When I Die Files vs. StoryWorth: which is better for your family's legacy?

These two products get mentioned together a lot, but they're solving different problems. StoryWorth turns family stories into a printed book. When I Die Files is a comprehensive legacy platform that combines story writing, personal letters, and secure document storage.

There's real overlap in the storytelling department. But once you look past that, they diverge significantly. Here's an honest comparison.

What each product does

StoryWorth sends a weekly email prompt to someone you love -- a parent, a grandparent, yourself. Each week, they answer a question about their life. After a year, the answers get compiled into a hardcover book. The process itself becomes a weekly ritual of reflection, and the book becomes a family keepsake.

When I Die Files is built around the idea that your family needs more than stories. They need your practical information (passwords, insurance policies, account details), your personal messages (legacy letters to individual family members), and your stories -- all in one secure place. It uses guided prompts like StoryWorth, but the writing feeds into a larger system designed to be there when your family actually needs it.

Head-to-head comparison

Where StoryWorth wins

The book. This is StoryWorth's trump card, and it's a real one. A physical, hardcover book sitting on a shelf is something no digital platform can fully replicate. People flip through it. Kids pull it out on rainy afternoons. It sits on the coffee table and invites conversation. When I Die Files plans to offer printed options, but as of now, StoryWorth owns this.

The weekly ritual. The email-prompt cadence creates a structure that works for people who wouldn't otherwise sit down to write. Getting a question every Tuesday turns a daunting project into a manageable habit. There's something to be said for a product that does the nudging for you.

Gift simplicity. StoryWorth is easy to give as a gift. You buy a subscription for someone, and the prompts start arriving. The recipient doesn't need to set anything up or make decisions about what to write first. It's structured and low-friction.

Where When I Die Files wins

Comprehensive scope. StoryWorth captures stories. When I Die Files captures stories, legacy letters, practical documents, account information, and end-of-life wishes. If you're thinking about what your family will actually need when you're gone -- not just what would be nice to have on the shelf -- the scope matters.

Legacy letters. This is something StoryWorth doesn't do at all. A legacy letter is a personal message written for a specific person, often to be read after you're gone. A letter to your daughter for her wedding day. A letter to your spouse explaining what they meant to you. A letter to your best friend. These aren't stories for a book. They're private, intimate messages that need a different kind of delivery system. Our guide to legacy letters explains why they matter.

Secure document storage. Passwords, insurance policies, the location of the safe deposit box key, your financial advisor's contact information. StoryWorth doesn't touch any of this. When I Die Files uses end-to-end encryption to store the practical information your family will scramble to find. For more on this, see our guide to storing legacy documents securely.

Pricing model. StoryWorth costs $99 every year. If you stop paying, you keep your existing stories but lose access to new prompts and features. When I Die Files is a one-time purchase. Your vault and letters don't depend on a recurring subscription.

Self-paced writing. StoryWorth's weekly cadence is a strength for some people and a source of guilt for others. If you miss a few weeks, the unanswered prompts pile up. When I Die Files lets you write at your own pace, on your own schedule.

Pricing comparison

Who should choose which

Choose StoryWorth if:

• You want a printed book of family stories as a gift
• The weekly email prompt structure appeals to you
• You don't need document storage or legacy letters
• You're focused on capturing stories, not comprehensive planning

Choose When I Die Files if:

• You want stories, letters, and practical documents in one place
• Legacy letters to specific people matter to you
• You prefer a one-time purchase over annual subscriptions
• You're thinking about what your family will actually need, not just what's nice to have
• Security and encryption are important to you

Use both if:

• You want the StoryWorth book experience for the storytelling side
• You want When I Die Files for legacy letters, secure storage, and everything else

They're not really competitors. They're complements. StoryWorth gives your family a book to hold. When I Die Files gives your family everything else they'll need.

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When I Die Files is currently in pre-launch. Join the waitlist to be the first to know when we go live.

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