BTS: How Two Design Nerds Created the Squarely Speaking Podcast🎙️

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    Okay, so I'm sitting here thinking about how to capture EVERYTHING from our first ‘official’ podcast episode without boring you to tears while you read it instead of listen... but honestly? There's just so much good stuff! 🤷‍♀️

    This is my –Katelyn’s– perspective, by the way (hi! 👋), and along with my podcast co-host Diane, we recently-ish launched Squarely Speaking to further explore our little corner of the internet where we geek out about web design, client management, Squarespace, and other nerdy things that we always find a way to make interesting.

    So grab whatever you're drinking (coffee, wine, –that weird green smoothie– no judgment here), and let's dive into the episode recap!

    Our Origin Stories: How We Got Here 🚀

    Katelyn: My Nonlinear Path to Web Design & Freelancing

    “Well, back in the 90s… –no, I'm just kidding.”

    That's literally how I started telling my story in our episode, which gives you a pretty good idea of my millennial-ness, I guess. 😂

    The real story starts around 2006 when I was fumbling through college with no clear direction, enrolled as an “Interior Design” major in the art department. I had this incredible advisor (which I've since heard is NOT common – lucky me!) who asked what I did for fun. When I mentioned I created and made digital things in my spare time, she immediately said, “Oh, you need to be a graphic designer.”

    That was it! I switched my major and a few months later, I landed my first design job making a whopping $6.00/hr (which was more than minimum wage at the time, so I was actually proud of that!). I've been freelancing on & off since then – which, wow, is a LOT of years. I don't even want to do the math on that…

    So I started in print design – branding, conceptual design, package design, designs for digital things too, but mostly printed stuff. I hit an annoyance-wall pretty quickly when dealing with clients, because of all the color-related headaches: “I got sick of it pretty quick, because you run into a lot of color-related issues. Screen calibrations and… clients are looking at it on their screen. I'm looking at it on mine. It's not the same colors…”

    Being the detail-oriented person I am, I practically fell into web design by accident when my freelance stuff eventually needed a more official home on the web, and I began to build my own website. It quickly began to feel like the perfect fit though. I could dive into the weeds of projects and actually ENJOY being that meticulous. As I told Diane during our chat: “I was like, ooh, I have a reason to be diving in and going into the weeds of this thing... It's all the things that I like, plus none of the things that were bugging me” about print design.

    Linda (one of our live viewers – hi Linda if you're reading this!) asked what helped me when I first started working for myself, and my answer was pretty straightforward: “Google University.” 🤓🧐 Unfortunately, my college-level art education did not include how to run an online business for freelance work… so, I was Googling everything & figuring it out as I went.

    A screenshot of my first & only Etsy order in 2016. LOL

    My Very Failed Etsy Shop Adventure

    In 2015, I took my first real (read: “official”) swing at entrepreneurship by opening a Facebook page and an Etsy shop. Laughably, I only ever sold ONE product. It happened to be purchased on my birthday from a complete stranger, and then I shut the whole operation down because... well, it wasn't exactly thriving. 😬

    During the live, someone asked: What was I selling?

    Oh man, this is embarrassing. 🫣😂 I was working as an in-house designer at a print production company, which gave me access to all their printing materials at a discount & I could design it myself for free, so...

    The one item I sold was a design of a simple David Bowie silhouette graphic (right after he died) –on a foam koozie, which is one of those things you put cans in to keep them cold. I mean COMPLETELY random, right? *shakes head*

    The only mockup of the product I could find in my Etsy account.

    Diane pointed out the obvious problem with my total-noob approach to e-commerce, before I could: “Your brand must have been all over the place then.” 😂 She’s absolutely right, too! There was “nothing unifying the story together.” No wonder it didn't work!

    In 2016, I bought my first unaccredited (not from a college) “business” systems/processes course which probably cost around $297 or something, which felt MASSIVE at the time. I remember feeling, “like clammy hands, shaky.... ––Like, how am I going to make this back?”

