The day our tech guy was on a plane and everything broke

It was just before 6am when my phone lit up.

Text after text. Alerts, pings, and a growing sense of dread.

The platform was down. Our SaaS product - the one hundreds of customers relied on - was completely offline. Logins were failing, data wasn’t loading, and support tickets were flying in.

I reached for the one person who could fix this fast.

Simon. Our technical genius.

The guy who built most of our infrastructure, who knew every workaround and caveat.

Straight to voicemail.

That’s when I remembered: he was on a long-haul flight to New York. Eight hours of radio silence at 35,000 feet. And our entire customer base was waiting.

The Moment You Realise You're Exposed

We thought we were safe. We'd just completed a major infrastructure upgrade. Everything was "modernised", scalable, secure. All the big stuff ticked.

But we’d overlooked one small, critical truth:

The entire system still depended on Simon.

When something broke, he fixed it. When a decision was needed, he made the call. And when push came to shove… well, no one else could. That morning was a wake-up call.

Not because something failed.

But because someone was unavailable - and that made everything fail.

Why This Matters to You

Every business has a “Simon”.

Sometimes it’s your tech lead. Sometimes it’s your bookkeeper. Sometimes it’s you.

They’re brilliant. Reliable. Trusted.

But they’re also holding more of the business together than you realise.

Until they’re unreachable.

The Fallout We (Barely) Recovered From

From the first ping to full recovery took seven hours.

It wasn’t catastrophic. But it was enough.

- Enough to scare us.

- Enough to lose sleep.

- Enough to make us realise we’d built a brittle business, wrapped in a slick exterior.

Simon landed, rolled up his sleeves, and fixed it in about an hour.

But it took us weeks to untangle the underlying issue: our systems looked robust, but they weren’t resilient.

What We Got Wrong

We’d done some documentation.

We had guides, diagrams, and walkthroughs.

But the stuff that mattered in a real emergency?

It lived in Simon’s head.

The undocumented fixes. The weird server quirks. The instinct built through years of tinkering.

All of it vanished the moment he boarded that flight.

We weren’t dealing with a tech problem. We were dealing with a dependency problem.

You Can’t Document Everything. But You Can Prepare.

Here’s the truth no one likes to admit:

You’ll never get everything out of someone’s head and into a playbook.

But you don’t need everything.

We focused on the 20% that mattered:

• The essentials that anyone else could follow in a pinch

• Clear escalation paths for emergencies

• A contact list for external experts who could step in

• Backup access to key tools, systems, and accounts

Not perfect. But enough to make us safe, not stuck.

This Isn't Just a Tech Issue

Once we saw how much we relied on Simon, we started looking elsewhere.

And it turns out… he wasn’t the only one holding up the ceiling.

My-founders. Our accountant. Our client manager. Me.

Everywhere we looked, we found single points of failure.

People who were brilliant, but irreplaceable. And therefore… dangerous.

The Real Test Came Later

A few years after "the Simon incident", I got cancer.

Six months out of the business. Too ill to think, never mind lead.

But that time, the business didn’t panic. It didn’t stall. It grew.

Why? Because we’d taken that first scare seriously.

We’d built systems that didn’t need any one person - not even me.

That, more than anything else, is why we survived.

This Week’s Challenge

Ask yourself one uncomfortable question:

If one key person in your business vanished tomorrow - would everything still work?

If the answer’s “maybe” or “I’m not sure” or “probably not”… start fixing it.

Begin with the biggest risk.

• Cross-train someone

• Write down the essentials

• Create emergency access

• Test it while you’re in control, not after you’re forced to

Don’t make the mistake we made.

Being Brilliant Isn’t Enough

Simon was brilliant. Still is.

But brilliance without backup is a business liability.

Because no matter how capable someone is, no one is available 24/7 forever.

1. Build your systems.

2. Create your safety nets.

3. Make people powerful - but not essential.

That’s the difference between a strong team and a fragile one.

And when life (or tech) throws you a curveball, that preparation becomes the best investment you ever made.