Turning Points: Guest Post by Leah Cypess (+Giveaway)

This guest post is part of the Turning Points blog series here on distraction no. 99—in which I asked authors the question: What was your turning point as a writer? Here is author Leah Cypess revealing hers…

Guest post by Leah Cypess

You know how they say, “Don’t quit your day job”? Well, that was my turning point. Quitting my day job.

For most of my life, writing was something I fit in between the “real” things I was doing. It was also something I never told anyone about. Writing always seemed like a secret part of me, an impractical daydream—not something to be ashamed of, exactly, but something that would lead to people asking me questions that I didn’t know how to answer. My family and friends knew, but many of them didn’t really know how important it was to me. Even after I sold a few short stories, I let everyone think that writing was a minor hobby.

For most of my life, this worked out. I’m not someone who can sit down and pound out words for eight hours a day, so writing on my commute or between classes (or, um, during classes) worked well for me. There were times when it was frustrating not to have as much writing time as I wanted, but the truth was that when inspiration called, I dropped everything else and made the time. My first published story was written during a class in high school—the teacher probably thought I was assiduously taking notes. The first manuscript I submitted for publication was finished at two a.m. on the night before a chemistry final in college. (I didn’t do very well in that class.)

Also, I knew enough about writing to know that it wasn’t the kind of career that typically provides a regular, steady income. My parents, who both grew up poor, were very firm on the importance of a regular, steady income. So in college, I majored in biology and minored in journalism, and then—when I realized that I couldn’t do lab work and didn’t want to be a journalist—I went to law school.

Law school was somewhat more intense than college, but I still found time for writing. My first story to place in the Writers of the Future Contest was written during a class called “Foundation of the Regulatory State.” And the first few chapters of Mistwood were written on the subway.

Then I went to work at a large law firm… and it stopped working out. When you become an associate at a large NYC firm, your time is pretty much theirs. The only time I had to write was on my morning commute to work; pretty much every minute from the time that I got to the office until I went to bed at night was taken up by work or necessary life things. I had a box next to computer filled with random scenes of Mistwood I had written on the train, waiting to be typed into the computer and formed into a comprehensible manuscript. That box sat there, getting fuller and fuller, for two years.

I decided quickly that once I had built up enough savings, I was going to quit. But as I continued working, that goal began to seem more and more distant. I was spending almost every waking hour concentrating on my legal career and surrounded by people who were doing the same. Quitting law entirely started to look to me the way it would look to most of the people I knew: like a flakey and weird move. Like I had failed.

I started to look for more reasonable reasons to quit. I took the GREs and applied to graduate programs in history. I looked for ways to do legal work on a freelance basis. I started seriously dating a guy who lived in Boston (okay, that wasn’t entirely just to find an excuse). But what finally gave me the impetus was the growing realization that I was going to marry this guy who lived in Boston, and that pretty soon afterward we would probably have kids. I wanted to have kids, but I also knew that once I did, it would be approximately 18 years before I could do anything full-time again. This was my window of opportunity, and it was closing.

So I did it. I quit.

Surprisingly (or maybe not), the reactions of my fellow lawyers were more positive than I had anticipated. One or two clearly thought I had actually been secretly fired, but most of them seemed to sincerely admire me for following my dream. I had saved assiduously while I was working, so I had enough savings to keep me going for a little while.

In terms of my writing, this turning point did not create any dramatic results. About four months after I quit, I sold a short story to Strange Horizons. And then… nothing. For years. Well, not nothing—I got revision requests, I got invitations to submit more work, I even got to meet with an editor who was interested in one of my manuscripts—but no book deal, no award-winning story, nothing that I could point to and say, “Look what I’ve accomplished! I am not a failed lawyer, I am a published author!”

I gave birth to my daughter about a year and a half after getting married, so my period of full-time writing passed without any milestone that could make me say it was worth it.

But during that time I joined a critique group; polished a manuscript; made connections with editors who liked that manuscript; finished and polished a different, adult manuscript; submitted Manuscript #2 to agents; and got summarily rejected by all the agents. So when I went back to being a part-time writer, I was in a good position for the next steps: figuring out that Manuscript #2 was actually a young adult manuscript and sending it to all those editors who had really liked Manuscript #1.

