What’s worth knowing in the Squarespace world.
For designers, developers, and people building businesses around Squarespace.
How I Manage Multiple Content Flywheels Without Burning Out
After nearly a decade of creating Squarespace content, I've learned something crucial: the secret to sustainable content creation isn't about discipline—it's about alignment.
At Circle Day 2024, I shared my framework for managing multiple content streams while actually enjoying the process. Watch the full talk below, or keep reading for the key insights.
The Real Content Challenge
We all know we need content to keep our marketing engines running. But here's what most people miss: you are the engine.
The typical questions are:
What kind of content do I need?
Where should I post it?
But the most important question is: How do I keep creating without burning out?
Two Common Fears That Stop Designers from Creating Content
1. "What if people judge me?"
Here's the truth: They will. And you're judging yourself too.
My approach? Give yourself a year. Close your eyes, create, and review with fresh perspective later. You'll judge from a place of growth, not fear.
2. "How do I maintain quality consistently?"
Honestly? I'm still figuring this out. But I keep going anyway.
The key is understanding that value = change in state. Did you help someone go from:
Confused → Clear?
Frustrated → Relieved?
Stuck → Moving forward?
That's value. And you create those moments every single day.
My Sustainability Secret
Create content that is inherently fulfilling for you, the creator.
When you're tapped into your creative source, you're fulfilled from the inception, not just the reception.
This means:
Passion-driven content keeps you motivated
Your enthusiasm shines through
Your audience joins you for the journey
You have energy for the next piece, and the next
Not every piece gets engagement or generates sales. Most don't. But that first principle—personal fulfillment—gives me enough energy to keep the flywheel spinning.
The 3-Step Framework
1. CAPTURE
Document your high points AND low points (especially the low points). Problems you solve become content gold.
2. DEVELOP
Work with what you captured. Refine it. Ask:
What worked well?
What didn't?
How can I make this better?
3. EXPOSE
Share it when it's ready. Some content takes years. Some you can share tomorrow. Both are valuable.
What This Creates
When you get this right:
🎯 Clients seek you out
🏆 You're recognized as a thought leader
🧲 Your content attracts your people
💰 Multiple income streams develop naturally
🤝 Collaborations happen organically
⏰ Your content works 24/7 while you sleep
The Most Important Part
Give yourself grace.
You won't get it perfect. I'm still trying. But I keep going by recognizing that even though I'm building a machine, I'm human with human needs.
Take care of those first. Think long-term. Focus on what you love.
You'll get where you're trying to go.
Your Next Steps
Which content flywheel will you start (or restart) this week? Reply in the comments and let me know what you're working on.
And if you found this helpful, join the lab where I share more discoveries about building a sustainable Squarespace business.
How a DUI, a Baby, and Squarespace Changed My Life
I was sitting in a holding cell, wondering how I'd gotten here.
Married. About to be a dad. And I'd just gotten a DUI that meant I couldn't drive to my engineering job anymore.
Most people would see this as rock bottom. I saw it as the pressure I needed to finally become who I was meant to be.
Finding out I was becoming a dad in the midst of chaos became my chance to be reborn. If there was a new life coming into the world, I had to create something new too. I had to become the person I wanted my son to see.
That pressure led me to ask myself one question:
What's the one thing I can do right now that I love, that I'm good at, and that people would pay for?
The answer was Squarespace.
But the path from that answer to building SQSP Themes wasn't straightforward. I quit twice. I struggled with pricing. I took on projects I couldn't complete. I tutored on Saturday mornings just to keep the lights on.
I recently sat down with the Squarespace Circle team to share the full story—the chaos, the pivots, the framework that eventually saved me, and what keeps me going today.
This conversation covers everything from that low point to the Digital Alchemy framework I use today: turning problems into content and solutions into products.
If you've ever felt like you're at your own rock bottom, or you're struggling to figure out what your "one thing" is—this one's for you.
The story I was living then became the story I'm telling now in my memoir, "The Corporate Dropout."
The Story Behind the Digital Alchemy Lab
If you’ve ever felt that gap—between what you know is in you and what you’re actually putting out into the world—I want to invite you into this experience.
Seven years ago, I launched my first online course: Behind the Scenes of a 6-Figure Squarespace Business.
It was my first year crossing the $100K milestone, and I wanted to share everything I was learning. On the surface, customers were satisfied. But something about what I was offering didn’t sit right with me.
You often hear about the “skill gap” in creative fields like design, music, or art—that stretch between your taste and your technique. But in coaching and mentoring, that same stretch often goes unspoken.
I started asking myself harder questions:
Could I repeat this “success” reliably?
Could I share the dream I was living—without selling the dream?
And most importantly: How can I hold space for someone else’s transformation while I’m still in the middle of my own?
A few months later, I took the course off the market—and went back to the lab.
The Seven-Year Experiment
Over the next seven years, I stress-tested everything: my philosophy, my purpose, my commitment.
I started new Squarespace businesses.
Built SaaS tools.
Bought and sold digital assets.
Ran workshops.
Gave talks.
Sat on panels.
Launched products.
Shut others down.
Refined the way I worked, taught, and moved through the world.
I needed to see the path clearly—and be honest about what gets in the way, both inside and out.
So I could finally answer the real question:
How do you do this sustainably?
Not just once.
Not just for a launch or a season.
But in a way that continues to create freedom, impact, and income—without burning out, selling out, or losing yourself in the process.
From Theory to Practice
Last summer, I invited a small group of designers and developers into a 1:1 coaching experience.
I wanted to see what would happen if I brought everything—my frameworks, my philosophy, my full attention—into direct relationship with a handful of people doing the work.
No curriculum.
No fluff.
Just presence, perspective, and practice.
Over nine months, we unpacked pricing blocks. We refined offers. We rewired how they thought about time, energy, and ownership.
Most importantly, we turned the raw material of their past projects into systems that could scale.
That’s what the Digital Alchemy Lab is all about.
Learn more about the Digital Alchemy Lab, a monthly mentorship and community for freelancers who want to build systems that compound.