Formalizing a Daily Planning Habit

I’ve written about the importance of planning before, but after attending the Dallas-Fort Worth Writer’s Convention this weekend creating a habit has never seemed more important.

I’ve always been bad at it. I’ll pick up a planner and use it for a week or so and then, like all of my habits, it’ll fade away. Across keynote speakers and casual one-on-one conversations throughout the conference, it seemed that success seemed to be a matter of luck. Some person just happen to read and enjoy a writer’s work at the right time and right place. And while that seems disheartening at first, the behavioral hack behind the scenes was the same: all the writers kept constantly sending work out into the world.

Luck can be gamed. And the key is to, as Brandon Sanderson said in one of his lectures, “always be working on something else.”

That makes complete sense but is utterly beyond me without having a long-term planning system that’s solidly in place.



As soon as I get my coffee and sit down at my desk, I’ll spend just a few minutes going through my bullet journal and updating lists or reading and ranking what I need to do that day. I’ll do a bit more on Monday for the week, but even if I just open up the journal every day the habit will still count.


A) Positives
The ability to make this a part of my life will help me fill the world with writing arrows, hedging my bets to make success happen. It will also alleviate the feeling of living or dying on one proposal or pitch. This is immensely emotionally important to me. It will also help me significantly improve my craft. It will bring some amount of order to my generally chaotic life. It will help me plan for productivity experiments, and will prevent wasted down time.

It will also help me become a better person.

I think in relationships the concept of mental load is important - it almost always falls on females. I am a person who exacerbates this. I don’t plan for trips, I don’t get what I need done because I’m so disorganized, I don’t have my shit together. This forces the people around me to take up immense slack that I just assume they will carry. To both be free of that nagging feeling of constantly ignoring something in the background and to lessen the load the people I love shouldn’t have to carry is incredibly positive.

B) Obstacles
Not carrying my planner when I go on trips. Grossly overestimating time. Not having a pen on hand. Not feeling like I know it all now, when I think this will be a process of growing and adapting to what works best for me.

B-1) Workarounds
Luckily Lydia is a master of this, and I’ve already interviewed her for best practices. I think I’ll start with the basics and then add different aspects - like the 3 Ships concept or whatnot. A surprising amount of these best practices mimic what process composition writers like Jack Hart and Shani Raja describe when they talk about bringing structure to articles.

I intend to write another post on the ins and outs of this. It’s really a very foreign concept to me, but I can see it doing a lot.

Formalizing a Tally Clicking 90 Day No Alcohol Challenge

The biggest problem with my food was controlling drinking. I’ve discussed quitting – or at least severely curtailing – drinking for a long time. In An Identity Approach to Alcohol: Parts I and 2 I discuss how willpower-eroding it can be, and how counterproductive it can be in developing skills. I discussed pretty much the same thing almost 6 years ago at the very beginning of this project in Habits of Omission. I even successfully completed a 30 Day No Alcohol Challenge.

Back then, I didn’t understand the unmatting process or have the tally clicking system. Now I do.


Anytime I have an urge to drink alcohol for the next 90 days, I’ll click.

At the end of the day I’ll record the total number of urges for the day.

This is to satisfy my curiosity for the question “How many clicks does it take to remove the habit of wanting to drink alcohol?”


A) Positives
Separating out the triggers regarding drinking will let me understand how to truly control myself. I think it will help foster greater skill in things like socializing. I think it will also help me make better gains in fat loss. I think it will make me feel better overall, and will help me sleep better. It will help cement the tally clicking process as one that’s replicable and highly efficient. I’ll finally be able to have true control over a habit I just fell into. And I won’t feel like I’m using it as a crutch, either for socializing, having a good time, relaxing at the end of the day, or just feeling bored. I think it will also help me shift to becoming a more active person, perhaps even a morning person, or an outdoor person. It’s a key component of a family of behaviors that will eventually result in a massive identity shift. I think if this works, it will have massive implications in helping other people with their own lives and addiction patterns.

