Jennifer writes in:
“I was wondering, though, if you would consider another post that goes a bit more into detail on how you break down your larger goals? Particularly, I would love to see an example of a project that you created daily tasks for that eventually led to a larger goal. Do break things down at the beginning and then filter tasks into your to-do list from a master list? Or do you have another such plan of action?“
This is something I’m constantly doing. I usually have several different large projects going at once and knowing how to effectively keep track of them and manage them while also making sure I move forward on them each and every day is absolutely vital.
Here’s how I manage this.
Brainstorming and initial project planning
I’ve got a big project in mind – say, writing a novel. I’ve given it some thought and I’ve decided to commit to actually carrying that project through to the end.
The first step I take is that I have a brainstorming session. I usually do this over the course of several days in short sessions of fifteen to thirty minutes spread across those days.
In those sessions, I try to break down that big project into smaller pieces and come up with an ordered list of what would need to happen to carry this project from start to finish.
With a novel, for example, I might have a list that involves drafting character sketches, drafting a plot outline, writing a first draft, revising that draft, sending that draft through an editor, sending that draft out to a few test readers, then packaging it up and trying to sell it to publishers. That’s just a rough example.
Usually, my list consists of pretty big milestones in the overall project. It usually numbers somewhere between seven and twenty items that are roughly of the same size.
For each of those items, I try to write a sentence or two that explains what exactly I need to have completed in order to consider that part “done.” Sometimes, it’s self-evident. Sometimes, it’s not. It really depends on the project.
When I have that final list – which usually comes together over several brainstorming sessions – I save it in my preferred list manager, which is Remember the Milk.
Breaking down the first step
The next thing I do is repeat the process with the first element on that list. I try to break it down into a list of seven to twenty small milestones that I’ll need to achieve in order to say I’ve finished that first item. Again, this takes some brainstorming, but it usually doesn’t take nearly as long as the first session.
After this, I’ll save that list.
I’ll then repeat this activity using the first item in this new list I’ve generated. I try to come up with a list of seven to twenty items I’d need to achieve to consider that one item done.
I keep doing this until I’m breaking an item down into pieces I can achieve in fifteen minutes or so.
So, let’s say I have a project in mind and I’ve broken it down into ten items. I’ll take that first item – we’ll call it item 1 – and I’ll break it down into ten items. I’ll take the first item off of that list – we’ll call it item 1.A – and I’ll break it down into twelve items. I judge that each of those items will take me around fifteen minutes or so, so I’m satisfied.
The “next action”
Now, from that list where I’ve broken things down into fifteen minute bits, I designate the next uncompleted item on the list as my “next action.” That “next action” gets added to my to-do list for the day.
So, how does this work? For each project I have, I have a set of two to four lists as described above. One is the big project outline, the next breaks down my current step in that big project outline, the next breaks down my current step in the second list (if needed), and the final one breaks down my current step in the third list (if needed). All of those final lists – the ones that are full of fifteen minute (or so) tasks – are marked with a special designation – I call them “na” lists (for “next action”). Since it’s all stored electronically, I just look for the lists that start with “na-” to find what I’m looking for.
I just go to each of my “na” lists, pull the top uncompleted item off of each one, and then add those items to my to-do list for tomorrow. Then, tomorrow morning, I just pick up my to-do list and I’m ready to go.
Once a week, I spend some time reviewing the state of each project. I usually do this on Saturday or Sunday afternoon during “quiet time” (when our youngest is taking a nap).
For each project, I just make sure that things are actually moving forward smoothly and that I’m happy with the progress on that project. I also look at my lists and see whether or not I’m going to finish up one of my “next action” lists in the next week and, if so, I brainstorm the next list by going back up to the master checklist and moving down through each incomplete piece as described above.
So, for example, let’s say I have a project list where I’m working on the first step, a list of elements for that first step of which I’m working on the eighth piece, and a list describing all of the elements I need to complete that eighth piece. I see that I have only two things left to do on that eighth piece, so I’m likely to finish it this week. I’ll go back, look at the ninth piece, and brainstorm a list of what needs to be done to complete that one. That way, during the week, I can seamlessly move onto the ninth piece when the eighth piece is finished up in a few days.
This system takes time, don’t get me wrong. However, it is unbelievably effective at making sure that I always have a manageable next action to take on any project I’m serious about.
Without that “next action” always at hand, it would be really easy to just give up on a project and not bother to complete it. With that “next action,” I know that if I just do this fifteen minute thing, the project is moving forward and I’m actually moving toward completing whatever it is that I want to complete.
For me, Remember the Milk and Evernote have been vital tools in all of this. Evernote is where I do my brainstorming and my jotting down of ideas and my rough organization of them. Remember the Milk is where I store all of the lists, along with my ongoing personal to-do list.
This is how I do project management. Without this system, I would have never been able to write two published books or to launch The Simple Dollar and make it successful or to achieve several other things in my personal life.