Beyond gathering information about the project and company, the most revealing line of questions is to ask “Have you worked with freelancers before? How did it go? Were there any issues?”

In my experience, the responses will fall into one of three categories:

1. They’ve had great relationships with freelancers.
   Usually a green flag. You can follow up by asking specifics of what those freelancers did right that you should emulate.

2. They’ve never worked with a freelancer before.
   Not an automatic red flag, and needs to be viewed in light of how much business experience they have in general. Since it’s unfamiliar territory for them, be clear about expectations, timelines, and your process.

3. They’ve worked with freelancers, but there were difficulties.
   Here’s where follow-up questions are key. Ask them to describe what went wrong, while keeping in mind you’re only getting the client’s side of the story (and the freelancer might have a different perspective). For example:

• “The freelancer missed deadlines” vs. “The client gave me the source material two days before the project was due.”

• “He turned in poor-quality work” vs. “I did 15 rounds of revisions and the client still wasn’t happy.”

• “She’s too expensive” vs. “The client asked for a discount after they signed the contract.”

You’ll need to rely on your instincts to determine where you think the truth lies. Does the client seem to have an objective explanation of what happened, or is it possible that you’ll be the next in a long line of freelancers who ended up having issues with them?

Past Experience Isn’t Foolproof, But It’s Your Best Early Indicator

The earlier you can assess a prospect’s history with freelancers and get a sense of their work style and expectations, the better you’ll be positioned to decide if it’s an engagement worth pursuing.

There’s no foolproof method for uncovering if someone is easy to work with—and sometimes red flags only start flying once a project is underway. But asking these questions (and following up as needed) can give you a valuable head start on making smarter decisions and being aware of possible danger zones.

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In the comments:
Have you ever asked a prospect about their past experience with freelancers? Depending on their answer, did you end up taking the project or running in the other direction?

Last week, an author whose first book I helped publish reached out to me in a semi-panic. A friend had read his book and suggested that “using em dashes will make people think it was written by AI.” My author was seriously considering re-editing the book and uploading new files.

Mind you, two days before, he’d been thrilled at how many people had said “It sounds just like you!” (Which it does.) But one comment from one friend was enough to make him question everything, even though he knew it was his own original work.

That’s precisely the kind of AI anxiety a lot of our clients are experiencing right now. And because we’re often more familiar with AI tools than our clients are, it’s a great opportunity to be the calm, rational voice in the conversation.

Be the Voice of Reason

In this author’s case, I emailed him back to the effect of:

• I understand your concern. Em dashes being a red flag for AI has floated around since the early days of AI—because em dashes have been used forever by skilled writers, and AI trained on that data.

• Search any phrase like “does em dash mean ai,” you'll see how it's been debunked.

• The important thing is that this book sounds like you, and all the early feedback confirms that.

He immediately replied with relief and appreciation. (And as for me, I was relieved that we didn’t need to rework the manuscript to avoid the AI boogeyman.)

When Clients Believe AI Is Just as Good

A new referral client came to me frustrated with an ongoing project: generating 400-word blog posts from tedious 10-page reports. He’d been using AI, but was annoyed by the quality and the amount of editing required, so he hired me to take on the process. For every client who sees the wisdom in that, however, there are many who don’t recognize the difference, don’t understand that AI has accuracy issues, or who think Grammarly can substitute for a professional copyeditor or proofreader.

In such cases, you can try some version of: “I’ve seen AI generate decent first drafts, but you really need significant human editing to reach professional quality. That’s why you hired me, because I can refine everything with your unique voice and strategy.” If a prospect isn’t persuadable on this point, they may not be a good fit for your business.

When Clients Believe They Need to Outsmart AI

I’ve also seen clients become obsessed with avoiding AI detection, which feels similar to the old days of keyword-stuffing for SEO, except in reverse: “We need to make sure our text doesn’t get flagged as AI, so don’t use em dashes or any of the words in the following list.” The most reliable route here is—surprise—have a human (i.e., you) write it. Even so, AI detectors are notorious for false positives, and you should be prepared for that conversation too.

