iPad as Desktop: Emacs

Lately I’ve been working on a setup such that I can use my iPad as my primary desktop, at least for personal tasks. In this, the first of what I plan as a series of posts about my journey, I’ll outline what I’m currently using to be able to use emacs from my iPad.


For the impatient, and also to serve as an outline for the post, I’ll just list out the tools I’m using to make this happen.

  • Blinkshell
  • Tailscale
  • Mosh
  • An M1 Mac Mini
  • A hardware keyboard

The combination of the above gives me a nearly desktop-native experience running emacs and other terminal applications on my iPad. Note that this setup of course requires network connectivity between the iPad and the Mac Mini, and there are some complications with that, but I’ll try to cover those later in the post.

The finished product: emacs running on a Mac Mini that I’m using Blinkshell to connect to with mosh over a Tailscale VPN connection


I run emacs as my primary editor/IDE/operating system. I’m not one of those old school emacs users, I’m one of the new young punks using someone else’s emacs. In my case, I’m using the doom-emacs package, which provides me with a very comfortable user experience pretty much out of the gate, and since I’ve been a vim user for so long, the adjustment wasn’t that significant.

Emacs is a gui application framework wearing the skin of a text editor. It has support for both terminal ui (tui) or actual native gui (gui) interfaces, and can do so much more than editing text. I primarily use emacs as an editor, however, and I primarily use emacs over other editors because of org-mode and org-roam. I’ll talk about org-roam in another post.

Emacs doesn’t have a native iOS port and it is highly unlikely that it ever will. Largely in part due to application restrictions on iOS making code interpretation not a supported thing, which is fundamental not only to the emacs experience, but fundamental to emacs operation as a whole. I mentioned that emacs is a gui application framework, and it is, but as part of that framework it has its own programming language, emacs lisp, which powers not only custom things, but a lot of emacs’ own built in functionality.

So, as a result, I need a machine somewhere I can run emacs on and have it display on my iPad. And the best experience for that is, in my opinion, a terminal.


Blinkshell is a terminal emulator, ssh, and mosh client for iOS. There’s so much more to it than that, but it has the basic functionality I need: terminal emulation, ability to configure ssh key authentication, ability to do ssh agent forwarding (I won’t be covering this here, as I’m on the lookout for alternatives and it’s been covered elsewhere). It also provides an extremely basic text interface for commands, which is nice, I primarily live in the command line and on my keyboard, not having to tap my way through menus and such to do things is a huge plus.

It’s not a free app, but I’m totally fine with paying for good software. It *is* open source, which is nice, as that allows for auditability and also allows me to try to fix bugs or implement features if I feel up to the challenge.

One thing I discovered recently that it had was support for OSC52 terminal sequences. This is something I only recently discovered, but the general gist of it is that it allows terminal applications to manipulate the clipboard on the client system. If you’ve ever highlighted text on iOS you understand just how hard it can be. Now take things like terminal gui elements into consideration, and it’s basically impossible to copy/paste from the terminal by hand. However, OSC52 allows your terminal application (such as emacs, vim, tmux, etc) to send its own clipboard contents down, so you can use those applications’ native copy/paste functionality to manipulate the clipboard on iOS, making it easy to, say, copy some code from a file and paste it into a discord conversation, or a gist. This is huge, and one of the things that when I first needed to copy something from blink was nearly a deal breaker for me, as I copy things out of my editor all the time, so having that be a bad experience was probably going to prevent me from being able to do this. Fortunately, the problem is mostly solved at this point. There are still some limitations, for instance it doesn’t seem to work with mosh, but there’s a PR waiting to be merged into upstream mosh which hopefully will make its way into blink soon after.


Traditionally, when I’ve wanted to grant access to a machine running on my home network, I have fired up my router configuration web interface, set a static IP for the machine, forwarded a port, etc. This works fine, but has some serious drawbacks. The most important one is that now this port is exposed publicly on the internet. That’s probably not toooooooo bad, especially if I run the service on an alternate port, but it’s still a vulnerability. It’s also a huge pain for the friend who’s hosting the machine for me, as they have to maintain this. And the only way they know if it’s broken is if I call them. Furthermore, it assumes a moderately static IP for the internet connection. When I had my cable connection, this was pretty reasonable to assume, my IP rarely changed. But with my new fiber connection, it seems to change fairly frequently. To solve that I have DNS somewhere and a script to update the dns record on a schedule, but if that breaks then I’m back to calling my friend. It’s all very fragile and troublesome to fix.

So I went on the search for vpn solutions. I thought of having a VM instance somewhere that both my remote shell machine and my iPad could connect to and that would allow me to connect between them. This is fine, and something I almost went with. I would have likely used OpenVPN for this as I’ve done a lot of stuff with OpenVPN in the past, I’m familiar with it, and confident that I could make it do what I wanted. One problem with this, though, is that third party machine. Even the cheapest machine is going to cost me a few bucks a month, and now it’s something I have to maintain. There are third party VPN providers, but I’m not sure how many of them would allow my clients to connect to each other through the VPN, and I’d really rather not use one of those providers anyways, for trust reasons, but also because I really don’t like their ad copy. But that’s another post.

But! I remembered. There’s some new vpn thing built into the linux kernel now, isn’t there? What was that called? Well, it was called Wireguard. I also won’t cover this here because it’s been covered in great detail elsewhere.

Wireguard’s model is point to point VPN. Meaning clients create tunnels directly to each other. Once the connection is established, you can do routing and all sorts of stuff, so I could do the central model with a VM somewhere with wireguard, but it’s still not ideal.

So I went looking for ways to make it so wireguard endpoints could “discover” each other. So I could have my shell machine on a private network with no ports opened, no assumption of a dynamic IP address, etc, and have it just work. I found this article that talks about various scripts and a third machine that updates dns entries and does some cool stuff. Exactly the sort of thing I was looking for. But again, the third box. I thought more about it and thought that would actually make for an interesting service to offer to the world, and thought about how I might implement that.

It seems I’m not the only one who had this idea. Tailscale is *exactly* this. And actually, it’s significantly more. Most importantly for my consideration is that it takes NAT traversal a step further. They will transparently (and securely) proxy your data between your nodes if the NAT needing to be traversed is particularly problematic. On either end. This means that, in theory, no matter where I am, or where my shell box is hosted, I can establish a wireguard tunnel to it.

And the best part: it’s free. At least for single user purposes like mine. They can do this because their service is just providing the discovery for the endpoints, they aren’t actually proxying your data (unless you have the aforementioned troublesome NAT), so their bandwidth needs are relatively low. You install the agent on your machine (they have iOS, Linux, and Mac support at the very least), log in, and your machine is now able to be connected to from the other peers you have set up, as if it’s all local. No ports to open, no dns to configure, no worries about static or dynamic IPs. It all just handles everything smoothly. Wireguard handles when one end or the other changes IP addresses, and tailscale steps in if both sides have changed, or when a new peer comes online and doesn’t know any of its peers. It also handles public key distribution to the peer nodes, and rotation of keys, and and and and and. Seriously well thought out software and service.


Blinkshell support ssh directly, but something else it supports is Mosh, the Mobile Oriented SHell. Mosh has some significant advantages over standard ssh that make it ideal for a client with transient internet connectivity such as a traveling iPad.

