Olly Headey

November 10, 2022

Products I use to manage work and life admin


To friends and family I’m thought of as a proper techie, but to the real techies I know my tech-fu would be considered rather weak. This is fair. I like using tech to get stuff done and make my life easier, but I don’t really go for nerding out on tech for the sake of nerding out on tech.

I manage my work and my increasingly-overflowing plate of life admin almost exclusively in digital form. I have a pen and a variety of notepads in my desk drawer, but they don’t get much action, sitting there in lonely solidarity alongside the staples and micro-USB cables.

I thought I’d write a list of all the apps and tools I use so in years to come I can look back and marvel at how things have changed, what tools survived, and what bit the dust. Some things have been on this list for over a decade, so a lot of the things I use are robust and built to last.


My work laptop is a 14” MacBook Pro M1 Pro with 32GB RAM in Space Grey, mainly so I can differentiate it from my personal laptop.

At 37signals we use Basecamp almost exclusively for communication and project admin. We have HEY for Domains, but we hardly use email. I use it to read the Basecamp Latest Activity email each morning, and the odd email to an external vendor. We also have a Google Workplace account which we use for SSO, and I occasionally use it for spreadsheets (tabular data in Basecamp isn’t really possible), but that’s it. It’s a marvellous, refreshing way to work and unless you work for a larger corporation, I suggest you give it a try.


To Do lists are central to Basecamp, but for keeping track of my own private list of work stuff I use Microsoft To Do. I was a fan of Wunderlist in the distant past and (I think) it morphed into Microsoft To Do after Microsoft acquired it. I really like it. It’s a fast, simple app that I can chuck stuff in quickly. Done ✅

For keeping track of all my work notes, 1-1s, team calls etc, I use Notion. I like Notion, it’s great at what it does. It’s arguably overcomplicated for what I need, but I’m kinda committed now. It’s really fast, so I can just chuck stuff in there and (usually) find things easily. I can keep things neatly organised (unlike, say, Google Drive - urgh). I don’t put all this stuff into Basecamp because I consider it private. I also use Notion for my own personal work stuff, e.g. side projects/gigs, house etc.


When I’m writing code I use VS Code. It’s great. I went from TextMate, to Sublime Text, to VS Code - each one better than the other. The plug-ins are amazing. I use Github Desktop because it helps me better visualise what I’m about to commit than the terminal view does. For terminal work I use iTerm2 and ohmyzsh out of the box. 

I currently use the Arc browser for work. It’s based on Chromium so all my plug-ins work, and I get the Chrome dev tools. It’s taking a bit of getting used to but I really like the Cmd+T workflow and having tabs in the sidebar.


I have a personal laptop – a 14” MacBook Pro M1 Max with 32GB RAM in classic silver. You can go all Don Johnson and get a white Ferrari (with matching suit), but you know deep down that a classic red one looks better. It’s the same with silver MacBooks. Bite me.


I have an Apple Studio Display which I use when at my desk, with the MacBook Pro closed. One screen is enough for me, and what a screen! I love it. I paid more for the adjustable height monitor because why would I want to put a shonky Amazon monitor stand or some books under it to get it to the right height? That would be a crime against the minimalistic vibe I’m going for. I use an Apple Magic Keyboard (the one with Touch ID) and a Magic Trackpad. I tried using a mechanical keyboard but I didn’t like it. I find the Magic Keyboard more comfortable, I type more accurately and it looks better (see above: I’m not a real techie).

I’m all-in with Apple. I’m a fanboy, sure, but the alternatives (Windows, Android, Linux) are too painful to think about. I have an iPhone 13 Pro an iPad Pro 11” (M2). I use the iPad and pencil for editing photos in Lightroom CC, and I create mixes with Traktor DJ. It’s also great for reading magazines via Libby.

