Select Love Letters To A Freelance Writer Part One

by Michael de la Guerra in January 10th, 2018

A Quick Note On Love Letters To A Freelance Writer: This is a select batch of emails I sent to a group of writers I was coaching. I intend to publish the entirety of them as a collection. There's a form you can use down below to a be notified when I do so (if you like what you've read, of course).

Introduction: Author's Note

Dear reader,

I should probably be worried about getting sued. Reading through these personal, and at times, quite melodramatic, notes shocked me. If you’re a writer of the “pull all your material from your actual life” variety as I am, you find yourself constantly toeing the line between infusing too much of yourself into the work, and not using nearly enough. The former is risky because you might alienate people you write about (along with repeating the same stories over and over), while the latter can sometimes lead to writing that lacks emotion. Add to this the steady drip of negative self-talk that all non-sociopathic writers shoot straight into their veins, which hits like a shot of heroin—but instead of a warm rush of painlessness, there’s just a voice in your mind that repeats the words, “Who do you think you are?” and, well, you’ve got my exact sentiment. 

Who exactly do I think I am? How could I just put all my bullshit out there like that? These were the questions I asked myself as I paced across my room this morning at 5 a.m. My anxiety was peaking, and I had the urge to scrap this idea. 

Fuck these “lOvE lEtTeRs,” I told myself. You’re such a faux-romantic sap.

(I know, my inner critic is very mean; we’re working on it.)

Writers go through this phase all the time. What hit me hard, though, was the level of intimacy in these words. These were some of my darkest secrets: stuff I’d rarely even tell partners. And here I was just doling them out to strangers, with the intent of sharing them with even more people. Two thoughts then came to mind:

  1. Is it more noble to try and hide these stories within my fiction writing in order to avoid the real-life repercussions?
  2. What am I really hoping to achieve here?

To the first question, my answer would be “no.” And when I gave myself a moment to think clearly about the second, I stopped pacing. Romeo, my cat, closed his eyes and went back to sleep, instead of staring at me like I was a maniac. I sat on my bed, and all the guilt, shame, anger, fear, etc was overridden by what has always been my guiding principle: if anything I write has the potential to touch someone, to move them to improve their life, or even to just help them feel less alone for a moment, then I almost have a duty to share that experience. 

I’m not sure that would hold up in a court of law. It felt right this morning, though, and still does now when I say it out loud. So, I hope you are moved by these short notes. I hope you feel closer to me, or to some parts of those stories in some way. That’s all I’ve ever really wanted: to feel close with people. Because I know what it’s like to feel alone, with scant resources to pursue your goals, sinking deeper into the sea of overwhelm, weighed down by your own ego that would rather drown than ask for help, made heavier by the idea that you’re a fraud and should just quit. I hate that feeling, and I’ll do anything I can to rescue another being from that well of despair.

- M

Love Letter To A Freelance Writer #2: My grandmother was a drug dealer

Dear reader, 

I bought my first gram of cocaine from my grandmother when I was 14. This sounds absurd when I write it down now, but yes, it’s true. Like many American millennials I fell victim to opioid addiction and—not surprisingly, given the opening sentence of this email—I ended up strung out on heroin at 19. But that wasn’t where my journey started. 

I grew up surrounded by chaos, and while I’ll save you the gory details (I have memories of DEA agents storming my house looking for “Grandma Cookie” when I was only 11), what I will say is that drug addiction, and the inter-generational trauma that usually accompanies it, has plagued my family for years. That same trauma led me down a brutal path of self-destruction, and I inevitably dropped out of college to go to rehab. And I didn’t know it at the time, but I was about to break the chains of a disease that has taken so many of my own family members. 

We’ll continue this story at a later date, but… spoiler alert: I’ve been clean and sober since 2009. And whenever things get tough, I try to take myself back to the moments right before I checked into rehab, and remind myself how much I’ve overcome. When I have to dance with fear, sadness, and loneliness… I can’t imagine it being worse than what I’ve already gone through. Now your story may not look like mine, but I do know one thing: You have pain like I do. But you’re still here, too. If things are uncomfortable, be it in your career or your personal life, take yourself back to a trying time when you felt like you couldn’t breathe; take yourself back to the hopelessness you felt, then… remember that you pushed through. When I first started out as a freelance writer, I was rejected over and over again. It was part of the journey. But it was never as scary as waking up in the shower, with a needle in my arm, and a screaming girlfriend overhead, as I thought, “Wow, you know I’d really hate for my dad to find me dead.”

