Sam Crawford on Premium Pricing Psychology for Designers

In this episode of Looks Good From Here we dive deep with Sam Crawford, the designer behind by Crawford and founder of Six Figure Design Club. Sam shares his unique approach to running two successful businesses simultaneously - high-end Squarespace client work and an intensive mentorship program that's transforming how designers think about their worth. Watch the video or continue reading below.

Building Two Arms of a Creative Business

Sam Crawford has built something unique in the Squarespace community: a thriving client business alongside an educational platform that helps other designers scale their income. With over 200 five-star reviews and a community of designers achieving remarkable results, Sam's approach to business demonstrates that success isn't just about design skills—it's about systems, mindset, and intentional growth.

In a recent conversation on the Looks Good From Here podcast, Sam shared the strategies behind his success, from his meticulous time-blocking system to his philosophy on pricing and the real barriers holding designers back from six-figure incomes.

Extreme Time Management for Maximum Productivity

When asked how he structures his week between client work, his own brand, mentoring, and course creation, Sam revealed an approach that might surprise many designers.

"I'll time block everything and I'll time block for weeks on end everything that needs to happen and when, and I'll annotate within tasks. Okay, like here's what you have to do within this task to get it done. So I'm very, very structured," Sam explained.

His system goes beyond typical calendar management. Sam schedules everything from gym sessions to coffee walks, and even admits to scheduling showers. "I even like schedule in showers. It's ridiculous," he laughed. "Like I have the tab before our interview was like wake up routine. So it's like weigh, hydrate, shower, brush teeth, get ready and then it goes into the task."

The key to making this system work? Planning in advance removes decision fatigue. "For me, if I have everything structured, it just makes everything so easy because I don't have to think. I'll think on a Sunday, let's say, and then plan everything out and then all I do is just execute throughout the week."

From Sports Psychology to Web Design

Sam's journey to becoming a successful Squarespace designer wasn't traditional. After earning a first-class degree in sports psychology, he found himself working in a tourist information office when jobs in his field proved scarce.

"I was working in a tourist information office at the time and people would come into Liverpool and I would tell them about the city and all the things to do," Sam recalled. "And then in my spare time I would start trying to build this site on WordPress."

That WordPress blog about self-improvement—which included an article about a testosterone-boosting stew recipe—became his entry into the online world. After blogging for two years and making around $500 monthly, he explored copywriting, social media management, and various digital services before discovering Squarespace.

The turning point came when he had to make a difficult decision. "I had about £2,000 of recurring income from social media clients, but I hate social media," Sam admitted. "But then I was also making about I'd say £500 to £1,000 on websites. And I was like, do I go all in on this? Ditch this recurring revenue? It was a really uncomfortable moment."

He took the leap, looked at himself in the mirror, and declared: "You're a web designer." That was 2019, and he hasn't stopped since.

Creating Six Figure Design Club

Three years after starting his web design business, Sam had an idea that would become Six Figure Design Club. The inspiration came from a networking group that encouraged him to create a course, but Sam recognized something important about his strengths.

"I was like, guys, I'm not actually anywhere near the best at building Squarespace sites. Like, that's not my strength. My strength is I talk to clients all the time. I get them. It's all about the experience and me being able to deliver a product that okay, it's great, but it's the journey to that product and getting people through the door. That's my strength," Sam explained.

After sitting on the idea for six months, he realized: "Do you know what? I'm pretty good at business. I'm going to teach people what I do and how I do it."

The decision to share his "secret sauce"—his exact processes, templates, software, and client acquisition strategies—wasn't easy. "This is your IP that you're going to basically give out to the whole world," Sam reflected. But he realized the market was large enough to support multiple successful designers.

He launched the course at just £300 to build initial trust and community. Today, it's priced at $2,000 for six months of access, includes over 16 hours of content, and has helped dozens of designers achieve six-figure incomes. Sam switched to dollars as its more widely accepted.

Intensive One-on-One Coaching That Transforms Lives

Beyond the course, Sam offered two cohorts of intensive one-on-one coaching that went far beyond typical business mentorship. For $4,000 over three months, students received two monthly hour-long calls, daily messaging support, a comprehensive 100-page roadmap, and detailed guidance that extended into every aspect of their lives.

"It was it was super intense. Like you'd have my number and I'd be like, okay, you'd wake up at this time. You would, you know, do your pitching three times a day at this time," Sam described.

One student, Nick, spent his entire savings on the program while working a 9-to-5 job. Sam helped him structure his entire day: "I was like, okay, you've got to get up at 6:00, then you've got to go for a coffee. I said, go and sit there, do your pitching, some client fulfillment, go to work, take calls on your lunch break, go home or go to the gym and then take more calls."

The results were remarkable. "They looked at his last year's accounts and it was like £20,000 for the year, and within less than a year he'd made it to £140,000," Sam shared. "And I just looked at him and I said, when did you start earning this much money? And he was like, don't know because it just was just this big blur."

While Sam admits the coaching was incredibly intensive—"the hourly rate that it worked out to was just silly"—he loved the work. However, the program proved unsustainable. "I was so burnt out by the end of it because you're not even doing a course anymore. You're basically being someone's like Yoda."

Breaking Through Self-Limiting Beliefs on Pricing

When asked about the biggest shift designers need to make to reach six figures, Sam's answer was immediate: mindset, specifically around self-limiting beliefs about pricing.

"The biggest thing by far is self-limiting beliefs," Sam stated. "There's this perception that there's a ceiling to a Squarespace site. Even if there was a ceiling, well we know it's at least $36,000 now because we know this exists."

