Is Day One worth paying for, or are there simpler alternatives?

Day One is a genuinely well-made journaling app, so this isn't a case against it, it's a question of fit. Whether it's worth paying for depends heavily on what you actually want from journaling.

What Day One does well

It's a polished, writing-focused journal: rich text formatting, media attachments, multiple journals, and a search experience built for people who write substantial entries and want to find them again later. If your journaling is closer to long-form writing, that depth is a genuine advantage over lighter apps.

Where the cost comes in

Day One's free Basic tier is limited, and its paid tiers (Silver and Gold, both billed annually) unlock the fuller feature set: more media, more journals, end-to-end encryption, and similar. For someone who writes daily and wants those extras, the subscription is reasonable for what it offers. For someone journaling casually, a few lines a night, the paid tiers may unlock more depth than they'll ever actually use.

What it doesn't do at all: scheduling

Day One is purely a journal. There's no calendar, no events, no reminders. If you're also juggling a separate calendar app, that's still two apps and two habits, exactly the setup that tends to make journaling the first thing to slip in a busy week, since it has nothing forcing you to remember it exists the way a calendar does.

When a simpler alternative makes more sense

If your journaling is a short daily habit rather than long-form writing, a few sentences on mood and gratitude, and you're specifically trying to make it stick rather than searching for maximum writing depth, a lighter app that combines journaling with your calendar can be a better fit, not because it's more powerful, but because attaching the habit to something you already check daily (your schedule) tends to survive longer than a standalone journal, however well built.

A fair way to decide

If you already know you want a serious, long-form journaling practice with rich formatting and don't mind a separate calendar app, Day One's subscription is a reasonable, well-earned cost. If you're mainly trying to build a short daily reflection habit and have struggled to keep a separate journal app open, it's worth trying an app that puts journaling next to your calendar before paying for depth you may not end up using.