To think I went from dropping out of college (something I want to share about in the next email), to being featured as a case study in the Harvard Business Review, and making more than the average writer while working only 20 hours a week, is beyond crazy. I have to pinch myself sometimes. Wherever you are now, don’t worry. Soon enough, you’ll get to where you want to go. As long as you keep writing. 

- M

Love Letter To A Freelance Writer #3: Dropping out of college

Dear reader,

When I dropped out of college at 19 to go to rehab, all I knew was I didn’t want to die. I remember sitting in a concrete courtyard, watching the older people suck cigarettes through gaps where teeth had once been, their bodies frail and tired, beaten down by years of drug addiction. They’d been in and out of rehabs and prisons their entire lives, now looking at the youngsters like me thinking to themselves, “If only I’d stopped when I was your age.”

Some of them took me under their wing and tried to protect me by warning me of what would happen if I continued down the path I was on. I was scared. I knew I didn’t want to be like them. So when I got out, I pursued life with a passion I never had before. I got a job in the music industry, and worked there until I got sick of it and ran away to a corner of the entertainment world here in LA where I was able to hide at a desk. All the while, I wrote. 

I didn’t know what I was writing, or that I even wanted to be a writer; I just typed away. (I can’t read them now; they’re too cringey for me—can you relate?) Then I realized I couldn’t hide anymore, and decided to pursue writing more seriously. I did everything I could to turn it into a career, but there was a problem… I didn’t feel like a real writer. But that’s what was happening on the surface. We all have moments where we feel like imposters. This was something else. My entire life had been one big identity crisis, and I never felt like a “real” anything. I’d always felt like I never fit in anywhere, no matter what. And I went to great lengths to cover up these feelings, including shoving needles into my arm.

I was eventually able to turn writing into a career, and I’m going to share exactly how to do the same. But if you’ve ever felt like you’re not ready, let me be brutally honest with you: it doesn’t matter.

There are people who need to hear your story, and businesses that need you to help them communicate their message. You are doing them a disservice by keeping yourself trapped in the “one day” mindset. And just like those old addicts I observed in rehab, you may look back in a few decades and say, “If only I’d started sooner.”

Because who is a REAL writer? In my opinion, it’s someone who gets up every day, does the work, and writes. 

So get busy :-)

- M

P.S. I always advise clients not to tell their whole story in one email, so… while there is a lot more to my story—because our lives are more complex than just a few highlighting moments—I’m choosing to share bits and pieces with you. 

But if you have a question, please never hesitate to email me and ask :-) 

Love Letter To A Freelance Writer #4: You’re not risking murder, right?

Dear reader,

I have this quote framed and fastened to my wall:

Every great dream begins with a dreamer. Always remember, you have within you the strength, the patience, and the passion to reach for the stars to change the world.

This could be generic self-help mumbo jumbo until you realize it was said by Harriet Tubman. You know, the Harriet Tubman who risked a brutal murder at the hands of a ruthless slaveowner if she was caught freeing slaves on the Underground Railroad. I bring this up because there are two core tenets I teach writers:

  1. Nothing should be above the outcome your writing looks to achieve
  2. Don’t be afraid to think bigger

Many writers play small. They look around at what “everyone else” is doing and accept it as the norm. They argue their points in Facebook groups about unimportant minutiae all day long instead of actually moving forward. 

I hold the respect I have for the craft of writing above all else—whatever isn’t doing justice to the piece I’m writing, I cut. The same goes for making money as a writer (if it’s not moving the needle, cut it).

Let me give you an example so you don’t just think I’m waxing poetic: if you’re creating a sales copy piece, the only goal of that piece of writing is to make a sale. Not to sound cute, not to show everyone how smart you are. Its sole purpose is to sell a product. Same goes for fiction writing. 

My two favorite fiction authors are Gillian Flynn and Stephen King. All of their writing is geared towards telling the best story possible, and… building suspense. Because that’s what they do. They’re suspense writers. Their goal is to draw you in, entertain you, and build anticipation. 

