Simplify your ToDo list (part 1)

I’m mostly agnostic about how people track their To Do list, and I’ve seen nearly every system work and fail: walls full of post-its, whiteboards, online calendars, iPhone apps, GTD, handwritten paper lists, index cards, and Excel spreadsheets. In general, the system that works for people is the system they’re willing to commit to and use regularly, and nearly anything will work. For entrepreneurs who are having trouble juggling all of their responsibilities and commitments, I tend to track their major commitments week after week, so that we can notice patterns in what is getting done, and what isn’t.In a typical week with no major emergencies, several of the items on the list will be finished, or at least be off to a good start. But, there are often a few items that linger on someone’s to do list for several weeks or even months. When that happens, the client and I do some detective work to figure out what’s going on.Here are the typical reasons for something that doesn’t get done after several weeks, and the conversations I have about each one:(1) You are blocked by lack of information or need new skillThese are fairly easy to detect and correct. Asking “is there anything you need to know or learn to get this done?” will reveal anything concrete that’s lacking. Then we can focus on who to ask for help, where to get the info, how to learn the skill, etc.(2) It’s super boring, tedious, or otherwise unpleasantYou can hear this one in people’s voice as they talk about the task: it’s just something they flat-out don’t like. There are three possibilities here: suck it up and do it yourself (good for a one-time thing), hire someone else to do it (good for repeating things that you’ll struggle with in perpetuity), or decide it doesn’t matter enough for anyone to do. These are overly simplistic, but they are pretty much the only options.(3) You are blocked by a belief or fearThis is also fairly easy to detect. Asking “If there was anything scary about doing this, what would it be?” and “If this were challenging for someone to do, what would be the hard part?” (Keeping the question phrased as a hypothetical defeats the concerns people have about saying they’re fearful or having any difficulty. Seems crazy, but it works great!)  Then we have a conversation about how realistic that fear is, or how real that belief is, and what some other alternatives would be. Doing this delicately and respectfully is important, but not too hard once you get the hang of it.(3) You are too busy to do this right nowI’m also listening for how pressed a client is in terms of time. Are they reporting that most things are getting done each week, or that they’re short on sleep, constantly juggling tasks, and context switching all the time? If so, the solution might be to mothball one of the major or minor projects on deck, and come back to it when other things have been completed. This reminds me of Agile projects tracking a team’s velocity: an entrepreneur only has a certain daily or weekly velocity, and piling on more commitments than the current velocity leads to wicked amounts of context switching, and less effectiveness overall.This is consistently one of the hardest conversations I have with clients: releasing someone’s ironclad grip on something that they want to do, based on the reality that they only have so many hours in a day, turns out to be surprisingly difficult. Entrepreneurs are born with an inherent optimism about what they can accomplish, and the idea that everything isn’t possible is almost like telling a little kid that there is no Santa Claus. But, the entrepreneurs who do develop a sense of their realistic working velocity have a far easier time in the long run, and I don’t see evidence that they are accomplishing less. They are just choosing more carefully what to focus their energy on.If we can see the evidence that major things are consistently falling by the wayside, then we talk about how either you can choose what you want to focus on, or life can choose for you. We sometimes stack-rank (another Agile term) all of their major commitments. If you had to pick what to do first, what to do second, etc., what goes where? Usually the thing at the bottom of the list needs to go, at least for now. Putting it on temporary hold (for a week, or for a month) can sometimes be emotionally easier than canceling it outright. Also, talking about a future two years out, and what life would be like if this just didn’t get done at all, might be a big help.I call this “Minimum Viable ToDo List”, and I find that many people benefit immediately and measurably from giving up on something, rather than learning how to do things more efficiently, tracking them better, or beating themselves up about what isn’t getting done. As an entrepreneur’s company becomes more successful, they will be constantly giving up more responsibility for parts of the business that aren’t their passion. The best entrepreneurs are the ones who learn what their true velocity is early on, are wildly successful at saying “no”, and can focus all of their energy on the things that are most important to their success.