B) Obstacles
Boredom, especially the feeling of release triggered by drinking a glass of wine or going out to a bar, will be a big obstacle. As will the connection between celebration and drinking. I’ve conditioned myself to think that those are all one and the same. I have fear of missing out on unique drinks or experiences. I think it feels like I might have a more difficult time building a community because most of the people I have met or socialized with in the past have been when alcohol was around. I’m worried that it may be awkward.

B-1) Workarounds
I think treating this as an experiment that can always be changed is a good safety net for me. I also think the reintroduction phase of clean eating - namely the potential for having one cheat day a month - offers a psychological respite from the odd fear of never drinking again. I also know that the craving mind isn’t the same as the one that will emerge after 90 days, when the majority of urges will subside.

I think coming up with a list of alternatives for getting out of the house is important. Gong for a walk or a dip in the pool, for example, would deliver a similar hit of joy, contentment, and activity. Honing a nightly ritual might not only give me that similar feeling of release, but also become the beginnings of a sleep ritual for better sleep hygiene, something I’ve also wanted to work on.

I’ve got my spreadsheet ready, let the challenge begin!

Flawless Clean Eating: 30 Days into Tally Clicking Food

Mastering eating.

The concept never occurred to me until I ran across a thread discussing this gif:


John Stone describes how anger kicked off his transformation. It not only fueled his external change, but let him accomplish it in an almost inconceivably detailed manner. The discipline to record daily pics across so much time was levels beyond anything I had ever heard of. And looking closer, I saw that he had also recorded every meal he ate for about 6 years. 6 YEARS!!

I know that bodybuilders and athletes get strict when approaching a competition, but this…this was MASTERY, a goal so dim and far off it may as well not even exist for us mere mortals.

But somehow I’ve never felt closer to nailing eating than in the last 30 days. Here’s my data:

Urge to Eat Badly Across Time (30 Days).png


After day 22 there was a dramatic drop in my low urge days, which is exactly when my carb flu passed. The average number of urges per day has been 10. This is very interesting considering it’s nowhere near as many as I’d have thought. And little facts like that are very useful going forward and in describing this process to others.

How does this stack up with other vice removal-style changes on the same time frame?

Urge to Smoke Across Time (30 Days).png
Urge to Drink Beer Across Time (30 Days).png

Cigarette urges almost entirely disappeared within a month (though the drop off in urges occurred earlier). Conversely, urges to drink beer came up again the day I started this current project. I can’t see a pattern in these three behaviors, but I am curious to see if there is one long-term.


The story beyond the numbers is more turbulent. Carb flu was horrendous. It lasted 2 weeks, from days 9 to 22. It felt like a deep, yawning pit of exhaustion. I had a complete inability to think clearly, accompanied by weird body temperature fluctuations, light sensitivity, and incredibly low willpower. I started needing midday naps.

I couldn’t work out, and I attempted doing lighter exercises like yoga. I wanted to start recording my weight, taking pictures like John Stone, and get a starting blood test - none of which happened because I was so fuzzy headed.


Screen Shot 2019-03-20 at 12.02.14 PM.png

Despite all this, the control I exhibited was shocking, and it really showcases the benefits of what I’m calling a “craving model” of vice removal vs the traditional “action-oriented” model.

Every willpower breaking scenario came up during this time frame. I traveled to Bryan-College Station for a very emotional get together. I had a late night burger at 1 am, completely clean, with no bun and with yucca and plantain fries. I had crazy control in social situations, refusing beer and food when it was offered to me by friends. I went to my absolute willpower Kryptonite - Ninfa’s, a Mexican chain that I grew up eating. My food arrived late and I sat there, watching people eat, staring at a basket of chips and salsa without partaking as my friends sent food I couldn’t accept my way. And when my meal finally came, it came on a fried crunchy tortilla bowl.

I didn’t eat the bowl.


I watched a friend eat a delicious looking burger and fries in front of me at a bar. I ordered chicken soup that came with tons of noodles (despite not being in the description) and ate around it. At a few points I’ve ordered salads with croutons and just absentmindedly ate around them.

Lydia went on a press trip and also exhibited perfect control. Making correct food choices is, I believe, more difficult for her than me, yet at one point she slit a gyoza and only ate the insides. This occurred while having free food shoved at her from PR reps at all sides.


Amidst all the challenges, a few strategies emerged.

