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life / learning

Getting in the Generalist Zone

. 10 min read .

I get a lot of funny looks from people when I talk about how I organize my life.

During any given week, outside work, I might be wakeboarding, baking brownies, taking coding courses, working on blogs, trying out muay thai, working on software project ideas, taking online philosophy classes, bouldering and so on.

To the outsider, this might seem like an absolute chaos of a life. Some people have even advised me to stop most things I do and instead focus on a few, and do them really well. Some went as far as saying that I am never going to get anywhere in life with this attitude of playful wandering.

I don’t blame them.

For a while, I really struggled with this. There was proof all around me that the people that seem to ‘make it’ are people that do very few things and they do them really damn well. And so I used to see this tendency to be a generalist as a bug, not a feature.

Gradually though, I slowly came to embrace my curiosity. Instead of shutting it up, I learned to listen and tame it. Eventually, I came to be the biggest fan of my inner generalist.

True Generalists are Consciously Unspecialized, Not Unfocused

From the outside, generalists appear rather unfocused. Our efforts seem to be scattered in a million directions with no apparent purpose. This is a fair observation. But there is a nuance not many people see: doing a lot of things doesn’t imply indecisiveness or lack of direction.

True generalists aren't people who aimlessly wonder around. True generalists, per my definition, are those who consciously decide to build their life around a specific set of activities. In that sense, true generalists  aren’t too different from specialists.  They’re still disciplined in controlling their attention, still decisive in the things they are splitting their time for and still driven; it just happens to be 10 different things, not 1. A true generalist, is a curious person that knows that they need variety of experience and refuses to bend to the will of a specialist world.

Being an effective generalist is like being a military general managing their troops for a full on warfare going, with 10 battle-zones open. Much more complex than having  a single battlefield.

Being able to execute as a generalist though requires elaborate planning.

There is a method behind the madness.
I will attempt to show you mine.

The generalist's bulls-eye

The art of being a generalist is being able to find the right balance of two dimensions:  flexibility of schedule and number of activities.

Finding balance in each of these two dimensions brings you to the center, the generalist's bulls-eye.

This bulls-eye is my operational sweet-spot. Think of this as ‘being in the zone’. It is a mode in which I feel great fulfillment because I am adding enough fuel to each of my identities: the athlete, the  writer, the friend, the product manager, the curious learner without feeling like I am sacrificing much of my freedom.

Consistently hitting that bullseye, feels like I am moving at incredible velocity while being in a constant state of bliss. It is a great feeling.

The heart of this framework

Soren Kierkegaard called anxiety the dizziness of freedom. My interpretation: freedom is a double edged sword. Freedom enables us to have boundless options which is incredibly empowering but too many options and we end up with choice paralysis and with that we become anxious, which is incredibly disempowering.

So how one needs to handle freedom is by setting their OWN boundaries. This 'freedom management' is  at the core of this framework. If we do not consciously manage freedom ourselves, somebody else is going to do it for us indirectly. Remember this as we go along. I am setting boundaries to set myself free.

Dimension #1: Limited Variety

The first axis we will look at is the number of activities.

Too few activities and I feel disengaged, bored. Too many activities though, and my attention is spread so thin that everything is done at a low standard and I feel underwater.

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The objective is setting enough boundaries so that the choice of activities is not overwhelming while it does not feel overly restrictive. Is it improving at piano? Learning how  to speak Korean? Learning how to freedive? Weightlift?

That right balance is limited variety.

Dimension #2: Rigid Flexibility

Rigid Flexibility takes the prioritised list that resulted from limited variety and allocates it. It takes the 'what' and defines the 'when' for each.

Too rigid of a schedule and I feel like I am suffocating because there is no space for spontaneity. There is no space to do the things that would bring me joy on the spot.  Too flexible of a schedule though, and I get nothing done. My attention gets scattered in 100 different directions like a kid in a candy store and my discipline goes out the window.

The objective here is planning enough to enable me to focus and get shit done while not feeling like my days feel like days in the military.

The right balance is bounded flexibility.