Be Transparent about How You’re Using AI

No need to volunteer this preemptively or to be defensive, but you should be ready if a client asks. “I lean on AI for brainstorming and background research, and also for automated transcription. But when it comes to the writing, everything I produce for you is original, based on your goals and our discussions.”

Final Thoughts on AI Anxiety

Right now, some people will believe writing is AI generated, even if it isn’t. Conversely, lots of people get fooled into thinking AI-generated text was written by a human.

As individual writers and creatives, we can’t fix either issue. To me, the best approach is a personal one: Talk to your clients honestly, and create for them with your authentic, real-live-person talents. AI ain’t there yet.

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In the comments:

• What’s the most common AI-related question or concern you hear from clients?

Last week, I saw a freelancer share the classic “good-fast-cheap, pick any two” meme. Yes, I get that it’s shorthand for “You can’t have everything.” But it’s a mentality that’s bad for your clients and even worse for your freelance business over the long haul.

I’m a fan of borrowing smart pricing concepts from other industries. The contractor who provided an estimated range instead of a firm bid for our kitchen remodel back in the early ’00s? I stole that tactic immediately. The local auto mechanic whose sign says “Rates are $XX/hour, $XX times 2 if you watch and $XX times 3 if you worked on it yourself”? That’s not too different from managing high-maintenance clients.

Three Possible Good-Fast-Cheap Scenarios

1. Fast + Good = Expensive. This is a client who’s willing to pay for quality and speed. So far, no problem.

2. Good + Cheap = Slow. Marginally useful, perhaps if it’s an interesting project to drop in the portfolio. Do this too often, however, and you’re clogging the pipeline with projects that don’t pay well.

3. Fast + Cheap = Low Quality. This is the model that inevitably ends in tears for everyone. Your client doesn’t get the results they want, and your reputation is at risk. (Important: This doesn’t include projects that you can do fast and profitably because they’re easy for you, while still producing high-quality work!)

You Can’t Sacrifice Quality or Price

For creative freelancers, the inherent problem is that dialing back quality is counterproductive (and if you’re reading this, I assume you take pride in your work).

When a client doesn’t get the results they want, they’re not going to hire you again. They may even tell other people that they had a bad experience. If their sense of taste is so awful that they’re actually satisfied with subpar quality, guess what? They’ll send you referrals from their friends who want fast & cheap slop.

Likewise, lowering your prices to get the gig is also a sugar fix, to keep you feeling busy—but there’s an opportunity cost too. You’re probably better served to spend that time marketing and finding new clients who appreciate value instead of grinding on projects that don’t pencil out. (Once again: I’m not talking about projects that are good, fast, and profitable.)

My take? It’s time to retire the threadbare “good-fast-cheap” business cliché, along with the mindset that you can sacrifice quality or price to any significant extent. Find the clients you like, respect and pay well, and then do a fantastic job for them.

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In the comments:

• Have you ever felt pressure to accept a “fast-good-cheap” tradeoff?

• What’s your approach to pricing speed vs. quality vs. rate?

A reader writes: “My freelance client asked me to consider billing 70% of my normal rate for meetings because I’m not physically working on a project during that time. The more I think about it, the less I agree. They're not paying me to click a mouse. They're paying me for my creative output. Am I missing something?”

I agree 100% with your reasoning. Every hour you invest in a given client, whether it’s interviews/research, writing/editing, or meetings/communications, warrants the same rate. Heck, if I have to drive 30 minutes to a client’s office, I won’t list it as a line item on the invoice as “windshield time,” but that time is in there.

Participating in a meeting as a freelancer is an intellectual contribution, even if you’re not processing pixels. Discounting that time trains clients to undervalue your expertise.

How to Push Back Gracefully

The fact that they asked you to “consider” it indicates they may have some misgivings about the request, and it sounds like you’re already equipped with the correct perspective to gently push back. The key is to frame the discussion around the benefit for the client:

• “I totally understand wanting to manage costs. The truth is, meetings help me stay on top of the details so I can deliver better work with fewer revisions. Because of that, I bill my standard rate for meeting time.”

• “My rate is based on the overall value I bring, not just time at the keyboard. Attending these meetings lets me contribute strategically, which saves everyone time and effort.”

