The Spreadsheet That Made Me Question Everything
I was staring at a spreadsheet with 47 different tasks I wanted to automate. Customer follow-ups, social media scheduling, data entry, invoice reminders, lead tracking, content repurposing — the list went on and on. I’d spent three hours just brainstorming all the things that ate up my time every week.
And then I froze. Where do I even start?
I had access to automation tools. I’d watched tutorials. I understood the basic concepts. But nobody told me how to pick which task to tackle first. So I did what most people do — I picked the flashiest one. The complex multi-step workflow that would theoretically save hours every week.
Three weeks later, I’d built nothing. The project was too complicated, I got frustrated, and that spreadsheet collected digital dust while I kept doing everything manually.
The Real Problem Nobody Talks About
Here’s what I’ve learned after finally building systems that actually work: the hardest part of automation isn’t the technical setup. It’s choosing what to automate first.
Pick wrong, and you’ll waste weeks on a complex project that breaks constantly. Pick right, and you’ll build momentum that carries you through increasingly sophisticated automations. The difference between people who successfully automate their workflows and people who give up isn’t technical skill — it’s strategy.
Most of us approach automation like kids in a candy store. We see all these possibilities and want everything at once. But that approach almost always leads to overwhelm and abandoned projects.
The Framework That Changed How I Think About This
After that failed first attempt, I stepped back and developed a simple scoring system. Every task I considered automating got rated on three factors: frequency, simplicity, and annoyance level.
Frequency means how often you do the task. Something you do daily beats something you do monthly. Simplicity means how straightforward the task is — does it follow the same steps every time, or does it require judgment calls? Annoyance level is subjective but important — how much do you dread this task?
I started scoring each potential automation on a scale of 1-5 for each factor, then adding them up. The highest scores pointed me toward my best starting points.
Putting the Framework Into Practice
When I applied this to my own list, something interesting happened. That complex multi-step workflow I’d originally chosen? It scored a 7. High frequency and high annoyance, but almost no simplicity — it required different approaches depending on context.
But a simple task I’d overlooked — sending a welcome message to new email subscribers — scored a 13. I did it daily, it followed the exact same steps every time, and I found it tedious enough to procrastinate on it regularly.
I built that automation in under an hour using a free automation tool connected to my email platform. It worked perfectly from day one. More importantly, it gave me confidence that this stuff actually worked.
From there, I tackled the next highest-scoring task. Then the next. Each small win taught me something new about how automation tools function, and suddenly those complex workflows didn’t seem so intimidating.
What Actually Changed
Within a month, I had five simple automations running smoothly. None of them were impressive on their own — sending welcome sequences, organizing files into folders, creating tasks from form submissions, posting reminders to my calendar, and backing up important data.
But collectively? I estimated I was saving around six hours every week. More importantly, I stopped forgetting things. The mental load of remembering all these small tasks disappeared.
That complex workflow I’d originally wanted to build? I finally tackled it three months later, after I’d developed actual skills from those simpler projects. It took me two days instead of three weeks, and it worked on the first try.
Key Takeaways for Choosing Your First Automation
Start boring. The most successful first automations are usually the ones that seem too simple to bother with. That simplicity is exactly why they work.
Look for tasks you do the same way every single time. If you ever have to think about what to do next, the task probably isn’t ready for automation yet. Save those for later.
Prioritize frequency over time saved per instance. Automating something that saves you two minutes but happens twenty times a week beats automating something that saves thirty minutes once a month.
Pay attention to your emotional resistance. Tasks you consistently procrastinate on are great candidates because automation removes the psychological barrier entirely.
Build momentum before building complexity. Each simple automation teaches you something. Those lessons compound when you tackle bigger projects.
Your Next Step
Grab a piece of paper and write down every repetitive task you do in a typical week. Don’t filter yourself — just brain dump everything. Then score each one on frequency, simplicity, and annoyance level. The highest scorer is probably your ideal first automation project.
You might be surprised what rises to the top. It probably won’t be the flashy system you initially imagined. But that’s the point. Start small, build skills, and let complexity come naturally.
This article is for educational purposes only. Results vary based on individual effort and circumstances.
Want to learn the exact tools and systems I use? Get the free resource guide at snapsidehustles.com