No Gatekeeping Series: with Kelly from Makeover Your Website
Okay this one? This is for my chronic pivoters. My “I’ve tried 6 different business ideas and somehow I’m still confused” people. My “I know I’m meant for more but WHAT IS IT???” crowd.
Because Kelly’s story is not a clean, linear, Pinterest-worthy entrepreneur journey. It’s messy. It’s honest. It’s burnout, imposter syndrome, starting over, stopping, starting again…and then finally admitting what you’ve known the whole time.
Let’s set the scene: Kelly is the founder of Makeover Your Website, a “not boring” Squarespace web designer and copywriter for heart-led coaches and service providers. And when she says “not boring,” she means:
Strategic
Conversion-focused
Actually built to make you money
Not just ✨aesthetic✨ for the sake of it.
But before this? She was a full-time high school English and Media Studies teacher. And not in a “I loved it but wanted more” way. In a: “This has never really felt right for me” kind of way. Burnout isn’t a phase, it’s a pattern (if you ignore it). Kelly didn’t just burn out once. She burned out multiple times. And if you’ve ever been in a career that looks good on paper but slowly drains the life out of you… you already know what that feels like.
Teaching gave her: structure, stability, a clear path. But it also gave her: emotional exhaustion. A constant feeling of being “on”. Zero real fulfilment. And the worst part? She could see it wasn’t right… but didn’t know what was.
Like many of us, Kelly found the online business world through personal development. Courses. Coaches. People build lives on their own terms. And something clicked. Not in a “I know exactly what I’m doing” way. More like: “That looks cool… I’m gonna try that.”
So in 2016, she started a coaching business. No experience. No roadmap. Just vibes and determination. And this is where things get important. The accidental skill that changed everything. She couldn’t afford a web designer. So she became one. Her first site? Built on WordPress. Her review of that experience? “I absolutely hated it.” Clunky. Expensive. Constant plugins. A full-time job just to keep it functioning. But instead of quitting, she did what a lot of scrappy business owners do: She learned. Branding, Copywriting, and Squarespace Website design. She went through an intensive bootcamp, built a full brand + site in 10 days (insane), and for the first time…It worked. She started getting clients.
During that process, she had the thought: “Maybe I should be a web designer.” Other people saw it too. Told her she was good at it. And then? She shut it down. Because imposter syndrome said: “Who do you think you are to do this for other people?” So instead of following that very obvious breadcrumb… She spent the next 5–6 years: Starting different businesses, losing interest, getting frustrated, repeating the cycle. BUT every single time she started something new… She built a new website. And loved that part. Like… how much clearer could it get?!
Beginning of 2023. Driving to another day of teaching. And she hits her limit. Out loud, to herself: “Come on, Kelly… what do you actually want to do?” And this time, she didn’t overthink it. She just answered:“I want to build websites for other people.” No overcomplicating. No spiralling. No “but what if…” Just the truth. And honestly, that’s the hardest part for most people.
Within a week Kelly enrolled in a Squarespace course, learned the platform properly, and started building a portfolio. She didn’t wait for “real clients.” She created mock projects. Because you don’t need permission to get started. And by 2024? She landed her first client. But it wasn’t a straight shot from there. After those first few projects in 2023, Kelly actually paused the business. Priorities shifted, burnout crept back in, and instead of forcing it… she stepped away. That part matters.
Because in 2025, she came back, but not as the same version of her business. She rebranded, restarted, and got way more intentional about what she actually wanted to offer. Not just website Design. But the part most people completely overlook:
the messaging
the copy
the content that actually converts
Because a pretty website without strategy? Useless. That shift is what turned her work into something deeper, not just building websites, but helping businesses communicate in a way that actually brings in clients. So what does the work day look like now as a web design business owner? Kelly’s dream: “I’m gonna work from home in my pajamas and have total freedom.”
Reality:
If she stays in pajamas → she gets nothing done
If she doesn’t structure her day → chaos
If she doesn’t stop → she’ll work 8+ hours straight without realizing
Her actual routine looks like:
Slow mornings (non-negotiable as most of our business owners have said!)
Coffee + podcasts (business content, obviously)
Getting dressed (yes, it matters)
Deep work in 2-hour blocks
Lunch at home (upgrade from sad mall food days)
Afternoons with her horse or attempting gym life
And… let’s be honest… sometimes working again at night. It’s not perfect. It’s not aesthetic 24/7. But it’s hers.
The part people REALLY don’t talk about in business? The loneliness. Even as an introvert, she said something that a lot of people don’t expect: “I really miss colleagues.” Because when you leave a traditional job, you don’t just leave the work. You leave: Built-in social interaction, daily conversations, that random office banter. And suddenly it’s just… you. In your house. On your laptop. All day. So yeah, if you’ve ever felt weirdly isolated while building your business…You’re not dramatic. It’s real.
So where is the business at now? At the end of 2025 Kelly was booked out. Fully. She came into 2026 thinking: “This is it. We’ve got momentum.” But then: Client work piled up, Still juggling teaching, No time for her own marketing. And slowly…Momentum faded. She didn’t make a single sale in Q1. And this is where most people panic. Cue: Self-doubt, Questioning everything, Imposter syndrome creeping back in. But here’s the grounded truth:
Q1 is slow for almost everyone
Being busy doesn’t mean your business is growing
If you stop marketing, things will slow down
And most importantly: One bad quarter does not mean you’re failing. (Also she literally made a sale the next night, so… there’s that.)
Kelly’s advice that people NEED to hear:
1. Brand strategy is the foundation. Not optional. Not “I’ll figure it out later.” If your brand is unclear: Your messaging is unclear, Your website won’t convert, People won’t get it. And in a noisy online space? That’s a death sentence. (I learned this one while working with Kelly)
2. You’re probably underestimating how long this takes. People expect: “I launched, where are the clients???” Reality: Conversion rates are ~2–3%, Most people won’t buy right away, You need visibility AND consistency. So no it’s not broken. You just don’t have enough data yet.
3. Stop making emotional decisions. Kelly talked about doing a quarterly review (yes, my workbook made an appearance). Before reviewing? “That quarter was a disaster.” After actually looking at the data? “Wait… no, a lot of this was actually good.” This is your reminder: Your feelings are not always facts.
4. You might be quitting too soon. This one stings a little. But she said it herself: “I think I quit too soon on some things.” Not everything is meant to be forced. But also… not everything is supposed to be easy right away. There’s a difference.
Kelly’s “holy sh*t this is my job” moment? Working on a client project (hi, it was me). She was in a flow state, trusted to do her thing, fully in her element. And it hit: “I’m getting paid to do this.” After YEARS of trying to figure it out. That’s the moment. What is she most proud of? Not revenue. Not clients. Not hitting some arbitrary milestone. Just this: “I’m doing it.” Because she made the hard call to not renew her teaching contract, step into uncertainty, balance relief teaching + business, take the risk anyway. And right now? She’s in the messy middle. Not fully “made it.” Not at the beginning. Just…Building.
Kelly’s story is the perfect example: You’re not lost, you’re avoiding the obvious. The thing you keep coming back to? The part you actually enjoy? The skill that feels natural? Yeah. That one. And also: You’re allowed to pause and restart, You’re allowed to pivot, You’re allowed to take YEARS to figure it out. But at some point…You have to be honest with yourself. If you’re in your trial-and-error era right now: keep going. Just maybe… pay attention to what you keep coming back to. Because it’s probably not random. And as always: no gatekeeping!
Need to see what Kelly is all about? Follow her projects here:
Website
Instagram