Steering people towards places with better food options definitely helped. For hard dates, looking up the menu to see if they’ve got good options is always wise. And when we independently had to go to a place with limited options, we both made sure to eat breakfast at some place clean beforehand. Moving my keys and phone to my other pocket was prudent so I could have easy access to my counter during problematic meals.

I also believe that not avoiding difficult situations is generally a good thing, because with food, control needs to be exhibited everywhere. Practicing this method requires wading through a lot of difficulty.


The traditional method of controlling food is summed up in “Eat X, do not eat Y.” It has horrible adherence stats. Nearly everyone fails.

The craving model is a shift over in emphasis from the actual act to the mental movements that begin the chain of events leading to bad eating.

This is clearly superior in terms of adherence. But it also unearths so many behavioral threads that aren’t always exposed. During that last 30 days, I felt inundated with ads on unhealthy eating, ads I never really noticed before. There were ads that would just pop up on Youtube, or Instagram, or Facebook, often ones you just couldn’t skip past. They’d come out of nowhere, and they’re crafted to hook you. It’s honestly a wonder there aren’t MORE obese people.

The tally clicking technique forces you to confront those cravings in your natural environment. Even though there are people who go monastic, it’s really difficult to isolate yourself so totally. And it seems to embed a probably future break in willpower if you revert to a normal atmosphere.

The craving model mechanically injects automatic self-monitoring at an incredibly high level. Lydia and I both experienced this even in sleep. We’d notice an urge in a dream, remember it, and next morning click it. My mind will at times just go alert, as though listening and asking “was that an urge or not?”

This shift from actions to monitoring urges occurred naturally, and it makes this project bizarrely effortless. I tend to become a bit irritated when I have more urges in a day, and I have to take a step back and remember there was never a moment where I thought I’d just give in to the urge itself.


This shift unveiled a number of new connections and hidden triggers.

Popcorn came up a lot because I’m so used to thinking about it as a clean, highly enjoyable snack. There was a separation between general hunger versus an urge for something non clean. I was able to recognize antagonizers and stressors - like movie theaters and bar food. Layers of un-matting included appreciating the smell of really good food (picking up glorious smelling garlic naan and driving with it back to my parents house!) versus I having the urge to eat it. Or discussing and appreciating that food could taste or look good, without the craving to consume. This happens a lot during many cooking videos (which I enjoy watching). Again, this reflects a technique where behavior change doesn’t come from environmental change.

These are connections I simply had no idea of 13 years ago, when I first started seriously trying to control my diet. I’ve counted at least 8 iterations (not including sub-iterations) on the methods I’ve tested, all of which ended either in failure or limited success.

This “Mark VIII” build is the first time we’ve ever eaten flawlessly clean for an entire month, almost absentmindedly completing a Whole 30 Challenge (minus the booze).

In a recent conversation I advised a friend on how to start the program. An important part to understand is that this build isn’t just about the tally clicking. It rests upon many previous versions. I created a once-a-week habit of grocery shopping that I still do. I use the Novelty Effect to randomize my meals. Those both provide a steady base. I’ve also rested it on top of the usual implementation intention, mental contrasting, and recording. Those, problematically, didn’t help me while living my life in general, with interruptions like travel, or eating out. This does.

It is interesting to note that the main stumbling block is the small stuff - setting up a spreadsheet or carrying my tally counter around, or even just having easy access to it. Potential version 8.1 improvements would include taking pictures as though on a “flash” diet, or giving a mental “atta boy!” after a click. Or incorporating a general gamified attitude when actions are especially difficult, like picking out croutons from a salad. Doing it with a partner or group would also add a layer of Socializing for extra adherence. I’m also looking into knitting row counter rings to increase accessibility of the tallying mechanism.

But it’s still quite effortless. I can see myself easily keeping this up for 90 days and beyond. In the future, I do want to tackle all alcohol. It’s very interesting how much of a crutch and how habitual it is. I have an urge whenever I cook. It’s a social lubricant. It’s an easy go to. There are really odd networks of what consists of a satisfying night out, of just relaxing at the end of the day.

And that idea of needing something - or of holding on - is bothersome for me.