Mosh uses SSH for the initial authentication and session establishment, then switches to running on its own port using UDP. The fact that it uses UDP for this is huge, because it allows the client to go offline without having to worry about a TCP session dropping. This means mosh clients can go offline for a practically infinite amount of time without “losing the connection”. In practice what this means is I can pack up my iPad and head out on a trail for a few days without internet access, fire things up when I get back and my connection hasn’t dropped. This may not sound like a big deal, especially when things like tmux exist to allow you to background a terminal session on the remote machine, but it’s pretty big. For the iPad specifically one of the great things about this is that iPadOS times out tcp connections on background processes pretty aggressively to save battery life. So if I switch from my shell to watch a youtube video, say, or read an article, I may come back to my terminal and the connection has dropped, meaning I need to re-establish. This gets really old really quickly, as you might imagine. One extra cool bonus feature of this is, since mosh sessions are inherently resumable, so long as the client keeps the connection information around, a connection can be resumed even after rebooting the client for a software update. Something I recently did! I was pretty blown away!

One of the best features of mosh for actual mobile usage, though, is its predictive local echo. If you’ve ever been ssh’d into a remote machine with a lot of latency, you know just how frustrating an experience typing can be. Mosh makes a great attempt at solving this by guessing what affect your keystrokes are going to have on the remote session and applies those affects locally before getting the result back from the remote system. It’s obviously not perfect at it, it can’t be, but for a lot of cases, it’s a HUGE enhancement to the mobile experience. This will be extremely useful for instances such as camping on a remote mountain top in Japan using my LTE connection to connect to my shell box on a cable connection in Portland. Something that absolutely will happen.

A downside to mosh is it doesn’t support ssh agent forwarding. SSH agent forwarding is a troublesome topic. It’s one of those things you really want to have, but it’s implemented in such a way that you really shouldn’t use it. There are alternatives, but they aren’t widespread, and they aren’t currently supported by blinksh. I think my solution for this in the long term is to have an ssh agent start on login on my shell box, then I’ll enter my ssh passphrase on first use to add it to the agent. Since the client would be running with mosh anyways, I shouldn’t have to type my password very often, and it should provide adequate protection for my private key.

Mac Mini

Throughout this I’ve talked a lot about my “remote shell box”. In my case, I’m choosing to go with a Mac Mini. Currently I’m using an M1 Mac Mini with 16GB of ram and 512GB of storage. This should be completely adequate me for a very long time, especially when just using it as a shell box.

But why the Mac mini? Why not a raspberry pi? Or a linux box? Maybe even a linux box hosted in the cloud somewhere so I don’t have to worry about VPNs and firewalls and port forwarding and all of that.

There are a couple of reasons. First and foremost, cost. A virtual machine that has those sorts of specs is quite an expensive proposition. I mean, the absolute cost of the Mac mini being factored in means I can buy a lot of VM hours before reaching the cost of the Mini, especially if I do some optimizations like turning the VM off when I’m not using it, etc. So it’s only a moderately important consideration for me.

Another major consideration for me is storage. I currently use iCloud Drive for my cloud storage stuff. I use this primarily because I’ve leaned very hard into the Apple ecosystem, so all of my devices have native support for it. I also pay for other Apple services, so the storage I use with iCloud Drive is pretty much free. I could use dropbox or something else, or even something like syncthing and roll it myself, but I like the safety net of a cloud backed storage mechanism, and my cloud backed storage mechanism of choice is iCloud Drive.

Furthermore, despite being out for a long time, despite “mobile devices” being a lot of folks’ primary experience with the web, there are lots of web interfaces that just don’t work well on the iPad, be it in Safari (my browser of choice) or Chrome. Oddly, one of the biggest offenders is the AWS console. It is literally unusable on safari for some functions, and only just works on Chrome for some things. And I’m not talking about the obscure things nobody uses, I’m talking about first class fundamental features like Route53 or S3. So having easy access (via VNC) to a full desktop web browser is very handy. This is something I could certainly do through other means, but having it be on the Mac Mini means I get things like my 1password database for free without having to load it onto some third party machine (and good luck trying to do U2F via some sort of remote desktop connection, which I need for my 1password authentication)

And finally, there’s part of me that still would really like to figure out iOS app development. I have some ideas for things I’d like to implement, and at the moment, iOS has no native support for XCode. I can’t imagine it’s not in the works somehow, as it would be great to be able to write software for the iPad, y’know, on the iPad, but there’s probably going to be some cloud component to it for compilation and simulation before that can happen, and it’s just one of many projects Apple has in flight. So having a Mac desktop I can VNC into and do some iOS development on while I’m on the road is great.

Hardware keyboard

Not just because I’ve gotten into custom mechanical keyboards during the pandemic, in order to use my iPad as a desktop, I need a hardware keyboard. There’s just no way at all I can type on the iPad screen. Not even a little bit. I can do some mild hunt and peck if my keyboard isn’t handy or if I’m mostly browsing the internet or youtube and need to type in a url or a search term, but for the most part, I need a physical keyboard.

There are many options for this, but I did say I’ve gotten into custom mechanical keyboards lately, so I’m currently using a caseless Corne Chocolate v2.1 keyboard with a pair of nice!nano controllers for wireless bluetooth connectivity. I made it into the group by for the Corne-ish Zen keyboard and am probably going to make that my primary travel board next, and am looking into building some other types of boards to see if I like one or the other better for travel purposes. I’ll probably talk about my keyboard use cases in another post, but I also distinguish between keyboards for “long term travel” (backpacking and traveling mostly on foot) and “short term travel” or “heavy travel” (traveling mostly by not-foot, such as work travel or “heading out to the coast for the weekend” sort of travel)


That’s a whole lot of words, and if you’re reading this, thanks for reading along. I have other things I want to cover about this journey toward using an iPad as a primary desktop, there will be some things that are “this is the definitive way to do this” and stuff like “I’m trying a new thing and wanted to share”. I am enjoying this little experiment so far, and getting more and more confident that I’ll be able to use just my iPad for my future planned “long term travel” (more about that at some point as well).

One thing I do want to say is that it’s unlikely that I’ll be able to use just an iPad for work purposes any time soon. I’m still very much bound to a shell of some sort, and then there’s consideration of device and credential management from employer, consideration of ergonomics of using effectively a tiny laptop display for all of my work, etc, but I would like to eventually give it a solid try! Maybe in a few years once Apple has further converged the iPadOS and MacOS experiences.

Bonus action shot of me working on this post at East Side Coffee

Emacs: a new chapter

I previously wrote about my first month with org-mode. I’m pleased to say that all of that went right out the window and I barely look at Org anymore. But that’s fine. It’s the way of things. Especially with me!

However, today I just did something wild and crazy. I deleted my .vimrc and all associated settings. Emacs is now my primary editor. I’ll of course still be using vim for one-off things, especially on remote servers where I don’t have, nor want my full emacs setup on, and don’t feel like bothering with tramp, but it’ll just be whatever stock config is there. And that’s all I really need out of vim anymore.

Last week I also did something wild and crazy. I switched from using Spacemacs as my base to using Doom Emacs. With that I also switched actual Emacs versions, as Doom recommends emacs-plus on MacOS, where previously I was using emacsformacosx.com.

