We might have reached Peak Apps

It’s a great time to be a productivity nut. (Note that this post is going to be incredibly first-world-problem-y in nature.)

Since moving to Berlin I’ve had an opportunity to critically review how I work. My job is for the same company and essentially doing the same thing, but I was able to shed some of the burden of direct reports, longstanding internal processes and borderline-political work relationships, and kind of start fresh in a way. My morning routine has gotten more about me – taking time, eating a real breakfast, learning a bit of German via Duolingo, reading news instead of email.

When my mind is feeling nourished, I plan my day with Things 3, moving stuff for this evening to This Evening, comparing my pockets of available time with the number of tasks or projects I need to focus on, and deferring the least important things. I might draft up a few writing ideas or notes for projects in Drafts, some of which get linked to in Things and others that sit in my inbox for when I have a creative thought later.

My bigger idea boards for things that need planning or some kind of structure sit in Trello.

This all works for me quite well… but on some days it feels wrong. Why manage some projects in Things and others in Trello? They’re both really good, but why do I need Things to supposed Get Things Done when Trello can organize my projects with structure and let others collaborate with me?

Collaboration is important, right? But isn’t focus? Trello can do focus really well, I think. But then again, Todoist is also great for focus and collaboration – plus, it can automatically pull in tasks from anywhere via its API. But, Things can kind of do that through its own URL scheme and Mail feature.

GoodTask can do most of the above too – plus it integrates with Reminders, which is great because I can talk to it via Siri and not have to remember to say “using Things” or something very unnatural. Then again, why not just use stock Reminders since I can remind myself about most of the things I need to work on and have it smartly link back to those things? Moleskine Actions also looks really good too, I think. I haven’t even mentioned OmniFocus, because that’s…too much for me right now.

Literally all of these options are totally fine and look, perform and function amazingly. I haven’t even touched the writing, presentation, mind mapping, or spreadsheet apps. My brain hurts.

It’s a weird time to be a productivity nut. Most of the popular apps in most categories are all really, really good. How do you know which one is best? What is best, anyway?

Best for most people? Best for productivity nuts? Best for a married couple? Best for tech company employees? Best for strong female entrepreneurs? Best for stay-at-home dads? Best for digital nomads? Best for you? You’ll probably find a list like this and see roughly the same 10 to 20 apps in a given category, all of which are really, really good.

Navigating this is really hard. Not because the lists of “best apps” are too long or they’re too expensive or hard to find, but they’re just all so good. It takes a long, long time of trying each one out, being wowed by the unique features or design conventions or automation potential or scalability of each one, and having to decide which secret sauce of those is best for you. Apple is sometimes helpful with this, but other times not. I love the new App Store, but when I see a feature focused helping me “Get to Inbox Zero”, I can’t help but laugh at the 15 email clients they recommend for this – as if they’re sneering, “Literally any of these will work, we don’t care, just pick one.” It’s almost lazy.

Not to mention how those apps in a single category connect with the 10-to-20 best apps in a _different_category. I’ve finally decided on sticking to Things, but do I use that in tandem with Drafts? Bear? Ulysses? Apple Notes? Byword? 1Writer? Each of them? Some combination of these? I could use a cocktail of these different apps that basically do the exact same thing, but how much time must I give myself to figure out that perfect Manhattan of writing a few ranty blog posts on an iPad?

I also have to imagine it’s especially hard now to develop an app in the productivity or writing category and not be in this list. Either:

  1. You could copy some design conventions or differentiating functionality of one of those 10–to–20 apps, do some marketing pushes, and eventually be admitted into the wonderful apps club

  2. You could try and determine some feature or use cases that none of these thousands of people figured out already, and take a big gamble

  3. You should just give up and die

To be clear: I don’t think any of this is bad. I find it an interesting time in the world of mobile-first productivity and content creation where the consumer is pretty much always going to be delighted. Developers of that top-tier bucket of apps clearly know what conventions and functionality their consumers want and are willing to listen hard to understand how to best deliver that. The question for the consumer has gone from “what is the best app out there?” to “what is the app or apps that best suit my particular needs at the moment, but also jive perfectly with how I think or what I want to look at?” The second is a much more time-consuming question to ask, I have to imagine, for most people.

32 places to put stuff

I have a lot of places in which I put things I care about.

I use Reminders to store…well, reminders of things I need to do. Basic lists.

I have a wish list of stuff I want to buy on Amazon, but then I have another list of other non-Amazon stuff to buy in Reminders.

I also have a few lists and notes for things in Apple Notes.

I keep my passwords securely in 1Password.

I use Trello to manage projects, but not all projects because not everyone uses that.

For some things, I need to make a Google Doc or Sheet. (Somehow, I’ve literally never had a need for a Google Slides presentation.)

Sometimes those projects have other materials. If I’m collaborating, they get shoved into Google Drive or (occasionally) Dropbox.

If it’s a personal project, it’s most likely iCloud Drive.

