EP. 017

How freelancers can overcome Imposter Syndrome and build confidence

Many freelancers struggle to feel confident about their skills and battle recurring Imposter Syndrome–but there is a secret to overcoming those feelings of self-doubt. Kaleigh and Paul discuss how ongoing learning, developing personal taste, and soft skills can all help freelancers become more confident in their daily work.

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Paul:                Alright, in this episode I want to talk about, I guess we both want to talk about if we have the talent to do the job that we are doing as freelancers and talk about impostor syndrome. I feel like the pendulum swings there is no middle ground, I feel like people either think they are super-hot like super talented or they feel like they are not good enough, and they don’t think that there is a middle ground, especially with creative people like us, it’s not really, that middle ground is probably very small and non-existent, where people feel like they are well-rounded, creative people they think that they are the best or the worst. So what do you think about that like do you think that you? Okay I’ll start with this in the beginning did you think that you had the talent to do the job that you were doing?

Kaleigh:           With the type of writing work that I do there are some very technical elements to it and those were things that I had to learn. I feel like I had the core skill of being a good writer and understanding how to communicate well which are things that I could build upon kind of as a foundation and starting point. But there was definitely technical skills and like just kind of practical things that I had to learn and had to be willing to learn to become really good and to be worth hiring by people. So I feel like it is a little bit of okay I was confident in my writing abilities when I started but I still have a long way to go. I still feel that way. I still feel like I have a lot to learn which I want to talk more about later but that is kind of my two cents on it. What about you?

Paul:                I think that I struggle with confidence and impostor syndrome like pretty much everybody else except for narcissists. So yeah, sorry if you are a narcissists, I completely apologize for that comment, but yeah I think in the beginning, if we are talking about in the beginning I definitely felt that I was good enough to get paid but I felt like I had a lot to learn and I still don’t have the answer to this I wonder if you have the answer to this because I guess I consider myself a designer who writes, so I guess I’m more of a designer than a writer maybe.

Well like I don’t know if somebody asks me, what it took to be a good designer? I don’t feel like that I would have the best answer other than like mumbling through something that I think they should hear. What about you like if some, because you said that you are a writer and you are a decent writer, what do you think makes a good writer?

Kaleigh:           I was one of those little kids who always read a lot and always did like the writing contest as a little kid and just was always very into it. I started a long time ago and like really worked hard to be better at it and I always ask for help from teachers and did things outside my normal school work. I just kind of carried that trait on throughout my adult years, and high school years, and college and after that. And I think it that willingness to learn and to keep building upon an existing skill what has helped me do pretty well. Now, do I know everything now? No definitely not and I think the day when I think do know everything is when I’m going to stop getting hired probably but I think it’s partially learned and partially like really hard work and consistently building upon being better and trying hard to learn new things and perfect an existing skill.

Paul:                Remind me again what you are into school for?

Kaleigh:           So I was a communications major in college.

Paul:                And that’s writing? I don’t even know.

Kaleigh:           Yeah it’s like writing, digital media. It’s kind of like hey you don’t know what you are going to do with your life, so why don’t you do this in school. It’s kind of one of those. So yeah I did get a lot of writing practice though, I did an internship in a magazine where I got more writing experience, so like I said it’s just always doing things to try to build upon that existing skill and get better.

Paul:                What do you think build your confidence as a writer the most because I’m sure there are a lot of things but like what’s the most that builds your confidence?

Kaleigh:           That’s such a good question. I think a big validator for me is working with really good editors or writers who I really respect and admire like Joanna Wiebe, of course this is the person who comes to mind. Having her send back a document that’s like this is spot on and very few edits here like this is perfect that for me was like “Ah Yes! I’m doing something right”.

Paul:                So basically, if you show your work to Joanna Wiebe and she says it’s okay.

Kaleigh:           If you are a writer that’s all you have to do.

Paul:                It’s like email Warren Buffet all your questions about investing.

Kaleigh:           What about you?

Paul:                Getting paid builds my confidence for the skills that I have.

Kaleigh:           That’s a good one.

