Flexibility vs. Discipline: Where do you stand?

For years, I’ve wondered if there’s something wrong with me because I’ve never been able to get organized.

By “get organized” I mean adopting and consistently using some sort of calendar, reminder, to-do organizer, time management system so that:

  1. I don’t have to keep it all in my head; and
  2. I can use my time in the most efficient way possible.

All the most successful people seem to be extremely disciplined masters of their schedule. They do NOT just do whatever they feel like, whenever they feel like it… instead, they establish habits, procedures, and systems that enable superhuman productivity with little stress (and zero wondering if you’re forgetting about something important).

The problem is that I’ve never found a system that’s more reliable than my own head. My memory is pretty darn good.

I’ve tried a whole host of productivity / to-do programs, but here’s the problem: my life needs more flexibility than those programs are set up to give it. I’ve tried to give myself a consistent, carefully-planned schedule, and I just can’t pull it off.

Something always comes up that requires reshuffling of priorities, tasks, and scheduled items. I know that sounds like an excuse, and maybe I’m just not hardcore enough to put “the schedule” above everything else – but one of the advantages of being self-employed is having the ability to flex my own schedule, so I don’t want to completely lock myself into an iron-clad self-imposed routine. Plus, there is no way to schedule inspiration, energy levels, and a flow state for creative work.

The result is that I end up spending ridiculous amounts of time rearranging items in the system/list to compensate for the flexing, which is counterproductive and takes up more time than it saves.

And God forbid the tasks start to build up in the system – then you have to face the crisis of deciding which is more important:

  • the most urgent task for today?
  • the two overdue from yesterday?
  • that lingering one you were supposed to do a week ago?

Since I’d often forget to log into and check the system for various days in a row, this would happen to me frequently. I think my “Todoist digest” has 64 overdue tasks.

I tried to stick with good old-fashioned pencil and paper for a while, too. Gave that a solid 2-year effort. But eventually pretty much every page in my planner looked like this:


…overstuffed with info, with arrows flying around and plenty of cross-outs as I postponed rescheduled things.

I’ve also toyed with the idea of setting no goals, letting go of plans, freeing myself from expectations, and simply following my passion and creative flow, Zen Habits-style.

But sometimes my creative flow would get stuck between Twitter and Facebook. Plus, there are parts of every project – no matter how passionate I am about it – that are just not enjoyable to work on. So I discovered that goals are really needed to kick passion into action.

I was about to abandon the last shred of hope of ever having an effective organizational system outside of my head when I discovered a little gem of a website called FollowUpThen.comIt allows you to send or forward an e-mail to a particular date/time (ex. 5pm@ followupthen.com or nextwednesday@followupthen.com) and the e-mail will re-appear in your inbox then.

Doesn’t sound all that revolutionary, but here’s why it’s the perfect solution for me:

The only productivity habit I’ve ever managed to adopt is Inbox Zero.

…okay, more like “Inbox less-than-ten.” I live in my inbox, and I HATE to see messages build up. So much so that I never let it happen. I’ll DO stuff purely to be able to hit “archive” on the message and get it out of sight and out of mind.

So I set up a bunch of recurring e-mails at FollowUpThen:

  • Monthly reminders for rent, capoeira academy fees, & translation invoices – no more “oh man I have to find time to get to the ATM tomorrow”
  • Bi-weekly reminders to clean the house (Mondays & Thursdays – but it doesn’t matter what time. I’ll get the e-mail in the morning and if I feel like cleaning in the morning, great, but if I want to do it at 4 PM that’s fine too – it’ll just stay in my inbox bugging me until I finish it)
  • Bi-weekly reminders to write the next Espresso English newsletters (Wednesdays & Saturdays)
  • Daily at 5 PM reminder to hit the grocery store before it closes. So once a day I take a quick inventory of what needs to be bought. This way I’m not constantly wondering if I need to grab something at the store, and/or making multiple trips because I’ve forgotten something.
  • Daily reminder to responding to e-mails from my Espresso English students and subscribers, so that everyone receives a reply within 24 hours.
  • Daily e-mail at 10 PM titled “GET OFF THE COMPUTER and go meditate / reflect / read” – I’d really like to stick to a nighttime cutoff, to help improve my sleep quality and also ensure that I always have some time for reflection.

When one of these comes in, it sits in my inbox. Mocking me. Until I do the task and can delete the reminder with a flourish.

Warning: This strategy will only work if you’re pretty good at keeping your inbox clean and minimal. Otherwise the reminder e-mails will just build up and make you feel even guiltier.

This system is just rigid enough to keep me on track and make sure I don’t forget anything important, yet also flexible enough to allow me to do things at any point in that day when I feel my energy/flow is best for it.

Also, since it doesn’t rigidly define times (i.e. from 7-10 AM you MUST do X), it can accommodate unexpected additions to the schedule.

I think I may have finally discovered my “system”!

How do you organize your life? Are you on top of your game, or still looking for an effective system?