    Between courses from educators I found through Google searches, I cobbled together as much free value as possible from blog posts, business books, –anything I could get my hands on, until I could afford the next step up & whatever course that was to learn a very specific thing, one by one & stacking what I learned, implementing EVERYthing.

    The Growing Pains Were REAL

    When Diane asked about my biggest early challenges, there were so many, but the ones I remember most are:

    • Time management nightmare: “I had a full time job and it was like a 20 or 30 minute drive to and from that job. So another hour was wasted in the car. And then doing any work after that was nights and weekends. And I really didn't have a life.”

    • Zero business training: “They never taught me business specifically... They don't teach you how to create a business, how to run a business, how to manage a business, how to be a business owner, which is a totally different thing than being an employee.”

    • The self-design struggle: “It's hardest to design for yourself. It's harder, hardest to market for yourself.”

    And the ISOLATION was kinda crushing: “If you don't have a network where you're, in the weeds with other people trying to do the same thing, it feels very awkward, even lonely... because you don't know who to talk to about it. You have no one to go to advice for and you feel really impostery about the whole thing.”

    Diane immediately related to that isolation: “I didn't know anybody else who was running their own business. No one in my family ran their own business. Like, I was the only human being in the world in the universe who was trying to do this crazy thing. That's certainly how it felt.”

    My Secret "Pivot" Strategy

    When Linda asked in the chat, what I did differently when changing to what I'm doing now (referring to the changes in my service offerings), my answer was simple: “I basically just stopped offering or talking about the things that I didn't want to do anymore. And I took them off my services page. I stopped putting them as a listed item in the inquiry form. I stopped talking about it everywhere.”

    The result? “I have clients now who have no idea that's my background. And I really just cut it out of my life, –like they were toxic.” 😂

    Diane called that the “secret sauce” – just “stop doing the stuff you don't want to do anymore.” And Barb from our audience chimed in too, with “No one needs that toxic negativity, right?!” 😆🙌 EXACTLY.

     

    Diane: From Unfinished Romance Novels to Building A Web Empire 🏙️

    Diane's path couldn't have been more different from mine. She graduated with a degree in sociology and religion/philosophy, which she jokingly called “very practical.” 😅

    She wanted to be a writer –really wanted to do that– joined writers' groups, attended conferences, took classes... but couldn't make it work financially & had trouble finishing the books she started writing.

    Then came THE moment: “One day this girl came in and said, 'Oh, look at my new website. Isn't it amazing?' And she showed it to us. And I was like, 'that is the ugliest thing I have ever seen in my life.' And she was like, 'it only cost me $400.' And I was like, 'Hmm, maybe...'”

    That's when the lightbulb went off: “I could do better than that and make more money than I was making writing unfinished romance novels.”

    So she started building websites – first in Publisher (no shame!), then in Front Page (still no shame!). She got a few writer clients, then writers' organization clients, and people started paying her more and more.

    Her Secret Weapon: Being a Jack of All Trades

    What Diane loves about web design is how it combines so many different skills: “The cool thing to me about web design is that there's so many parts to it. Like you need to have an aesthetic sense and you need to be good at design, but then you also need to be techie and geeky and detail oriented, but you also need to be able to tell a good story. Cause guess what? That's what copy is and marketing is.”

    For the first time, her varied background became an asset: “I'm good at all these things.”

    Her hard work paid off BIG time. She became so successful that: “If you Googled 'Web design for authors,' I was number one or number two. There was this other designer who was... like it was amazing. I was getting clients from all over the world. Like I had clients in like Haiti and Canada and the UK and like everywhere, all over the place, like North Vietnam or Vietnam.”

    When Google Changed Everything

    Then came a major ‘plot twist’ (ha!) – Google changed their search algorithm: “They made, they localized them. So, if you Googled web designer and just web design for small business or whatever, I came up if they were in Denver, Colorado, even if they weren't an author.”

