Select Love Letters To A Freelance Writer Part Three

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.

You can read Part One of these selections here.

You can read Part Two here.

Love Letter To A Freelance Writer #17: A pedophile dies, and you all do this

Dear reader,

When Jeffrey Epstein, the convicted pedophile, killed himself, the internet burst into flames with conspiracy theories. 


Because we are wired to believe in secrets, especially if the situation is as bizarre as a wealthy, well-connected pedophile and pimp committing suicide after being locked up. Those on the extreme fringes need to believe he was murdered by the rich cabal of baby-eating satanists. And even the most sensible of people look at the situation and believe in foul play. Not once did I ever hear someone say that perhaps a really screwed-up person realized they were at the end of their rope and decided to kill themselves. I mean, it’s not implausible. 

But our minds constantly try to make sense of the details we may or may not have. 

Marketers and copywriters know this well. Look around at everyone who is marketing to you—secret this, secret that. Russell Brunson, the incredibly famous internet marketer has even turned this into a brand by selling his books DotCom Secrets and Expert Secrets. 

When curiosity takes over our minds, there’s not much we can do to stop it, because it’s easier for us to believe the “in” crowd knows something we don’t.

How did that person get into Stanford? How do people in real estate make money? Why do people who are smarter and better for a position get overlooked for someone who’s obviously underqualified?

It’s much more simple to just say, “Oh, they must be well-connected,” or, “They probably already come from money,” or, “The CEO probably knows their dad or something,” than to think: perhaps they’ve been studying to get into that school for decades... successful real estate agents are savvy salespeople who hustle their asses off… and maybe the person who got the promotion in the office isn’t just more charismatic, but has been following up with the CEO for six months about the job.

In our world as freelance writers, this is especially true if we see our peers accomplishing more than us, while we’re stuck wondering, “How?” When we see others effortlessly achieving what we want, we immediately think they know something we don’t. The truth is, they do know something you don’t.

But the biggest secret of them all? 

There is no secret. 

I’ve worked as a copywriter on some incredibly successful internet marketing campaigns, with some of the largest names in online marketing. I sell secrets all the time. 

When someone is selling a secret, they’re selling you a system or a process. 

But that doesn’t sound as sexy. 

If you want to make more money as a freelance writer, you have to write constantly, improve every day, find a niche, and promote yourself within that niche. There are other avenues to pursue, of course, but there is a reason you’ll hear most of the experts share some variation of this one: because it works. 

Or you could sell your soul to the satanic Illuminati cult. I’m unsure of how to make contact, but if you figure it out, let me know. I’ve got a ton of questions.

- M

Love Letter To A Freelance Writer #19: Why I don’t believe those who “don’t have regrets”

Dear reader,

“I don’t regret anything.” I’ve heard this several times throughout my life, usually from a self-righteous person trying to tell me they view everything in life as an opportunity.  And I get it. You should see failures, mistakes, and other negative events as opportunities to learn and grow. But having “no regrets” sounds like a fantasy. 

A friend of mine was drunk and hit someone with his car. She’s now paralyzed and confined to a wheelchair. He hired a good lawyer and got off with a slap on the wrist. Then he drank himself to near death because of the guilt. When he got sober, he approached her to make amends. She didn’t accept, and screamed at him through tears for an hour. Whenever we talk about it he tells me how much he regrets getting into the car that night.

Many of my own regrets center around former lovers, and wondering how things could have been had I behaved differently. And because you and I are writers, dear reader, I share a similar regret you might have, of not turning this into a career sooner. 

“If only I’d started when I was 21, instead of pursuing life in the music industry, imagine where I’d be now…” 

I can look back at that time and see the lessons I learned, and experiences that shaped me. Still, it doesn’t mean I don’t regret getting a head start on what it is I do now. Don’t let regret define you, but don’t deny it either. And don’t let it stop you from taking action on your dreams—however small they may seem—right now. Don’t let today be next year’s regret. 

- M

Love Letter To A Freelance Writer# 20: The guilt of a young mother’s bastard son

Dear reader,

My mother had me when she was young, around 20. We moved from LA to Milwaukee after my parents split, and all the moms at my new school were much older than her. They used to judge her—I could feel it. 

The way their leering eyes felt when they saw me, and the confusion I experienced when they wouldn’t allow their children to coexist with me has never left. To this day, it shows up in my relationships. When people judge me, or try to make me feel small or stupid, the urge to protect myself and my mother immediately comes to the surface, which leads me to act out in various unhealthy ways. But that doesn’t mean I am not judgmental myself. 

