Expedition Behaviour and Reverse Pyramids ▾

Tuesday, December 3rd 2019

A Heads Up: this post is a hard-to-read jumble of thoughts. More a reference note to my future self, and/or a place where I can point friends to specific sections they may find helpful.’
(unattributed inline quotes are from Seeking Wisdom)

“We understand life backwards but live it forwards” — Kierkegaard

For the past few months I’ve been thinking on how to best think about leadership in startups…or more generally, leadership in any team-based situation where you can expect that ‘the going will get tough’. So I…


…read through The Elephant in the Brain to try and understand how and why people rationalize their behaviors. Specifically, rationalizing self-serving behaviors at the expense of group (global) well-being.

…I read Adam Grant’s Give & Take, after his podcast interview on The Knowledge Project. Hoping to learn how to better-recognize people, and their underlying behaviors.

…I read The Art of Strategy. It’s a Game Theory book which I hoped would help me learn to better design cooperative systems. That is, systems which align self-interest and other-interest without conflict between the two.

I was interested in the idea that these are not (necessarily) opposing ends of a spectrum, but can be indepenent and mutually reenforcing variables:

“This hybrid engine of self-interest and concern for others serves a much wider circle of people than can be reached by self-interest or caring alone.” — Bill Gates

I want to learn to design cooperative systems that may continue in the correct direction, even if/when bad-actors became temporarily involved.

…finally, I’ve been working through Seeking Wisdom for awhile. With the advice to read books at different speeds (per their merit), this book has been the one I’ve read most slowly, of any book. It includes a lot of relevant learning, for this.

…then, books aside, I also spent a good deal of time talking with friends, mentors, fellow-founders, and a CEO coach.

It’s been deep work on a single question.


My motivation in all of this was to: update my understanding and expectations of human self and other-oriented behaviors. With the practical purpose of designing better human systems, and choosing better leaders.

To build an unselfish company, that would teach itself…

“Be warned that if you wish, as I do, to build a society in which individuals cooperate generously and unselfishly towards a common good, you can expect little help from biological nature. Let us try to teach generosity and altruism, because we are born selfish.” — Richard Dawkins, The Selfish Gene

In the past I’ve made mistakes here. Designing systems that led to conflicts in self vs other-oriented behaviors which people exploited, choosing the wrong leaders, or both.

These mistakes hurt the team I led, and equally hurt the leaders whom I should not have put in leadership roles.

Why Deep Work on The Question

When I asked for guidance from people (friends, mentors) outside our company, they quickly put the problem in their mind’s own categories…

“We don’t like uncertainty or the unknown. We need to categorize, classify, organize, and structure the world. It simplifies life…Our brain is wired to perceive before it thinks - to use emotions before reason.” — Seeking Wisdom: From Darwin to Munger

They would either categorize to (1) fit one of their own experiences — “Oh! This is exactly like when our company…” which had little to do with our company. Or by (2) rapidly zooming-in on what they assumed root causes. Which was tough to feel, really covered things…

“We tend to be looking for the root cause of something, but in complexity, there’s no root cause.” — Jennifer Garvey Berger, of Simple Habits for Complex Times

When I looked at this guidance and asked “Could our explanation of the event help us predict future similar events?” the answer with these observers’ root cause explanations was always no.

So I couldn’t put much stock in them…they felt like a delusional sense of clarity, not reality…“Stories may be selected to prove something and may give us a delusional sense of clarity.”

Their root cause might’ve touched edges of truth, but each root cause (and each individual had decided upon a completely different root cause) was too over-simplified to be practical. — Sidenote: 💙 Chris Argyris.

Given these people had only 2nd-hand information about our company neither lead to much real learning. They (graciously) tried to help, but on the outside looking in, they always had too little context to be effective.

So I also tried asking the leaders who I had chosen in the past who didn’t work out. And they had explanations ready for me: “it’s because this…, and it’s because that…”

But in every case these explanations were externally-focused: i.e. “You didn’t do…” and “You did”…or “The team didn’t do…” and “The Team did…”

I never heard an explanation that incorporated any measure of the leaders’ own behaviors, own choices, or own responsibility. Not surprisingly, when the details were shared, team members consistently (strongly) disagreed with the leaders’ externally-focused explanations, targetting others.

Their explanations probably also touched edges of truth, but in the end these explanations were more likely self-defensive than not, to…“deny and distort reality to feel more comfortable, especially when reality threatens our self-interest.”

Somewhere, something was wrong with how I was choosing and/or managing leaders. Everyone’s guidance on this seemed to touch some truth but never wholeformed, solid truths. The feedback was a mess.

What’s worse, everyone’s advice changed over time. Before and after a leader did/didn’t work out, the same people gave completely different feedback.

‘Everything seems stupid when it fails.’ In hindsight, eveything seems obvious. But we should look at earlier decisions in the context of their own time…sometimes we have a hard time separating a true story from a false one. After an event a story is created so that the event makes sense.” — Seeking Wisdom: From Darwin to Munger

They would interview these potential leaders, alongside me. Advocate for them, judging them good leaders. Then, once failed, would forget (or downplay) their earlier advocacy…once reality was clear.

I could get plenty of post-hoc feedback. But I didn’t feel like this guidance was helping me get any better at the future.


The above was all a rambling way of saying that I couldn’t seem to learn much, by simply polling those around me for feedback. People with different interests, different backgrounds, or different contexts gave completely differenty and contradictory feedback.

But I really wanted to actually get better: at (1) choosing future leaders and (2) designing human systems for cooperation (≠ selfishness).

And I wanted to do it without lazily falling back on cynicism, and/or comfortable (but incorrect) explanations. I hoped to maintain an optimistic (but perhaps, more rationally-optimistic) view of human nature. Where the scars of bad experiences would not turn me cynical, but neither would I repeat those experiences.

“We should be careful to get out of an experience only the wisdom in it, and stop there, lest we be like the cat that sits down on a hot stove-lid. She will not sit down on a hot stove-lid again — but also she will never sit down on a cold one anymore.” — Mark Twain

I needed to truly learn something, that would improve actions and decisions in the future. But simply averaging out the conflicting poll-data wouldn’t do this.

So, the only answer was to do the work. To learn what I didn’t know that I didn’t know. So I could pick better leaders, and build better human systems.

⇢ tl;dr on outcome?

First, in the past I believe I put too much emphasis on potential leaders’ words and too little emphasis on their past actions:

“Consider people’s actual accomplishments and past behavior over a long period of time rather than first impressions. Since people leave track records in life, an individual’s paper record if often predictive of future performance and behavior.” — Seeking Wisdom: From Darwin to Munger

I repeatedly chose leaders who said they wanted to be a leader, and who said they wanted to face the challenges, etc. but who really didn’t have any ‘when the going gets tough’-type teamwork history in their past.

