Big Mistakes to Avoid with Your First Major Freelance Web Design Client

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Hi, I'm Chris and I'm super glad you're here. 7 years ago I taught my self-web design and freelancing. Now, I do my best to teach others what I've learned so they don't have to struggle as much as I did.

Every week, I write an article and release a podcast episode. Sign up if you want to get notified when that happens.

Mistakes with freelance clients are kind of unavoidable. But a wise woman named Eleanor Roosevelt once said it’s better to “learn from the mistakes of others. [Because] you can’t live long enough to make them all yourself.”

This week I sat down with my wife, Sarah, to talk about her experience with her first big client.

She made a lot of mistakes and learned a lot from them. And, as I like to say, you shouldn’t ever waste a really good failure.

So, she’s going to share her experience to help you avoid the same pitfalls she experienced.

It was a great conversation and I know you’re going to benefit from it!

You’ll Learn

  • The psychology of working with a freelance client on a creative project
  • How to think like your client so you don’t waste your time in a direction that they won’t like
  • How to learn what you need in order to be successful on freelance projects


[00:00:00] Chris: This week, I talked to my wife about the lessons she learned from her first big web design client. It's going to be a lot of good insight and maybe a little bit of some sappy stuff here. Ready? Let's go.

What's up self-maders and welcome to another episode of the self-made web design. Podcast, the first few clients that you get as a freelancer are always the hardest right there. They're always messy. You're always kind of second-guessing yourself. And those first few projects can kind of leave you feeling like maybe you're not cut out for this kind of work.

And that's exactly how my wife Sarah felt during the middle of her first project with a really big. Really big isn't it. They were paying her some good money, but despite that, she kept pushing through and she came out of the other side with a happy client and a new perspective and some great wisdom that I wanted her to share with you today so that you could be encouraged no matter what stage.

Are in, but before we dive in, I'm going to tell you a bout a free course that is available to you at self-made web called the web designer starter kit course in it. I lay out everything that I used to learn, how to go from knowing nothing about design or development. To doubling my income as a freelancer side, hustling designer, over 2000 people have been through this course, and I want to encourage you.

You can do it too. If there's nothing special about me, there's nothing special about the folks who have gone through this course and gone on to become successful web designers. They just decided to do it. And then they went for it. And this is going to give you the tools that you need to learn everything for that same thing.

So you go to self-made web and sign up today. All right. Are you ready to learn all the big mistakes to avoid with your first major freelance web design clients? All right, let's do it. Well, miss Sarah, miss strick. Welcome back to the self-made web designer podcast. Thank you

[00:02:07] Sarah: for having me, Mr.

[00:02:08] Chris: Mr. Yeah. I mean, this is like the easiest interview to do. Cause you literally sit right, right next to me. And so we just have to face a mic your direction and boom, we've got a podcast typically.

[00:02:20] Sarah: I'm the one hushing everyone in our household while you're here. Having this conversation

[00:02:26] Chris: alone or with somebody virtually, you know, so, but I do talk to myself quite a bit.

So I, I w I brought you on because you just kind of finished up, uh, uh, uh, one of the biggest projects that you've done as a web designer. Um, and so while the experience was kind of fresh in your mind, I figured it would be. Kind of a good conversation for those who are getting their first few projects or maybe even like finishing up their first few projects.

So, but before we dive into deep, why don't you take us back and, and, and give us a little bit of context on what you've done as a freelancer, as a web designer up until this point and where you're at right now? Yeah.

[00:03:08] Sarah: So I initially got involved in web design because I'm married to the self-made web designer.

Um, so. He would get lots of extra projects. And I was like, oh, I guess, I mean, I could learn this and you were encouraging me. Like we could do this together, you know? Um, and so I learned enough to, to help you when like projects started to. Uh, layer on top of one another. Right. And so I'm slowly, but surely friends found out that I was learning web design and they'd come to me for charity and say, can you build my website for cheap or for free?

