Things 3 vs Guessly: Which Should You Choose in 2026?
Choosing between Things 3 and Guessly comes down to understanding what each tool does best. This comparison breaks down the key differences so you can make an informed decision based on your specific needs, not marketing claims.
Short on time? Here's the quick answer
We've tested both tools. Here's who should pick what:
Things 3
Award-winning task manager for Apple
Best for you if:
- • You want the higher-rated option (9.0/10 vs 7.6/10)
- • You need task management features specifically
- • GTD-based task manager for Apple ecosystem with elegant design and keyboard shortcuts.
- • Features projects, areas, tags, and seamless iCloud sync across Mac, iPhone, and iPad.
Guessly
Daily riddles for brain training and fun.
Best for you if:
- • You need something completely free
- • You need habit tracking features specifically
- • Offers daily riddles for brain training.
- • Focuses on cognitive skill improvement.
| At a Glance |  Things 3 |  Guessly |
|---|---|---|
Price | Paid | Free |
Best For | Task Management | Habit Tracking |
Rating | 90/100 | 76/100 |
| Feature | Things 3 | Guessly |
|---|---|---|
| Pricing Model | Paid | Free |
| Editorial Score | 90 | 76 |
| Community Rating | No ratings yet | No ratings yet |
| Total Reviews | 0 | 0 |
| Community Upvotes | 0 | 0 |
| Categories | Task ManagementTime Tracking | Habit TrackingFocus & Pomodoro |
Understanding the Differences
Both Things 3 and Guessly solve similar problems, but they approach them differently.Things 3 positions itself as "award-winning task manager for apple" while Guesslyfocuses on "daily riddles for brain training and fun.". These differences matter depending on what you're trying to accomplish.
When to Choose Things 3
Things 3 makes sense if you're looking for a comprehensive paid solution. With a score of 90/100, it's our top pick in this comparison.
When to Choose Guessly
Guessly is worth considering if you need a free tool.
Who Should Use What?
Bootstrapped or small team?
Guessly won't cost you anything to start, which is exactly what early-stage teams need.
We'd pick: Guessly
Growing fast?
Your team doubled last quarter and you need tools that won't break when you add 50 more people. Things 3 handles scale better in our testing.
We'd pick: Things 3
Enterprise with complex needs?
You need SSO, compliance certifications, and a support team that picks up the phone. Things 3 is built for organizations like yours.
We'd pick: Things 3
Still not sure? Answer these 3 questions
How much can you spend?
Zero budget? Guessly won't cost you anything.
Do you care what other users think?
Both have similar review counts. Read a few before you commit.
Expert opinion or crowd wisdom?
Our team rated Things 3 higher (90/100). But the community has upvoted Guessly more (0 votes). Pick your source of truth.
Key Takeaways
What Things 3 Does Better
- Higher overall score (90/100)
- Our recommendation for most use cases
Consider Guessly If
- You need a completely free solution
- Its specific features better match your workflow
- You prefer its interface or design approach
The Bottom Line
If we had to pick one, we'd go with Things 3 (90/100). But the honest answer is that "better" depends on your situation. Things 3 scores higher in our analysis, but Guessly might be the right choice if its specific strengths align with what you need most. Take advantage of free trials to test both before committing.
Frequently Asked Questions
Is Things 3 or Guessly better?
Based on our analysis, Things 3 scores higher with 90/100. Things 3 ispaid while Guessly is free. The best choice depends on your specific needs and budget. We recommend testing both with free trials if available.
Can I switch from Things 3 to Guessly easily?
Migration difficulty varies. Check if both tools support data export/import in compatible formats. Some tools offer migration assistance or have integration partners who can help with the transition.
Do Things 3 and Guessly offer free trials?
Most software in this category offers free trials or free tiers. Things 3 is paid with potential trial.Guessly is completely free. Visit their websites for current trial offers.