In hindsight, that’s become obvious.

I would then support them for quite a long time (these leaders told me as much at the time). But, eventually, after months of supporting this I would lose faith and patience in the leader. Then, faith-lost, slip into Setup to Fail Syndrome.

So things went from starting very well, to ending badly.

What I should’ve done is been more clear with myself that I was propping up a leader who shouldn’t have been there. That would’ve been better for everyone, including the leader who should not have been there.

But instead, the propping-up which was followed by an eventual lost-faith downward spiral, made things worse for all.

…again, anyway…

What follows is not a summary of what I learned. It’s just two isolated ideas that I want to write out from the process, so I can look on them later and sometimes share them with friends.

Expedition Behavior

The first is a new mental model, called Expedition Behavior. I believe this is by far, the best mental model I’ve come across to describe the responsibilities, relationships, and personalities of good leaders and teams in startups.

Most people say “it’s like a marriage” — but I now think that saying “it’s like an expedition” is probably much closer to the truth.

Neil Schulman on The Clymb wrote the best summary of Expedition Behavior I’ve found:

  • Support the Group’s Goals (i.e.; Group-Interest > Self-Interest)
  • Take Care of Yourself (i.e.; Mental/Physical Health, Performance-Shape)
  • Pitch In (i.e.; Do Your Work, Be Responsible)
  • Help Others but Don’t Do Their Work For Them (i.e.; Avoid Over-Dependence)
  • Moderate Potentially Annoying Behaviors (i.e.; duh…)
  • Admit Shortcomings and Correct Them (i.e.; No Rationalizing-Away Responsibility)
  • Support Everyone’s Growth (i.e.; Build Everyone’s Skills)
  • Be “Cow-Like” (i.e.; Don’t Get Too Emotional)
  • Relaxed Awareness (i.e.; Pay Attention, Be Responsible)
  • Be Funny (i.e.; Help Each Other Enjoy It)

Expedition Behavior is about process skills not technical skill. But it is technical skills that I/we too heavily-emphasize when choosing leaders for difficult expeditions (or startups):

“Technical skills are often emphasized at the expense of group relations, particularly in expeditions when the goal is clear and a high level of skill is required. Technical skills, while not enough to ensure safety or goal attainment, are essential and usually determine one’s assignment on an expedition, such as lead climber or medical personnel. Interestingly, it is process skills which emerge as being critical to success as time proceeds and conditions change during a trip.” — Christine M. Cashel, EdD., Group dynamics: implications for successful expeditions

I never ignored the need for leaders’ process skills. It’s just, I did not do a good job of judging them, because I judged their process skills through conversations.

On someone’s words from one (or usually, many) conversations, not by ‘actual accomplishments and past behavior over a long period of time’.

In hindsight, it’s clear that…

“…predicting who has “good” expedition behavior (or EB) can be hard. Expeditions have a way of bringing out both the best and the worst in people; and no matter how many questionnaires your team has filled out, how many pretrip meetings you’ve held, or how many years you’ve all known each other, sometimes things don’t turn out the way you expect them to.” — Dave Anderson and Molly Absolon, NOLS Expedition Planning

The Expedition Behaviour lens has been clarifying. What someone says about themselves in conversation, means very little about how they will act.

I would never appoint an expedition leader who was untested in practice. Just because they said they aspired to leadership? Just because they showed technical-expertise as a great climbers, in their local gym? Never.

But that’s exactly what I often did appointing leaders in startups.

I took an impression of their leadership, responsibility, determination, and other process skills in a conversation about what they thought they wanted to do.

Then I sent our expedition into the wild, with an untested leader at its head. Small wonder it often went poorly.

It’s when the ‘going gets tough’, when the weather turns, when the packs get heavy, when leaders are most needed and untested leaders are finally tested. Unfortunately it’s here, when it’s getting hard, that rationalizations often replace responsibility and leadership in practice, crumbles:

“Poor expedition behavior is a breakdown in human relations caused by selfishness, rationalization, ignorance of personal faults, dodging blame or responsibility, physical weakness, and in extreme cases, not being able to risk one’s own survival to insure that of a companion.” — Paul Petzoldt founder, National Outdoor Leadership School

Because it will be tough:

“…if everyone on an expedition felt as if he or she was doing 110 percent of the work, each was probably doing just enough. Expeditions require a lot of effort. There are logistical chores, long hard days moving from one camp to another, technical obstacles to overcome, camp tasks to perform, and sheer emotional endurance involved in going on a wilderness trip of any length of time.” — Dave Anderson and Molly Absolon, NOLS Expedition Planning

What I need to do as a CEO, is test for this prior to setting out on any expedition. Prior to choosing any leader. To verify process skills in practice rather than in conversation. Never to be satisfied with evidence of technical skills and only aspirations, for process skills. Instead, hard evidence of both in tough, team-based (not solo) situations.

I (think) I better understand this now. So, I hope I can choose (and test for) better leaders on both technical and process skill.

⇢ Next section is a mostly-unrelated thought.

Reverse Pyramids

The second idea is reverse pyramids.

Let’s start with normal pyramids. Those with the pointy-end up. The ones we are all familiar with. It seems we all share a mental model of leadership and hierarchy in organizations that looks something like this:

Typical Organization Pyramid

It’s pervasive and universal. It’s the common way we think and talk about organizations. In practice, a real pyramid (from 1917) might look like:

Organization Pyramid By Tabulating Machine Co., December 1917; Picture by Marcin Wichary - File:Tabulating Machine Co org chart.mw.jpg, CC BY 2.5

The problem is I think these pyramids are upside down. I think the pointy-end of the pyramid should be facing down, not up.

It’s a subtle distinction — but I think it’s important.

I feel like I’ve seen many would-be leaders who seem to view leadership from the perspective of ‘moving up the ladder.’ Who seem to think of it as gaining power, influence, freedom, …or as being recognized (and rewarded) for contributions on ‘lower-rungs’ and rising above their peers, etc.

It’s my perceptions of their actions, and perception of some entitlement. I don’t know that anyone would actually verbalize this. But…

When people think of leadership as ‘moving up’ the pyramid I think this mental model really hurts everyone including the would-be leader. It gives them the wrong expectations, and when reality hits it hurts.

I think reality looks a lot more like this:

Leadership PyramidIf my bad drawing is confusing — leaders have more people standing on their shoulders, as they take on larger leadership roles. It’s a pyramid, but it’s a reverse human pyramid, because leadership is heavy.

