My Ideal Client Became My Worst Nightmare: 5 Lessons For Freelancers

It’s easy to fall for an ideal client and get wrapped up in the promise of a potential fairytale business relationship.

Becoming your own boss can be exciting. You never know what will happen or who you’ll end up working with.

Photo: David Nguyen, freelance Music Marketer at D4 Music Marketing | Source: Courtesy Photo
Photo: David Nguyen, Music Marketer at D4 Music Marketing | Source: Courtesy Photo

After years of handling online marketing for local small businesses, I decided to pivot and help musicians with their marketing. Except I knew nothing about the music industry.

My lack of experience didn’t matter. I’ve always been passionate about supporting independent artists so I’d learn along the way. After all, I credit music with having saved my life when I was a youth dealing with mental health issues.

Despite venturing blindly into the music industry, my journey has been surprisingly great so far as a music marketing freelancer.

My highlights in my first few years include:

  • Flying first class to Japan to work tour with a Jazz legend
  • Documenting my client perform for the incarcerated at San Quentin State Prison
  • Hanging out at the LA home of hall-of-fame songwriter Allee Willis (RIP)
  • Contracting my dream musician client, only for him to become a nightmare

This is what I’ll focus on: that one problematic client. Let’s call this guy Richard. Work with Richard started off well enough. But after a rough year, I finally came to terms with reality: he had turned into the worst client ever.

It made me rethink how I’d been operating as a freelancer. I’ll share with you 5 lessons I’ve learned from this experience.


1. Establish a firm policy

I mainly operate on a monthly retainer model. It’s the most efficient way for me to conduct online marketing services. There’s no need to track hours, and I have a consistent income. One of the perks I offer such clients is priority treatment over those who pay for one-off projects.

For a while, I didn’t have a firm policy in place. Instead, I took the figure-it-out-as-I-go route.

When it came to Richard, I was lax about how I operated. Business aside, I have been a huge fan of his music for over 15 years and I got to know him on a personal level. It didn’t seem necessary. Even when he wasn’t paying, I gave him the benefit of the doubt and continued to make his work as a priority.

My compassion ended up biting me in the end. After several missed payments without explanation, I finally pushed Richard’s work aside and took longer to respond to him. This felt like a fair policy.

He accused me of slacking and being “too nonchalant.” He used that perception as an excuse to continue not to pay me! I explained that I had clients who did pay consistently and on time. It wouldn’t be fair to them for me to give Richard, a non-paying “client”, priority because that would take away the time they’d paid for. By this time, there was no reasoning with him. It was too late.


2. Communicate boundaries and expectations

It’s important to tell your clients what they can expect from you, and what you expect from them.

Richard waited until the last minute to get anything done. Which meant that I became a victim of that same habit. I was asked to do a lot of work within impossible timeframes.

As a professional, you need to set boundaries and communicate them. Otherwise, some clients will trample them. As for expectations, those must be laid out clearly. Tensions can arise when both parties aren’t on the same page.

One of my most important policies is that I don’t work for artists, I work with them. I’m not someone you pay to do a bunch of things without your involvement unless specific tasks require it. Richard had certain expectations that I never agreed to when it came to certain tasks, which he could use to justify why he shouldn’t pay.


3. Problems stem from poor communication

We can’t control how our clients communicate, but we can control how we communicate. I failed to do that with Richard, and while I lost time and money, I gained knowledge through that experience.

Things may have been different if Richard would have told me upfront that he had issues paying me a monthly retainer. I could have better communicated what my expectations were, as well as outlined my personal standards when it came to doing business.

But my biggest mistake: not warning Richard that I was stepping back from his work due to lack of payment. I’m not a confrontational person, so I chose passive aggression. While that can be satisfying, it’s rarely the proper way to handle business.


4. Be clear about payment expectations

Even though things didn’t work out, I still believe Richard’s a good person; he was simply terrible with money and conducting business.

However, I could have handled the situation better myself.

He never paid me. Surprise! Well, he did the first few months, then payments became sporadic until they stopped.

I would come to learn that Richard felt a retainer model wasn’t fair because he didn’t “need my services constantly”. Had he brought this up in the beginning, I would have accommodated him. That’s the tragedy of poor communication.


5. Know when to go

No one wants to lose a client, especially if it’s someone you’ve admired for so long. At the end of the day, if they’re stiffing you, being difficult, or not respecting your time, you need to move on.

I found that it’s never worth keeping toxic clients at the expense of your self-respect, no matter how famous or accomplished they are. Knowing your worth and respecting yourself will go a long way. Let them go.



It’s funny how negative experiences can stand out more in your mind than your greatest accomplishments. It doesn’t need to be that way. And you don’t need to work with your dream-turned-nightmare client to figure out how to better operate as a freelancer.

If this ever happens to you, don’t hold any grudges or resentments. We often don’t know what clients are going through in their personal lives. It’s best to move on and let it be. Forgive, forget, and focus on a brighter future with better clients who respect and appreciate you.


David “D4” Nguyen is a freelance music marketer and content creator for D4 Music Marketing, an online resource he created to help emerging independent artists improve their chances of making a living off music. As a non-musician, his interest in music is fueled by its power to connect us and change lives for the better, as it did for him. 


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