And typically the answer was yes. And then. But the caveat was I'm going to learn as I go. So I'm going to stumble through this alongside you, and if you're up for that, I'm up for it. And so there was really low stakes with those web designs and really low stakes, partially because the relationships were stronger than the business side of things.

I didn't, I didn't need to worry about whether or not they trusted me. I didn't need to worry about whether or not. Um, if I made a mistake, they'd be angry because we all knew we were on the same playing field. So, uh, that's where I came from. And then one day we had a conversation. We were strolling around the streets of Mesa with our little boy.

And you said to me, do you think you're ready to take on a paid client? And I said, yeah, I think I'm ready. And then a week later you showed up in the kitchen and said, I just got off a client call. Their budget is lower than me. Uh, so I recommended you and they said they want you. And I was like, wait, it's a week later.

I thought I was going to have time to put my little ducks in a row and come up with like a business system and all the things. And none of that was prepared. I was not prepared. But actually I was more prepared than I thought

[00:05:03] Chris: I was. And I think that is real indicative of where a lot of people are, you know, they feel like in order to get started, everything has to be nice and pristine and, and everything's down and they know exactly what they're doing from one step to the next.

But really you just had this inkling of like, I think I can do. And then, and then it was just there on your doorstep. So, but it was, it was a bit of a tougher process of that than that, but talk a little bit about what you felt going into it, and then how that changed at the very

[00:05:36] Sarah: end. I was terrified. My anxiety was at an all time high.

Um, I don't come from a family of business people. We don't run any businesses. We don't. Um, my grandfather ran a business. He died when my mom was 14. So like business may have run in my family at some point, but I've never seen it personally. Basically everyone I know in my family worked for someone else.

And so this idea that like I was the sales person and the project manager and the designer, and I needed to make sure we had contracts and we had a business plan. All of that terrified me because while in theory, it's just step one through five in, um, in my mind it just sounded like a bunch of, um, you know, intense.

There's like intense math equation that I couldn't figure out. It's actually so much more simple than my anxiety made it out to be. But the things, the hurdles that I had to overcome had a whole lot more to do with the business side of things than the design

[00:06:37] Chris: side. And you even at one point you were like, I don't want to do this anymore.

Like I, I'm never taking on my own projects again, like, I'm just going to help you. But how has that changed now? Because I know that you mentioned your client came back and was ecstatic with the result. And so do you have a different perspective on that now? Or is that still like, I still don't want to do this by myself again, it was a nice try, but this is not for me.

[00:07:05] Sarah: I realized. Systems matter so much more to me than I ever knew. Um, I. I'm the girl who organizes her books in rainbow order. Like literally 10 years before the whole medic came out on Netflix. I was rainbow ordering our bookshelves. So I, um, I'm very much into aesthetics and organization, but this idea of aesthetics within a business like this is step one, let's automate this.

This is step two. Let's automate this. I never realized how important that was to me until we had this. This particular client. So I think I would do it again, but I would do it again. Having created the automations first and making our system. Just as important as the money we're making, because we'll be able to make that money so much more efficiently if we create these systems ahead of it.

[00:07:58] Chris: And I, and I think some of that too, is a little bit of confidence. You know? Like you, you not realizing that you actually have a lot more to offer to a client than. Then you think you do, you know, and I think we tend to think, especially as we're getting started, like, why would somebody pay for me for this?

Like they probably know just as much just as much about this stuff as I do, but in your first interactions with a client, you started realizing, wait a second. As much as if I'm at a 10 than they are at like a one.

[00:08:30] Sarah: Yeah, the, the initial client, they asked me if it would be a surcharge to, uh, embed videos onto their site.

I almost laughed and was like, ah, that's just a, that's just a normal part of web design. Like that's just good marketing, you know? Um, and I realized in that moment, okay. She is more concerned about trusting me and be being nickel and dimed than she is about my business savvy. And I need to like go and just.