Sam has personally charged $70,000 for a Squarespace website, proving the ceiling is far higher than most designers imagine. "People think the ceiling is like $1,000 or, you know, if they're lucky, $2,000."

His advice for breaking through pricing barriers is both strategic and psychological:

"You need to imagine what your most uncomfortable rate is. Like what would you feel ridiculous saying to a client? And some people would just say £1,000. That just sounds ridiculous. And I say, okay, well go and add 50% onto that and then charge that and see how it goes for the next five leads."

The key insight? "Once you charge a rate and someone accepts it, that is your new rate. If someone is willing to pay that for your service, well that is the new equilibrium."

Sam emphasizes that designers need to recognize their true value: "You're actually doing clients a huge favor. They're not bestowing charity upon you giving you $500 to build this ten-page site. You are transforming their business and you are unlocking things that they can't do and you're bringing immense value to their business."

Six Figures Isn't for Everyone

Despite building a business called Six Figure Design Club, Sam has come to an important realization: the six-figure goal isn't right for everyone, and that's completely acceptable.

"Honestly, I don't think it is for everyone," Sam admitted. "This is something that it's really hard to see other people's perspective when all you know is yours. And I only recently have realized that maybe you don't need to hit $10,000 a month."

He's planning a workshop titled "Maybe You Don't Need $10,000 a Month" to explore this concept. "A lot of it just comes down to a ratio of income versus expenses versus free time. So some people just want low stress and lots of free time and enough to get by. That's fine and it's not that unachievable."

For designers seeking this balance, Sam suggests calculating all expenses, adding $2,000 monthly for savings, and working perhaps 10 hours per week. "I mean, the thing for me is I am just wired to go to the extreme," he explained. "But for for by Crawford I'm trying to push that crazy. I sat back and I was like why am I even doing this? The only answer I could come up with is just because."

His honest assessment of his own journey includes acknowledgment of the costs: "Up until about three months ago I'd just work until I went to sleep. So, you're looking at realistically 12 to about 14 hour work days for five years straight. And that would be weekends as well."

The key is finding your own number and working toward it intentionally. "If you want to take all this leisure time outside of that, that's fine. And I would say don't feel like you need to keep up just for the sake of it."

The Reality of Scaling: Stress and Trade-offs

Sam is transparent about the challenges that come with scaling a business. "You will encounter a lot of stress when trying to scale as well. There's a lot of late nights. I mean, I'm starting to go gray because of the stress, but you know, for me it's worth it. If it's not worth it for you, don't do it. You don't need to."

His circumstances allowed for this level of focus: "I don't have kids. I don't have pets. I don't have a mortgage. I don't have any of those things in life that people love and want to spend time on. I have a very understanding girlfriend and that's it. All I have is work."

For designers with families, mortgages, and other life commitments, the six-figure path might require different strategies or timelines. Sam encourages designers to be honest about their goals: "If you're doing it for a reason and you want to get to that six figures maybe to prove something to yourself or for me a lot of it comes down to I would love to retire my family—if you don't want to do that, that is fine. Just do what whatever you want, whatever makes you happy."

Learning from Design Failures

Even successful designers have embarrassing moments. Early in his career, Sam proudly shared a CSS solution in the Squarespace Facebook community to remove a color overlay, only to have multiple people point out it could be done natively in site styles. "It was just such hubris," Sam laughed. The experience taught him to explore native solutions before jumping to code.

More recently, Sam fired a roofing client who kept rejecting designs without constructive feedback. "Sometimes it's just not worth working with a client," Sam explained. "You will find after one or two rounds of revisions whether this client will ever be happy." The lesson extended to pricing: the client had received a discount, reinforcing Sam's rule to never discount below his $3,500 minimum. "If someone tries to nickel and dime you, they're probably going to be a bit of a hassle."

The Seven-Month Website Redesign

After seven months of intensive work, Sam launched a complete rebrand of his by Crawford website. The new site features custom code throughout, professional branding, and strategic elements designed to boost conversion rates. "Everything is done with intention," Sam explained. "On the last site, my branding was just a Canva logo and I just ran with it for six years."

The redesign focused on serving bigger clients and positioning by Crawford as a high-level agency. One key challenge was the contact page—despite 50,000 monthly visits, Sam was only receiving 30 contact submissions. He added more social proof, direct booking options, and clearer context. "You have to spell it out sometimes for visitors," he noted. The Six Figure Design Club website received similar treatment, with custom Figma designs built extensively in Squarespace.

Finding Your Own Definition of Success

For someone who works as intensively as Sam, rest looks different than traditional breaks. Instead of full days off, he relies on small resets throughout the day—coffee walks with his girlfriend Lucy, gym sessions, or simple social interaction. "I love speaking to people and that recharges me," Sam shared. "If you're wired like me, just take an hour or two to go for a coffee and chat."

Sam Crawford's story demonstrates that building a successful Squarespace design business isn't just about technical skills—it's about systems, mindset, and honest self-assessment about what you want from your business and life. Whether you're aiming for six figures or seeking sustainable balance between income and free time, Sam's journey offers valuable lessons: structure your time intentionally, recognize your true value, price accordingly, and don't be afraid to take unconventional paths.

The most powerful insight? Success doesn't have to look the same for everyone. As Sam plans to explore in his upcoming workshop, maybe you don't need $10,000 a month. Maybe your version of success involves fewer work hours, more family time, and just enough income to live comfortably. Or maybe, like Sam, you're wired to push boundaries and scale aggressively. The key is making that decision consciously, building systems that support your goals, and helping others do the same along the way.

Ready to learn more about scaling your Squarespace design business? Visit Sam Crawford's by Crawford for client work or explore Six Figure Design Club to learn his strategies for building a profitable, sustainable design business.