I’d previously tried switching to Doom Emacs, but reverted my changes. I don’t remember all of the issues I ran into, but definitely enough that it wasn’t a super wonderful experience. However, I think a lot of that had to do with emacs-plus vs emacsformacosx, where the former is recommended and the latter is explicitly called out as being problematic with Doom. This time, I actually read the getting started instructions, and am much happier.

There was a bit of an adjustment period, many of the key bindings are different, configuring doom is *much* different than Spacemacs, etc. But now that I’m settled in it’s starting to feel more like home.

I did this mostly because I wanted to try out Doom and see what all the fuss was about. I don’t really see it as a “better” sort of thing, just different. There are definitely some things I like, and some things that I miss from Spacemacs, but for the most part it’s just a different thing, and now I’m getting more comfortable with it.

Anywho, I’m excited that Emacs is now my standard editor. Like I said, I’ll still use vim quite a bit, but really only in its stock installation form, for quick one-off things or in situations where I don’t want to (or can’t) set up my full Emacs environment.

Alcoholism: not even once

Hi, I’m Jeremy, and I’m not an alcoholic, but…

As I write this, I’m in the LA area helping a friend who is having some serious struggles with alcohol. I have been rather out of touch with this friend for a while so I wasn’t even aware any of this was going on. But Wednesday evening they reached out and Thursday I dropped everything and hopped on a plane.

I don’t even know where to begin.

A bit over 5 years ago, I ended my own struggles with alcohol. I don’t consider myself an alcoholic, but as I describe it: “I had a bad night in San Francisco and decided that was enough of that shit”.

I was visiting SF to attend PuppetConf in 2014. It was being held that year at the Yerba Buena conference center. The night before, I met up with some folks and we ended up doing some heavy drinking and ended up at the bar on the top floor of the Mariott called The View. Named so because of the huge round window overlooking SF from 40+ floors up. It’s a pretty cool spot.

Well, by the time we got up there I was already pretty drunk. I then proceeded to drink more. I remember at one point I tried to buy a round of drinks for my friends, and told the bartender something along the lines of “fuck it, I’ll buy the whole bar a round” and someone next to me said something like “keep it under $500” and I remember just not caring. Fortunately, this bartender recognized that I was not in any position to be making such decisions and didn’t let me buy a round. At least that’s what I’m guessing, since my credit card statement didn’t have a ridiculous bar tab on it.

Later I remember getting rather depressed about a thing. There was a woman there who I was interested in but couldn’t work up the nerve to talk to. I am fairly certain she was there with someone, too, and that didn’t help my mental state. I may have said or done some really stupid things, I have no idea.

Later, I remember very vaguely talking to someone while walking down the street and I think I dropped my phone. I don’t know if the screen had broken, but I vaguely remember being like “fuck it, I have apple care, I don’t care” and spiking it on the ground, thoroughly breaking the glass.

I was staying at an airbnb in soma, so I’m pretty sure I walked back there. I say pretty sure but I’m not entirely sure. I know I walked back. But I don’t know *how* I walked back. At the time I was using Moves.app to track steps and low-res gps track log of where I’d walked. Well, that next day it said I’d walked 33,000 steps. And done a straight line (as the crow flies) from the hotel to my airbnb. So who even knows what happened. For some perspective, my longest Moves.app day ever was about 45,000 steps, walking almost 20 miles in Japan. So even my phone has a vague memory of what happened that night.

I vaguely remember entering the wrong room. It was one of those airbnbs where there are multiple rooms on offer and I was renting one. So the other rooms had other guests in them. I don’t know if I actually did or if it was just a dream (I’d stayed at that airbnb in the past and had worried about walking into the wrong room before).

I woke up later, extremely hungover and quite possibly still drunk. I noticed my phone. I couldn’t find my backpack. My backpack that had my laptop and my iPad. I remember pacing around the hallway trying to find it in the common area or whatever. I don’t know how long that went on, or how quiet (or not) I was being while doing it.

I went back to sleep and woke up around noon. I realized what had happened: I’d left my bag at the bar the night before. So I called and they said they didn’t have it. I’m notorious for forgetting stuff like my backpack at bars and such, so I was certain that’s what had happened.

Meanwhile, the conference is going on. The conference I was spending a lot of my company’s money to attend. The conference where I was hoping to learn some cool new things to take back with me to make me more effective at doing my job. I’d just missed half of the first day because of drinking too much the night before.

All the shame from my actions and words. Actions and words I couldn’t even remember. Feeling like perhaps I got too forward with a woman just trying to attend a conference. Being Yet Another Tech Guy Hitting On The Only Woman In The Room™. Possibly even getting belligerent. Breaking my phone as a flex because of how rich I am. Literally the worst possible person on the planet. That was me. I didn’t want to be that anymore.

After that I was ashamed because I’m walking around with a phone that looks like it’s gone through a blender. It’s the only computing device I have left because everything else was in my backpack which was still missing. I felt like complete garbage.

That evening, I decided. I was done. No more booze for me. I’d lost too many nights to losing control and drinking too much. No more.

I reached out to a friend who was in AA and was like “I think I have a drinking problem.” I still to this day don’t consider myself an alcoholic. For me it’s not an addiction, I just couldn’t retain control of myself when I was drinking. I didn’t want it to turn into an addiction, there’s enough of that in my family, I try really hard to not get into addictive behaviors. She told me some stuff and we talked, and fortunately, that’s all I needed to be able to quit. Also, someone turned in my backpack, so I got my laptop and iPad back.

Basically, I got off easy.

Not so much with my friend.

They’re going through some stuff right now I wouldn’t wish on my WORST ENEMY. And despite wanting more than anything to do literally everything possible to help them, I know there’s only so much I can do. Especially since I’m so far from home. And I know that at some point I have to go home, and I’m super afraid of what will happen after that.

Thanks for letting me share.

A month with Org-mode

People have sang to me the praises of Org-mode for years and years and years. But every time I’ve sat down to try to learn enough Emacs to be able to use Org-mode I’ve nearly had to go see a doctor for the pain in my left hand. I just can’t use the ctrl key that much.

Recently, however, I’ve been working with my shrink on a lot of things, and one of the things she asked about is if I’d tried any task management tools. That opened a whole can of worms and we talked a lot about it, but the long story short of it is that I went home that evening, bought Things for all of the platforms I use, and promptly stopped using it.

The reason I stopped using it was not because I abandoned the idea or because the software is bad or anything. I’m sure it’s great software, and I’ve been doing *plenty* of task management. The reason I stopped using it is because the very same day I grabbed Emacs for Mac OS X and tried to put the hand pain behind me. I haven’t stopped since.

Of course, the story doesn’t just end there. I’m not using stock Emacs, I’m not even using the default-literally-painful keybindings. I got into work the next day, asked a coworker who is a die-hard Emacs user “what do” and he pointed me at Spacemacs. Spacemacs is an Emacs “distribution” (of sorts) which includes a large number of packages and configuration so as to create a consistent and user friendly Emacs platform. It also happens to be targeted at users of “evil-mode” (Emacs VI Layer), which aims to make a very vim-like experience within Emacs. Their tag line is even “The best editor is neither Emacs nor Vim, it’s Emacs and Vim!”. After a month and change, I think I agree with this.