Screen Shot 2019-03-20 at 12.09.34 PM.png

This is sort’ve the root of the craving vs action difference. For one, it’s as though people are only suffering through it by clenching - holding on to dear life until they can cheat, or until they’re done with the program. And that’s really how I felt before. I was forcing myself to do something that was doomed to fail - and it did.

In the I Ching, there’s a saying - “the beginnings hold the seed of all that is to follow”. I think that’s true. The hallmark of really well crafted self-help technique is that it just feels effortless. It’s a work of fine engineering that not only attacks the root of the problem, but works amidst the turbulence of every day life. It feels like it can be sustained forever.

That’s how I’ve felt in the last 30 days. We’ll see how the next 60 go!

2018 Year in Review

This last year has contained a huge change - moving back to the States after a decade abroad. It’s been really light on travel and publishing, but incredibly heavy on new techniques and theories which have already had a gigantic impact on this entire project. Here are the highlights:

-Formalized a flossing habit
-Added Olympic weight lifting to my exercise habit
-Experimented with habit removal by successfully removing drinking beer

Personal Records and New Highs
-Completed a 90 Day No-Beer Challenge
-started and successfully ushered a flossing habit from tiny habits all the way to a habit terminus, a habit that is totally complete
-With easy access to group meetings in the States I had my first social discharge of a habit by joining in on a group meditation.
-Took meditation to a new high by meditating throughout the entirety of a horror series (The Haunting of Hill House) and thoroughly enjoyed it despite hating horror because of the fear involved
-Solved a decades old issue - shin splints - with the help of Kelly Starrett’s mobilizations. Running is something I’ve always wanted to do, yet I’ve always stopped because of some kind of foot pain. No more!
-Passed 4 years of meditating, writing, and recording.
-Passed 3 years of consistent exercise
-Went from 35 lb dumbbell clean and presses to 55 lbs in 11 weeks (missing 3 sessions)

-Finally completed my book proposal and query letter and started pitching it to agents.
-Changed my book idea, and started working on a second proposal

Theories and Experiments
-Created a fully 3 dimensional moveable model of a full habit, something I don’t believe has ever been done before.
-Created a grand unified theory of behavioral change and self help
-Mapped the terrain of quitting
-Created a full model of the process of writing

New Techniques
-Created a Deep Work Protocol based on Cal Newport’s work
-Created and tested Structured Randomness, applying it to meal planning
-Created the ultimate guide to writing
-Figured out how to efficiently overcome the problem of limited natural progress, applying it to meditation and working out.
-Learned to gain entry into jhana through anger and anxiety
-Learned how to use noting the self to get to 4th jhana
-Threaded different types of meditations together to reach deeper states
-Experimented with and got to within a hair’s breadth of mastering sleep.

-Started reading Daniel Ingrams highly expanded second edition of Mastering the Core Teachings of the Buddha
-Learned about and practiced Mindful Scrolling, a new meditation technique
-Started reading James' Clear’s book, Atomic Habits

Attempts and Failures
-Ended a social media habit that had already gotten to super habit status
-Attempted GMB fitness
-Attempted a 30 day strict paleo challenge

Travel & New Experiences
-Traveled to Valencia
-Visited Italy (Bologna and Florence). Saw the original instruments of the old scientists as they tried to experiment and quantify temperature, gravity, and electricity, which was really exciting giving it’s exactly what I’m trying to do for self development.
-Traveled to Houston and Albuquerque
-Moved back to the States, and successfully moved into central Houston
-Hosted 5 people
-Stuck with a ban on travel, passing up trips to Greenland, Nunavut, Grenada, Barbados, and Portland
-Tried 3 different meditation groups - the Chinese Jade Dragon Temple, the local Zen center, and an insight meditation group
-Went to a writer’s group meeting
-Started pitching top tier outlets like the NYT

The techniques section has some amazing stuff. I have huge plans for the next year simply because I now finally have the methods to accomplish them. I want to:

-Quit drinking
-Remove negative self talk and totally transform my base mental code
-Master eating
-Master pitching
-Get published like a madman

That might seem like a lot, but as one wise 3 year old would say, It’s just 5 things

Happy New Year!

