The Rise of Difficult People

“He who conquers himself is mightier than he who conquers a city.”

A few years ago, I helped start a group in Cleveland called the Society for Difficult People.  The idea was simple: we’d meet once a week for breakfast before work.  At the very first breakfast, we’d commit to doing something subjectively difficult in the next week.  Then, the next week, and every week after that, we’d review how well it went, then commit to something new (and difficult).

The benefits, as I saw them:

  1. We’d do things that expanded our abilities and personal power.
  2. We’d get in the habit of facing our fears and weak points, and pushing beyond them.
  3. We’d be able to develop new habits in a supportive environment.
  4. We’d learn what other people found difficult, and be inspired by each other.
  5. We’d commit publicly to doing things, so we’d be held to more accountability.

It totally worked.  I don’t want to break the confidences of other members, but personally, I did things like:

  • Swam 7 kilometers (3.5 hours of laps);
  • Cleared my email inbox and stayed at inbox zero;
  • Read three books in a week;
  • Finished several projects;
  • Buried the hatchet with someone I really didn’t get along with;
  • Started a debate club;
  • Learned how to breakdance and box;
  • Gave up three board positions and dance lessons (I really like being involved in things, so this was probably the toughest thing I did);
  • Shut down my Facebook account for a month and, after that, I only checked it once a week for a couple of months.

Many of these were life-changing.  For example, inbox zero: with email mostly under control, I have decided to delay all personal emails to either Wednesday or Saturday, delete most mass emails, and reply to anything potentially related to work once a day, at 4 p.m.  Realizing that email gets in the way of work has helped me focus more on what I’m doing during the day.  Giving up Facebook was even better: without checking in on other people, or posting, I didn’t feel nearly as much daily anxiety as I did when I was checking it regularly.  Burying the hatchet helped expand my interpersonal skills; swimming, boxing, and breakdancing helped me expand my physical limits and abilities.  And giving up involvement in organizations in order to focus on what is important to me really helped show me how valuable time can be, and how much can be done when we stop “majoring in minor things.”  Developing habits of doing things, and only focusing on one thing a week, was better than making a list of all the things I wanted to do; sitting up straight AND eating better AND daily meditation would have been too much to tackle at the same time, but, divided, I could approach them all and improve myself over the long term.

The people in Difficult People still occasionally post on a private Facebook group, but the meetings don’t occur any more.  However, I’ve kept up a personal commitment to facing one difficult thing every week since I moved away from Cleveland, as I found that the weekly self-evaluation was a great opportunity to evaluate my life and see what was and was not working, and look for ways to improve myself.

Now, I think I will take this blogging opportunity to start publicly committing to do something difficult every week.

This week:

I face a lot of different challenges: being in a new city, being in an extremely intensive learning environment, and I’ve started eating poorly again.  I’m taking diet head-on by making my food ahead of time and eating pre-planned meals, so that shouldn’t be too much of an issue.  Focus is my main concern.  So in class, my difficult thing will be focusing solely on what we’re doing in our lessons, and then reinforcing those lessons every night in 30 minutes of review, above and beyond our homework.  

Also, my friend Jonathan saw what Eric, Teddy and I were doing, and decided he wanted to join in blogging daily.  Because we’re in September already, though, I’m going to publicly challenge him to post once a day for September AND October; I’ll do the same (and invite Eric and Teddy to continue as well, if they want).


  1. […] been a good rhythm so far, a good constant. I plan on continuing into October, as well. And as Andrew writes today, our friend Jonathan has joined him and me and Teddy in our daily writing practice. You should join […]


  2. […] week was really, really tough.  The coming week will, I suspect, be even tougher.  My goal, my difficult thing, for the week: take more regular breaks, regardless of whether I’m doing well or poorly, with […]


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