DOGEMACS. Shut up and take my money. Wow.


Org-mode is at its simplest definition, an outlining system. You have headings, subheadings, sub-subheadings, ordered lists, unordered lists, etc. Folks familiar with Markdown are already quite familiar with this sort of thing, though Markdown and Org are actually 2 distinct formats.

But that’s barely even doing Org justice. The real power of Org lies in the functionality that Org adds to the top of it. You can reorganize these headings and subheadings. You can mark things as TODO, DONE, WAITING, or any arbitrary DONE-ness you’d like. You can make checkboxes that you can check off by hitting a couple of keystrokes. You can query the files semantically to extract things like “what’s on my agenda for today” and “what are the TODO items in my backlog” or “how am I doing on keeping up with that new habit I’m trying to form”.

You can also do really amazing things like embed code snippets that are *executable* and even embed multiple of such snippets and have them extracted out as a file in that language for later execution. This in particular is very popular in the Emacs world where people share their configs readily, and folks will write their main Emacs config file as an Org document, publish the document, and extract the actual config out of the document.

My first month

After a few days of flailing about getting familiar with Emacs, with some peculiarities of Spacemacs, upgrading Spacemacs multiple times (the latest official published release when I started using it was over 2 years old, the master branch was several months behind, so everyone seems to just use develop), and tuning my config to my preferences, I started calling myself an Emacs user and started using it full time for nearly any text editing task (ironically, this post is actually *not* being written in Emacs, despite there being an org2blog plugin, but I haven’t quite gotten that far in my journey yet). After years of poking fun at Emacs whenever it was brought up, I now find myself singing its praises. I still poke plenty of fun at it, the default keybindings really do make my hand (and brain, especially as a long time vim user) hurt, but it’s always been all in good fun and now half of the joke is that I’m making fun of myself since I, too, am an Emacs user.

At first I started putting everything I could possibly think of into Org. I have read numerous task management books and whatnot and revisited Getting Things Done and started implementing a “trusted system” in Org. Mostly, I was just trying to get things out of my head. Organize things, try to accomplish things, but even just writing it down would be plenty useful. And it was. I started using Org-habit to track habits like scooping the litter box, making the bed, taking my medicine, and have slowly added things to it, spotted when I was falling behind on a habit(s). I started compiling a list of many of the books I’m interested in reading in the future. I put together a whole directory of the owners in my HOA and used Org to organize a project which required us to get keys to everyone’s units, so involved chasing people down, tracking which board member had whose keys, etc. I’m using it to keep track of all of the documents I need to collect and give to my accountant for my 2019 tax return. I’m using it for general HOA organizational tasks, though that’s only temporary until I find something better that I can share with the rest of our community.

I’m also using Org-journal to try to keep a diary. I’ve been pretty faithful with it, sometimes writing very little, other times writing very long winded entries. I spent the afternoon of Jan 1, 2020 writing up a bit of a “what I want to get out of 2020” and some “resolutions” for good measure. And I’m using org-habit to make sure I review that document periodically.

I’m also starting to really figure out what I want to use it for at work. We already use Jira, so using it as a general task management tool is probably not super great. And since I don’t have shared storage between my work computer and my personal computer, it’s hard to really have a unified Agenda between them. But what I’ve started doing is keeping a running log of what I’m doing for a certain task, ticket, or in the case of this week, I’m secondary on-call, so I get to deal with business hours questions in slack and also triaging (and trying to keep up with) new toil-like work that comes in via our ticketing mechansim. I plan to publish these logs (in Org format) to share them with my team and also for oncall weeks as a type of handoff document. I’m also using these to track follow-up work within a project, such as updating provisioning documentation when provisioning a new thing, or scheduling work that’s related to the ticket but should be done later such as deleting backups after a certain period of a time for a decommissioned service.

So, yea

I actually had a whole other post partially written that was probably 10x longer than this already and went into great detail about each individual thing. Part of why it’s taken me so long to write this is because I wanted to pare that down a bit before publishing it since there was just too much detail. I may write up individual posts about some of those things in the future, but it was too much to put all in one place.

What’s amazing though is just how much using Org has transformed how I do things. I wake up in the morning, I consult Org. I check off my morning routine tasks, I check to see if there’s anything I need to do during the day from my personal list, go to work, pick up Org there and do more things, etc. It is slowly starting to consume my computer time, and that’s not a bad thing. In fact, if it has the effects I want it to have (feeling more organized, more confident, able to get more things done), then by all means, consume away 🙂

The future

There are a few things I would like to focus on next.

Primarily, I now have way too much stuff in Org. Or at least, way too much stuff in Org to be able to really reason about it all at once. I’ve kinda shoved everything from my brain into a big pile in Org, loosely arranged some of it, and now I have just a big mess again. It’s at least not in my brain, but part of the benefit of not having it in my brain is trusting that I’ll be able to “remember” it later by looking through my Org (this is one of the core components of the GTD “trusted system”). But I’m starting to fall back on old habits. Not consulting Org for “what’s next” sort of stuff. Primarily because it’s just a jumble of mess right now and hard to reason about. Not checking in with Org in the morning as much, primarily because the morning routine habits I wanted to form using Org have mostly formed, so I get up, make my bed, take my medicine, scoop the litter box, etc, and I don’t have to consult Org to remind me to do those things. I just do them. So getting my Org more organized and usable is definitely high up on the list. A lot of this I think is just going to be “reducing work in progress” and axing projects and such, but I want to put them somewhere such that they’ll naturally surface again at some point and not just because I thought about it one day and then feel bad that I “forgot”. I *think* this is the function of the “tickler file” in GTD? But I haven’t gotten back around to that part on this read through.

Now that I’m more comfortable with Emacs and Spacemacs, I kinda want to look into alternatives. I’m subscribed to several Emacs subreddits, and one of the things that keeps coming up is Doom Emacs which is also a vim-oriented Emacs distribution and seems to be pretty popular. Spacemacs is great, but I find it to be rather buggy at times and have run into some issues. So I’m not exactly married to it. But also maybe I’ll just like how Doom Emacs feels better than Spacemacs? I dunno. It doesn’t necessarily have to be one is better than another, just more my style. I may even try to roll my own thing from a stock Emacs config, just to learn some of the building blocks like use-package, which might make it easier for me to hack on Spacemacs or whatever combination of things I end up using.

I also want to learn more about Emacs Lisp in general. I sorta understand Lisp, but right now a lot of it is just cargo culting and I really have no idea what I’m doing. It might also make it easier for me to use one of these larger distributions if I am better able to understand the code I’m reading or how all the parts fit together.

Part of wanting to learn more about Emacs Lisp and hacking on this stuff is so I can do some ham radio things with Emacs. I feel like Org-mode seems like a great place to put things like radiograms, perhaps a winlink client (or, more likely, an api client for pat), maybe some Org functionality for net control stations, I dunno! Could be fun.

Mostly, though, I just want to keep finding more things I can use Emacs and Org-mode for and do those things! Hopefully my “A year of Org-mode” blog post will have been composed entirely within Emacs, somehow or another.

What’s Up?

Been a while since my last post. So here are some updates:

I’m no longer at Cozy. I’m at Squarespace now.

