On a different day, I might have titled this piece: How to be a stupid freelancer. But that’s not where I’m at anymore and that’s not exactly what people want to learn. In fact, according to my search history, people want precisely the opposite. At this moment, I could share links to no less than 101 articles and posts and inspirational quotes on How to be the best freelancer ever because it’s easy and fun and you can do it from anywhere, anytime, even in your pajamas—YAY! (Yes, I’m looking at you, Pinterest.)

But the reality of being a freelancer has little to do with those top-10 lists and inspirational quotes. They are shareable but they aren’t really how we learn or improve. More often than not, we learn the hard way; we learn from fucking up and doing things wrong. In the end, we learn how to be good, smart Freelancers precisely by being bad, stupid freelancers first. We panic when money is scarce and make bad decisions. We grasp at straws when communication breaks down. We overcommit and under-prepare and blunder our way through endless seas of Red Flags because we either (a) don’t know any better or (b) don’t have the time, energy, or experience to navigate them successfully.

And I can check pretty much all of those boxes. I made all those mistakes but I survived (thankfully) and was able to learn from each and every one. And that’s what I’m here to share with you—the ways in which I have been a stupid freelancer and the important lessons I’ve learned along the way. The examples and insights below all stem from a time of scarcity—a time when the good ship Morgan was stranded in the doldrums; my sails were slack in a windless sky and there was little hope on the horizon. So I panicked and made some stupid decisions that ultimately led to me suing a client in small claims court. And let me tell you—that is something I wouldn’t wish on any freelancer, smart or stupid.

Sailing in a sea of red flags

For myself, and for most freelancers, new clients come through referrals. This experience was no different. My husband was embarking on a new project and his client was also in need of some freelance work. So, naturally (as my number one fan), my husband recommended me to the client. He didn’t really know this client that well, but since I trust my husband by default, I trusted this client too. That was a mistake.

Lesson 1: Working with family and friends (and friends of friends) can get weird

Early on in my freelance career, I worked for all sorts of friends and family. I think a lot of freelancers start out this way. I was excited to be working with people I knew and naively thought it would all be the magic, happy, funland that the internet led me to believe. Nope.

Nope, nope, nope.

Almost every project in those early days ended up being more hassle than it was worth. And each one left me liking one of my friends or family members a little less than I had before. There was little-to-no money involved, boundaries were constantly blurred, and “simple” requests were anything but.

Since my husband connected me with this new client, I treated the client as if he were a friend or family member too. I somehow forgot (or ignored) all of those earlier struggles and I threw my regular processes (and contract) out the window. It was a stupid mistake. Because—just like it had happened countless times before—very little money was exchanged and communication was anything but clear. I remember recognizing all of these familiar red Flags but I consciously chose to ignore them because, for some reason, I thought this time would be different.

It wasn’t. It almost never is. “Keeping it casual” doesn’t make things easier; it makes things harder. Just because you know someone, doesn’t mean they can’t take advantage of you.

Regardless of any existing relationship, no matter how much you trust or like (or love) someone, in order to be a smart freelancer you need to treat everyone the same. Friends, family, and friends of friends are no different than any other client. Approach the relationship with the same reservations, rules, safety nets, and emergency exits. Be just as clear and cautious as you would with anyone else. Have your processes buttoned up tight and make sure all your terms are documented, highlighted, checked, re-checked, and signed in blood by both parties. (Okay, maybe not in blood.)

Lesson 2: Pay attention to red flags

It should come as no surprise that those red flags came back to bite me in the ass. The client questioned my rates and ignored our timelines. Communication was condescending, demanding, and at times, downright rude. The client’s general attitude made it quite clear they didn’t understand or believe in the value of what I was offering. My work was merely a business expense, not something that would help them achieve their goals or propel their business forward. These are the kind of things that happen when you ignore red flags.

But how do you know a red flag when you see one? For some of us, red flags are often a gut feeling. For others, they’re experiences or interactions that seem a little off or that leave a bad taste in your mouth. They are any kind of warning that pops up during an experience with a client. They are meant to get your attention and alert you to potential danger. They are like the red flags you may see on the beach alerting you to sharp rocks or a riptide—they wave their proverbial arms in the air and shout: “Yo, you might have a problem here! Be careful! Pay attention!’

Some of the most common red flags to be aware of (particularly for freelancers) are things like:

• Communication that’s rude, offensive, or outside of normal working hours; communication that comes through non-business channels.

• Rushed or ignored timelines (which can indicate that people don’t have an understanding of what’s involved in their project or don’t value your time).

• Money issues. Listen—everyone has a budget, whether it’s a hard number or not. If a client doesn’t want to share their budget with you, that’s a problem. Talk about money openly and honestly right from the beginning.

