Thriving Freelancers and Clients from Hell

What’s a freelancer’s biggest nightmare? Clients from hell! Guest Bryce Bladon shares his experience on how to cope — and how to avoid problems from the outset.

If you haven’t checked out Clients from Hell yet, you’re in for a treat. This entertaining blog pulls together anonymous stories about those clients who give us aches and pains.

In this 28-minute episode, Bryce and I talk about:

  • Why Bryce sees freelancing as an amazing opportunity — for the right people
  • What’s great (and not) about freelance life
  • Bryce’s problem with “aspirational freelancing,” and what he did to combat it
  • Two recommendations for staying out of problems with clients
  • Bryce’s thoughts on the wisest way to get started with freelancing

The Show Notes

  • If you’re ready to see for yourself why over 201,344 website owners trust StudioPress — the industry standard for premium WordPress themes and plugins — swing by for all the details
  • For our freelancing friends — I wrote this for you to share with potential clients and help them see why they need you! 5 Situations that Demand You Hire a Professional Copywriter
  • — be sure to check out the resources and podcast as well
  • Bryce’s free email course answering the question, Is freelancing for you?
  • I’m always happy to see your questions or thoughts on Twitter @soniasimone — or right here in the comments!

Thriving Freelancers and Clients from Hell

Voiceover: Rainmaker FM.

Sonia Simone: Copyblogger FM is brought to you by the all-new StudioPress sites. A turnkey solution that combines the ease of an all-in-one website builder with the flexible power of WordPress. It’s perfect for bloggers, podcasters, and affiliate marketers, as well as those of you who are selling physical products, digital downloads, or membership programs. If you’re ready to take your WordPress site to the next level, see for yourself why more than 200,000 website owners trust StudioPress. You can check it out by going to Rainmaker.FM/StudioPress. That’s Rainmaker.FM/StudioPress.

Well hey there, welcome back everybody. It is so good to see you again here at Copyblogger FM, the content marketing podcast. Copyblogger FM is about enduring content marketing trends, interesting disasters, and enduring best practices, along with the occasional rant. My name is Sonia Simone, I’m the Chief Content Officer for Rainmaker Digital and I like to hang out with the folks who do all the hard work over at the Copyblogger blog. You can always get additional links, resources, the complete archive for the show by visiting Copyblogger.FM.

I am super tickled and delighted today and I would highly recommend, if you would like to raise your blood pressure with something other than politics, just kind of make a refreshing change of pace, I have to recommend you check out The stories are … They’re engaging, they’re enraging, they’re hilarious, they’re painful, and I’m so glad that we managed to convince their Editor in Chief, Bryce Bladon, to come today and talk with us about Clients from Hell. So Bryce, thank you, thank you for being willing to show up, and we would love to hear more about your site.

Bryce Bladon: Sonia, thank you so much for having me. The site is, it’s all in the name there. It’s anonymously contributed stories of horror and humor from people working on the front lines of the freelancing industry.

Sonia Simone: It’s amazing. I haven’t been a freelancer for a while and it’s amazing how viscerally these stories hit you. It’s just highly recommended. How did you get started with the idea? It’s such a great idea. What sparked the idea and then how did you kind of get it rolling?

Bryce Bladon: You know what? To be perfectly honest, and this comes up every time I talk about the site, I was not actually the original creator. I helped the original creator basically grow the site and I’m still with it. It is built on that foundation of commiseration and these very universal experiences freelancers of all shapes, sizes, and colors have to endure in their … Well, hopefully not their day-to-day life, but some of us aren’t quite so fortunate.

Sonia Simone: Yeah, yeah. I mean, there’s even stories about contractors, like building contractors, it’s really fascinating how the same issues come up again and again for people who do very different things in their freelance life.