Keep in mind, this can also be an opening to suggest project-based pricing and avoid the hourly-rate issue altogether: “Another option that we might consider is moving to a project rate, so we don’t need to track meetings or emails. I can build everything in and focus on delivering the project and getting results.”

Why This Matters

Clients who want you to succeed will understand where you’re coming from. Participating in meetings is an important part of the process, but agreeing to a financial distinction between creative and non-creative time sets a bad precedent. Protecting your boundaries now will be better for the long-term health of your relationship as well as your bottom line.

You’re on the right track—let me know how it goes!

In the comments:

• Have you ever had a freelance client ask for a discounted rate on meetings or calls? How did you handle it?

• What’s your policy on billing for non-creative time? I’m curious to hear your reasoning, particularly if you disagree with my same-rate-for-everything philosophy.

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There’s one low-key tactic that accomplishes both, and the formula couldn’t be simpler or more natural: Casually mention other work you’re doing as a freelancer and what kind of client you’re doing it for:

• “Your timing is great. I just finished up a whitepaper for one of my longtime clients.”

• “This is perfect timing. I’m wrapping up a website project for a nonprofit org next week and have some availability.”

• “I just finalized a series of video scripts for a new freelance client, so your timing is ideal.”

• “You caught me at just the right time. I just turned in the first draft of a sales exec’s book that I’m ghostwriting.”

I’ve used a phone call as my example, but it’s equally effective in emails or Zooms.

Tone & Timing Matter

The key is to keep your phrasing brief, positive, and relevant. The goal is to sound busy, but not so swamped that you can’t take on anything else, which is why it’s critical to mention some variant of “hey, good timing.”

Ideally, you want something that will resonate with that specific person and their needs. There are numerous ways to tweak it to any situation:

• Diversify by project type (website content/design, whitepaper, advertising copywriting, etc.)

• Change the details (new client/longterm client, industry type, etc.)

• Switch up the timing (it works mid-call or even as a closer, but only do it once per call/email)

Why This Tactic Works So Well for Freelancers

There are several reasons why this approach is so effective:

• It positions you as experienced and in demand without bragging.

• It subtly offers social proof.

• Most important, it expands the client’s view of your capabilities.

The truth is, creatives tend to get typecast. Even long-term clients and referrals may have you pigeonholed (“She’s our website copywriter”) without realizing that you offer a much wider range of services.

Work this simple phrasing into your approach, and you’ll be stunned how often you’ll have a “Oh, I had no idea you do that too!” moment.

I can’t begin to count how many times it’s paid off for me in the past 20 years, in new projects, upsells, and referrals. One example: I mentioned that I’d just edited a book to a prospect (a motivational speaker), and he responded by asking if I could help him write his own. That conversation turned into a nice ghostwriting gig.

A single targeted comment in the right moment can plant seeds for future work with a freelance prospect, an existing client, or someone in their network. No hard selling required.

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In the comments:

• Have you ever had a “Wait, you do that too?” moment?

• Tag a freelancer who might benefit from trying this.

What does your dream freelance client look like?

Fast payer. Steady stream of high-profile projects. Positive feedback. Referrals galore. Responsive and easy to work with.

Sounds great.

But after 27 years of running my own business, I’ve found one question that cuts through the noise:

Does my client want me to succeed as a freelancer?

Obviously, that’s the sum of all parts rather than one piece of the freelancer–client relationship. And it’s often easiest to see in conflicting behaviors, such as a client who:

• Pays well, but is consistently negative/nudgy/panicky

• Is a blast to work with, but tends to be cheap

• Provides endless referrals, but 50% are clients from hell

• Hooks you up with fantastic projects, then bogs you down in bureaucracy

Mix and match your own examples, and you’ll recognize how the negative traits often drag you down more than the positive ones boost you up. Succeeding in a freelance business isn’t just about how much the client pays you.

Tell Me the Client, and I’ll Tell You Who Sold Them

My final corporate editorial job was at a custom magazine publisher with a client base of hundreds of hospitals, banks, and luxury brands, etc. We had a dozen salespeople, and the behavior of each client was directly related to whoever sold the contract.

• Matt’s clients were businesslike and solid communicators.

