Sunsama was just named the best AI scheduling tool by The New York Times’ Wirecutter. I was tickled by the title since the word "AI" isn't even on our homepage!
It’s not that we’re anti-AI — I’ve been thinking about how AI fits into Sunsama more than ever in recent months. It’s just that there’s an unquestioned assumption that the solution to all of our problems is more AI, in more places, to do more stuff. I feel this pressure when I look at our competitors. Our biggest competitor spends millions blasting ads about their fully-automated AI scheduler that just tells you what to do. Our wisest investor strongly suggested we pivot to a fully-AI daily planner a couple years ago.
So after a rigorous review of all the products in the AI scheduling category, what does it mean that Wirecutter picked Sunsama (and it’s minimal AI)? I’ve been noodling on the irony and wanted to share my thoughts on how I see AI fitting into Sunsama and more broadly how we build a future where AI tools are a source of empowerment.
Great products give you a superpower
The Wirecutter review reminded me of something that gets lost in the hype cycles:
Great products are about the superpower they give you, not the technologies they use to give you those powers.
Reading the Wirecutter review helped me articulate the superpower we want everyone to have:
“Sunsama is a to-do list app that forces you to think through your daily tasks.”
I’ve been calling this superpower “forced thoughtfulness,” and AI is just one technology that might help us deliver it.
This is what we’re thinking about when we’re building new features in Sunsama. We don’t focus on helping you get more tasks done in a day, get more done in less time, or even get home on time. Those are nice side-effects (and we hope they do happen for you). Our end goal is to create software that makes it easy to be intentional about doing what’s important to you, and in a way that keeps you sane, healthy, and fulfilled.
Forcing thoughtfulness
Forcing thoughtfulness—real, sit-down-and-be-honest-with-yourself kind of thoughtfulness—is essential to fulfillment but we all struggle to do it.
To step outside of work for a moment: if my wife and I talk about weekend plans before the weekend starts—we tend to have a great one. We do things we care about. We feel less stressed and more fulfilled instead of spinning in indecision. I know this. And still, we don’t always do it. Because that conversation takes effort and time that slips through our hands like that toddler of mine who just ran out the front door.
It’s the same with Sunsama. Customers will write me saying: “my days feel so much better when I sit down and start my days in Sunsama. I know this but sometimes it feels too hard to sit down and plan”. In a perfect world, you’d get this superpower for free. But we live in an imperfect world and the effort you need to put in is why a whole market of products promising to schedule your day for you has cropped up. If it works, it’s a really nice promise. It sounds sexy and makes for great marketing too.
A couple years ago when our favorite investor pushed us to go full AI, we kicked the tires on the idea. We could not convince ourselves that an exclusively AI solution could do a good enough job. Until there’s an AI that’s a functional simulation of your entire consciousness, memory, personality, and preferences, the AI can’t be an arbiter of your intentions and what a good day feels like. But just because AI can’t do it all doesn’t mean it doesn’t have a place in making us a better version of ourselves.
The “dash of AI” we’d already added to our product has given us hope that there are ways to integrate AI that make being thoughtful feel more automatic.
How we sprinkle in AI
My favorite example of how AI can make you more thoughtful is Sunsama’s planned time prediction.
Before this feature existed, you’d need to manually type in a time estimate for each task. It’s just enough friction that users would routinely fill their work days with dozens of tasks with no time estimate. Without any time estimate, it’s easy to wildly over-estimate what you’ll get done in a day. Once we rolled out AI-planned time prediction, most tasks suddenly had realistic estimates—especially when the AI was wrong.
When the AI prediction is reasonable, you save time and effort during daily planning. But when it’s very wrong, something like this happens in the user’s mind:
“2 hours?!
No way. This takes way less than two hours…
Hm, more like 30 mins”
As soon as a user sees an unreasonable prediction an appropriate value comes to mind subconsciously. The obvious wrongness short-circuits the analytical and effortful “Type II” thinking that originally led to people leaving time estimates blank and get right to the intuitive “Type I” thinking.
The AI here isn’t telling you what to do, it’s simply prompting you to think more deeply than you could on your own. The AI can look across all of the tasks I’ve ever entered in Sunsama in milliseconds and makes a data-driven suggestion. That’s not something my brain can do. The way we surface, expose, and interact with the AI’s output is what decides whether the technology empowers us or diminishes our agency. And as product designers, it’s our job to be imaginative and creative enough to build AI features that augment you instead of replace you.
Looking ahead
Seeing an incorrect suggestion by our planned time AI turn into a net-positive for a user reframed how I thought about AI usefulness. I stopped thinking of AI features as a way to complete work accurately for a user and instead as the first move in a conversation—a proposal that nudges the user to share what they think, feel, or know. The kind of thing that might have felt onerous to consider if the AI hadn’t made the first move.
To start the year, my product imagination has been fixated on one conversation we have with ourselves that can feel too daunting to fully think through:
As soon as we wake up, our gears start churning about what we should do that day. But turning those half-formed, not-yet-articulated thoughts into something actionable and clear feels hard. I think of it as a kind of writer’s block—whether we’re planning our day in a notebook, calendar, or Sunsama.
To tackle that, we’ve been building a highly experimental Voice AI that can update your Sunsama while you’re walking or driving. But the real magic is how conversation makes me more thoughtful about my day than when I’m staring at a task list. Talking out loud, even with an AI, helps me turn that jumble of thoughts in my head into something actionable—faster, and with less effort—than simply writing it down. Shooting the breeze with the AI short-circuits that high-effort, analytic thinking I’m not ready for first thing in the morning. Because talking is so easy, I ferret out things I was too avoidant to write down when planning my day inside the app.
That’s what conversation allows and what good AI could support: making clarity feel easy to reach, not hard-earned and rigorous. After my chat, I’ve got a thoughtful and complete plan that required less effort and didn’t demand more clarity than I had to begin with.
In a perfect world, you’d put in zero effort and wake up each morning with a list that accurately reflects your intentions. Until that’s possible, we’ll keep building ways to help you get to a daily plan that reflects your intentions with less effort (real or perceived). And yes, we’ll probably use AI to do that, but only if it serves you and supercharges your ability to live and work thoughtfully.
If we, product designers and technologists, can build AI experiences that make it easier and faster to think and express our intentions, then we don’t need to fear AI. Because as it becomes more capable, so do we.