Ok, now let's get tactical. Let me show you the actual framework I use day-to-day to enable me to consistently hit that bulls-eye...

Setting up the boundaries

Step 1: Limited Variety

I separate activities in these themes:
Sports  || Learning || Creativity Habits || Reading || Software Side-Projects  || Admin

I use Notion to organize each. Here are some examples:

Learning Projects
Side Projects
Side Projects p2
Admin + Reading List
Sports

These canvases are filled with all the exciting things I want to do someday. A generalist should be able to fill those boards to the brim! We are at the very end of the variety spectrum though. This are way too many activities. I simply cannot handle 21 learning projects, 76 product ideas, 8 sports, 23 to-do's and a job at the same time can I? So the next step is prioritization. It is to ruthlessly cut off the activities that are lower in priority in order to reach limited variety.

For each of the themes(sports, learning, creativity etc.) I pick a handful of projects to focus on. These might be any size project ranging from 1 week pursuits like: learning how to make ramen to 6 month projects, like: learning full-stack web development. It doesn’t matter. The important thing is to only have a handful in your plate at any given point.

There is no science behind how many projects from each field I aim to work on but I would say that anything above 2 in each category is risky. This means that I only allow myself to focus on 2 sports, 2 learning projects, 2 side-projects and 2 creative habits at any given point in time.

While I did have times where I was working on 4 learning projects while abandoning everything else followed by a period where I would only do sports and writing, this 'monomaniac'  approach does not work as well for me. Playing with a variety of activities on a weekly basis is my style of doing life .

So after I go through each theme's table and prioritize, we get a more filtered view:

Limited variety achieved.
We have a list of ~8 activities that we are commiting to execute on a weekly basis.

I am not allowed to touch any other projects before I finish the ones I have marked as priority unless something drastic happened and priority has to change. Priorities should not change often after you have started the project. You can shuffle the NEXT projects as much as I want but to stop a project is a big deal. If one is completed, I choose if I should replace it with a new project or if I should instead focus on the rest and add something later.

Step 2: Rigid Flexibility

Now that we have the what, let's move on the when. Let's slot them in a weekly schedule.

Too much flexibility and it is hard to find the discipline to do everything that needs to be done. Maybe it is just me but I am super unreliable and untrustworthy. If I leave some activities to doing them 'whenever I feel like', they will never ever happen. Humans are built to avoid pain. That is why I definitely need some rigidity. But not too much.

Without some rigidity (aka schedule/routine) am unable to build rhythm to my life and have peaceful execution because I spend too much energy balancing alternatives and making decisions as to what is best do at any given point int time. This causes decision fatigue which then inhibits my ability to instead use my limited energy on execution.

Rigidity is also required to form routines and rituals. Routines and rituals are needed to add a cadence to each activity. They make them repeatable and with that, sticky. Habits start forming. A habit turns an activity to a non-negotiable action. That means 0 energy is spent deciding or fighting it, you just execute. These habits compound over time and create a snowball effect, hence why rigidity is paramount.

Too much rigidity though, and there is no time for spontaneity. There is no space to go for wakeboarding instead of climbing, no space to skip writing and go for a walk in the park instead, no space to spend the evening baking with friends instead of working on the UI designs of the side-project. Everything feels forced.

Fulfillment lives between intention and spontaneity.

The ultimate state is a state of peaceful execution yet maximum engagement. Peaceful execution requires a pre-commitment; rigidity. Engagement tho appreciates that we are fluid day to day in what would satisfy our needs an bring us joy. The perfect balance is the point at which we have enough of both.

So the question becomes; what should I schedule, when? This is a hard answer to formulate but I will do my best to describe my thinking.

The weekly schedule

During this 2nd step of rigid flexibility, I would start by assigning a day/time to the general activity theme: sports and an optional description of which of my prioritised sports I will do during that block: for example: wakeboarding every Saturday 10am

As a general principle, the non-creative activities (sport, learning & experiences, reading) are predefined in terms of the when and the what while the creative activities have a looser when and no what. So each theme has a varying degree of rigidity.

