I Built My Own Boss

At agencies, I never thought about structure. There were project managers, deadlines, standups, retros. Someone else kept the shape of the work. I just showed up and designed.

Going freelance meant building all of it from scratch. Client acquisition, pipeline management, follow-ups, invoicing, strategy. The design is my trade. Everything around it is what keeps you alive as an independent.

A friend who runs his own studio gave me straightforward advice: focus on contract work short term, build toward project-based clients long term. Simple enough. The issue was execution. I have ADHD, which means my brain runs in parallel rather than in neat sequential task lists. Traditional project management tools assume linear focus: finish one thing, move to the next, check the box. That’s never been how I operate, and forcing it just meant dropping things.

I didn’t need more discipline. I needed a system that matched how I actually think.

The System: Claude Code and Obsidian

I use Obsidian as a filing cabinet and Claude Code as my interface. Markdown files, a terminal, a conversation. That’s the whole stack.

When I open a session I don’t navigate anywhere. I just talk. The system reads my notes, checks what’s active, and surfaces what matters before I ask.

“You have a strategy call on Wednesday. Your pipeline is at 2 leads, target is 10. Someone sent a referral yesterday you haven’t followed up on.”

Then I brain dump whatever’s on my mind. Zero friction, no formatting. It sorts my thoughts, queues actions for the right day, and surfaces context when it’s relevant rather than when I remember to look for it.

Beyond Task Management: Research and Strategic Thinking

The system goes beyond scheduling.

I’ve built a wisdom index from books I’ve read. Extracted quotes surface in my daily journal for spaced recognition, similar to Readwise. The system references that index when making decisions, writing copy, or challenging my thinking.

I use Starcraft metaphors for research depth. When I’m exploring a topic, the system reports confidence on a zergling-to-ultralisk scale, from surface knowledge through to deep conviction. It’s nerdy, but it maps to how I naturally think about when to act versus when to keep digging.

The point is I’ve educated the model to match my thinking patterns rather than squeezing myself into a generic tool. I don’t want a kanban board. I want a system that holds context, connects dots, and tells me when I’m avoiding the uncomfortable work.

A Strategic Sparring Partner

The system plans my days, sets targets, and keeps the pipeline visible. But the part I value most is the strategic dialogue.

I can think out loud, push back on ideas, iterate on positioning the way you would with a colleague or in a workshop. As a freelancer working remotely, I don’t have a whiteboard session on tap. This gives me something close to that. A sparring partner that isn’t a yes man.

And it’s honest with me in ways I’d usually be too close to see. It surfaces blind spots, holds me accountable to the outreach and follow-ups, the work that doesn’t feel like “real work” but keeps the business moving.

The Results

Since building this system, I’ve landed work with agencies I admire, on projects for brands I didn’t expect to touch. I’ve started closing clients on a project basis rather than just day rates. The work got more ambitious and more consistent at the same time.

That’s not because the system is magic. It’s because it handles the operational overhead that used to slow me down. The context-switching, the forgotten follow-ups, the pipeline going cold because something shinier grabbed my attention. I focus on what I’m actually good at. The system handles the rest.

What’s Next: Persistent Memory and the Gap Closing

I want to be honest: the system isn’t perfect. Context resets between sessions. I have to remind it who we are and what we’re doing each time. The relationship doesn’t carry over the way a real one does.

But that gap is closing. Tools like Moltbot are tackling persistent memory. Products like Notion and mymind are approaching the same problem from different angles, building software that doesn’t just store information but understands context over time.

For now, this works. I ship faster, think more clearly, and don’t lose track of what matters. I built my own structure, and it fits how I think.

If you’re interested in how AI changes the way we work and think, I wrote about that too: AI doesn’t make you dumber. You’re just measuring the wrong thing.

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Key Takeaway

• Dean Hope built an AI operating system using Claude Code and Obsidian for freelance design management.
• The system replaces traditional project management with conversational AI that adapts to individual thinking patterns.
• AI-assisted workflow structure helps independent designers focus on craft while maintaining business operations.