Leaders do not gain more power, they accept more responsibility. It’s not that a leader is ‘the best among her peers’ and therefore merit moves her up. It’s a completly different paradigm.

It’s a function of impact (for good or bad), and responsibility. You become a leader because you choose more responsibility for others, and move down the pyramid, putting more weight on your shoulders.

Phil LibinFrom How and Why to Start A Startup - Sam Altman & Dustin Moskovitz

So flip the pyramid upside down to get a better mental-model. It may be less glamorous to think of but it’s more real. It’s a more true reflection of the relationship between impact and responsibility in leadership.

It’s a function of impact (for good or bad), and responsibility. Like Ben said, ‘with great power (or impact) comes great responsibility’.

In the future I hope to do what I can to better-test leaders. I hope my expedition partners see pyramids with the pointy-end down.

Determination Models

Sunday, October 6th 2019

I lack (but I would like to find) a relatively objective mental model for thinking about determination in practice. This post is an RFP for such a framework. I am hoping that someone may be able to point me in the right direction to gain one (or ideally, several) practical mental-models on determination.

I hope to use this framework when hiring new team members (as a pre-hire test/assesment), or when training existing team members (as a framework to aide coaching, and/or a framework they may adopt in self-directed learning). Or simply anywhere the topic of determination comes up, and someone wants some practical help to increase it.

I seem to be very determined. ‘Determined’ is the always among the first word friends, fellow-founders, investors,coworkers, etc. will use to describe me, pretty much without exception. For all the good and bad about my character, it’s probably fair to say determination is in the ‘pros’ column.

However I have never successfully translated my own determination into either (1) evaluating another person’s determination (i.e. in a job interview) or (2) helping lead another person to cultivate and grow their own determination (i.e. in coaching, leadership, management).

I have tried both (1) and (2) many times but always failed.

I hope to change that. If you can help point me in the right direction, please do. 😊

What is a ‘Framework’?

Here, by Framework I mean a set of research-based practices that someone may practically act upon. Ideally a structured practice, which is (at least somewhat) objectively-observable. A Mental-Model would be a lens through which to think about something, but not necessarily a practical guide.

Some examples of practical frameworks in other areas:

These are just off the top of my head. Each of the frameworks or mental-models above are ones that have come up in my life in the past week or so, so are just top-of-mind. Most of them are well-researched (except NVC).

They work, and they are practical. The mental models help you think better and the frameworks describe a deliberate practice to make progress in real life (while “deliberate practice” is, itself, a mental-model - see how that’s useful?).

In leadership I want to find a framework (or at least, a mental-model) to:

  • (1) evaluate determination in someone (i.e. in a job interview); or
  • (2) help guide someone to cultivate determination (i.e. coaching).

I know of no such framework or mental-model for determination. 😕😢 I would really like to find one (or better yet, several). I know about grit in psychology but only as a post-hoc measure, not in terms of a proactive framework.

I hope you can point me in a good direction.

Self-Deception in Self-Evaluation

First, an aside…

Finding relatively objectively-observable frameworks seems to be particularly important when it comes to determination. Objectively-observable rather than say, basing things on someone’s self-evaluation: i.e. ‘how determined do you think you are?’ or ‘in what situation do you think you showed most determination?’.

This is because most people (or more specifically, most people’s ego) seem to have an immunity to reality, when it comes to determination. Rationalizations conver their self-evaluations into, really, just self-deceptions.

When most people faced with tough challenges give up, avoiding the pain and discomfort the challenge brings, they will ‘rationalize it away’ to keep their ego intact. They avoid both the challenge, and the defeat.

Determination Flow

And they believe their rationalizations (at least, consciously). Even when these rationalizations contradict the beliefs and values they say they have, they’ll jiu-jitsu their reasoning in strange acrobatics until they have rationalizations that seem at least somewhat justifyable, to avoid the challenge (its pain, discomfort).

“I have seen CEOs try to cope with the stress by drinking heavily, checking out, and even quitting. In each case, the CEO has a marvelous rationalization why it was OK for him to punk out or quit, but none them will ever be great CEOs. Great CEOs face the pain.” ⇢ from Ben Horowitz, What’s The Most Difficult CEO Skill? Managing Your Own Psychology.

The lengths people go to with these rationalizations…anyway…

edit: it’s also important to be clear that we’re talking about rationalizations here, which are intellectually dishonest. One friend took issue with the lack of room for intellectually honest reasons.

Parsing the two is extremely difficult, but typically when faced with uncomfortable experiences I think people tend to have far more rationaliations than reasons (I’d love to know a mental model to help parse these, too).

Rationalizations preserve ego by concealing (or at least, trying to…) the gap between a person’s:

  • (1) Espoused Theory of Action (what they say about themselves); and
  • (2) Theory-in-use (what they actually do; despite what they say)

(⇢ see this for summary on Chris Argyris’ work: or others on Action Science and Double Loop Learning)

I mention this because when it comes to determination, at least in my experience, this gap often seems very large for most people. People think they are determined, but they don’t act that way…yet when they don’t act that way, they fall-back on ‘rationalizing-away’ the need to.

It’s a generalization not a rule, but at least in my own experience seems to be majority-accurate.

(this poor ability to self-evaluate determination is why I made a point of mentioning that it is others who evaluate me as determined earlier, rather than evaluating myself that way)…

And since I hope to find a Determination Framework or mental-model for leadership purposes, in order to…

  • (1) evaluate determination in someone (i.e. in a job interview); or
  • (2) help guide someone to cultivate determination (i.e. coaching)

…any useful framework will therefore need to help make someone’s Theory-in-use (what they actually do) apparent and relatively objective to both myself and to the other person (no more ‘rationalize-away’).

If the framework only dismantles rationalizations ‘after the fact’ once determination has already failed and rationalizations have taken its place, it will not be very useful in leadership.

The rationalizations themselves, are not real. Kill one and another will take its place like a game of whack-a-mole. So as a leader I really want a framework that will dig into the root. To help someone (and help me) objectively see and cultivate their determination in an intellecutally-honest way before it’s too late.

To help reach double-loop learning in determination.

Known Frameworks (to me)

There are a few semi-related frameworks I already know about. Most are well-researched. All have been very effective for me personally in my own growth, but have been relatively less effective in leadership.

Action Science

I’ve mentioned the Action Science framework a few times above. It’s a set of practices developed mostly by Chris Argyris and Donald Schön.

It’s a bit too big to summarize here. You can maybe read this link.