• Promises of exposure. (See above—everyone has a budget.) Exposure is for cameras; freelancers get paid in cash. Plus, you’re going to get exposure anyway. People will see your work when it’s done. That’s not why you’re doing it. You’re doing it to get paid. Exposure is a bonus.

• Unresponsiveness. If you’re experiencing delays before the project even gets off the ground, consider that a blaring red siren on top of a pile of red flags. This is a clear indication of the client’s level of commitment and how you can expect the rest of the project to go. (Poorly.)

• Bad previous relationships. If the client has had bad experiences with freelancers in the past, they are probably going to enter your relationship with some big walls built up. And regardless of your skills and experience, they will be skeptical of you and your work from the get-go. Find out what happened in the past, work together to understand why it happened, and identify the client’s role in whatever went down. Then decide whether or not you want to proceed.

• Refusal to pay a downpayment. Always take a downpayment on your projects. Always. If a client doesn’t want to pay a downpayment, simply walk away. Thanks, but no thanks.

This list is not exhaustive. There are likely other red flags you will encounter. And to be a smart freelancer, you need to get into the practice of talking to your clients openly and honestly about the red flags you’re observing (or feeling) and why they are of concern. However, you also need to understand that what looks like a red flag to you might just be the way they have always done things. It’s your job to discuss those situations—actions taken, assumptions made, expectations unspoken—so you can better understand each other. Then, together, you can outline how you will address those red flags if and when you see them.

These kinds of conversations may feel awkward or uncomfortable at first, but they ensure that everyone is aware of the warning signs and is in agreement about what to do when you spot them. Over time, you’ll find that doing so leads to more successful projects and to better relationships with your clients. And if you’re feeling extra keen, you can even take your red flag observation skills to the next level and create a go-no-go list. This will save you a lot of time and grief down the road. Simply write down a list of the things you’re not willing to accept in any client relationship and check it at the start of each new project. Pin it on your wall. Make it your desktop background. Tattoo it on your forearm. (Okay, maybe not that last one.)

Lesson 3: Deal with red flags before you move forward

You know the old saying, where there’s smoke, there’s fire? For freelancers, red flags are very much the smoke. If you’re noticing signs that something is wrong—if your gut is telling you something isn’t quite right—you need to act like your life depends on it. Figure out where smoke is coming from and react accordingly or else you and the project will go down in flames.

Red flags, like wildfires, should be dealt with quickly and carefully. They require extra attention. For smart freelancers, this often looks like contract clauses, work-back schedules, and very clear language about payment and communication which is then reviewed with the client and signed off on. All of it. A really smart freelancer might actually respond with some polite no-thank-yous and quick, confident exits, saving themselves from a project or client that didn’t make their go-no-go list.

But I was a stupid freelancer. I did none of those things. In spite of all those red flags (and without a contract), I got to work. And one by one, all those red flags revealed fires that I had to hastily try to put out. Red flags are not just warning signs. They are important indicators of where you need to make extra provisions to protect yourself (and your time and your money). Noticing them is only the first step. The second and much more important step is to deal with them before you move forward.

Imagine that you are looking to get a life insurance policy. But you’re a heavy smoker, you don’t exercise, and you have high cholesterol. In the eyes of the insurance company, those are some pretty big red flags. They suggest that you are at a higher risk of heart attack, diabetes, and lung cancer (among other things). So as such, the insurance company deals with those red flags by tripling the cost of your life insurance policy.

Treat your freelance projects in the same way. When clients and projects present with these kinds of glaring red flags, don’t assume things will be fine. Yes—it’s much easier to just cross your fingers and hope for the best. But if you want to be a smart freelancer, add in extra provisions—time, details, money—and make sure you CYA (cover your ass). It’s natural to expect the best from people. But to set yourself up for success, you also need to prepare for the worst.

Look out for number one

You should now have a better sense of how to navigate red flags when you’re kicking off new projects and getting to know new clients. But that doesn’t mean you can sit back and get comfortable. You still need to actually do the work and deliver whatever it is you promised. And to ensure smooth sailing, there are a few other things smart freelancers need to look out for—just because you and your client start on the same page doesn’t mean things will stay that way. As the project unfolds, you need to make sure you keep looking out for number one. Which leads me to…

Lesson 4: Never send physical deliverables before receiving payment

Freelancers work hard to design and create and build things that other people need. We invest our time and money in things like education, tools, and space—things that clients don’t see and often take for granted. Even if what you have been hired to do isn’t completely tangible, there is always some type of deliverable associated with it.

