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Productivity · head to head

Day One vs HEY

Day One logo

Day One

Productivity

Journalling app for iOS, Android and Mac now sold as a subscription after years as a one-time purchase

From
Free
Rated
-
Full reviewWebsite
HEY logo

HEY

Productivity

Flat annual subscription email service from 37signals, with its own hey.com domain and a distinctive Screener

From
$99/year
Rated
-
Full reviewWebsite

The short version

  • Only Day One has a free tier, so it costs nothing to try first.
  • Each has a real cost: Day One it moved from a one-time purchase to a subscription after the Automattic acquisition, so long-term cost is materially higher than the original pricing implied.; HEY there is no free tier and no monthly billing option, so trying it beyond the trial means committing to a full year upfront.
  • They diverge on capability: Day One covers Multiple journals, HEY covers The Screener.
  • Prices and features above were last checked on 1 September 2026.

Where they differ

Only the attributes on which Day One and HEY actually diverge.

Attributes where Day One and HEY differ
AttributeDay OneHEY
Starting priceFree$99/year
Pricing modelFree tier plus subscriptionPer user per month
Free tierYesNo
PlatformsiOS, Android, macOS, WebMac, Windows, Web, iOS, Android

Identical on both: user rating (Not yet rated), category (Productivity).

What each one covers

Drawn from each product's published feature list. An absence here means we hold no record of it - not that the product lacks it.

Only in Day One

  • Multiple journals
  • Rich entries
  • End-to-end encryption
  • On This Day
  • Cross-platform sync
  • PDF and Day One export

Only in HEY

  • The Screener
  • Imbox, Feed and Paper Trail
  • Reply Later stack
  • Focus and Reply mode
  • Screen sharing style clips
  • No tracking pixels

What people use each for

The jobs each tool is most often brought in to do.

Day One

  • Someone wanting a private daily journal with photos that syncs between phone and laptopnot HEY
  • A person keeping a travel journal that auto-attaches location and weather to each entrynot HEY
  • Someone who wants encrypted entries kept separate from an unencrypted general journalnot HEY
  • A user who wants automated daily writing prompts and On This Day nostalgia reviewnot HEY

HEY

  • Someone who wants to replace Gmail or iCloud Mail entirely with an email service built around approving senders before they reach the inboxnot Day One
  • A user overwhelmed by newsletters and receipts who wants them automatically separated from person to person conversationnot Day One
  • A family that wants shared but individually addressed email under one annual plannot Day One
  • A small company wanting HEY for Work on its own domain with the Screener model for the whole teamnot Day One

Where each one falls short

Documented limitations, not opinions. Every one is a constraint you would hit in normal use.

Day One

  • It moved from a one-time purchase to a subscription after the Automattic acquisition, so long-term cost is materially higher than the original pricing implied.
  • The free tier caps at one journal and 25 photo entries, which is restrictive enough that anyone journalling seriously for more than a few weeks needs to pay.
  • End-to-end encryption is opt-in per journal rather than on by default, so users have to actively choose it and understand which journals are protected.
  • Cancelling Premium after using multiple journals or heavy photo storage can leave content viewable but with sync and some features disabled, so people should export before cancelling.
  • As an Automattic product, its roadmap sits behind a company whose primary focus is WordPress and Tumblr, not journalling specifically.

HEY

  • There is no free tier and no monthly billing option, so trying it beyond the trial means committing to a full year upfront.
  • Adopting HEY means changing your actual email address, not just installing a new client, which is a bigger migration than switching apps on an existing address.
  • The Screener and categorisation model is a real departure from a standard inbox, and some users take time to adjust or find it gets in the way for high volume mail.
  • Short vanity addresses carry steep additional annual fees, up to 999 US dollars a year for a two character address.
  • It does not connect to or manage existing Gmail, Outlook or iCloud accounts, so it cannot be used as a general client the way Mimestream or Apple Mail can.

Pricing, plan by plan

Day One

Free
  • FreeFree
    • One journal
    • Up to 25 photo entries
    • Basic sync
  • Day One Premium$3.99/month
    • Unlimited journals and photos
    • End-to-end encryption
    • On This Day and audio transcription
  • Day One Premium Annual$34.99/year
    • Same as monthly Premium at a lower effective rate

HEY

$99/year
  • HEY for You$99/year
    • One hey.com email address
    • Screener, Imbox, Feed and Paper Trail
    • Billed annually only, no monthly option
  • HEY for Families$179/year
    • Covers up to five family members
    • Same features as HEY for You per member
  • HEY for Work$12/month
    • Per user, for organisations on a company domain
    • Admin controls for a team

Which should you pick?

Choose Day One if

  • You need multiple journals.
  • You want to start without paying.
  • You work on iOS, Android, macOS, Web.
  • You also want rich entries.
Day One review

Choose HEY if

  • You need the screener.
  • You work on Mac, Windows, Web, iOS, Android.
  • You also want imbox, feed and paper trail.
HEY review

Questions people ask

Is Day One or HEY better?
Neither clearly leads. Day One starts at Free and HEY at $99/year, and user ratings are close enough to be indistinguishable. Choose on capability and platform support.
Which is cheaper, Day One or HEY?
Day One has a free tier; the other does not. Paid plans start at Free for Day One and $99/year for HEY.
Does Day One or HEY run on more platforms?
Day One runs on iOS, Android, macOS, Web. HEY runs on Mac, Windows, Web, iOS, Android.
Can I use Day One for free?
Yes. Day One has a free tier, so you can try it without paying. HEY starts at $99/year.
What is Day One best used for?
Day One is most often used for someone wanting a private daily journal with photos that syncs between phone and laptop, a person keeping a travel journal that auto-attaches location and weather to each entry, someone who wants encrypted entries kept separate from an unencrypted general journal, a user who wants automated daily writing prompts and on this day nostalgia review. Of those, someone wanting a private daily journal with photos that syncs between phone and laptop and a person keeping a travel journal that auto-attaches location and weather to each entry are not what HEY is typically brought in for.
What can Day One do that HEY cannot?
Day One covers Multiple journals, Rich entries, End-to-end encryption, On This Day. HEY covers The Screener, Imbox, Feed and Paper Trail, Reply Later stack, Focus and Reply mode.

Answered from the vendors’ own pages

Day One: Is Day One still a one-time purchase?

No. Since the 2021 Automattic acquisition it is sold as Day One Premium, a subscription. Older lifetime purchasers were grandfathered but new users pay a subscription.

HEY: Can I use HEY with my existing Gmail address?

No. HEY provides its own hey.com email address; it is not a client layered over an existing Gmail or other account.

Day One: Is encryption on by default?

No, end-to-end encryption is an option users turn on per journal, not a default for all entries.

HEY: Is there a free plan?

No. HEY offers a trial but bills annually only, with no free tier and no month to month option for individuals.

Day One: Can I export my entries if I cancel?

Yes, PDF and native Day One export formats are available regardless of subscription status, though some sync and premium features stop working.

HEY: What is the Screener?

A feature that holds mail from any new sender until the user explicitly approves them, before it appears in the inbox at all.

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