In 2019, How Can We Make a Better Calendar?

Zi Wang
The Startup
Published in
7 min readDec 17, 2018

How common is it to hear, there’s just not enough hours in the day?

At the tail end of 2018, like many other people from around the world (Mike Arnold), our team is radically reimagining a calendar for the future.

We started by looking at the main tool for organizing our time, the calendar, and the internal math involved with figuring out why some events in our lives are more valuable than others. For instance. The act of physically marking a future event on a chart indicates that it is important enough for us to remember in the future.

Calendars tell the world of events that shape our lives, providing us with personal meaning.

Just as a map paints a picture of where we have been, a calendar tells a story on how we spend our time, who we interact with, and what we want to do. Yet like a map 20 years ago, a calendar is purely informational. It guides us through the complexity of life without giving us better ways of accomplishing the same goals.

Similarly, most of the methods currently deployed by work scheduling tools are built on traditional calendar formats, created during the height of the manufacturing era on delivering the most efficient factory workers. But we are not cogs in a machine. We cannot just be turned off or on for short-term variate forecasting, nor are we perfectly exchangeable with the next person in line.

Take this example: you have a flight to take tonight. By marking in our calendar that we have to be at the airport in 3 hours, do we really want to be reminded every 30 minutes that if we don’t leave we will miss our flight?

What if the calendar could contextually understand that we have to physically be at the airport, and to physically be at the airport we need a ride? Why can’t a calendar understand that need, and help provide solutions rather than just regurgitating our problems?

This has been our singular focus for the past several months as we look to unlock the Calendar as a Platform.

Here is a Big idea — A Calendar that gets things done! Can we create a tool that not only organizes your life — but actively finds services that help us with optimal schedules?

While we do have different variations of calendars for different circumstances in our lives — the typical Gantt chart calendar for work, the to-do list for organizing our personal lives, or the chore list to keep our home in order — they all fail to do one thing. The same thing that maps failed to do before platforms like Uber came along (Garrett Camp); instead of trying to show how to get you from point A to point B, what if we did it for you? Instead of organizing which order you should complete tasks, what if a calendar created a marketplace to outsource the work for you?

Unfortunately, no such platform currently exists. This is the reason why very few people find additional utility beyond just keeping track of work schedules. Calendars are static in the information they show and offer no connection to the outside world. If we schedule a task reminding us to clean our home, but we decide it would be easier to hire someone, we have to search for outside platforms and vendors, not achieving the ultimate goal of what a calendar could be.

Many have argued this is the reason that product searches on Google have been steadily decreasing, while Amazon has had great success (Mitch Joel). People no longer want to just have a storage of information, but the full spectrum of intent, order fulfillment, and payment.

This is the kind of marketplace Timeless is trying to create: a service matching platform that addresses the holy trinity of product desire — price, selection, and availability coined by John Rossman.

Let us explain. As we have proven in our technical paper, we can optimize the intensity and time-period of tasks being completed, as well as how to value one’s time to create a marketplace for it. While products and certain services such as driving have reached the late stage in market adoption and price commoditization, there are still vast areas of life utility that remain untouched and will for some time. It’s why, according to Andrew Chen, that service marketplace is the next frontier.

In utilizing the calendar as a platform, we can properly actuate the exchange of services in a marketplace. We are not focused on comparison shopping, nor showing countless ads for services until you give in and buy one. Each is predictively matched based on your needs on time, price, and urgency of fulfillment, with the sole intention of limiting your decision headache to a simple binary choice (Nir Eyal). By wholly understanding the problem you are tackling and matching it with the professional services you truly need, the result will hopefully be minimizing the uncertainty associated with purchasing a service today — much like Amazon’s success in creating a product-matching platform.

Not everything we enter into a calendar has a task to be outsourced, just as we do not need to get a delivery sent to every location we search on a map. This is where the fundamentals of comparative advantage become the cornerstone of our market.

In this context, there are two main tranches of comparative advantage services people search for, outsourcing (tranche one) and do-it-yourself (tranche two), with tranche two increasingly more subjective and non-binary. In terms of your personal time, it translates to: does it cost more to hire someone to complete a task, or to do it yourself?

We thus define ”outsourcing” in this context, to be any service where you could theoretically do it yourself, but you either do not have the legal qualifications or find the task worth your time. This can range from hiring a fitness trainer, going to the doctor, or performing home services. DIY is an area where the task itself cannot be outsourced, but you need to expedite the process to complete it. Common DIY services are QA forums, Ask Me Anythings, or schooling systems, where the task itself is learning a new library for a programming language, or learning to play the cello.

We have chosen to focus on tranche one (outsourcing), as we believe the objectivity of service completion will better suit a first generation calendar platform that will have limited information. The outsourcing service economy is a $90 billion industry, and we aim to tackle it by targeting the tech workers and traveling urbanites (folks like Christopher Fong, Bill Tai, Mark Bergen …).

There are many on-demand services we have gotten used to being at the forefront of innovation: food delivery, cleaning services, and transportation methods, that all help us live easier lives. However, these services all exist on separate platforms and require us to input our needs manually.

Having the calendar as the all-encompassing platform for our marketplace also allows us to create unique business models, avoiding the pitfalls of ad-based and transaction fee revenue models.

Uber, GrubHub, Instagram, and Mailchimp all took existing products and turned them into lucrative marketplaces to directly solve a need. For us, we start with the essential utility of the calendar, a well-understood time management tool to make our lives easier. Creating the Calendar as a Platform is how we aim to enhance/improve the tool and make calendars great again 😜

If you want to build a ship, don’t drum up people to collect wood and don’t assign them tasks and work, but rather teach them to long for the endless immensity of the sea.

— Antoine de Saint-Exupery

While many promises on the future of service economy are still being developed, we have set out to change the world — a challenge that is not possible to do alone. Our mission is matching people’s time with helpful services, and we need everyone to help us on the long journey ahead.

We are hiring UX designers & ML SWEs — z@timeless.space

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