And so at last, more than four years after my “turning point,” I got an offer for a novel and could call myself “published.”

That might seem like the moment when my decision to quit proved worth it. And it’s true that my dream—the gold at the end of the rainbow—was always to publish a real book, and I hope I never stop being happy that I achieved it. But the truth is that even if I still wasn’t published, quitting would have been worth it. When my first book was published, I became an author. Four years before that, however, I decided to publicly declare myself a writer. In many ways, that first turning point was the more important of the two.

Leah Cypess used to be a practicing attorney in New York and is now a full-time writer in Boston. She much prefers her current situation. She is the author of Mistwood and Nightspell, young adult fantasies published by Greenwillow Books (HarperCollins), as well as of numerous short stories.

Visit her online at www.leahcypess.com.


Congratulations to the giveaway winner of a *signed and personalized* copy of Leah Cypess’s novel Nightspell! The winner is…


Congrats, Vivien! Thank you to everyone who entered—and to the author for the prize.

There’s more in the Turning Points series. Catch up with any posts you may have missed here.

30 responses to “Turning Points: Guest Post by Leah Cypess (+Giveaway)”

  1. Holy cow, quitting your day job? That had to take a LOT of courage, but I’ve very glad you did since the results are two wonderful books and the promise of more.


    • Thank you, Dot! That means a lot. It did take more courage than you’d have thought, considering I never wanted to be a lawyer as much as I wanted to be a writer.


  2. Yay! I’ve just quit my day job to focus on writing. Thank goodness someone else has done this and it has paid off! Finger’s crossed 🙂 Here’s to following the dream!


    • Thanks, Christina! I think when you do love something, it’s a bit hard to let people know about it and open yourself to criticism. (Though of course the goal is to get published, and once you do that’s exactly what happens,in spades. It’s a wonder any writers stay sane.)


    • Thanks, Michelle! To be fair, it took me 2 years, mostly because I wanted to pay back my loans and save up money. So as gutsy moves go, it was a pretty cautious one. 😉


  3. “But the truth is that even if I still wasn’t published, quitting would have been worth it. When my first book was published, I became an author. Four years before that, however, I decided to publicly declare myself a writer.”

    I love this story so much. So inspiring. I commend Leah for being brave enough to do what most of us only dream of..


    • Thank you, Laura! I would add that I could have declared myself a writer without quitting my job… they came in the same package for me, but they don’t have to.


  4. That sure takes some courage!! I don’t know if I could do it. I need to have something I can rely on. It would be utterly terrifying. Best of luck to you!! But you seem to be doing great 🙂 Great inspiration!!


    • Thank you! I think it’s smart to want something to rely on — like I said, I didn’t do it until I had a significant amount saved up.


  5. Thanks for this–it’s been hard to own my decision to leave my job and not seek another when my husband and I moved for his career. Dedicating my time to writing instead of a career that wasn’t making me happy anyway is a hard decision to justify to my overly-practical mind, but you’re right–there’s no measure of outward success that makes it the right decision.


    • Thank you, Rowena. I’ve also had “be practical” drummed into me, and while it’s good advice when it comes to financial stability, I also think you have to be practical about what will make you happy vs. what you’re doing so other people will think you’re successful. Moving is definitely a great time to make that leap. Congratulations on your decision, and good luck!


  6. I have always been a fun of The Thief series which is how I heard about Mistwood and Nightspell. Love them both!


  7. Leah, I loved your story – and could relate, having had a similar turning point, except that, for me, it was in deciding not to send off the law school applications I had ready to go out. I’d read in a school pamphlet that I should expect to graduate 125k in debt… I had just drafted my first novel and remember the moment of asking, would I go that far in debt for my writing? Your turning point was very poignant — and also has me intrigued to read your work. Thanks for sharing.


    • Thank you, Elissa! I do remember thinking hard about whether to send out my law school applications. In the end I don’t regret sending them, but that’s easy to say now… those two years working at a firm were very difficult. (And back then, at least, most graduates were guaranteed work. Not the case anymore.) Good luck with your writing!


  8. Loved, loved, LOVED Mistwood. And your story of how you got to where you are is so inspiring. It gives me a lot of hope for my own writing. Thank you.


  9. So excited to read Nightspell! It is inspiring to read about how you achieved your dreams. It gives the rest of us hope!


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