For our purposes here let’s say that Action Science is a set of tools which help to dig beyond an Espoused Theory (what someone say about themselves) and into a Theory-in-use (what they actually do).

It’s a great tool for leaders and organizations. Like, really great. However it has not been particularly helpful in aiding determination.

It is somewhat helpful because if you’re going to play whack-a-mole exposing rationalizations, at least Action Science is a good way to do it.

However I’m not sure it will help me: (1) evaluate determination (i.e. in a job interview); (2) cultivate determination (i.e. as a coach).

Responsability Process

Christopher Avery describes the Responsability Process mental-model as a series of progressively-mature mindsets on responsability. He’s likely expanding on Andy Grove‘s similar responsability framework in High Output Management.

Responsability Process

In this sense ‘responsibility’ and ‘determination’ are pretty much the same thing. The responsible person here will not move down and to the left on the ladder away from responsibility, by creating rationalizations that blame others or blame circumstace, to talk themselves out of acting in a determined way.

It works by using cognitive reframing to recognize your rationalizations for what they are, then reframe the thought into something healthier (i.e. reframe your way from denial ⇢ through to responsability).

I (personally) love this mental-model and Avery gives some advice on turning the mental-model into practical Framework in real life. It’s great. Like, really great. Implementing this type of reframed thinking leads to a better life (at least, according to me). It’s that good.

But I have not found it that helpful as a leader to:

  • (1) evaluate determination (i.e. in an interview)

It’s helpful for basics, like watching-out for someone who ‘blames others’ in an interview. You can catch the blame-game easily, when evaluating someone. However the absense of blaming others is not far enough up the Responsibility ladder to really demonstrate a person’s determination.

Evaluating the higher-rungs of the ladder via conversation (i.e. in an interview) I have found to be much more difficult than evaluating the lower-rungs (which is fairly easy).

Though it has been somewhat helpful in:

  • (2) cultivating determination (i.e. as a coach)

…but on #2, only somewhat. I find it extremely effective personally, but it does not seem to work well when given to others as Avery himself points out. This tool only works with deep buy-in from the practitioner, which makes it somewhat less effective as a coaching tool for leaders.

It can work sometimes, but only in those cases where the person you are coaching is already intrinsically bought-in to the process. In other words, it works when self-directed. You can recommend the process to someone, but you cannot do much more than that.

Edit: Avery’s shared the genesis of his ideas with me on Twitter (see below). He and Grove share some common ideas but seem to have arrived at them independently. Thanks to Avery for sharing ☺️

Challenge vs. Threat Response

The Threat Response ⇢ to ⇢ Challenge Response Framework is also a type of Cognitive Reframing. For more you can see Kelly McGonigal’s work.

Where in Avery’s Framework you negative views of responsability and shift them to a responsible mindset, in McGonigal’s you take a feeling of stress and threat and shift it to a feeling of growth-inducing challenge.

Both the responsibility to view challenges positively (Avery), and the conversion of negative-stress into viewing challenges as opportunities for growth, are helpful and practical frameworks in building determination.

This model has been the most helpful to me in (1) evaluating (i.e. in a job interview). However asking someone to change how they think hasn’t been very practical to (2) cultivate determination (i.e. as a coach).

Sure, the framework works. But it only works if the person actually does it. Suggesting the model in 1-1’s with team members typically isn’t very effective, to lead to actual execution. Someone must adopt and deeply apply-themselves to this process, independently.

Her book is good if you’re interested in the science.


When it comes to evaluating determination (i.e. in a job interview) no tool has really been helpful. When it comes to cultivating determination (i.e. as a coach) some can kind-of, sort-of help but only to the extent they pick-apart and dismantle rationalizations to expose them for what they are.

But…by the time you’re dismantling rationalizations, playing rationalization whack-a-mole, it’s often already too late. Determination has failed, and the time to either evaulate for it or to cultivate it as a leader has already past. In other words, you have failed as a leader, leading to a failure in determination.

Frameworks like Action Science can be used proactively to deeply engage with root causes at a level that most teams never achieve. It’s very powerful. However, though it can bring great clarity to just about anything, it does not touch on the emotional and human aspects of determination.

You could use Action Science to objectively talk about determination with someone, but it is not really a framework for that person to cultivate their determination proactively over time. You could sort of use it this way, and perhaps it would be helpful. However I’m worried about man-with-a-hammer syndrome creeping in when applying Action Science here. There must be a better way for determination…

I hope to find a framework (or mental-model) that can be proactively effective at the level of evaluating and cultivating determination itself (not at the reactive level of dismantling rationalizations objectively,after determination has already failed).

⇢ So, any ideas? Can anyone point me in any good directions?

I wanted to write that post to ask that question of my friends…so let me know what you’ve got.

Edit (Mental-Models My Friends Have Given Me):

  • Skin-in-the-game mental model
    • This means pinpointing someone’s own, individual, unique motivation at a given challenge. What’s the growth that they (and they, uniquely, based on what they value) will gain from overcoming this challenge.
    • This (in hindsight) is an obvious model to apply in coaching, on determination. There’s a few good frameworks I already have for this.
    • Motivation mental models like Autonomy, Mastery, Purpose are obviously helpful here too.
    • Thanks @Ian.
  • Paul Graham’s Anatomy of Determination is a mental-model for determination based on (1) Willfullness, (2) Discipline, and (3) Ambition. It talks about the ability to train some of these things. I’d totally forgotten this article. Thanks @Mark.

I’ve found this book. It gives a lot of answers:
On Mental Toughness

I’ll update the list if I get more.

The habit of failure is purely mental and is the mother of fear. This habit gets itself fixed on men because they lack vision. They start out to do something that reaches from A to Z. At A they fail, at B they stumble, and at C they meet with what seems to be an insuperable difficulty. They then cry “Beaten” and throw the whole task down. They have not even given themselves a chance really to fail; they have not given their vision a chance to be proved or disproved. They have simply let themselves be beaten by the natural difficulties that attend every kind of effort.
More men are beaten than fail. It is not wisdom they need or money, or brilliance, or “pull,” but just plain gristle and bone. This rude, simple, primitive power which we call “stick-to-it-iveness” is the uncrowned king of the world of endeavour. People are utterly wrong in their slant upon things. They see the successes that men have made and somehow they appear to be easy. But that is a world away from the facts. It is failure that is easy. Success is always hard. A man can fail in ease; he can succeed only by paying out all that he has and is. It is this which makes success so pitiable a thing if it be in lines that are not useful and uplifting. ⇢ Henry Ford, My Life and Work

“I’m convinced that about half of what separates successful entrepreneurs from the non-successful ones is pure perseverance.” ⇢ Steve Jobs

“[Determination] has turned out to be the most important quality in startup founders. We thought when we started Y Combinator that the most important quality would be intelligence. That’s the myth in the Valley…But as long as you’re over a certain threshold of intelligence, what matters most is determination. You’re going to hit a lot of obstacles. You can’t be the sort of person who gets demoralized easily.” ⇢ Paul Graham, What We Look for in Founders

“They have a whatever-it-takes attitude. There are some things about running a startup that are not fun. Mediocre founders try to hire people for the parts that they don’t like. Great founders just do whatever they think is in the best interest of the company, even if they’re not “passionate” about that part of the business.” ⇢ Sam Altman on Super Successful Companies

My Habits

Sunday, December 16th 2018

Hello, all - it’s time for another blog post. It seems I’ve got it in me to write a blog post perhaps once every 3-years, or so… ;)

Today I want to write about my habits.

