In an ideal world, I wouldn’t have to trust my data to a third party. I could simply plug a box into my home Internet connection, and trust that my digital life would live there while being accessible on any other device I own. It would hold everything from email to personal files, from photos to music, from my health data to my identification credentials. It would be 100% reliable, secure, encrypted, and accessible only to me—and maybe my partner. And, as long as I’m living in a fantasy world, it would cost a nickel, use no power, and come with a free pony.

So, I’m stuck offloading my personal data to an assortment of companies with varying degrees of reliability and trustworthiness. The chart below helps break down where several of the services I use—or used to use—fall.

The services in the bottom left corner are ones I’ve stopped using, save for LinkedIn. Jawbone and FitBit are flaky services that silo my data. LinkedIn is just frustrating and annoying. There is only one service in the bottom left corner, which will surprise no one, because no matter how much I can trust something, I will not use it if it is unreliable. I conflate reliability and utility, mostly because three-dimensional charts are terrible, and also because unreliable services are generally useless anyway.

Reliability is a huge factor—will I open an app to find that all my pictures, files, music, what-have-you is exactly where I left it? Will the changes I made on one device propagate to all the others without errors or data loss? This is a hard problem to solve, and nobody’s gotten it completely for everything. The more complex the data set, the bigger the problem is to solve. Google seems to have a lock on this, along with Dropbox. iCloud is getting there, but has its share of weird issues that are slowly being ironed out. We’re not hurting for Internet services that fail to deliver on their promises in terms of having our data everywhere. There’s another factor we need to consider.

That factor is Trustworthiness. Trust is a question of data security–not just against malicious actors, but also how the company will be using that data. Let’s go back to Google. Though I’ve had nothing but bad luck with Google Now, I like the idea in theory. I had high hopes for the new “Proactive” features in iOS 9, but they’ve been largely a non-entity for me. If Google was just going to be using the data I feed it to better my life, I’d have put them on the other side of the chart.

Instead, Google sells my data—supposedly anonymized, chopped up, and in bulk—to advertisers. That’s a violation of trust. In all other respects, Google is a solid steward of my data. They’ve had data leaks and security breaches, but no more so than most other companies in this space. I’ve also never run into synchronization issues or data loss with Google.

iCloud loses a few points on reliability, but makes up for it immensely in trust. Apple’s commitment to privacy has me more willing to use their services for my personal data than any other, even if I’ve run into a handful of issues with synchronization. It’s a choice based on principles, and I’ll take a handful of frustrations with the knowledge that my data is safe, over knowing my data belongs to people who I didn’t explicitly authorize access to.

One day, I hope I can have all the services I choose to use in the top right corner of this chart. I want to trust that my data stays safe, stays mine, and is not sold to the highest bidder. It’s not going to be an easy battle, since it’s more lucrative for companies to sell data and keep the services free. Data is the currency of the Internet. We’ll probably never be free from trading data for services, but I can hope that one day we’ll have more options on how much of our data to spend. Until then, I’ll keep holding out hope for the free pony.

The Apple/FBI comedy of errors continues, and it’s likely to end up being argued in court. This means there is a possibility—following appeals and other legal maneuvering—that Apple will be compelled to write a tool to unlock iPhone encryption. This wouldn’t be just for one iPhone 5C, but for every iPhone.

Let’s get hypothetical for a moment. Suddenly, there is a single piece of software—a master key for nearly a billion iPhones. Can you imagine what people would pay for access to this? There would be governments and security firms swarming every iOS developer at Apple, and every digital forensics person in the FBI, with promises of untold riches—that is, if someone doesn’t leak it for free, first. There’s a non-zero chance that someone within Apple, or within the FBI, would make a copy of this software and put it on a Warez IRC channel or a torrent of it on The Pirate Bay. I wouldn’t be surprised if it happened inside of a day. And you can bet that whatever way it gets out, it will never be contained.

If you don’t believe this, know that it’s happened before. Microsoft COFEE, a forensics tool for Windows PCs, was leaked in 2009. A leaked tool called EPPB which can download a user’s complete iCloud backup was implicated in the iCloud nude photos leak. What makes anyone think an iOS master key would be any different? Apple may have the right to keep, and even destroy the software, but that isn’t a defense of it being leaked during the investigation. If someone can leak 3D models of the TSA master keys, nothing is safe.

And if it leaks, there will be teams of hackers working to reverse engineer the code. Most of them will working out of sheer curiosity, not because they want to crack into people’s iPhones. That’s just what hackers do. Some, however, will do it out of malice—or just a paycheck. Look at the iOS Jailbreak community. Every time Apple locks down iOS, Jailbreakers manage to break it open again, with all the security risks that entails. Anything Apple is forced to do by the FBI will probably be a lot easier to run, and easier to spread. What happens then? Now, there’s a cat and mouse game as Apple tries to keep iOS locked down from the US government, foreign governments, and black hat hackers with their own copy of the master key.