Uh, make this more about the psychology of the business transaction than the actual system of it. Yeah.

[00:09:10] Chris: So it was much more about the relationship. It was much more about connecting with and, and, and helping a client with their fears, because it sounds like you had this idea of like, okay, Is going to want this, this and this from me, but actually they didn't want any of that.

Right. They wanted something completely different.

[00:09:30] Sarah: I wanted the systems, I wanted the business savvy. I wanted the confidence that comes with having done this once or twice. And I didn't have that yet. So I automatically assumed that my need was my client's need. And that was really my. Steak, because my client's need was me to hold her hand through a process that took way longer than either of us anticipated all because she had too many irons in the fire and didn't know it yet.

[00:09:54] Chris: Yeah. And I, I think it's so good. Like this is such a nugget that I think we should maybe camp on for just a little bit longer. Is you can't, you can't pretend to assume. What a client is looking for from you, right? Like, that's that, that's almost a recipe for disaster. Like you have to go into it eyes wide, open saying curious and curious, right?

Like this client is incredibly different from me. They're probably incredibly different from any other client that I've had before. So how can I really understand? What is motivating this client, what, what's their fears? What's their anxieties. What's, what's the, the, the why behind the why, you know, they need a website, but why, right?

Like you, you know, there's all these layers to people's motivations for hiring you. And one of your first jobs is to uncover those and figure them out so that you can serve them the best. And it might not be like, Something incredibly different from all the other stuff, but it's like, you're highlighting like other things that maybe you didn't highlight with another client.

So like this client you're highlighting, Hey, we're not going to nickel and dime you for this stuff. You know, because that was her fear that she had reached the limit of her budget. And if she asked for one more thing, then she's going to owe us another thousand dollars kind of thing. Right, right.

[00:11:13] Sarah: That was not at all the situation.

And I just needed to put on my people-person hat and go, okay. In this moment, I need to just build trust with this woman. And I need to focus on building trust with this woman. Every time we jump on a call, because I'm realizing that she's probably been burned in business before by contractors, and we need to do everything we can to build the trust because that.

Become very evident that that's most important

[00:11:39] Chris: to her. And it's interesting because our interactions, you know, cause I was, I wasn't a part of them, but I was talking with you through them. Our interactions with her at the beginning were drastically different than they were at the very end.

[00:11:53] Sarah: Absolutely. In fact, we.

We thought her and her brand were completely different at the beginning than what we found her to actually be towards the middle of the project. And when we started to do more research on the product and the clientele that. Aiming for, we realized, oh, we branded this website all wrong and we had to start from scratch again.

And that's when you really jumped in and helped me because I was like, oh my gosh, I misread her entirely. But really what I was, what I was reading initially was her anxiety.

[00:12:30] Chris: Yeah. I think that's good. I think there's a couple things to that. I think number one, Be flexible with your understanding of what the client actually needs and be willing to make pivots when it, when it serves the client better.

You know, we, we came to a fork in the road of like, we've been doing wire frames. We had fonts picked out. We had colors picked out. And then all of a sudden, when we went to sit down and. Um, to actually do the website. We're like this doesn't work,

[00:12:56] Sarah: right. The images that we received from her and the content, it just didn't match where we thought we needed to go.


[00:13:04] Chris: So talk a little bit about some of the struggles that you had. Cause it's not like this was all cake and butterflies. Um, is that a saying, people say cake and butterflies? No, I think we should make it

[00:13:17] Sarah: one day bulldogs and butterflies point. I mean, maybe that's just like my wildly charismatic Christian upbringing.

I don't think

[00:13:26] Chris: that was a song and butterflies. Yeah. They both been born again. Wow. Okay. Well, I'm going to have to look up that song after we're done with this interview. Yeah. Right. Uh, so, uh, it wasn't all cake and butterflies where you like there, there was, there was moments where you wanted to walk away.

So, so talk about that. How did, how did you get through that?

