Unemployment: One Month Update

About a month ago (2021-01-15), I quit my job. My aim was to spend at least 6 months unemployed, using the time on myself. Now that I’m about one month in, it seems like a good time to do some reflection.


First, where I’m coming from. When I decided on this change, there were a few main driving factors on my mind:

Essentially, I wanted to take some time to focus on me. I wasn’t happy because (a) I felt I didn’t have enough control over my life and (b) I felt deficient in various ways.

To give some sense of the things on my mind: fitness, cooking, dating, starting a company, being more personable, random side hobbies/skills, etc.

While my hope is that this period would address these things, I didn’t set out an explicit goal or path on how to accomplish them. This was intentional—I didn’t want to preemptively pigeonhole myself into one path or another.

In other words, it’s very free form and open. While I have personal expectations for “progress,” the only structure is structure I end up defining for myself.

I suspect this isn’t for everyone. A reason I think (hope?) this is fine for me: in the past, when I’ve been frustrated enough by a problem, I can’t stop myself from doing something about it.

How I’m Thinking

Self-Improvement & Productivity

My hypothesis right now: if I keep doing productive things, I’ll be going somewhere. This line of thinking is definitely influenced by and oriented around forming habits. It’s also a little influenced by some of the philosophy I’ve been reading.

Specifically, I am not setting explicit long-term goals or targets. These have uses, but I think they’re not for me right now—they’re constraining and I don’t know what a good, actionable goal is. I do have vague directions that I’m working in, and that’s roughly the most orientation I have.

Instead, I just try to set up structures that make sure I’m making progress. In other words, the approach is:

  1. Do small, productive things.
  2. ???
  3. Profit!

There are a few things that I’ve found especially helpful.

Five Minute Journals

I’ve been doing a quick journal some days (I miss a lot of days). It looks like this:

2021-02-10 11:05 Five Minute Journal, Morning

I am grateful for:

  1. I’m grateful for trying out a new workout routine.
  2. I’m grateful that I’m getting over my fear of spending money in order to better myself.
  3. I’m grateful for starting to explore subjects that are unfamiliar to me.

Today would be great if:

  1. I place my Amazon grocery order.
  2. I start building any site.
  3. I do my daily reading.

Daily affirmations. I am:

  1. I’m working hard to improve myself.
  2. I enjoy pushing and challenging myself.
  3. I’m in control of my beliefs and destiny.

While I believe the gratefulness and affirmation stuff might help, I haven’t felt it yet. It still feels a little bogus, but the cost is pretty low and everything I hear about it says it will pay off.

The thing I have noticed as useful: the list of things I want to accomplish each day. A key for me has been to make these really simple. Pretty much anything that requires mental effort makes the cut (as you can see).

I fail to accomplish all three items pretty much every day. (I tend to write them down then…do anything else.) Still, there are days when I’ll feel guilty and attempt one more item. I normally end up completing it, and relieves a fair bit of anxiety.

Habit Tracker

I found a simple habit tracking app. It literally just has an item name and an ability for me to check off each day that I do it.

This has been super helpful: I have a list of all the things I’m actively working towards. While it’s a small feeling, the satisfaction from checking something off is nice.

I also use it for stuff that isn’t exactly a habit. I read multiple books at once, so I just include each title in the tracker. This helps me focus on the “more important” ones and makes me feel guilty if I’ve been neglecting something.

As a side thought, this is probably more of what JIRA backlogs should be like.

Not Beating Myself Up

My ideal version of me is way, way, way better than who I currently am. I’m especially lazy and prone to doing non-productive things (e.g. video games).

I try to remind myself to not beat myself up over this. It’s really easy for me to feel guilty and fall into self-pity.

Of course, dwelling on the past or what could have been doesn’t change anything. I try to ensure my guilt only comes up when I’m making decisions and actions—I want to make myself to make good choices in the moment, but not to dwell on past choices.

Topics and Themes

The main things that I think about.


This one is interesting, because I half enjoy it and half hate it.

In a colloquial sense (not the discipline sense), I think philosophy is really important.

I find it very frustrating when people can’t articulate, to at least some degree, what they believe, what they’re trying to do, and why they’re trying to do it. This is so frustrating to me that it probably accounted for a good chunk of my frustrations at work.

The discipline of philosophy applies this thinking towards life. It makes sense that this is important (what are you doing with your life?), but I’m mixed on the actual philosophy works.

So far, I’ve read Plato (The Last Days of Socrates), Aristotle (Nicomachean Ethics), and am currently reading Epictetus (Discourses, Fragments, Handbook).

Reading these works is frustrating, typically because (1) I don’t have enough of an awareness of their default beliefs, (2) how some of these authors write, (3) some of the works are really long and I lose focus, and (4) the logic and arguments sometimes seem confusing or convoluted.

With that said, it’s been interesting when I am able to extract some of their main beliefs that seem relevant to me. It’s also interesting when I realize some of these beliefs are commonly echoed today—was this an influence of the philosopher that’s survived for centuries, or is a “natural” result of people coming to cope with the world?

There are two main ideas in particular that have stuck with me.

One, you should live life by intentionally making good choices in your actions. The Greeks are particularly focused on making “virtuous” choices, but I’ve found this to be constantly relevant for me.

A more modern, pleb framing would be: do what should benefit the future you. Also, if you don’t choose that option, you’re going to be a terrible person. Put that way, it’s way easier to make the long-term positive choice.

