How to Overcome Your Insecurities and Be Confident as a Freelancer

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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.

There is not a freelancer alive that doesn’t struggle with insecurity.

It doesn’t matter how long you’ve been freelancing or how good you are. Everyone feels like an imposter.

This week I talked with Michael who is having doubts about approaching clients. He’s struggling because he feels like there are a lot of web designers out there who are a lot better than he is. And he’s trying to get over this nagging feeling that a client might be better off hiring someone else.

Does that struggle sound familiar?

To this day, I still fight with that very same feeling.

So, I sat down and encouraged Michael on his journey, AND HOPEFULLY, it encourages you as well.

[00:00:00] Chris: This week, we are talking about the insecurities that we all feel as freelancers and how to overcome them. That's right. We're talking about beaten up our imposter syndrome. Are you ready?

Let's go.

Tell me if this resonates with you. Have you ever felt like there are so many other freelance web designers out there who are. Much better than you and all the potential clients you have are probably better off hiring someone else. Guess what, if you feel that way you are in good company? My friend, because we all feel that way, myself included.

There are times when I look at other people's portfolios and I feel like giving up. And then I learned that the people who built those impressive portfolios happened to be 10 years younger than I am. And it leaves me in a state of depression. Days, but, but here's the thing. There is not a freelancer alive that doesn't struggle with insecurity.

It doesn't matter how long you've been freelancing or how good you are. Everyone feels like an imposter. And this week I talked with a self Mader, a self-made web designer, podcast listener named Michael, who is having doubts about. Clients, he got discouraged a little bit and he feels like there's a lot of other web designers out there who are just so much better than he is.

So he's trying to get over this nagging, feeling that a client might be better off hiring someone else. So I sat down, I encourage Michael on his journey and hopefully it encourages you as well. But before we dive in, I want to encourage you to sign up for this self-made web designer news. You'll get weekly ish emails encouraging you and teaching you how to crush it as a freelance web designer.

And guess what? If you hit reply, I respond to every single email personally, so go to self-made web and sign up for the newsletter today. All right. Are you ready to hear my conversation with Michael about how to overcome your freelancer insecurities and beat imposter syndrome? Let's do it.

[00:02:08] Michael: I spoke to you maybe four to six weeks ago. And I was still in the process of, you know, trying to learn some skills and, and, uh, try and kind of get some projects under my belt, whether it was concept projects or trying to get some friends to, to get, give me work. And so I'm at the stage where like, I've done a couple of projects now.

And I'm getting some fear around putting myself out there, uh, because I, I basically don't think I'm good enough. And when I, when I go into these Facebook groups and see all these experts, it kind of gives me imposter syndrome. Uh, so I was looking for a bit of advice on that. Um, Yeah. And, and also like someone on Upwork, I've kind of created a profile, a bigger to get your advice on next steps to, to find some jobs in there also.

[00:02:58] Chris: Absolutely. Yeah. Well, first to kind of the insecurities that you're facing and the imposter syndrome that you're experiencing, number one, you need to realize that this is 100% normal and it doesn't. Go away, no matter how skilled you are, right? Like there's, there's this concept that like, once I become, you know, this level of skill developer designer or whatever, then I'm just going to be so confident and I'm not going to have any more fear or insecurities about approaching a client, but that's just not true.

Like if you talk to the most seasoned developers or designers, they, they feel the exact same way. That you do, you know? So because honestly there will always be somebody out there who is much further along than you are. And so you have to be sure, number one, that you're kind of realizing that and psychologists call it, you know, our, our common humanity and that.

Is this common struggle that everybody, you know, kind of experiences. And, and when you realize that it kinda makes it a little easier because you're like, oh, okay, cool. I'm not the only one who's feeling like I'm no good at this thing that I'm trying to be doing. So, you know, just, just understanding that and realizing, you know, that you're, you're amongst a lot of other, really great designers and developers who have.