Speaking of web hosting, I finally moved this blog over to WordPress.com so I don’t have to worry about my WordPress site getting owned and all the updates and maintenance required to run a stagnant site. So for $50/year I’m hosting it over here for now. Yes, I work for Squarespace. Yes, I could host it there for free. It was *super* easy to migrate it to WordPress.com, so that’s what I did. 🙂

I’ve switched to using emacs as my primary editor. Those who know me would probably either be incredibly surprised (I’ve been a vim user for a very long time, and have made fun of, and still make fun of, emacs, regularly) or not even the slightest bit surprised (I have a habit of changing my mind on things and going all in on the new mindset). Mostly, though, I had another round of “I want to have Org-mode be part of my life”, and, with the help of a coworker and Spacemacs, I feel like it’s going to stick this time. The great thing about Spacemacs is it’s so familiar because it’s using evil-mode (vim keybindings) and so discoverable because it will throw up submenus when you hit keybindings, so very easy to explore functionality and such. It’s rad.

I have had a pretty lazy couple of years since I was on the trail in New Zealand, but I’m planning to get back on the trail for a bit this spring. Current plan is to hike a section of the AT, starting mid to late April, starting from Harper’s Ferry, WV for 2-3 weeks (depending on how much unlimited vacation I feel like burning and whatnot). I’m really excited about this because I haven’t been on the trail in a long time, and I feel like I really need to have more of that in my life! I thought about hiking more in Japan, but this year I kinda want to not have ridiculous long flights for vacations, as I’ve been doing a lot of long international flights the past couple of years and despite some of them being business class and such, it’s just a slog, and I think I’ll pass this year. Plus with Squarespace I’ll be flying to NYC periodically, which is a fairly long flight, as opposed to SF which is not, so I just don’t want to have so many hours of my life spent on planes.

Since my last post I have worked 2 Cycle Oregon Classic events. I have a very old draft in here of a write-up about the 2018 ride, and I have another one in my ham radio blog about the 2019 ride. I’m unlikely to ever publish either of them, but I do want to write up something about my vehicle setup for the event and the stuff I’m doing with mapping and my iPad for helping me during the event.

Speaking of mapping and iPad, Apple came out with PencilKit, a drop-in pencil drawing layer you can use for making apps with and let them do a lot of the heavy lifting regarding handling user input and rendering and whatnot. It’s pretty cool. I thought it would make my dream goal of having a mapping app a la Guru Maps with the ability to draw directly on the map with my Pencil almost a trivial one to obtain, but I’ve run into some difficulties with it and am having to take several steps back and learn more about iOS development and how UIKit works and such before I can step forward again and try to make it a reality. I am confident that I can make it happen, and am looking forward to learning everything I can along the way.

Speaking of ham radio, I launched a ham radio blog last year while I was doing net control duties for the NET net. I’ve got a few posts up there talking about Winlink and such, and hope to have more things up there soon. It’s kind of a dumping ground for things I’m doing with ham radio and maybe some howtos or guides or whatever for getting things set up. It’s been fun to have it at the very least.

I also bought a condo at the end of 2018! It’s a one bedroom with a nice sized basement (storage / workshop / laundry room sort of thing) and I’m really enjoying the place. I’m also now the president of my HOA which is crazy, considering I’ve been to maybe 4 HOA meetings ever, one of which I was the president of. Hah! But I stepped up because we didn’t have a president for a while and we have a huge huge huge renovation project going on right now that needs managed, and the 2 other members of the board were doing a lot of work with it and seemed like they could use a hand.

Anywho, I’m looking forward to 2020 and getting a bunch of things done in my life and some projects and all of that. It should be a good year.

New Job!

I have a new job! Like, a real one!

On Monday I’ll be starting at Cozy!

Cozy logo

Cozy is based in Portland, and is a very small company with big ambitions. They are trying to change how tenants and landlords interact, and make things a lot easier. From the initial application through lease signing to paying rent and beyond.

I’ll be on their Operations team, managing production, managing deploy toolchain, etc. It should be pretty fun!

It’s also a departure from working remotely for me. As I’ve talked about in previous posts, one of the big things I felt was missing in my life was direct human interaction. So, I’ll be getting a lot more of that soon! There are other benefits as well, and not just Benefits, but I mean a lower stress working environment, where “take the site down” level mistakes don’t (necessarily) mean millions of dollars of impact, or massive amounts of recovery work on the part of the rest of the company. It doesn’t mean I can be reckless, but it means I don’t feel like I need to tiptoe so much around making changes.

The commute is fine, about 25 minutes on my bike, with moderately good bus connection should I want to not ride. I plan to move from where I’m at, but it likely won’t be that much closer, and definitely not *too* close. One of the nice things about having to go into the office every day is the context switch that comes with leaving the office and going home. Or leaving home and going to the office. Instead of getting up and walking to my couch to start working, I get up and get to have some sort of morning routine before heading to work. I am looking forward to that aspect of things!

I’m pretty nervous, because it’s been a long time since I’ve worked in an office full time, and it’s been a long time since I even worked, but I felt pretty good about the interview process, and I feel like they’re a great group of people to work with!

How I’m learning Spanish

I just hit my 30 day streak in Duolingo, so I thought I’d go over the tools and resources I’m currently using in my Spanish learning journey. I’ll start by simply listing them, then going into a bit of what they do, why I’m using them, etc. Also I want to talk a bit about my process, my “daily routine” so to speak, and what I’m hoping to find in the future to help me learn.

Current tools

These are things I’m currently using actively. Maybe not daily, but actively.

Easy Spanish Step by Step

I gotta admit, I was skeptical of this book. It feels very “Learn <something super complex> in 24 Hours” based on the title alone. However, it came well recommended, and it has been a great resource for me so far.

For me, reading is the gateway to learning just about anything. Better if said reading walks me through the learning process. Reference books are amazing, but tutorials are better. This book is much more about what to learn in what order than how to actually go about learning it, but once I stopped searching for an Anki deck that covered the stuff covered in this book and just started making my own cards, it became a lot more useful to me.

There are points where it just lists off huge lists of vocabulary. If you tried to read it cover to cover in one shot you wouldn’t retain anything. You’d probably be completely lost by the end. There actually might be a good reason to do a first pass, cover to cover, before trying to actually retain any of it, but that’s not how I’m using it. I’m walking through chapter by chapter, using it as a source of new Anki cards and explanations of concepts and knowledge. It introduces ser vs estar in the second chapter, which also introduces verb conjugations as a concept, all of which are *incredibly* important parts of Spanish, at least as I’ve gathered so far.

Good stuff. I’m on chapter 4 I think? I’ve been trying to avoid pushing forward on it until I’ve caught up with all of my Anki cards!


I tried using this several years ago as my primary (only?) tool to learn Spanish and it just didn’t stick. It didn’t really go into any detail as to why things were the way they were, I guess hoping you’d either look it up once you noticed the pattern or something? Like it will show “we eat” on “nosotros comemos”, but doesn’t show you the list of conjugations of comer or anything. I think they literally just within the past week or so changed that, however, as each lesson subject seems to have a little description box next to it you can click on and it’ll talk about the things the lesson will teach you.

I like it because it’s gamified. It is a great source of new content for my Anki cards. It gets me thinking less about individual words and more about sentences and phrases. I also like that it has some components of listening practice and has “what’s this is Spanish” as well as “what’s this in English”.

