How to Build Visual Roadmaps - A Case Study developing the Obsidian-Excalidraw Roadmap

TL;DR

Use a two-axis template (time horizontally; feasibility/difficulty vertically) to separate today’s deliverables from longer-term, less certain work.

Briefing Cornell Notes

Briefing

A structured visual roadmap turns a messy backlog of requests into a clear, communicable plan—using Excalidraw mind maps to organize the Obsidian-Excalidraw roadmap. The core move is a 2-axis template: the horizontal axis represents time, while the vertical axis represents “reality” (what’s feasible now) versus difficulty (what’s less clear or harder to deliver). Early brainstorming starts as a free-flowing cloud of ideas, then gets reorganized into a 3-by-3 matrix where items naturally trend diagonally—from today’s practical work in the bottom-left toward more visionary or dependency-heavy efforts in the top-right. That diagonal outcome becomes a reality check: ambitious items tend to land later once timing and constraints are made explicit.

The roadmap process begins with reviewing the plugin’s issue log, then layering in additional opportunities gathered from GitHub, Discord, YouTube, and Twitter suggestions. As the list nears completion, ideas are grouped and linked based on the type of development required—specifically whether work targets the core Excalidraw product or the Obsidian plugin—along with difficulty and timing. Dependencies are visualized with arrows, so the plan doesn’t just list tasks; it shows what must happen first and what can follow. The result is a shift from scattered ideas to a coherent plan that reflects both feasibility and sequencing.

Three practical benefits drive the approach. First, it improves idea generation: reviewing the issue log while placing items on the map helps surface additional opportunities, and the roadmap becomes something the creator expects to revisit and extend over time. Second, it sharpens clarity: grouping and linking forces each item into a development category and exposes how effort and timing relate, while arrows make dependencies visible. Third, it strengthens communication: visual roadmaps are easier for teams to interpret, especially when dependencies, timing, tasks, and ownership need to be aligned quickly.

The 3-by-3 matrix is also positioned as a reusable thinking tool beyond this specific plugin case. By swapping axes, it can support risk management (probability vs. impact), business strategy (market share vs. market growth), technical product selection (product vision completeness vs. vendor execution ability), or even mapping “whiskies by flavor” using chosen dimensions.

In terms of near-term priorities, the immediate focus is deploying a new image element into the Obsidian plugin with as full an integration as possible with other Obsidian features. From there, the roadmap points to potential work like LaTeX support and Markdown document previews. Longer-standing requests—such as pencil support, Chinese handwritten fonts, and proper Markdown formatting—are placed later because they depend on core Excalidraw product development. Over the long run, the plan aims at a plugin-like ecosystem where people can share Excalidraw automation solutions in an easy-to-install setup. The takeaway is a direct call to integrate visual thinking into everyday workflows: it’s presented as an efficient way to turn ideas into actionable plans, especially when paired with Obsidian and Excalidraw.

Cornell Notes

The roadmap uses Excalidraw mind maps with a structured template to convert a backlog of requests into a time- and difficulty-aware plan. The horizontal axis tracks time, while the vertical axis separates today’s feasible work from harder or less certain items. Ideas are grouped and linked by development type (core Excalidraw vs. Obsidian plugin), difficulty, and timing, with arrows showing dependencies. The creator argues this improves idea generation, increases clarity through grouping and dependency mapping, and makes plans easier to communicate to teams. A 3-by-3 matrix organizes items into a diagonal pattern—practical near-term work in the bottom-left and dependency-heavy or visionary work in the top-right—then guides near-term execution priorities.

How does the roadmap template translate uncertainty and feasibility into a visual structure?

It uses two axes: time runs horizontally, while “reality” versus difficulty runs vertically. The bottom-left represents today’s reality—work being done now. Items that are less clear or seem more difficult are pushed toward the top-right. As the diagram is reorganized into a 3-by-3 matrix, the layout tends to become diagonal, reflecting that more visionary or dependency-heavy ideas naturally land later once constraints are made explicit.

What method turns a list of requests into an actionable plan rather than a pile of ideas?

The process starts with the issue log and adds suggestions from GitHub, Discord, YouTube, and Twitter. Then ideas are grouped and linked based on development type (core Excalidraw product vs. the Obsidian plugin), along with difficulty and timing. Dependencies are drawn with arrows, so sequencing becomes visible—showing what must be completed before other features can realistically proceed.

Why does grouping and linking matter for clarity in this roadmap approach?

Grouping and linking create a stronger grip on each idea by forcing it into a development category and by tying it to realistic effort and timing. The arrows depicting dependencies prevent the roadmap from becoming a flat checklist; instead, they reveal which requests are blocked by core Excalidraw development and which can be handled within the Obsidian plugin.

How does the roadmap improve communication for teams?

Visual plans make dependencies, timing, tasks, and target ownership easier to see at a glance. That shared visibility helps expedite team alignment because people can quickly understand what connects to what, what happens next, and who is responsible for each part of the sequence.

What are the near-term and long-term priorities described, and how do dependencies shape their placement?

Near-term focus is deploying a new image element into the Obsidian plugin with full integration with other Obsidian features. Building on that, the roadmap identifies opportunities like LaTeX support and Markdown document previews. Longer-standing requests—pencil support, Chinese handwritten fonts, and proper Markdown formatting—are placed later because they depend on core Excalidraw product development, pushing them toward the top-right of the matrix.

How can the 3-by-3 matrix be reused for other decision-making problems?

By changing the axes. The transcript gives examples: risk management can use probability vs. impact; business strategy can use market share vs. market growth; technical product selection can use completeness of the product vision vs. vendor execution ability; and even creative mapping like “whiskies by flavor” can be done by choosing relevant dimensions.

Review Questions

What do the horizontal and vertical axes represent in the roadmap template, and how does that affect where ideas land?
How do arrows and grouping by development type change the roadmap from a list into a dependency-aware plan?
Which requests are delayed due to core Excalidraw dependencies, and what near-term step is positioned as the foundation for later work?

Key Points

1
Use a two-axis template (time horizontally; feasibility/difficulty vertically) to separate today’s deliverables from longer-term, less certain work.
2
Start from a real backlog (e.g., an issue log) and continuously incorporate external requests from community channels.
3
Group ideas by development type—core Excalidraw product work versus Obsidian plugin work—to clarify ownership and constraints.
4
Link dependencies explicitly with arrows so sequencing becomes visible instead of implied.
5
Reorganize brainstorming into a 3-by-3 matrix to create a reality-check pattern that typically trends diagonally from near-term to future work.
6
Treat the 3-by-3 matrix as a reusable decision tool by swapping axis definitions for risk, strategy, or selection problems.
7
Prioritize foundational integration work (like an image element) when later features depend on it.

Highlights

A structured mind map template turns a backlog into a time-and-difficulty roadmap, with near-term work clustered in the bottom-left and harder, dependency-heavy items pushed toward the top-right.

Grouping by development type (core Excalidraw vs. Obsidian plugin) plus dependency arrows makes the plan actionable rather than just descriptive.

The immediate priority is deploying a new image element into the Obsidian plugin, enabling follow-on efforts like LaTeX support and Markdown document previews.

Long-requested features such as pencil support, Chinese handwritten fonts, and proper Markdown formatting are delayed because they hinge on core Excalidraw product development.

The 3-by-3 matrix is presented as a general-purpose framework: change the axes to fit risk management, strategy, or product selection.

Topics

Visual Roadmaps
Excalidraw
Obsidian Plugin
3x3 Matrix
Dependency Planning