Habit Terminus: A (Successful) End to Flossing

Five years ago when I first started my battle for solid habits, I bought into the tacit assumption that self improvement – for whatever you’re going after – lasts forever. And since there was always something more to do and more to add, that appeared self-evident. Yet here I am at the very end of my flossing habit. I’m calling it a habit terminus.

Habit Terminus - the point at which there’s nothing to do but rinse and repeat, and even the rinsing and repeating is automatic.

Here’s the data I collected on the full habit.

Screen Shot 2018-11-12 at 10.08.39 AM.png
Screen Shot 2018-11-12 at 10.16.48 AM.png

Or if we’re being a little fancier - a 3D graph of the entire habit with SRI, habit load, and time (hopefully this displays for you)!

While I’m very happy to finally be at the end of any habit, it begs the question, how exactly do you know it’s the end? How and when can you call it?

My first automatic reaction is to resort to old school, pop science thinking. It’s been about a month. The 21-days-makes-a-habit adage originally came from Maxwell Maltz’s 1960 book, Psycho-Cybernetics (a book I’ve had on my shelf for over a decade and have yet to read), and applied to one behavior - plastic surgery patients getting used to their new faces. I’m very skeptical about these kinds of vague, hand wavy metrics, but I will return to this later in the article.

The second stand out thought is just to take the Self Report Habit Index (SRHI) to assess whether or not the full behavior - “Flossing all teeth” - is automatic.

Taking the SRHI like this was interesting. 

Screen Shot 2018-11-12 at 9.14.46 AM.png

As you can see by the chart, these 5 questions were kind’ve….weird.

  • It makes me feel weird if I do not do it

  • It would require effort not to do it

  • I would find it hard not to do

  • This task is typically “me”

  • I have been doing it for a long time

For the first 4 questions, distinguishing how I would react to flossing all teeth vs doing the previous iterations of them (20, 10, etc..) was difficult to clearly forecast. So I answered them all with “Undecided”.

The last question - “I have been doing this for a long time” - was just not true, especially in comparison with the duration of the habit itself. Hence the “disagree”.

This doesn’t really tell me much except that the SRHI needs to be modified or replaced with a better diagnostic tool to properly assess the situation.

Which leads to the third method, to focus in on the habit load rather than the habit as a whole. Rather than resorting to time or automaticity of the habit, I could sort out some sort of rudimentary scale for how unnatural or “heavy” the number of teeth flossed was - like what many doctors use for pain (“on a scale of 1-10, how painful is this”). This zoomed in approach avoids differentiating between the automatic nature of flossing 2 teeth vs flossing all of them.

This brings up another question - how many days does it take for a habit load to normalize? And how do you assess this in such a way that is efficient and not burdensome?

I’ve called this problem the Law of Limited Natural Growth - a properly created habit using BJ Fogg’s TinyHabit system, naturally grows a little, then plateaus.

One method is to raise the bar with challenges. I’ve had success with this in writing, (after a really intense NaNoWriMo) and with not eating sugar after a dietary challenge (I believe it was Body for Life). There are severe problems with this method - you’re overexerting yourself in the willpower department, and that’s never a good thing for other habits you’ve got going on. The first few times I did NaNoWriMo, I either ended up dropping habits completely or dropping them down to really low daily minimums.

The second and most successful method I’ve used to date is modulation. By that I mean slightly modifying the habit across time in one session in order to bypass boredom. This has worked particularly well for timed habits, like meditation and cardio. I have a few theories as to why this works, but I do not see it as viable with more straight forwards habits like flossing.

The method I used here was simply to raise the bar slowly. I flossed 6 teeth, then 10, 20, and then all of them. That worked, but I couldn’t tell WHEN I should up the bar.

When I was in high school I was obsessed with long distance running. The cross country coach sent out a progression to get beginners up to speed over the course of a summer, building from 1 mile to 9. Programs like Couch25k or NonetoRun do this as well, but as of yet I’ve never seen why the progression intervals work. I’ve never found if they are based on studies or just general coaching instinct. And sadly, the progression didn’t work for me at all.

Going forward with flossing I plan on changing to regular string rather than the weird flossing plastic handled things I use now, and I’m curious if that affects the habit. I’m also curious how travel affects it. I once theorized that the final test of any habit was doing it under duress like travel. 