Bryce Bladon: Mmm-hmm. (affirmative)

Why There’s Still Room for More Freelancers, Especially Copywriters

Sonia Simone: Well, let’s … I want to talk a little bit about freelancing, because although your site does focus on interesting disasters, you’re a big booster for freelancing. You see it as a model that’s on the rise. I certainly see, I mean, in my own experience, when I was sitting around thinking about … Thinking, in my job that was not going particularly well for me, “Wouldn’t it be great to go out on my own and go freelance?” which I eventually did. I believe that you said that freelancing really is the future, especially for copywriters. I was just curious about why you think that is and do you think there’s enough work to support increasing numbers of people who are coming into that market?

Bryce Bladon: Well, oh, so many questions there.

Sonia Simone: So many questions.

Bryce Bladon: Yes, to almost all of them, I’m sure. I’m sure that will come to bite me in the butt later, but I think all of those things are things that I believe. I absolutely do think freelancing is the future. The typical nine to five, 40 hour work week … I mean, that was just basically built out of one guy’s car factory and it just became ubiquitous practice, because it made the most sense at the time. Year after year, there are just more tools empowering people to work for themselves in some way, shape, or form. Now, for most of us, and the reason we care about it is because it empowers a lot of us to write for who we want, when we want, and all that fun stuff.

When you talk about the amount of work for writers, I mean, that is always a difficult thing to quantify and I’m not even sure how you’d go about measuring that, but it’s at least been my anecdotal experience and the experience of people I’ve spoken to, that the kind of work that blends creativity and technical knowhow, like copywriting for example, is the kind of work there’s really no substitute for at this stage of where we are as a society, as a world, all that fun stuff. There’s a lot of talk about automation stealing jobs, and tools to make certain things you can do easier, but there’s really no substitute for a good, original copywriter in any shape or form.

Sonia Simone: Yeah.

Bryce Bladon: It was a few years ago where I came across the idea of pitching my services to agencies that were trying to hire a full-time writer, but pitching to them as a freelancer. There’s a whole anecdote I can tell here, but basically, I was just finding agencies. Companies, they are so, so hungry for writers of … Quality writers, at the very least.

As a result of that, it’s not a job … Typically, their needs don’t qualify for a full-time employee, but for a contract employee, for a freelancer, and in some cases even a consultant, it fits such a perfect need and I can’t overstate how good its been for my career to explore that space and to … I feel like kind of a jerk saying it right now, but to kind of take that work away from full-time people and instead of one full-time employee, who’s sitting on his hands for half the 40 hour work week, a place would hire me. I wouldn’t be quite as available, of course, as a freelancer, but I could be a very useful resource and it’s … Again, anecdotal experience, so take it with a grain of salt, but every client I’ve had like this over the years, they’ve wanted to hire me on as a full-time employee.

Sonia Simone: Right.

Bryce Bladon: They’ve wanted to keep me on. Sorry, that comes across as very braggy, but what I’m trying to underline is, if somebody wants to work with me that much, it’s probably not me. It’s probably the actual demand for the work I do, let’s be clear on that point.

Sonia Simone: Oh, Canadians.

Bryce Bladon: You’re not wrong.

Having a Good Relationship with a Client is a Two-Way Street

Sonia Simone: It’s a good quality, it’s a good quality. I will say, I have been on both sides of that desk, the freelance desk, and I think sometimes good freelancers don’t realize that it’s not only necessarily the clients who are from hell. There’s a lot of terrible freelancers, unfortunately. There’s a lot of copywriters who are not good with deadlines and there’s quite a few writers who are not too good with client briefs. They don’t deliver what’s required.

Now that’s always a dance, right? Because, sometimes what’s required is insane, so then we have a conversation. Yeah, I think for people who are professional, they approach their craft and their profession in a serious way, they have good skills and good work habits, good work ethic. Yeah, I do think the company that wants you really, really wants you and it’s usually multiple organizations. I want to … Yeah, go ahead.

Bryce Bladon: I was just going to say, I’m sorry, we’re both being too polite now, and that’s the worst. But you’re so right that there are freelancers who are from hell. I run a site called Clients from Hell, and a lot of people just assume that I must hate clients. Absolutely not, and to be perfectly honest, in my own personal decade of working as a freelancer, I’ve really only had one or two, or maybe as many as three clients I would qualify as ‘from hell.’ It’s one of those things that I don’t want to quite elevate it to a rite of passage, because that legitimizes people acting like jerks, but it is one of those things that once you’ve been burned you kind of know what to watch out for.

