After several weeks of consistency, I have unfortunately missed my Monday commitment to write weekly… I do, however, have some juicy updates & topics for this week, and hope to regain my cadence posthaste! This issue is specifically focused on habits and intention setting.

How is wellbeing implemented? (Research)

A lot of my reading and conversations over the past week were focused on goals, habits, and routines. This mirrors a lot of my qualitative and quantitative research; when asking individuals about their goals, that’s usually tied to how they plan to achieve them (habits), and how those efforts will be integrated into their day-to-day (routines).

Some of the following - as will be elaborated in the ‘Think’ section - is really an outline for research that I have yet to conduct, i.e. needs to be validated by talking to individuals with a different goal in mind.

As a refresher, my initial interviews and survey were designed to understand:

1. How people thought about wellbeing

2. How they rated their personal wellbeing

3. Their thoughts on income diversification (including entrepreneurship)

4. Any patterns related to their responses and development theory

   1. Primarily from Kegan’s perspective

My findings pointed to some problems that I could address around self-actualization and how individuals set their goals (intentionality) and created habits to follow (when focusing). Prior to building out a solution, I needed to better understand the space I was playing within.

(For my avid readers, this parallels my recent work with Potential, which I’ll get into under ‘Build’).

What’s in a Goal?

At a high level, it’s easy to draw a connection between a goal that someone sets out and categories within Maslow’s Theory of Needs. I.e. a goal to lose weight can connect to physical needs, attachment needs (desire for a partner / attractiveness), self-esteem needs (perception of self), etc.

This categorization, however, doesn’t answer more pressing questions that are specific to the individual like:

1. How does the weighting between categories influence the habits and intensity with which the individual pursues that goal?

2. What will influence changes in that goal? Whether in

   1. Specifics (i.e. lose 10lbs VS 5lbs) or

   2. Entirety (i.e. lose 10lbs VS learn to swim)

3. How are goals viewed and constructed?

   1. It’s evident that “lose 10lbs” is a goal, and that you likely need multiple habits to accomplish it (eat at a caloric deficit, exercise, etc.).

   2. Many people, however, might describe a goal like “I want to eat healthier”. In reality, that is a habit, but maybe it’s a different category of goal?

      1. I.e. “I want to eat healthier” necessitates the habits of buying healthy food, cooking healthy meals, etc.

   3. When pressed, would the individual say that the above goal (eat healthier) ladders into a more permanent goal that isn’t a habit, i.e. lose 10lbs?

      1. Is there a category for ‘goals’ that are very ambiguous (i.e. “treat my body well”) that may cross multiple need categories, i.e. physical & mental health?

4. When are goals proactive VS reactive, and how does this impact their implementation?

   1. Proactive goal — You notice something about yourself that you want to improve and set out to do it. It could be driven from an interest, i.e. learn a language, by being inspired from a friend, etc.

   2. Reactive goal — You have an interaction, event, etc. that drives the creation of a new goal. This may be health-related (i.e. diabetes diagnoses), self-esteem related (i.e. comparisons via social media), etc.

   3. If someone had to guess at their ‘breakdown’ of the goals in their lives, how would they split it between the above? Is this purely about framing, i.e. you can repurpose a reactive goal into a proactive goal (and vice-versa)??

      1. I.e. You set out to learn the French language because of an admiration of French rap and wanting to explore it more. In the coming weeks, as willpower wains, you start to question how badly you really want to learn French.

      2. This may turn into a reactive goal if you already told people that you were learning it (or are learning it with friends), and don’t want to let them down, or you booked a trip to Paris and need to get to a level of proficiency, less you risk souring the trip experience.

5. What ‘kills’ a goal?

   1. When do people move on from goals? Do goals ever ‘die’, or do they just evolve — get smaller if too ambitious, change scope as you learn more from doing, etc.

   2. Is there such thing as ‘zombie goals’, i.e. ones that you hold in high regard but have not made any progress towards recently? How does this impact your self-esteem and perception of other, competing goals?

   3. What is the breakdown between active VS zombie (inactive) goals?

6. How often are these goals revisited by the individual, and re-evaluated?

   1. Is there an exercise of “this goal gave me satisfaction” that leads to pursuing new goals, or is it more a gut feel / natural transition? (I’d assume the latter)

You can see that I already regret making the above a numbered list with multiple sub-sub-bullets, and I haven’t (really) even strayed away from goals as the focus. These are all integral questions to answer, because they are central to answering “how do you help someone accomplish a goal”.

