7 Red Flags for Freelancers and How to Fix Them

by Andy Strote

If you’ve been a freelancer for more than a month, you’ve come up against red flags. What are red flags?

Red flags are warnings that you should pay attention, that something bad will happen if you don’t put a stop to it.

You often get red flags when you meet with potential new clients. They’re asking for things, talking about the project in ways you know won’t make it a success.

You might get a red flag with an existing client, but usually, you’ve figured out how you best work together and projects run smoothly.

How to Recognize Red Flags

A red flag is your sixth sense or your “gut” telling you, “Hey, speak up, say something, this isn’t right. You need to interject now before it goes any further.”

If you’re tuned in and you “see” a red flag waving, you’ll raise your hand to get your perspective out. If you let it go by thinking, it will be ok, you’ll sort it out somehow, odds are it will come back to bite you.

Red Flag 1: Taking on a Project That’s Not Right for You

You’re meeting with a potential client and they’re describing the project they want you to do.

As you listen, you realize that this project isn’t really what you do.

However, you might try to convince yourself that you can stretch your capabilities for this. After all, you want to grow, and this could be an interesting new direction. Also, there’s the money (always the #1 temptation!).

You’re a smart person and believe you can learn what you need to deliver the project successfully.

What typically goes wrong with these types of projects? You underestimate the gap between what you know and what you need for this project. What you thought would be easy turns into a minefield. Everything that could go wrong, does. Only later do you realize you shouldn’t have taken this on.

How to Fix This Red Flag: Be sure of your capabilities and the types of projects where you excel.

Also, be honest and forthcoming with the potential client. Talk about your capabilities and the aspects of their job that fall outside of them. Let them know where you’ll have to stretch to make this work. See whether they still want to give you the project.

And simply, if you know you’re in over your head, learn to say no. If you know someone who would be a better fit for the client, recommend them.

Yes, you’re turning down potential revenue, but you’re also avoiding a world of hurt.

Red Flag 2: Unrealistically Tight Deadlines

When you meet a prospect about a job, one of the first things you’ll want to know is when they expect you to complete the project.

Spend some time on this conversation. Make sure you both understand what you mean by “completed”. Is it when you turn in the first version of the project? Or is it after the client has made 100 rounds of revisions?

Does the project have to meet an immovable deadline, or could it be extended, if necessary?

Ideally, you have enough experience to mentally ballpark how long it takes you to complete a project.

If someone describes a project, and in your mind, you’re thinking, yeah, I could do it in two weeks, but the client “needs” it in two days, well, there’s a problem.

It’s not that you can’t do the job; it’s that you can’t work on it 24 hours a day.

Another thing to consider: the client may not be unreasonable in this request. Maybe, if you had a team of 10, you could do it in two days, but on your own, impossible. In that case, you’re simply the wrong vendor for this job.

How to Fix This Red Flag: Have the deadline conversation early. There’s no sense in talking about the project any further if you’re miles apart on the deadline.

Make sure everyone understands what they mean by the deadline. First deliverable? After revisions?

Understand who else, besides you and the client, might have an impact on this project. For example, are either you or the client using third parties to do some of the work? Does the project depend on their deliverables?

After you have this general discussion, let the client know that you’ll provide a project schedule with the written estimate. When they approve your estimate, they’ll also approve the schedule.

Red Flag 3: No Written Brief

Here’s where you can’t budge: you need a detailed written brief. What are you expected to do, who is it for, what information do you need?

It should all be in writing.

If a client is “too busy”, “doesn’t think it’s necessary”, or simply “can’t be bothered”, with a written brief, you need to say no.

Having just a verbal brief means you’re stuck with writing the definitions of what you’re proposing. That’s not your job. It’s theirs.

Even when you get a written brief, you need an opportunity to ask questions and get satisfactory answers.

The brief also acts as content for your estimate. You’ll want to use some of the brief in your estimate to show the client that you understand what they’re asking for. You’ll also use your estimate to define the project scope. For example, you’ll want to be clear on how many rounds of revisions you’re including and at what stage you’ll charge more.

Don’t start the job until you’re 100% certain of what’s required. Be sure you have everything you need to provide a written estimate for the project.

How to Fix This Red Flag: Like the deadline conversation, have the written brief talk early. Simply ask when you can expect it so that you can produce an estimate.

Emphasize that this is the way your company does business, and you’ll need it to start. If need be, tell them what they should include in the brief.

Don’t start without it.

Red Flag 4: Not Getting a Deposit

If you’re working with a new client, get a deposit to start the project. Make it meaningful—anything from 25% to 100% of the total project.

Many creators work this way. It’s not unusual. If you’ve never asked for it, you may hesitate. Don’t.

Again, in your early discussions, when you’re talking about schedules, written briefs, etc., include a mention of the deposit. Be matter-of-fact about it.

Here’s where the red flag comes in: the client refuses to pay a deposit.