Sonia Simone: Yeah.

Bryce Bladon: If you do read the stories on my website, you will absolutely know what to watch out for. Perhaps, to a comical, like ‘Batman villain-esque’ degree in some cases, but you get the idea. The other aspect of this and the part that I really try to bring up whenever I talk about the site. Yes, the site is a lot of fun and we poke fun at silly clients, ignorant clients, and sometimes just anger inducing clients, but a lot of the time it is very much a two-way street.

A client from hell emerges from a set of circumstances that the freelancer absolutely has a hand in shaping. There are certain characteristics a client can have, where they’re probably just going to be bad to work with and you know how to watch out for those. Things like ambiguous expectations for what are they expecting to come out of the work you’re doing for them, they’re unappreciative, they’re disrespectful, they devalue good work, things like that.

I could go into way more detail about each of those, but there are things a freelancer can do that contribute to those ambiguous expectations. There are things freelancers do where they don’t do the work they promised to do, or they burn a client and as a result, that client is less trusting of the next freelancer they work with. It creates this really sort of hostile relationship and … It’s my opinion that freelancing, what makes it such a great thing, is you get to do the work you want to do the way you want to do it.

The catch-22 here being, you have to do the work and you have to do it relatively well. If you’re creating an environment, if you or your client are creating an environment that isn’t built on respect and trust and mutual benefits, it’s probably not going to be a terribly positive experience for either of you, and no one, either of you, is particularly at fault. It is a two-way street a lot of the time.

Sonia Simone: Actually, let’s talk with you a little bit more about that. I think that fear of a horrible client does kind of stop some people. It’s always like the people, the good people who get stopped, right? The bad people just go right forward. The people who do have a good work ethic, they’re very talented, and they could actually have a really nice freelance career, but they’re worried about getting burned on money and they’re worried about these terrible clients that we hear so much about. Do you have … I mean, I know what I’ve seen come up again and again. Do you have some, maybe one thing that you see come up again and again where a good freelancer gets taken advantage of because they’re not wise about a particular area of that life?

Bryce Bladon: It’s hard to limit myself to just one-

Sonia Simone: Yeah.

Two Recommendations for Staying Out of Problems with Clients

Bryce Bladon: To be perfectly honest. I’m going to give you two.

Sonia Simone: Yeah, go for it.

Bryce Bladon: Kind of related. One mistake I see a lot of first time freelancers make … I run a course, by the way, called Start Freelancing, we have a few hundred students, so I’ve conducted a bunch of surveys, I’ve reached out to people that ask after this stuff and one of the things I asked was, “Why haven’t you gotten into freelancing up to this point?” A lot of people are scared of those variables, those ambiguities of working with clients that can bite them in the butt. The fear of … I compare freelancing to dating a lot of the time. At least working with clients as a freelancer. That fear of a bad breakup.

Sonia Simone: Yeah.

Bryce Bladon: That fear of entering into a relationship with someone and then finding out they’re someone else. It all boils down to this fear of the unknown, this idea that something could go wrong, so why even start? Again, I’ve been freelancing for ten years and over that time I’ve had, at best, a handful of bad clients. And that is pushing the definition of what a bad client is. I’ve had projects I didn’t love how they turned out, I’ve had clients I’ve chosen not to work with in the end, but I’ve only had one or two bad clients, really, truly awful clients. And it was less them being an awful client and more of them being an awful person.

Which brings me to the second mistake, and the mistake I see a lot of those very nice people making. That is, just a failure to stick up for yourself and to ask the potentially hard questions. This can be as innocuous as not bringing up your rates earlier on in the conversation, and it can be as extreme as a client continually expanding the scope of work and putting unfair expectations on you that were wildly outside of your agreement, and you not wanting to shake the boat, you just wanting to be a pleasant person to work with, you just being too polite and not pushing back and not saying, “Hey, great idea. Unfortunately, it’s not what we agreed upon. It would take me X amount of hours more.”

