How Deep Are You Willing to Go Into Your Client's Problem?

I've been talking a lot about lead generation lately, and the thing that I keep coming back to is how obsessed you are with your client's problem. How deep and how far are you willing to go inside of their problem? Because when you're truly willing to do that—to really understand and live in that problem—you become magnetic to the people experiencing it.

For the past decade, I've been obsessed with a very simple but universal problem: How do I do this as myself, without compromise, sustainably? The "this" could be anything—design, development, marketing, brand strategy, whatever your craft is. But the real question underneath is how you do it as yourself, not as what you see in the market, not as what's been done before you, but as you in your fullness and truth.

The "without compromise" part matters because we all have our non-negotiables, the reasons we got into business to begin with. How do you maintain those without reverting back to old habits or old ways of being? How do you do this without compromising who you know you can really become?

And then there's the last piece, which I don't think enough people stick around to really answer fully: How do you do it sustainably? What does that even mean? How do you do this year in, year out, decade in, decade out?

I just recently crossed a decade at SQSPThemes.com, and leading up to it, I felt like I was finished. I felt like I had reached the end of a journey, and quite honestly, I didn't know exactly what direction I was heading in. When you find yourself in that place of not knowing what direction you're going, it can be unsettling, especially if you've had a sense of direction for a long time.

What I figured out for myself, what I realized, is that for a long time I had set myself up to escape. Originally it was to get out of the corporate world, to get out of the box, to get out of the constraints and limits around me. But now, a decade later, there's nothing for me to escape anymore. Instead of running from something, I'm resting inside of what I have, what I've created here.

The sustainable part, for me, is where the love comes in. That's why it's such a vital element to business, especially if you're the creator. When you're in charge, what the love does is bring about a certain devotion, a certain level of commitment that transcends the immediate. You need that transcendent commitment because a lot of business is delayed compensation. The work you put in, the investments you make—they don't have an immediate payoff. They require time.

If there's no love, no devotion, no commitment, then you're not going to be able to make that time. You're more likely to give up or say it didn't work when really it just needed more time.

Underneath all of this—underneath the questions of doing it as yourself without compromise sustainably—the question you're really asking is: Where's the money going to come from? How's it going to flow? How do I keep it flowing? How do I grow that flow?

For years I was obsessed with how money flows—where it comes from, how to keep it moving. But I was never satisfied with the surface-level answers. Most of what gets sold online is what I call half-truth marketing.

It's the dream without the discipline. The highlight reel without the process.

And while those promises might sell, they don't sustain. Because the full truth is that every meaningful result still requires trial, error, and time. I can't in good conscience sell you a shortcut that denies you the part of the process that actually makes you ready for success.

What I've discovered is that business, in the simplest sense, is a system of relationships. The first relationship is the one you have with yourself. As long as that relationship is aligned, coherent, and you have a good amount of trust in yourself, that trust becomes the shadow of money, the shadow of cash flow. As long as there's trust for yourself within yourself, then you'll show up as yourself. And when you do that, it opens up more channels of trust.

If you want to accelerate those channels, be generous. Go back to that love, that devotion, that commitment. Go back to that thing that you are able to do because of it. There are certain things you just can't do because your heart's not in it. But the things that your heart is in, you'll probably find that you can do those things indefinitely. You can do them really well and go the extra mile.

When you give from that place, that delayed compensation—that time gap—closes. It allows strangers, people who've never met you before and might never meet you, to trust you. That currency of trust, which is really about belief, is where belief becomes aligned with action. When you believe yourself and others are able to believe in what you're delivering, then money flows naturally. It's a byproduct.

You don't have to chase it. You don't have to do a whole bunch of stuff. But pay attention to what it is that people are really paying for, and obsess over that. Don't obsess over the money; obsess over the reason people take out their card to pay. Maybe it's relief. Maybe it's to gain a sense of self or identity. Sometimes, in the world of websites and visual creative endeavors, people just want to receive compliments, and they're willing to pay to look good enough for those compliments.

That's what I've been up to for the past decade. And if any of that resonates with you and you'd like to work with me on your Squarespace business, I've created a container where we can meet weekly. You can come if you want, or not—it's up to you. But if you need rhythm, if you need accountability, if you need a space to think and reflect and get clear on what you're about and where you're going, a space to look at your work honestly and get the real value out of it, then the Digital Alchemy Lab is open for you.

I've been refining and ensuring that this is really a transformational space, and for me that starts with perspective. Being able to see the same thing from a different perspective gives you a whole new set of possibilities. With possibility comes opportunity, and with opportunity, you feel like you have some sense of direction, especially when that opportunity is big.

What I've learned and what I know for sure is that there's more to what you do than what you advertise. You've got way more going on inside your business than you've communicated outside of it. That channel of communication between what's happening inside and what's happening on the outside—for me, that's marketing. Opening that channel and allowing there to be a flow of story, of insight, of perspective from within to without sets you up to get more of what you already have.

If you love your work, if you love your clients, if all of that is rosy and peachy but no one knows, then you should probably join me in the lab, and we'll definitely remedy that.