Partly inspired by Sam Altman’s post on his own productivity, and partly because I hope some friends may offer feedback to improve the habits I have, or suggest some useful new ones.

Deliberate Practice in Daily Life

First, a bit about how these habits took form.

I’ve done some things for years — like Gettings Things Done, for example. However in the past my habits were very ad-hoc…like most people’s, I guess.

I had some good habits, but I didn’t write them down, regularly reflect on how to improve them, or deeply research new habits for areas I wanted to improve, etc…

It was all ad-hoc, until mid-last year when that changed.

This is when I did deep research (and as a result, created structured practices) for getting better sleep. They worked really, really well. Insomnia problems I’d had my whole life were completely gone, within weeks.

Because it worked so well I quickly began taking this same more thoughtful, structured, and reflective approach to other areas of my life and work.

Today I think of this way of viewing my daily habits as an implementation of Deliberate Practice in my everyday life. I’ve been living this way for maybe ~1.5-years now.

Living this way is without a doubt one of the most important, positively-impactful, high-leverage changes I’ve ever made in my life.

I hope something below may help you, too.

Table of Contents

I’ll break this up into a few sections.

First I’ll cover each habit by category with a a bit of detail. Then, I’ll put these into context of my days.

  1. Craft
  2. Health
  3. Gear
  4. Routine
  5. Done 👋



I’ve been doing Getting Things Done (GTD) for years. It’s a personal productivity system described in a book by the same name.

From the book website’s about page:

GTD enables greater performance, capacity, and innovation. It alleviates the feeling of overwhelm—instilling focus, clarity, and confidence.

In my own experience, and the experience of many people I work with (lots of us use GTD), that statement is completely true. It’s most important impact for me has been the degree to which is frees my mind for clear thought.

I’ve recommended GTD to a lot of people. Roughly half have taken me up on it, and those that have seem to love it as much as I do. It takes time to implement but is well, well worth it. It makes people less stressed, and happier.

The above is a summary of GTD’s practices. However you really have to experience the impact these practices have yourself, to get it. So get the book and give it a try, if you’re interested.

I use an app called Omnifocus on my Mac and iPhone to implement GTD, and this is how I’ve set up my projects:

Omnifocus Projects

I use a number of tags as well, but I think the only ones important to talk about here are focus, >10min, and low-energy.

The focus tags represent tasks that require 3-5 hours of focused, uninterrupted work. The others, of course, are the opposite. I’ll talk about why these are important to me in the section on my routine.

I do two things in GTD not explicitly recommended by the book.

  1. I create many ‘reflection’ tasks. These are not really “next-actions”. They are future reminders to think (or, re-think) on a specific topic.
  2. I do short reviews daily (≠ weekly). It’s more manageable, since I have a lot of tasks, and it lets me prioritize tomorrow’s work, and the end of today.
  3. I tag some large tasks as macros. This means I have not yet broken them down into next-actions. I’ll break them down later, when it’s nearing the time to actually work on them.

Moving on now from GTD, I also use an app called Toggl to track (minute-by-minute) how I use my time each workday. This started as an experiment based on Peter Drucker’s advice that: “one cannot even think of managing one’s time unless one first knows where it goes.”

The experiment was meant to last only 1-2 weeks. At the end, I’d reflect on how I’d spent my time, adjust my habits accordingly, then repeat the experiment at regular intervals of a few months.

However, I found it so useful (and so much easier than I expected) that now, I always do it. It’s not a fixed-length experiment, anymore. I expected logging my day into Toggl to be a pain, but it was not.

I also keep a note pinned to the top of my Evernote, called Thinking Out Loud. It’s a place where I can write, stream of conciousness-style, whatever I need to think-through during the day. Think and write, think and write…

At the end of each workday I empty my Thinking Out Loud note as part of inbox-zero, and so I (re)process this information at end-of-day in whatever way is required (i.e. creating GTD next-actions). Of course, I also inbox-zero my email and my Omnifocus inbox at the same time.

Lastly, I try (but sometimes fail) to manage my time according to a philosophy of Live Well, which means being thoughtful about the number of hours I work each day to maintain my productivity over time.

More than a century of studies show that long-term useful worker output is maximized near a five-day, 40-hour workweek. Productivity drops immediately upon starting overtime and continues to drop until, at approximately eight 60-hour weeks, the total work done is the same as what would have been done in eight 40-hour weeks.

The above quote is from Why Crunch Modes Doesn’t Work: Six Lessons, a study of software engineers’ productivity and total output by work-hours.

This reality has been shown to be true over and over again. We can work long hours and get more done in short bursts of 6-8 weeks at a time, but soon that increased productivity will evaporate or even reverse.

Despite this being proven true (repeatedly), some people still reject it, and we even experience guilt over it. Intuitively, it just feels wrong.


Well, from Peter Senge’s Fifth Discipline, on systems thinking:


The most powerful learning comes from direct experience. Indeed, we learn eating, crawling, walking, and communicating through direct trial and error—through taking an action and seeing the consequences of that action; then taking a new and different action. But what happens when we can no longer observe the consequences of our actions? What happens if the primary consequences of our actions are in the distant future or in a distant part of the larger system within which we operate? We each have a “learning horizon,” a breadth of vision in time and space within which we assess our effectiveness. When our actions have consequences beyond our learning horizon, it becomes impossible to learn from direct experience.

So, what does this mean? Well, I’ve spent 1-hour writing this blog post so far. If I extend that to 2-hours I’ll get more done, right? Yes, I will.

That’s a simple, direct experience that tells me working a longer amount of time produces more work output. It’s where most people’s intuition comes from.

But the accumulated, eventual consequences of long work-hours summed over a long period of time is outside our learning horizon. So, we’re just not very good at intuiting it. Our spidey-sense often malfunctions when projected onto complex systems like this.