Sonia Simone: Yeah.

Bryce Bladon: Just having that conversation, and that conversation does not need to be rude. That conversation, bringing it up, does not make you a bad person. In most cases, it makes you a professional, and that’s what professionals do. They talk about this stuff, they bring it up. Yes, you know what? I still get awkward talking about money with my clients. I still feel weird pushing back sometimes, but as long as you’re polite, as long as you’re professional, only the worst kind of people are going to have a negative reaction to that, and if you run into those people, it is just a great litmus test for, “Hey, I don’t want to work with you anymore.”

Sonia Simone: Right, right. Because it’s not going to get better.

Bryce Bladon: No, no it isn’t.

Sonia Simone: It’s not like they’re going to blow up when you set reasonable expectations and then later they’re going to be great. Yeah, and that would be, I’d say, the thing I see over and over, is not setting proper expectations. Everything from not working with an agreement, so you’re not spelling out what’s actually going to be delivered, to just that very point you mentioned where you have to have that conversation and say, “We talked about project A and what you’re asking for now is project Q, so would you like me to work up a proposal for the additional costs, or do you want to put that on … What do you want to do with that?” Yeah, it’s a …

Bryce Bladon: The worst thing I see is when the freelancer lets it go from A, to B, to C, to E, and then all the way down to Q.

Sonia Simone: Yeah.

Bryce Bladon: During that time span, they’re just kind of hoping to themselves that the client realizes their mistake. At the same time, they’re becoming bitter.

Sonia Simone: Right.

Bryce Bladon: They’re becoming annoyed, but they’re not bringing up these issues, and as a result, it’s allowed to fester and the client’s expectations are going in a completely different direction. Whereas, your expectations are going in the complete opposite direction of them. The more you allow that dissonance, the worse that eventual conversation is going to be, so sooner always better than later.

Bryce’s Problem with “Aspirational Freelancing,” and What He Did to Combat it

Sonia Simone: Sure. I know you mentioned, when we were kind of setting this up, a phrase, ‘aspirational freelancing,’ and I thought that was a compelling phrase, and I would love you to explain what it is, and then what can you tell us about it?

Bryce Bladon: Quick admission I need to get out of the way, real quick. That is, that I often work as a communications consultant, which means I often work in the realm of marketing. Which brings me to my next point, which brings me eventually to the point we’re going to try to make here. One of the first things you learn in marketing is what you’re trying to sell to a person is not the product or the thing, it’s the person this product or thing is going to make them into. It’s that brighter tomorrow, it’s that grass is always greener on the other side concept. When I talk about ‘aspirational freelancing,’ I mean if you ever see those little articles that appear on a monthly basis in Forbes, or Fast Company with that very just delicious sounding headline of like, “Work for yourself. Work 15 hours a week from home freelancing. Do it. This guy does it. It’s never been easier.”

It has never been easier to get into freelancing and that is a life you could potentially have, but it really undercuts the journey that the guy had to take to get there. Again, been at it for a decade, I love my career, I love where I’m at with it. It’s still not perfect, it’s still not where I want it to be, and even if I had been a lot more targeted in everything, even if I’d done everything absolutely right, even if I had a much clearer idea of where I wanted to be, I still would have had to put in the time, I still would have had to put in the work. What I’m getting at here is when … An idea that irks me is the idea that freelancing is an easy ticket to happiness. Again, I love freelancing. I think a lot of people would enjoy freelancing if they do it. I also think freelancing isn’t necessarily for everyone.

It requires you to be a structured person, to be self-motivated, to do the work even if there isn’t immediate work in front of you. To handle deadlines, to organize yourself, to even do a little bit of business and marketing, and those unsexy things that a lot of us writers just turn up our nose at, and understandably so. Don’t expect me to get off my high horse as a marketer a lot of the time. I miss my bourgeoisie days. What I’m getting at here is the idea of ‘aspirational freelancing.’ Freelancing is something you can absolutely aspire to and it’s something that can lead to a better life for you. It can absolutely do that, but just don’t confuse the destination, oh God, I can’t believe I’m dipping into this cliché, with the journey.