“We don’t work that way. We’ll pay upon project completion.”

“Our accounting system won’t allow it.”

“Why should we pay anything before seeing it?’

All are bad excuses.

Not wanting to pay a deposit is a definite red flag. If it becomes an issue, think twice about taking on the project. It could be a sign of things to come.

How to Fix This Red Flag: First, you have to get comfortable about asking for deposits. Simple as that. Then you have to discuss it before taking on the job. Follow up by including it in your estimate. Once your estimate is approved, send an invoice for the deposit.

It’s up to you whether or not you start the job before you get the deposit. Some creatives are very strict about this—they begin when the deposit hits the bank. Others will start on the promise that the deposit is coming in a few days.

Learn more about money strategies for freelancers here.

Red Flag 5: You’re Not Reporting to the Project Champion

You get briefed for the job by someone who seems to be an admin assistant. The job isn’t really his responsibility; he’s just briefing you. Whose project is this? It’s hard to tell.

Your estimate goes to this admin assistant, then disappears. It takes ages before you hear back. Once you start, the same process happens.

What’s wrong with this approach?

If you don’t answer to a project champion, you’re probably responding to a committee. Count on indecision, many revisions, and the project dragging on forever.

These situations require a lot of project management to keep them on track. Be sure to anticipate that in your estimate.

How to Fix This Red Flag: You can ask whether there is a project champion, and if so, can you report directly?

If not, you need to be very explicit in your written communications. Odds are, the person you’re dealing with will simply forward it and not add much. So, cover everything in writing.

If you’re missing information, if the project is going into billable rounds of revisions, if a deadline is coming up… get it all in writing.

Otherwise, when the project goes sideways, as it may well, it’s somehow your fault.

Red Flag 6: Right from the Beginning, Something Feels Wrong

If you have a good sixth sense, and it’s telling you this potential client is sketchy, listen hard.

For example, if the client is late for your briefing meeting, is unprepared, frazzled, unfocused, full of excuses… maybe that’s a sign.

Some clients are just a mess. They can’t organize themselves or their business, and if you’re not careful, you get sucked into this vortex. It can be draining.

If you feel that vibe, you may decide this one’s not for you. Doing projects is hard enough without having to manage someone’s life.

How to Fix This Red Flag: You just have to go by your gut. Figure out why it feels wrong. If you decide to take it on, at least make sure you’re getting paid upfront and along the way.

Also, try to make more than one contact at the client. Maybe the person you’re dealing with isn’t typical of the company, and someone else will help settle the project down.

Personal example: I once took on a project like this. It turned out that the first “sketchy client” was on the verge of getting fired, which soon happened. After that, everything was fine, but there was no way of knowing that initially.

Red Flag 7: You’re Not Operating Like a Business

This one is on you. Many freelancers start working without much structure or any rules. They’re “winging it”.

If you’re in that situation, you need to recognize these shortcomings and change them.

The simplest way of thinking about it is to recognize that businesses have rules of operation. It’s the way they do things.

That includes:

  • Having templates for estimates and invoices

  • Having rules for billing, deposits, and terms of payment

  • Managing and tracking jobs systematically

  • Processes for working with contractors or other freelancers

  • A plan for your promotion and marketing

  • Having an accountant or someone to manage finances, pay bills, etc. (not many creatives are good at this)

How to Fix This Red Flag: Take a weekend to do a critical self-analysis. What could you improve about your business operations? Is this something you can do yourself, or do you need help?

Think about how to turn most of your admin tasks into systems to make them as efficient as possible. The less time you spend on admin, the more billable hours you’ll have.

Make a To-Do list and tackle it, one item at a time.

Remember, you have a business, and every business has rules. Your business, your rules.

I wrote about 7 rules for freelance success here.

I also wrote a checklist for going full-time freelance, which is handy if you’re just starting.

Learn more about identifying and addressing red flags in my book, How to Start a Successful Creative Agency. It’s the essential business guide for freelance graphic designers, copywriters, filmmakers, photographers, and programmers.

Buy Your Book Here

Over 300 pages and 23 chapters, available at Amazon (Paper & Kindle), Kobo (ebook), Apple Books (ebook), and Gumroad (PDF).

The book is packed with useful information to help creatives start and grow their business.

More Advice Than Can Probably Be Absorbed

“Contained within the book is more advice than can probably be absorbed, all learned and distilled over Andy’s long career in creative communications. It is a comprehensive guide to starting and running a creative agency. I truly wish I had a copy when I started mine.”

Ben Hagon RGD, Co-founder, President, www.forgoodintent.com

Want a free taste first?

Sure! Sign up below to get a free PDF of Chapter 14, Working With Clients.

This chapter covers essential areas such as Clients vs. Projects, Corporate Clients vs. Small Business Clients, How to Create an Opportunity Document, Benefits of Finding a Niche… and much more.

Questions? On Twitter, I’m @StroteBook. DMs are always open. Ask away.

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