I use Safari for browsing. It syncs between all my devices and gives me Apple Pay and Touch ID, even on my Mac. For random notes I use (you guessed it) Apple Notes, which are handy for sharing lists with my family. I use Apple Reminders for keeping track of all those life admin things to do but to be honest, I rarely look at it. 

I use 1Password religiously, and I’ve indoctrinated my family into the cult. It’s wonderful, perhaps the most useful bit of software I have. A genuine “how would I live without this” app. Don’t think about saving a few ££ for LastPass. You get what you pay for.

I’m old school and I seem to have my fingers in lots of pies, so I deal with a lot of email. Emails from the kids’ schools and clubs, bills, business, all that. I actually really like email! I use HEY for all my email now, but the majority of emails still come through my domains, so I have an account with Fastmail which handles SMTP. I just use HEY as the client. I tried to make HEY for Domains work, but it couldn’t handle my use case. I keep trying to nudge people at work about better domain support in HEY Personal but there are no plans to do that (😢), so Fastmail it is.

Our family uses iCloud for shared calendars. HEY doesn’t have a calendar so I use Fastmail for coordinating personal business-related appointments.

Messaging is split between WhatsApp and iMessage, and my phone calls are increasing going through WhatsApp. I use a Signal account when I have to with my nerd friends. I prefer WhatsApp, the UX is excellent. I’d just like it to support high-res images. It crushes the soul out of them right now.

For social media, I’m on Twitter, LinkedIn and Instagram. I quite like them all for different reasons and purposes. I’ve been trying Mastadon (@olly@ruby.social), but I can’t see me using it outside the techie circle I joined, unless Twitter completely implodes.

I’m currently using Twitter in a rather odd way. I’m not following anyone. Instead I’ve created a bunch of topic-related lists. The UX for doing this is truly awful, but once it’s set up it’s great! I can now read Twitter based on whether I want to doom-scroll current affairs, catch up with friends and colleagues, or read up on engineering topics. Twitter is rather baffled by this and my Home feed (not that I use it) is full of completely irrelevant “viral tweets” and cat videos. I’m sure Elon will do something that breaks this workflow, but it’s a refreshing way to manage Twitter.

I don’t typically read Twitter throughout the day. Instead I use Mailbrew to read it in a digest. This is particularly good because of partitioning all the accounts I follow into lists. I can now have separate sections in my daily (or weekly, for some lists) digest. I also subscribe to email lists/newsletters using my Mailbrew email address. I don’t use The Feed in HEY for this, I prefer getting them in Mailbrew. I also use Mailbrew for Read Later functionality. I don’t use Reading List in Safari or Instapaper.

I still use Reeder for monitoring RSS feeds, but I’m gradually moving this over to Mailbrew. Honestly, Mailbrew is so good! I’m a little concerned that the makers will sell it or shut it down, since they appear to be 100% focused on Typefully now. If they mothball it, I would have to build my own version.

For music (and the odd podcast) I use Spotify, which I’ve used since 2009. I still love it. I buy the albums I really dig via Bandcamp (or, if it’s not available on there, Qobuz etc) and use Apple Music for organising my library (I need to move this to Doppler). I buy dance music for DJing via Juno Download and Beatport. I host my mixes on Mixcloud.

I run my website at headey.net which is a static site built using BridgetownRB and hosted on Cloudflare Pages. My photography site at ollyheadey.com runs on Adobe Portfolio which I get as part of my Lightroom CC subscription. I use a Fujifilm X-S10 and X100V for taking pictures and I use Apple Photos for storing all my JPEGs and Lightroom CC for RAW files.


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That’s about it. Of course there are a bunch of smaller apps I tinker with (Rocket, Rectangle and Amphetamine spring to mind), but this article covers all the main ones - I could do without the small stuff.

I’d be interested to hear your thoughts!

[Header photo by Ashim D’Silva on Unsplash]

About Olly Headey

Journal of Olly Headey. Co-founder of FreeAgent. 37signals alumni. Photographer.
More at headey.net.