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7 Things I Learned from Writing a Book

Updated: Oct 15, 2020

As many of you know by now, I am eagerly anticipating the upcoming publish date of my own book 10,000 Nos: How to Overcome Rejection on the Way to Your Yes this October (October 27, 2020, to be exact). So, as a service to the public (ahem), I'm gonna give you the good, the bad, and the ugly of writing a book.

Soooo many people tell me they want to write a book, or they have an idea for a book, but they don't know where to start or can't get a publisher or they're not up to the task of figuring out self-publishing. Here's the thing: I've had all of those very same internal struggles and yet, somehow, by the grace of God, I have an actual, real-life, I-can-hold-in-my-hands book.  And it's actually published by one of the big, well-respected publishing companies, Wiley & Sons. This is something I sometimes dreamed of, but didn't really think was possible unless I won an Emmy or an Academy Award.

I learned a lot through this process, and here are my top 7 tips that I want to share with you:

1. The seeds that you planted years ago may not break through the ground or start growing for a lot longer than you anticipated when you planted them.

I have recently come upon files in my computer that were created as far back as 2013 (it's now 2020) that are basically failed attempts of this exact book. By that point, I had been kicked around as an actor for 18 years. I moved into Manhattan on January 1st, 1995 to pursue acting, after having done my first play at Boston College in my junior year, taking acting classes at BC, getting a film studies minor to accompany my English major at BC, doing a musical near my hometown after graduation and trekking into the city two nights a week the entire fall of 1994 for acting classes, while also doing some terrible local projects for things like cable-access TV, if you remember that. But by 2013, I felt like I had something to offer: I'd been a significant part of groundbreaking shows like The Sopranos and The West Wing.  I'd done a season on a Showtime show called The United States of Tara, created by Academy Award Winner Diablo Cody, and starring Academy Award Winner Toni Collette. I'd worked with legendary directors like Guy Ritchie and Ivan Reitman. I'd been supporting my family for a bit with my acting (barely) and I was occasionally recognized by strangers for my work, but largely, I felt like I was barely treading water. So it was two-fold: the book was kind of to help others going down a similar path, but also to save me. Though I faced one major block...I thought (probably correctly at the time) that no one was going to care what I had to say if I hadn't won an Oscar or an Emmy.  I still haven't won one of those.  But I do finally feel like my story is worthy of a book and I do believe and it's going to help some folks.

But it was only made possible because I planted those seeds way back seven years ago.  Shockingly, in one of those documents, I even wrote a list of potential titles and one of them was 10,000 NOs!  That pre-dates the podcast, which I started in 2017, by 3 or 4 years!  That's unbelievable to me.  So don't just dream.  Write down your dreams! They may be more attainable, and not as far off, as you think they are at this moment.

2. Even if no one but you ever reads it, writing down your story is a VERY POWERFUL exercise that will absolutely reward you in one way or another.

At some point, around 2017, just before I launched the podcast, a friend of mine (and now a past guest) who is a New York Times best-selling author and a world-renowned public speaker, told me she thought I could speak publicly, given my theater training, career story and ability to articulate lessons from it. So she mentored me and we set about creating my narrative. And I was really hot and heavy into it, working my ass off every day, with the hopes of creating an additional revenue stream to support me in the inevitable lows of an acting career. At one point, I was talking to my friend Chris Messina, a fellow thespian, and he said, "I don't know if you'll make money doing speeches, maybe yes, maybe no, but I think it's a good thing for you to be telling your story like this". He could not have been more right. What it does, is that it allows you to specifically and consciously present the narrative of you to the world.  

Without realizing it, we go through life like a pinball: our parents tell us who we are, our siblings, our teachers and coaches - everyone besides us. And what we end up taking on as "our story" of who we are is really just a cobbled-together version of who everyone else said we were. When you write a story, the one that only you can write because only you have lived your life, with you as the protagonist, you start to see yourself as the hero of the story. Now, I'm not saying you make that hero a cardboard hero that only has strength and smarts and know-how. I'm saying a real-life, flesh and blood, human being who - while they fail, and fail often - heroically presses on. When you do that, even if no one else reads it, you empower yourself.  