Below is my weekly schedule.

Each theme has a slot and some of the slots have a description of what it is I should be doing. Below is the current tactic for each theme. These are fluid. Not on a weekly basis but quarterly. For example, the learning section is super rigid and limited because of the 12h a week live coding bootcamp. After that course ends though, I might decide I want to learn calligraphy and video editing twice a week, it then becomes less rigid and with more variety.

Sports

# of Activities | Limited  ▢▢▢▩▢ Various
Bodybuilding | Wakeboarding | Bouldering | Snowboarding

Day & Time | Rigid ▢▢▩▢▢ Flexible
Weekdays is after work. Weekends, flexible time.

Session Plan | Rigid ▩▢▢▢▢ Flexible
The limitation with physical activity is soreness. There is not space for being spontaneous because there is an optimal way to line up those sports to ensure there is enough time for recovery. So these are slotted as such:

Learning

# of Activities | Limited  ▩▢▢▢▢ Various
Coding

Day & Time | Rigid ▩▢▢▢▢ Flexible
Coding is a course that is pinned Tuesdays & Thursdays 7-10pm and Saturdays 10-5pm

Session Plan | Rigid ▩▢▢▢▢ Flexible
Tuesdays, Thursdays and Saturdays, coding. I try to follow it religiously but some days I let myself swap. The other two, once a week.

Reading

# of Activities | Limited  ▢▢▩▢▢ Various
Book: An Emotional Education TSoL | Badass | Online Blogs

Day & Time | Rigid ▢▢▢▩▢ Flexible
Late at night and maybe in the afternoon.

Session Plan | Rigid ▢▢▢▢▩ Flexible
Full flexibility.

Software Side Projects.

# of Activities | Limited ▢▢▢▩▢ Various
Goji | Foodtrucker

Day & Time | Rigid ▢▢▩▢▢ Flexible
Whenever in the day.

Session Plan | Rigid ▢▢▩▢▢ Flexible
It depends on which one requires my attention in order to proceed. Each one of these have their own prioritized list of tasks so I pick from there and plan according to relative priority. Some of these have monthly/weekly standups as well.

Creative Habits.

# of Activities | Limited  ▢▩▢▢▢ Various
Writing
Day & Time | Rigid ▢▢▩▢▢ Flexible
Weekdays before work as soon as I wake up (whenever that is. no alarm). Weekend, flexible.

What activity | Rigid ▢▢▢▩▢ Flexible
I have an separate process for prioritising blogs. I try to have a goal of the blog I want to work on. But it is rather loose. I might not feel like writing about something and instead pick another subject.


So with that, we have a weekly schedule:

Weekly schedule. View my entire Notion HOME screen here

This is not a complete framework. Simply the task of prioritizing the top activities we want to work on is an art of its own, deprioritizing and abandoning projects is can be a 3h conversation and the act of prioritizing subtasks and material of each individual project like 'learning gardening' or 'study advanced algebra' is enough for a book. There's more! Spacing sports to optimize for recovery, scheduling reflection sessions, habit formation, methods for staying consistent, scheduling activities depending on the time of day (willpower and brainpower management), optimizing learning for max retention and balancing all these with a thing called a 'job'.  As you dive deeper, there are layers and layers of complexity you will have to tackle; but let's leave those for another day.

If you would like further inspiration, you can take a look at Tim Ferris system in this video . You should be able to spot the same principles of limited variety and rigid flexibility. Keep those two as your compass. Limited variety so that you don't spread yourself too thin and rigid flexibility so that you build momentum while allowing space for play.

Not all who wonder are lost.

Generalists have a bad rep.

No, we are not unfocused, undisciplined or unambitious. A true generalist, I would argue, needs to be way more disciplined, ambitious and organized than the average specialist.

Being a specialist is hard because specialists have to say no to a lot of interesting activities. Being a generalist though is another level of hard because generalists have to context switch and plan for all the things they are committing to. All that, while feeling that they are falling behind.

If you are a generalist; ignore the critics.

I hope you have find the bulls-eye and show them how a full life is to be lived.