How do you manage your business workload? Launching and running a business can be overwhelming.

Here is how one founder effectively manages his startup workload. He originally shard this with the reddit startup community.

Being an entrepreneur is first, and foremost, about taking control of your time. With no boss to dictate your schedule, it’s on you to manage your days effectively. It’s easy to stay busy, but harder to stay busy with the right mix of stuff, balancing revenue-driving work with growth.

I was tired of each day being a flurry of todo’s bouncing around in my head. I was also mortified at the days when I stumbled across large pockets of free time, and dicked around on the internet instead of using that precious time constructively.

Enter the scheduling system. I’ve been using this method for the last few months, and it has rocked my world. I’m getting more stuff done, and more importantly, planning for free time and using it constructively. The best part is that it’s very simple.

Scheduling the day: A time management method for entrepreneurs.

Until recently, I didn’t have a productivity system. I didn’t really need one – there was always work that needed doing, and I had various side projects to fill out the time. I was always pretty comfortable flowing from one task to another.

But, letting my tasklist run the day had downsides. Work expanded to fill the amount of time I had, meaning that I could increase my free time without increasing productivity. Also, those side projects I pursued in my vanishing free time weren’t going anywhere.

My tasklist dictated my time, but in a haphazard, thoughtless way. When I had something in front of me – especially with a deadline – I attacked it. But I lacked direction when there was no urgent problem to solve. I was great at bottoms-up execution, but not so great at top-down management.

Then I returned to consulting, and with it, multiple clients, complex projects and numerous deliverables, I also renewed my commitment to making serious progress on side projects. The “flow” wouldn’t do. I needed a system.


The scheduling system is basically a fusion of tasklist, project tracker and calendar into one entity. Every night, I review outstanding Tasks and ongoing Projects, and I schedule them to available timeslots. Completed tasks are checked off and disappear; those that get missed are rescheduled at the next planning session. I try and fill in the entire day with appointments, even if they’re just “go for a walk” or “travel to client.”

It works because scheduled things get done. The scheduling discipline has increased the number of tasks I complete each day and helped me make meaningful, sustained progress on larger projects. I’m much better at prioritizing, because the discipline brings my tasklist to bear against the reality of limited working hours.

The scheduling discipline equips me with a plan for using my time well. It’s like eating healthy. If you “try to eat healthier” from whatever’s in front of you, you won’t do as well as someone who commits to a diet through grocery shopping and meal prep. One is aspiration, the other is a plan.

The scheduling discipline works even when I don’t follow the actual schedule, which is nearly 100% of the time. Scheduling merely sets the goalpost. Going off track doesn’t change the fact that I’ve prioritize what I need to do and committed to do it, which is the real struggle.

Here’s how I do it.


Note – this is obviously for a mac setup. I’m sure you can find analogs for PC/Android, I just don’t know what they are.

  • Fantastical 2, desktop and iPhone apps. The OS X Calendar on steroids. Has a lot of nice features, but the most critical is that it represents your Reminders on a calendar.
  • iPhone with Siri and Reminders. My system works only if it’s super-easy to enter new appointments and reminders.
  • iCloud account (for easy syncing between everything).

The Process

  1. Throughout the day, I save new tasks as Reminders with a tentative timeframe attached. I usually dictate into my phone or type it into Fantastical 2 (“Remind me to call the dentist tomorrow morning”). I always schedule tasks for a general time like “tomorrow afternoon” or “Friday morning”. It gets moved to the right time in the nightly scheduling.
  2. Each night, I review and schedule tasks. This 10-15 minute ritual is the last thing I do in the work day. First, I pull up the calendar in Fantastical, and drag all my unchecked Reminders to open slots. Simple stuff like phone calls and quick emails can all go into the same slot, to be handled in sequence, while a longer project will get its own slot.
  3. In that same nightly review, I schedule the day’s activities. I use one primary account (iCloud calendar) and put blocks down for projects, workouts, transit time, prep time for appointments, phone calls, meditation, meals and whatever else I want to accomplish.
  4. During the day, I stick to the calendar when possible. I have it running constantly and try to address tasks and project work in the time its scheduled for.
  5. But I don’t worry if the schedule gets blown up. Sometimes I get taken off track by something important. Other days, I’m not nearly as enthusiastic about the work I committed to, and I blow it off to get a massage or play Insurgency. It’s like eating pizza after a hard training session; discipline earns you guilt-free slacking. That night, I honestly account for what I did and didn’t do, and push things back accordingly.

The Benefits

  • Doing all the planning in one session reduces mental strain. An unstructured task list makes your brain work every time you look at it. Prioritizing tasks, estimating time/labor and thinking about when to do each item. Batching the planning conserves mental calories for the actual work. Better follow-through on tasks. Scheduling things improves the chance they’ll get done, period – even if I don’t actually do them on the schedule. It seems nutty to schedule meditation, for instance, but I always seem to find time for it when I schedule it in.
  • Free time is anticipated and used. I used to stumble over pockets of free time, and when I found them, I didn’t know what to do with myself. Now, I fill wide-open spaces with productive uses of energy.
  • Planning around my natural energy levels. I can block out time for big projects in the morning, schedule email replies after lunch, and generally anticipate what I’ll be best at.
  • Better prepped and more polished. Scheduling time to prep for meetings ensures that I walk into those meetings with the right documents, talking points and questions. Even five minutes can mean the difference between a great meeting and a poor one.

Important Caveats

  • This is not about being a robot. The schedule is a guide, not strict; I prepare it as though I’ll stick to it, but I rarely stay 50% on track. Think of it this way: My natural productivity is about a C+. With this system, I plan for an A+, and in executing wind up around a B/B+.
  • This is not about “Manager’s schedule”. My schedule includes huge blocks of time for writing sessions and other creative projects. The only parts of the day with micro managed tasks are usually after lunch and the afternoon.
  • This is not about squeezing productivity from every second of the day. I actually relax more now, because my improved productivity opens up more time for long walks, cooking dinner and all the other things that make life fun. I generally schedule only between 8am and 4pm, and leave weekends completely clear.