[00:13:49] Sarah: Kind of a perfectionist by personality. I really love helping people. And I really love that my help is of the most excellent caliber. And so when I find out that I can't be at my best at something, I would rather walk away and, you know, refund her money and hand it off to someone I know will do a great job for her.

Take the time and the pain that I need to learn and grow past it because I can be successful in other things. And so I, I was like, this isn't for me, this is for my husband. I thought we could be a husband and wife team. I was wrong. This is hard. I don't want to do this. We've got other things going on.

There's plenty of things I could do. Um, and I don't have to be. Um, I don't have to be the wife web designer. Um, and so I kind of almost fell back on that idea. Like, like we, we didn't, I didn't need this job. I wanted this. Until I realized I didn't, I didn't want it anymore.

[00:14:53] Chris: Yeah. Yeah, for sure. But I think some of that, like, you know, talking about your personality and talking about like, wanting to be super helpful and wanting to be super appreciated, some of that was the client not giving you those signals.

Right. You know? And so you would jump on a phone call with her. And even though none of this was said, you were thinking the client hates this. They hate me, you know? And so we. Going a little bit further. We find out she's loves it, right.

[00:15:24] Sarah: She's just a stoic personality.

[00:15:26] Chris: And so that goes back to not assuming that your client is going to want what you want or respond in the way that you would respond.

If, if you were the person on the other side of the table,

[00:15:39] Sarah: business is more about psychology than it is about money.

[00:15:42] Chris: Yeah. And that's why I, I love talking about mindset because that's, that is what it is. That being successful is all about mindset. Like, yes, there's practicals this there's all this other stuff.

But at the end of the day, that stuff is not going to make you. Cross the finish line on a really tough project like this.

[00:15:59] Sarah: Absolutely. Another thing that really, uh, hit me hard. Um, most of you are side hustlers like us and, um, he got a lot going on and a lot of irons in the fire and I would come. To my laptop at 9:00 PM and go, all right, I'm going to keep working on this website.

And I would have to troubleshoot six things and I get to the seventh thing. And not only am I physically and mentally and emotionally exhausted from my day, but now I've got to learn a seventh thing and I would hit a wall constantly and go, is this worth it? Is this worth it? I'm back in help docs for the show it platform because I have no.

To do next and I'm stuck. And so what I found that was I was able to. Uh, overcome that was, was just the community, the support Googling, uh, having a platform, like show it with support embedded into it so that you don't feel alone in the design process. And then obviously, um, I'm married to you. Yeah. Yeah.

[00:17:07] Chris: Which I think maybe some people out there listening and being like, well, you have the cheat codes, right? Like you've got, you've got the guy who hasn't been doing this for a long time. He's coached other people on how to do it. And so that's kind of an unfair connection. Right. So help

[00:17:25] Sarah: me with this. I'll help you.

Yeah, right.

[00:17:28] Chris: Other stuff. Okay. So, but we, uh, I, I think it's important to, to realize like, yes, you have me, but that doesn't just because you, like, just because you're not married to me doesn't mean you can't have something like me. Right. So what would you say to folks who are like, I feel lost a lot of times and feel like giving up.

And I wish I was had somebody that could just sit down and knock something out with me for five hours. Like, what was your advice to them? My

[00:17:56] Sarah: advice would be what your advice was to me, which is figure out your personality and what you need. So I absolutely need external motivation and external accountability.

I do not have it inside of me. I just don't. I am externally motivated in almost everything that I do. And so knowing that about me, I feel like it is a massive flop, but actually it doesn't have to be. And it's okay that I'm externally motivated and not internally motivated. Um, it just means that now my job is not to stir up some kind of disingenuous.

Internal motivation, but rather gather people around me that know what they're doing, humble myself, and put myself into a design community that can give me the assistance that I need, and then humble myself even further and recognize that I'm going to need double or triple the time that I want a project to take, because, um, I'm, I've got a little.