If it’s something in Adobe’s ecosystem, it might end up in Adobe Creative Cloud – I barely ever use it, but sometimes things occasionally end up in there.

I use Scanbot to scan papers, receipts and stuff for storage in one of these places

If it’s a work thing, it goes to Sharepoint which also includes a hook into OneDrive.

Sometimes it’s a manual or guide book for something, in which case it goes to iBooks, which is basically iCloud but also sort of not. Speaking of iCloud services and reading, Safari Reading List also houses some reading materials that I care about.

Photos can of course be stored in many places – it doesn’t really matter where they go as long as they’re everywhere all the time. In case they aren’t, well, they start in iCloud Photo Library, then go to Google Photos and Amazon Prime Photos.

All this stuff backs up to one of two external hard drives, and an Amazon S3 bucket.

Sometimes I write. I like Markdown for my own personal writing, so I write lyrics, creative ideas and blog posts like this one in Ulysses.

I can’t use that for my day job, though, so for that I use OneNote to write & share notes & documentation with my team.

We use a proprietary solution for managing technical projects.

Roadmap documents? Excel and Word. Not Trello, at least yet, because I need to get people to adopt it and we’re a pretty tight Microsoft shop. Speaking of which, Powerpoint.

We still use Slack to communicate, and I use it for some other things. Sometimes I save notes and to-dos as starred Slack messages.

Of course, there’s always stuff in one of 3 Gmail inboxes, my work email via Microsoft Exchange.


This is a list of apps in which I can put things I care about. They all have incredibly discrete functions in which they’re invaluable to me, but they all each have storage capabilities too. There’s also all the physical papers and forms and stuff filed away in a bookcase.

Thank goodness cross-platform search technologies these days aren’t awful, because if I had to remember in which place I stored something, I would be lost pretty much constantly. As much as the app economy and tech startups fascinate me, it’s almost too easy to lose track of everything. If productivity tools like Workflow and IFTTT make it so much easier to keep things in sync, and there’s backup solutions galore, why does the digital side of my world still feel so fragmented?

As much as Apple’s plan to store users’ entire Desktops and Documents folders within iCloud for syncing purposes is slightly nerve-wracking, I appreciate the effort to help consumers keep their shit in one place. I realize this anxiety is partly my own neuroses and my being raised on a file system paradigm, but I also have to imagine that the fragmentation of the cloud storage (and general digital storage) markets are part of why tech is so overwhelming for some.

The problem of task managers

Wunderlist, Trello, Todoist, OmniFocus. 2do. Things. I have to imagine that most smartphone users haven’t even heard of these apps. That's probably why there's such an apparent subculture around each one. The average person will never break into the most beloved apps, and those who do will defend it to no end.

So why don’t so many people, who presumably have things they need to do in their lives, use one of these tools? For all the people that do try a project management tool, why do so many underutilize them?

Everyone has a smartphone, and most of them probably use stock functionality (read: Reminders & Calendar) to keep track of their daily lives on that smartphone. However, Reminders rarely has accountability – what if you forget to set a reminder time? What if you miss the location-specific notification by the time you’ve left? What if some to-dos are dependent on others and you can’t check them off the list until some other thing you neglected gets done?

Are the to-dos I’m getting reminded about even a good use of my time right now?

What about the big important complicated things I want to do?

How do I even break those things down into the little to-dos to put in my list?

What does that mean to me in the big picture?

The average person doesn’t want to (and almost certainly can’t) think through all that stuff, even though they potentially have implications on their daily lives.

This conundrum, in the workplace, is basically why project and product managers exist. Product managers help to figure out the right things to focus on and why; project managers make sure they happen so you, Mr. Stakeholder Guy don’t have to worry about all the little details.

Personal assistant apps exist, even virtual ones, to remind you of upcoming meetings and tasks – so why haven’t we developed a “personal product manager” that takes your big goals in life and helps you break them down and focus on the most achievable pieces of said goal?

I think about the big things that I want to eventually do in my life – get married, build a company, buy a house, be a notable musician, other things – there’s a ton of knowledge of what to do to make those things happen on the Internet. But parsing all that information is a nightmare – you’re basically relegated to Google searching or starting with blogs/resources you trust and vetting the content endlessly until you end up with a series of tasks, which may or may not be in order, prioritized or even possible. Then, you have friends and/or family as a resource, which may contradict your online findings (or even each other). I don’t even want to think about the difference between my dad’s opinion on starting a business compared to my previous employer.

Productivity apps can’t do this thinking; it’s not what they’re designed to do. 2do, one of my favorites, requires a whole lot of task creation and organization in order to be truly useful. and People have said that about Evernote, too. Trello is great for visualizing projects in a board format, but it doesn't tell you what should populate that board and what of that stuff needs to get done in order to make BIG AMAZING GOAL X happen. (That's probably why they've started collecting and sharing sample boards for various use cases.) The thought process around focusing the idea into discrete pieces hasn't been productized for personal lives.

I wonder if this is why productivity apps aren't ubiquitous – because they exist to humor the details of lives instead of boiling them down to what’s important.