My Regrets From 12 Years of Freelance Writing

We’re not supposed to have regrets, right?

Well, we’re not supposed to eat that second slice of cheesecake or skip the gym in favor of a good book, either, but we do it anyway.

Just me? Moving on…

Here’s the thing: I have lots of regrets when it comes to my 12-year career as a freelance writer. Most of them come from the first few years — the years when I rarely made enough money to cover the bills.

A lot of it comes back to money. Not because I wanted to buy fancy cars or high-end jewelry, but because money buys security. If you ask me, security is worth far more than any diamond ring.

If you’re starting your career as a freelance writer, I don’t want you to make the same mistakes that nearly derailed my life over and over again. I’d rather you start your career on a good note — and keep it there.

That One Project With the Client Who Stiffed Me

It might happen to lots of freelance writers. I know it happened to me.

My client hired me to ghostwrite a novel for which he’d already written a screenplay. I submitted the first chapter to him and received rave reviews.

Each subsequent installment was met with praise and excitement. I finished the novel in just three months.

The last portion of the contract involved conducting a thorough copy edit. Before I could complete that step, my client started shopping the manuscript to agents.

He received a negative response from one agent, which incidentally had nothing to do with grammar or punctuation and everything to do with the plot, and he decided not to pay the remaining $2,000.

The bastard didn’t even tell me that he wouldn’t pay. He simply stopped responding to emails and telephone calls.

Last I heard, he’d self-published the manuscript.

What I’d Do Differently

This happened a few times to me, though never again for as much as $2,000. If I were just starting out as a freelance writer, I’d demand payment up front.

Contractors and other service providers can place liens on their clients’ property and take other measures under the law to recoup funds that customers have failed to remit.

Freelance writers don’t have the same protections. We can sue, sure, but lawyers’ fees and other costs will quickly eat up any judgment we’re able to get.

Even if the client has to pay court costs, we lose time that we could have spent hustling to get new clients.

Don’t be afraid to ask for money up front. If the client expresses concern, use an escrow service. It’s all about protecting everyone involved.

Engineering My Mediocrity

One of my heroes, researcher and storyteller Brené Brown, mentioned in her second TED talk that she realized — prior to her first TED talk going viral — that she was “working very hard to engineer staying small.” I identify with that statement more than I care to admit.

I wanted to write articles, blog posts, books, and other copy for my clients. But I wanted to stay in the shadows, too.

Visibility felt dangerous. It seemed risky.

So I turned to content mills. I wrote for companies like Writer’s Domain, CopyPress, and Media Shower. I felt comfortably anonymous as I submitted thousands upon thousands of words to clients who would never know my name.

Then I decided to post my resume on LinkedIn.

Within a week, I had several offers for jobs from recruiters. And I wound up landing my dream job just three months later.

What I’d Do Differently

Staying small feels safe. It’s comfortable. It’s also the easiest way to forestall growth.

I’ve learned more in the last three months at my current job than I learned in 12 years of freelancing. That’s not to say that freelance writing didn’t result in skills developed or knowledge learned; it’s just that I prevented growth because I feared scrutiny.

If you want to make a freelance career work, you have to be willing to make yourself vulnerable. You might get rejected. You might get criticized. But you also might find what you been looking for all along.

Where I to live my freelance writing career all over again, I would have made myself more visible. I would’ve blogged, participated on social media, and not restricted myself to jobs and opportunities that felt safe.

Every Article I Wrote About HVAC Systems

There’s nothing wrong with HVAC companies. They serve a valuable purpose — I should know, considering that I relied on the services of an HVAC company when my air-conditioning unit shuddered his last breath during the sauna of the Texas summer.

But in my passionate about HVAC? Do the inner workings of a furnace system filled me with glee? Yeah… not really.

Life’s too short to write content you hate. Even if it pays the bills, it will make you resent your choices as well as the client who hashired you to create content for him or her.

Worse, your ambivalence will show in the finished copy. When you don’t have enthusiasm for the subject matter, you can’t inject any passion into the pros.

I don’t want to pick on HVAC companies. I also regret working for plumbing, electrical, general contracting, and painting companies. Those clients would have found a better writer and someone else.

What I’d Do Differently

It’s hard to turn down a paying job, especially when rent is due just around the corner. But we have to make smart decisions.

Did writing for HVAC companies hurt my career? Not in any discernible way. I turned and respectable copy and received financial compensation for my efforts.

Writing those articles, however, took away a little piece of my soul. They weren’t a labor of love — they were pure labor.

If I could do it over again, I would stick to the types of content that inspired me or interested me. Maybe I would’ve had to take a few undesirable projects to keep it on the table, but — excuse the pun — I wouldn’t have made a career out of it.

Should you turn down work because you’re not passionate about it? That’s a really personal decision. Financial stressors can force us into uncomfortable situations and demand of us sacrifices that would rather not make.

What I can say, though, is that working on projects you hate will inevitably chip away at your passion for the work, and that’s not good for anyone. Take on projects when you have to, but work toward a future where you can be more discerning.