And the way I learn is going to be slow

[00:18:57] Chris: and grueling. Yeah. And I mean, to be fair, it wasn't that slow and grueling honestly, like just felt

[00:19:03] Sarah: like I was a snail compared to

[00:19:05] Chris: you. Yeah. But I mean, you were comparing my eight years in this to your. Six months in this. Exactly. And I think that can lead to a lot of frustration too, um, where you're like, all these other people are getting these things done and half the time than I am, what's wrong with me, there's nothing wrong with you.

Right. It's just, that's the way this stuff goes, right. It takes you way longer at the very beginning to do something very simple than it would when you're four or five years down the road. So, but I think. The main thing that I think is incredibly important is to there's there's, there's the work of web design freelancing.

And then there's like the meta web designed freelancing, you know, like it's all very, theorial where you're figuring out what do I, what's my personality. Right? Like, how do I learn? What, how do, how do I stay motivated? Um, how do I hold myself accountable to get things done? You know, am I intrinsically motivated or.

Extrinsically motivated and asking those questions at the very beginning and then setting up your environment to where it's just going to kind of move you along the way that serves you best. Um, I, you were watching there's this podcast or that we love called the lazy genius. And it's very girly. So sorry for all you guys who are disappointed in my affinity to watch, you know, very girly podcast things.

But, um, she talks about when you're, you're planning your meals, set it up in such a way that you're deciding once, right? Like you're making one decision on how you're going to do meals, right? So that when you show up to make a meal for your house, you're not going. Okay, what do I need to do? All right.

Well, I need to make a recipe or I need to get the chicken out. Like, no, we've, we've decided all that stuff. Right. And so the same is true for when you're, when you're doing freelancing, when you're getting started with this stuff, like before you get started, make the decision once, like I'm going to have.

A group of people that I'm, I'm going to do office hours with. Right. I'm going to say from nine until 11:00 PM every night, we're all going to hold each other accountable and just get on a zoom call and just literally work while we're all on the zoom call together like that. I've, I've done that before and it's it, I'm so productive.

Like I'm like, why don't I do this more? You know, like figuring out certain things. That you know, are going to help move the needle for you so that you don't get to the place of like, I'm done. I quit. I don't want to do this ever again. Shout

[00:21:39] Sarah: out to Kendra. DACI the lazy genius. Um, one of the other things that she says, um, is to name what matters most.

So, um, in terms of client relationship, one of my biggest flaws in this. Um, this past project was that I attributed what mattered most to me, which was business savvy onto her. When, what mattered most to her was grace and patience because she was in a really busy season of life and she needed an, a large amount of margin between deadlines.

And so, um, actually she was very happy with me, but I wasn't happy with me because I was naming the wrong. I was, I was making something matter that didn't matter at all to my client. And I think that's really important when we're talking about the psychology of someone and staying curious about someone we've got a name, what matters, and then we've got to decide once we, even within the first call, like make a decision one time alongside your, um, your client.

Okay. What matters most to you right now? Uh, is it copy? Is it design? Is it trendy? Aesthetics? Is it timelessness? Is it, um, is it, uh, how long this will take is your deadline really intense? Let's decide once that when all else fails, we fail safe at what matters most to you. And if you can have that conversation ahead of time, it's almost a crucial conversation in order for both of you to be successful and stay on the path because when hurdles come and inevitably they come in every single website that you've ever done, there's a hurdle.

There's some form of. We mentioned, it's like a junk drawer. Um, you've got everything you need in the junk drawer, but organizing it. Typically our clients don't have it organized in a way that makes sense to the web designer. It makes sense to them. So it feels like you're just, you're just handed a junk drawer and told, make a website with this.

Right. There's going to be hurdles in that. And when you, when you decide, okay, I'm going to have these conversations ahead of time. Um, we have a true north and then you can work from that true north when a hurdle

[00:23:48] Chris: arises. Yeah. And I think like the main thing from this that I've, I've kind of learned to encourage people is like, I have never had a project that hasn't been messy, like never.