You'll find yourself shrinking less. You'll find yourself taking up your space, owning your power, and graciously thanking people when they tell you your story helped them in some way rather than deflecting it the way I used to do, and still do from time to time. Craft your narrative!

3. Don't hide behind other people's "better" stories.

This is intrinsically linked to the previous lesson, but it's worth mentioning. After I secured my publishing deal I told my friend Jon Gordon, that I was planning to make 10,000 NOs like Tim Ferriss' Tribe of Mentors (which is a collection of stories and lessons from Tim's multitude of heavy-hitting guests he's interviewed). Jon stopped me in my tracks and said, "Tribe of Mentors is Tim's third or fourth book. His first book was Four Hour Work Week.  That's what put him on the map.  It was the story only he could tell. 10,000 NOs needs to be the story that only Matt Del Negro can tell. I'm reading that book because I want to go behind the curtain of Hollywood and the entertainment industry, with a real-life working actor, and I want to hear what it's really like - not the version on Entourage. If you write that book, you're gonna have a best-seller on your hands.  That's your book.  Don't hide behind other people's stories. There's plenty of time to highlight them later.  But your story is worthy of being told.  Your life, as it is, if told honestly and openly, can actually help people.  That's what you need to write".

Thank God I spoke to him - because I was set on hiding behind my guests big time. Instead, once I put fingers to the keyboard, I just let it flow out of me. And what came out was not just about acting. It was about life - my life, specifically. Lessons I've learned on sets, sure, but also on sports fields and in classrooms and in situations far beyond my career. And it still includes tidbits and quotes from big-wigs like Henry Winkler, Richard Schiff, Suzy Batiz, and Mark Duplass as well as unknown folks like Mike Boyle, Rob Grupe, and the late Rob Whitaker. But I didn't use their big stories as a barricade behind which I could hide. I used their stories to amplify the lessons I'd learned myself and to show readers that, no matter what field they came from, what level of "success" they deemed themselves to have achieved, no matter how young or old they were, these lessons apply to all of them! These lessons apply to you. So don't hide behind other people. Write your story so we can learn from you, specifically. And even if you never share it with anyone, YOU will learn from you. I promise.

4. Writing a book is like the old proverb about eating an elephant one bite at a time: you can only write a book one chapter at a time.

Full disclosure: As an English major, a prolific texter (my texts have been described as Dickensian in length), and a closet screenwriter, writing is a skill that I've spent a lot of time on, whether I was aware of it or not. I even joke that the only reason I was able to woo my wife is that our courtship began largely over email where I was able to turn some clever and witty phrases and make her laugh with my writing skills as we began to date. We had chemistry but I felt like the written word was my sword, as I had to distinguish myself from all of her other suitors, especially because her first impression of me was that I was a skin-deep, bartending, wannabe actor. I had a lot to overcome on the path to her heart!

In order to get the publishing deal, even after Jon Gordon had graciously shared a small writing sample of mine with Wiley, I had to write a book proposal, to get the official nod.  There was one problem:  I had no idea what a book proposal was! So I reached out to a friend, who has a career that is a lot more accomplished than mine (including a stint in the White House) and asked if I could use a copy of a book proposal he had just written, as a template. That proved to be very helpful: I basically took what he had written (which was completely different content - a historic, political book) and transposed it into my content.  And then tweaked it and made it my own.

What that forced me to do was to take this big blob of life experiences and break it down into sections, known in a book, as chapters.  These ultimately changed a little bit, but largely that original list is the spine of the book. When Wiley told me the whole thing should be 50,000 - 60,000 words, I was scared shitless of the huge number - but ironically, in the end, I went over on words and had to pare it back. But rather than be daunted, I took that total number of words, divided it by the number of chapters, and realized, each chapter would be about 3,000 words. So I went to the first chapter, aptly titled, "Getting Started", and wrote. I just let it flow out of me.  After a while, I paused and checked the word count. I then began to angle toward ending that chapter around 3,000 words.  If I went significantly over or under, I figured I would deal with that later.  For now, I just needed to do this with every chapter.  And that's what I did.  