Sonia Simone: Right.

Bryce Bladon: Freelancing, your career growth, it never really stops, and you’re not going to get to that dream life within your first week, within your first month, maybe not even within your first year. And even if you do, there are going to be aspects of your job you don’t like. It’s still a job sometimes, even if you’re doing the work you love. There is still the business upkeep. There are all these little unsexy things. You still need to put in a little bit of time, of effort, of that oh-so-unsexy sweat. Yeah, that’s where I get a little irked with ‘aspirational freelancing.’

Sonia Simone: Yeah, absolutely. It’s funny how these same tropes come up. The four hour work week, which was a great tested Google AdWords ad, but it’s not really how it works. There’s not a four hour work … If you have a four hour work day maybe, that might work. My favorite part of the four hour work week is when Tim Ferriss kind of outlines what his typical day looks like and realize that his work week is quite a lot longer than four hours long.

Bryce Bladon: Very true, very true.

A Wealth of Resources Available at Clients from Hell

Sonia Simone: Well, cool. You do have a lot of resources on the site. I think a lot of people would’ve launched a site called Clients from Hell and just kind of monetized it with advertising and called it good. But you have a lot of resources for freelancers, or people who want to know more about freelancing. Feel free, if you want to … If there’s some resources you want to let people know about, I would love to share those with people and let them know what you might have available.

Bryce Bladon: Oh, for sure. Yeah, no, the site itself, if you go to, it is … being entertaining, giving you content that you find fun, or charming, or humorous, or even anger inducing if you want to punish yourself like that. We got all that good stuff and that’s what 98% of our audience is there for. I 100% appreciate that I’m never going to try and force this other stuff down your throat.

That said, a lot of the time people end up on our site because they’re having a terrible client experience, they’re having a frustrating time getting started as a freelancer, so as a result I built up all these resources. If you just go to, you’ll see a handy link at the top that says ‘resources.’ Things like, I built a free course, pretty much based off of my frustration with those aspirational freelancing articles, and courses, and books, and products.

It’s called, “Is Freelancing for You?” and it’s free and it just goes over the realities of freelancing, and the things you need to actually do it. It makes you take a hard look at yourself and ask the real questions before you drop a bunch of money and make some serious life choices that may not be for you, sometimes. They may absolutely be for you, but one way or another you’re going to know.

Earlier, when I talked about that mistake, one of the two mistakes freelancers make with clients. This one is trying to address those ambiguities that scare us so much when starting something new. Speaking of starting something new, I also run a couple courses, “Start Freelancing,” which is a complete guide to, I’m sure you can guess it, and “Find Freelance Work.” Just trying to provide resources that hit on a lot of the pains I had when I was getting started as a freelancer. “Is Freelancing for You?” “Start Freelancing.” “Find Freelance Work.”

I also wrote a book called Hell to Pay, which is all about freelancing finances, stuff like how much you should be saving for taxes, to how you should be charging your clients, to how you can calculate your rate. Yeah, I also run a podcast, Clients from Hell. I have great conversations like I’m having with Sonia here. Our host isn’t nearly as charming as she is, but besides that …

Sonia Simone: Cool. Yeah, no, that’s really cool. The Hell to Pay thing, I think is genius because a lot of people do, especially the copywriters and the design professionals, we get into it because maybe we weren’t math majors, but there’s still math. So I love the title.

Bryce Bladon: Mmm-hmm. (affirmative)

Bryce’s Thoughts on the Wisest Way to Get Started with Freelancing

Sonia Simone: I love the idea of it, so I highly recommend. All right. Well, you know I’m going to ask this question, because everybody probably does, right? If there was one piece of advice … So you’ve got somebody listening to this, they’re thinking about taking the plunge, they’re thinking maybe they’ll do a little freelance work on the side, or maybe they’ve got some money saved, but they’re not quite sure. I’d say, let’s go ahead and say, go ahead and pick up the free course, because I think that’s just smart. If there’s like one little piece of advice that you would give somebody thinking about going ahead and jumping in, what would it be? It can be something from the course, it’s okay.

