15: Special, Not Special: How to Work Your Way Out of a Dip

“The explorer is the person who is lost.”
—Tim Cahill

I rode the high of hitting my 50,000-words-in-a-month NaNoBlogMo goal for exactly one day last week.

For one day I was over the moon! I did it! I wrote almost every morning for one month, and came out with 50,000 words by the end of November. It was like running a mental marathon! Combined with my October practice of trying to write for 30 minutes each day, I had amassed 100,000 words of a book draft. For those who aren’t word nerds, that’s about 350 pages double-spaced. Definitely cause for celebration!

And then, as predictable as ever, the crash came. THE DIP.


The day after I triumphantly topped off my word count tally, I printed my book draft at Kinkos and proudly carried it home (in a box! Paper clip wouldn’t fit!).

I snuggled up with my rough rough rough first draft. I was prepared to dislike it, but I wasn’t prepared to hate it. As I started reading, I began crossing off entire pages. Page after page. Cheesy! I would write in the margins. Blah! Clean up! Remove!

How did things sound so much better in my head than on the page? I couldn’t help but compare my insides to other author’s outsides—the (polished, finished, edited) books I read with my coffee every morning were so sharp, interesting, engaging, and intelligent. Why was mine sounding so juvenile?

All of a sudden I was encountering an overwhelming number of articles and books and people who were saying exactly what I had worked so hard to capture in my writing. My ideas felt old, obvious, already done. I couldn’t believe it. My heart sank when I realized how unoriginal many of my concepts now felt. Even my personal story—quitting a fancy job, wiping out my savings, wondering if I should throw in the towel on NYC and my businesses and eating power bars for dinner—felt like just another entrepreneurial cliché.

I know as well as anyone the cheerleading rally cries for writers and creatives. I know the importance of getting a shitty first draft down . . . I wrote about it last month! I know it was important for me to just write in November—to build the habit, and to let myself write something “terrible” so that I could at least have the bones of a book to bounce ideas off of.

Every day I am so grateful to be writing a book that will be traditionally published that I could cry. This is the privilege of a lifetime, and every problem that comes with it is a problem I am lucky to have. 

It would be so easy for me to paint a coat of gloss on this process and pretend it’s all shiny and perfect, that I expected the dip (which I did) and tell you that I just kept plowing through with no less spring in my step. But alas, I have always promised myself and you that I would share the ups and the downs. It bugs me to read things that are too “shiny”—I can’t relate to them, especially as a card-carrying member of the 10,000 hours of neurosis club.


I am hoping that if I tell you about my inner critics they will pipe down a bit. In 8 years of blogging, I have learned that when I share the things I’m embarrassed about, it gives other people permission not to feel so crazy themselves.

I have a whole committee of inner critics, but there are two in particular that sit on my shoulder when I’m working on the book: The Innovation Police and Mr. Amazon One Star.

  • The Innovation Police are very concerned with me writing an original book, full of new and different ideas (this is important to me too, of course). They are very smart and well-read, and they know everything that is already out there. They are extremely versed in the landscape of books throughout history, and the thousands of articles published online every day. They have a roster of experts with fancy credentials that they are ready to cite instead of me. They are constantly giving me reminders like, “It’s noisy out there! Shape up! That has already been said! More! Better! Different! Think harder! In fact, maybe you should just quit and give back your book deal while you’re (not) ahead!” (Never!)

  • Mr. Amazon One Star is reading and writing with me, sentence by sentence.“That one!” He’ll say with a crazy smile. “That’s the sentence I’m going to quote when I skewer your book on Amazon!” The funny thing is, I’ve gotten one-star reviews. One of my favorites is titled, “If you’ve never thought about anything ever this book is for you,” in which the reviewer goes on to say, “This woman is crazy, like the type of person you just try to have little to nothing to do with because of her stability issues (I wouldn’t be surprised if she lies crying on the ground for hours after reading this review).” They’re quite entertaining. And you know what? They don’t kill you. I would never let the prospect of one-star reviews hold me back from putting my work out, but Mr. Amazon One Star is still a sentence sleuth while I’m working . . . just waiting for me to slip up so he can call BS.


