How to Organize Your Life With an Ever-Evolving System

The sixth biggest regret of my generally charmed life is that I didn’t start organizing my life I was 29.94 years old:

I could have prioritized, invested, and preserved my time so much better had I had a better system. Maybe then I’d be doing something more impressive than writing this post. Or at least I’d be doing so in a nicer apartment.

Oh well. Better late than never.

Getting started with organizing my life was one of my best moves in recent memory.

I’m also glad I didn’t clone some productivity guru’s system. Because I strongly believe everyone needs to develop their own. So rather than listen to me try to tell you how to create a system for organizing your life, see if you can take some inspiration from my system’s evolutionary tale.

Step 1: Start crudely.

My life-organizing system’s first evolutionary step was like that our ancient ancestor, the Tiktaalik:

It was crude, adventurous, and didn’t take much brainpower. 

But unlike the Tiktaalik, my first step was inspired by a podcast. A movie director named Robert Rodriguez told Tim Ferriss that he keeps a log of everything he does every single day.

Inspired by all the benefits Rodriguez reaped from his practice, I gave it a try. 

Here’s what I wrote on that momentous day of September 23, 2015:

Jotting this down took me, what, maybe five minutes in total?

Not a lot.

That cost was easily offset by the immediate benefits I felt:

• More mindful with my time. Just like a calorie counting app like My Fitness Pal does for food, writing down everything I did made me aware of how I consumed my time.
• Mental unload. Writing down everything I did offloaded the pieces from my messy, unreliable brain and onto something else I could better wrap my head around.

This “lifelogging” led to other benefits I wrote and video-ed about separately.

Step 2: Add some directions.

Once I got used to writing what I did, the natural next step of my life-organization system’s evolution was to note down what I wanted to do.

So I put to-do lists atop my daily logs.

I’d start my day with a few to-dos, then tack on others as they came to mind. And when I didn’t get through everything, I copy-pasted the leftovers to the next day.

This simple evolutionary step had multiple benefits:

• Wasting less of my limited brainpower remembering my to-dos.
• Motivation to get dopamine-hit rewards from checking off items.
• Ability to break vague objectives into multiple actions, each with their own to-do.
• A more realistic idea of how much I could accomplish in a day.

Equally important?

My system remained simple. So I had no trouble keeping at it.

Step 3: Keep track of all your tasks.

Not all my to-dos needed to be done that day or the next, so soon came the next evolutionary step of my system for structuring my life:

Creating a separate list of future to-dos.

Guess what happened to that list?

Yeah. It grew out of hand faster than Australia’s population of invasive cane toads:

Come to think of it, this analogy gives new meaning to Brian Tracy’s famous Eat That Frog productivity advice. There was no way I could eat all my frogs at once. But I didn’t want to exterminate them all, either. I had to corral them.

Step 4: Order and prioritize.

To regain some control of my rapidly expanding to-do list’s population, I sorted it into sub-lists:

• To do this week
• To do next week
• To do this month
• To do next month
• To do eventually
• Etcetera

The big benefit of this step?

It forced me to prioritize.

I knew deep inside that anything on the “To do eventually” list was like world peace…

…a nice idea, but realistically never going to happen. If I wanted something done, I had to put it on a to-do list with a date attached.

While this step may seem like a small step to you, it was a giant leap for Chris-kind. It was the evolutionary equivalent of the Tiktaalik’s sprouting a lateral frontal pole in its brain. All of a sudden, more than structuring my days, I began to structure my weeks and months.

Step 5: Assess your performance.

With my rudimentary life organization system, I felt like I’d installed guide walls inside the Plinko board of my life.

But was I moving slowly and not hitting any rewarding targets.

Why?

Because I fell into the habit of making cheap to-dos for myself. Checking them off gave me a temporary sense of satisfaction, so I lined them up and knocked them down like a frat boy doing shots at a dingy bar during happy hour:

• “Take out the trash”? Check!
• “Respond to Mom’s text message”? Done-zo!
• “Draft a new blog post.” Ugh…
• …oh look! Here’s another, “Change the font size on my about page.” Bam! Way to go me!

When I looked back at the damage I’d done, I didn’t feel particularly proud of myself. I could barely remember what happened.

But I had written it all down! So nothing was lost as a hazy memory. And this led to the next great evolutionary jump for my life structuring system:

Weekly reviews.

Every Sunday evening, I started reviewing the ups and downs of my past week and setting up the following one.

Seeing all the cheap little to-dos I’d slammed down gave me zero satisfaction. What made me feel like a million bucks was if I’d done:

• Big things: The type of work that builds on itself and lasts like:
  • Researching and writing blog posts.
  • Family gatherings.
  • Meaningful progress on projects.

