The Paradox of Choice

It’s email, it’s note-taking, it’s calendaring, word processing, bookmarking, mindmapping, pdf reading, file searching, citation managing, and the end-all-be-all-of-paradoxes: task management. (And more of course, I only scanned my applications folder down to the letter “G.”)

Do you have any peace of mind about your choices? (If so, which ones :eyes:? Maybe I’ll switch!) I know part of this is a love of tech that we all share (I think that’s really rewarding and fun), but part of it is maddening as it wastes time moving from one thing to the next and also creates gaps in the archive when we don’t take the time to migrate all things to the next thing (or the old thing that has now been updated, or not, or will be).

What do you do to reckon with the paradox of choice we have in software options?

  • 1Password - password manager
  • Alfred - whatever category Alfred is
  • Little Snitch - firewall ish
  • Keyboard maestro
  • Bartender

That’s it :grin:

The rest is up in the air. That being said there’s a bunch that I’m tempted to move from but keep coming back to:

  • Things 3 - task management
  • Apple Mail - email
  • iA Writer - writing
  • VSCode - ide like
  • Safari - browser
  • Reeder - RSS
  • Raindrop - bookmarks

That’s a great question and definitely an ongoing subject for us nerds.

Choices I’m at peace with and am not interested in switching:

  • OmniFocus (you make it whatever you want, and the review feature is killer)
  • Scrivener (nothing compares, no, not even you, Ulysses)
  • Ableton Live (totally fits the way I think)
  • Apple Music (seemless integration between streaming and my own music)

What I’m using because I’ve deemed it best but will consider changing if you show me something better:

  • Obsidian (I really love it but… it’s so un-Mac like, and mobile apps cannot come soon enough)
  • Spark (best in class, but still not perfect – work on that task manager integration please, on all platforms. Newton? are you still here?)
  • Fantastical (best in class but definitely too expensive)
  • Brave (come on Safari, get WebExtensions, lighten your use on resources, allow Qwant as a default search engine)

What I do when it comes to choosing: I define my dealbreakers and what I want the software to really do. Then I adopt it for a while and see how it goes. If I naturally stay there, that means I’m convinced, because that means the environment is better than having my previous data handy. That’s usually how my gut works and I trust it.


This is an interesting topic. I haven’t thought about apps that I’m 100% sold on, and have no desire to switch. Here’s what I’ve got:

  • 1Password
  • Day One
  • Droplr
  • CleanShot X
  • Keyboard Maestro
  • MailMate
  • Bartender
  • Timing

To answer your question: What do you do to reckon with the paradox of choice we have in software options?

I give myself some time (a few hours) every month to tinker. I watch YouTube videos about the competition and see what they’ve been up to. But most importantly I try to remind myself that most software is fluid (will always be evolving), and the more important aspect is to be an effective husband, father, friend, etc… But I fail at this regularly still. I wasted multiple days over Christmas break re-working how I was storing my journal / notes in Obsidian. Am I happier with the structure now? Sure, but it’s a negligible difference, so it really didn’t warrant the time investment. :man_shrugging:t2:

I just keep plugging away and try to do a little better tomorrow than I did today. :blush:


Choice? Or… OOOOH, NEW SHINY! :joy:

Guilty as charged.

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I loved trying new apps - okay I still do. But the questions I have to answer before trying something new is:

  1. What are the benefits of the switch
  2. What problem am I trying to solve. Can I solve it with tools I already have ? ie:Learn the tool better.
  3. How much time/effort/brain power will it take me to do the switch
  4. Do I actually gain more by taking the time to do a switch/conversion and instead investing in actions that move me closer to my goal

So even if my choice of whatever task is not the “best”. It may be the “best” for the time already invested (vs relearning ) to get me closer to my goal. Sometimes having less choice , means getting more work done.


Just a quick thought that occurred to me as I read the OP: I’m less about apps and more about principles. Those constraints provide some productive limits on app-switching.

I’ll write a few examples below. It’s not a conclusive list, just an off-the-top-of-my-head set of ideas.

A first principle: I want files. My mental model of how my workflows work emphasizes finding the content or materials I’m working with and opening those in any number of apps, not opening the app and then finding the content I wanted to work on. For this reason, the iPad lifestyle has always been fraught for me—recent developments in Files and apps as file providers are nice, but they’re still not perfect.

This same constraint leads me to like deep linking. If it’s easy to build links to the content, then I might be able to tolerate a file-less workflow (e.g., Craft, Roam). But still, I prefer being able to identify a file somewhere.

