How to Avoid Dead-End Freelance Clients While Being Trusting

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Freelancers are always thinking about the next client, the next paying project. Anxiety about money (”What if I don’t have enough?”) and loss aversion (”What if the client slips through my fingers?”) can cause us to ignore yellow and red flags and repeat past mistakes. As we rush down the hall to close the deal posthaste, we skid past the room that held the obvious insights.

I’ve written before about what makes a good client “good,” and have encouraged savvy freelancers and consultants to create their own Good Client Checklist.

This post takes the idea of vetting clients one step further by passing on two principles that have served me well:

1. “When people show you who they are, believe them the first time.”
2. “Go positive and go first, and be constant in doing it.”

Principle #1 changed my life—no exaggeration.

One of my mentors, a long-time marketing executive named Ray, put it in these words:

“People show you who they are. They keep showing you who they are. You should let them.”

Several years later, I came across the same idea in more succinct packaging when Maya Angelou shared it with Oprah: “When people show you who they are, believe them the first time.”

I started making much better decisions about which clients to work with (and which ones to sidestep) after I started paying more attention to what they do than what they say.

For example, a client might say, "If you give us a discount, we'll be super easy to work with." Yet, their actions already contradicted their words:

• They didn’t give clear answers to my questions.
• They badmouthed their last freelancer.
• They showed up late to the call.

Recently, in the Freelance Cake Community, an accomplished ghostwriter and editor shared her reservations about a paid test situation: “I appreciate that the trial isn’t unpaid; however, there appears to be a lot of content to fill in for that $100.”

Various folks chimed in and said, "Yeah. Red flags. Trust your gut."

That is, believe what the potential client was revealing. Instead of looking at your portfolio and judging your skills and capabilities that way, which I might add is why portfolios exist, the client is asking you to jump through hoops, including taking a 1-hour assessment for free. Do they respect your time? Are they looking for an equal partnership? And will those dynamics suddenly change once they hire you and the relationship suddenly become satisfying, not frustrating?

Not likely. What’s likely is getting more of the same.

10 Practices to Help You Avoid Dead-End Clients

The goal here is obviously to identify dead-end and taker clients before you become entangled and miserable. These 9 practices will encourage them to out themselves so that you can confidently walk the other direction:

1. Institute a minimum engagement, meaning don’t accept projects below a certain value. This is the easiest way to minimize the time you’d otherwise spend on price-sensitive tire kickers.
2. Institute a minimum timeline, meaning don’t agree to turnarounds time of less than X days. This will protect you from clients whose urgent deadlines are a result of their own poor planning.
3. Don’t do spec work or free “test” projects. If a client needs to see “what you can do,” they can look at your portfolio. Or, they can talk to your past clients. Or, they can make a good-faith gesture and split the risk by paying full price for a small test project.
4. Require a deposit before you start the project. The client doesn’t work for free, and you don’t either. Oh, they really want to get started? Oh looky, here’s the link for paying right now with a credit card!
5. Don’t offer discounts in exchange for future referrals. In fact, don’t offer discounts at all. If a client doesn’t have a big enough budget for everything they originally wanted, dial back on the scope accordingly. The client’s budget constraints are their problem to solve, not yours.
6. Don’t jump into big projects or retainer relationships until you’ve tested the relationship with a one-off planning project. A paid audit, project roadmapping engagement, or strategy session will educate you on what it’s like working with them, not to mention save you hours of free discovery and project scoping. Vetting goes both ways.
7. Use a solid agreement. A living, breathing attorney created mine. It’s long and dense and I hate it and I love it because it’s better than Advil for preventing headaches. Maybe you know the feeling. If you don’t have a good one, find someone who does. (Moxie has one created by an attorney that is worth the price of an annual subscription, though you can still pay monthly.)
8. Tie installment payments to dates in the calendar, not to project milestones. If the project value is less than $5,000, I charge 100% up front. If it’s more than that, I charge 50% up front, 25% at 30 days, and the final 25% at 60 days. Clients cause delays as often as freelancers, and when that happens and you can’t button up the deliverables, you can still invoice when the date rolls around. The client’s shifting timeline won’t in effect be holding your money hostage.
9. People are remarkably consistent. The client who’s sloppy with communication early on will grind your gears throughout the project. The client who’s prompt, respectful, detail-oriented, and decisive early on will continue to put a smile on your face.

Keep your peepers peeled. Notice what clients do more than what they say. Let clients show you who they are.

Principle #2 keeps you positive and attractive.

Being discerning isn’t the same as being skeptical, and that’s worth mentioning because skepticism is unattractive.

