so that you can work hard and go to a good grad school if you choose. You go to a good grad school (for me, law school), take the hard courses, make it onto the Law Review, become a teacher’s assistant, and study for the Bar so that you can hopefully get the clerkship or the best job after. You do well in the clerkship so that you can hopefully secure the big law job. And once you secure it, you’ve theoretically made it. How scary is it to then say, after 2.5 years, I’m leaving? To be honest, very. I thought I would receive the, “You’re crazy. You’re too young. You’re throwing away your career and you’ve barely started. The chance of making it is so slim, why risk it?” I truly agonized over my decision.
So, why leave? I chose to leave big law to pursue this dream because I knew that if I didn’t, I would look back and wonder, “What if?” What if I had devoted the time to see where this could go? What if I had bet on myself. What if this is the biggest opportunity of my life that I would be too scared to take. And you know what? The moment I (finally) decided that that answer was enough, I knew that it didn’t really matter what anyone else had to say about it. I was confident, I was decided.
I wrote out every question I would potentially get, role-played answering those questions with my husband (in case I haven’t said it enough, thank goodness for that man’s patience), and I prepared to put in my notice. And then came probably the biggest shock of this whole process. I wasn’t asked those questions by every person I told. I wasn’t asked by the majority of the people I told. I was asked by one person—one person, of the probably hundreds of people I have now told, “Why leave? Why can’t you do both. What if this is a mistake?” Every single other person surprised me in the best of ways. Instead of every question I had anticipated, I got these instead: “Woah, that’s so cool! Oh, wow, that’s my dream! That’s amazing you’re betting on yourself at such a young age. Good for you. You can always come back if you choose, but good on you for giving this a try.” And then the one that still just about brings tears to my eyes: “I can’t wait to read it when it is published.” To this day, giving notice at my law firm was one of the best days of my life. Not because I was leaving the long hours or because I was leaving the stress (both very exciting things, by the way). But instead, because the decision that had stressed me out more than anything was met with excitement, encouragement, and belief in me and my ability. It enforced that I had made the right decision— the hard decision.
So maybe the moral is this: Do the hard thing; do the uncomfortable thing; bet on yourself. Identify your dream, put yourself in a position where you can chase it (more on that later), and then take the leap. Have the confidence to try and don’t let the fear of failure— or the fear of others’ doubts—sway you. Who knows, it might just be the best decision you’ve ever made.