Two, you’re in control of you—how you act, respond, and feel about things. This is a big theme in Stoicism.

Essentially, no one can take away your thought and feelings unless you let them (by valuing things things other than how you think). Epictetus often contrasts this with death or imprisonment—someone else might decide that you’re to be executed, but you decide if this is going to make you miserable.


This boils down to doing helpful things for me, as an individual. Cooking, exercising, skincare, that kind of thing.

I admittedly am not putting a large amount of focus on this—just enough to periodically make things better. This is as small as ensuring that I regularly cook, and that I try a new recipe once in a while.

The bar is low, but I think I’m fine with that. I’m definitely improving—I’ve been working out 6 times a week for over a month, even it’s a small and easy 5 minute workout. I just try to make sure things don’t constantly feel too easy.

Reading & Learning

I’ve been doing a lot of reading, though I’m not sure I’ve been doing a lot of learning. I mostly read things that are interesting to me, while aiming to also venture out a bit into areas that I might not normally read. I haven’t been too focused on a particular topic, other than topics I’m writing about here.

I often find myself reading multiple books simultaneously. There’s two main reasons for this: to scratch multiple itches, and because some books are so long it would be really dull for me to go one at a time.

As a snapshot, here are the books I’m actively working on:

Structuring Knowledge

This idea is especially interesting to me. We all encounter tons of information over the years—how do we ensure that we can find and/or remember relevant information when it’s needed?

Some things we just remember. Often, these are things that stuck out to us or that we use regularly.

But there’s also stuff that isn’t worth trying to remember every day—yet might be useful down the line. If knowledge could be structured as a web, there might be several nodes that you’ll draw a connection to in the future…but those nodes are not useful today.

I’ve sort of tried to do this in the past. I added notes when I wasn’t lazy. Over time, the books section has been the most useful because it’s just notes.

Everything else is just a mish-mash. That’s because the ideas are loosely connected (by topic), but I have to form a more explicit relationship to actual store the information. In other words, knowledge isn’t stored hierarchically.

A while back (2 years ago?) I heard about Zettelkasten, which I think is an interesting methodology. It sounds powerful, though in practice a large limitation I’ve had was with using software that made it ergonomic to use. (Zettlr was the best I found.) Because of that, I only made a half-hearted attempt to use it.

Recently, I decided to try out Roam. It has the ability to do Zettelkasten-type note taking, isn’t structured hierarchically, and has a much more granular unit of knowledge. It’s been interesting, though still too early for me to tell if it’s been useful.


Admittedly, not much going on here. I occasionally try to improve my profiles.


Wasn’t exactly sure what to call this section. I’m interested in starting a company, but I currently have no idea what such a company might do.

I’ve done very little towards this. Most of what I’ve done is some learning to help me understand what to focus on. Most of this comes from YC’s startup school—especially around how to evaluate ideas.

A challenge I’m currently facing: what do I want here? Do I want to just build something and aim for it to bring in a relatively small amount of money? Or is it a hypergrowth startup that I want?

I’m hoping to pick a direction; I’m waffling on this decision point and it feels like I’m wasting time.

Another big obstacle here is that I haven’t felt excited about doing this. Which is odd, because it’s probably the thing I am most curious about trying to do. I’m not sure if this should be chalked up to (not recovering from) burnout, or that any work I need to put in currently still feels more like a chore.

What I’m Doing

Morning Routines

At this point, I have a fairly stable morning routine going on. I’m pretty happy with what I’ve gotten out of it because (1) it gets me doing good things and (2) I have never looked back and felt bad about following this routine.

The main pieces are:

It sounds dumb and simple (it kind of is), but in particular there were things I was not doing before: skincare, meditation, and exercise.

Knowledge Ingestion

It’s harder to explore if you don’t get exposed to ideas. One thing I want to improve on is knowledge ingestion—making sure I get high quality information.

The main thing I’m doing towards this so far is using Feedly Pro. They tout an AI assistant, but either I’m using it wrong or it’s complete garbage so far. Every day I skim through ~200 headlines and it doesn’t really help me to find articles of interest to me.

I probably wouldn’t recommend the assistant today, but Feedly in general is nice. The hard part is if you start adding a lot of sources, particularly sources that (for you) are very noisy.


Every few days I try to write something (as you can see). I don’t publish everything, and I haven’t really been focused on quality. This has led to some posts that are not great for reading, but I’m not too worried about that right now.

It might be interesting to try to grow an online writing presence, but I struggle when I try to figure out what that would be centered around.

Progress Check

Now, the main reason I wrote this post—how am I doing? A downside (kind of) to my current approach is that lack of clear goals makes it hard to evaluate how I’m doing. Many days feel the same, and I don’t know if doing stuff is turning into progress.

I think it’s safe to say that I’ve had some wins. I’m spending time on and improving in various areas. I’m implementing new behavior changes that have been helpful. All of this may not be happening instantaneously, but there’s definitely movement.

Another significant thing is that my mental clutter feels like it’s decreasing. Aside from having more defined ways to approach thinngs, I’m also getting better at doing routine tasks that I normally would have put off.

There are some days where I feel like I have nothing to show or that I need to force myself to accomplish something big. When this happens I’ve been trying to get myself to not worry about this line of thought. The fear is if this line of thought is wrong—maybe I am doing what I should be doing, and it’s just paranoia or fear that’s trying to mislead me.

Anyways, that’s the update. Things are happening, but I still have no idea where those things are going to take me. Feel free to reach out if you want to hear about something in more depth!