Yeah, that’s a nine-day grid, 8am – midnight each day scheduled.

Frequently, when talking with an artist, a professional colleague, or friend and the issue of time management comes up. They ask: How do you do it? How did you start it? What system do you use? How should I get into it? Well folks, there’s a ton of How To Manage Your Time Like a Boss posts out there, and this isn’t one of them. People talk about time management like it’s some sort of silver bullet that is going to make you happy and dependable and adult and amazing. But what they don’t tell you is the dark side of time management — how it can make you a self-centered, freaked out, miserable troll that everyone hates.

That’s what I’m here for.

Some back story: In graduate school, time management was essential. Prior to grad school, in my mind, time management was for rigid losers and uptight soccer parents. Between running the Fine Arts Library nights and weekends, sitting on a leadership board for the student chapter of the Special Libraries Association, a full docket of graduate level classes in user research and information architecture, and a pretty dedicated interest in getting obliterated and making terrible life decisions with new grad school friends, if I wanted to do anything at all, it had to be scheduled.

It started innocently enough as a lightweight weekly checklist but soon turned into a complete lockstep hour-by-hour gridlocked hand-drawn shit show.

If it was in the book, it got done in that time frame. NO EXCEPTIONS.

• If it said I was card sorting from 3pm – 9pm Thursday March 27, I WAS CARD SORTING.
• If it said I was setting up a conference 8:30am – 9:30am Saturday March 29th, I WAS SETTING UP A CONFERENCE.
• If it said I was getting drunk from 10pm – 4am later that night, I WAS DRUNK.

If I was having any sex at the time, it probably would have been in there too. I wasn’t — BUT WHO NEEDS SEX WHEN I HAVE A CALENDAR?

So, this worked pretty well, and I started to get a reputation for insane levels of accomplishment and simultaneous debauchery, made possible only by this time management system. One of the support staff at my graduate program even asked me to give a mini lecture on time management & organization techniques to incoming grad students who were overwhelmed by the idea of complex time management and task prioritization.

So, I thought I was pretty damn cool — until my birthday weekend.

Thinking that my three days in my hometown celebrating my birthday would be best spent structured like grad school to “maximize family events and fun,” I made a single-page PDF, hour by hour, outlining all of my scheduled activities for the long weekend. I, being the psychotic control freak helpful person I am, made printed copies for everyone in my family, and highlighted when and where I thought each individual family member should join me while I was home. The calendar in the book had jumped off the page and BECOME ALIVE! My mom and friends each took their copy graciously and said, “Ok, thank you … ?”

But not my brother. My brother took his copy, tidy and cheery with bright yellow highlights, looked me dead in the eye, and said, “THE FUCK IS THIS?” Enraged and shaking his head, he crumpled the paper, jammed it in his pocket and said no more. I thought he was going to punch me in the face. Clearly, he was not impressed with my scheduling micro-managerial disrespect for everyone around me. I’m not sure he talked to me at all for much of the weekend.

There was a lesson here.

A painting I did of my brother, irate about my PDF.

After this happened, and after a few “caring confrontation” discussions with my brother, I started to re-evaluate my relationship with scheduling. I looked around and asked my friends: Did people dislike being around me because of my rigid scheduling? Had scheduling started to destroy my relationships? My own sense of self? My ability to be present in my own life? Was I unable to be happy if my myopic view of time wasn’t shared by others? WAS I ADDICTED TO SCHEDULING? WAS MY NEED TO CONTROL TIME OUT OF CONTROL? GASP!

Yes. Yes it was.

And yes, full disclosure, not gonna lie, I sure as shit am still addicted to scheduling and calendars. I’ve moved from my antiquated, quaint paper system and am now freebasing calendars and schedules digitally.

Right now my calendaring drug of choice is Google Calendar. People at work and friends openly mock me about it. When talking about the inevitability of death recently with a friend, they quipped: “So, I’m guessing that’s already on your GCal, right?” NO COMMENT, ASS.

But, there’s hope. I’m getting help my brother has threatened to hack my Google Calendar and delete it if I don’t shape up. I’m working on flexible, considerate, collaborative scheduling. If something doesn’t get done today, I can do it tomorrow. If someone else is involved, I ask them what works for them BEFORE I schedule it. I ask other people to schedule things and then I attend to them or move my schedule around to accommodate their needs. I schedule long blocks of time that are marked as “NO PLAN ZONES.”

I’m practicing mindfulness shit to help me stop needing so much structure to feel OK every day.

So, what’s the point? The point is this: Artists, creatives, designers, musicians, freelancers, writers, all of you — YES, you have to manage your time and be organized. YES, keeping a schedule is useful. YES, use tools to keep your stuff in order. YES, don’t be a flaky sack of shit. But be careful because calendaring and scheduling can absolutely become an obsession or addiction that can limit your spontaneity, creativity, ability to enjoy free time, and end up making you an alienated megalomaniacal egoist who values the forward march of time over actually living life and building respectful relationships. Aim for the middle ground. Enough structure to get things done and be a dependable adult, without creating unnecessarily limiting, arbitrary, and frustrating time boxes.

Some people turn to drugs, alcohol, sex, gambling, food, religion, self abuse, etc. to cope with the stresses of life. Others might turn to scheduling to create a sense of control in the abyss of uncertainty. Those innocuous white-space-laden monthly calendars with slick mid-century modern designs, comforting puppies, or edgy photography on the cover are just a gateway drug in disguise. Next thing you know you’ll be compulsively adding idiotic events like “Take a Shower” to your Google Cal secretly from your iPhone at 4am, hoping your partner doesn’t wake up, look over, and (rightfully) demand a divorce. Be careful out there with those calendars, kids.