That means you need to clearly outline in your contract that you will only provide deliverables upon receipt of final payment. This is something you need to be vocal and adamant about. I wasn’t particularly smart or strong when it came to payment and that is one of the biggest reasons why I ultimately ended up in small claims court.

Without a formal contract, with boundaries breached, and after communication had broken down, I chose to provide deliverables with the hope that I could quickly wipe my hands of this project (and this client) on my way to the bank. At this point, it should come as no surprise that I never made that trip to the bank. Instead, the client wiped their hands of me (after pocketing both the deliverables and my payment).

Freelancers work on specific projects or for a specific amount of time, for which we receive payment in exchange. People and organizations that employ freelancers almost never invest in the freelancer’s healthcare, education, physical space, or tools. So payment is more than just monetary compensation—it’s also a sign of trust, good faith, and commitment. That’s why mart freelancers require payment prior to providing physical deliverables (and often at several points during the course of the project). They expect us to do the work and we expect them to pay for it. Good clients understand and accept this arrangement.

Make sure the payment schedule is fair, accommodates your needs, and is agreed-upon and signed-off-on by all parties. You can make it time-based or it can unfold according to milestones—whatever works best for you. But once you sign that contract do not make exceptions. If you need to rewrite the contract, fine. But they don’t get what they want until you get what you want. You have to look out for number one.

Lesson 5: Don’t make important decisions from a place of scarcity

Smart freelancers need to remember that payment is always an end goal, regardless of how important money is or isn’t to the way you live your life. This is your livelihood. If you’re not making money, you have a hobby, not a job. We all have to ride the waves of the freelancing sea—often, we go where the wind takes us. There will be periods of abundance (strong trade winds pushing you toward prosperity) and there will be periods of scarcity (stagnant, frustrating doldrums trapping you in one place). Smart freelancers need to understand and accept that both are inevitable.

Scarcity can cause us to do and say stupid things. I trusted someone I didn’t know, I questioned my own processes to keep a cagey client happy, and I second-guessed my rates because I was getting desperate for work—any work. It’s easy to get scared when the winds die down, when projects finish up, and when leads run dry. But when we get scared, we get desperate and reckless, we make decisions too quickly and without thinking about the consequences. Trust me. I know.

When your income shrinks and you’re overwhelmed by the big gaps in your schedule, it becomes easy to think that doing whatever you can to fill those gaps is the solution. But smart freelancers know that those small projects that promise to be quick and easy are usually anything but. If we let our guard down and start saying yes to everything and anything, that behaviour quickly becomes normalized for us and for our clients. We end up fielding a barrage of “Can you just…” and “Could you quickly…” and “All we need is…” requests from clients who are only used to hearing yes.

And the worst part is that this fear only entrenches and perpetuates the situation. It forces us to keep taking on these overbearing clients and under-paying projects. It’s natural to worry about being able to pay the bills or to fear that the dry spell will somehow become permanent. But smart freelancers understand that you need to prioritize both staying afloat in the short term and sticking around in the long term: Where do you want to be in the future? What do you want to be doing a year from now? Who do you want to be helping? And does this client and/or project help you get there?

The answers to these questions will help keep you stay focused on your needs as much as the needs of your clients. Saying yes can become a habit. Try to replace that habit (or at least balance it) with the habit of asking yourself the kinds of questions listed above. It will help keep you focused on where you want to be and how you can get there. Of course you should do what you need to do in order to get by, but don’t forget to look out for number one. Sometimes finding the right clients and projects can require learning how to say “no” to the wrong ones first.

Lesson 6: The path to being smart is lined with moments of stupidity

In order to learn from our mistakes, we have to also learn why those mistakes happened. This is the most important lesson I can impart to you. We all stumble and fall from time to time. It takes strength to survive and to get back up and try again. But it takes smarts to learn how not to fall in the first place.

For a long time, I just kept sailing blindly through this sea of red flags because I didn’t give myself the time or space to map a different course for myself. I was too busy compensating for all the mistakes I was making to be able to learn from any of them.

Employees elsewhere get constant feedback from bosses and colleagues; they have annual reviews and check-ins. Just because we don’t work in a big company doesn’t mean freelancers don’t need those things too. So take the time to reflect on your work life. Look at yourself in the mirror and figure out what’s important to you. Schedule yourself time to reassess where you’re at and where you’re going and how you want to get there. And be willing to ask yourself some hard questions about what you want, what you’re willing to tolerate, and what lines you will not cross.

There’s a lovely quote (that’s often misattributed to the playwright George Bernard Shaw) that goes “success does not consist in never making mistakes but in never making the same one a second time.” And to me, that’s what being a smart freelancer is all about.