5. Don't Be John Wayne and go it alone... get help!

It wasn't until a lot later in the book writing process that I was given an editor, the incredible Julie Kerr. By this time, I'd been writing alone for so long I was kind of worried she'd hate it. But she didn't. And while the book is shockingly similar and unchanged to the original manuscript I puked out, her help was immense.  

The analogy I give you is this: if you've ever had work done on your house, they come in, bust the place up, and do all the remodeling.  Then, when they've pretty much made the place look amazing and totally new, but they're not quite done, they move on to their next gig.  And you've already paid them the bulk of their fee so now it's a pain in the ass to get them to come back and do the final touches. But those final touches are really important. And on a book, even more so. The way Julie, with her expert eyes, could help me snip and rearrange sentences or sections, or rename subtitles, made everything flow. Where to place the guest quotes, where to break up a section or thought... all of these are key decisions. So if you want to write your own book but are too scared, I'm saying to you, "Who cares? Write the book!" If you do it well, you get help and that help makes it so much better than you could have done on your own. But you won't get help if you don't write the book because no one in their right mind, with the tools to help you, is going to help someone who just says "I want to write a book someday."  Take a number!

And the help I found wasn't just in the form of my editor.  It was the whole thing: format, font, jacket cover, endorsements, photo for the cover, and the inside jacket - all of it! Just like as an actor, my work is only as good as my collaborators: if you give a great performance but you have a terrible director and editor, that performance likely ends up on the cutting room floor. You are only as good as the team you surround yourself with. But you've got to be the leader who galvanizes that team with your passion for what you're writing.

6. Do it for the Love of the Game

When I met Jon Gordon, he was just another guest. But we hit it off and stayed in touch. Later, when his daughter was considering a career as an actor, he asked if I'd have coffee with her to give her the scoop. I did. A week or two later, I was working on a small writing sample that, at the time, was just going to be a short, free e-book for my website to entice people to sign up for my then-non-existent newsletter. I wasn't even going to do much with the writing.  But when I finished, the app I was using (Scrivener) made it look so cool and professional and I thought, "Huh. This looks like a real book."  Almost as an afterthought, I emailed a copy of it to Jon with a note that said, "Your daughter might find this helpful.  It's basically all the same stuff I told her over coffee."  And that was it.


The very next day I got a text from Jon saying, "move this, change this and send it to my publisher" and he gave me their email.  That's how the book deal came about.  But it wasn't even that I "did the work" of writing that e-book. It was the work from 2013 when I created that first file. It was the work from 2017 onward when every single week I'd write up an Intro and an Outro for my guests on the podcast. It was the work of creating that narrative of a 45-minute speech with my mentor who told me I could do it for money, even though I hadn't made a dime speaking at the time. 

All of that stuff, I did for the love of the game. And it just so happened that people were watching.  And liked what they saw. So they decided to help me.  That's what I suggest: do it for the love of the game.

7. Don't Let the Critics, Including the One in Your Head, Stop You From Writing Your Book

When I say "book" I mean it proverbially.  It can be anything that's daunting that you want to do.  Sure, it's a lot of work. Sure, you're not a pro. Who cares? You're gonna die someday. Just start. Don't overthink it. You don't have to let it upend your life, just take a baby-step toward it. The rest will work itself out.

Don't do it to sell books. Don't do it so you can tell people you wrote a book.  Just do it for you. Do it because telling your story, whatever it is, is a worthy pursuit. It will help you regardless of who you are or what your goals are. And that's not BS, I mean it: it's like a vision board for you.  Tell the story that empowers you.  Choose to see your life in a way that makes some kind of sense, that contributes to the higher good, that leaves the world a little better than you found it. The voice in our head is often the harshest critic, we can't live our life by their rules or we'd just be...sad.

At the end of the day, the most important lesson I learned was...

Just go write it. 

That is all.

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