Paul:                It’s funny because that’s probably the biggest thing for me is if somebody going to pay me to do a job then they have the confidence that I’m going to do it so I should probably have the confidence that I’m going to do it as well. I get there is a bit of a tricky slope there where I would never take on a job where I would never get paid to do something I didn’t know that I could do. I think there is a difference between knowing I have the skill to accomplish the job even if I probably need to learn a few things along the way to do it and not having the confidence to do it. Either it’s definitely a defined boundary there where I would not take on a job I didn’t know how to do but I’ll take on a job that I knew that I could do but didn’t have the confidence to necessarily do it.

It’s not I don’t have the confidence to do anything but I’ll do it anyway, so it’s like some weird personality quirk there. And so I want to ask you this next then as far as talking about having to do the work or feeling like an impostor in doing the work. What do you think about talent? Like do you think that is like do you think that you were born a great writer?

Kaleigh:           No.

Paul:                So do you think that there is hope for other people who feel like we were not born great writers?

Kaleigh:           Yeah, for sure like I said I think reading helps a lot. I think really being dedicated to practicing and to trying to find new ways to get better at writing is a good way to approach that. However, I will say that I think that when it comes to a little bit more of the art side of things like design and understanding art, I think that’s a little bit of a natural born talent. I know that you get better when you practice, some people I don’t know what it is, they are just really good artist they just get it. It’s like people who are good at Math, they just get it, you know.

Paul:                I do think that applies to writing though. I heard that you could be too close to it to see that but I definitely think that there is some writers that just even if they are not the most technical, like there is what was that book called, I think the book was called “Blind” where there was no paragraphs in it, and no uppercase letters. It was a weird book where this people got some, I can’t remember I should probably look this up, but I only thought of it now but it was like the most poorly written well written book.

Kaleigh:           Interesting!

Paul:                So when I think about talent I think that you can learn whatever skills like pretty much any skill is learnable. You can learn how to put sentences together. You can learn what an adverb or an adjective or a verb or a noun. You can learn all those words I don’t really have the best grasp on this things but I think where and I don’t know if it’s ingrained or I don’t know if it’s nature versus nurture, right like.

I don’t know if this is ingrained or if it’s exposure, like I don’t know if I am a good designer because I spent my life being exposed to design. I don’t know if I’m an okay writer because I read so many books, so if I look at my kindle it’s getting full, which if you have a kindle that’s a lot of books.

Kaleigh:           That’s a lot of books.

Paul:                So when I kind of think about talent, I kind of think of taste and for me that’s kind of like and I had this conversation with my friends Jared and Justin with our mastermind session the other week. It’s like I would know how to teach a designer how to use Photoshop or Sketch or how to pitch ideas or how to like the reason that the lessons exist in creative class because I know how to teach those things if somebody. And people have asked me like why don’t you teach a course on how to become a better designer.

It’s like I don’t know how to teach people to have good taste. There is probably a way to do it but in my brain like I just can’t comprehend how to teach somebody how to be an engaging writer. Like I know kind of like if you tell stories you make it personal then like. I know a little bit here and there same with the design like I don’t know how to teach people how to have good taste, and I feel that taste is one of the biggest things for talent. If I look at a designer who is struggling to get work and if I look at their portfolio and they could be really good communicators they could be really good in all the other things if they are not good at those things then that’s the probably the reason they are not getting work.

But if they are good at everything but I look at their portfolio and I’m like this is not up to par with the top of industry that they are going after. I don’t know how to help change that right like I don’t know how to read some of like people even email me articles, like this articles are boring but I don’t know why.

Kaleigh:           It’s hard.

Paul:                It’s super subjective like I think I’m a good designer but my taste is super subjective. Outside of subjectivity I also know what the industry at large for design like I know what like the bar is for that just like you probably know what the bar is. You could read something and just tell gutturally like if this is something that would be good enough for copy hackers for example.

Like is this article good enough for copy hackers? You could read it and say yes or no without even getting in technical stuff you could just say this isn’t up to par or this is. What do you think about that? Because I don’t know I don’t have an answer to that which is why I kind of talking about it now.