We are ALL guilty of judging one another. And nowhere is that more evident than in a newbie’s freelance writing portfolio. Because we know we’re being judged, and we want to make sure we can “wow” the people we want to work with. How? Well, you’ll get different ideas from different people. I was able to scale to $5K a month without a website, and while I don’t recommend it, here are a few ways I DO recommend you showcase your work:

  • Simple portfolio - You can use a Google Doc portfolio. It’s not the greatest, but it gets the job done.
  • Google Drive - When I first started, I would write up my samples, export them as PDFs, then host them in a Google Drive folder. Much less going on here, but I made $500-$1000 a month this way before I moved onto more aesthetically pleasing options.
  • Contently - This is a free tool you can use to gather articles you’ve published and put them all into one place without needing a website. It’s more for those of you looking to write for publications, but if you write your samples on, you can store them here. Boom, instant portfolio.
  • Website - A great option for those who are tech savvy, or  who want to move up the value chain by looking “legit.” However...

The problem here is most people get themselves stuck at this step; they become so wrapped up in trying to be “perfect”—or they succumb to tech overwhelm—they give up. When you’re just starting, pick something you can get done quickly, then move on. Please. 

Don’t linger on this for fear of judgment. Seriously, you can come back and change it later. Just like the behaviors that were born from childhood fears—those I can change now, too. 

- M

Love Letter To A Freelance Writer #21: Stepdad never hit me, but he did do this

Dear reader,

When I was younger I was afraid of my stepdad. He wasn’t abusive, but there was something “off” about him. He’d actually been abused in unimaginable ways himself (hit with hot objects, tied to heaters), and I always admired that he tried so hard to break the chains of trauma that bound his heart. But he never did.

Anger always lurked under his gentle demeanor, and I was never afraid that he would burst and lash out—I was afraid because there was always the risk that he could. There were times when he got mad, and I could see in his eyes he wanted to strike me. He never did. 

Instead, he doused his pain with booze and drugs that—years later—unearthed the mental illness hiding inside him like a piece of bad code. Last I heard, he was homeless living on Venice Beach. 

The reason I bring this up today, dear reader, is because I recently rediscovered Stephen King’s IT series. Pennywise The Dancing Clown is an image we have burned into our minds thanks to Mr. King’s influence on popular culture, but what’s so brilliant about the story is the symbolism. “IT” is just a symbol for our fears, and the characters are all on a journey to conquer their own. Overcoming trauma is the basis of that story, and the story of my stepdad succumbing to the power of his trauma is difficult for me to revisit—it’s something I’m constantly trying to get over myself. 

Whenever I write, I keep the biases and the experiences of the people reading my words in mind. We all have traumatic events that have shaped us, and these bubble up to the surface and create blocks that keep us from what we really want in life. 

It’s my job as a copywriter, teacher, and storyteller to empathize with these moments, because I know when I’m sitting across from a writer who wants more for themselves, suppressing their fears won’t save them. Whatever “stepdad moment” is holding them back, is similar to those moments you and I both have as well. 

If you’re at a point where you constantly feel a rush of fear or frustration with your current status… Question it. Ask, “Where does this come from?”

The answers aren’t always so obvious, but when it comes to making a living as a writer, there are plenty of dancing clowns to kill. When you’re ready, I’ll be here. Until then, keep writing, friend. 

- M

Love Letter To A Freelance Writer #22: Homeless stepdad shows up to Christmas

Dear reader,

My homeless stepfather once showed up to my mother’s house on Christmas unannounced. He was skinny and pale as bone, and his clothes were covered in filth from living on the streets. He went into the kitchen and began to yell obscenities. I looked around the room at my startled family members, and it became clear I was the one to get him out of there. 

I went into the kitchen, sat down at the table, and said, “I need you to leave. I can take you wherever you want to go, but if you don’t leave with me, I’m going to call the police.”

We left and I drove this man—who once provided for my mother and siblings, and honestly did the best he could with the hand he was dealt—down Sunset Boulevard. I looked over at him and asked if he needed anything.

“Floss, and some beer,” he said.

So, I stopped at a liquor store and bought it for him. I didn’t even care that I was buying him alcohol. After I got back in the car I asked, “Okay, where do you want me to take you?”

He told me anywhere would do—he didn’t have a place to go. 

I dropped him off on the street a mile away, and he shamefully walked away. Then, I drove up a few blocks, around the corner, parked, and started bawling. 

How could you not?

In the last email I sent, we talked about fear. I believe hope and love are at the opposite ends of fear. If, through my writing, I’m able to take someone from their fear to a place of hope and love, I feel like I’ve won. In the age of media we’re in now, fear drives the ship. We’re shown images that anger us in order to grab our attention so we might click and join in on the arguments the world is having. 

But what about hope? What gives you hope? What would make you love your life? For a freelance writer, hope may look like knowing there are clients out there who want to pay you well, and provide you with enough money to have the freedom to do what you please. It might just be the satisfaction of knowing you write for a living. 

Love may come from knowing you’re helping someone spread their message. Do you know what it feels like to hear your writing has radically changed the course of someone’s business or life? There’s nothing like it. 

What I took away from that day with my stepdad was hope. At that point, I had been sober for about four years. I knew I was on a different path, and that what plagued him no longer plagued me. I held onto that hope in the face of my fear. And now I live a life I love. That can be you, too. Just remember to live on the opposite end of that fear. 

