Why Some Evernote Users Struggle to Switch to Obsidian

The Struggle Is Real

One Reddit user titled their post plainly: "I'm *TRYING* to love Obsidian... but the transition from Evernote has been tricky." The emphasis on "trying" speaks volumes. They'd watched tutorials, genuinely wanted to make it work, but were still struggling.

Another user posted about wanting an alternative that supports "rich formatting (NOT markdown)" after migrating to Obsidian. For them, Markdown formatting on mobile was too messy for their main use case—quick editing on their phone.

These aren't isolated cases. For every user who successfully migrates and raves about Obsidian, there's another who finds the transition painful enough to question whether it's worth it. The difference rarely comes down to technical issues. It's about friction in daily use.

Understanding these struggles is important if you're considering the switch. Obsidian isn't right for everyone, and that's okay. The key is knowing which difficulties are temporary and which are fundamental mismatches.

The Markdown Hurdle

The most common barrier is Markdown itself. Evernote uses rich text editing—you select text and click bold, and it becomes bold. Obsidian uses Markdown—you type asterisks around text to make it bold.

Why Markdown Is Hard for Some

For non-technical users, Markdown syntax feels like a step backward:

• You need to memorize syntax: **bold**, *italic*, # heading
• Tables require a specific format that's easy to mess up
• Preview mode vs. edit mode can be confusing
• Some formatting just doesn't translate well from rich text

One user explicitly stated: "I just can't stand Markdown formatting... is there a plugin to make it less painful?" For them, the raw Markdown view was distracting and made quick edits feel like work.

The Mobile Problem

Markdown is particularly challenging on mobile. Typing special characters on a phone keyboard is cumbersome. One user noted that mobile editing was their main use case, and Markdown formatting there was "too messy" to deal with regularly.

If you do most of your note-taking on a phone, Obsidian's Markdown-based approach may never feel comfortable—no matter how good the desktop experience is.

Mobile Experience Issues

Evernote had excellent mobile apps, especially at its peak. You could capture notes quickly, format them easily, and they synced reliably across devices. Obsidian's mobile experience is capable but different in ways that matter for some users.

Sync Configuration

Obsidian doesn't provide free sync out of the box. You either pay for Obsidian Sync or configure your own solution using iCloud, Dropbox, or another service. For non-technical users, setting up sync can be a barrier.

Editing on Small Screens

Markdown editing on a small screen means frequently switching between letters and special characters. Quick notes—those rapid captures that Evernote excelled at—become more deliberate and slower in Obsidian mobile.

Plugin Availability

Many of Obsidian's powerful features come from community plugins, and not all plugins work equally well on mobile. Users who customize extensively on desktop may find their mobile experience limited or inconsistent.

A Different Mental Model

Beyond syntax and interfaces, Obsidian requires a different way of thinking about notes. This mental model shift is subtle but significant.

Files and Folders vs. Notebooks

Evernote uses notebooks and stacks—a container-based model that's familiar to anyone who's used a file system. Obsidian uses... files and folders. But the mental adjustment is real:

• Evernote notes can exist in multiple notebooks (via shortcuts)
• Obsidian notes exist in one folder; linking replaces multi-location
• Evernote's stack hierarchy doesn't directly translate
• Tags work differently in each system

Linking vs. Searching

Obsidian encourages a network of linked notes. Evernote users are accustomed to finding notes through search, notebooks, and tags. The shift to a link-based approach—while powerful—requires rethinking how you organize and retrieve information.

The Empty Canvas Problem

Evernote provides structure out of the box. Obsidian is more of an empty canvas that you shape to your needs. Some users love this flexibility; others feel paralyzed by it and miss Evernote's opinionated approach.

Missing Evernote Features

Obsidian can do many things Evernote can't, but the reverse is also true. Long-time Evernote users may find themselves missing specific features that became part of their workflow.

For users who relied heavily on these features, switching to Obsidian means finding workarounds or accepting that some workflows will be different. This isn't necessarily a dealbreaker, but it is a genuine cost of migration.

When to Consider Other Options

Obsidian is excellent for many users, but it's not universally the right choice. Here are signs you might be better served elsewhere.

Obsidian May Not Be Right If:

• You do most of your note-taking on mobile devices
• You strongly dislike Markdown syntax
• You rely on web clipping as a primary workflow
• You need OCR and image search
• You want something that works out of the box with minimal configuration
• You collaborate frequently with others on notes
• You prefer rich text WYSIWYG editing

Alternatives Worth Considering

Easing the Transition

If you're committed to trying Obsidian but worried about the challenges, there are ways to make the transition easier.

Start Small

Don't try to migrate everything at once. Start with new notes in Obsidian while keeping Evernote for reference. Gradually move content over as you become comfortable with the new workflow.

Use Helpful Plugins

Several plugins can reduce Markdown friction:

• Advanced Tables: Makes table editing much easier
• Settings: Various plugins offer WYSIWYG-style editing
• Hotkeys for specific formats: Reduce need to memorize syntax

Accept the Learning Curve

Give yourself permission to be slow at first. The frustration users feel often comes from expecting immediate productivity. Obsidian rewards patience—you may be slower for weeks before reaching your previous efficiency level.

Keep Both Options

There's no rule that you must choose one and abandon the other. Some users keep Evernote for specific workflows (web clipping, OCR) while using Obsidian for knowledge management and writing. A hybrid approach can work.

Summary and Final Thoughts

Not every Evernote user succeeds in switching to Obsidian. The Markdown learning curve, mobile experience differences, and paradigm shifts in how notes are organized create genuine friction for some users. That's okay—Obsidian isn't universally the right choice.

Key Takeaways

• Markdown syntax is a significant barrier for non-technical users
• Mobile editing is particularly challenging in a Markdown-based system
• The mental model shift from notebooks to linked files takes time
• Some Evernote features (web clipper, OCR) don't have direct equivalents
• Obsidian works best when you adapt to its strengths rather than fighting its differences
• A hybrid approach—using both tools—may work for some users

The Bottom Line

If you're struggling with the Evernote-to-Obsidian transition, you're not alone. The difficulties you're experiencing are common and valid. The question is whether the advantages of Obsidian—local files, extensibility, data ownership—are worth the adjustment period for your specific needs.

Whatever you decide, keep backups of your Evernote data. They preserve your options and ensure you're never locked into a decision that isn't working for you.