DrawingMyDreamMap, Time Management

How I Perfected My Calendar ๐Ÿ“†

Does my calendar pass the smell test? If someone observed me for a week what would they think is important to me?

๐Ÿค” The Problem: I Can’t Find a Schedule That Works for me

I’ve been battling with my calendar for ages, fighting for the cause of a life lived unstructured. They’ll write history books about the war. Film makers will make movies about it. When I started this site I went into a cease fire. I figured as long as I was spending time making content for the blog that my calendar would work itself out.

Well, let me tell ya.

It turns out that me and Cal just needed some space.

โœ‹ Raise your hand (honor system) if you agree with any of this:

  • I don’t like scheduling my time.
  • I feel busy, like I’m not getting what I want out of life.
  • I’m not a morning person. I’m not a night owl. I’m my own person and my calendar should reflect that.
  • I’m afraid that if I schedule my life that life will be boring and I’ll lose that sense of spontaneity.
  • I find calendars suffocating. I don’t want to be scheduled down to the minute. Plus, all the time to maintain a perfect calendar…yikes ๐Ÿคฎ!
  • I hate calendar reminders. so. much.

Each one of those bullets describes me. I’ve read so much about morning routines that my eyes rolled back into my head years ago. I’m not interested in #EarlyBirdTok or #NightOwlTwitter ๐Ÿ™„.

So what’s the point?

๐Ÿ’ฏ I’ve Done it! I Found The Perfect Calendar

If you’re an early bird, turn back now. You can’t un-see this ๐Ÿ™ƒ.

My time falls into 3 categories:

  • Routine
  • Free
  • Dream Map


๐Ÿ”ง Routine

Routines are activities that must be done that don’t move me any closer towards my dreams. Taking out the trash won’t make my dreams any more real, but it will keep my place from stinking up. These tasks have no real upside, but do have a real downside.

Routines are broken down into two sub-categories.

  • โณ Time-dependent, things that must happen at a set time
    • Example: my day job. I must work at the same time every work day.
  • ๐Ÿฆ‹ Time-independent, things that must happen, but not at a set time
    • Example: taking out the trash
โšก Free

Free time is value add time because I like to enjoy life and it gives me an opportunity to recharge. Waking free time is unstructured. For more on free time, check out my essay interrogating “default free time.”

๐ŸŒ Dream Map

Dream Map time is where I spend time on what’s important to me. This is where I work towards my Dream Map.


The Code is more like "guidelines" rather than actual rules - Barbossa meme  - quickmeme
Pirates of the Caribbean
  • The calendar is a guideline. It is NOT a set of rules. It’s not about adhering to the calendar. It’s about using the calendar as a framework to help me stay on the right path. For instance, if I miss a night of Dream Map work to do something else that’s fine because I know I’ll get right back to it at my next Dream Map opportunity.
  • Avoid self-sabotaging behaviors. Stick to my bed time on week nights. Since I like to work before bed because that’s when I’m most able to focus, I need to have energy at the end of the day to concentrate. If I stay up late tonight it interferes with my ability to get sh*t done tomorrow.
  • Minimize context switching. Multi-tasking is a myth. Orient schedule so I can focus on one thing at a time. Although sometimes the situation might call for multi-tasking, I shouldn’t plan to multi-task.
  • Keep time blocks in their lane. The biggest risk of this is my day job. Before working late didn’t interfere with anything of substance. Now, it does. It took courage to set boundaries at work, but with time the boundaries became easier to enforce.
  • Beware of “time craters.” Unplanned items left without guard rails can take up a lot of your time (๐Ÿ‘€ @Twitter). It’s not about avoiding them. It’s about being aware of the time you spend so you can make the choice of how you spend your time (rather than getting sucked in and losing control of your time).
  • Doing anything is about a slow & steady progression (see: the planning fallacy).

My Calendar

my perfect calendar
Ta Da!

๐Ÿ”‘ Why it Works for me

My Routines…

  • Are…My day job and my chores
  • When?…Immediately after work. They are mindless and require energy for motivation. They are also a good cleanse between my day job and other important activities.

My Free Time…

My Dream Map Time…

  • Is…for anything that moves me towards my dreams.
  • When?…week nights, last thing I do before bed. Doesn’t require energy as motivation because the stakes are high and these activities are highly aligned with what’s important to me.

๐Ÿ’ญ Closing thoughts

I can’t control the future, but I can influence it. It doesn’t make sense to me to carefully map out all my tasks onto the calendar. For one, I’ll learn stuff along the way that will inform what my calendar should look like and for two, I find it dreadfully boring executing a set of tasks and letting my calendar lord over me like a miser. I much prefer this approach, using the calendar as a tool to aid with focus. Instead of asking myself, “What should I be doing with this time?,” I now ask myself, “What window of opportunity am I in? What’s something I can only do within this particular time slot?” That re-framing has made all the difference ๐Ÿ”ฐ.

This is part of my Drawing My Dream Map series. For more, follow along here as I work towards my dreams publicly and in real-time.