The Theory of Goal Hierarchy (Sookraj, 2024)

I added this section while tackling the section below (What’s in a Routine), realizing that it would be helpful to outline more about a hypothetical scenario, using assumptions from the above questions, that could guide future tests.

For sake of argument, let’s call it the Theory of Goal Hierarchy and say that it states the following. I’ve italicized the ones that I’m not 100% convinced on:

1. Goals must be connected to one or more of Maslow’s Theory of Needs.

2. Goals should be defined as either specific or holistic

3. The purpose of a goal should always be challenged and extrapolated.

   1. All goals have a principle, some level above them, that is not driven by desire but by ‘rightness’ (i.e. eudaimonia, the ‘good life’, etc.)

4. Goals should be connected to habits that help you achieve them.

   1. Any goal that lacks this should be considered an aspiration. More on that later, I think.

5. The purpose of a goal should be categorized as proactive or reactive.

   1. Always reframe a reactive goal as a proactive goal. If you can’t, then this prompts some form of introspection (i.e. journal, therapy, etc.) to resolve that inner conflict.

6. Every goal should have a post-mortem.

   1. If a goal is proactive (see #5), then you should feel no pressure to achieve it if you feel no longer aligned with it. You should, however, dissect why you no longer feel the same way about it.

   2. Habits that are connected to an inactive goal should be shelved. If they feel good, as why and see if that sparks a new goal.

7. You should set a recurring schedule to revisit a goal and see if you are still aligned.

   1. Use a set of prompts that will dig into your current life events, and how they are influencing that specific goal.

   2. There should ideally be a metered approach here (i.e. sample of 3) so that you aren’t influenced by your mood at the time, etc.

“Trevor, I’m bored”

Who thinks a lot of the above is useless and overkill? That we should operate on first principles and not worry, to this extent, about goals / routines and how they relate to our lives?

I think, like with anything, there’s a level of ignorance that helps you make progress as an individual, and there’s a level of accepted simplicity that causes very serious, downstream problems when those architecting a solution fail to ask the right questions. This is especially true with areas like physical and mental health. While the examples are extreme, I can think of numerous scenarios where science the ruling narrative got it wrong, whether due to the lack of technology available at the time (i.e. assuming lobotomies were the best solution for serious mental illness) or whether due to flawed first principle thinking (i.e. preaching to homosexuals to ignore their impulses, creating a host of mental illness, being ostracized by society, etc.). I truly think that this space is an area that can have massive outcomes for individuals, or, could greatly hurt them.

If you’re bored and want the “So what?” of this, I would skip to Build. I’ll be the first to admit that I’m prone to overthinking and maybe the solution is to build something based on initial hunches and then iterate alone the way. But, as a growth marketer, I’ve learned that ‘iterating’ means nothing if you don’t know WHAT you are testing and HOW you’ll plan to iterate based on results. So, to some extent, the above is less “let’s get this perfect” and more “let’s challenge ourselves and think about this the right way”.

FWIW I also think there’s a reason why academia / think tanks exist — ”we have an idea, let’s flesh it out and research it” VS “we have an idea, let’s launch it tomorrow”. I think the ruling question should be “What is the propensity to harm if we launch this tomorrow”. An AI product that creates new blog posts for you? Not much. A building made out of new metal that is supposed to hold more weight? Maybe test it first. (can you tell I’m reading Atlas Shrugged?)

What’s in a Routine? (Think)

(This section was originally a sub-heading, but I realized that both 1) This post is getting unruly and 2) A lot of the above is inherently more ‘Think’ than ‘Research’ anyways. For a sneak preview of next week, ‘Research’ was supposed to be an in-depth look at habit tracking apps and solutions, but I felt that it was difficult to do that without first establishing the context of what goals, habits, etc. were. See a bit of this in Build)

One of the last bullets in ‘What’s in a Goal’ re: “how often are goals revisited” sparked the idea of goal integration — how do goals shape our lives, and more specifically, our routines?

Let’s take Majid for example. I defaulted to this because I’ve been exclusively using Anglo-Saxon names in my posts and it was the first that came to mind (although likely due to the artist)

He is single, in his early 30s, and works as a mechanic. Let’s try to sketch out his routine as it stands. For sake of argument, we’ll ignore any other goals he has, and just focus on his life. We’ll include (2) ‘random’ habits in purple.