Kaleigh:           No, I think that makes a lot of sense. I have the same answer like when it comes to writing. Like in my newsletter I teach a lot of the nuts and bolts of writing but I it’s like you said I could never teach somebody to write exactly in the way that I do because it’s my own writing voice and it’s just something that naturally flows out of me and I don’t know exactly how to teach the essence of that.

But I will say that I think that there are other skills that kind of complement that and that’s something we should talk a little bit about too things like really good communication and being able to empathize. I know that that’s something you probably relate with as well, how can people better learn those types of skills as kind of a gateway to the other part?

Paul:                It’s like a none winning battle to try to be the best writer or try to be the best designer. Like I don’t know how you do that. I know that I’m not the best designer or the best writer but I think like you said if you can find skills that compliment or even become more important, then the skills in like it’s so intangible to say, “I am the best designer” or “Anybody is the best designer or the best writer”, right? But like and a lot of times clients don’t care pass a certain point like if you can write an engaging copy or design a site that’s not going to be make them look mickey mouse you are hitting the mark on that course skill and what you brought up I think is super valid because if the other skills that weigh the scale in you favor when somebody is looking to hire you or looking to hire you again or looking to recommend you or for you to somebody else.

I think it’s exactly what you said, communication and empathy and understanding. I would even say for me like I don’t think I’ve ever stood out like I have never won an award for design. My literary agent asked me that, “What awards have you won for designing? We could put that in your bio.” I didn’t won any awards. I didn’t even go to school. I mean that could be a confidence thing for me because I went to school for something totally different and I left university before I even got any kind of degree like I finished high school and that’s it. So for me the continual learning was huge but I think for me like the way that I and I would never really pitch my designs skills I would let my body  work do that what I would pitch because I do think it’s important to convince clients to hire you if they are the right fit for you is like I can be a better communicator than most designers.

Most designers suck at communication which is a good thing because it’s really easy to stand out in that case if the bar is so ridiculously low. Like if you talk to anybody that’s hired designer in the past then they will tell you the gripes that they have with that designer with the bunch of designers, so if you can just be a little bit better than that. I would email my clients once a week every single week about the project like, “This is what I’ve done, this is what is coming up, this is what I need from you.”

The long or short of your communication skills could be that you are 90% than every other freelancer in the world. If you take time to understand their business and why they are hiring you to the job that you are doing, writing, design, whatever; if you understand the business reasons behind that then you can tailor your work to those business reasons. And again, you are setting yourself above like if somebody just hired to write a sales page, to write a sales page or to design a website just to design a website that’s one thing. If you are doing those things to help with a specific point like if you are writing a sales page to increase conversions.

If you start to understand that, if you start to understand the business reasons why they want to hire you to do the creative work you are doing, it’s like above and beyond. Like they are going to love that you have taken time to understand that and you are basing what you are doing on that problem that they have or that pain point that they have.

Kaleigh:           Yeah, and there is actually a ripple effect I think from that where because you understand what they want, you’re nailing the product that you are producing for them, and then you get this amazing results that then kind of reinforces your own confidence and are things that you can leverage as part of your value with future clients; and it just reinforces you if you are struggling with impostor syndrome or you feel like you know I’m getting by, I’m just doing okay I’m never going to be that good though.

Those kind of tiny successes are what help remind you that hey you actually are good at this thing like you are doing good work. Here is a literal proof for you that you are doing a good job. I think that is a nice reminder when you do a good job and the client is happy, it’s a nice reminder that you do know what you are doing and you are actually good at this thing even though sometimes it might feel like you are just cling by the sit of your pants and figuring it out as you go.

Paul:                Yeah and I think it’s easier to sell past results than it is to like I would never tell even If somebody, even if I was in like a pitch meeting with the client, I would never tell somebody like, I’m a great designer, hire me.

Kaleigh:           That sounds ridiculous anyway!

Paul:                Yean it sounds ridiculous but if I could go over like, why did this website and increase sign-ups for the mailing list by 20%, where I redesign this website with the folks on ecommerce and sales went up by 8% in the first month. It’s easier, you are just stating facts and those facts are super compelling.

Kaleigh:           And there are numbers in their too, great!

