Week 1: Holy shit, it's actually fast
Coming from Jira (rest in piss), Linear feels like switching from a Windows 95 machine to something built in this century. Pages actually load instead of making you contemplate your life choices waiting for Jira's spinning wheel of death. Jira took forever to load anything - I'm not timing my fucking page loads, but Linear is way faster.
The speed difference is real. When you're triaging bugs on a Monday morning, not having to wait for every single page to crawl to life means you actually get shit done instead of rage-quitting by noon.
Month 1-2: The Honeymoon Period
Everything feels clean and logical. The keyboard shortcuts actually make sense (Cmd+K to search, C to create issue, G then B to go to backlog). The search finds what you're looking for instead of returning hundreds of irrelevant old tickets.
I think we got faster at handling tickets, but honestly it's hard to tell if that's because Linear is better or because we were just so fucking relieved not to be using Jira anymore. Probably both.
What Works Really Well:
- Search that doesn't suck (unlike Jira's broken search)
- Keyboard shortcuts that feel natural if you use VS Code
- Clean interface that doesn't make your eyes bleed
- GitHub integration that actually syncs properly
- Automatic sprint planning that doesn't require a PhD to configure
- Real-time collaboration that works across time zones
- API documentation that's actually usable
- Slack notifications (when they work)
- Mobile web app that's better than most native apps
- Import tools for migrating from other systems
Month 3-4: Reality Hits
This is where you discover Linear's opinions, and some of them are... opinionated.
The PM Rebellion
Our project manager lost her shit after trying to find Gantt charts that don't exist. She spent half a day looking for timeline views and colorful burn-down reports. When she asked "How do I create a custom field for story points?" I had to explain that Linear basically thinks story points are bullshit and won't let you do it.
She wasn't wrong to be frustrated. Linear assumes you work like a modern software team (two-week sprints, minimal process, engineering-driven priorities). If your PM needs to show stakeholders a timeline with dependencies and milestones, Linear will make them cry.
Enterprise Security Theater
Month 4 is when IT security started asking questions. Linear's security controls are... minimal. There's no SAML groups integration for complex permissions. No advanced audit logging. No compliance certifications that matter to enterprise buyers.
For a startup? Perfect. For a company that needs SOC2 compliance and role-based access control? You're going to have some uncomfortable conversations with your InfoSec team.
The Stuff That Actually Breaks
Let me tell you about the real problems nobody mentions:
Slack Integration Randomly Dies
The Slack integration breaks every few weeks for no reason. No error message, no notification, tickets just stop appearing in channels. I only notice when someone asks "Hey, why didn't I get notified about that critical bug?" and then I have to reconnect the whole thing.
Import/Export Is A Nightmare
Migrating from Jira was a clusterfuck. Took forever and we lost a bunch of custom fields. Don't even get me started on trying to maintain relationships between epics and stories. I spent way too much time manually recreating historical data that should have just imported.
Mobile App Is Garbage
The iOS app crashes if you try to add more than 2 attachments to an issue. The Android app doesn't sync reliably. If you need to triage issues on your phone, just use the web app and squint.
Month 6: The Verdict
Here's who should use Linear:
- Engineering teams of 5-50 people
- Startups that value speed over process
- Teams that don't need fancy reporting for executives
- Organizations where engineers have significant input on tooling decisions
Here's who shouldn't:
- Companies with complex compliance requirements
- Teams that need detailed project management features
- Organizations where PMs run the show
- Anyone who needs integrations beyond GitHub/Slack/the basics
Would I switch back to Jira? Fuck no. Would I recommend Linear to every team? Also no. It's a tool with strong opinions, and if those opinions align with how your team works, you'll love it. If they don't, you'll hate it.
The honest truth: our engineering team loves it, but it pissed off our PM and the design team gave up trying to use it. We're still using it because the engineers who make the decisions are happy, even if it created some organizational headaches.
Your mileage may vary, but at least now you know what you're signing up for.