    Suddenly she had inquiries from plumbers, financial advisors, and accountants who weren't writers. She had to expand her services quickly, and that's when her business really exploded “pretty much overnight.”

    She built that WordPress web design business until 2015, sold it, did consulting for a few years, then “burned out pretty hard.” In summer 2022, she rediscovered Squarespace right after they launched Fluid Engine and started her current boutique web design business!

     

    Why We're Both OBSESSED With Squarespace 💙

    A question we see constantly in our industry: “Are you really a web designer if you're using Squarespace?” Our response: Do you want to produce a product that your client doesn't (hate), isn't afraid to death to break, and is not going to get hacked? It's not about the platform, it's about what you're handing off to the person.

    Our clients aren't massive corporations with dedicated IT departments. They need to be able to:

    • Post their own blogs

    • Add events

    • Update pricing

    • Swap forms

    • Change photos

    And Squarespace makes all of that POSSIBLE for them to do on their own.

    If Squarespace stopped being this easy, then I would move over to something else. But having also used ShowIt, Webflow, Shopify, Weebly, and Wix – trust me when I say NOTHING comes close to how quickly you can turn around projects in Squarespace, and your clients don’t hang on for dear life because they aren’t obligated to just to maintain what you did for them.

    Plus, I don't have to waste time on tedious design elements during the build: “I don't have to waste my time drawing a rectangle and putting text on top of it and linking the rectangle and linking the button and giving them both an animation and both a hover animation and then changing that on the mobile view... It's just a button. No.”

    Diane’s WordPress Burnout

    Diane couldn't agree more with my love of Squarespace.

    She spent YEARS feeling guilty about recommending WordPress to clients: “I know how hard this is going to be for you to maintain. I know you're going to struggle to add a hyperlink for crying out loud. And I know it's going to break and I don't know when it's going to break because I don't know when the next WordPress update is coming out.”

    The worst part, she says? “You're going to pay out the nose to have this thing that is going to be a thorn in your side for as long as you have this business.”

    She felt trapped by WordPress: “I was like, this sucks, but it honestly [was] the best solution out there.”

    When she discovered Fluid Engine on Squarespace, –everything changed: “I can almost give a client a site with no tutorials, no nothing, and they can update it now. They can't change out fancy things and maybe they struggle to, they might struggle with something more complex, but like changing text, changing an image, adding a page like you can almost do that with no help right out the gate.”

     

    How The Squarely Speaking Podcast Was Born 🎙️

    Our podcast journey started simply – we were both creating content for the same thing and realized: “Oh my god, this is so much fun. What if we did this more often? –And then it was like, what if we did this more often AND it took something else off our plate? We could just swap this out with something we were already gonna do anyway.”

    What makes our dynamic work is that we're different in many ways but aligned on the crucial stuff: “We do things a lot of things differently, but we care about a lot of the same things. And there's a lot of mutual respect, between us because of that.”

    Diane put it perfectly: “Katelyn's processes blow my mind. –I'm like, I cannot with that. It's like rocket science.” And I feel exactly the same way about hers! 😂 And I love that we have different approaches of tackling the same problem in a lot of cases.

    But we agree on all the important stuff:

    • How to treat clients

    • Content layout

    • The storytelling of sites

    Most importantly, we're both passionate about our work: “We really love our businesses. We really love our content. We really love what we do, and I think that's one of the things we appreciate about each other.”

    Who We're Creating These Episodes For

    While we LOVE beginners and want you here, we're also planning to dive deep into more advanced topics: We both have been doing this almost 20 years. So we'll talk plenty about some more advanced like intermediate topics.”

    We're planning episodes on:

    • Color psychology (we have a whole episode dedicated to this coming up!)

    • Font selection

    • The psychology of intake forms

    • Client relationships

    As Diane put it: “lots of really good, deep stuff here” so expect to get NERDY with us!

