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Hi Reader 👋 Hope you're having an amazing Thursday!

Data entry is one of those jobs that drains your energy fast. It’s the kind of work that makes you question your life choices. When did you become a cog in the knowledge-worker machine?

But if you’re running a business, or even just trying to keep your team organised, you can’t skip it. You need those categories for reporting, for insights, for making better decisions.

So you grit your teeth and get to work… or do you?

That was me last week. I had a backlog of about 1,000 tasks. Each one needed to be categorised so I could pull the right analytics and spot trends.

Normally, I’d block out a couple of hours, put on the How I Write podcast (which is amazing and everyone even remotely interested in writing should check out), and start clicking through each task, one by one. It’s not glamorous, but it’s necessary. Or at least, it used to be.

Here’s where things have changed with ClickUp AI custom fields.

I’d been playing around with ClickUp’s AI features for a while, but hadn't really put them to any good use. This time, I decided to see if it could help me categorise everything. I set up a custom AI field with instructions tailored to my categories. Instead of just using the default suggestions, I told the AI exactly what I wanted:

Then I hit the “bulk generate” button. I watched as the AI filled out the custom field for nearly every single task. No more manual sorting. No more second-guessing. In less than five minutes, the job was done. And I think the only reason it didn't fill out all the fields was because my instructions weren't quite detailed enough.

What used to take me two hours now took less than the time it takes to make a coffee. And the were spot on. The categories matched my criteria, and I could immediately start pulling the analytics I needed on a ClickUp dashboard.

Why does this matter? Because time is your most valuable resource. Every hour you spend on repetitive admin is an hour you’re not spending on strategy, growth, or even just taking a break.

A few tips if you want to try this yourself:

1. Be specific with your AI instructions. The more context you give, the better the results. (do a better job than I did with my prompt)
2. Use the bulk generate feature for big lists. It’s a massive time saver.
3. Double-check a few entries to make sure the AI is following your logic. Tweak your instructions if needed.

I’ve started using AI custom fields for all sorts of repetitive tasks now: tagging content, assigning priorities, even drafting quick newsletters based on social media posts I've done.

If you’re still doing manual data entry in 2025, you’re missing out. Give ClickUp AI custom fields a try and let me know how it goes. I’d love to hear what you automate next.

Need help with AI workflows or your ClickUp setup? Book a 1-hour call with me and I'll solve your biggest productivity bottlenecks — paying for itself by saving you hours every week.

See you next week!