Are you restricting yourself too much? Attempting to stick to a too-embracing structure? It might be time to loosen up a bit.

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Script | 310

Hello, and welcome to episode 310 of the Working With Podcast. A podcast to answer all your questions about productivity, time management, self-development and goal planning. My name is Carl Pullein, and I am your host for this show.

Having some kind of structure or routine built into your day is important if you want to consistently get the important things done. The trouble starts when you try to stick to that structure or routine too rigidly. It begins to limit what you can do and holds you back from accomplishing the things you set out to accomplish. Plus, if your plan is interrupted by the inevitable “emergencies”, the plan is usually thrown out the window, and everybody else’s problems become the focus.

I’m all for building a structure around your day and week. It’s this structure that will ensure you get the right things done on time every time. But sometimes, something will inevitably come along and stop you from sticking to your routine or structure, and then, if you don’t have built-in inflexibility, everything will come crashing down. Either you drop everything, which leads to a build-up of backlogs, or you’ll stay too rigid and miss an opportunity that could lead to bigger and better things. 

This week’s question goes to the core of this dilemma, and I hope to give you some ideas to prevent it from happening to you. 

So, let me hand you over to the Mystery Podcast Voice for this week’s question. 

This week’s question comes from Andre. Andre asks, Hi Carl, I love the idea of having a structured day, but I am having a hard time sticking to my plan. I never seem to have enough time to get all my work done, and I have a huge backlog of emails and project work to catch up on. It’s causing me so much stress and worry. Do you have any advice? 

Hi Andre, thank you for your question. 

You are right to create a structure around your day and week. Aside from weekly planning, I would say if anyone wants to become better at managing their time and ultimately more productive, they are going to need some form of structure to their day. 

However, as with most things, this can be taken too far. Take time blocking, for example. Time blocking is an excellent way to make sure you have enough time to do the critical things that need doing, yet if you try to micromanage your day—that is, you block your whole calendar—you only need one meeting or one task to overrun by just a few minutes and your day is destroyed. For time blocking to work effectively, you will need plenty of blank spaces. 

For example, you may wish to block two hours for some deep work in the morning, say, between 9:30 and 11:30, then an hour for managing your communications and an hour for clearing your admin tasks for the day. That way, if you work a typical eight-hour day, you have four hours for anything else that may come up. 

However, this rigidity may also be coming from outside forces. 

I love reading contemporary history. My favourite era is between 1945 and 1990. These were transformative years in both the US and Europe. I am particularly interested in how creative people, like Ian Fleming, the author of the James Bond books, managed their days. 

What was noticeable was with few exceptions, there were no rigid working hours. If you worked in a factory doing physically demanding work surrounded by dangerous machinery, there were laws in most countries preventing you from being forced to work beyond eight hours. For the rest, you worked until the work got done. 

And between 1940 and 1980, there were no computers helping you to do your work. If you needed to write a report, you either sat down at a typewriter and typed it yourself (no delete key with typewriters—if you got a page wrong, you began again), or you may have been lucky and were allowed to hand the work to the typing pool for typing up—and then you either needed to handwrite the report or dictate it. 

And don’t let anyone tell you that people got less mail in those days. People got a ton of mail each day (often quite literally). It wasn’t electronic mail; it was physical mail, and responding to that wasn’t as simple as hitting the reply key and typing. There were conventions to a written letter. You could never write, “Please find attached the file you requested”. You had to include a greeting and an ending, then sign it by hand, stick it in an envelope and take it to to post room. 

There were a lot of late nights in the office getting work finished back then. Probably a lot more than we have today. I also remember in the 1990s regularly having to come into the office on a Saturday to clear files that needed clearing before the start of a new week. 

Yet people adapted, and the work got done. 

In many ways, we might be attempting to structure our days in the wrong way. Let me give you an example. 

I’ve recently been reading a biography of Winston Churchill. Now, Churchill had an unusual structure to his day. He would wake up around 8:00 and while in bed, read the newspapers and deal with his communications. He’d read his letters, call a secretary into his bedroom and dictate the replies. 

He would get out of bed at 11 am and take a bath. Often, he’d have a secretary outside the bathroom door taking more dictations—that could be a speech he was preparing or one of the many articles or books he wrote. 

Let me pause here. In the 1930s, 40s and 50s, only a privileged few could afford to hire their own secretaries or assistants. Today, it’s relatively affordable to hire a virtual assistant, or you could learn to use the dictation features on your digital devices. This means you could dictate in a Churchillian way—while taking a bath and while reading your emails in bed. 

After his bath, Churchill would come downstairs for lunch. This wouldn’t be a sandwich while sat at his desk. It was a full hour affair with wines and champagne. After lunch, he’d walk around his garden, feed the fish in his pond, and often paint. This was his rest time. A time when he spent some time thinking and relaxing. 

Then, at 4:30 pm, it was nap time, and again, this wasn’t a quick twenty-minute nap. It was a full ninety minutes. After his nap, it was another bath, then some card games with his guests or family before a full dinner—including an array of alcoholic drinks. 

At 10 pm, Churchill would disappear into his home office (or “factory” as he called it), where he would work solidly for the next four to five hours. Then it was back to bed. 

If you look at Churchill’s daily structure, it was solid. It got the important work done, and it was conducted on his terms. It was unconventional by the standards of those days. His “class”—the upper class—would usually disappear to their clubs after dinner for meetings and socialising. Yet, Churchill got a huge amount of work done. He wrote almost fifty books in his lifetime, thousands of articles for newspapers and was a full-time parliamentarian. 

I tell you about Churchill because his daily structure is a great illustration of what you can do when you work within your own ideals. Churchill was a night owl, not a morning person. He took advantage of that by doing his most important creative work late at night. Tim Ferriss, the author and entrepreneur, is another person who likes to do his creative work late at night. 

When people see my calendar, they think I am working too much. Yet, if you look closely, I do my creative work in the mornings, then take the afternoon off (in the same way Churchill did) then return to my work after dinner. I get four or five hours of rest from work every day and can enjoy it in daylight when the cafes are open and when I can actually enjoy living close to the beach. I am also a night owl. 

What Churchill did was have some solid structures in his day. These were his wake-up time (8:00 am), lunch and dinner times. If he had guests for dinner, he would stay talking with his guests until late into the evening but would still return to his home office to work until he was tired enough to go to bed. 

I fear many people have come to believe it is bad to work after they finish work. But do you really ever finish work? I’m not suggesting you always take work home with you, but if you have backlogs and project deadlines approaching, perhaps giving yourself an extra hour or two in the evening to do a little more work isn’t such a bad thing. 

Think about that for a moment. You have the choice of two evils. The stress and anxiety of worrying about all the work piling up and not getting done. Or extra time in the evenings to get on top of the work. One will lead to health issues, and the other is inconvenient. 

I remember reading about Michael Dell’s work routines when his family was still young. He would ensure he was home by 7 pm every evening for the family dinner. After dinner, he would play with his kids until they went to bed and then go to his home office to work until midnight. 

Hopefully, your days won’t be destroyed too often, Andre, but it is going to happen—that’s inevitable. The key is to be flexible. Over time, you will learn to distinguish between the genuinely urgent and the false urgencies. The thing is, and the reason I told you about Winston Churchill, is you have options beyond nine til five. 

Tim Cook is famous for waking at 3:30 am and doing his email—he is clearly a morning person. Former President Jimmy Carter would go to the Oval Office at 7 am every morning to read through the reports he needed to know about that day before having a meeting with his security advisor at 8:30 am. 

Productive days are not built by accident. They are built on structure. We can learn from immensely productive people like Churchill and build a structure around meal times and rest. 

Insisting you must not work in the evenings is admirable, but if you have outstanding work to be done and a backlog of emails and other messages, what is that doing to your stress levels? Would it not be better for your long-term mental health to spend a few evenings or early mornings getting on top of that backlog so you give yourself less stress and more free time in the long-term? 

Thank you, Andre, for your question. And thank you to you, too, for listening. It just remains for me to wish you all a very, very productive week.