Curious to see how other technical founders here are managing the day-to-day operations of their software.
It is easy to spend all of our energy writing code or adjusting landing pages, but I have been spending time lately mapping out a strict "Operator's Field Manual" for my setup. Basically, I am documenting the exact, step-by-step procedures for things like deployments, system reboots, and server management so everything runs predictably without me having to guess under pressure.
For the solo developers and bootstrappers here:
Do you actually document your operational workflows, or are you just winging it until a server drops? If you do document it, what is your approach for keeping those procedures simple and actionable?
Would love to hear how you handle the practical side of keeping your systems running smoothly.

Depends which systems you're talking about. Any setup and config I do, I write very rough notes on the process. They are never right, never accurate, but serve as crib sheets. Found through experience there is very little point writing highly detailed step-by-step instructions because you can guarantee the next time you use them you'll be starting from a different position, or the software got an update and changed slightly.

In terms of your title "it works on my machine", never ever release anything until you've run it up on a full independent setup. For software build this is where VMs come in handy

Big +1 to Maher on rough crib sheets over perfect docs - detailed runbooks rot the moment the software updates.

Different angle though: the ops that quietly broke us weren't the servers, it was the finance side. Deployments fail loudly and you fix them. A missed VAT deadline, a payroll run you forgot while travelling, books that are three months behind when an investor asks for numbers - those fail silently and cost you at the worst possible moment.

So my "field manual" has a boring finance section: a fixed weekly 20-min cash check (what came in, what's due, what's runway), a payroll checklist with a confirmation-of-payee step so I don't fat-finger an account number, and categorising transactions as they land instead of a month-end panic. Same principle as your deploy docs - make the routine thing repeatable so it doesn't rely on you remembering under pressure.

What does everyone use to stop the finance ops drifting? That's the bit I still find hardest to make genuinely hands-off.

Sean makes a really good point about finance!

I nearly missed my corporation tax filing because I was so focused on customers. The irony is we obsess over uptime but forget HMRC has deadlines too. Fat-fingering an account number would be diabolical!

Now every recurring business task lives in my calendar with reminders:

• VAT

• Payroll

• Software renewals

• Insurance

• Domain renewals

• Annual accounts

Boring... but incredibly effective.

The calendar-with-reminders approach is exactly it, boring beats clever every time for this stuff. The corporation tax near-miss is scarily common, and I think it's because those deadlines don't chase you the way a customer or a bug does, right up until they do.

Only thing I'd add to your list: a recurring "money actually in vs out this month" check, separate from the deadline reminders. The reminders stop you getting fined, but the monthly look is what catches the slow surprises before they're a problem. Sounds like you've got it well dialled in though.