I want help with the remembering

This week from Allie

I stepped away from being totally obsessed with AI for about ten days because we were moving house.

“Stepped away” is an exaggeration. I was still consuming AI-focused Substacks and podcasts and using AI every day. It just wasn’t my primary focus.

When I turned my attention back, it felt as though everyone had a new personal AI assistant: Muse, Grok Bot, Instinct, dot. Honestly, I’m feeling a little at sea. I co-run Open Hours, I love these tools, and they help me every day. But the feeling that there’s always something else in the AI-verse that I should be trying can get overwhelming.

What’s different about these assistants

Most of us use ChatGPT or Claude by asking. You open a chat, explain what you need and get help. The new personal assistants promise to work the other way around: you connect your accounts once, and they flag things before you think to ask.

Catey tried one of them, Instinct, in September, when she needed a 63-page ballet handbook turned into a usable PDF. It did the job, but she stopped short of telling it about her kids before she’d read its privacy policy.

I’ve been experimenting with dot in ChatGPT. A caveat up front: for personal accounts, dot is currently rolling out on eligible ChatGPT Pro plans, starting at $100 a month. I spend a lot of time trying these tools. I wouldn’t suggest paying that just to check your family calendar.

Here’s what I liked. It fit easily into my existing setup, with accounts connected and privacy settings I understood. In the first 24 hours, it flagged that my dentist appointment overlapped with a meeting, spotted subscriptions I might want to cancel, and noticed deliveries still going to our old address. It also helped me set up a check for evenings when we’d need a babysitter.

That’s the bit that clicked: I want help with the remembering. Something that catches a detail when my head is full, before I remember to ask.

Every new assistant is a project

Signing up for an AI personal assistant might take five minutes. Deciding what to use it for, what information to share and how it fits into your habits takes longer. Multiply that by four assistants and it adds up.

What helped was picking up a pen and asking, “What am I trying to achieve here?” What came up for me was: more mental space, less stress, a system that works for my family.

That led to a more useful question: of the things dot caught, how many could I already do with the tools I had?

Most of them. Each catch was a job I could describe. Check my calendar for clashes. Review these subscriptions. Find deliveries still going to the old address. Work out when we need childcare. ChatGPT and Claude can do any of those today. The difference is that you have to ask. Once a check works, though, you can schedule it, and then you only have to ask once.

You don’t have to figure out a whole new personal assistant before getting help with one thing.

Try this

One less thing to keep track of

Write down one thing you’re tired of remembering. If subscriptions have been piling up, start there. Download your last two months of card statements, or paste in the transactions you’re comfortable sharing, and try:

“Here are my last two months of card transactions. List every recurring charge: what it is, how much, how often and when it last charged. Flag anything that looks like a duplicate, a free trial that turned into a paid plan, or something I may have stopped using. Ask me about any charge you can’t identify rather than guessing. Don’t cancel anything.”

Check the list against your statements, and do any cancelling yourself.

Calendar clashes are another good first job. Connect your calendar using our step-by-step guide, or paste in the appointments you’re comfortable sharing. Then try:

“Look at the next two weeks of my calendar. First, tell me what information you can see. Flag overlapping appointments and anything too close together once travel time is included. Ask me about any missing details rather than guessing. Give me a short list of what needs my attention. Don’t change anything.”

Want to make it a regular check? A calendar check needs a connected calendar so it can see new and changed appointments. A subscription review can run monthly on a fresh statement. In ChatGPT, ask it to save a scheduled task. In Claude, use Scheduled in Cowork.

If you’re unsure how to set it up, ask ChatGPT or Claude to walk you through it:

“Help me set this up to run every [weekday / month] at [pick your time] in [your time zone]. Guide me one step at a time, and confirm how I’ll receive the results.”

Availability depends on your plan and setup; Claude scheduling requires a paid plan. Confirm the task appears in Scheduled and review the first few runs. If scheduling isn’t available, save the prompt and run it when you plan your week.

I still want to experiment with the other assistants. I just haven’t had time yet. In the meantime, dot gave me a list of things to ask for, and the tools I already have can handle most of them.

Allie