Anyway, I’m a workaholic by nature (just ask those who know me…). So it’s actually easier for me to work longer hours than it is to restrict myself. It comes naturally, while restricting myself does not.

However, alongside some other members of our team at Phase, I’ve learned to become a lot better at this. It’s more productive (i.e. it works), because it’s not about working ‘less hard’.

From Daniel Gross at his YC Startup School talk on How to Win:

I wanna be clear…I’m not proposing you don’t work hard. In order to win, you have to work hard. I’m proposing you don’t moronically work hard, and like, not sleep. Because then, you’re gonna have to work much harder, even, to catch up.

It’s about working with higher intensity, focus, and energy. That’s what restricting my work-hours each day to what’s been proven best, allows me to do. It actually helps me work harder.

For someone naturally inclined to working long hours (and enjoying it), restricting has eventually turned each day into a full-tilt, high-energy sprint of work. The sum of those daily, high-energy sprints is greater output than the previous long-hours marathons.

So today I encourage everyone to follow Hemingway’s advice, “The important thing is to have good water in the well…and it is better to take a regular amount out than to pump the well dry and wait for it to refill.”

The overwhelming body of research is, well…correct (…duh (-_-)).

One final note is that despite everything I just said, I actually do still work long-hours, sometimes. I just try to be thoughtful about it, and exercise some control over when I make that short-term tradeoff.

I can give myself a short-term boost only a few times each year, so I want to use them wisely. It’s how I try to work both hard and smart.


I ❤ learning - my role model in this is Drew Houston, of Dropbox:

…every weekend, I would take this folding chair up to the roof with all these books I got on Amazon. I would just sit there and read all of them. I would spend the whole weekend just reading, reading, reading.

There’s a copy of Poor Charlie’s Almanac beside me as I type this, so let me inject a comment from Munger here too:

In my whole life I have known no wise people (over a broad subject matter area) who didn’t read all the time — none, zero. You’d be amazed at how much Warren reads — and how much I read. My children laugh at me. They think I’m a book with a couple of legs sticking out.

I think I probably read about as much as Drew Houston says he does, which I suspect is a whole lot less than Munger. The total # of books I read isn’t that high though, because I tend to re-read (good) books more than I read new ones.

In learning I also spend time with (and learn from) peers and mentors as well, but let me focus here on my reading and study habits here. I rambled a bit in the Productivity section, so let’s just get right to it:

Daily Review : Reading

I keep a list of the best blog posts I’ve ever read in my Omnifocus, inside a note in a recurring tasks to read at the end of each workday.

When I do this task each day I’ll either take one of those saved links and re-read it, or I’ll search out something new. It depends how I feel.

If I read something new and it’s good, I’ll add it to the re-read list for next time, so this list keeps growing.

Weekly Review : Summaries

When I read non-fiction (i.e. work) books, I do it with a printed-paper physical book rather than audiobook or PDF, and I do it with a highlighter. When done, I create bullet-point summary references of the best books.

Each Friday I review one of these summaries.

“Think Time”

After my whole workday is done, I have something I just call ‘Think Time’. Often I’ll just sit in a park alone to think, undistracted. However just as often I’ll (re)read something that helps me grow in how I think.

Usually this means a book on Stoicism (❤ Stoicism…), but right now it means reading Poor Charlie’s Almanac.


Of course, plenty of ad-hoc reading, especially on the weekends.

Fiction, Audio-Books

Every night just before (and just after) I go to bed I read fiction on audiobook, to unwind. Right now it’s The Wheel of Time.


Journaling isn’t something I’d have expected to like. However it has become a huge part of my life.

I have a few different journaling practices. Some are focused on my work, while others just focus on being a better human.

Management Journals

I keep a management journal originally inspired by this blog post. I’ve adapted the practice the blog post describes a bit. Today I keep three of these journals in a markdown editor.

One for daily-journals, one for weekly, and one for quarterly.


The daily are much the same as described in the blog post. That is, I copy the following 3-questions into my journal at the end of each workday, to reflect on the it, the we, and the I for that day.

⇢ The It
Did you execute your work? The stuff you had on your list at the start of the day? Did you do the things that were important and not just urgent? Did I choose to work on things high leverage as a manager? Did I appropriately split my time between CEO-Work Majority and Individual-Contributor Minority? Did I lead? Comprehensively understand my team’s work in detail? Help align, energize, unblock, and motivate them?

⇢ The We
Did you add value to the lives of the people you interacted with? Did they walk away with more knowledge, energy, goodwill, help, a better understanding? What’s going well and what created that? What’s challenging and what created that? What strengths and contributions do I notice in others? Did you take the opportunity to coach?

⇢ The I
How did I manage my energy and mood? Self-care like working out, eating well, and sleeping enough. How do I feel today? What’s on my mind? What did I learn? What strengths did I notice in myself today? What did I improve in myself (mission, communication, etc)? What could I have done better today? Did I consciously manage my stress?


Weekly journals are different - at the beginning of each quarter I set what are sort of like personal, management, and leadership OKRs.

In my weekly journals, which I do on Mondays to reflect on the previous week before beginning the new one, I’ve got two sections.

  • In the first section I re-read the previous week’s daily management journals then summarize and reflect on that week.
  • In the second section, I reflect on my personal OKRs’ progress.


This is the same format as the weekly journal, but applied to reviewing the previous quarter’s weekly journals.

Life Journals

I use the 5-minute Journal format and also the Morning Pages, both of which are Tim Ferris recommendations.

I use to do both every morning, but now I choose one or the other each day. I write both of these longhand, with a physical notebook.

5-Minute Journal

The 5-minute journal is actually two, short journals: one in the morning, and another in the evening. Both take only a few minutes each.

The morning journal has three sections:

  1. I’m Greatful for… (write 3-things…)
  2. What Would Make Today Great?
  3. Daily Affirmation; I am…

And the evening journal:

  1. Three Amazing Things that Happened Today…
  2. How Could I Have Made Today Better?

5 Minute Journal

Morning Pages

Morning Pages are:

…three pages of longhand, stream of consciousness writing, ideally done first thing in the morning.

I was sceptical of Morning Pages, but have found them hugely helpful. It calms my Monkey Mind to help me focus each day.

I choose to do Morning Pages rather than the 5-Minute Journal maybe, once a week or so, based on how loud my Monkey Mind is that week.



I use to have lots of trouble with sleep. It’d take me hours to fall asleep, and once I did I’d still wake up several times a night. Now though, after years, I’ve solved it.

And it’s great.

