I self-host most of the software in my life — mail-adjacent tooling, dashboards, documents, automation, backups. People assume it's an anti-SaaS stance. It isn't. SaaS is often the right call, especially for a business that shouldn't be paying an engineer to babysit a mail server. My reasons are narrower and more personal: ownership is a slow, compounding advantage, and I would rather pay in hours than in data.
The compounding part
Every service I run teaches me something that transfers. Debugging why a reverse proxy mangles a header, tuning Postgres so a dashboard stops timing out, recovering from a backup I was smart enough to test — those hours aren't overhead, they're the exact skills I get paid for in consulting. Self-hosting is a gym membership that happens to also run my infrastructure.
The data part
When a service is free, the arrangement is usually that you're the product. When it's paid, you're a tenant who can be repriced, deprecated, or acquired out from under your workflow. Self-hosting doesn't make me immune to any of that, but it moves the switching cost to my side of the table. My data lives in formats I can read, on disks I control, with an export path I've actually exercised.
Convenience is renting. Ownership is a mortgage. Both are valid — but know which one you're signing.
Where I don't self-host
I'm not a zealot. I don't run my own email delivery — deliverability is a full-time adversarial game against spam filters, and I'd lose. I don't self-host anything where an outage would hurt someone who didn't sign up for my hobby. And for clients, I recommend managed services constantly, because the honest cost of self-hosting is the 2 a.m. page and the succession problem when the one person who understands it leaves.
The rule I actually use
Self-host the things where learning is the point or ownership is the point. Rent the things where reliability is someone's full-time job and should stay that way. Draw that line deliberately, revisit it yearly, and never let "because I can" masquerade as "because I should."