Let’s assume that Majid has the goal of wanting to lose some weight. With the framework:

1. Maslow’s Needs — Physical Health, Self-Esteem

2. Type: Specific (”I want to lose 10lbs”)

3. Extrapolation

   1. Majid thinks that losing weight is part of looking better

   2. Majid wants to get a girlfriend (eventually wife)

   3. Majid wants kids & a family

   4. Majid believes that having a family feels ‘right’ to his life’s purpose (furthest extension)

4. Habits

   1. Start going to the gym

   2. Eat at a caloric deficit

   3. Drink more water

5. Purpose: Reactive (Reframe)

   1. Majid was unhappy that he’s getting older but doesn’t have a long-term partner. He thought that getting in shape would help to attract one.

   2. Upon reflection, Majid knows that he is a bit overweight and misses how he felt when he was younger and more athletic. He believes that he has neglected his health, and wants to lose weight to feel better about himself, in isolation.

   3. [Sidebar - I think a lot of the “lose weight” goals when reframed to proactive lose their weight (pun intended), and people realize that there are other goals - related to broader health - are more worthwhile pursuing. Losing weight is likely just a byproduct of that]

6. Post-Mortem: Not applicable (this is an active goal).

7. Reevaluation: Majid will check in on this goal in 3 days, 2 weeks, and 4 weeks.

   1. Prompts — How do I feel about my current weight, (1-7 scale) do I think think this goal is more, less, or equally tied to my principle (have a family) than before, do I have ideas of new goals that are better aligned, list any events or things that happened which impacted how you felt about this goal

Now, let’s look at Majid’s schedule and try to fit those habits in (red). I’ve skipped some steps here for sake of argument (to focus on the routine VS the habits or goals):

New tasks

• Gym after work, meaning he’ll be eating dinner later, losing an hour of sleep

• Meal prepping and calorie counting, means he’ll be losing another hour of sleep

• Water bottle prep, means he’ll lose another 30 mins of sleep

In the scenario above, with no changes to existing routine (and assuming Majid can’t wake up earlier + can’t be late for work), then he effectively has to eat dinner later and lose 2.5 hours of sleep. That’s a huge tradeoff, and it’s unlikely he’ll do it.

Therefore, we have to ask whether his two ‘random’ habits - crypto news and portfolio update - can be replaced by the new goals. In this very basic example, the principle that most people operate is that goals are zero sum; you will have to sacrifice one thing to gain something else. I’ll now reintroduce the “everything has a goal” idea, because:

• Going to work on time → Keeping a job → Having enough income to meet needs

• Sleeping 8 hours → Being alert at job → Having enough income to meet needs

• Read crypto news → Make $$ from crypto → Achieve financial freedom

This brings up another theory: routines are dictated by meeting our basic needs and achieving the goals that we value the most. I would curious to see how much of someone’s routine is driven by needs instead of goals, and how much time there is to actually craft new habits and achieve those goals. Note that in my research, not having enough time was a major blocker in being able to achieve a goal like starting a business.

This brings up several questions about routines, paralleling the discussion for goals, and how we come to them:

1. How do we create a routine?

   1. What do we see as part of our routine and ‘things we have to do’; which are not one-offs (see #4a) but inherited as part of the human condition (meeting our needs)

2. How much intentionality and decision-making goes into a routine?

   1. How much is expected with

      1. No autonomy (i.e. for a McDonald’s worker, what you do at work)

      2. Some autonomy (i.e. what time you wake up, constrained by working hours)

      3. A lot of autonomy (i.e. what you do after dinner / before sleeping, if no other commitments)

         1. (Note how this parallels proactive and reactive goals)

         2. How can you classify autonomy with routine? I.e. having a girlfriend (self-imposed) will put constraints on your time, but that is different than having a job (likely less self-imposed), and decisions that are potentially self-imposed but then indefinite (i.e. having a child).

         3. What role does willpower play into determining autonomy of a routine?

   2. How much of one’s routine is pre-planned? How often is this plan created?

3. How often do routines change?

   1. What drives this change?

      1. Are there parallels here to goals? I.e. your routines change when your goals change? (Outside of one-offs, see #4a)

   2. What constitutes big VS small routine change?

      1. How much of this is objective (i.e. waking up 3 hours earlier, working a night shift VS day shift) and how much is subjective (i.e. if eating dinner 1 hour later is harder than going to sleep 3 hours later)?

   3. How much does a routine need to be altered to be considered a change?

4. How much of our lives is routine?

   1. How many one-offs (doctor’s appointment, car trouble, family visiting, etc.) drives routine changes but in themselves aren’t considered ‘a new routine’?