Associated Content

Good old Associated Content. It doesn’t exist anymore and hasn’t for many years, but it was the first company to pay me for blog-style articles. When I got that first PayPal transfer for $10, I felt like I’d won the lottery.

Associated Content was a company that paid writers to produce articles on any topic they desired. The rates were extremely low, with content managers occasionally offering fewer than three dollars for a 500-word piece.

Over time, I built up relationships with the company’s partners and earned access to higher-paying work.

And I did so under a pseudonym — specifically, a male pseudonym.

The details of that story are better left to a future article, but I’ll just say that it was a revealing experience. Eventually, Associated Content was acquired by Yahoo! and eventually shuttered.

While Associated Content was not a bad company and do not deliver an overtly bad experience, it helped me feel comfortable working for content mills. Long after I stopped working for Associated Content, I worked for a dozen or more other content mills that slowly drained my passion.

What I’d Do Differently

I could have used Associated Content as a jumping-off point from which to launch a private freelancing career. After developing a portfolio of articles on that website, I might have sought higher-paying work through other channels.

Clearly, I didn’t make that decision. Instead, I stuck with content mills continued to wages far below that which my experience and skill demanded.

In my knocking content mills? No, not necessarily. Content mills put food on my table for more than a decade.

However, I think of content mills as training wheels. They help freelance writers learn how to satisfy clients in a relatively secure environment. You don’t have to market your services or manage accounting, which allows you to focus on your craft.

But at some point, the training wheels have to come off. I wish I learned that lesson years ago.

Procrastination as a Religion

I would call myself a workaholic. Some weeks, I spend more than 80 hours on various work-related tasks.

That wasn’t always the case. For years, I turned procrastination into a lifestyle. Why would I work when I could surf the Internet for pictures of cute puppies or watch “Judge Judy” reruns?

I don’t think I’m alone in this whole procrastination nonsense. We’ve all done it from time to time, and some of us are more prone to it than others. When you’re a freelance writer, it’s easy to find ways to avoid work, especially if you’re not fulfilled by the work awaiting you.

Clearly, I’m a woman of extremes. I went from procrastinating every task on my plate to working for more hours than necessary to do my job well.

Working hard and hustling, though, beats procrastination by a considerable margin.

When people say that you can’t get ahead without hard work, they’re speaking the truth. The harder you work, the more rewards you will reap from your efforts.

Maybe that’s not what you want to hear, but experiences taught me that it’s the truth. When I’m constantly working toward something and setting new goals for myself, I feel better about my job, my life, and my purpose.

What I’d Do Differently

If you gave me a time machine, I probably wouldn’t get into it. This article might be about regrets, but that doesn’t mean I want to live my life over.

I wouldn’t advise aspiring freelance writers to take my path, though. Instead, I would advise them to hustle, to push through fatigue, to eschew distractions, and to embrace every opportunity that presents itself.

A freelance writer doesn’t have guaranteed paycheck. Furthermore, procrastination puts you at a disadvantage compared to your peers.

I think that, if I had avoided the temptation of procrastination more often, I probably would’ve found better opportunities faster.

Making an Ass Out of U and Me

I’ve made a lot of assumptions in my career — often to my detriment.

Once, I was invited to meet with a publisher to discuss an opportunity. I assumed that I lacked the skill and talent to deliver what the editor needed.

Maybe I was right. I’ll never know.

Sometimes, I assumed that I understood a client’s request and later discovered that I’d misinterpreted the instructions entirely. It’s an embarrassing mistake to make.

Whether I was assuming that I wasn’t good enough, that I knew what was expected of me, or that I could handle a task that exceeded my skill, assumptions threatened to derail my career more often than I care to admit.

I don’t like making an ass out of myself. You probably don’t either.

That’s why I advocate for saying the three most liberating words in the English language: I don’t know. Try it sometime.

What I’d Do Differently

Assumptions can protect us. For example, if we assume that we’ll die if we jump off a cliff, we might avoid a grisly fate.

But assumptions can work against us, as well.

I try not to make assumptions anymore because I don’t want to miss out on opportunities or show my ass in public. That’s what I’d do differently.

When you’re faced with an opportunity or decision, ask yourself if you’re making assumptions. If you are, ask yourself whether you’re basing those assumptions on fact.

That’s where I think we go wrong. We don’t stop to wonder whether we’re making an emotional decision or a logical one.


Over 12 years of freelance writing, I made a lot of good decisions. I also made some poor choices, stepped in shit, and sabotaged my own career. My hope is that you won’t make the same mistakes.

But even if you do, there’s no mistake in freelance writing from which you can’t return.

Except plagiarism maybe. Don’t do that.

And if, like me, you have few regrets, know that you also make decisions. You took action based on the information available to you at the time. And you acted like a human being.

Some people say that they have no regrets. I call bullshit. Everyone has regrets because nobody makes the right decisions every time.

I think what people mean to say is that they don’t wallow in their mistakes. They look at missteps as opportunities for growth. Without regrets, we can never become better people or more successful freelance writers.

If you’re a struggling freelance writer, feel free to get in touch. You can reach me at I enjoy helping other freelance writers find their way.