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May 20, 2021

The ultimate cloud migration: migrating from the cloud at 10,000 feet

00:00 hours, UTC, day 0: earth


It's late 2020 and I've decided to do the ultimate Cloud Migration:

I'm going to chuck myself out of a plane.

Or more accurately: be chucked.

Why? We'll come back to that later.

15:33 hours, UTC, day 4: earth


Initial experiments with finding compatriots have failed. See actual transcript of internet activity:

Jack totally abstract shower thought I had while waiting for docker images to pull over bad 4g: are skydives Cloud Migrations? Come find out 3rd April at 7.30 am, in an airfield near you. @CutoverCTO want to join?

Cutover CTO No way. I'm scared of roller coasters. Haha. Good luck though I can definitely come and watch.

Questions: How come my bosses' bosses' boss' is such a wimp? I'll have to do it alone.

15:33 hours, UTC, day 14: Earth


It appears my initial discretion has failed. It appears one can't simply deploy a parachute nowadays:

Cutover CMO Hi! Love your cloud migration idea, is it real? 

Jack Fenton Oh, so the rumour is out! It's real, I think - should I do it, but socially distanced? No colleagues allowed? (unless you want to migrate through the clouds with me)? COVID-19 and that? 

Other people at Cutover No! We're coming too - we have pom-poms!

21:33 hours, UTC, day 14: earth


I think truly and deeply about what I have done. I am fully going to have to do this now - other people are involved.

Sure, I instinctively knew that the ‘deploy’ pun and Cloud Migration in-joke would be popular, but I didn't really think this through.

Like our CTO, I am afraid of flights.

Like most people, I don't want to fall to my death.

Like other Cloud Engineers, I prefer steering a code ship into a Suez-canal-type situation to hurtling through the atmosphere.

But I think a little deeper and realise that's fine, this is great - there are so many analogous links between Jumping Out Of A Plane and chucking some software into the Cloud: they are both high-pressure, high-intensity procedures with so much that can go wrong. They are both riddled with security issues/backup processes/hands-free situations.

Is a tandem skydive as scary as deploying to a gigantic FinTech company's servers? Well not quite, but it's close.

And what better tool for using when your hands are tied hurtling through space than Cutover?

When you're doing a Cloud Migration (in software) you're usually tongue-tied, with hands locked up, an eye on AWS, an eye on some Observability, eyes on Slack; more eyes on the code you're running - you need more eyes. 

Of the two hands you do have, one is on the mouse switching tabs and one is on the keyboard barking out commands.

You're kind of screwed if something goes wrong, as you have to take those hands or eyes off the prizes and focus on comms.

It's almost as if you need a tool to be your tandem instructor, watching your back and saving your life. Checking your parachute is safe and making sure it opens properly. Linking you with your co-pilots.

This idea makes sense. I just have to jump out of a plane to prove it.

And I am emotionally under-prepared.

But I suppose my Cutover colleagues will be there for on-site backup: all I have to do is turn up.

13:00 hours, UTC, day 34: Earth


Living in denial has its benefits. I have hardly thought about it, but others have.

I've been asked if I am ready. Asked if I am scared. Asked if I am going to film it.

To be honest I didn't really have answers but as my hand is forced these are my conclusions:

No, I am not ready, but I've learned a bit.

I've learned I have to be under 100kg to fly, I have to be there by 9 am, and that there are sausage sandwiches.

Am I scared? Not yet.

Will I be? Oh yes.

Am I going to film it? Yes.

Several Cutover diehards are coming along to capture the day. They really have pom-poms.

I've booked the skydive itself for after restrictions are lifted (not that they were open before) and it's going to be my first day in public.

Baptism of fire much?

05:00 hours, UTC, day 64: Oxfordshire


It's been a long time planning now, and I am hoping things will go alright on the day. Like a software deployment. 

I, again, imagine a Cutover runbook for tandem instructors going through the motions of every jump. Safety this, safety that, checklist 1, 2, 3. I imagine what happens when, despite all the careful planning, you go splat on the floor as your parachute hasn't been used since lockdown, and the instructor forgot how to fly. I imagine this is what happens when you meet colleagues (some of who you haven't met in real life) in a field in the UK countryside and the first thing you do is splat on the floor and die.

To be honest I'd rather fail a deployment to a big Financial Institute than embarrass myself like that.

Oh well, I suppose it'll be quick.

You can tell I woke up worrying this morning,

09:13 hours, UTC, day 67: Oxfordshire


I skydive tomorrow.

The weather is really bright and amazing and clear.

It's not going to be cancelled.

I am meeting colleagues on the airstrip.

I Google the day again and I learn that a deploy computer called a Cypress 2 sits in our harness and deploys a backup parachute if we pass 8,000ft and, presumably, the instructor is a homicidal maniac or asleep and hasn't done it yet.

This is like a rollback - automated systems to cover up a failed deployment. Technology powering it.

I wonder how Cutover feels when deployments to it fail. Does software get scared? 

Am I going to be alright in the morning?

Maybe the car will break down. I’d better leave five hours early.

Maybe I should pretend my car broke down.

I should have made a runbook just to get there.

06:01 hours, UTC, day 68: Oxfordshire


We're driving to the airfield and I pay myself off with junk food at the services (two hours early due to a lack of engine failure).

08:02 hours, UTC, day 68: Oxfordshire


I'm on the runway. I've passed the security journey and safety instructions and I'm waiting for my name to be called from a big loudspeaker. I am honestly more scared than I ever thought I would be. My partner hugs me, scared too. I want a sausage sandwich.

I see Cutover colleagues floating up the runway towards me, all matching pink hoodies and smiles.

Talking distracts me. Nervous chatting blocks out the sound of the klaxon and the announcement of my name which I miss.

My colleagues inform me that yes, that really was my name.

I'm going to die!

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For any concerned parties, we can confirm via video footage that Jack did indeed survive his migration from cloud to land successfully. 


But what about your next deployment? If you would like to take the fear out of your next migration, release, or deployment, find out more about how Cutover can support a smooth orchestration across teams and technologies and help you land safely every time. 


Or, why not check out The journey to the cloud: Lessons learned from working with major organizations

Jack Fenton
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