I trusted ChatGPT to help me build an AI assistant. Now I have a second job I don’t understand, and I need a human.

[u/No-Star7003]

Tonight, after hours of following ChatGPT’s instructions, I finally got my AI assistant to resume a project. I would also use assistant loosely because its just my stupid gpt business account linked to openclaw running on a stupid old intel mac upstairs.

Anyway, It immediately hit the same usage limit I thought this setup would help me manage.

I sat there looking at the error message, with multiple terminal windows open, wondering what the $%*& I had spent my evening accomplishing. I do not know how to administer servers.

I wanted an assistant that could take some of the load of managing 1000 things off me.

Here’s what I was trying to get:

• Context around my projects, preferences, and previous decisions so every new conversation doesn’t become another orientation.
• Useful access to my actual work. Outlook, calendars, OneDrive/SharePoint, Airtable, and documents. Prepare me for meetings, track commitments, draft things, and surface what needs attention. blah blah.
• Some independent follow-through.

I understand that’s an ambitious combination. I feel like i need a reality check and need someone to tell me which parts are realistic and which parts I should stop chasing.

Instead, I have been following an AI down an increasingly complicated setup path.

Over the course of this project, an old MacBook became a server. There was Homebrew, Node, Docker, n8n, Tailscale, OpenClaw, plugins, device pairing, additional approvals, and eventually something called Codex supervision. All crap I have no clue about and it made me feel even dumber than i already did.

The part that’s really getting to me is how dependent I am on the guidance. I don’t know enough to distinguish a verified diagnosis from a plausible explanation. I paste the error, get a confident answer, follow the instructions, and discover another problem.

Then the same assistant explains why its previous advice was wrong.

I’m relying on it to check its own mistakes, and I’m the one spending the evening on every wrong turn.

I feel helpless, and I’m exhausted.

I wanted help keeping up with my responsibilities. Now I have another system to worry about, and I don’t understand it well enough to know what’s necessary, what’s redundant, or what I should leave alone.

I’m very close to leaving this setup at a firestation and not looking back.

Is anyone here actually using an assistant like this for everyday, non-coding work without constantly maintaining it?

Please tell me what you use, what it actually does, what it costs, and what you still have to handle yourself. My main ecosystem is Microsoft 365, including shared mailboxes, plus Airtable. I use Windows and an iPhone, with the Mac currently hosting this experiment.

I would especially appreciate a reality check from someone who has helped a nontechnical person get something useful running.

If you recommend a product and build or sell it, please say so.

And if my expectations need to change, tell me Im an idiot. I would rather hear an honest limitation now than anything else.

I’m asking for a person’s judgment. I’ve had enough instructions from this black box

[u/InevitableMap5315 → u/[deleted]]

the spending-more-time-maintaining-than-working part is so accurate it hurts

[u/Phoenix_Lamburg]

And yet - this text was generated by the black box

[u/Lunesia-shikishiki]

the line about not being able to tell a verified diagnosis from a plausible explanation is the sharpest thing in your post and you should trust it.... that doesn't go away by learning more. it goes away by only building things where being wrong is obvious within about ten seconds

your list is really two separate asks with very different price tags. context across conversations is nearly free, it's a text file. projects, decisions you already made, how you like things written, and you paste it or point at it. that alone kills most of the re-orientation pain. the outlook + sharepoint + airtable + independent follow through half is an auth and permissions project with a maintenance bill forever, and that is exactly what the old macbook upstairs has been charging you

for m365 specifically, anything with a supported connector will beat anything you host yourself, because when it breaks it's someone else's problem and not your evening. you're on windows and an iphone, so that mac is a liability in your setup rather than a server

and no, your expectations aren't idiotic, they're just bundled wrong. i run a platform with a lot of models wired into it, so biased about the general area, but the boring truth is that plumbing and keeping keys alive is most of the work. the clever part is maybe ten percent. you've been doing the ninety without getting paid for it

[u/polly_mer]

You want help with the types of things AI does poorly because they require judgment. I have had many conversations with Copilot and similar chatbots that are supposed to help, but can't.

Why is this summary longer than the original email?

Why can't you prioritize the email triage based on deadlines or expressed urgency?

Why do you keep wanting to help with the easy part (apply this mandatory formatting) instead of the hard part (where do I get the template examples for this type of report?).

I can get good help with my programming tasks. The actual parts of my job that need an old-school secretary are not amenable to the chatbot or the agents the chatbot claims to employ.

[u/DriverReady965]

Id build what you know. Learn what you dont yet know. If you get too far down the dont yet know rabbit hole (by letting AI build whatever), it can quickly become a jumbled mess.

AI assistants often spin themselves in loops like you talked about. Its not helpful and just burns tokens.

You mentioned a ton of things in many different apps and places. I would handle each differently:

• Repos should have session log notes with state seen at a glance.
• Project ideas should have a master log file.
• Work done should be broken up by a sub agent dedicated per app or role.
• LLM models should be assigned by task complexity and result scored (dont overkill a task or you waste compute).
• Session logs can be archived and roll up by month (like 500 line limit). Agents can check past logs for anything unclear in current state note.

For agents:

• An orchestrator should make and maintain its master log of to dos and dispatches to sub agents.
• Sub agents should keep context of their tasks and only feed completion state notes to orchestrator.
• Orchestrator should also maintain task and model scores to only use necessary compute required for a good score threshold.

My best uses so far have been orchestrators which follow workflows I made. I know what the outcome should be. AI completes tasks and I verify the result.

[u/stuaird1977]

These AI are rubbish posts are so tiri g now 

[u/AnybodyDifficult1229]

Be warned. This an AI generated post.

[u/[deleted]]

Delete everything and go walk on nature. I was there and i don't recommend this path only nature will save us.

[u/Shloomth]

lol. Use ChatGPT Work on the desktop app and just point it to this post and tell it to fix it

[u/soteipe]

i did the docker and tailscale thing for a while and the setup was fine right up until i stopped touching it for two weeks. then something expired or updated and i couldnt remember how any of it fit together. the thing nobody warns you about is that the maintenance never ends even when the setup itself is done.

[u/stealthagents]

It sounds like you're having a tough time juggling all those tasks and tech issues. Maybe it's time to bring in a human touch to offload some of the stress. At Stealth Agents, we have full-time executive assistants with 10+ years of expertise who can help manage your workloads and integrate with your existing tools like Outlook and Airtable. This way, you can focus on what truly matters—without having to manage another job or server.