     

    WEB DESIGNER Q&A: Our Unfiltered Answers

    For Shopify Development, How Do I Get My First Few Clients?

    Diane’s take, from her current love-hate relationship with Shopify 😂: “Today is not the day to ask me. Today is not the day.”

    But jokes aside, she emphasized that e-commerce sites generally command higher prices than service-based sites, so it's a good skill to develop if e-commerce interests you.

    Her key advice:

    1. Get a website, even just a one-pager

    2. Know what sets you apart (USP) and who your niche is

    3. Build 2-3 sites cheaply for your portfolio

    4. Show examples of what you can deliver

    5. Talk it up to EVERYONE

    My take was simpler: “You can't operate a business in a void, and so the imposter syndrome cannot stop you from talking to people, telling people what you're doing. You have to tell people.”

    And don't just mention it once – repeat yourself …A LOT: “To the point where it probably feels uncomfortable for you.”

    Diane added: “You're not doing it right unless you feel like, ‘oh my god, I'm so pushy.’ Then you're almost there. Almost.”

    The truth is, people aren't paying as much attention as you think & for our audience to see/hear us, we HAVE to repeat ourselves. We can’t just say it once or twice a month, because EVERYONE will forget what we said 3 days ago, 12 days ago, 27 days ago, 5.5 months ago… etc.

    Think about all the REPEATED ads you see on TV, hear on the radio, see at movie theaters, or flashing on those super annoying WordPress Food Blogger websites. Even in promotions for business owners where they resend the same promotional emails for each product launch, –do you remember every word they said when they sent that email series 6 months ago? I seriously doubt it. 😆

    As I said, “Nobody cares about what we're doing except for us.” They’re just trying to get through their days, weeks, and months like we are. “So nobody else is gonna notice that you're saying it seven times.” They're probably “only going to see it once.”

    Would You Do Portfolio Sites For Free/Cheap?

    Diane’s brilliant idea for how to charge for your first few services

    Diane's brilliant pricing psychology: “I would put a reasonable price, maybe a newbie price. A lowish price, nothing super cheap or discounted because people assign a value according to what it costs them to get it. Always. It's human nature. We can't help it.”

    Her strategy:

    List a decent price for your services on your site, but then offer discounts when reaching out personally: “Or half off or 75% off or for $500 bucks or whatever. And so then when they go to your site and they see what you've built and what it's worth, it assigns that value in their head, that perceived value. ‘Oh, wow. Ooh, this is a $2,500 site. I can get it for $800 bucks! Heck yeah.’”

    Katelyn’s thoughts on how to approach offering a few free website builds

    A good reminder for doing ANY work for free is that –no matter the reason– it will devalue whatever you’re offering & the person you’re doing the work for may take advantage (intentionally or otherwise) of your time as a result. So you need to have excellent boundaries in place, and to make it VERY clear what the expected scope of work is, then HOLD that boundary.

    It’s totally okay to do the work for free if that feels doable to you; that’s what I did too, but I did the work for close family members or friends and they did NOT take advantage of me or my time in that process. It was a great learning experience, and they were very respectful of me in the process, but that’s not always the case.

    If you decide to so any work for free, here are some of my tips:

    • make SURE the ‘client’ knows that this is a service you WILL be charging $X for, but this is just the first or second build to learn the steps of the process if they’re willing to be patient with you as you work through the unknowns.

    • Talk to them and decide a very firm scope of work (items to be completed: Home page, About page, Services, Contact, etc), and how long you expect it to take.

    • Run it through the processes & timeline you want to use, and ask that they follow along with you as if this project was costing them your intended rate.

    • Set the expectations, and LEAD them through the project, even if you’re not 100% sure about how to do that. –Remember, they know even less about it than you do!

    Can You Make More Money as a Squarespace Designer vs. as a Shopify Designer?

