I Am My Own Worst AI Enemy
Down the rabbit hole again... but at least I packed coffee this time
A couple of weeks ago, I shared that I was focused on using AI to buy my time back. I had a little chat with Claude about what would be the best automations to start with to help me free up my time.
Welcome to the rabbit hole that only got deeper with no end in sight.
I also shared a while back that AI can and should be used for “just in time learning” (and learning in general - we live in a world that thinks everything needs to be monetized and I don’t think this is talked about enough, but I digress) - something I seemed to forget as I went down my little automation rabbit hole.
I’ll briefly share the automations Claude suggested I set up and then explain how this rabbit hole got deeper and deeper.
Here are the six automations Claude suggested:
AI Intelligence Digest: Reads the RSS feeds of AI newsletters, sends me one email with a recap.
YouTube → Content System: New video → generates blog post, newsletter, social posts, email.
Client Onboarding Automation: Tag “New Client” in Notion → sends welcome, schedules meeting, creates project setup.
Weekly Content Batch Automation: Every Monday 6am → generates weekly content plan and draft posts for me to edit/adjust.
Substack → Kit Segmentation Flow: New subscribers automatically tagged based on engagement.
Social Content Curation (Women in AI): Monitors feeds of women creators, generates share-worthy posts with your commentary.
They all sound pretty good, right?
I created the first one (AI Intelligence Digest) using n8n via Railway - which is hosting it. This is similar to how you can use WordPress dot com - the hosted version from WordPress OR you can self-host WordPress using WordPress dot org and a host of your choosing.
If you’re not familiar with n8n, think Zapier but more more technical (and self-hosted is a lot cheaper than using Zapier).
However… if it costs you hours and hours of your time, what are you saving? (and I’m still dealing with a bug- which is what inspired this post).
Keep in mind the time you spend with the initial set up will save you time in the long run, but there’s an even more important question to ask here - that can be applied to everything and is a basic fundamental of business is…
“Is this a priority?”
I know, I know. This seems like a ‘duh’ moment, but I know like many other things in life, it’s a process.
AI is moving at a speed unlike any other technology we have ever seen. It’s exciting, it’s a little scary, and it can be overwhelming.
I truly enjoy discovering new tools (I did this when I was ‘The WordPress Chick’ also - this has been part of my entire online journey), but I’ve never felt the need to try them all (contrary to how it may seem, lol).
After being off for almost two weeks with my little head injury, it felt like I had been off for months with everything that happened with AI.
The beauty of this was that it was like shining a spotlight on the fact that you can’t keep up with it… and more importantly, you don’t have to.
As soon as you figure out one thing something else comes out or the tool you’ve been using improves.
Which brings me back to good ol’ fundamentals and principles.
For starters, just because you can, doesn’t mean you should.
To give you a little more context…
I have zero employees or contractors in my business right now. And I love it. 🥰
I had an outsourcing company, I’ve had project managers, and then a handful of contractors I worked with on a regular basis. It added a level of stress I don’t want.
I absolutely love not having a team.
However, I also know at some point in order to do what I’m planning on doing I will probably need a couple of people. But I have zero desire to ever have more than 2-3 people I’ve contracted with (I don’t want employees).
This is when I realized that taking a step back, assessing fundamentals and principles that line up with my values was more important than creating automations.
Back to the automations Claude suggested I create.
For starters, I already have an automation set up with Make to send Substack email subscribers into Kit (note to self: update your project in Claude with the tools and processes you already have in place).
The AI Intelligence Digest is really a “nice to have,” but not necessary. Part of how I start my day when I get to my desk is to take my time with my coffee reading newsletters and curating.
And I thoroughly enjoy it.
It reminds me a bit of when I used to sit for a couple of hours on a Sunday morning with my coffee and the newspaper… which I loved.
Why would I take that away from myself?
As far as Content Automations, I need to step back and think about what would be most helpful. Not just “what can I automate.”
I love what I do and I don’t want to take away the work that inspires me just because it takes me longer than AI to accomplish something.
As for the rest of the automations?
I need to go back to the drawing board with more context (I think I’ll try testing the new ‘skills’ feature in Claude for a new project on automations). I’ll set up a new project, add skills to it, and all relevant context needed.
This is creating the guardrails for how I want to use AI… not just get pulled along for the ride.
The beauty of having these realizations at this stage in my life (midlife) is that I have so much more patience and grace for myself.
I don’t look at anything I’ve done or am testing with AI (yes, I’m still building apps) as a waste of time.
I have learned so, so much this year and I’m having a ball.
And if we’re not enjoying the journey, what’s the point?
I have no doubt I’ll send myself down another rabbit hole with AI because it’s fun. 😉
Some might be worth it, some won’t.
But that’s how I learn.
As long as the fundamentals are in place and my rabbit hole doesn’t cause things to fall through the cracks, I’m fine with it.
Everything about how we do business online is changing. Let’s give ourselves some grace and know that we all have different learning curves.




The time suck is real! Sometimes it's not worth the up front cost even for what it might be able to do later.
What is meant by "Substack → Kit Segmentation Flow: New subscribers automatically tagged based on engagement."?
Especially the "based on engagement" part.
I also have co-existing Kit and Substack lists.
For me I just figured out I sync them every few months manually, that's enough.
I'm also interested in hearing what types of different content your subscribers receive from Substack and Kit. :)