• If Todd cut the deal, they’d be nice but scatterbrained, and late on deadlines.

• And if Andy sold them, you could count on them being a constant pain in the butt.

The editorial staff had no say in assignments. The clients paid big bucks, the salespeople made big bucks, and we needed to make it work. They cared about their own success. Ours? Yeah, right.

Succeeding Over the Long Haul, Client by Client

As freelancers, we’re selling ourselves every day. If you tell me who your clients are, I can tell you who you are. We actively choose, with every day and every project, how we spend our time and effort.

Over time, your success will depend on securing projects you enjoy working on, with people who respect and pay you appropriately. Anything short of that, and it’s going to be a problem. A few quick action steps that can help:

• Run a quick audit on your current clients: List green flags (mutual respect, fair pay, interesting projects, clear communications, etc.) vs. red flags (scope creep/endless revisions, slow/late payer, energy drain, etc.). Do the pros outweigh the cons? Have you addressed the red flags? Are they even fixable?

• Re-examine your positioning: If you keep attracting clients who give you headaches, what are the possible root causes? (e.g., website, pricing, proposals/contracts, lack of boundaries.)

• Don’t feel guilty about saying no: Politely parting ways with prospects and clients who aren’t a good fit frees up time for the right ones.

Sure, there are sheep-clothed wolves out there, but if you’re getting burned on a regular basis, something is awry with your strategy, not just the prospects and clients themselves.

As for me, I work best with people and businesses who include me as an essential teammate. It’s nice when they express appreciation, but they don’t even have to say out loud that they value my success, because there are a thousand indicators in how they act. In turn, the feeling of a mutually beneficial relationship isn’t the only reason I want to help them succeed, but it sure helps.

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In the comments:

• What are the client qualities that indicate to you they want you to succeed?

• What’s your biggest red or green flag?

• Tag a freelancer who needs to hear this.

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Tap tap tap. Is this thing on?

Hey there, I’m Jake Poinier, a.k.a. Dr. Freelance and author of The Science, Art and Voodoo of Freelance Pricing and Getting Paid. In addition to running a freelance writing and editing business for the past 27 years, I’ve written and presented about a wide variety of freelancing topics on and off since the early days of Blogger.

For the past few years, it’s been off. If you’ve ever worked in WordPress, you may know my pain: A website theme that slowly decays with obsolete plugins, update conflicts, and random failcode gibberish decorating the screen.

Ultimately, I couldn’t even stand to open the page for fear of what overgrown weeds would greet me, let alone creating and sending out a blog post.

Saved by Substack

What’s been nagging at me, though, is that I missed writing about the business side of freelancing. To me, elements such as client relationships, sales, and negotiation are more vital to success than how much creative talent you have.

For a hot second, I considered a redesign in WordPress. But one look at the neglected house I’d previously built, with shutters banging in the wind, was a sign from the universe that I needed someone else to be the caretaker. That’s why I landed on Substack as a solution; subtract the tech headaches, add back writing on what actually moves the needle in our business.

Let’s Talk Freelance Business: What to Expect

Back in the day, I posted weekly-ish. I don’t anticipate that changing. When I do post, you can expect topics such as:

• Persuasive ways to price and estimate projects

• Finding and retaining great clients

• Identifying and avoiding red-flag clients

• Building a durable referral stream

• Improving your business processes

• Incorporating AI into your business

• Ghostwriting tricks of the trade

• Current legal and political trends that are jeopardizing independent contracting, for which my friend and colleague Kim Kavin coined the phrase freelance busting. (Do yourself a favor and subscribe to her Substack too.)

If you’d like to see something specific, or you have a vexing client issue that needs some third-party perspective, please ping me in the comments or reply to any email.

“If you've come this far, maybe you're willing to come a little further.”—Andy to Red in The Shawshank Redemption

I appreciate you reading my initial musing about how I landed here. Going forward, the focus will turn towards improving how our freelance businesses operate—for us and for our clients.

Please consider subscribing, and if you know a freelancer who’s drowning in client drama, stuck in feast-or-famine mode, or wants to make a good business even more profitable, please forward this or share the link.

Thank you!

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