    This myth is completely backward! E-commerce sites typically command higher prices: “I actually know a designer who charged $80,000 for a Shopify website. She said she'd never do that again, and I can't blame her, but it happens. I don't know any Squarespace designer that charged $80,000.” That $80k project took the designer nearly a year to complete, so for her, it wasn’t worth the money because it was such a big project that she couldn’t take on many other projects & the overall revenue for that year was lower than usual as a result. (Example: $80k x 1 = $80k, but $20k x 5 = $100k, and $30k x 5 = $150k)

    Diane mentioned a Squarespace designer’s infamous $70,000 Squarespace site, but noted that's extremely rare. Most Squarespace sites cap around $20,000, while successful Shopify stores are often in the $20,000 - $30,000 range.

    What's the Right Way to Scale to $5K/Month as a Web Designer?

    Diane's simple but effective strategy: “Every three-ish clients, I would up your price 500 bucks.”

    She started her first site at $2,000 in 2022, then went to $2,500 after two projects, and sold about five at that price while getting comfortable with Squarespace. Then every couple of sites, she'd add another $500. Now her custom sites start at $5,500!

    My honest admission: I didn't change my prices for a long time, “and suddenly two years passed and I was still charging the same rate. So don't do what I did. Do it smarter!” 🤦‍♀️

    Did You Struggle With Being Creative in the Beginning?

    My ‘embarrassing’ truth: “Yes! Even creating the cover photo for my Facebook page, the logo for the profile picture, those kinds of stupid things took me ages. And I'm trained in this!”

    My first website was a disaster: “I was designing like a 60-year-old man. It didn't represent me at all...”

    My problem? Always being an in-house designer meant that what I wanted to design was never part of the equation in my past 9-5s, so I never fully developed my own style.

    Diane's approach was more practical. When she started in 2006, web standards barely existed: “It was just whatever looks good kind of thing. And so I really just tried to make pretty things and I looked at what other people were doing.”

    She created a swipe file of inspiration: “Every time I come across a site that I'm like, ‘Whoa, that's awesome,’ I'll save it.”

    Diane never took formal design classes but focused on sites that were both beautiful AND functional – which is what she loves about design, versus pure art.

    If You Woke Up Tomorrow & Had No Clients, No Money in the Bank, What Would You Do?

    My initial less-helpful answer was: with my current audience, I'd create and sell something quickly to generate cash flow.

    Diane's much more tactical approach, and more helpful to people with no audience yet: Create a special offer and start with every client you've EVER worked with, beginning with the most recent: “A lot of people make this mistake. They're like, ‘well, I just built that site for someone two months ago. They don't need me again.’ –No, no, no! You are fresh in their mind. You blew their minds. You did amazing things for them.”

    After contacting past clients, reach out to professional contacts who know your work ethic, even if they don't that you are a designer yet: “Even if they don't know you as a designer, but they know you in another professional capacity, they know your friendliness with customer service, or they know that your excellence that with which you do things or that you're detail oriented... That is the perfect person to refer clients to you.”

    How Do You “Convince” People to Pay $3K - $5K for a Website?

    My philosophy is simple: “Never ever assume what's in your client's wallet.” That's why I list my prices on my website, –it filters out people who would need convincing.

    Diane's refreshingly direct approach: “I don't. These are the prices. They work for you or they don't. Take it or leave it.”

    The takeaway here is that we don't know clients' finances or priorities. “You don't have to worry about their financial stability!” That’s on THEM to decide; not us.

    Diane learned this lesson the hard way: “When I did consulting and I was like a business coach, I ended up being like a business therapist, which was not fun... I took too much responsibility for my client's success.”

    We both agreed that if you need to convince someone of your service’s value, they're likely going to be a problem client.

    Diane also stressed how your marketing content can position you with clients BEFORE they contact you: “When somebody hears that and it resonates and they get on the phone with you, they immediately treat you differently.”

    Can I Find Enough Clients if I ONLY Use Squarespace to Build Websites?

    Our shared answer: HELL YES!

