by | May 13, 2021 | Jenny Milchman, The Writer's Life | 8 comments

Wouldn’t it be great if it were that easy? If when we came to the tough twists and major decision points in our lives, there was only one way to go, and it was always “right”?

Recently I reached a fork in the road related to my career as an author, but you don’t have to be a writer, or even a reader, to yearn for a roadmap through life’s turns. And if we admit that such a map can’t exist—every possible direction spawns a Choose-Your-Own-Adventure set of additional ones—then at least it’d be nice to have a method for how to settle on which way to go, as opposed to spinning in endless circles of indecision.

That’s what I’d like to give you here, in part by sharing my own recent crossroads, and in part by drawing on wisdom from people who have either made a huge choice or who help others do so.

My crossroad appeared while I was writing my newest novel. At a certain point, deep into a male character’s point-of-view, with a plot point looming, it occurred to me that this book was something of a departure from my previous five novels.

My new one delves into socio-cultural issues, like female empowerment, and pit bulls. (Yes, pit bulls are a socio-cultural issue. I’ll get into that in another post). For now, just know that my books haven’t gone to such places before. Also, this time I have an antagonist more evil, and at the same time more pitiable, than any I’ve ever created.

Once the book was done, author friends read it and all said the same thing: This is a step-up book.

Although I have five novels that have commanded some attention—a couple of awards, coverage in the New York Times and on the cover of Mystery Scene and The Big Thrill; blurbs from the likes of Rogue Gayle Lynds, Jodi Picoult, and others—I realized that this book is different, and so am I.

I’d arrived at a crossroads.

There are many crossroads to which people come; career is only one. Someone close to me is deciding whether or not a baby should be part of her life plan. A dear friend has realized that delving into past childhood turmoil might make for positive changes in her intimate relationships, and even her relationship with herself. But there are pros and cons to going back in time. It can be scary as well as liberating to open up, seek out therapy and other means of self-exploration.

How should these two women decide what to do?

Some experts say that we already know what the right answer is when we have a big decision to make—we just don’t always know that we know it. One good way to find out is this exercise.

Get a shoebox and a piece of paper and a pen. Pretend that you’re writing yes or no, go for it or put on the brakes, do or don’t, or any one word or phrase from a pairing that encapsulates your dilemma.

But here’s the key—don’t really write anything down. Just put pen to paper, or scribble some gibberish.

Then crumple up the paper and place it in the box. Put the lid on, then take it off. Remove the piece of paper. Begin to uncrumple it and in the moment before you do, take very careful note of how you feel and what your mental image is right now.

Whatever you pretended to write—if you were really about to see it on this piece of paper—how would you feel? Exhilarated? Disappointed? Hopeful? Relieved? Something else?

THAT’S the word to write on your now wrinkled scrap of paper. It tells you the answer you already knew.

My two words were leave and stay. I didn’t write them down for real, but when I unballed my paper, the scribble on it resembled an s. And in that flicker of a moment before I reminded myself that nothing real was written down, my whole body just went leaden. I felt so bummed out. And I knew what that meant: I did not want to be told—even by an exercise entirely of my own making—to stay.

But what if you truly don’t know and need some concrete guidance in coming to a place of clarity?

Ann Davidman is a therapist who helps people decide between becoming parents and remaining child-free. This article in Vox is chock full of some of the best how-to-decide games I’ve ever seen—and they are really are like games: fun, illuminating, soul-searching ways to dig into the meat and muscle of who you really are. Her strategies apply more broadly than to the baby choice—they can be adapted to many momentous decisions.  

And then there is this technique, which I wouldn’t necessarily recommend since it involves, um, life and death. Like Davidman’s method, this one can be also be adapted though. Ali Francis took a vacation just as her fledgling company was starting to succeed. Burnt out, stressed, tired, overworked—things most of us can relate to—she went where her soul would be soothed.

Something happened there, which I wouldn’t dream of spoiling, because it is flipping freaky…you have to read to believe. It caused Ali to reassess everything, and ultimately to make a decision a lot of people toy with, but never quite enact.

How can we adapt Ali’s situation without the, um, venom? Try asking yourself, if you had a brush with death right this very day, what would you regret not having done? Then follow that rabbit hole down to all sorts of other questions, like, is this something you could do? Should do? What would it take? And how will you feel if you never do?

Life is full of decisions, small and large. Rarely do we remain in stasis. Some say that the key to happiness is to be forever striving. And even if you take a more Zen approach to living in the moment, in the here and now, you still need to make choices about how such a philosophy can integrate with what you do in the day-to-day.

When I finished my new novel, the reactions I was getting pointed me in a very clear direction. John D. Rockefeller said, Don’t be afraid to give up the good to go for the great. It was time for me to admit that I wanted something different, even if that required sacrificing the security of what I had.

I came to a crossroads and I didn’t turn, I leapt. What will you do when you come to yours?

Don’t Miss a Thing!



  1. Karna Small Bodman

    What an interesting and thought-provoking piece here, Jenny. When it comes to making decisions, I often hark back to excellent advice I received from my father who said, among other things, “Treat your family and friends as if you might die tomorrow; treat your finances as if you will live forever.” I got his point. Thanks for encouraging me to think back on times I’ve had to make decisions and the wise mentors who helped along the way.

    • Jenny Milchman

      I love Karna’s father’s words, and the quotes from Gayle and Carla.

      Lisa, I am SO with you there. Those rewrites where you really feel it, ah, yes, this is right, are spun gold for an author.

      JT, that heaviness-in-the-gut aspect was key for me.

  2. Lisa Black

    This is SO true! Making career decisions is always 100% nerve-wracking. And with something as amorphous as a novel, it’s especially hard. This is why I loathe rewriting, because I honestly can’t tell if I’m making something better or worse.
    I’ve heard versions of the ‘scraps of paper in a shoebox’ technique and believe it–you have to find the choice that makes you feel good. Trust yourself to know which that is.

  3. Gayle Lynds

    Wow, Jenny, so true, and such good advice. There’s an old saying I love that goes something like this … If you reach for the stars, it’s easier to climb. Thanks for such a great blog!

  4. JT Ellison

    I really like this advice – and it is always so hard to make creative career decisions – but you have to trust your gut. When you feel heaviness when presented with a decision, that is a VERY good indicator a new path is necessary. Thanks for the cool links, too!

  5. Carla Neggers

    Great, thoughtful blog, and I appreciate the comments, too. I’ve come to many crossroads in my creative life, As Julia Cameron once put it, leap and the net will appear. Good luck to you, Jenny! ,

  6. Chris Goff

    This is a variation on a technique I saw my husband use when deciding what job offer to accept years ago. He had just retired from 40 years with CDOT and was choosing which consulting firm to go with. A boss he admired told him to reach out, shake his hand and tell him who he worked for. It came from the heart and he’s celebrating 20 years with the firm.

  7. Chris Goff

    Great blog post!