The exact same experience. And so, um, you know, you shouldn't feel bad about that, that, you know, lack of confidence. Does that make sense?
[00:04:36] Michael: Yeah, totally makes sense. I think I was also hard by the fact of what. I posted on the, so I I'm working a web flow and I posted in the, the UK web flow Facebook group with my portfolio website.

Uh, and I mean, it was off the back of like a $20, a Udemy course and someone like spoiled it straight, straight away and called me out on it. And it just, it just kind of almost, yeah, it felt like. That they were knocking me for, for reason that even though, like, I, I knew exactly how to build this portfolio website and the, the projects within it, I completely built.

So I think that just having that kind of confidence knock from, from the community, just giving me a little doubt.

[00:05:15] Chris: yeah. That's, that's tough. It's never fun to like put yourself out there and get negative feedback. So I think number one, you've got to realize that if anybody is pushing down on you. That's that's coming from a place of their own pain and has very little to do with you because truthfully, I started from templates, right.

We all start from templates. We all start from looking at somebody else's work and trying to copy it. Like that is a very normal part of the process of learning. And I liken it to, you know, like I'm teaching my daughter how to play guitar. Right. You know? Play guitar for a few decades. So when I started, I didn't start by composing my own music and I'm not teaching my daughter how to compose her own songs from the get go.

So now I'm saying, okay, here's the itsy bitsy spider, right? We're going to learn the itsy bitsy spider, and you're going to get really good at that. Right. And then we're going to learn, you know, a few other children's songs that other people have written. So. Th that way she can learn the process of how to play.

And then, you know, then I'm going to have her maybe start to come up with her own song ideas, but you never just start like, knowing exactly what to do and how to do it. You always start from the knowledge of somebody else. So, what you're doing is a hundred percent normal and, and you shouldn't feel bad about that, right?

It's just a part of the process. So, you know, the other part of getting over, you know, imposter syndrome or insecurity. Is just going out there and doing it. And I wish it were more simple than that, or I wish I had something more profound to tell you, you, you just kind of have to go, you know what, despite my fear, despite my nerves or anxiety, I'm just going to go for this thing.

You know, you will get knocked down. Unfortunately, you, you will have moments where clients will say this isn't any good and it'll completely deflate you. And, and, and they'll, they'll say things like, you know, this is bad or, or whatever, and, and, and. Discouraged. I still get that to this day where, you know, clients are like, you're not any good.

Okay. And I'm like, well, you know, I am, but maybe you don't feel that way. So, you know, realize that it's coming. And so don't be as surprised about it. You know, like I, I tend to have a few things that I keep on my computer that I literally call the evidence folder where, and it's evidence of. You know, I should keep going.

Right. I, and I've, I've I take good feedback that I've gotten or an encouraging moment. And I put it in that folder and I remind myself when I'm in those moments of like, man, I don't know what I'm doing. I, I don't, I don't have any clue about how to, you know, run a web design business or be a freelancer. I just come back to.

And it kind of encouraged me. So, you know, you can do that for yourself. It's and it's important to also have a few people around you that are going to be your cheerleaders, you know, and this isn't about you, you know, like, like false positive, it's this isn't about like hyping you up when you're not any good.

Like, you know, w when you're new, you're not going to be good. Right? Like, that's, that's the whole point of being new, like you're learning and you're stumbling. Figuring things out and you can't be down on yourself for just not being that great. When you've, when you've only started, you know, that however long ago you started like, like this stuff, it takes time and that's why people pay good money to, to hire somebody.

That's that's good at it. So my encouragement would be. Find a few people that you can put in your corner and create a community out of it and, you know, say, Hey, let's, let's be encouragement for each other and hold each other accountable to keep going. When we feel like we should be quitting, like you'll never realize how.

It is until you have those types of people in your life. Is that helpful?

[00:09:15] Michael: Oh yeah, I I'm. I am trying to, uh, get a meetup in London for people, other webflow developers. So I'm hoping that I can meet up with them in the next like month or two to have that kind of face-to-face relationship and be able to kind of call upon them and get their advice and also technical help as well.

