I’ve been working on getting a clearer picture of the finances for each of my businesses. I do a fair amount by hand, in part because it helps prevent automation from making me complacent, and in part because Quickbooks Self-Employed is less than reliable. I’ve used it for years, and while it’s taught me a lot, I’ve definitely outgrown it. But even though I mostly just use it for invoicing, TurboTax, and helping estimate taxes, it’s an exercise in frustration. It deleted transactions I’d sorted for business once I started using a dedicated checking account and stopped using my personal acount (and so stopped having my personal account transactions be pulled in for review). Today, it wouldn’t show any but the latest invoice, and required multiple refreshes before they finally reappeared.
I use the more robust Quickbooks Online for my second business, and it’s been generally better, having none of the issues I just described above.
Basically, here’s the essential lessons learned: if you do any sort of freelance work, keep a separate checking account for it (even if you’re not a formally structured entity). Use it for all business-related needs. When considering options for accounting needs, consider reliability as much as you consider price.