What to Do When Your Tech Fails in Your Online Business

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Welcome to running an online business.

Tech fails aren’t a matter of if. They’re a matter of when. And if you’ve been in business for more than 30 seconds, you already know that these moments can send your nervous system into overdrive.

So what do you do when the very systems you’ve spent weeks building start breaking in real time?

While it sucks in the moment (because of course it happens when you’re finally feeling on top of things), how you handle those tech fails in your online business is what separates the pros from the panic-googlers.

So, in the spirit of keeping things real, let’s talk about a few of my favorite tech fails—mine and others’—and what you can learn from them.

The “Why Won’t This Damn Form Work?” Saga

When I was setting up the Automagic Summit, every speaker got their own page. On that page, I added a simple feedback form so attendees could share what they loved about each session. Easy, right?

Except one page refused to cooperate.

I rebuilt it. I cloned it. I even created a brand-new form from scratch. Nothing.

After wasting way too much time, I finally gave up and just added a button that linked to the form instead. Not ideal, but functional.

The moral? Sometimes “done and working” beats “perfect but broken.” There’s a point where troubleshooting becomes time-wasting.

Recognize it, fix it enough to move forward, and get back to the work that actually matters.

The PayPal Tagging Nightmare

When I launched the VIP Pass for the summit, everything tested perfectly. Credit-card checkouts? Smooth. Tags applied? Automations fired? Flawless.

Then someone paid with PayPal.

Turns out, that specific payment path wasn’t working correctly—so no automation, no welcome email, no “thanks for buying” message. (And yeah, that’s the kind of experience that keeps me awake at night.)

Luckily, only one buyer slipped through before I caught it. But it was a great reminder: automations don’t mean autopilot.

Even when your systems are solid, you still need to check in once in a while. Run a test payment. Verify tags. Make sure nothing’s quietly breaking in the background.

The Website Meltdown That Changed Everything

My biggest fail? Oh, that would be when my entire website went down—in the middle of my first big launch.

We’re talking total blackout. No login access. No workaround. Just me on the phone with support for 13 hours over multiple days while the clock ticked down on my masterclass registration window.

The launch tanked, obviously.

And when the dust settled, I realized I’d wasted months learning how to custom-code that site instead of focusing on, you know, actually running my business.

That was my turning point. I rebuilt everything from scratch—this time on a platform that wouldn’t implode every time I blinked—and promised myself I’d stop obsessing over the perfect twirly font and start spending my time on strategy, not setup.

That experience is exactly why The Shortcut exists today: so other business owners don’t lose months of progress trying to fix something that shouldn’t be their problem in the first place.

You’re Not the Only One

Even the best of us get hit. One of the Automagic speakers, Shelby Dennis, had her entire domain host go down the day after sending me her summit materials. She had to rebuild and resend everything with new links, right before a weekend when tech support was of course MIA.

But she handled it like a pro: updated her links, reached out quickly, and stayed calm. (Okay, maybe slightly panicked—but she pulled it off.)

Her story and mine both prove the same thing: tech fails aren’t an “if,” they’re a “when.” What matters is how fast you recover—and whether you protect your relationships in the process.

What to Do When Tech Fails in Your Online Business

When (again, not if) tech breaks, here’s what to do:

• Pause before panicking. Give yourself a minute to swear, scream, or stomp it out. Then start troubleshooting.

• Communicate fast. If a client or buyer might be affected, tell them right away. Transparency builds trust.

• Have a backup plan. Keep extra payment methods, test accounts, or templates handy so you can pivot quickly.

• Know your systems. You don’t have to do all the tech yourself—but you should understand how it works so you’re never totally powerless.

• Fix it, then document it. Every problem you solve should become a note or SOP so you don’t repeat the same mistake later.

Final Thoughts

At some point, some piece of tech will fail in your business. That’s not pessimism—it’s business reality.

But every time it does, you’re given a chance to show your audience (and yourself!) that you can handle chaos with professionalism and grace.

Because running a successful online business isn’t about avoiding problems. It’s about staying calm, solving them, and moving forward smarter than before.