How I Used Claude Cowork to Automate the Tasks That Never Got Done
There is a certain kind of task that lives on the to-do list forever. You know the one. It's not that it's hard. It just needs a specific block of focused time — and for solopreneurs running lean on capacity, that block never quite shows up.
For me, that task was auditing every link on my YouTube channel for broken ones. My VA and I both knew it needed to happen. It kept getting bumped. And then I started experimenting with a tool called Claude Cowork — and that task finally got done. In about ten minutes.
Here's exactly what I did, what the output looked like, and how I set it up to never fall through the cracks again.
Either keep reading or watch the video below:
What Is Claude Cowork?
Claude Cowork is an AI tool from Anthropic that handles tasks and workflows on your behalf — pulling information, creating outputs, and connecting to the tools you already use. Think of it less like a chatbot and more like an assistant that can actually go do the thing, not just tell you how to do it.
For solopreneurs and small teams, the most useful part is that you can set tasks to recur. So instead of a one-time job, you're building a small system — one that runs quietly in the background while you work on everything else.
Task 1: Auditing Broken Links on My YouTube Channel
Every YouTube description I've ever published has links in it — to products, resources, affiliate tools. Over time, some of those links break. URLs change. Products get updated. Pages disappear. And if you don't catch them, you're quietly sending people to dead ends.
I gave Cowork one job: go through my YouTube channel, find every broken link, and create an Asana task with a Google Doc attached listing everything that needs to be changed. No instructions needed from me beyond that. No back and forth.
The output was exactly what I described. My VA had a task waiting for her with everything she needed — the links, the context, and a clear action. I didn't have to write a brief. I didn't have to find anything myself. It was just handled.
And then I set it as a recurring task. Now it runs on a schedule. Every cycle, a new Asana task appears with whatever needs updating. I don't have to remember to check. I don't have to carve out time for it. It's built into the system.
Task 2: Mining My Email Stats for Top Performers
The second thing I set up is the one I'm most excited about.
I asked Cowork to go through my email marketing stats and pull out my top performing emails — the ones with the highest open rates, click through rates, and actual sales attributed. Then I wanted two things from that data.
First, I wanted those emails added to my content calendar to be resent after at least six months. If an email performed well once, it'll likely perform well again — especially for subscribers who weren't on the list the first time around.
Second, I wanted spin-off ideas generated from each top performer. Related angles I haven't tested yet. And I wanted those ideas added to Asana as a task for me to review when I have capacity.
The result is a content calendar that feeds itself from proven data, plus a running idea list I didn't have to brainstorm from scratch. And again — this is a recurring task. It just runs.
Why This Matters for Solopreneurs
The tasks that live on the list forever are rarely complicated. They're ignored because they need focused time — and for a solopreneur working in small, unpredictable windows, that's often the scarcest resource there is.
This is especially true if you're neurodivergent, working around parenting or health, or running a lean team with part-time support. The task doesn't become less important just because capacity is limited.
What tools like Cowork make possible is getting those tasks done once and then keeping them done — set up to recur, outputting into the systems you already use, without needing your attention every time.
That's not magic. That's just a better system.
How to Figure Out What to Hand Off
The most useful question to ask yourself is: what is the task I keep moving to next week?
Not the tasks that are genuinely complex or require your judgment — but the tasks that are important, documented or documentable, and just never seem to make it to the top of the list.
Those are the ones worth setting up first. Start with one. See what the output looks like. Refine it. Then set it to recur.
If you want help thinking through what that looks like for your specific business — what to hand off, how to set it up, and how to make it connect with your existing Asana system — that's exactly what my Back-Pocket Support is for. You can learn more and apply here.