The friends and family I have shared these concerns with this week have completely propped me back up. In fact, I might as well be sitting in one of those chairs hoisted up at a Jewish wedding, they’ve made me feel so supported and reenergized! A mental and emotional Hora dance if you will 

It really is true that sometimes people see and reflect our own unique value before we can even see it in ourselves, or when our inner light dims, which it inevitably will on any creative undertaking. As I often remind myself, if things like this were easy everyone would be doing it, and I would be bored.

I know the struggles and searching of this week are going to inspire me to write an even better book—they already have. As with my mission when writing Life After College, if this book helps just one person feel less alone or find their way forward, I will be thrilled. (And please, this post is not meant to be encouragement bait—if anything, I’d love to hear who is on your inner critic committee so we can throw them all a party!) 


I’ve written before about the paradox facing any kind of “expert” or person who earns a living on ideas (though in a way, we all do).

On the one hand, you have to have some level of ego that says, “I have something unique/important/valuable to say! People should listen to me!” On the other hand, anyone with a healthy dose of humility is quick not to take much credit; to defer to luck, timing, shared experience, mentors, community, being born into a first world family, etc.

We are all special snowflakes (yay) and yet we are also all archetypes. We are not as original as we sometimes like to think, and our personal “problems” aren’t always so personal.

We can be categorized and described based on all kinds of things: life stage, age, gender, zodiac sign, generational profiles, personality profiles, the list goes on! Gail Sheehy wrote a bestselling book called Passages on “predictable crises of adult life.” Seth Godin wrote the definitive book on the predictability of The Dip and how to know “when to quit (and when to stick).” Ben Horowitz and Clayton Christensen both wrote books on crises in business, The Hard Thing About Hard Things and The Innovator’s Dilemma. Joseph Campbell wrote the meta narrative on personal growth that trumps all in The Hero’s Journey.

The more I learn, the more I know that I don’t know. The more I read, the more patterns and repetition I see. The more I write, the more I climb up the shoulders of giants. This cycle of awareness can be paralyzing!

There’s actually a name for this—the Dunning-Kruger effect—a cognitive bias where skilled individuals rate themselves lower on aptitude scales, while people with lower skill and/or intelligence tend to rate themselves higher. Ignorance truly is bliss!

Part of my own compulsion for bullshit detection comes from the disdain I have for snake oil salesmen—people who project one image or sell a form of “expertise” that they really have no real-life basis or qualifications for. While I generally believe “a rising tide lifts all boats,” I don’t appreciate boats that are made of smoke and mirrors, and I see plenty of them online. I suppose this is another critic on my own committee—the one who is very firm about making sure that I am as qualified, honest and authentic as possible for the projects I create.


“The fishermen know that the sea is dangerous and the storm terrible, but they have never found these dangers sufficient reason for remaining ashore.”

—Vincent Van Gogh

I know I am hard on myself. But I also wouldn’t necessarily change that, I just need a little time sometimes to snap out of it. Handstands help, as does meditation, fresh air, talking to friends and family, and taking a few days off.

Our strengths can become weaknesses when taken too far, but our “weaknesses”—our flaws and neurosis—are also some of our greatest gifts, especially when it comes to connecting with others through empathy, compassion and grace.

Isn’t it funny (if not perfect) that writing a book on pivoting is requiring me to shift my strategy mid-stream, to give my framework a legitimate road-test? I will be the first to say that The Pivot Method isn’t meant to always be easy or problem-free, but rather to help us cycle through problems and “stuck” questions faster and more methodically.

My desire to create something unique and insanely helpful is what motivates me to keep going despite the dip; to dig deeper, to do better. It is what motivates me to solve the problems I also struggle with. Or at least make my own small (special) dent.


Today’s episode covers all these topics and more . . . take a listen here: