Effective Scheduling: Get out of that boring routine and boost personal productivity

As an entrepreneur, I make my own schedule, which means that I have to take responsibility for making each day exactly what I want it to be. If it's not, I only have myself to blame. And it's not always easy to balance business wants with my personal wants — particularly with summer in full force and lots to do.

I thought I'd write down the learnings I've gleaned from a few years of experimentation, combined with some studies and good advice that I've found around the web.

The power of routine and effective scheduling

Let me start by saying that creating a structure for each day is hugely beneficial. It can help you stick with healthy habits. It can improve sleep. It can make you more efficient and productive. It can give you something to lean on other than your willpower.

Plus, one study showed that it decreases anxiety. And another study showed that it makes stress easier to deal with.

The list goes on.

And while people often think routine comes at the sacrifice of creativity. One study showed that routines can actually make more room for creativity.

How to create a routine

Odds are you already have routines in your life, whether you know it or not (e.g. brushing your teeth). And you're probably better at them than you think.

So the first step is to identify your current routines and bullet them out. Then jot down things that you think you should be doing but you aren't. Then add everything that you want to be doing. This could also be a good time to decide what your overall goals are, as these can provide direction — for example, are you doing this to create a sense of freedom, or perhaps to provide for your family? And remember, this is not just about work. Think about projects, personal chores, social activities, spiritual practices, relaxation, entertainment, hobbies, etc. too. And don't forget about high-level tasks like reflection and big-picture work that help you to avoid getting lost in the nitty gritty.

Once you've got a list of everything you want to include, head to your calendar app of choice or a simple sheet of paper. I prefer the latter at first (here's a printout that might help).

Right off the bat, block out at least 7 hours for sleep, setting regular times for going to bed and waking up. Now, block out your off-time. And then add whatever non-negotiable commitments you have regularly, like weekly meetings.

Consider the desired flow of your day and create general blocks of time — you'll get more specific later. The humans among us follow a natural flow called the circadian rhythm, which is a cycle that repeats every 24 hours and dictates our energy levels throughout each day. It can be helpful to account for this when planning a schedule. And while it varies from person to person, most of us tend to be more alert at 11AM and 6PM, with a slump at 3PM. So plan deep work and analytical problems for when your energy levels are at their highest. When you're low-energy, it's best to take a break or knock out menial tasks like running errands, replying to emails, and so forth. Surprisingly, this is also a good time for creative activities, as studies show that we're at our best creatively when we're tired. Side note: males and females have different infradian rhythms too (i.e. longer rhythms which include things like hormonal fluctuations, and seasonal changes), which should also be taken into consideration, but I won't get into the weeds on those here.

Now add your daily tasks to these blocks from the list you made earlier. Next comes your tasks that are done weekly. Note that batching similar todos (like admin tasks) can greatly increase your productivity. Then add plenty of space for discretionary time and tasks that aren't regular. And while you're at it, include ample buffer time for transitions between tasks, otherwise you might fall behind.

It's also important to bake in scheduled breaks. The Pomodoro Technique is something you may want to consider, as it's an optimal approach for maintaining focus through a framework of sprints and breaks.

Make it all hyper-specific at first, with times down to the quarter of an hour. Once you're in the habit of it, you can loosen up the reins and allow for more flow and flexibility.

And be careful not to bite off more than you can chew, as this can be discouraging.

Honorable mention: While it's not something I have experience with, Jack Dorsey of Twitter likes to create a theme for each day of the week — one for strategy, one for marketing, etc. It makes sense and seems to work for him.

What makes a productive morning routine?

Your morning routine might be the most important part of this whole deal, so it deserves an extra mention. Why is it important? How you start your day has a big impact on how the rest of your day goes. Plus, fewer distractions in the morning make for greater productivity. And as I mentioned, your energy increases throughout the morning until it hits a peak at about 11AM. Afternoon, on the other hand, has a steep decline. So the morning is a great opportunity to do your most intensive work.

I've been getting up at 5:30 pretty regularly for a while now. It allows me to get ahead of the day and accomplish a good amount before lunch, so my afternoons can be a little less intense. I think it's a good idea to take it slow for a bit after getting up. I like to wake early but do something nourishing, like having a cup of tea, meditating, exercising, stretching, etc. Then I plan my day and get to it by around 6:30.

I'm also a fan of eating the frog. "Eating the frog" refers to knocking out the hardest task (or the one you have the most resistance to) early-on. So when you start working, consider getting that looming task out of the way first.

What makes a good evening routine

While we're at it, a quick note on evenings. Your second peak at around 6PM is a good time to wrap up loose ends, reflect on the day, prepare for the next day, and relax.

Calendar tips

If you use your calendar to handle your routines. Here a few notes for consideration:

• Find the app that's right for you. Here are a couple of best-of lists for calendars.
• Download your calendar app of choice on your mobile so that you don't have to be at your computer all the time.
• Consider color coding your time blocks and events, as this can make cluttered calendars a little less overwhelming.
• Got calls? Be the one to suggest a time first. And try to block all your calls into one block so that you aren't being interrupted throughout your day.
• Set reminders and notifications.

How to stick to it on a regular basis

I've heard that it takes 21 days to start a habit. And I'd love to tell you to just stick it out for 3 weeks and then you'll be good to go. But as it turns out, that isn't true. The truth is that there are entirely too many variables to really get a clear idea of how long it takes. For example, one popular study averaged 66 days, but the range was from 18 to 254 days. Still, making a commitment for a specific time frame can be helpful. A month could work well, or two if you really want to go for it. Keep optimizing as you go, and do a post mortem once the time is up to see what worked and what didn't.

For me, as well as others I've spoken to, starting is the hardest part. Once it's going, it's easier to keep it up. The trouble is, as soon as you break the routine once, it gets easier to keep breaking it. So it's really important to stick to it. The Seinfeld technique can be helpful in this regard — I know some indie hackers who swear by it.

Beyond that, track yourself and hold yourself accountable (or ask a buddy to check in with you about it). There are habit trackers that can help with this too, like @xenodium’s Flat Habits or @mikekreeki’s Lunatask. Remind yourself why you're doing it. And reward yourself for upholding the routine. The best routines have an inherent reward, like a reduced stress or a feeling of balance, achievement, satisfaction, or even joy. But you can always slip yourself a treat from time to time too. And you can also reward yourself by getting tasks done efficiently and using your extra time to do something you love.

If you're having trouble, try to get to the bottom of it — the likelihood is that this difficulty is a symptom of some root issue. A good way to dig into it is by asking yourself "why" again and again (e.g. Why can't I get up early > because I go to bed late > why > because I finish my work late > why > because I have too many meetings > why > because I have trouble saying no > and so on). So dig deep.

And if you just really can't do it, ask yourself whether these are really things that you want to do. It might be time to reevaluate what's important to you.

Boosting your personal productivity

Outside of scheduling, there are a lot of ways to make yourself more efficient. Check out my post on time efficiency.

Good luck 🚀