The Joys of Scheduling.

Since I first became a leader of an organization six years ago, I’ve seen my number of responsibilities grow tenfold. I’ve got to constantly shift my focus from Sales, to Finance, to Operations, to Human Resources, all while trying to establish and maintain a healthy company culture.

This quote seems apt to describe my feelings:

You jump off a cliff and you assemble an airplane on the way down.

Reid Hoffman

This reached a high point for me in months two and three of starting Mäd, where I didn’t manage to read a single book. This was, for me, highly unusual. I’m an avid reader (check out my Reading List), and I must have read a hundred books that year, but I didn’t manage to get a single reading session in for those two months.

I felt like I was constantly putting fires out and rushing to meet deadlines and perceived emergencies.

Looking back on this time, I now realize that if I had been lazier, things would have pretty much turned out the way they have now. The company is healthy and growing, and I’m no longer working 16-hour days.

So, you might ask yourself, what changed?

First, I stepped out of the office for two whole weeks, which gave me a fresh perspective, and I also started to schedule my weeks instead of just working against a long list of todos.

I’ve written about this topic before in my short thoughts, and today I felt it was now a topic worth covering with a longer, more in-depth treatment.

To summarize the issue, I’ll arrogantly quote myself as usual:

Because they (todo lists) are so easy to create, one ends up taking way too much on board, and then either over working, or doing things faster and sacrificing quality. The better approach is to schedule things on your calendar. It’s a reality of life that we have a limited amount of time available, both during the working week and also in life in general.

I am now a full-on convert to scheduling, and in this essay, I hope to open your eyes to the joys of scheduling time, and how it can actually give you more time to do the things you love.

The issue is that scheduling has a bad rapt because our first interactions with scheduling during our education are not so positive. There are two main problems with the way we are introduced to scheduling:

  • Firstly, you probably didn’t (or don’t, if you are still in education), enjoy every class or lecture, yet there they are, scheduled away. I know I had problems dragging my sorry ass to French class. The big point to take away here is that if you are constantly scheduling things that you don’t like, you need to take a significant step back and review what the hell you are doing in the first place.
  • Secondly, you were not allowed to schedule your own time for classes. This is for obvious reasons, but in the real world (as opposed to whatever we might call education – an insulated experience of life?), you can often have a lot of leeway, if not total control, over your schedule.
  • Until recently, I also imagined scheduling to be the reserve of those busy-bee Japanese businessmen throwing themselves off a rooftop or having heart attacks at age 42.

The reality, it turns out, is somewhat different.

Scheduling is a technique anyone can use to ensure they live their life in balance. Most of us have to work, and work will consume a lot of the available time, but we also have side projects, social events, families, and who doesn’t want time alone to think about the more significant questions in life?

The beauty of scheduling is that it finally puts you in control. The idea is simple: you place everything you would typically put on a to-do list on your calendar, with an estimate of how long it will take.

What happened to me was that I quickly realized that I didn’t have enough hours in a week to do everything I wanted, and so I had to double down on my commitment to say no. And that is the key to being lazy: you have to learn to say no.

I then also started to test out how far I could go with delegation, to the point where I have created a list of everything that I do that is work-related, and crafted plan to pass all but the highest of responsibilities to other individuals in the company, so I can continue to do what I do best and feel happiest about.

Becoming a Scheduling Guru.

The first step is to get everything out of your head and written somewhere.

You can write it down on paper, or find a “todo” application, or use a simple text file. The tool is irrelevent.

Then, take the most pressing or important items and schedule them for the next week or two. Make sure to leave some free time between tasks, as well as factoring in the fact that you will need some unallocated slots of time for things that come up during the week.

You might find this essay on time blocking a quite useful read at this point.

I personally still keep a todo list for little things I need to remember or follow up on, but that’s pretty much it, it’s not a complex system, and that is precisely why it works. In these first couple of weeks you will encounter several issues, and I’ll try and cover the solutions to these in the following section.

One common issue is that you might start to feel like a slave to your calendar.This generally depends on your approach to life. Think about the internet, it’s a wonderful tool to help us discover new information and learn new things, or it can be a massive waste of time with cat videos and pornography.

The main thing to understand is that your calendar is mainly meant as a tool for a few key things:

  • A reality check on how much you can feasibly do over a given time frame. The idea here is not too over-promise to other people or even yourself.
  • A reminder of upcoming tasks. This point should be quite obvious.
  • A way to take a high level view and start thinking of your life in terms of weeks and months instead of hours and days.

So the main point here is that you should feel comfortable changing your scheduled items on the fly as situations change. It could be something as mundane as waking up late or being stuck in traffic, but we have to account for the fact that in real life these things do happen. We’re fallible beings, but we got to work with that, not against it.

The other main problem that people encounter with this method is that they realize that they cannot fit everything in. If you schedule all your responsibilities out and there is simply no time to get everything done, then there are two options at your disposal.

Either reduce the number of items you have on your plate, or become more efficient.

Reducing the number of items on your plate is done by learning to say no to incoming requests, or simply stopping doing meaningless work.

To become more efficient, there are several thousand books on that topic alone. Still, my main recommendation would be to focus on creating an environment that increases your ability to focus, and also thinking about new ways to solve old problems.

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