It has a speaking component, but I find it to be fairly buggy in its actual functionality. The number of times I have felt like I spoke the words perfectly and it rejected it to the point of saying “let’s move on”, as well as the times that I’ve messed up half way through and gone so far as to spew gibberish for a couple of seconds to hopefully force it to fail so I can try again, or the times I’ve literally said nothing and it’s been accepted, leads me to believe it’s not the greatest thing. But it *does* get me to actually speak the words out loud, which is good, and I do, so that’s good.

The questions are very repetitive and sometimes even directly duplicated within the same lesson. “How do you say ‘the baby'” is a good example. I’ve seen that question come up 3-4 times in one round at times. Up to level one of each topic seems to be a way to introduce you to the new things, with the first half of each round being introducing them and the last half being to review, and past that, repeating lessons is just repeating the same things, so what I’ve been doing is get to level one in a subject, add all of the stuff to my Anki deck, and do one lesson a day per category, with lots of active (not yet level 5) categories going, and pushing forward with new subjects (or a chapter of the book) when I run out or run low on new Anki cards in my deck.

It’s likely I’ll be dropping this at some point, as Clozemaster, which claims to be a good “post-Duolingo” tool, may in fact be a replacement for Duolingo for me, but I’ll talk about that more in its section.

It has groups and friends and such, and a “pro” subscription to remove the ads (this is actually a good counter-example to my ad-supported -> ad-driven argument, and a reason I still use it, despite the ads), but since I’m currently doing this mostly on my own, those things are lost on me. It has a “practice” mode, which … I think shows you random questions from all of the content you’ve “learned”, but I’m not sure how mixed together those things get or if it’s just a random selection of questions from your topics. I don’t use it much, unless I feel like grinding on some questions for a bit, as I tend to try to do more new Anki cards if I get bored and want to do some more practice.

Overall I’d say it’s a decent tool, and a great onramp, but it should not remotely be the only tool you use, and don’t expect to be fluent after you complete your tree. And if you have any sort of “but why” question, look elsewhere for those answers.


Anki is a general purpose flashcard app. At its core is the concept of “spaced repetition”, which tries to show you cards again at the point just before you’d forget, to more strongly reinforce the material in your brain. It’s cool. It’s extremely flexible, which can make it hard to get started, and it was easy for me to get distracted by trying to figure out how to make a shared deck I grabbed for the book do what I wanted (and nearly made me stop trying to learn).

The biggest piece of advice I can give on this subject is: make your own cards. You’ll eventually figure out what you want on your cards / notes. Also, notes are kind of like the facts, and cards are the things that test your facts. It’s a one to many relationship with notes -> cards, though the UI doesn’t do a great job of making that clear.

Speaking of UI, Anki’s is fairly terrible. The actual “I want to practice my flash cards” interface is great, at least on the iOS and MacOS versions. There’s a sync service that enables you to sync your decks and practice information, and it’s all very functional, but not the most highly polished thing. Also, for many of the things you’ll likely want to do with Anki, you’re going to need a computer. The iOS app (I don’t have any android devices so I don’t have any opinions there) is good for creating new notes/cards if you’re only doing very basic front/back types of cards with no multimedia content and not using custom note types or multiple cards for notes or anything. It is, however, very good for studying. It shows you a card. You tap on the screen to see “the back”, you tap whether you got it right or not, and varying degrees of got it right, and it takes you to the next card.

Anki has support for hints, for multimedia (at least audio, and I imagine images at the very least) and the cards are *extremely* customizable. There is support for plugins, but I’m not sure how those things play out when talking about mobile apps. I try to stick with the most vanilla of features and don’t use any plugins. There are some plugins that seem like might be useful, so I might check them out in the future, but for the moment I’m getting by fine.

I started off with just basic front/back. But then I realized I wanted more. For instance, with nouns, the book (in Chapter 1) mentions a bunch of, not so much rules, but more hints about the gender of nouns. Like nouns ending in “-a” tend to be feminine. Some nouns can be both, and you sometimes change “-o” to “-a”. But the biggest thing it mentions is that these aren’t hard and fast rules. There are exceptions. So you really need to learn the gender along with each noun.

So, in my brain, that’s actually 2 things I want to learn about each noun. What it is, and what gender it is. And I might want to do that separately? So I did. I changed the note fields from Spanish/English to Spanish/English/Gender. I made these a separate note type just for nouns so I could then make special cards just for these notes. One shows the Spanish (including gender, just because) and asks me what the English is, and the other shows me the Spanish and a little blank just before it, prompting me to answer what the gender is. I used to also English -> Spanish, and pronunciation, but the English->Spanish cards I think I want to mostly avoid, and the pronunciation cards were kinda redundant, as I was pretty much always speaking things aloud as I read them, no matter if it was a pronunciation card or not, and culling these cards cut out a pretty significant amount of the cards in my deck, which means I have less new cards going at any given point, so I should be able to cover more content.

I’ve done this same sort of thing with other types of word, too. Like I have one for verbs which helps me practice conjugations of the verb, but I also just culled most of the regular verbs from the deck, at least the conjugations, simply because I had 7 different cards for each noun and it was getting ridiculous. I added a couple of notes that covered “the rules”, and I continue adding irregular conjugations, so I’m practicing the oddballs while hoping that learning and knowing the rules very solidly will help me with the rest. Additionally, as I start learning more conjugations, I’m going to want a better tool, as there are just way too many conjugations to try to have an anki card for each one. Wayyyyyyy too many.


Speaking of better tools for conjugations. One of the features of Clozemaster that I haven’t yet played with is conjugation practice!

Anywho, Clozemaster is a tool I saw mentioned in an /r/LearnJapanese post (I previously was trying to learn Japanese, and the subreddit is still interesting enough that I subscribe, but it’s mostly an in-one-ear-out-the-other sort of thing) which combines a large phrase library, an ordered list of words, and clozes into a tool to help you learn languages. Clozes are a new thing I’d never heard of before, but something that Anki does support, too. They are “fill in the blank”. It shows you a sentence with a space missing and you choose or type in the correct word. Awesome.

Currently, my Anki deck is mostly this -> that sort of things. There are a few sentences and such in there, especially ones trying to cover some aspect of the learning process (ser vs estar, for instance) but it’s to the point where I mostly just know the answer based on what the card is, not so much the concept that is at play. It has been useful for some things, but I feel like I need a LOT source material to be effective, and I just don’t have that right now. However, Clozemaster does. And it comes up with sentences for you. And has spaced repetition stuff built in, though I’m not certain how best to use it, I feel like I can’t make a dent in my reviews queue and that things keep getting repeated. But I’m sure I’ll figure out how best to use it eventually, it’s only my second day using it after all.

It does a couple of things I am not getting elsewhere at the moment: exposes me to a *lot* of words I don’t know, especially conjunctions and such. It also exposes me to lots of different verb conjugations. I couldn’t tell you whether something is a past subjunctive or a preiterate indicative (are those even things? See what I mean?), but I can see a conjugated verb, identify the stem, and suddenly at least know what verb is in play. Which may not be the best way to learn conjugations, but it gets me reading more sentences and such, which, again, reading is my gateway.