And I've been doing this for a long time now. Right? I think there's this misunderstanding when you're first getting started, that everything has to be clean and organized and step one, step two, step three.

[00:24:13] Sarah: But that is my life.

[00:24:14] Chris: That is what I want. But yeah, I mean, I would love that too. And I'm working towards that.

It's not like, well, you know, forget it. I'm just never going to be this way. You know, we're trying to put systems in place. We're trying to do that stuff. We're trying to look over our processes. But at the end of the day, getting something done is getting something done. Whether it was, it was a really clean, you know, pristine process or whether it was messy, right.

The stuff.

[00:24:38] Sarah: Yeah. Our physical and our metaphorical junk during this moment is a lot more organized than it's ever been. Well, well done.

[00:24:45] Chris: That's congratulate. I don't even feel like I, I, I knew that.

[00:24:49] Sarah: It was all me, but you kept it that way for the longest I've ever seen.

[00:24:54] Chris: Well, I'm getting better and I was just diagnosed with ADHD.

So now we know you

[00:24:59] Sarah: were just diagnosed with ADHD. That's what you just said, ADHD. Yeah.

[00:25:05] Chris: Yeah. I was just confirming for me that that's that's true. Okay. Thanks. Thanks for that. Well, as we were wrapping up, um, why don't we for, for somebody who is maybe in a place like you were like, just fearful of like, I want to maybe try this, but I'm really afraid because I don't feel like I have all the skillsets that I need.

I'm worried that a client's going to be really frustrated with me. What would your encouragement to them?

[00:25:32] Sarah: I would tell you that you have a whole lot more at your fingertips than you think you do. And, um, In a business situation or a web design situation, your fallback of your natural strengths, um, that I believe are God given.

Um, but your natural strengths are going to come to the forefront and make up for a lot of your failures. And I didn't necessarily. I believe that when I started this project, but now that I've been through a few free ones of your little freebies and then one kind of big client, I realized, man, I am equipped for this work and it's good work.

And I can do this even, even without my business savvy that I think I need, you don't need. You don't always need the things you think you need in these situations. You need to trust yourself, um, rely on the strengths. You already know that you have, and really work those into every conversation you have so that you can build trust with the client.

Because at the end of the day, you really, you're not trying to swindle them out of money or fake up a good website when it's actually a terrible one. No, you want to do quality work and that will shine through more. Absolutely any failure or mistake or misstep, Hey,

[00:26:48] Chris: I hope Sarah's perspective was encouraging to you.

And I think the big takeaways are number one, make sure that you know what you need to stay motivated and CA and accountable while you're going through your first project. You know, we're, we're all different. W what I needed was very different from what Sarah needs. When I was first getting started versus now that she's first getting started, so figure out what you need and put those things into place so that it can kind of just propel you through the process, because you're going to hit moments where you're super frustrated.

And you're wondering if it's a worse than. But if you have those types of systems in place, it's going to be much easier to keep going. And the next thing is, don't worry if things don't go exactly as you hoped they would. Don't, don't worry if things aren't as clean as you thought it would all be freelancing is messy.

Right? I think the analogy. A junk drawer is a good one, right? Most of the time, everything you need is in a junk drawer, right? You just to kind of keep digging around for it and pushing stuff aside until you finally find it. But, but no matter what, just keep going and keep learning. If you do that. You're going to become successful and it's going to be much easier as you go.

Well, Hey, next week, we've got another awesome episode for you. So make sure that you subscribe to the self-made web designer podcast, no matter where you're listening. So you don't miss anything until next time, keep working hard. And don't forget if you don't quit, you.

spilt ice cream on a bench


Hi, I'm Chris and I'm super glad you're here. 7 years ago I taught my self-web design and freelancing. Now, I do my best to teach others what I've learned so they don't have to struggle as much as I did.

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