A Planner’s Take on Life Planning

Organizations: My, Myself, & I

Collaborators: Just Me

Dates: Fall 2014-Today

Foci: Living Life, A Touch of OCD, Effectiveness

The Bigger Questions

How do you think about what you want out of life? And once you know what you want, how do you get there?

What Do I Really Want?

I’ve always been an organized person.

Over time - starting at my first job - I began the process of creating the best life organization system I could. This naturally meant beginning with the end in mind - thinking on what would make me proud at the end of my life. "The 7 Habits of Highly Effective People" was a critical book in helping me figure out a process for laying out these values - I'd highly recommend it to anyone.

Any introspective process can be a painful one. Learning to sit with feelings triggered by unexpected memories required extensive time meditating and reading on how to handle living life (Pema Chodron, Meditations by Marcus Aurelius, Seneca, Cicero), and many hours in therapy. I did my best to learn from people who've lived their lives and people willing to listen. Hopefully these resources can help you, as well, if you're interested in doing the same.

I've worked on my values document for years, on and off, and it's current iteration looks like this.

How Do I Get to What I Want?

Figuring out what general projects to pursue on a slightly less long-term level was not easy. I iterated through several decision-making processes - free form, algorithmic, and a mix of both - before settling on the latter.

My current process is relatively simple:

1. Identify which of my freedoms seem to be most in danger in the next 3 months

2. Free-write on why I believe this to be the case

3. Brainstorm projects that can help tackle the highest-priority problems

4. Write up project rationales and outlines for these projects

The result is a quarterly priority document that looks something like this, and a set of project briefs that look something like this.

What Do I Really Want?

Now, working on the right problem is definitely the most important aspect of doing great work. But, being sustainably efficient if how you get the most out of each week. "The 7 Habits" was, again, a wonderful book for this. Planning out your week in broad strokes is a phenomenal habit.

I initially picked up the habit of planning everything in my calendar. However, even for someone as detailed as me, I was a little overzealous.

Toning my process down, I switched to organizing my weeks in broad strokes. I made it a point to not be distracted by anything unrelated to project work during those carved-out time periods.

If I felt like my concentration was faltering, I had the option to take care of my body (exercise, drink, stretch, eat, etc.) or meditate until I felt like working again. Meditation truly is a superpower - Zat Rana describes it best:

“People often conceptualize meditation as a neutral activity. You sit still. You do nothing. But when meditation is lived, it’s actually offensive. It’s fearless. It allows you to ignore almost everything, except when it makes sense for you to act, and then, when you do act, you strike with the conviction of thunder. That thunder is, by definition, improbable in where it strikes. It’s a force of nature, and so you, too, become a force of nature - one that doesn’t break in the face of chance, but one that carves its own destiny in between the opportune gaps that chance leaves open.”

Perhaps unsurprisingly, figuring out how to relax was my greatest obstacle. I wrote guides for myself, tried all sorts of reward systems, but at the end of the day, I realized I just needed to allow myself to feel like I was worthy of and deserved to be treated well.

Sometimes, that’s a hard lesson to learn. But, if Rick and Morty can do it, so can I.

My current system is, again, relatively simple. For every hour of effective, focused, carved-out time, I gain 15 minutes of "Reactive-Mode" time. I characterize time as either pro-active (planned, focused, and deliberate) and reactive (do what you want, spontaneous, and fun-seeking). Both are necessary for different parts of your brain (the higher functioning part and the lizard brain part), and keeping both happy build a sustainable foundation for good mental health.

So, this is how I like to operate. I'd be happy if you stole some of these ideas - none of them are originally mine anyway! And if what works for me works for you, it'll have made writing this out all worth it.