And,

• Interesting thing: Stuff that spices up my life story and opens the door for serendipity like:
  • Making social connections
  • Taking a class on something new.
  • Visiting a different part of town, for example.

I felt like a prehistoric herbivore who accidentally took a bite of its buddy’s flesh and realized, “Oh man! This stuff’s got way more bang for my bite than grass.”

Weekly reviews moved me up the food chain.

They started motivating me to go after big kills and leave little, insubstantial to-dos for later, when I’m feeling tired or hung over.

Step 6: Re-balance your structure.

As tends to be the case with speedy evolution, my move up the productivity food chain to hunt bigger, more interesting things had an unanticipated downside:

It got me working too much.

I suspect it’s because meaningful progress at my work is easier and quicker to accomplish than equally meaningful progress in my personal life. For instance, it’s easier for me to write a new blog post than make a new friend.

But, in my weekly reviews, I noticed that I felt best when I had made accomplishments in all the pillars of my life:

So I needed to balance my to-do diet.

Just as I sorted and prioritized my to-do lists by date in Step 3, I broke out each of those lists by silo. This reminded me to take care not to leave any of these pillars off my plate for too long.

Step 7: Shove in more memories.

Inspired by two great books, Storyworthy and A Million Miles in a Thousand Years, the next evolutionary step to the way I organize my life was to add another silo:

Memorable moments.

This addition serves two purposes:

1. To highlight little anecdotes that may otherwise vanish from my memory.
2. To compel me to create more of them, making my life a more interesting story.

Step 8: Zoom out.

By this point, my system that I started with the intent to save myself precious time was costing me a good amount of it.

For instance, my weekly reviews were taking about thirty minutes. And I never once looked forward to it.

But they’re no different from accounting for my expenses. They reinforce my desire to manage my time wisely and help me get a clearer idea of how to spend it next. 

This rationale led to my system’s next evolutionary step, when I asked myself:

Why stop at weekly reviews?

So I zoomed out another level, incorporating monthly reviews and plans. For these, I review my week reviews the same way I review my days for my week reviews.

Often, I’d be impressed by how much had happened—and changed—in the past thirty-odd days, especially when I invested my time in big and interesting things.

This compelled me to prioritize even larger-scale endeavors that I too often put off because they’re time-consuming and not-urgent—stuff like courses, camping trips, 30-day challenges, and new projects. Steven Covey calls these “Quadrant II” tasks in his book, The 7 Habits of Highly Effective People.

Step 9: Zoom out even further.

My monthly reviews worked so well that I zoomed out another level:

Annual reviews.

Like blood vessels look like branches, which look like rivers, my annual reviews took the same structure as my weekly and monthly reviews—just bigger in scale.

By this point, I was so zoomed out that I’d surprise myself with what I saw. I’d read of plans, books, memories, and ideas that had vanished from my memory and wouldn’t have believed had I not written the words myself.

These year reviews gave me a broader perspective, hammered home the unreliability of my memory, and compelled me to start the surprisingly rewarding tradition of writing annual letters to my future self.

Steps 10-∞: Keep evolving the way you organize your life.

It’d be fair for you to observe my life from the outside and wonder:

What good has this system Chris uses to organize his life done for him?

Whatever direction my system’s Plinko-ing me down and whatever “big” and “interesting” to-dos it’s motivating me to prioritize aren’t exactly setting the world on fire.

I warned you not to clone it, didn’t I?

My system’s far from perfect, so it still has a lot of evolving to do. But one thing’s for certain:

I’m not dooming my life organization system to extinction.

Because while I’m not setting the world on fire, I’m not running around putting out fires, either. I feel more on top of things, and in control of my time, than ever.

Most importantly, time doesn’t feel like it’s slipping through my fingers as fast as it used to.

My system is capturing those sands of time and building them into something.

It may not look like much yet, but it’s better than what it would be otherwise. And I’m optimistic for the future.

So I bet you my decade review’s going to be pretty cool.

And my 100-year review’s going to be incredible.

TL;DR: How to Evolve a System for Organizing Your Life in 10 Steps

1. Start by crudely keeping track of what you get done.
2. Add to-dos atop your tracking.
3. Keep a list of the to-dos you think of.
4. Organize your to-dos by time and priority.
5. Review what you accomplish weekly.
6. Break down your planning and review process by life pillar.
7. Include memorable moments in your tracking.
8. Plan/Review your weeks monthly.
9. Plan/Review your months yearly.
10. Continue evolving your system.

And for more of my best tips on getting your life in order, I suggest you check these out:

• The 5 Unheralded Dos and Don’ts of To-Do List Management
• Time Logging Day 1,876: A Boring Example of an Extraordinary Habit
• The 7-Step Self-Improvement Plan That Works (If You Do)
• The Personal Strategic Plan Inspired By a Harvard Business Legend