What I Learned About To-Do Lists From 23 Years of Trial and Error
By: Tim Jackson
Tags: Venture Capital, Startup, Management, Productivity, Leadership

To-do lists: like an endless stream of cars? Photo: Alexander Popov

Six components for a perfect to-do list, and a system for managing that list

If there’s one thing you can conclude from the 4.1m search results for ‘how to keep a to-do list’, it’s that no single answer will work for everyone. People are simply too different.

But I’ve been thinking about the issue of how to put my working time to best use for a good long time — since 1996, to be precise. That’s when I switched from a career as a journalist at The Economist and the Financial Times to founding a startup — and then, post-NASDAQ, becoming a venture capitalist and then a CEO coach. Investing and company-building are different from journalism and from many jobs in mature businesses. They need you to keep track of more things, and to take more initiatives. Being well-organised matters more.

One of the two most important things I’ve learned about using work time well, which applies to almost any job, comes from Stephen Covey’s book First Things First (on Kindle at Amazon US and UK). It’s to remember that if you’re trying to fill a big glass jar, it makes sense to put in the rocks first, then the gravel, and then the sand. Smaller items find their own space around the big ones. If you do it the other way round — if you start your day with email or with a list of tiny things — then you never have time for the big things. That’s why I schedule two hours in my calendar every day for ‘OBT’: serious projects that need two or three hours of uninterrupted concentration. For me, the best time for that is in the late morning; everyone has their own body-clock, so it may be different for you.

The sand will find its own space among the gravel and the pebbles

The second important thing I learned comes from Dave Allen’s book Getting Things Done (on Kindle at Amazon US and UK). Most people have trouble with writing to-do lists, but don’t realise why. It’s because they’ve got items on the list that are impossible to do in one sitting. ‘Organize vacation’, for instance, isn’t one task, it’s a project made up of many tasks. One, research possible destinations; two, pick one; three, decide on a way to get there, a place to stay and things to do; four, make bookings. Allen tells you that those four things are ‘next actions’ — achievable in one session if done in the right order. But the project will only cause you frustration if you allow on your to-do list.

Don’t put ‘plan vacation’ on your to-do list: it’s a project, not a next action

Once you’ve given priority to the big rocks and broken out projects into next actions, though,you still need a way to keep track of what you need to do. Dave Allen noticed that a to-do list often included a confusing set of things that were irrelevant because you couldn’t actually do them right now. You needed access to your office filing cabinet, or you needed your home phone, or your computer — so he came up with the idea of creating a separate list for each location. That’s now out of date. Many startup founders and VCs today run their work mostly from a phone and can do almost any category of task any place, any time.

But just because you can do anything anywhere doesn’t mean you should. If you have five minutes before your next meeting, there’s little point starting something that needs fifteen minutes. So it’s good to keep lists of quick tasks separate from things that need more thought or concentration.

And there’s also value in ‘habit stacking’ — doing several similar things one after another, rather than incurring the switching cost of jumbling up random types of tasks together. That’s why I like to schedule phone calls in blocks of an hour at a time, rather than allowing each call to interrupt my train of thought at a random time of day. SJ Scott’s good book on habit stacking (on Kindle from Amazon US and UK) takes this all the way; it gives you a list of 127 small actions and things to do in the morning.