- M

Love Letter To A Freelance Writer #25: The love you feel when breaking up

Dear reader,

There’s nothing quite like the effects of heartbreak. It’s an intangible feeling that can’t be defined—all we know is it fucking hurts. 

Yes, recently I broke up with someone, and although it was as amicable as we could allow it to be, and we both knew the relationship was not working, that heavy sense of sadness enveloped me for days. 

So what did I do?

I took a stroll down to the neighborhood coffee shop I frequent, sat in “my seat” (the one tucked away in the corner) with a pen n’ paper, and I wrote. I thought back to all the nice things we’d done and the positive qualities I admired in her, and I jotted them all down. Then I got up and handed John, the barista, a $20 bill and said, “Can you buy the next few people who come in here a drink on me?”

He agreed, and I left. 

Later that week, I returned to the shop, and a patron who received one of those free drinks wrote ME a card. It felt nice—nice to process the positive feelings, nice to do something kind for strangers, and  nice to receive an expression of gratitude back. 

Similarly, the same goes for helping a business spread its message and generate customers. The love I feel when I get an email from a client who says they sold out their event with my help, or that I nailed their voice and they now feel they have a true representation of themselves… well, that feeling is second to none. 

Love ALWAYS conquers fear and sadness. 

If you’re afraid of what the next level in your life looks like, just remember the love you’ll feel when you get there. Life, love, work, family, relationships—these things carry with them a heavy load of challenges and setbacks, many of which will hurt, a lot. But even though you can’t cure heartbreak by giving away free coffee… it sure does help. Look for the love when things get dark, and as always… Keep writing, friend. 

- M

Love Letter To A Freelance Writer #28: Female hacker tracks her mom, the murderer

Dear reader,

Imagine for a moment your marriage is falling apart. You come home to a significant other who you feel like you barely know anymore. They’re resentful at you, because you work too much. And they’re right. 

This is Heather’s story. 

She’s a talented NSA hacker whose family is falling apart—her daughter can’t even look her in the eye, and her husband aggressively scolds her when she comes home late because she’s a workaholic. 

So when her boss gives her a new assignment, she takes it on the condition that it’s her last so she can at least try to fix her family. But… that assignment is to track down and stop a murderer that might be her own mother. 

You see, her mother is a Senator leading her own investigation—one looking into suspected crimes by the CIA and NSA. As mother and daughter both continue to dig, they realize they’ve been pitted against each other unknowingly. Up until that point, their relationship is great. They abide by a no-talking-about-work-at-home rule, and Heather leans on her mom when things get rocky with her husband. But the inciting incident that sparks Heather’s investigation is the murder of a CIA agent who met with her mom the night before his death.

So now Heather has to help track down and stop a murderer—who begins to pick up her scent, and tries to take Heather out, too—while trying to prove to herself it's not her mom. And on top of that, her journalist ex-boyfriend comes back to town to cover the story, uses her dissatisfaction in her marriage to seduce her, and secretly records their sexual encounter to blackmail her into working with him. So with her husband using her daughter to guilt her into giving up the work she loves, her ex blackmailing her, and her mother potentially trying to kill her… she has to decide which loving bond to break in order to do what's right.   

Sound interesting? This is the plot of the very first screenplay I ever wrote. It was one of the hardest projects I’ve taken on in my life. And when I went to pitch, no one wanted it—I put so much of myself into this story, only to be rejected. But the day I became a writer wasn’t the day I looked at my tax return and realized I had made more money that year from writing than I ever did at my previous job. 

No, that day was when I decided to write the next screenplay, regardless of the rejection. Then I wrote another after that. Then, I decided to write and direct my own film.  And even now, I continue to write and improve on the craft. When I realized I would do for free what people pay me to do for their business, was when that shift from “Am I real?” to “Hell yes I am” happened. 

I still grapple with “being a writer,” but now that I’ve watched words that have made their way from my brain, to live a life of their own, whether that’s in a movie or a campaign that’s made my clients tens of thousands of dollars… there are fewer excuses for me to say I’m not a writer. The question I was asking of the reader in my story about Heather was this:“What if someone you loved tried to use that love against you?”

What she comes to accept at the end is that she’s used her own love (of work, freedom, etc) against herself, which leads to much more drastic consequences in her life. 

Most of us blackmail ourselves. Sure, we’re in a constant state of dramatics with the other people in our lives. But when it comes to manipulation, denigration, and outright torment? We do that most of all to the person we see in the mirror. Most of us are good people who treat others well, except for ourselves.

What about you? Are you using your own love against yourself? Don’t put yourself down, dear reader. If you don’t feel like a real writer yet, it’s natural. There will come a turning point, though, where everything clicks. You just have to stick with it, and I promise you will—like Heather—realize that external entities don’t define you. 

YOU define you. 

- M

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