[00:09:32] Chris: Yeah, that's great. And I think, you know, if you want that, You first gotta be willing to go be that for somebody else, you know, because inevitably, even though you feel like you're not far along, there's somebody out there who's not as far along as, as you are. And so you're, you're going out and being an encouragement to somebody else, you know, is going to actually help you become more confident.

In your own skills, you know, like there, there are times with the podcast and with the blog and with the courses that I've created, that I feel the same way. I'm like, what the heck am I doing? I'm trying, I'm trying to teach people how to do this stuff when I don't even really know what I'm doing myself, you know, but, you know, inevitably there's somebody out there who can gain from the wisdom that you've picked up along the way, whether that's from web design or whether that's from life, you know, you, you might have some kind of secret sauce that you learned just from.

You know, stuff that you've gone through and perspectives that you picked up, that you can really help somebody else with. So kind of, you know, find your own footing by helping other people. So, you know, going and being that for somebody else is just a huge part of, of the process.

[00:10:43] Michael: Um, and then in terms of the Upwork side of things, um, I know you, you seem to be, uh, quite an expert on Upwork. What advice do you have in trying to get my first client on there?

[00:10:54] Chris: For sure. Well, you know, there's a lot to say, but. Compress it all into just a few soundbites. I think the first thing that you've got to do is really try to see through the perspective of the person that you're trying to get to hire you.

So your potential client, so looking at it from their perspectives perspective, how, how would they be looking at. Your profile, what type of questions would they have? What type of answers are they trying to find on there? And, you know, from that, like, from that hypothesis of, okay, this is what I think a potential client would be wanting to see.

Then you put that on your profile. And then after that, it's, it's, it's what I call the freelancer scientific method. You know, you've got a hypothesis of like, okay, my clients want to see this. Then you put that on there and you see if that's really the case. And, and, and how you test that is you start getting some bites on your profile.

And if you start getting some bites on the pitches that you're making. And so from there, and after you've tested and you've gotten some results, you say, okay, did my hypothesis work the way that I thought it should? Or is there something I should improve upon from that? You know, what, what can I do? And then you, you make another hypothesis and then you test it again.

And so you're constantly going through this loop of. Making a guess at what's going to work, testing it out and then refining it and then just doing it again and again. So looking at it from the perspective of the client, having that be the way that you're setting up your profile. So a few really simple ways to do that is to make it more about the client.

Then you make it about yourself, you know? So, uh, A lot of freelancers will go on there and they'll say, you know, Hey, I've got this much experience and I can do these things. And I'm proficient in this area. And the client is more so looking to see how, what you can do will help them grow as an individual, as a company, as a business, help them, you know, get more leads, make more money or whatever.

And so you've got to make sure that you're connecting those dots because if you don't. The client's not going to either. And so you've got to put everything from the perspective of here's what I can do and here's that how that can help you. Right. So, so that's your profile. Then when it comes to your pitch, you've really got to dial in who the perfect client is for you.

And that again, seeing through the lens of the client, that would be most willing to hire you. Right. So you've got to make a guess, like, who is it out there? That's really looking for somebody like me. And then what type of keywords are they putting in their job description? What's their pay range? What is, what is their what's their project, you know, description and, and really trying to come at it from the perspective on the projects that you're at.

Pitching to, right. So making sure that you're learning some stuff within the filters that Upwork has, you know, so as far as how you can fine tune things or narrow down who you're actually seeing another thing is being one of the first freelancers to the punch, so to speak. So, so being one of the first people to actually show up on a project, you know, we're, we're talking about within minutes of when a client has actually put the project description up for people to start bidding on.

[00:14:11] Michael: Yeah, I think I saw it. I heard it on your podcast about setting up Upwork alerts to your RSS feeds and you can get things straight away.