On the subject of verb conjugations, it has a conjugation practice function. I tried it, but since I have such a limited verb set right now and relatively few conjugations, it’s totally lost to me. I want to see if there’s a way to limit the verbs being used to a subset, and the conjugations, but for now I can just look forward to the day I add that to my daily routine.

It also has a feature for “tough grammar points”. In the book it introduced early on ser and estar and said when to use which. Of course, that was a while ago, and that all went completely out the window since I wasn’t practicing it. Oh, I knew what the conjugations were, but I didn’t know wheter I wanted están or son, or somos or estamos or what the rules were. Since the book had some exercises that covered these exact things (with Clozes) I just plopped those into Anki (not as actual clozes, I haven’t tried using that feature yet) and drilled on them. It was effective. But again, I’ve started learning more the correct answer for the card rather than practicing the rule. I just don’t have enough material, and coming up with sentences is difficult. But here we are, exactly the thing I wanted. Oh, and Clozemaster also introduced me to “haber”, which is the verb “to have”. But “tener” is also “to have”. So in my notes, there’s literally a “tener vs haber” checklist item, in there as a “figure out when to use which and make some anki cards to drill that”, but there, in the “tough grammar points” section, tener / haber practice. Glorious. I plunked down for the annual pro subscription almost immediately.

By default, when it shows you a cloze it has the English translation underneath. The English translation is quite often necessary, to even know what word is being asked for. Sometimes you can figure it out from context (which is part of why clozes are awesome), but there are literally clozes in their library that are one word, so when they show up it’s just a blank line saying “what goes in here?”. Not very useful. However, I found when I was reading a card, I would read the Spanish, and I was trying to figure out what the Spanish said, but my eyes would drift to the English translation directly below, meaning I would not really even read the Spanish, and I would mostly just try to figure out which English word the cloze was asking for and enter that one. This isn’t useless, but I didn’t feel like I was getting as much value out of it. Fortunately, there’s a setting which allows you to change whether or not the translation shows up, and when. Right now there are 3 options: always, only after you’ve answered, and never. The only after you’ve answered option seems to be a bit misleading, because while it definitely does show up after you’ve answered, you can also show the translation prior to answering by tapping, which, as I’ve already said, is often necessary to even be able to answer. This is the option I’m currently using, and in the short amount of time I’ve been using it, it has improved my experience. I read the Spanish. I try to figure out what it says. I try to figure out what word it’s asking for even before I look at the multiple choice list of answers below (there is a “type your answer” mode, but given that I’m often dealing with verb conjugations I don’t yet know, I opt to stick with multiple choice for now), and if I can’t, I’ll show the translation. It has been immensely useful already, and I’ve seriously only been using this site for 2 days. Shut up and take my money.


It’s a dictionary. You can go Spanish to English or English to Spanish. It does some translation stuff, but I usually just use Google Translate if I’m looking up more than just a word.

It’s where I source the audio files for my pronunciations in my Anki deck, as they are real humans speaking the words (which sometimes has funny results), and I feel like that’s very important. It’s especially useful for “g” and “c” sounds, because I’m not sure if those are always consistent how they’re pronounced from word to word, and if they are I certainly don’t remember the rule (though I know where to find it if there is one, Chapter 1 of the book, actually maybe even the preface), but monkey-hear-monkey-speak is very useful as a check to make sure I’m pronouncing things as well as I can.

It’s also where I look up verb conjugations. On the page for each verb there’s a “conjugations” tab which lists out every conjugation for the verb and highlights any irregularities. Amazing. Terrifying that there are so many, but amazing that this exists and is so well organized.

There are also articles going into various aspects of the language, like possessive adjectives or negative and infinitive words, which is really REALLY handy to me when I start noticing a pattern in some words and want to know if it is actually a pattern and if so, are there rules that govern the pattern that I can apply more generally. I’d much rather know the why rather than just the what, and this supplies a lot of that.

My only real complaint with it at the moment is that it seems to have a pretty sizable space for ads on each page, and while ublock is effective at blocking them, it has whine-text about me blocking ads. So, while I find it to be a very useful tool, and it’s also another counter-example to my ad-supported/ad-driven thing, the size and number of the ads leads me to believe they would be distracting, terrible ads, rather than unobtrusive text ads or whatever, and so I won’t be unblocking the ads. I’d love a way to give them some money, because it has certainly been a very useful tool for me and will continue to be going forward, but showing me ads is not the way they’ll get that.

Update: I did end up finding a way to give them money, they have an iOS app which is actually quite good, and that has a $2.99 annual subscription to remove ads, which seems to also remove them from the website if I’m logged in. Cool!

El País

It’s a news site. I’ll pull this up sometimes and look at headlines. I am mostly using it right now as a way to gauge how much progress I’m making. The more of the text I can understand, the better I’m doing. And eventually it’ll probably just become a part of my daily routine to read a few articles, as I get to the point where I can read most of the words and not just get vague ideas of what’s being said. Again, reading being my gateway, this is something I want to keep available to me.

Past / Inactive tools

There are a couple of things I’ve come across in my journey which I don’t use anymore for one reason or another (most likely they just didn’t really stick) but I think are worth mentioning.


Readlang is a site where you specify what level of Spanish you’re at and it’ll show you text that’s been rated at that. Letters from people, snippets of books, whatever. I’m not actually sure what all they have, but it seemed pretty awesome. Their trial to paid barrier is pretty fierce, so it’s not something I’ve played with very much, but it does seem really cool. The first thing I “read” in Spanish was using this site and it filled me with an immense sense of pride that I’m making some progress. You can highlight words and phrases inline and it’ll translate them for you and even go as far as to create flashcards (in its flashcard function) for the stuff you’ve highlighted. Super cool. I do hope to revisit it at some point, but it wasn’t mind blowing enough for me to plunk down right away on, and the pay barrier is too low for me to get enough out of the free functionality to keep me using it even just a little bit as part of my routine.

Daily routine

Right now my daily routine is to go through all of my active subjects in Duolingo and do one round of each of those. I usually do this early in the morning while still in bed cuddling with Bean (my cat). It has replaced my early morning reddit and google news perusing, so that’s a positive, I guess?

At some point during the day I’ll go through my Anki stuff for the day. If I am feeling up for it, I’ll generally do another round of new cards, just because I have so many of them that I really would like to go a bit faster through them if I can. I don’t want to burn out though, and I feel like there are diminishing returns on churning through new cards, there’s only so much your brain can take on at once, so keeping the new stuff fairly limited is probably not a bad idea.

And now that I have Clozemaster, I’m going through and hitting my goal on that for the day, which is 500 points. I think I may have gone a bit overboard with the “new” questions on the first day, and now I have a big pile of reviews, but I’ll work my way through those, too.

During the course of doing all of this I have a little Notes document where I take some basic notes. It’s more of a todo list than actual notes. I mostly use it for new cards I want to make in Anki (like if I learn a new word from one of my sources) and I’ll jot down ideas for either improvements to my Anki deck or to my process.

Sometimes I’ll pull up El País and see if there’s anything interesting or readable on there, but it’s not really part of any routine just yet. It will be, though.

The future

Right now one of my goals is to make it to the end of El principito, the Spanish translation of The Little Prince. I’ve gotten through about 3 paragraphs so far! I haven’t read this book before in any language, so I think it’ll be a good challenge, but not one that’s too hard. For some reason in my searching for easy Spanish language books I kept finding Don Quixote, which is *not* an “easy” book to read, in any language.