Bryce Bladon: Oh, it almost will be. Almost all of my advice is in the course in some way, shape, or form.

Sonia Simone: There you go.

Bryce Bladon: That’s why it’s in the course in the first place.

Sonia Simone: Yeah.

Bryce Bladon: It’s good stuff. I guess my main piece of advice always circles back to, take your time getting into freelancing. If you have a full-time job, if you have a part-time job, hold onto that, keep trying to save up some money, three to six months of all your living expenses is what I strongly suggest. So many people are in debt right now, and it’s super unfortunate and it will just add to your stress and anxiety if you’re in debt when you make a big life change like starting to freelance.

Sonia Simone: Yeah.

Bryce Bladon: Getting started does not need to be a giant leap forward. It can be as easy as just trying to find those first few clients while you’re working your regular job. Maybe try and negotiate a few extra hours off each week so you can spend that time on work, whatever. What I recommend is you try to start in a very sustainable and very easygoing way. This way you don’t have a lot of the stress, the anxiety, the confusion that comes with starting something brand new completely from scratch.

You get to ease yourself in, you get to pick and choose your clients and the projects you’re going to work on, you get to take the time to focus on those first few projects and learn what it is to work with clients. If you want to take it a step further, and this is I think the best advice I give out, that would be to take the time to try and research who your ideal client is and why they’d want to work with you.

By this I mean, just send freelancers you admire, creatives you admire, professionals you admire, companies or clients that would be potential clients for you. Do a little research on them. Maybe even reach out with a short email and when I say short, I mean like 150 words short. Do not create work for this person, but personalize the email, thank them for their work, and maybe ask one or two questions related to freelancing that would be relevant to you. Like, “What do you look for in a freelancer?” Or, if you’re talking to a freelancer, like, “How did you find your first few clients? What advice would you give?” Little things like that. It gives you the best knowledge you can get, it tells you who you might want to work with, what they actually care about, how to speak to the things they care about.

It also sets you up with a budding network, which is built on sincerity, and mutual benefit, and caring about the other person’s work, as opposed to … Something that scared me as a freelancer when I was first getting started was that marketing aspect, was that networking aspect. I hate the idea of the slimy used car salesman. It’s funny that I consult on marketing now, because I’m just, I’m such a big believer in, if I genuinely think I can provide value to you, I have no problem speaking to somebody like that now. Likewise, if I reach out to you, it’s because I like something you’re doing and if I want to work with you, it’s because I genuinely think you’re doing good work.

If you build up your network with that same principle in mind, the principle of, ”Don’t reach out to a person because they might give you money, reach out to a person because it would be good for both of you.” You’ll just get so many more positive responses. You’ll have potential referrals coming down the pipeline in the long term. I’m basically giving you a lot of advice for planting seeds. It’s super easy to plant these seeds, it doesn’t need to be something you do all at once. You don’t need a forest to grow over night, you just need to be taking the time to plant a couple seeds every now and then.

Sonia Simone: Yeah.

Bryce Bladon: Wow, that was a little corny, wasn’t it?

Sonia Simone: Oh, I love corny. That’s my favorite thing, because people who are corny are not cynical and I like that. All right. Well, this has been so much fun. Thank you so much. The site is a delight and I really think your advice is … Both in my own experience, and then lots and lots of conversations with freelancers on my side of the fence, I think it’s all spot on. I just want to thank you. Thank you so much. The site is Check it out, it’s fun, it’s entertaining, and there’s good stuff there.

Bryce Bladon: Absolutely. You know what Sonia? You’re a delight.

Sonia Simone: Oh.

Bryce Bladon: If you guys like conversations like this, check out the Clients from Hell podcast. That’s probably more up your guys’ alley, but otherwise check out the site and check out all the other stuff. Sonia though, she’s great. Isn’t she great?

Sonia Simone: All right everybody, thanks and take care.

Bryce Bladon: Thank you so much.