A second principle: Markdown. The content I work with needs to be able to be written in Markdown. I’ll export to docx or whatever as needed, but the more markdown, the better.

A third principle: I need a little bit of the right kinds of friction. If it’s too easy to add content, but not easy enough to manage it, whatever I’m putting into a “workspace” (i.e., an app + the content it works with) becomes noisy as heck and, inevitably, unusable. A great example of this is Concepts (iPad). It’s an incredible artwork/sketching app, but it doesn’t sync (!?) and interacting with previous sketches happens through a horrid UI. I used to open it all the time, but as a result of the buildup of cruft, I’ve moved away from it.

OmniFocus/Things/etc. are another example of too little friction. I quickly fill them up with wishes, not actions. Kourosh Dini wrote about this problem recently. Whenever I use a hyper-powerful task manager, it feels great for a week or two and then I end up feeling like I’m moving deck chairs around a titanic. I’ve since switched to managing my projects and actions in markdown (I know, right) and I’m much better at maintaining what I’ve got to do with integrity.

So, choosing apps may be the wrong way forward. Choosing principles or approaches and letting those define what tools you can use might be more functional.

Another giant throwaway: remember that we shape our tools and, thereafter, our tools shape us. Make choices (about tools, and everything else!) that reflect who you want to be.


Thank you, @ryanjamurphy, for this perspective. This is exactly why such decisions become fraught for me. It’s hard to project the effects of our choices into the future with shiny new features. And those choices matter in how I’m living my life and also who I am/become.

I also appreciate your principles framework and will consider what mine are. Now, :thinking:, what tool to document those thoughts in? :grimacing:


These days I am choosing to offload. Apps that I really like, admire the craftsmanship, but have increasingly used less and less:

  • DayOne
  • Bear
  • Evernote
  • Dynalist

all of which are standing forlornly at the back door, bags packed, and waiting for their subscriptions to expire and hit the road.

Also, alas, Tinderbox is standing next to them. I don’t know how many hundreds of hours I’ve used it every year, but it is increasingly unreliable. Haven’t decided to say goodbye, but probably will.

On the good side, then I can focus on the choices I really like:

  • Curio (my long-time favorite)
  • TheBrain (v12 shines compared to the mediocre updates the prior few years – it’s worth waiting things out sometimes)
  • MarginNote (no better for reading note taking)
  • Agenda (I’ve found new ways to use it, causing me to take it out of the losers heap and spend more time with it)

These are apps that are fun to use – I choose to use a lot of utility apps but they aren’t stars.

In the past few years the only solidly interesting and useful new app is Obsidian. But it’s not yet permanent in my portfolio. Time will tell.


I’m quick at moving data and find some value in the process. This helps me feel at peace with what I’m currently using because I don’t feel trapped. I suppose it’s the opposite of the adage that good brakes let you go fast–good acceleration lets me stay still longer. :wink:

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However, I sometimes think that the choice is good.

For example, I use a number of different programs to write my Markdown files. Typora is the go to, but occasionally I find it easiest to edit the file in VS Code, Textastic or nValt.

None of the the programs tick all my criteria, so I’m able to use the same file in a number of different programs, which all excel in certain aspects over the others.

As I come close to wrapping up my 9th year of retirement, I’m finding a lot of apps I can do without. Mainly because I get to choose what I work on instead of someone else influencing it (except for my wife). Just deleted MS Office off my Air today because the subscription expires in 2 months and I’ve migrated everything to Pages and Numbers. The few Excel spreadsheets I get from others always open correctly in Numbers because I’m not dealing with power users.

For the most part I’m using the built in Apple apps. They usually work better cross my MBA, iPad, and iPhone. A lot of times digging into an existing app can solve an issue without having to add a new one. I need to do X. Instead of looking for an app that can do X, why not determine if my existing apps can do X? It will often take less time.


How are you using Agenda that is so different ? How are date based notes useful ?

I have dropped a lot of apps over the past year or so, gone is any electron app, the final one hanging on was VSCode but Nova from Panic has replaced that for me know.

Docs are all in Markdown. Most storage is in Devonthink, writing I do initially in Drafts, mail is handled by Mailmate which I keep coming back to.

My main daily apps now are Omnifocus which handles all my personal and business tasks/reminders. Drafts for notes (sent to DT later) journaling and writing. Coding is Nova, and Mail is Fastmail with Mailmate as a client.