But most importantly progress should feel effortless, and I felt I wasn’t doing things efficiently, especially when it came to upping the number of teeth per session. There were definitely points at which my habit could have broken because it felt strained to do 20 teeth versus 10. 

As I was combing through the data I decided to check the intervals in which I naturally progressed from one habit load to the next higher load. Here were the results:

6-12 teeth = 21 days
12 - 20 teeth = 15 days
20 - All teeth = 21 days

There’s that pesky 21 days! Maybe there’s something to pop science after all…

2017 (ish) Year in Review

I’ve been a little behind with this post. This has been the most turbulent year I’ve ever had, with immense amounts of travel, and a lot of setbacks. Nevertheless, the tests and experiments have yielded pure gold, techniques I can see myself using for the rest of my life. I'm including a few months of 2018 here (up until now) so i'm cheating a bit - but here are the highlights:

-Created a once-a-week habit and mapped it out using the SRHI
-Pushed meditation by successfully cross training it, adding gratitude, tantra, and metta training
-Created a social media habit

Personal Records
-Passed 4 years of daily recording
-Passed 1,000 days of daily writing
-Got back to my habits in record time (1 day off) after travel
-Improved the functional skill of my mental state through meditation

-Wrote an article in Tricycle Magazine on behavioral change and meditation. This was subsequently shared by JSTOR, and listed as Tricycle's top list of articles in 2017
-Wrote quality Quora answers that garnered hundreds of views
-Connected with one of my favorite travel writers, one of my favorite meditation instructors, and got an offer to submit to Quartz
-Moved my website over to a new site

Theories and Experiments
-Experimented with Personal Kanban and used Trello to improve my workflow
-Had a breakthrough with the editing process of writing
-Experimented and succeeded with a new method of removing a negative habit using a tally clicker
-Conducted a sleep experiment using my own sleep scale
-Found a willpower scale
-Conducted another travel sandbagging experiment
-Progressively analyzed, read, and experimented with countering moments of ego-depletion and procrastination, and then came up with a protocol that seems to have cured me of these issues even with regards to difficult tasks.
-Used Cal Newport's concept of "deep work" to come up with a deep work protocol that works like a dream.

-Read: Cal Newport's Deep Work and So Good They Can't Ignore You
-The Weekend Effect by Katrina Onstad
-Peak Performance by Stulberg and Magness
-Personal Kanban by Barry and Benson
-Tools of Titans by Timothy Ferriss
-Lots of guides on the Getting Things Done method
-A lot of details regarding cross training meditation, specifically Dr. Jeffery Martin's Finder's Course
-Culadasa's The Mind Illuminated 
-Started a Udemy course on the writing process
-Completed a Gotham Writer's course on querying agents for book publication and wrote and revised my own query letter

Attempts and Failures
-Phased out a Pantry Check and Food Recording Habit
-Attempted and failed to complete a 14-day mobility overhaul
-Attempted and failed to complete a Whole Life Challenge
-Attempted a 30 minute research and blogging session at the end of my writing to push the habit
-Attempted a skill push with planning meals
-Paused my social media habit

-Road trip through Southern France (Toulouse, Narbonnes, Nimes, Albi)
-Road trip through the Costa Brava
-Visited the Catalan town of Vic
-Visited Valencia
-Camped through the entirety of Iceland
-Visited Italy (Bologna and Florence)
-Attended my 20 year high school reunion
-Hosted 6 friends
-Attended a conference in Chicago
-Traveled through Hawaii (Honolulu, Kailua Kona, Hilo, Kawaii)
-Visited South Carolina
-Visited the States (Albuquerque and Houston) two or three times

I really thought I didn't do much this year, but looking back it really amazes me that I was able to do this much while traveling an incredible amount and being sick a record number of times (I think I got sick 4 or 5 times). Lydia and I also decided to move back to the States during this time, and went through the process of selling our stuff and moving everything (a bigger post on that later). 

Seeing what I've done despite massive interruptions makes me feel secure in the process I've developed - there is no way I could've stayed the course before. I'm also really eager to see what a year of stability would result in. Here's to 2018!