November 30, 2022

Taking Control of Your Schedule So It Doesn’t Take Control of You

Jeremy Bell
Jeremy Bell
Founder & CEO

One of the byproducts of building a software company focused on productivity is that we spend a lot of time thinking about better ways to optimize our time. This is especially important for us because, as a remote-first startup that also runs a 4-day work week, we greatly appreciate the value of time.  If we’re going to be successful, we have to be intentional about what we choose to spend our time on… and what we choose not to.

As we've been building Mayday, we’ve explored many ways to help people take control of their schedules. And with those learnings, we’ve oriented our product around four areas that help our team be more effective every week.

Schedule Everything

If you intend to spend time on something, schedule it. Personal stuff, work stuff, meetings or tasks; If you think it’s a priority and requires your time, it needs to go into your calendar. All of it.

Scheduling everything in your calendar gives you a better sense of your true availability and forces you to think about what’s important. If something isn’t a priority, ask yourself if it needs to happen at all. If it requires other people, ask yourself if it can be done asynchronously instead of as a meeting. If someone asks for your time, determine if the request is truly important. If it's not, it's okay to say no because you've likely already underestimated the time required to complete everything else that needs your attention.

The goal is to make time for urgent and important things while deferring (or eliminating) everything else. We call this Schedule/Priority Fit. Whatever your priorities are, you can only accomplish them if you invest time into them. So your schedule needs to reflect that.

Some people argue that success is when your calendar is empty. Nonsense. Retirement is when your calendar is empty. In the meantime, your calendar needs to be filled with your priorities. So plan accordingly.

Context-Switching Destroys Days

Context-switching is a term that originally comes from computer science — it’s when a CPU changes from one process to another. The state of the first process needs to be restored and resumed at some later point, resulting in a loss of efficiency in execution.

Our brains work in the same way. There’s a cognitive cost to alternating between tasks, and the ways we work—tracking multiple threads, notifications, tabs—all serve to increase the amount of context-switching we experience on a daily basis. And a poorly organized schedule can be just as damaging.

You can lose up to 50% of your productivity as a result of context-switching because it takes time for your brain to regain focus once interrupted. And frequent context-switching leads to additional cognitive fatigue, which further reduces productivity. I'm particularly susceptible to this myself and can easily lose hours as a result of a single errant distraction if I’m not diligent.

One of the best methods of reducing context-switching is to batch similar things together. Organize your time around themes (e.g. focus time, writing, email, coding, designing, team sync, etc.), and aim to carve out meaningful spans of time to focus on the task in front of you, followed by a brief break. By one assessment, the ideal work-to-break ratio is 52 minutes of focus, followed by 17 minutes of rest.

I often find switching between meetings to be less disruptive than tasks, so cluster your meetings together to preserve longer stretches of uninterrupted focus time. If possible, go a step further and try to organize specific days around a particular theme or focus (eg. "Meeting Mondays," "Team Tuesdays," "Focus Fridays," etc).

Protect Your Time

The key to taking control of your schedule is prioritizing your tasks in advance and then blocking time in your day so you can complete them. "Time blocking" involves dividing your day into distinct blocks of time, with each block dedicated to completing an individual or group of tasks.

This is beneficial because it allows you to focus on specific tasks by setting aside time for them instead of just having an open-ended to-do list. It's also the most effective way of ensuring your schedule reflects your priorities.

Cal Newport, author of Deep Work, dedicates upwards of 20 minutes every evening blocking time for the following work day:

Sometimes people ask why I bother with such a detailed level of planning. My answer is simple: it generates a massive amount of productivity. A 40 hour time-blocked work week, I estimate, produces the same amount of output as a 60+ hour work week pursued without structure.

This technique is simple but impactful because it helps you enter a focused state of (you guessed it) "deep work," which Newport describes as "a state of peak concentration where you can learn difficult things and create high-quality work quickly."

It also helps you be more intentional with your time and prevents your coworkers from taking too much as well. Because that's what is going to happen if you don't take that time for yourself. Someone else is going to take it from you.

However, therein lays the challenge of time blocking in a typical workplace. If you block your entire schedule for all your priorities, you’ll never be available to meet with others. But if you keep yourself open for potential meetings, you’ll inevitably end up overbooked without enough time to get stuff done.

The biggest misconception with time blocking is that you have to rigidly stick to the schedule no matter what. According to Newport, it's important to be flexible and adjust your time blocks as your priorities evolve. No matter what happens during the day, "the goal is to make sure you always have an intentional plan for the time that remains in the workday."

With shifting priorities, opportunities, and unforeseen changes, it's inevitable that something will affect your original plans. We all need to be comfortable with our schedules changing to remain agile and effective. Or as Mike Tyson said, "everyone has a plan until they get punched in the mouth." Start with a plan but expect to be punched.

Automate It

If everything above sounds daunting, it's because it is. Most people struggle to implement these techniques into their daily lives because they require a lot of effort to set up and maintain.

Regularly achieving Schedule/Priority Fit can be challenging when you work alone, but it becomes exponentially more difficult when you need to collaborate with others. What works for you may not work for others, and the more your team has time-blocked their week, the less time there is available for everyone to meet. So everyone understandably prioritizes their own needs and schedules things in whatever way works best for them. And that’s how your team ends up with overbooked and fragmented weeks that inhibit deep work.

The typical solution is to hire an executive assistant. One that can evaluate everyones' individual schedule and priorities and then make an informed decision about what is most important and what can be moved to accommodate the group. Most people don’t have this luxury.

This is where Mayday comes in.

We're building an AI scheduling assistant to solve this exact problem. Mayday is a new kind of time management tool that replaces your calendar with something smarter. It can evaluate a variety of data points across everyone's schedule to determine the ideal time to schedule something. Instead of just looking for empty spaces in everyone’s schedule, our “Ideal Scheduling Engine” finds the best times by weighing the urgency and importance of what you’re trying to schedule against what’s already in everyone’s calendar.

Mayday’s Scheduling Links leverage this understanding of everyone's ideal time and gently nudge guests to pick a time that works best for everyone, instead of just blindly offering up every available time slot that inevitably forces you to context-switch.

Calendar Shield is a feature that protects your time by automating time-blocking. It protects your schedule before you end up in too many meetings, automatically schedules buffer time before important meetings, and sync events between calendars (so that dentist appt in your personal calendar is also protected in your work calendar).

We’ll soon be launching Tasks in Mayday as well, which will automatically block times in your calendar for your to-do’s. But when your priorities inevitably shift, it will intelligently reschedule those tasks so you won't need to manually manage your blocked time anymore.

Our goal with Mayday, as both a business and with the software that we’re building, is to help everyone be more intentional with their time so they can get the most out of every day. If you have other techniques that you find work well for managing your time, let us know on Twitter.

And if you’re interested in what we’re building, sign up for early access: