I’ve gotten a lot of questions about “my system” since my wife Instagrammed a shot of my Trello board a few weeks ago. First, I’ll admit a few things:

  • This Trello board is just one small piece, and it’s all about project management. I still capture and manage my individual tasks in OmniFocus, which so many smarter people have already adopted and written about.
  • I don’t separate personal and work tasks. For me, they’re all important and, being a one-man company, they all have to be done by me.
  • “My system” is a hodgepodge of ideas I gleaned from Accidental Creative, David Seah, Agile Results, and my own head. I only call it “mine” in the sense that I applied my own needs to some very effective systems. I probably broke stuff along the way.
  • My project management, like my design process, is constantly evolving. My board next year might look very different.

So, as I mentioned, I use Trello. I used to use Basecamp for this same system, but I have to admit, I like moving cards around on a (virtual) board. A board of columns, unlike a vertical page of lists, lets you quickly estimate the relative length of lists. I can see which lists are taller, and they should get shorter as I move from left to right (roughly). Trello is also free – so, yay!

How do I actually use Trello, and why do I swear by my (current) system? Basically, I’ve built a huge funnel out of my board that goes from big, year-sized projects down to small, day-sized bites. In a very particular order, these are my columns:

This Year

Three main projects/goals for this year. Importantly, these have to be things that I can do and aren’t related to outside factors (like earning a lot of money), and they need to be audacious enough that they’ll probably take more than one quarter to complete. Examples are writing a book, publishing a side project, etc. Obviously, this breaks the “length of column” part of my funnel, because there are only three cards. I’ve decided to let that go.

This Quarter

This is where I put all of my projects for the quarter. Once a quarter, I spend about half a day planning and filling this list with one card per project, and they need to be accomplishable within the quarter. I might break down smaller chunks from my year goals like creating an outline for the book I want to write this year. I also pull from my ever-growing “backlog” of projects/ideas in Evernote and other capture systems. Anytime I think of something amazing (or just necessary) that I can’t jump on right now, I always add it to a backlog or, occasionally, directly to this list with the knowledge I’ll be looking at it again in the future.

This Month

Once a month, I choose projects for my month by looking at my projects for the quarter. If a quarterly project can be done in a month, I’ll just pull the card over. If I have a big project for the quarter, I might make a new card for a month-size piece I can complete. In the first month of the quarter, I try to make the new list about a third the size of the quarter list. The next month, it should be about half the size. The last month, I try to move everything over or have an honest reflection on why the project isn’t happening. This is not only logical, it keeps me honest about my progress and doesn’t allow projects to “slip away” without a conscious decision.

This Week

This is the list of projects for the week. On Friday, I like to review and clean this list out. On Sunday, I fill the list back up again by pulling projects over from the monthly list. Like before, I either pull over a whole project or create a new card for a week-sized bite of bigger projects. Like a funnel, this should be a smaller subset of the monthly projects every week until I can clean out the whole list of month-long projects.


These are the three things that I want to accomplish today. At the end of each day, I review this list (which is normally emptied) and pull over three projects or create new day-sized cards for the next day. I like to get a jump in the morning right after email hits me, so I always do this the night before. Since I use OmniFocus for my tasks, I’ll normally go back and flag the day’s projects in OmniFocus in the morning. For the rest of the day, I can live in the “Flagged & Due” perspective until I’ve checked everything off. Very importantly, this has to be a list of things I can successfully finish even if some bad things happen or I have a (minor) client emergency.


Every finished card goes into this list. At the end of every day I (hopefully) move the day’s tasks over, and every Friday I move over any larger tasks from This Week that have been completed. At the beginning of each quarter, I archive the old “done” list and start a new one with the year and quarter in the title - e.g. “Done (2013 Q1)”.

My separate list of quarterly goals

I took the idea for a written list of goals from Entreleadership, though I’m sure many have talked about it. At the beginning of each quarter, I write a goal for each major area of my life: career, financial, spiritual, physical, intellectual, family, social. Again, I try to make these things that are concrete and I can accomplish (workout 4 times/week) instead of fuzzy or goals that rely on other factors (lose weight). I review these each Friday to see how I’m doing and if I need to change anything to accomplish my goals.

Well, that’s my system (in less than a thousand words), and I wholeheartedly do not recommend copying it verbatim. Instead, I’d recommend setting up your own Trello board, Field Notes, whiteboard, etc. possibly using this as a template. Then, mess it up. Change it. Make it adapt to your life and schedule, and Tweet me or email me to tell me all about it.