I do virtually no meetings or appointments so Apple Calendar works fine, Graphics are mainly done on Pixelmator Pro, (much faster than Affinity for edits and resizes). I guess we all maintain utility and complimentary apps, KBMaestro, 1Password etc etc, as these ease the frictions.

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I’ll post more about this separately.

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I try to evaluate how I think, decide what tasks I expect the app or app class to do and then look for the most full-featured app in that class that syncs with my way of thinking. Generally that means that I will end up with more expensive apps, and that they are complex, have long learning curves and can be frustrating to the novice or new user. But for me, if I can get past the initial “this thing is too much why did I try this” stage and get to the basic competancy in the complex app I can usually run with it for years without changing.

For me choices I’m happy with an not even looking at changing on my Mac include:

  • Omnifocus
  • DEVONThink
  • LibreOffice
  • Scrivener
  • GoodNotes (newly added to this list)
  • Zotero (newly added to this list)
  • LightRoom Classic
  • Photoshop
  • Carbon Copy Cloner
  • Hazel

Things I’d like to change but haven’t found good alternatives that meet my requirements include

  • Apple Mail
  • Apple Calendar
  • Apple Contacts
  • Banktivity
  • PDF Expert
  • 1Password

Things I am testing that so far seem to be moving into the not willing to change category but aren’t totally there yet

  • Obsidian
  • Aeon Timeline
  • Highlights
  • Keyboard Maestro (I will move this to the vital category once I get more familiar with using it)

Things I’m testing and look like I may delete

  • Mindnode

Things I use sparingly and would be willing to move to any better alternatives

  • Scapple
  • NameChanger
  • TimeTable 3
  • Podcasts App
  • BookPedia et al

This is so true and part of why I start first with how I think and find apps that work that way.

I’m less concerned with things like Electron vs native as long as the app does what I want to do and gives me value and I can work with it. Because I also comparmentalize what tasks I do on what devices I am less concerned about exact seamless parity between Mac, iPad and iOS versions than many people as long as the chosen app does work for what I do on each of those devices if the task is one I do on multiple devices. Sometimes that even breaks down into using the same app but different pieces of it on different devices.

For example: Omnifocus additions, review and editing tasks and projects happens only on my mac so I dont’ really care whether it works as easily or as well on the iPad or iPhone. OTOH clicking off done tasks and seeing what I have to do in a specific context is critical on those mobiile devices so that had better work easily.

I have both data silos to keep certain classes of data isolated from others but I also implement functional silos because that frees up my mind and energy. I know I’m not going to try to answer and respond to email on my portable devices so that’s a whole class of stuff I don’t care about there. I know I will only ever do a review of Omnifocus when I’m at my Mac so I don’t care how it works on the iPad (and in fact I hate OFs review on iPad, it’s clunky to me) and so on. I have sets of things I do on each device and only a few cross devices.


Sorry if this breaks your resolve, but I used to rely on those apps too. They were “the pinnacle” of their breed. Except when I got a bit fed up with the subscription I looked elsewhere and discovered they’re not the best of breed at all.

I’ve found it really hard to replace Lightroom Classic as a Digital Asset Manager (DAM) but as a photo processor I now get far superior results with DxO PhotoLab 4. Night and day better. So good, in fact, I’ve gone back and reprocessed well over 1,000 of my old photos (some as far back as 2009) and republished them in a much higher quality.

As for Photoshop, I could still use it and probably be happy with it, subscription aside, but the Affinity Suite of Photo, Designer, and Publisher are a killer combo. Less so, I guess, if you don’t use Illustrator or InDesign, but Photo on its own replaced Photoshop for me years ago and I’ve not looked back. I use it for “graphics” rather than photos, and it does a fantastic job and the performance is insane. Ludicrous, even, on M1 Macs.

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That’s my use case for Lightroom and Photoshop comes along for the ride.

I use LR as a DAM for my own collection (consisting of, when finally all in, over 50K individual images) and for the Historical Society Collection (currently at a couple hundred but we have about 12-20
K total to deal wth eventually)

To be honest the LR develop tools are more than sufficient for my needs.

I just went through a couple of months of changing a couple of core apps to see if alternatives were better. I tried a couple of alternatives to DEVONThink, based on documents stored in the Finder. I also tried GoodTasks in lieu of Things, Brave and Firefox in lieu of Safari, and Feedbin and NewsExplorer in lieu of Inoreader.

I ended up returning to DEVONThink, Things, Safari, and Inoreader.

Was this a useful exercise, or mere procrastination? Beats me.

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What are you doing with retirement?

I turn 60 in July; retirement is something I think about a lot lately. I can’t imagine it.