Every morning I sit down to plan my day. I first look at my calendar to see how many meetings and conference calls fill my day and how much time is left to do other work.

Many consider conference calls, meetings and at times even email as disruptions of their actual work. I came to understand that these things are part of my work as well. I try to manage them and balance them with the creative and intellectual work I need and want to do, but they are ultimately part of my work.

When I went through my calendar, I estimate how much time is left and try to figure out how much work I can fit into it.

What happens next is that I go to my OmniFocus ‘Next Actions’ perspective and scan through the list, trying to pick actions that I feel are important and urgent and that would fit into the time available. Looking at actions being due (and often overdue) is the other check that is performed every morning.

Next time I look up is in the evening and I come to realise that I haven’t even done half of the actions I lined up for myself. This remains frustrating, yet happens in scaring, regular intervals. Sounds familiar? I bet it does.

What really screws up your daily todo list

I am still trying to find a way out of this dilemma, but I realise that there are at least three factors that screw my daily todo list:

1. A false sense of priority
2. A false sense of time and effort
3. Ignorance of the unavoidable

None of these is easily fixed and unfortunately your trusted productivity software doesn’t have a ‘build right and realistic daily todo list’-button for it either.

Urgent, urgent, super-urgent

How do we chose the actions we plan for the day?

First we look at what we need to absolutely do because there is a deadline (or it has even past) or someone is waiting for you and is “screaming” really loud.

Second we look at what we really, really should be doing. We feel guilty because we haven’t made any progress with a particular project. Commitments we have made with ourselves or to others return to our mind when we scan our lists.

Third and last we evaluate what we can quickly fit into the day somewhere. Sure you’ll find time for this short call, and there will be a few minutes between these two meetings to send that brief email.

As a result you actually don’t get to some tasks as they don’t fulfil any of the above criteria. Often these are tasks that are important but not urgent and that require a longer period of focus to complete.

Stephen Covey addresses this issue in his book ‘The Seven Habits of Highly Effective People’ using habit #3:

Put First Things First Plan, prioritise, and execute your week’s tasks based on importance rather than urgency. Evaluate whether your efforts exemplify your desired character values, propel you toward goals, and enrich the roles and relationships. Source: Wikipedia

Getting efforts estimated correctly

OmniFocus offers a field where you can add an effort estimation for each project or task. While I don’t use it as I don’t want another field to be filled and maintained, others use it intensively to help them building realistic workload for the day.

Dan Byler, who has contributed to the OmniFocus community many fold, even wrote a script that adds up time of the currently selected tasks to help you understand if it’s a realistic package to work on.

However, the problem isn’t necessarily in entering the time you believe a task requires, it’s your own overconfidence in what is achievable and your misconception of how long it takes.

Westheimer’s rule, which you’ll find often referenced in the context of project planning, gives you a feeling of how far off you are:

Estimate the time you think it will take, multiply by 2, and add 3.

And this is pretty much true. If you think responding to that email takes five minutes, 13 minutes is more likely. You may need to look something up, someone calls you halfway through composing the email or your energy is low requiring you to re-read the original email three times before you know what you need to respond.

There is another version of Westheimer’s rule that suggests to ‘multiply by 2 and move to next time unit’. Basically you go from minutes to hours and from days to weeks. While this is maybe taking things a bit too far, it can actually take weeks instead of days until you get to a specific task.

Your day always turns out different

In particular different to what you thought it would look like. When we build our daily todo list we pretend to live in a vacuum where:

• We don’t need to eat
• We don’t take a (coffee) break
• Never experience low energy
• No one ever calls/texts/IMs us and interrupts our current work
• No manager drops by and puts something new, important and urgent on our pile
• There are never crisis situations with a customer

And we all know this vacuum doesn’t exist unless you check into a monastery in Tuscany, Italy.

Five non-surefire tips how to fix your daily todo list

I am not going to BS you with the five things you need to do to have a bullet-proof daily todo list as I am still improving myself. But here are some ideas to look at.

1. Remember your goals

Always go back to your goals and what is really important. You can create a Single-Action List in OmniFocus that has only your top 3-5 goals as actions. Flag them or make them due, so they always display on top of your daily todo perspective. Get them on top by making sure the goals Single-Action List is right at the top of your hierarchy in the OmniFocus library and no other sorting filters are active in the perspective’s view bar.

2. Get your daily todos outside of OmniFocus

Writing your daily todos down or moving them into another application triggers additional reflection which helps you determining importance and effort involved. Use a Moleskine or Field Notes notebook, the printable CEO series Emergent Task Planner or just a simple sheet of paper. Simple todo applications as the new and hyped Clear iPhone app by Real Mac Software can also come in handy.

3. Use Westheimer’s rule for time estimation

If you rely on time estimates for tasks and projects, start using Westheimer’s rule (“Estimate the time you think it will take, multiply by 2, and add 3”) when you enter the time you estimate for the activity. Make sure, when planning your day in the morning, to also consider tip #4.

4. Plan in time for interruptions, lunch, social interactions and low energy

You can’t really plan your day. But consider the time you will need to catch up with email, get something to eat and socialise a bit with your colleagues or friends. Recognise that there a periods during the day when your energy is low. You can still do things — I keep those in my ‘brain-dead’-context in OmniFocus — but if you only line up activities that require you to operate in the 80-100% range, you’re bound to be disappointed with the actual accomplishments at the end of the day.

5. Don’t do a daily todo list. Period.

Daniel Markovitz wrote about an interesting approach in his recent post titled “To-Do Lists Don’t Work” on the HBR blog . While the general dislike of lists demonstrated is something I don’t agree with, the idea of living in your calendar as described by Daniel intrigues me. Instead of creating a daily to-do list, you can just blog time in your calendar for specific tasks. This also nicely addresses tip three and four.

The other alternative — following the good, old and still valid GTD methodology for ‘Doing’ — is to only work with your ‘Next Actions’ list and nothing else. Evaluate it by context, time and energy and you should know what you should be doing.