Moving from Android to iOS

I recently caved in and got an iPhone after years of being a non-conformist hater 😬. The biggest takeaway (other than popular ≠ inherently bad) was that many of the features I bought into Android for (like widgets, app-to-app content sharing) have been available in iOS for years. I was just anchored on an earlier model that’s now pretty dated.


💬 Messages 

The killer app on iOS. It just feels frictionless to communicate with people and I’ve started chatting more regularly with friends because of it. I have a few friends not on there and the green bubbles make it very noticeable when I’m communicating with them. I’m a big fan of Messenger and thought that with its user base and excellent UX (sans ads) it could fill the gap. Anecdotally, only about 1/3 of Messenger users have the app installed or check it as frequently as text which makes it less useful. 

Additionally, seamless message syncing in OS X - even for SMS - works so much better than all the hacky workflows you can set up with third-party Android apps. 

🎛 Control

I was surprised by the granularity of control baked into the OS. You cannot install a launcher, add your own gestures, etc. like you can on Android but you have controls for things that actually count, particularly:

  • Fine-grained app permissions
  • Fine-grained notifications permissions and styles
  • Customizable extensions (including ad blockers)

🔕 Focus

Though there are still challenges with being tethered to a smartphone, iOS has some great features around avoiding distractions. Again, with fine-grained notifications permissions you can choose where notifications are shown - if at all - by app. Not having notifications in the icon bar makes it possible to actually not check for notifications (or run a background process in your mind to figure out what could be behind that icon) while doing something else. For the first time I can let those red badges populate and not need to act on them as immediately.

I make use of Do Not Disturb constantly, both when powering off and when focusing on deep work. I pair this with automated Night Mode as before bed.

🔋 Battery 

Sadly, I am still blown away by my ability to stay out all day and into the night, using my phone pretty heavily and not thinking once about my charge. An added benefit of the iPhone network is that whoever I’m with is bound to have a charger on them if I don’t.


🔐 Passwords and access

I have a lot of trouble with the front-facing fingerprint scanner on a regular basis, but especially when my hands are sweaty or if I’m cooking. I’m still not sure what the flow is when I’m pressing it and what stage of I’m at, but it’s usually in the locked out one. Never had that issue on my Nexus 5X or 6P.

It’s challenging to enter forms and login to apps. Unlike on Android, password manager apps can’t paste your credentials in for you. There are a growing number of apps that support password managers, but this needs to be built into the app and most don’t have it. I use Brave as a browser, which supports password management extensions, but any login flow that uses a webview (logging in via Google, Facebook, Twitter) defaults to Safari and doesn’t access cookies from main Safari app.

🔍 Searching

Searching with Google is intentionally difficult on the iPhone. It’s a small thing, but something so core to how we use the internet. There is no way to search Google without an extra tap either on the spotlight screen (Search the web) or via the Google App. A foil to the ease of Messages, the tiniest bit of friction here adds up when you use something over and over again.


It’s clunky to edit and delete lists of items. Using cross-platform apps that support this, like Inbox and Todoist, and the general Android OS, I’m accustomed to swiping everything left or right to perform actions or just get rid of them. It takes me a long time to edit things like playlists, alarm clocks and bulk edit seems slow to me.

🛎 Notifications 

As I mentioned, notifications are excellent in a number of ways but are weak on clearing them or acting on them. It takes multiple taps to remove a notification.

👇Force Touch

This feature wowed me with simulated depth and clicking and there are lots of great uses for it, like quick actions on homescreen icons. But almost all force touch actions lack a cue that lets you know they’re available. I am the type of person that force clicks on everything to see what will happen and sometimes get these half-states that zoom in on image or notification and don’t seem to do much else. 


While both sides are shipping excellent new features and presentation concepts, they are mostly equivalent in my mind. The thing that really makes a device (or any product) stand out is the holistic user experience. 

If you strip away all of the above features, what actually makes the iPhone superior in experience are:

  • Better physical design to nearly all Android handsets. It is the first one that fits in my skinny jeans pocket naturally and feels good in my hands.
  • Network effects of having my friends and family on it. (Though this would be different in other parts of the world where Android reigns supreme).

Hot takes on the same ancient applications

It never ceases to amaze me how many times we can revisit and recreate the same basic concepts for organizing our digital lives and work. Each of the core tools we still use today still looks pretty similar - in terms of mental models - to those produced by Lotus et al. way back when. Nonetheless, new technologies and UX concepts have kept them very much alive.

🔥 UX

🔥 UX

Here are some interesting new versions of age-old applications I’m using.

Email: Astro

Astro puts a chatbot spin on the email client, with a smart assistant to send you notifications and suggestions. 