[A Working] Theory on Routine Hierarchy (Sookraj, 2024)

So, my flight home has about 2.5 hours left on it (7 hours total) and if I subtract eating and watching The Last Voyage of The Demeter (good-ish), I’d estimate that I spent around 2 hours on this post. I think it’s fair that I spend at least another 30 mins, so I’ll take a stab at this and then move to Build, so I have enough time to sleep watch some Netflix re-runs. And since I acknowledge it’s a ‘stab’, I’ll call it a working theory 😎. I also won’t apply it, retroactively, to Majid’s routine, because I think we saw enough of that with the Goals example)

1. Routines are comprised of individual ‘practices’ that make up your day.

   1. These should be considered as anything that you do consistently. You can define consistently how you wish.

2. Practices should be labeled by frequency. (i.e. number of times per week)

3. Practices should be labeled by priority.

   1. Go through your routine and stack rank your practices from 1 (necessary to survive) to X (lowest relevance).

4. Practices should be split into Malleable and Non-Malleable.

   1. Anything that you have control over (sleep, eating, etc.) and is not a constraint from someone else is considered Malleable. More on this later.

5. Practices should connect to either a reduced version of basics needs, a principle (’rightness’), or a goal.

   1. Reduced version = what you need to survive and be safe; food, water, shelter, etc.

   2. (You can already see how there is threading here, between routines & goals)

6. Practices that are not connected to a basic need should be intentionally created.

   1. This means you shouldn’t automatically have any practices in your life that don’t relate to basic needs.

7. Practices should be labeled from 1-7 by ‘ability to change’, i.e. 1 = You can’t change it even if you tried, 7 = it’s very easy to change*.

   1. *This could also be done in the stack rank fashion, similar to #3, but this feels right for now

8. Practices should be given a percentage (out of 100) of willpower that you can allow, that day, to accomplish it.

   1. Your percentages must add up to 100.

9. Any changes to your routine should fit into the practice framework of #2-8.

10. Any practice that you remove from your routine should have a post-mortem.

    1. You should be able to explain why you are no longer doing this practice, i.e. if it’s connected to a broader goal, and what is replacing it.

    2. Any practice that falls below a certain priority level should be ‘on probation’ and subject to more stricter reviews.

11. You should revisit your routine on an agreed-upon cadence, to re-evaluate how you feel about it.

    1. Full reviews should be done very infrequently (i.e. twice a year), whereas check-ins via prompts should happen more frequently (i.e. every week)

    2. Weekly prompts may include what you wish was different about your routine, what you would change this week if you had the ability, what you plan to change this week, what has affected your ability to make changes, which practices you are most/least excited about, and if there are any events / people that have affected the autonomy of your routine

12. You should revisit your individual practices at an agreed-upon cadence.

    1. Routine re-evaluation should take precedence over this (see #11), and this is more to act on current scenario / feeling VS logic / planning.

    2. There should be two prompts: one that is “excitement about this practice 1-7” and the other is “do you want to skip this practice today/this week (TBD)”, with rationale if you decide to skip it

13. Non-Malleable practices should be challenged.

    1. A list of alternatives should be given and kept in accordance with that practice.

    2. Note any incomplete information you have on these practices, as they involve other people, and make an action item to get that information.

14. Routines must be implemented in a system that can be followed and easily changed.

    1. For simplicity, Google Calendar, for over-achievers, Potential

Rules for Debate (more on this later)

1. One person in your support system (family, friend, partner, etc.) should be given Power of Attorney in your routine changes.

   1. This means that any changes to a practice which falls under ‘basic need’ or ‘principle’ should be shared with them, and their input should be gathered.

   2. You make the final decision on any changes to your routine.

What can I do with any of this info?! (Build)

Hey builders! Thanks for coming back. You can ignore the ‘any of this info’ if you skipped most of the content above, and use the below to segue:

For example: I mentioned that I would do an in-depth habit tracker review later, but they usually hit one of the following:

1. Goals & Habits — Set out what you want to do and how you’ll do it.

   1. See Me+, Productive, Streaks, etc.

2. Routines — Create a system that you can follow on a set cadence.

   1. See Structured App.

If my two Theories are correct (on Goals and Routines), then you can’t achieve harmony between your goals and your routine without a lot of freakin willpower. This is why the ‘nerds’ (biohackers, life optimizers, etc.) are confined to a part of the internet where they create spreadsheets, use a smorgasbord of apps, and meticulously plan everything out.

If you have amazing willpower, this is easy. If you have poor willpower, you’ll have to work a lot at it. I’ve been working with my coach to over a year to get to a place where I have a decent system, and it still takes so much work to maintain. This is why habit trackers, as a product category, suck.

