Amateurish and ersatz "thoughtful thinking aloud" is just the latest reason I can't stand listening to radio, and now prefer podcasts.
Pause and ponder all you want, Abumrad, Krulwich, Koenig et. al. I have set my player (Podcast Addict, among others) to skip silence and play at 1.2-2.0x speed, so that gormless pauses and ponderous exposition are now scarcely noticeable.
In this similar vein, I had a religious experience when I realized YouTube had a 2x button. I'm now livid beyond belief that I can't do it on mobile.
Although I will rarely listen to more emotionally charged content (TAL, Radiolab, etc) on the multiplier, since I don't listen to those shows for their facts or to learn something.
The connection to HN, IMHO, is this: Louis CK is extraordinarily creative and committed to his art and craft, attributes demanded of entrepreneurs. He sometimes figuratively "hacks" viewer's brains with clever, surprising, insightful works, even when he gets parts wrong. It's the kind of accomplishment I think we can aspire to. We want our code, or our hardware, or our bare idea, to change minds, to inspire discussion, and even to disrupt lazy convention.
Oh, and the topic of this episode is not at all removed from women in tech, and how to "get it" and treat people well, regardless of age, size, shape, gender, religion, etc; these are perennial HN topics, if I'm not mistaken.
Three years ago I just went for Bose QC-15s (in-canal earbuds weren't an option for me, but might be for you, to change-up 'phones throughout the day. Most are isolating, some are noise-cancelling).
Aside from the noise-canceling, the QC-15 feature I like best after 3 years of semi-daily use is that the cable disconnects smoothly from the headset when stressed, like when you suddenly stand up while forgetting to take off the 'phones. I bought a spare cable, anticipating breakage, but I've never needed it.
These are personal, "pro-sumer" headphones, which are definitely not built to take years of daily recording studio rough-and-tumble step-on, sit-on, throw-around abuse. I've never sat on or stepped on my QC-15s, so I don't know how they'd be affected.
These headphones offer pretty good battery life (I get 40 hours, because I don't crank them loud) and soft circumaural earpads. But even with the light earpad pressure on my big head, I "run hot", so the heat and sweat build-up sometimes bothers me. This is true of all "sealing" headphones. I got some relief with my earpad covers made of stretchy t-shirt fabric. Eyeglass wearers will feel pressure on the frames; I don't know any way around it.
Sound quality is fine for me with good bass and clarity; the sound stage is so quiet it's initially a bit spooky. They're quiet enough and sensitive enough to reveal sonic source faults like my laptop's hisses and crosstalk. I don't know how durable they are against overload: I suspect fairly robust, because the speakers are driven by the 1.5V-powered internal amplifier, not the source (mixer, guitar amp, etc). But I also don't know how protected they are against input signal level over their maximum rated 9 Vrms (http://www.bose.no/NO/no/Images/owners-guide_QuietComfort_15...).
The noise canceling is excellent for my most frequent uses (office, home & planes), and very good for my second-most-frequent uses (public transit, walking). QC-15s do not block people whistling and tiny dogs yapping; I really wish Bose would allow selectable algorithms or firmware updating; I'd pay $50 for that feature.
The earpieces rotate to fold flatter in one's backpack, messenger bag or briefcase (I often roll up the cord and stow it in an earpiece compartment).
I've looked the competition to the QC-15s over the years, but I haven't been moved to switch because the features and performance keeps me satisfied. I might switch if mine broke or were stolen, and some other brand offered cable quick-disconnect and useful selectable algorithms.
The difference (with tax and/or shipping) between your target price point and $300 isn't huge.
Though it was posted 2 years and 3 months ago, and the article states that the bug was fixed, to me, the interesting parts were tracking down the versions of git that were affected, and demonstrating the need for more rigorous regression test cases in build --test.
IMHO you have a comfortable cushion, and some time to make careful, thoughtful decisions. Some professional financial planning could set you up to relieve yourself of some worries. Having done phase 1 (acquiring retirement money), you can take some time and assess what you love in life, or to explore what that means. Phase 2 might be family, or it might be personal growth, or it might be an adventure, or investing, or maybe as simple as a soul-searing eye-widening scary-ass meeting with either Paul Graham or Mark Cuban. Something to consider. Short term, though, the sincere, hopeful recommendations by others here that you look into discreet professional counseling to break your logjam and apparent depression, and to help you make your way from phase 1 to whatever your next phase is, are not wrong. You might need the therapy after meeting with Graham or Cuban. Best wishes for your breakthrough.