They also dared to dream bigger. Gillian went from working for a magazine, to writing novels, to now writing major motion picture films. King’s first hit, Carrie, was his fourth novel, and he’d worked low-paying dead-end jobs up until that point (you should read about both their stories; they’re fantastic and inspiring). So wherever YOU are, I’d encourage you to think bigger. 

I know it’s hard when you’re just starting out, because most of the time, all you want to know is the “secret” to making money. Well, while there’s no secret, there are a few tools that can help you (I’ll share a money-making tip in the next email). 

But what would you do if you were already getting paid to write for a living? Would you quit your job and spend a year traveling like I did? Would you keep at it on the side so you could pay off some debt before making the jump to full-time?

Personally, I used the time I got back to pursue screenwriting and filmmaking, and I run into a lot of “starving artists” who are only starving because they think that’s what they must do.

So, dare to dream big, dear reader.

- M

P.S. Nothing should come above the outcome your writing looks to achieve. That’s the way I approach any piece, whether it’s a piece of sales copy, or a short story I’m writing. 

So, question for you: What do you think this email was trying to achieve? Hit “Reply” and let me know, and I’ll share why in the next email. 

Love Letter To A Freelance Writer #5: I fell in love with a stripper

Well, technically you can’t fall in love with someone you don’t know, right? Here’s the story:

We sat in the same coffee shop every single day, and I eavesdropped on her conversations with the barista/owner (a friend of mine). I watched her raise a blade to a Mexican gangster’s neck after he catcalled her once, and after that I was intrigued by this petite bronze woman with the personality the size of the universe.

Let’s call her “Marisol.” She apparently used to be a stripper. Her past and choice of work were of no concern to me, but after listening in on her conversations, the way she chose to deal with her emotions and with the people she shared those emotions with… well, that was a red flag I couldn’t ignore. So I stayed away. Years of therapy have proved to me that people like her throw me for a loop.

But I continued my observation and funneled my thoughts into story. I wrote a short film script about a guy sitting in a coffee shop thinking of every reason why he shouldn’t go talk to the girl he has a crush on. It gets better…

There was a film competition coming up I wanted to enter, and I hoped to film the script I wrote. I only had two weeks, and the owner of the coffee shop agreed to play the male lead. So one fall day I schlepped over to the same coffee shop, walked in to talk to him about finding a female actress to play this gal, and lo and behold… she was there.

Not only that, but she now worked there and it was one of her first days on the job. John (the co-owner) hadn’t read the script, so when I walked in, he (knowing I was still looking for a lead actress) turned to her and asked: “Oh, Marisol, do you want to be in a short film?”

My eyes bulged, and my heart started thumping. “Sure, let me read the script,” she said. 

If John had read the script, he’d have known that I had taken words directly from her mouth and turned them into dialogue. And this girl was about to read a script she was written into. I had to cast her—there was no time to find anyone else. So I sent her a copy. 

I hate to do this to you, but I’ll share the conclusion in the next email (it’s worse than you can imagine, trust me). PLUS, I have a ton of stories like this I want to share with you in the future.

This is where the “most interesting copywriter in the world” handle came from. My friend and mentor, Jennifer Hudye, bestowed that title on me, and I guess I’ll run with it, but this brings me to my point for today: If you want to make money as a freelance writer, you have to be different. You MUST stand out. Otherwise, you’re lumped in with everyone else. This can be as simple as knowing more about a certain topic or niche than anyone else. Or, it can be that you’re a copywriter focused on sales conversions, who also happens to travel, make films, and falls in love with people you shouldn’t, and then you run away with a title when someone dubs you interesting. 

Also, a word of caution… don’t stand out for the sake of standing out; I’m not saying you should chase fame here. But when you stand out, your clients will respect you more, pay you more, and you’ll have an easier time achieving your goals because money will flow. I’ll share exactly HOW to do this in the future, but if you need a little refresher, check out the bonus chapter of the guide I sent you (here’s the link in case you somehow lost a digital ebook).

- M

P.S. Yes, the answer to last email’s question: the point of the email was to inspire you to think bigger. Every single sentence was geared toward that outcome. Hope it worked!

Click here to read part two (including the script I sent her!).

Or fill out the form to be notified when I publish the entire collection:

Your cart

We value your privacy

We use cookies to customize your browsing experience, serve personalized ads or content, and analyze traffic to our site.