Jira
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Cloud Migration

The Cloud Migration Diaries: Your Jira, in Purgatory

Garth Leavey
April 8, 2025
3
min read

1. Welcome to the Cloud. Also: Abandon all hope.

It started with a click.

“Initiate migration.”

You paused. Looked out the window.

The world was still there.

You clicked.

Three hours later, you’re staring into a Confluence page titled Migration Checklist Final FINAL v9 (Copy). You’ve become that person. The one who used to mock anyone with nine versions of a spreadsheet. Now you are the spreadsheet. You feel… migrated.

But not in a good way.


2. The Great Betrayal: Your Jira Projects Have Left the Building

Your Jira issues?

They made the jump. Kind of.

Except every link is broken. Epics point to dead stories. Attachments have vanished into the ether like a doomed Mars rover.

Custom fields? Gone rogue.

Automation rules? Inherited trauma from server days.

Your dev team now communicates exclusively through Slack emojis and gritted teeth.

QA has started drinking at lunch.

You’re not sure if it’s Tuesday or still last Thursday.

3. IT Is Dead. Long Live Atlassian Support.

You opened a support ticket.

They replied with a link to documentation written in the pre-Cambrian era.

Your response was a meme.

They responded with another link.

You’re now trapped in a Kafkaesque game of Jira Jeopardy where every answer is phrased as a question.


4. Meanwhile, the Business Asks: “Is It Done Yet?”

“Shouldn’t this just work?”

That’s what the CFO asked.

You considered responding with a PowerPoint deck called “The Myth of Seamless Cloud Migrations: A Tragedy in Five Acts”,

but instead, you just said,

“Almost.”

(Lie.)


5. Enter SelectStar: The Anti-Existential Crisis

Here’s the thing:

Cloud migrations don’t have to feel like a reboot of Lost, where every character is a confused Jira admin, and the Smoke Monster is a broken field mapping.

SelectStar doesn’t just do “lift and shift.”

They do lift, dust, re-architect, align, optimize, emotionally support, and educate.

They bring:

  • Atlassian-certified specialists who actually know what a Forge app is.
  • Migration strategies that don’t result in Slack therapy sessions.
  • Change management plans that treat your humans like humans.
  • Post-migration cleanup that doesn’t involve a sacrificial offering to the Configuration Gods.

They’ve done this for energy companies, finance firms, startups, non-profits, and probably a goat farm once (ask them about it).

6. Choose Your Own Ending

There are two kinds of companies:

  1. The ones who try to DIY their migration and end up hiring SelectStar to fix it.
  2. The ones who hire SelectStar first.

Both get there.

Only one of them keeps their weekend.

TL;DR

Cloud is the future. But the road there is full of Jira zombies, broken workflows, and documentation that might be written by sentient AIs with a grudge.

SelectStar is your migration Sherpa, translator, therapist, and operations guru rolled into one.

Because Cloud should feel like progress—not punishment.

Let me know if you want to make this into a LinkedIn post, presentation, or animated explainer narrated by a slightly sarcastic Canadian voiceover.

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Jira
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