I need to figure out some way to practice listening. Duolingo has some basic listening stuff, and you can make it so those are the only questions you get, which I’ll probably do, but I want to do more “real world” listening. There are lots of podcasts for Spanish learners, I’ll probably find some sort of Spanish language video news source I can watch some of, etc. It’s certainly going to be a challenge, and I’m not really sure how to approach it other than “listen and try to find bits and pieces you can understand, and keep doing it”, but it’s far enough away at this point I’m not too worried about it yet.

Eventually I want to do actual speaking, too. Preferably with a native Spanish speaker. There are various apps online which can help connect you with a partner to “trade” language learning with, like HelloTalk, and there’s always the option of finding a tutor.

From there it’ll probably be starting to attend local Spanish learner’s meetups. This is going to be super scary, but I can only imagine these things tend to be pretty newbie friendly, or they have newbie friendly sessions or whatever. I’m excited about the idea, but also a bit terrified. I don’t expect this to happen for 3-4 months or more, and maybe that’s even being optimistic. I’ve never learned a new language before, so this is all new to me! It’ll be fine, though!


Ok, that’s a lot of words. I’m going to stop for now. If you’ve made it this far, thanks! I hope it was interesting!

Excitement, etc

So I just got rejected for a job. In seemingly large part due to my last blog post. From the feedback provided (which is totally awesome that they did this, btw, because it’s not just a “good luck in your future endeavors”, it gives me something to think about):

I just didn’t have confidence that you’re excited to come back to systems work. Uncertainty in your description of why you chose to leave your last job left me doubting that you knew what you wanted, and were committed to and excited for the opportunity to join our team.

Hmm. So, I can totally see that. I left NationBuilder because I was completely burnt out. My tenure at Stripe had many things stacked against me, and the recovery I wanted to have happen just didn’t work out.

But I’m not sure I agree that I’m not excited to go back to work. I would absolutely love to find a job where I can be happy and feel like I’m contributing to a team and maybe helping make the world a better place somehow and helping to provide people with a product that they enjoy using. A lot of my time on Te Araroa was spent trying to figure out what was wrong, what was missing. And I learned a lot about myself and what I wanted and what indeed was missing.

In this job search I’ve been focusing solely on jobs in the Portland area. I moved to Portland while I was working at NationBuilder and was remote with them for the rest of the time I was there. It worked out ok. I had been introduced to some people up here by mutual friends and was enjoying myself. I got super burnt out from work and lost the passion that had me going to meetups, various things happened and some of my friends drifted away, and combined with my usual shyness and social anxiety, I ended up becoming extremely isolated and lonely.

I started at Stripe super excited about the job. I don’t think I’ve ever been so excited about a job. And to some degree, that was the beginning of the downfall. But one thing my time at Stripe taught me is that I actually enjoy working in an office with people. My visits to the SF office were invigorating. Talking to people in person, socializing during meals and after work, etc. But I can’t stand San Francisco. It’s just not somewhere I could ever live, for a lot of reasons. So I got this taste of awesomeness, but it was tainted with sadness that it couldn’t be all the time.

On the trail I thought I’d be fine by myself. I was the last 2 trips I’ve done. And surely I won’t be *that* lonely, I’ll probably be meeting plenty of southbounders and we’ll probably have some overlap at huts so we can hang out there. And I had some of that. What I wasn’t expecting was the “trail family” that came together out of a handful of northbounders who happened to be pacing roughly together for a week or so. At first I was afraid, afraid of judgement, so I kept them at arm’s length. But eventually they sucked me in and I felt like part of a group. It wasn’t until the group split apart with some people doing side trips, some people staying back, some people forging ahead, and I was alone on the trail again that I realized what I’d been a part of and just how much I enjoyed that.

Later on I’d reunite with a couple I’d met very early on in the trip and we’d spend a week together in the Richmonds. It was then that I found out that I still did like being alone sometimes. I would often intentionally get up later than them or whatever so they’d get a head start and I could have some alone time on the trail. Eventually I’d either catch up to them or I’d see them at the hut at the end of the day. It was great to find that balance.

What all of this told me is that one of the big things that was missing was working in an office with people. Maybe if I had a well established local social life outside of work I could work remotely and be fine. But I don’t have that. So I think I need to work amongst people again.

The main reason I’m also exploring other things is that for a good portion of my time at Stripe I was really struggling, and trying to figure out what I could change to improve my life. What was missing? I’d been wanting to ride my bike across the country for years, and my spontaneous decision to travel to New Zealand and walk around for 4 days got me hooked on backpacking. My “fallback” then was “I’m just going to go walk somewhere or whatever.” However, I also wanted to make that a thing that I actually did for more than just 1-2 weeks while on vacation or something. So I then worried about things like when am I going to have the time? I need to save super aggressively so I can do a mini retirement or extended sabbatical (read: 1-2 years), or whatever.

So while I was there I was worried about my work performance, super lonely, and afraid of alternatives. But I wasn’t doing anything to solve any of those problems, I was just stuck in a loop of worry.

The Te Araroa trip helped be break that loop. It also helped me figure out what I was missing. Or at least some things I can try, as opposed to just recognizing that something is wrong and worrying about that. So, if anything, I’m actually more excited about the idea of going back to work than I have been in a long time, maybe even as much as I was about going to work for Stripe. Now, that’s not to say I am as excited about any particular company, but I *am* excited about going back to work, meeting new people, learning new things, and seeing if my changes make a difference. A best case scenario would be finding fulfillment and happiness that keeps me in Portland, with the occasional bit of continent hopping of course, but one that helps me make a connection with a community, be part of something.

One of the other things the trail taught me I was missing was a creative outlet. Sure, building stuff with computers is creative, sure, but there’s a difference between creative for work and creative for fun. I’ve tried lots of things. Knitting. Learning a new programming language. Trying to build a website about interacting with friendly cats around town. Ham radio stuff. Whatever. And none of those things has really stuck, for various reasons. Knitting and programming because while I could learn the basics, and did, I never could figure out what I wanted to do with that knowledge. Other things had other forms of Resistance which contributed to the project or hobby ultimately resulting in failure. And because of those failures, I am hesitant to try something new, afraid to add another failed idea or project or hobby or goal to my long list of those. But the trail taught me that it didn’t matter. I needed something. So I’ve been exploring a bit. I’ve been trying to explore something that can be practical in a “Plan B” sort of scenario. Hence, Spanish. And my “Plan B” is actually the creative outlet itself. Not only am I learning new things, figuring out logistics of whatever, thinking wild thoughts like “maybe I could get someone to pay me to write a book about trails in Japan” or whatever, but I’m instead of *worrying* about what my Plan B might look like, I’m actually creating the Plan B. During my NET training one of the things they taught us was giving someone something to do, no matter how trivial or seemingly unimportant, can help them handle the stress of the situation they’re in. The act of exploring possibilities helps me focus my energy on creativity or problem solving, rather than just worrying about what if.

The idea of going back to work, with all of this newly gained wisdom, and testing the results is extremely exciting to me. And if it doesn’t work out for whatever reason, well. There’s always Plan B.