[00:14:19] Chris: Yeah, yeah, absolutely. So you can definitely do that and that, and that's what I recommend, you know, there's a great app called, um, leapfrog leads that kind of does all that for you.

And I've got a promo code that I can send to you. To kind of help out with that, if you want to try it. So there's, there's leapfrog leads, but you know, what I would do before there was something like leapfrog leads was I just had the mobile app and you know, every time I had a free moment, I was just refreshing the app, you know?

So if you dial in your filters enough, you shouldn't be getting a ton of new projects that show up on your feed. It should be. One or two new projects a day. Right. Um, and that are like really good for you to bid on. So when those projects come up and you want to just bid on them as quickly as you can, but, but it's also a patience game.

You know, you don't want to bid on stuff that you've got no business bidding on because that's not going to be good for you. It's not going to be good for the client. And it's just going to hurt your feedback. So you want to be patient and, and just make sure that you're connecting with the right products.

At the right time. Does that make sense?

[00:15:28] Michael: that makes sense. I think I'm basically going to be pitching to people who do not have the time, energy or knowledge to create like a simple, kind of beautiful fast website. So that's just, I guess what I want to pitch my services as fast, affordable, reliable, beautiful websites, basically that.

[00:15:45] Chris: Yeah, for sure. And, and so what I would do with that is I would tie that back to the motivation that the client feels so. If it, if these are folks who they need something, that's a nice good-looking website, but they don't have the time to do it themselves. Then you say things like, you know, are, are you tired of struggling thinking like you don't have enough time to focus on building your business because you're working in your business.

Right? So I'm going to help you build your business so that you can do what matters most. And what moves the needle forward for your company by making money? So, you know, taking some of that anxiety away saying, um, you know, I can, I can get this done quickly. So you can re get to see a return on investment, you know, within a matter of days and not months, you know, like those are the types of keywords that you want to kind of lean into and say, if that's if that's the angle that you're going to come at, another thing is.

You've, you've got to learn how to kind of differentiate yourself a little bit more than just fast, reliable, and affordable. Right. Because everybody is saying that, you know, so, so I would, I would say, have another angle to pitch to the client that, uh, not a lot of other freelancers are going to be saying, you know, looking at what it is that you could offer that makes it really unique to you.

You know, and you might have to do a little self-discovery to kind of figure that out. And it doesn't necessarily have to be a hard skill, like Webflow or development or designer or anything. It could just be your personality that you make things easy and fun. You know, like this isn't going to be a pain in the butt to actually go through the process with me, you know?

Like that could be something like, not a lot of freelancers say that they just say, I'm fast, I'm affordable. I'll get it done for you quickly. You, you don't have to worry about it. Right. Well, you could say I'm a relational person and I want you to have fun with me.

[00:17:32] Michael: Uh, so this, this is really helpful. So thank you very much.

[00:17:34] Chris: Hey, come here for a second. Come close. Listen. If you're feeling discouraged right now if you're feeling like quitting because there are so many other people out there who are so much better than you are, or if you feel simply weighed down by the sheer amount of things that you need to learn to be a better web designer or developer.

Or whatever, guess what you are in good company. There are a host of other people out there who feel the exact same way, and the difference between you and the other people that feel that way is that you aren't going to keep going. My friend, you are going to crush her insecurities and beat the heck out of imposter syndrome.

And then you're going to go on to become a successful web designer. One day, you're going to look back. At your old imposter syndrome. And you're going to say Nana, Nana Boopa. Okay. Because you are going to overcome it. I can feel it in my bones and I mean, Hey, I already know you're smart because you're listening to one of the best podcasts out there.

The self-made web designer podcast *wink wink.* Hey, next week, we've got another awesome episode dropping Wednesday. At midnight, Phoenix time MST in case you're wondering, stay up with me and hang out so you can listen to it. The moment it's available because it's going to be a good one. And so then keep working hard and don't forget if you don't quit, you win.

A depressed woman looking through a window to symbolize overcoming insecurities as a freelancer


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.



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