The team is also quick to innovate and just announced an integrations with Slack and Alexa. I’m looking forward to what they come up with next, but for now am very satisfied with the basics.

Defining feature(s):

Tried and True Email Features, Cross-platform

Astro doesn’t do anything that hasn’t been done before - at least for the features I find most valuable. It just packages them nice and tidily. Consolidated mailbox for multiple accounts, focused vs. other inboxes, VIP contacts, customizable filtering and notifications have all been done before. Outlook has had them for ages, but has had poor support for google accounts and cross-platform features. It took them years just to bring focused inbox to desktop!

New School Email Wizardry

Astro brings the new school Google Inbox and Mailbox features like snoozing and reminders, which I could not live without. As an added bonus they take the cake with nice-to-haves out of the sales automation world with features like open tracking (and notifications), reply-by dates and send later. I’ve used Mixmax and other chrome extensions for this type of thing in the past, but Astro is the first client I know of that brings them natively to mobile.

Screen Shot 2017-06-15 at 5.38.03 PM.png

Note-taking: Bear

Bear has gotten a ton of hype for its design and was just celebrated with an Apple Design Award. It’s beautiful and distraction free, with the markdown input features you expect and a few nice surprises - like automatically filling in a hyperlink with whatever the browser is open to.

Defining feature(s):


I obsessively organize and reorganize my notes which becomes unruly after a while. Just like gmail did to the email folder, Evernote (and perhaps others) brought the tag to life in note-taking apps. Why choose where a note lives if it can live in n number of tags? 

Bear takes this concept up a notch by giving users the ability to add/edit tags directly within the note using hashtags, including nested tags. This combined with the markdown and simplified formatting shortcuts means you never have to touch the mouse. Evernote should have come up with this years ago.

Browser - Brave

Brave is an open source browser that has built-in tracker and ad-protection and makes browsing a pleasure. It recently had a high profile ICO and is very promising.

It’s currently in beta and so understandably I’ve found the desktop version a little wonky, but I’ve already made the iOS version my default browser and am focusing on that version.

Defining feature(s):

Built-in ad and tracker blocking

Though Safari allows users to add their adblocker, it doesn’t port to web-views or to Chrome, obviously. Having this baked right into my mobile browser is a lifesaver.

Password manager extensions

There are very few extensions available out of the box, but all the major password managers are there out of the gates. A much slicker way to auto-fill credentials than on other mobile browsers.


One of my biggest complaints with iOS is how many touches it takes to make a Google (or other) search query. Brave is the fastest way I’ve found to search and I love how clicking on an engine icon works as “Enter”.

Task Management: Todoist

Todoist is elegant and simple. Clean UX and a variety of views for power users without getting into Omnifocus territory. It’s as simple or complicated as your workflow and fits all shapes and sizes.

There is a lot of hype around Things 3 right now but I’m not sold on the price point (and multiple purchases for cross-device) before getting to test it out. I know what Ben Thompson will have to say about this pricing model.

Defining feature(s):

Quick Inputs

Todoist does an excellent job with quick inputs and smart capturing for due dates, projects and recurring intervals. This is a lifesaver when writing down a can’t miss task in the middle of a meeting or on the go, though I am disappointed with a iOS version compared to Android and macOS.

Documents - Google, for now…

I’ve been using Google Docs for over a decade (and later Sheets, Slides), like many, due to the ease of collaboration. But now I find myself using Apps simply out of convenience. True, Sheets will never be as powerful as Excel, but does it matter? For heavy accounting and modeling use cases it does, but for the rest of us I’m not so sure.  It also hooks up with other applications and BigQuery to dump data directly in.

Sidenote: My only complaint with Google Sheets is having to create a new document when I just want to do some quick equations. To get around this I keep a sheet bookmarked “Scratchpad” that I noodle around with an write over constantly.

Defining feature(s):

Sharing & Collaboration

Real-time collaboration is still magic all these years later but…

There’s a lot of interesting things happening here collaboration forward tools like Dropbox Paper, Quip and Notion . I think that this is where the most far-out and game changing developments are happening as teams redefine what exactly a document is and will be.

It’s refreshing to see some new life breathed into these old concepts. As long as developers keep making email clients, to-do lists and the like, I’ll keep obsessively trying them out.

Dinner - Olmsted, Brooklyn

Experimenting with iPhone 7 camera. I don't usually indulge, but food photos are fun.



Morgans Meats, Crab Rangoon

Morgans Meats, Crab Rangoon

Carrot Crepe

Carrot Crepe



Rutabaga Tagliatelle

Rutabaga Tagliatelle

Softshell crab

Softshell crab

Pork collar

Pork collar

Obligatory donuts

Obligatory donuts