As I mentioned in my last post, I’ve been talking to Welf from Potential for a few weeks and we really hit it off, so I was exploring a way to work with him. Since I was already in Europe, I decided to extend my trip by a couple of days to visit him in his hometown of Altenkirchen, about 1.5 hours by train outside of Cologne (Germany), and jam in person. See below for Maps and a selfie :)

We came to a lot of conclusions on this space and how to approach a product here that looks at using both Large Language Models (LLMs, i.e. GPT) and iOS features (i.e. Shortcuts - which you may not have known exists / what it does). We’re currently exploring what a longer term working relationship might look like, who else would be involved, etc. More on that soon!

Separately, I wanted to include some core reflections as part of this trip and conversations with some close friends. This section will no doubt expand in the near future, as I prove/disprove some of the below, talk to more people, keep working in the space, etc:

1. I’m not convinced this is a product problem. I don’t think this is a case of “if I had a powerful enough app, I do all of the above”. When we look at users, we have to consider how they are segmented and how they fit into an Ideal Customer Profile (ICP) to target and service.

   1. There’s a common trope within startups that you can’t sell to everyone, and this space is no different. The initial product will necessitate a level of focus and testing to get to repeatability.

   2. As an example, Person A needs a reminder on their phone to do something. Person B will see the reminder and ignore it, but they’ll do it if their friend reminds them (social contract). Person C is avoidant and will only do something if it affects other people, not for their own gain. These people all have habit problems, and the specific scope of “create the best reminder experience” only scratches the surface (and doesn’t solve Person A, B, and C’s problems) of it.

   3. I’m also not convinced that the ICP is life optimizers and people who are very steeped in this already. I think that Total Addressable Market (TAM) on that group is too small, and it’s more compelling to focus on a specific use case with an audience that is acutely afflicted by this goal / routine problem (i.e. parents, people with ADHD, etc.).

2. I don’t think the goal is to create a phase shift. I’m skeptical that, given how most people operate, implementing the level of rigour I’m thinking of above across all areas of your life will be possible. I think this is also a core flaw in habit trackers - they try to do everything.

   1. In reality, I think it’ll be way easier to focus on an aspect of goal/routine change and focus on changing that for the better. I think there will be so many learnings from that, and the 10th iteration of that product will be a massive winner.

3. AI is creating a category here that wasn’t possible ~ 5 years ago. Every app is built on willpower and habits, especially trackers. I think AI is giving us a bridge where you don’t need the level of intentionality you did before to implement routine change and hit your goals.

   1. More on this later, as I zone into the specific categories, users, and problem sets that are most compelling.

4. There are implications to this that extend far beyond goals & routines. I think it’s easy, with a health app for example, to say that you changed someone’s behaviour and health outcome for the better (i.e. helping them eat healthier). I think it’s possible to convince yourself that that’s all you did, and you should keep going. I think that in certain categories, that is a very flawed way of thinking.

   1. Uber created a gig economy to reimagined how we viewed 1099 workers (contractors), working hours and malleability (i.e. driving someone home on your way from work for $$, VS picking up a shift at a diner), etc. There are multiple books (The Sharing Economy, Consuming Life) that I read in college that go deep into the implications of this. You can argue that Uber didn’t need to care about this when building the company, and in a lot of ways you’d be right, but if my goal is to enact positive change through a venture and it does a lot of harm, I wouldn’t feel good about that (no matter the results).

   2. For a more direct comparison, what we’re getting people to do in this category is to challenge their existing way of working and be intentional (self-authorship) with their goals & routines. I find parallels to what Kegan said here about how moving someone from Stage 3 to 4 who doesn’t want it, will cause a lot of problems. The reason I said “for debate” in the Theory of Routines is that anytime you involve other people in your decisions, there will be friction. I want to be conscious of what this might entail.

5. I think this is an app-enabled solution, not an app solution. This may be longer term thinking, but you’ll recall that my early ideations on wellbeing were around cohort-based courses and showing people ways to make diverse income streams.

   1. I think that given how complex this space is, it’s unlikely that an app will be the panacea, or possibly that it won’t be effective in isolation. As a fairly versatile founder, I’m open to the solutions (courses, marketplace, B2B vs B2C) that will need to be executed on together to really make a dent here.

That’s all for today folks - stay tuned for more next week re: habit tracker breakdown (with graphics) and how I’m continually to build in this space. And thank you again for your patience on this post … I hope the 4,737 words (and 180% more than last week) ‘makes up for it’ too 😉