Lessons from 5 Failed Attempts to Automate My Life

Lessons from 5 Failed Attempts to Automate My Life

Automation is supposed to simplify life, free up time, and make us more efficient. But sometimes, the road to automation feels like anything but. Over the years, I’ve had my share of missteps—five, to be exact—that taught me priceless lessons about what doesn’t work when trying to automate life.

Here’s the raw truth, the failures, and what I learned along the way:

1. Automating Before Understanding

I jumped into automation thinking, If I can offload this, I’ll save time. But I hadn’t truly mapped out the process first. The result? Chaos. The automation failed because I didn’t fully understand the task I was trying to optimize.

Lesson: Take the time to break down the process. Understand the inputs, outputs, and bottlenecks before you automate anything.

2. Overcomplicating Simple Tasks

I thought every little thing needed a shiny tool or app. Before I knew it, I was managing multiple tools for things that were simpler on paper—like tracking daily habits.

Lesson: Not everything needs a complex system. Sometimes, a sticky note is more efficient than an app.

3. Choosing the Wrong Tools

I once automated my workflow using a tool that didn’t integrate with the apps I already relied on. It created more problems than it solved, forcing me to work around my automation instead of with it.

Lesson: Pick tools that align with your current systems, not ones that require a complete overhaul.

4. Neglecting Maintenance

Automation isn’t a “set it and forget it” solution. One of my automations broke down because I didn’t update it as my needs evolved. It ended up creating more manual work.

Lesson: Schedule regular check-ins to ensure your systems still meet your needs and are running smoothly.

5. Trying to Automate the Wrong Things

Some tasks require human intuition, creativity, or decision-making. I once tried automating client onboarding, only to realize it lacked the personal touch my clients valued most.

Lesson: Not everything can—or should—be automated. Prioritize automation for repetitive, low-value tasks and keep the human touch where it matters.

The Big Takeaway

Automation isn’t just about efficiency; it’s about intention. Each failed attempt taught me that automation works best when it’s grounded in clarity, simplicity, and alignment with your goals.

If you’re building systems for your business or life, don’t fear failure—it’s the best teacher. And if you need guidance, know that I’ve been through the trenches and can help you avoid these mistakes.

Let’s embrace progress, not perfection.

— JDD