User Error! How a Tech Mistake Made Her a Better Business Owner

Sometimes the most well intentioned, tech savvy entrepreneur struggles with the day-to-day operations and intricacies of running a small business.

And today, we’re sharing one such entrepreneur’s story. 

Jackie is the founder of a growing online coaching business, a mom of two, and self-proclaimed “self taught IT support specialist.” Like many service-based entrepreneurs, she wears all the hats at the same time - CEO, marketer, customer service rep, and in-house IT department.

Her business runs on a mix of deep passion, hot coffee, and carefully built systems… which is why the day she fumbled one of her own most valuable automations felt more like a crisis than an ‘oops’. What started as a small mistake quickly turned into a crash course in how to recover, rebuild, and come out even stronger.

The Mistake

It happened on an ordinary Tuesday during a busy work week. Jackie was laying out a new email campaign, prepping for a client call, and updating a sales automation all at once - because that’s what a multi-tasking entrepreneur does!  

In her rush to finish up, and be able to grab a snack before her call, she skipped her usual testing process for the sales automation. She’d been doing this so long, and they’ve always worked fine so she could forgo her usual last step.  

Except this time, it wasn’t fine.

Within minutes of hitting publish, Jackie received a message in her inbox from someone on her email list and they were upset that they had received an email from the automation she had just published. 

She was confused and then realized that the person who had sent that email was on a segment of her email list that should not be getting sales emails. Ever. 

How did that happen?!

Immediately Jackie pulled up her CRM and started to look for where the tech had failed. It was then that she realized - it hadn’t been the tech, it was her. Plain old human error. 

The automation had gone live to the wrong segment of her list. A segment that had opted out of sales emails and this automation was a very direct selling campaign. In her rush to get through her tasks, and because she hadn’t run her normal test process and double checks, she’d emailed a large group of people that she shouldn’t have. 

It wasn’t a catastrophic blunder but it was one that was probably going to garner a bit of backlash and tarnish the trust she had been building with that particular audience. 

The Fallout

The moment she realized what she’d done, she froze. That pit-in-your-stomach feeling set in and the “Oh no!” thoughts started swirling:

• What if people think I don’t respect them?

• What if this ruins my credibility?

• What if I just broke everything?

And on top of the business related questions, Jackie was then looking at her already solid schedule and wondering when she was going to be able to fix the mistake.

It felt like one small mistake had tipped the domino. 

The Recovery Process

Here’s the thing we know to be true in the world of small business automation: the majority of the time, tech mishaps aren’t “tech” problems — they’re human error. 

But if we caused it, we can usually fix it! That’s the perspective shift that has helped so many entrepreneurs, like Jackie, go from panic to problem solving!

Once Jackie was able to quell her initial panic, she followed a simple process that had become the go-to for a lot of our clients.

Step 1: Evaluate 

Figure out exactly what happened and where. This may take a bit of time so be patient as you check each step.

Step 2: Communicate

For those impacted, send a quick, honest message about the oops and let them know that it’s being fixed right away.

Step 3: Fix

Repair what you can right away and, if needed, reach out to tech support to help you work through the solution.

Step 4: Document

To make sure this kind of mistake doesn’t happen again, write down what caused it and how you fixed it so you can prevent it in the future.

Jackie went through the 4 steps and within the hour had corrected the segmentation error and heard back from a few people confirming that all was well.  

What Jackie Learned

That seemingly small blunder taught Jackie more in that one day than months of smooth sailing business operation ever could. 

• Slowing down will always save time.

• Always test — no matter how routine the task feels.

• Have backup plans (and recovery steps) ready to go at all times.

• Mistakes don’t equal failure, they showcase your ability to address a crisis with a level head and a solid plan. 

Now, instead of dreading mistakes, Jackie sees them as part of the entrepreneur process. Each one strengthens her confidence because she knows she can handle it.

Following her automation oops, Jackie adopted a new task management system that made sure she always had the time to double check her work and run tests before anything got published.

And her business was better for it too!

For You, If You’ve Been There Before 

If you’ve ever broken something in your business — an automation, a link, an email — welcome to the club! You’re not bad at tech. You’re not bad at business. You’re just a solo business owner learning, testing, and building like the rest of us.

And the goal should never be perfection.

The goal should be to set yourself up so that when mistakes happen (and they will), you can recover quickly, learn from them, and keep moving forward.

That Tuesday taught Jackie one ultimate lesson: tech mistakes are rarely the end of the world — but they’re always an opportunity to improve your systems.

If you’ve been feeling overwhelmed, anxious or unsure about your tech setup, or want to create automations that actually work for you (even when things go wrong), the team at Automation on a Mission can help!

Supporting you as you build your business with personalized systems, processes and solutions is what we do best!

Book a free call today and let’s make your systems simple, resilient, and confidence-boosting.