This is an open invitation. The lab doesn't close. There's no launch window, no fake scarcity or urgency—just real scarcity and urgency. Because if that's not enough, then you're probably in the wrong place doing the wrong thing.

Think You Need to Pivot? An Invitation to Think Again

When people think about pivoting, it’s usually to escape.
A bad season.
A dry spell.
A business that’s stopped feeling like them.

The tendency is to think, “I made the leap before—maybe I just need to leap again.”

I know because I’ve been there.

The biggest temptation for me was to exit and cash out completely.

But exploring that option showed me something I might’ve missed otherwise—
the invisible structure beneath everything I’d built.

It had been there the whole time, quietly holding—
even when I wasn’t.

And in that space, I saw the real tension:
between who I was and who I thought I had to be inside it.

Instead of abandoning what I’d built, I started asking:

What if the way forward isn’t a leap—but a return?
What if the guiding question isn’t what’s next, but what’s true?

As I followed that question—and uncovered the value I’d been hiding—
the business stopped feeling like a misrepresentation
and started feeling like a reflection again.

So if you’ve been feeling the need to get out of what you’ve built, ask yourself this:

What if you didn’t need to escape your business to feel at ease?

What if the discomfort wasn’t a signal to run,
but an invitation to go deeper—to solve the kind of problem that expands your capacity
and creates even more value for the people around you?

If you want to explore those answers together,
the Digital Alchemy Lab is now open—for good.

It’s my most accessible offer yet.
The barrier to entry is low.
The return? Priceless.

The Missing Link Between Squarespace and Digital Product Sales

Most people who build their business on Squarespace hit the same wall eventually. They’ve got a beautiful website. A product or idea that people actually want. But when it comes to selling digital downloads—PDFs, templates, videos, memberships—it starts to feel… clunky.

Squarespace makes it easy to sell things you can ship.

But if you’re trying to sell things you can send, that’s where it gets tricky.

You can upload a digital file through Squarespace Commerce, sure.

But what about:

• Sending updates or new versions to existing buyers?

• Limiting downloads or preventing link sharing?

• Adding affiliates or upsells?

• Delivering courses, memberships, or license keys?

That’s where SendOwl comes in.

What’s Missing in Squarespace’s Digital Product System

Squarespace is brilliant for design-driven business owners. It gives you a polished storefront, fast hosting, and zero maintenance headaches.

But when it comes to digital delivery, it’s still got room for growth.

Here’s what that looks like in practice:

Limitation	What it means for you
300 MB file limit (Squarespace Help Center)	You can’t upload large videos, photo packs, or software files.
Only one file per product	You can’t bundle a set of templates or layered design assets unless you zip them together.
No download or license control	Buyers can share your files freely. You can’t limit downloads or track usage.
Link expirations you can’t control	When links expire, you can’t easily resend or extend access.
No affiliate or referral tracking	You can’t reward partners for helping sell your product.

Why SendOwl Fills the Gap

SendOwl was built for exactly this moment: when you’ve outgrown Squarespace’s built-in delivery system but still want to keep your website, your brand, and your freedom.

It’s not another storefront. It’s an invisible layer that handles what Squarespace can’t — securely, automatically, and without friction.

Here’s what it adds back in:

• Bigger files & multiple downloads. Host anywhere and deliver bundles of assets with ease.

• Control & security. Set limits on downloads, expire links, or disable access at any time.

• PDF stamping. Watermark buyer emails on every copy to prevent piracy.

• Affiliate tools. Let collaborators and fans earn commissions when they share your products.

• Subscriptions & memberships. Automate recurring payments, drip releases, and upgrades.

• White-label checkout. Embed the purchase flow directly into your Squarespace site — no ugly redirects.

That’s what makes SendOwl the missing link: it turns your Squarespace website from a portfolio into a digital product business.

Why It Matters

If you’re selling more than a handful of digital products, the cracks in Squarespace’s system eventually show.
You spend more time patching than producing.
You worry about piracy, file limits, or version updates.
And every time someone asks, “Can I get a new link?” — you’re doing manual customer support you never planned for.

SendOwl gives you leverage.
It automates the part of your business that should be automated — delivery, updates, referrals — while letting you focus on what actually drives growth: creating and promoting your work.

🎯 Who This Is For

This integration is ideal for:

• Squarespace designers & developers selling plugins, templates, or code snippets.

• Educators & coaches offering guides, workbooks, or online courses.

• Photographers & artists selling presets, digital prints, or media packs.

• Consultants & studios delivering proprietary frameworks, contracts, or systems.

If your work lives online and your brand lives on Squarespace — SendOwl keeps both connected.

What’s Coming Next

This post kicks off a 4-part series designed to help you master SendOwl from setup to sales.
Here’s what’s next:

1. How to Integrate SendOwl with Squarespace (Step-by-Step Tutorial)

2. How to Secure PDFs, Files, and Videos When Selling Online

3. SendOwl vs Gumroad vs Lemon Squeezy — Which One’s Best for Squarespace Creators?

If you’ve been looking for a clean, reliable way to sell digital products through your Squarespace site—without the headaches—this series is for you.

👉 Next up: I’ll walk you through how to integrate SendOwl with Squarespace, step by step.