Thinking out loud

Things I've been thinking about: Ideas, decisions, things I found intriguing, open questions, whatever. I normally keep these in my notes app (Bear notes), but I was inspired by Nadia's notes and decided to share them publicly in case anyone finds them helpful or interesting.

Feb 25, 2021

Building software products is still so damn hard.

The very first version of anything you build is so painfully embarrassing. It often feels like that first version is less about solving the actual problem and more about giving yourself, and your users, hope. About exploring the problem space. About starting the engine that will ship the ongoing updates that will finally solve the problem.

Jan 25, 2021

Journaling through anxiety and uncertainty.

While I’ve been journaling for a long time, a new activity I recently started is to sit down for long sessions of journaling when I’m feeling anxious or uncertain about things. I do this freeform, without any specific prompts. And the sessions range anywhere from an hour to an afternoon. I find it’s a great to force yourself to think deeply about the problem in an “out loud” manner, while still keeping your thoughts private such that you can be as raw and honest as possible. A quick 10-20 minute journal doesn’t let you get deep into the weeds of the problem, but an hour or more really does. I often tend to make diagrams of some kind, where I’ll think through the problem in a non-linear way. I find seeing a fill “schematic” of my thinking, and editing it in real-time, really helps demonstrate where my logic is flawed, or where I’m letting anxiety or fear cause me overthink something.

If you’re feeling anxious or unclear about something important, try journaling for solid hour or more. You might surprised what comes out of it.

Note: I use the DayOne app. When you're journaling for long periods, hand writing your thoughts can limit your ability to just stream consciousness onto the page. Digital works best for this. I also suggest not doing much, if any, editing. Just let it all flow out.

Jan 21, 2021

Recently I’ve been exercising with only a yoga mat and TRX straps. I generally much prefer using actual weight: dumbbells, barbells, kettlebells, cable machines, etc. When I don’t have those and have to use my TRX, I tend to complain a lot about it. But recently something changed, and I now love working out with TRX. I think as a result of wanting to get a great workout, I simply stopped complaining and started thinking about how I could best make use of the tools I have. And if you give TRX a chance, and pay close attention to your form and movement speed, you can get a hell of a workout. I feel like many things in life follow this pattern. There’s always an option to complain, to say “I just wish I had the better version of this thing.”, but it’s often much better to say “Well this is what I have right now, and there are ways I can make the absolute best of it”. What’s interesting is sometimes you find out that by putting extra attention and focus on making the best of what you have, you’re not even just “making due”, and instead, you actually get the entirety of what you want, or more.

Dec 14, 2020

Thinking about how companies manage knowledge. It feels like what we'd want is atomic content in a graph style structure, like Roam, but with a Notion style hierarchical layer above. Something like this:


Dec 7, 2020

Morning routines. It feels hard to understate how important morning routines are for my daily happiness and calm levels. I try to do some form of morning routine every day, and a few times a week I'm able to complete my "full morning routine". My current version of that routine consists of a 10 min mediation, ~10 mins of journaling (a 10 point gratitude journal + some freeform journaling), making and drinking coffee, a short walk, and sometimes reading 1 interesting long-form thing (article, a bit of a book, whatever). The whole thing takes 30-60 mins total depending on how fast I'm moving that day and feels like one of the best time investments I make.

Dec 5, 2020

Stories with skill mastery. I’m realizing my favorite types of stories are ones where the protagonist is developing a skill, going from initial introduction to the skill to mastering it. Along the way, they overcome greater and greater challenges. I recently started watching The Queen’s Gambit and have been really enjoying it, I think because it has this type of narrative. There’s something exciting and captivating about watching a person grow and master a skill (including in real life), maybe because I value learning and growth so much myself. What types of narratives do you most enjoy? Why do you think that is?

Dec 4, 2020

Behavioral change. When I want to change my behavior in some way, I often try to frame the things I want to do (or to avoid) in an obvious way to make it easier for me. I recently decided to stop eating added sugar. Sugar of course is in nearly everything, so it's tough. Do I avoid all bread of any kind? Any take out food that maybe has sugar added in a sauce? The way I frame it to help me make the decision is to ask "what obviously has a bunch of added sugar?" and then just don't eat that. For me, that's things like chocolate croissants, muffins, almond milk cappuccinos, or ice cream. This prevents me from thinking too hard about what is ok to eat and what isn't. What sort of "simple" framings can you use to help change your behavior?

May 2, 2020

Learning Communities. Why aren't there more communities specifically focused on structured learning of specific ideas, strategies, and tactics that help you improve at your work?

When I say "learning communities", I don't mean schools. I mean specifically communities that many adults with existing full-time jobs participate in to improve at their work.

In tech, the obvious answer seems to be that these communities already exist on:

The other type I hear a lot about is private chat groups on Whatsapp, Telegram or other similar services.

But there's a a few things I feel are missing:

  1. Depth of engagement with the ideas and their real world application.
  2. Collaborative problem solving.

On Twitter, likely the biggest community that has some focus on learning, you might discuss the core concepts in a popular article with a bunch of smart people, but you're limited to what 280 characters can provide - which isn't much. It feels like the conversation never gets a chance to really get into the nuance. There's also no private group capabilities to support more safe, comfortable, intimate groups that can challenge each other and support each other in more specific ways that might feel inappropriate on public twitter.

In private communities on Slack or other forum type systems, the discussion can be a little better. And sometimes these communities might offer AMAs over Zoom, which get you a little closer to the concepts and the challenges you might face in real world application. But it still feels like the conversation isn't as deep as it needs to be to truly help people understand concepts, how to apply them across different contexts, and work through challenges as they do.

How can we build communities that help get us closer to the things that are missing? What might one of those communities need to include?

Some ideas:

  • Collaborative problem solving of scenarios that closely mimic various real world situations.
  • Easy group formation around specific learning scopes to create safer, higher quality groups for learning.
  • Significant guidance by people or software that ensures conversation and debate, problem solving, and support are focused around specific concepts useful to specific people in the community.

Some of the ideas around open-ended problem solving like Andy Matuschak outlines in his article, Building complex reasoning skills online through open-ended activities, could potentially be used here.

More thinking on this in a bit.