Paul:                Yes, exactly it seems super scientific, and there is nothing to do with like your ego or lack thereof in your work. It’s just like these are the things that I’ve done in the past. It’s not saying that you can do those things guaranteed in the future like would never tell a client like I will increase your conversions by 8% this month.

Kaleigh:           Yeah, you don’t know.

Paul:                I don’t know. But I think that really helps and that I think would go a long way because I think sometimes if we chase like the talent side of things that is always like a losing… How do know if you are like the best designer and then what does it matter? If you somehow win that award, the best designer of the year award, I don’t even know if this exists, if you win that award it doesn’t really change a lot.

Kaleigh:           It doesn’t.

Paul:                You help a bunch of clients with your skill set and they see results, I think that changes things a lot more, like you said reinforces the talent that you either think or you don’t think you have.

Kaleigh:           That’s right. I think that as long as you are willing to learn and you are open to consistently getting better and practicing and trying to learn more I think that is a big piece of the equation.

Paul:                Yeah, like if I look at and I mean it always because I don’t want to say the hourglass quote, I mean everybody knows it. But like in the beginning I knew that I was not good enough to be a top designer competing for Fortune 500 bids but I knew what the gap was. I know the difference between the work that I was putting out and as well as the practice at that point and the work that was the top of my industry and I think in seeing what is the differences and seeing what hourglass said was the gap, in seeing what the differences between where you are at and where you want to be that becomes a tangible workable thing with practice. Like I didn’t go to school for design, so I would go to websites that I knew are well designed, deconstruct them, make them myself, make them again, make them again until I was like, I can make this look just as good or I can make this look a little bit better subjectively in this ways and then I was improving.

I don’t think I was born with any design skills or talent, whatsoever I think the fact that I practiced design for every single day, for years and years and years, same with writing I think I’m a crappy writer, and I think I was even crappier writer when I started but I feel that in reading every day since I could read and in writing every day for years and years and years I feel like my skills improved and looking for feedback. If I look at my newsletter open rate and one newsletter its way down from all the other ones, so I’m like what was not working about this and I’m kind of like dissected it a little bit and I’ll be able to see and then hopefully make it better just like when I get the last thing I want to say, do you have anything else to say I’m like no I have nothing to say but I have, a couple more things but this one things that turned into two things and the other thing that increases talent is openness to feedback.

Kaleigh:           That’s true.

Paul:                I think that is a huge thing. And somebody asked me the other day because I read about how much I love my editors and they said a lot of writers don’t like working with editors because they are like rip apart their work. That’s my favorite part because that gives me confidence and makes me feel that the work is stronger. Same with clients like if a client is giving the right kind of and we talked about feedback before, but if a client is giving the right kind of feedback base on what they know about their industry or business or their audience then you can take that and learn from it and become better.

And I feel like a lot of strides that I made with that talent that I think that I might have is from getting feedback and being critiqued and that is obviously scary sometimes but I think that that really leads to like breakthroughs and upping the talent game quite a bit.

Kaleigh:           Yeah, there is nothing like a good editor, I can validate that too. I mean yes you might get a ton of suggestions on what you have created as a first draft but then it is kind of interesting to be on the inside equation of well here is how this can be better from somebody who really gets it. It is very interesting to be on the receiving end of that to be able to grow and see here is exactly what I would do differently to make this ten times better.

And like you said you can learn from that so quickly because it is right there on the page in front of you piece by piece and so if you are open to that and you don’t take this as a personal attack or like they are trying to take you down a notch or something like that. If you are open to the suggestions that is one of the fastest ways to improve and to get better at anything.

Paul:                Plus it happens in private.

Kaleigh:           That too yeah.

Paul:                I’m like, I am so glad that this person caught this nonsense because now they are the only person who will have read that and now we can make it better for when the public see. Same as designing websites if there is something that stands out I would rather want one person see it, call me on it and work to fix it because most people only see the finished product and they think that, “Oh this website is so well done”, or “This article is so well written.” It’s like it’s that way because of feedback and critiques.

Kaleigh:           It’s true.

Paul:                Those are now the actual final point that I had to make.

Kaleigh:           Now we are done.

Paul:                Now we are done.

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