Similar to how working long-hours is counter-productive (read: it’s dumb), allowing your sleep to suffer in quantity or quality is at least as bad, or even worse:

…knowledge workers [are] exquisitely sensitive to even minor sleep loss. Research by the US military has shown that losing just one hour of sleep per night for a week will cause a level of cognitive degradation equivalent to a .10 blood alcohol level. Worse: most people who’ve fallen into this state typically have no idea of just how impaired they are. It’s only when you look at the dramatically lower quality of their output that it shows up.

We’re just as bad at intuiting the damage poor sleep has on our productivity (let alone, health) as we are on extended periods of long work-hours.

What’s worst is just how unaware we are how much our sleep quality suffers due to normal, modern living with things like light pollution, for example.

It’s something worth investing into, with time and learning. I have solved this for myself, and my life’s much better as a result.

If you want to learn more someone like Shawn Stevenson gives good intros on YouTube, and has a good book where the majority (though not all) of what he recommends has good backing.

I hope some of what’s below might help you too.

Device Curfew

Your devices’ (phone, laptop, etc.) blue lights are bad for your sleep, and probably bad for your health generally.

Blue Light

The best thing I do is my device curfew where I just stop using my devices around 8:00pm. I do some other things too, though.

I use Night Shift on my Mac and Phone to dim blue light in the evenings. It’s not powerful enough, though. So I use this superdim hack too, on my iPhone.

I’ve got a pair of bluelight blocking glasses which I use while on my computer during the day.

What I really want (but don’t have yet) are low bluelight lightbulbs for my bedroom. They should allow me to read before bed, with the light turned on. Right now I’m squinting at my books in a dark room.

Magnesium Oil

Now, this is awesome.

Magnesium Oil is something you can spray anywhere you feel sore - or just, wherever - right before bed. It relaxes you and generally helps sleep::

Magnesium regulates both neurotransmitters and melatonin. Neurotransmitters relay messages between your brain and your nervous system, and your melatonin levels control your sleep-wake cycles. Researchers have found that melatonin and magnesium levels correlate in the body. Those with depleted levels experience poorer sleep, and vice versa. Based on these findings, researchers concluded that, like melatonin, magnesium is tied to your circadian rhythms.

Magnesium Oil

It really helps me a lot. I’ve given it to a few people and they’ve told me it really helps them, too. One $20 bottle will probably last you 6-12 months.

That’s maybe 5¢ per night for better sleep? I definitely think it’s worth it.

Learning to Sleep on my Back

I’ve learned to sleep on my back with an ergonomic pillow that has been a big help for my neck pain.

LED Light

This was something recommended by Sam Altman in his post on productivity . Specifically he said:

I use a full spectrum LED light most mornings for about 10-15 minutes while I catch up on email. It’s great—if you try nothing else in here, this is the thing I’d try. It’s a ridiculous gain for me.

So I got one too and yup, it’s great. I turn it on each morning during my journaling right after waking up.


It energizes me right at the beginning of the day, then in turn helps set consistent circadian rythms for that night’s sleep.

I’m using this one and like it a lot.


I use something called a ChiliPad to cool my bed. My wife thinks it’s dumb, but I really like it. I do wish it had more powerful cooling, though (Taiwan is hot).

Apple Cider Vinegar, Honey

I’m not sure if this works or not, but I enjoy the ritual of making a cup before bed. Grab a cup of water, add 2-3 tablespoons apple cider vinegar, then mix with 1 tablespoon raw honey.

Many swear by it. Google it, you’ll see.

Audiobooks, Fiction @ Night

I read fiction at night via audiobook, to relax. I listen to these audiobooks while falling asleep and use something called Cozyphones to comfortably wear headphones to bed.

What’s very nice is that the Cozyphones for exercise are cool enough to wear to bed in a hot country like Taiwan.


Food ± Supplements

Unhealthy eating has for most of my life, been my worst habit. So sometime last year I decided to finally fix this. I spent some weekends learning what I needed to know, then turned that knowledge into a plan for change.

My Health Plan

Below are the habits that have resulted from these changes.

Intermittent Fasting

I do intermittent fasting twice a week, for 24hrs on Tuesdays ⌿ Thursdays.

What does that mean? Well, it just means I eat my last meal on Monday evening, then don’t eat again until Tuesday evening. Same on Thursday.

I won’t try to get into the science of intermittent fasting here because it’s not fresh enough in my mind anymore. If you want to check it out, see Jason Fung. He’s a Canadian doctor who uses intermittent fasting to help reverse diabetes.

I’d really like to try longer fasts a la Evernote’s Phil Libin-style, but I haven’t yet prioritized the time to try it.


Most of my meals today are in the form of the unfortunately named, but otherwise awesome, Huel powdered food. There’s a signal vs. noise problem with this type of powered food…so people sometimes mistunderstand it.

Things like Soylent, though well-known, are actually not that great. The best summaries I’ve found were this one and this one. I chose Huel because it was healthy, but cheap:

Huel is transparent about the fact that they use conventionally grown, as opposed to organic, ingredients. The primary reason why the company decided to go the conventional route is cost. Huel’s goal is to deliver a nutritious meal at a low price. By using only organic ingredients, Huel would have to charge more for their product. I appreciate that not everyone can afford pasture-raised meats and organic produce and, thus, consider Huel an excellent alternative. It’s also worth noting that Huel is non-GMO, even if they don’t advertise it as such.

When I first began eating Huel, for a few days I felt hungry. The amount of food I was eating was small, so my body was all “what’s up?”

But a few days in my body was all “oh, I get it…you’re just not eating crap anymore”. The amount of food now felt filling, and I started craving Huel, and sort of ‘anti-craving’ what I’d been eating before.

Huel’s great for me, and my body knows it.



I love coffee, but these days I try to stop drinking it around 2:00pm at the latest. It’s really important for sleep.

Nootrostax Smart

Nootrostax Smart is a ‘smart pill’ - it increases memory, focus, energy, etc. I really love it, though I’m still on a supply of v2, so can’t speak to v3.



I take creatine for better cognitive performance, and improving my memory. The evidence says that long-term use (i.e. years) is just fine.

I take this just before bed, since I’m taking it mostly to improve short-term memory (which your brain stores at night). I’m not sure if this timing actually helps, though.

Host Defense Immune Support

I use to get sick all the time, especially when I travelled for work.

So when I was reading Tribe of Mentors: Most Impactful Purchases of $100 or Less I got excited when I saw Host Defense recommended by Samin Nosrat:

…Host Defense MyCommunity mushroom complex is the most incredible immunity supplement I have ever taken (and I have taken a lot of them!). No matter how much I travel, how many hands I shake, or how exhausted I am, I don’t get sick as long as I take the supplement diligently.