If you go into conversations with potential clients expecting them to be selfish idiots, then it’s you who won’t be appealing to work with. It’s like people can smell another person’s fundamental distrust, and what’s undeniably true is that you get what you give most of the time.

Perhaps the best illustration I’ve heard for this came from a talk that Peter Kaufman, CEO of Glenair, gave to the California Polytechnic State University Pomona Economics Club. (Say that 7 times fast.)

Let’s say you’re waiting for the elevator, and when the doors open, a stranger is already inside. As you take a handful of steps, turn, and press a button, you have three choices in how you’re going to interact with this stranger:

1. You can give them an appraising look and effectively scowl.
2. You can ignore them by saying and doing nothing.
3. You can smile and say good morning.

If you go the third route, what will 90% of people do? They’ll say good morning right back. The same is true for scowling at or ignoring the other person.

Kaufman calls this “mirrored reciprocation” and makes the point that Newton’s Third Law of Motion ("For every action there is an equal and opposite reaction") shows up in social dynamics.

And with his characteristic wit Mark Twain says this is true in our treatment of animals, too: “A man who carries a cat by the tail learns something he can learn no other way.” Cats don’t like being carried by the tail. Mistreat a cat, and its claws come out.

Kaufman summarizes the principle this way: “Go positive and go first, and be constant in doing it.”

Do you appreciate it when people don’t give you a chance? When they start you at -50 rather than 0? Do you find yourself warming to folks who have a guilty-until-proven-innocent posture towards new people? Of course not. Skepticism begets skepticism. Trust spreads.

Whether or not you have a naturally sunny disposition and radiate positivity, surely your own experience confirms the truth of this principle. Mine certainly does. You usually get what you give. You reap what you sow.

To not become jaded is hard for many freelancers.

Once you go into business for yourself, you have more opportunities to get burned, not less. At this point, nearly sixteen years into my entrepreneurial journey, I’ve been lied to and taken advantage of. New clients have asked for discounts, favors, or extra work because [insert sob story or justification here] but didn’t hold up their end of the bargain.

They have broken promises and failed to pay invoices when my family was counting on the money. They have manipulated me and insisted that I was deserving of their mistreatment. It was my fault that they treated me in a way they would never want to be treated.

My point is that freelancers and consultants have good reason to be skeptical and distrusting.

Yet, leading with trust, assuming positive intent, and giving the benefit of the doubt is still an easier, more effective, and more enjoyable way to do business.

You can be discerning and notice old red flags and patterns as they remerge and extricate yourself from those situations while also expecting the best.

President Ronald Reagan became known for a phrase he learned from an American scholar, Suzanne Massie: “Trust, but verify.”

Thankfully, we’re not involved with high-stakes negotiations around nuclear disarmament, but the principle stands.

As the Mandalorian says, “This is the way.”

When you put the two principles together, you begin to see how discerning, fair, and powerful this approach to relationships can be for freelancers:

Go positive and go first, and be constant in doing it. Then, when people show you who they are, believe them the first time.

Will you still have run-ins with bad actors? But of course.

The freedom comes in setting aside self-protecting distrust and the laying down the armor of skepticism and believing what people tell you about themselves and their intentions. You trust. Then, you verify. When what they do contradicts or discredits what they said, you put more stock in their actions. You make decisions about how best to proceed accordingly. You stick to your rules and non-negotiables—project deposits, et al—and when a potential client or collaborator doesn’t agree to them, you find the nearest door.

As freelance writer Jessica Walrack learned from her mentor, “Good boundaries reveal bad relationships.”

The best part is that you don't have to judge them or cast them as the villain. You can smile and sincerely wish them the best while withdrawing from the relationship.

Meanwhile, because you’re going first and going positive with trust, you will also attract the best, most trusting clients.

This is the way.

When you’re ready, here are ways I can help you:

1. Free Money. A pricing and money mindset guide for freelance creatives. If you’re unsure about your freelance pricing, this is the book for you.
2. Morning Marketing Habit. This course will help you build an “always be marketing” practice, become less dependent on referrals, and proactively build the business you want with the clients you want. My own morning marketing habit has enabled me to consistently make  6 figures as a freelancer.
3. 1:1 Coaching. Gain clarity, confidence, and momentum in your freelance or consulting business.
4. Business Redesign (Group Coaching). Raise your effective hourly rate, delegate with confidence, and free up 40 hours a month.
5. Clarity Session. It’s hard to read the label when you’re inside the bottle. I've done well over 100 of these 1:1 sessions with founders, solopreneurs, and freelancers who wanted guidance, a second opinion, or help creating a plan.