How to Choose the Right Automation (So It Actually Helps You)

Because a broken shortcut isn’t a shortcut at all.

"Sustainable organizing requires infrastructure that doesn’t rely on heroic effort." - Dean Spade

It’s easy to get excited about automation. Less manual work! More time back! But if you’ve ever set up an automation that quietly stopped working (or made a bigger mess than you started with) you know the reality: not every shortcut is a good one.

This isn’t a list of tools. It’s a way to think through what you actually need, before you start building. Whether you're automating your business backend or just trying to simplify one task, these five questions will help you create systems that don’t just work, but keep working.

1. What’s the real problem?

Start here. Not with a tool, not with a trick; with the actual problem you want to stop running into.

Instead of:

“I want to automate my invoicing.”

Try:

“I want to stop sending late invoices, and I don’t want to copy info from three different places every time.”

Naming the problem clearly gives you a better chance of solving it cleanly.

2. Is it more important that this is fast, or that it’s reliable?

Some things are worth rushing. Most things aren’t. Especially when money, time, or people are involved.

Ask yourself:

• Will I ever need to double-check this before it goes out?

• Would I even notice if something stopped working?

• If something goes wrong, how will I catch it?

If you don’t have answers to those questions, slow down. The best automation isn’t the fastest, it’s the one you don’t have to clean up after.

3. What kind of support are you really asking for?

There are lots of tools that say they "automate." The trick is choosing the one that fits the task:

What you need to do	What kind of tool helps
Move info from one place to another	A connector like Zapier
Trigger something when you take action	Built-in automations in your tool (like Airtable or Notion)
Automatically calculate or fill in values	A formula or rule inside your tool
Make it easier to see what’s going on	A dashboard or visual layout

If you’re not sure what kind of support you need, describe what you wish would happen and then look for tools that make that kind of thing easier.

4. What could go wrong?

Seriously. Imagine it breaks. Then imagine you don’t know it broke until next week.

Now ask:

• Is there a way to get a heads-up if something doesn’t go through?

• Is there somewhere I can check whether it’s working?

• Will I remember how this works a month from now?

If the answer to any of these is no, the automation isn’t ready yet. It might still be worth doing, but manually.

5. Will it still make sense when I’m tired, busy, or not the one using it?

The best automation is one you can forget about. Not because it disappears, but because it’s steady. Clear. Predictable.

Before you hit “done,” ask:

• Will this still make sense if I come back to it after a break?

• Can I explain it to someone else in one or two sentences?

• If it stops working, will I know where to look?

If the answer is yes, that’s a system worth keeping.

Final Thought

Automation isn’t just about saving time. It’s about protecting your focus and designing for ease you can trust. If something's working for you don’t rush to replace it with something faster. Start by making sure you understand the shape of what you need.

Then build something that will stand up to real life, not just a perfect day.