This bunch of mushrooms turns you into Bruce Wilis in Unbreakable. I just don’t get sick anymore, whereas I use to be sick 1-2 times/month.

Host Defense


It’s unclear if multivitamins really help, but I fall into the “why not” camp with this. I’ve got a subscription for Naturelo Whole Food Multivitamin for Men.


Mental Health

While I think journaling and Stoicism are actually the biggest positive contributions to my mental health, meditation is important too.

I use an app called Headspace for guided meditation most mornings, which I do after journaling. I sometimes use it during the day too if I need to do something like increase my focus, or de-stress for a quick 3min.


Consistent exercise is a problem for me. I enjoy going to the gym, but I travel so often for work that any gym schedule is quickly disrupted.

So for the past few months I’ve been trying a new approach: zero-equipment HIIT workouts, that I can do anywhere. Right now this means the 7-minute workout in the mornings with the accompanying app, though I may try others soon.

I have yet to see if this’ll hold up when I travel.


Work Station

Work station is a fancy way to say, the stuff I carry in my backpack to use my computer. I use a Roost Stand with external keyboard and mouse to bring my laptop up to eye level without craning my neck.

Roost Stand

It’s great. I work on my computer a lot (obviously), and bringing it up to eye level has helped ease some chronic neck pain.

I’ve got reading and writing stands on my desk at home for the same reason. Overcome the nerd neck 🚀.


Except for my sweatpants (which I soon hope to replace) my clothes don’t look much different from anyone else’s, but they are.

As we grow up we switch from comfortable to uncomfortable clothes, and from functional to un-functional clothes. I think it’s really, really dumb.

So I try to walk the line wearing clothes that look acceptably-adult, while secretly being more comfortable and functional than the rest of you fools (kidding…).


Taiwan is hot, and so are a lot of the countries I travel to. Until recently though, the only shoes I could find to deal with that were sneakers, which I didn’t want to wear in some work contexts.

But neither did I want to travel with two pairs of shoes, constantly swapping sneakers for work shoes and vice versa.

I finally found the answer in Cole Haan stitchlite. These are perforated, knit-shoes that I actually find even more cooling than sneakers, and they look good too.


I’ve also got a pair of Xpand no-tie elastic laces in my shoes, because why would I want to sit down every time I want to put my shoes on?

They’re no-tie, elastic laces for adults.

Merino Wool

I’ve been slowly migrating all my clothing to Merino Wool. It’s basically super-fabric, from a New Zealand super-sheep.

It keeps you warm when it’s cold. It keeps you cool when it’s hot. It’s lightweight, strong, and it’s comfortable. It’s anti-bacterial, so when you’re traveling you don’t have to worry as much about not being able to wash - it won’t stink.


Something I haven’t yet done but really want to is: great pants. Pants that look like jeans, but are actually cool, lightweight, sweatpants-y pants (i.e. comfortable).

It’s the only remaining the part of my clothing where I’m full-on little kid (i.e. comfort, function ≠ style. Now, I’m usually just in standard sweatpants.

I have my plan, though. I just have to choose which to buy. There are some like Public Rec, Western Rise, Oliver’s, Thunderbolt, and plenty of others.

Once I’ve got the money, I’ll get a few pairs.


Ok - now, let’s put this all into the context of a day.

My miBand starts a vibrating alarm at 6:15am each morning, but I’m usually already awake. First thing, I grab my phone for 7-Minute Exercise. Once done I sit down at my desk for ~10min to meditate with Headspace.

Then I switch on my LED and start my 5-Minute or Morning Pages journal. Finished my journals, then grab my Naturelo, Nootrostax, and Host Defense then mix a bottle of Huel to drink during my walk to a cafe.


I’ll arrive at a cafe around 7:30am for what I call my Focus Time. This is where I focus on one block of work which needs my undivided attention for ~4 hours, in keeping with Peter Drucker’s advice that:

The effective executive therefore knows that he has to consoidate his discretionary time. He knows that he needs large chunks of time and that small driblets are no time at all. Even one quarter of the working day, if consolidated in large time units, is usually enough to get the important things done. But even three quarters of the working day are useless if they are only available as fifteen minutes here or half an hour there.

Tasks for this Focus Time are tagged focus in my GTD, which I prioritized for today’s work yesterday, so when I sit down with my coffee I can get right to work.

I’ll sometimes use whitenoise or a single-song on repeat for hours during this Focus Time — blocking my Focus Time each morning like this is one of the most important habits I have as a CEO.

A few hours in I have standup calls on Zoom with my team, but these only last a few minutes, then I’m back to Focus Time.

Somewhere around noon or 1pm, it’s time to switch. I mix another bottle of Huel to drink while walking to my next work-spot, usually our office. The rest of my day is then spent quickly context-switching between small tasks, or in meetings.

Oh, and I’m tracking what I do on Toggl, since arriving at the morning cafe. I’m also setting up that backpack workstation, everywhere I go.

By late afternoon I’ve (hopefully) accomplished everything I prioritized in GTD for today, and it’s time for my GTD Review (which I do daily).

I inbox-zero my Omnifocus inbox, email inbox, and my Evernote ‘Thinking Out Loud’ note which by now has filled up with the day’s stream-of-conciousness thoughts. Then, I read (or re-read) something useful for my learning.

I breifly review and edit every task in my Omnifocus, and double-check that I’ve correctly logged my Toggl today which lets me reflect on the day’s work accomplished.

Finally, I prioritize my work in GTD for the following day.

If it’s Friday I’ll do a more thorough review, which includes things like breaking down macro-tagged tasks in GTD to next-actions, if I’ll try to complete those macro tasks in the following week.

When that’s all done I grab my markdown editor to write a Management Journal for the day where I reflect on the We, the It, and the I.

With that all done, now my work day’s over.

So it’s time for Think Time, which can mean a long walk, or sitting alone in a park, to just think or to (re)listen to a Stoic audiobook.

There’s then a variable few evening-hours here where I’ll usually either do something with my wife, or see some of my friends.


When I’m home for the night I’ll watch something on my computer if it’s early, then switch to reading as it gets later.

I’ll take my creatine, mix my apple cider vinegar and honey, have a shower, get my magnesium oil, then get to bed with cozyphones, a sleep mask, and a good audiobook.

Done 👋

And, that’s all ;)

It took me some time to develop these habits, however I’ve been adhering to most of them for quite awhile now, and my life’s much the better for it.

I hope a thing or two above may be useful for you as well, and would love to know how you think I could make my own habits better.