    The proof is in clients' reactions when they see how easy Squarespace is to use. When working on Sam’s boudoir website in 2024, during our launch day call where I was showing her how to use Squarespace & update the site, I was also showing her how to up date the header navigation links so I said, “You literally just click on the page and drag it up into the Main Nav area, and let go.” –She was gobsmacked at how easy that was compared to her WordPress site. 😍

    When their minds are blown, and they feel empowered to manage their own content (their own home on the interwebs), especially coming from WordPress, the clients who care about that kind of thing flock to Squarespace & designers who specialize in it. 🤷‍♀️😁

    Do Clients Balk if We Don't Code it From Scratch?

    No, not at all! As I emphatically stated: “Clients do not want a website that is coded from scratch. Not the public figures, single person entrepreneurs, small entrepreneur teams – none of them want a website you've custom coded from scratch.”

    They may not know why they don't want it, but we certainly do! All they know is that those kinds of websites require a staff to manage them, and most small businesses or solopreneurs cannot manage that themselves. So our audience of smaller businesses does not want something they can’t understand or manage themselves, because they’re not large enough to have the budget for ongoing IT, help, design services, or to have an internal department of people with those skillsets to maintain a custom-coded site.

    In fact, most are afraid of editing ANYTHING that looks like code! Even in Squarespace’s code areas, –and that’s totally understandable!

    How Much Can You Charge as a Self-Taught, New Web Designer?

    Diane's honest take: “The market will tell you.”

    My practical advice: “You don't really know what people will pay until you ask for it. So until you list it, until you publish it, until you put it out there, –no one's paying attention.” Put your prices out there, and if they don't work, adjust: “If you put it out there at two and you don't get any clients, then change it again or check your messaging on the sales page. A lack of clients could be a result of all kinds of things including marketing efforts, mismatched or ineffective copy & messaging, unrealistic prices, no website traffic, etc.

    However, I can tell you that I charged about $1,200 USD per website at first, being based in the US and working only with US-based clients in the beginning. To me, that felt SO expensive & made me a little uncomfortable, but I was confident that what they’d get for that rate was good for my skillset in 2016-ish. My hourly rate was about $25- $30/hr then, so for a 40-ish hour project, that was about right, for me.

    Your rate may be different because your needs are different! Plus, it’s been 10 years since I built my first client website & there’s inflation to consider, etc.

    So, if you’re hoping to get a “real” or flat number here, I can’t really give YOU that because it should be based on what country you’re in & what your niche is, what bills it has to cover (including taxes & paying yourself!), as well as what feels comfortable or uncomfortable to you!

    What I CAN tell you is that if you decide to charge, say, $500 for your first website –it’s highly unlikely you’ll ever do that again. 😉😂

     

    Coming Soon on The Squarely Speaking Podcast

    We've got some amazing episodes planned, including:

    • A dedicated episode on color (which we've already started planning!)

    • Deep dives into font choice

    • Client management strategies

    • Pricing frameworks

    • how to use AI to create content for ‘fake’ portfolio sites

    • And so much more!

    Whether you're just starting out or you've been designing for years, we're creating content that will help you level up your skills, grow your business, and find your unique place in the web design world.

    So that's the completely unfiltered story of how Squarely Speaking came to be, and how Diane & I both started our businesses!

    If you have questions you'd like us to tackle in future episodes, drop them in the comments or join us on our next live! We can't wait to build this community with you! 💛

     

    Episode Transcript

     
     
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    Katelyn Dekle

    This article was written by me, Katelyn Dekle, the owner & designer behind Launch the Damn Thing®!

    I love coffee & chai, curse like a sailor, make meticulous plans, am very detail-oriented, and love designing websites on Squarespace. As a Web Designer & Educator with nearly 20 years of professional design experience, I’m still passionate about helping & teaching others how to finally 'launch the damn thing' –and have fun in the process!

    https://launchthedamnthing.com
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