This is the 1st of your 3 free articles

Become a member for unlimited website access and more.

FREE TRIAL Available!

Learn More

Already a member? Sign in to continue reading

Freelance Success: Writing a book while maintaining a freelance career

It's all about learning from your mistakes – repeatedly.

Add to Favorites

For the past 16 months, I have been writing a book while trying to maintain a passable version of a freelance career.

How is it going?

“Why am I writing this book?” I moaned to my wife precisely 14 hours ago. 

I’m approaching 88,000 words. The manuscript maxes out at 100,000 words and is due exactly two weeks from when I’m writing this. I’m going to stagger across the finish line past the paramedics’ waiting arms and face plant into the closest shrub.

I wish I could present an unbeatable plan for how I pulled everything off, tied the book in a neat bow, and lived to write another cliché. The truth is, I’m not sure I did. While my draft lays dormant – waiting to pounce when the sun rises – I’m writing this piece. It’s 11:25 p.m. on Saturday. Wait, the kid had a meltdown preceded by three separate trips to check on her. It’s now 12:50 a.m. My eyes feel like the inside of a hot sauce bottle. This column, theoretically, was due yesterday. The family checkbook is in constant peril, but I don’t have the attention span to resuscitate it. Not that my efforts would do much good, hence the exchange with my endlessly patient wife.

Check the archives, but I doubt “Freelance Success” has portrayed such a pathetic oxymoron. But learning to succeed – as many gift shop coffee mugs have taught me – means learning to fail. The book will get finished, but it wasn’t done in a way that was beneficial for my mental health.

A very naïve part of me thought that because I was writing a book, life would grow more amenable. I was living my dream. The gears of life crush you no matter who you are. Casey struck out. Buddy Holly’s plane never landed in Fargo.


On that cheery note, it’s time for some less morbid insights. 


Few people care that you’re writing a book.

Some people do. Your parents are probably happy for you. Ditto your spouse and the few friends you don’t annoy on Facebook. You’re still a writer. Nothing has changed save for the scope of the project. Maintaining that perspective will help when life gets in the way. My inconsolable child might be your sick dog or an ill relative or a broken water heater.

Producing work under duress – and knowing when to rest – is an enduring feature of the gig. A couple of weeks ago, I was battling a cold that refused to succumb to my usual OTC roulette. I visited my doctor, who prescribed two antibiotics and rest.

“Ah, man, I’m writing a book,” I said.


“Well,” she said. “You can write it in your head.”


Keep up your routine…

I stunk at this. I waved goodbye to so many things: regular hours, therapy, trips to the gym, regular exposure to the sun.

The idiocy of hoarding my time emerged when our daughter spent four days in the hospital – right as my cold decided to extend its stay. It was a minor procedure – an infected lymph node remedied in 20 minutes. For a two-and-a-half-year-old, the experience was cataclysmic. Three nights in a weird place as a rotation of strangers poked and prodded her, brokering a strange and incomprehensible intimacy while Mom and Dad kept smiling. We spent days consoling a confused, scared little girl. Discharge day for all of us felt like being sprung from a cage. The kid sprinted to our front door, and we all exhaled from a forced vacation of sterile, endless hallways and powdered eggs.

I returned to writing the next day. That week was brutal. I had to finish four freelance assignments – including this column – while tending to the manuscript. As I caught up on the book, a thought pierced the fatigue. I was still on pace to meet my deadline after four enervating days in emotional limbo, followed by a hillock of make-up work. Surely, I could have devoted three hours a week to working out or finding ways to take care of myself.



…And that includes freelancing.

I wanted to talk to other writers to make sure.

Food writer Adam Erace and film critic Mike McGranaghan made book writing part of their days, fitting it around other gigs. Their upcoming works: two cookbooks and a look at the 1980s’ weirdest movies. My book is quite different. It covers the nearly decade-and-a-half emergence of the NBA as an entertainment and business empire.

But the lesson is uniform: Know your limits and nudge your boundaries.

Embarking on a 2,000-word, deeply reported story while working on the book would have driven me to despair. I did write a few 500-word to 1,000-word profiles that I completed on time and to my editors’ satisfaction. If I write another book, I’d like to do that kind of assignment a couple of times a month.


Now that I know I can do it, I will. At the very least, I can make my advance last longer and open my checkbook with a feeling that isn’t despair.


It’s a sacrifice that’s worth it.

If you’re writing 100,000 words on a topic, it better be on something you love. That has sustained me. This book has been marinating in my brain for years. I couldn’t bear anyone else writing it. Or having the fun I’ve had. That has atoned for the years of writing obituaries and town council meeting write-ups and other things that made me wonder if I was pursuing a lark disguised as a higher calling. I spent years petrified that the potential I possessed as writer would curdle into regret and resentment. Potential, after all, runs out.

Writing a book is a massive expenditure of time and energy, but nobody takes this job to achieve wealth. You do it to reach that special high: you must express something, and writing is the most satisfying way to carry it to the willing masses.

It’s now 2:40 a.m. My eyeballs are so arid, you could light a match on them. Yet I can tell you why I am writing this book.


Why do any of us write anything?

Because we have to.


Veteran freelance writer Pete Croatto (Twitter: @PeteCroatto) is working on his first book for Atria Books, an imprint of Simon & Schuster.