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Productivity · head to head

Day One vs DeskTime

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
DeskTime logo

DeskTime

Productivity

Automatic computer activity tracking and productivity analytics

From
Free
Rated
-
Full reviewWebsite

The short version

  • 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.; DeskTime screenshots are excluded from the Pro plan and start at Premium
  • They diverge on capability: Day One covers Multiple journals, DeskTime covers Automatic activity tracking.
  • Prices and features above were last checked on 1 September 2026.

Where they differ

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

Attributes where Day One and DeskTime differ
AttributeDay OneDeskTime
Pricing modelFree tier plus subscriptionfreemium
PlatformsiOS, Android, macOS, WebWeb, IOS, Android, MacOS, Windows, Linux
FoundedUnknown2013

Identical on both: starting price (Free), free tier (Yes), 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 DeskTime

  • Automatic activity tracking
  • Application and website tracking
  • Daily reports
  • Weekly summaries
  • Privacy-first design
  • Detailed analytics
  • Goal setting
  • Mobile apps

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 DeskTime
  • A person keeping a travel journal that auto-attaches location and weather to each entrynot DeskTime
  • Someone who wants encrypted entries kept separate from an unencrypted general journalnot DeskTime
  • A user who wants automated daily writing prompts and On This Day nostalgia reviewnot DeskTime

DeskTime

  • Automatic time tracking of desktop app and website usagenot Day One
  • Measuring team productivity and idle timenot Day One
  • Scheduling shifts and tracking absencesnot 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.

DeskTime

  • Screenshots are excluded from the Pro plan and start at Premium
  • Integrations and API access require the Premium plan
  • Shift scheduling requires the Premium plan
  • Enterprise is aimed at 200+ users and is priced by quote with no published rate
  • The advertised $6.42 and $9.17 per user rates require annual billing; monthly billing costs more
  • The trial lasts 14 days

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

DeskTime

Free
  • FreeFree
    • Activity tracking
    • Basic reports
    • Weekly emails
  • Pro$9/month
    • Everything in Free
    • Advanced reports
    • Detailed analytics

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 DeskTime if

  • You need automatic activity tracking.
  • You want to start without paying.
  • You work on Web, IOS, Android, MacOS, Windows, Linux.
  • You also want application and website tracking.
DeskTime review

Questions people ask

Is Day One or DeskTime better?
Neither clearly leads. Day One starts at Free and DeskTime at Free, and user ratings are close enough to be indistinguishable. Choose on capability and platform support.
Which is cheaper, Day One or DeskTime?
Day One starts at Free and DeskTime at Free.
Does Day One or DeskTime run on more platforms?
Day One runs on iOS, Android, macOS, Web. DeskTime runs on Web, IOS, Android, MacOS, Windows, Linux.
Can I use Day One for free?
Both have a free tier, so you can try either at no cost before committing.
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 DeskTime is typically brought in for.
What can Day One do that DeskTime cannot?
Day One covers Multiple journals, Rich entries, End-to-end encryption, On This Day. DeskTime covers Automatic activity tracking, Application and website tracking, Daily reports, Weekly summaries.

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.

DeskTime: What are DeskTime's subscription tiers?

DeskTime offers Pro at $6.42/user/month (annual billing) for small teams and startups, Premium at $9.17/user/month (marked Most Popular) for hybrid and growing teams, and Enterprise with custom pricing for 200+ users.

Source
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.

DeskTime: What features differentiate the Premium tier from Pro?

Premium adds screenshots, integrations & API, and shift scheduling compared to Pro's document title tracking and calendar integrations.

Source
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.

DeskTime: How long is the DeskTime free trial?

DeskTime offers a 14-day free trial. No credit card is required to start.

Source
DeskTime: What billing options does DeskTime offer?

DeskTime offers monthly or annual billing. Annual subscriptions include one complimentary month compared to monthly plan pricing. You can pay by credit card or PayPal.

Source
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