This is the worst case scenario in the Apple vs FBI fracas: an official backdoor into iOS, precedent for the FBI, the NSA, and other governments to demand Apple—and any other technology company—decrypt their phones. On top of that, the same backdoor will have a million lock-pickers trying to turn it into a master key for close to a billion iPhones.

If Apple loses this fight, be afraid. Be very afraid.

I use iTunes a lot. I’m also one of those rare people who have very few issues with iTunes. It imports my music. It plays my music. It synchronizes my music to my iPhone. It works. Barely, sometimes, but it works. I’d love to see an update and a rethink of the UI, but whatever happens with upcoming versions of iTunes there is one thing I don’t want to see. I don’t want my music to live in the cloud.

That’s not to say I wouldn’t mind having my music be in the cloud. As long as the cloud is an accurate mirror of my locally stored music library, access to it from any device would be awesome. There’s no way to keep a local copy of all my music, anyway. Apple doesn’t make a portable device large enough, anymore. Even if they still made the iPod classic, it couldn’t hold all my music. I sync a subset of my massive library onto my phone. This means that if I want to listen to an album at work that isn’t on my phone, I’m out of luck.

Yes, I am an edge case.

So, cloud-based music locker services are pretty much made for me, right?

No.

There’s a lot of trust that a cloud-based music locker needs that I am not willing to give up yet. I need to trust that the music locker will respect my anal-retentive metadata and organization. I need to trust that the music locker will not replace my rips from vinyl or remastered CDs will be replaced by different versions. I need to trust that the music locker will not replace my live recordings—of various degrees of legality—with studio recordings. I need to trust my music will remain mine, and not used as a way to get more data to display more relevant ads. I need to trust that the software I use to access and play my music works the way I think. I need to trust that the right music will play, without issue, when I tap the play button.

Right now, none of the options out there meet that level of trust. I’m wary of using Google and Amazon’s lockers, because I don’t trust those companies with my personal data. This leaves iTunes Match and/or iCloud Music Library. Until recently, my library was too large to use either. I actually whittled my library down to make it fit, and my readers will already know how that worked out.

Even if the issues around iTunes Match and iCloud Music Library are sorted out—and I have no evidence this is the case—Apple has lost my trust in this area. It might not be a permanent loss of trust, but they’re so far behind that it will take a lot of work to do it. If iTunes, or whatever replaces it, puts the cloud first, it needs to be flawless for me, and other obsessive music nerds (like, say, Jim Dalrymple).

What does I mean by flawless?

It means that my music remains my music—that nothing is modified by Apple between my media drive, the cloud, and my iOS devices. End of story. The only way I can have this, with services I can trust, is to synchronize files to my phone. This might be going away. Rene Ritchie wrote on the possibility of iTunes moving to a cloud-first model, and the idea scares the hell out of me.

What worries me most about a cloud-first iTunes is that it means I will lose the ability to simply synchronize music files to my iPhone. Right now, iTunes has this bizarre (to me) hybrid approach where music can live in either a set of local files or in the cloud. My way of dealing with the ambiguity is to disregard every cloud element of iTunes and use it purely with local files. This is the way I’ve managed my music for over a decade. A cloud-first iTunes will, at best, leave local media as a second-class citizen.

I don’t suspect malice on Apple’s part for this, though I’m sure they would love more Apple Music subscribers. I suspect that the Music and iTunes teams at Apple feel that the cloud for media is the future: streaming first, a music locker second. They genuinely think is the best solution for everyone, and maybe it is for your average music listener. I am not the average music listener. On the day I wrote this, I dropped $75 on a two LP reissue of DEVO’s E-Z Listening Muzak collection. This is not normal—for multiple reasons. If Apple has to leave anyone behind for their ideal music listening future, it’s going to be the loonies like me.

So, if Apple leaves me behind, what do I do? There are iTunes replacement apps, but they don’t synchronize my phone. Plus, while all my digital music is DRM-free—both what I purchased in iTunes and acquired through, er, other means—I have videos that are copy protected. If I ditch iTunes, I lose access to them, unless I break the DRM. How soon before I buy a Sansa Clip, a high capacity SD card, and manually manage my music again, down to the file level, like it’s 1998 all over again?

I try not to be afraid of technological change. I try not to be cynical. As it stands right now, I see no way out. Music is a huge part of my life. I even own music on cassette tape. I don’t even have a tape player. Music moving to the cloud threatens to upend so much of how I experience something that brings me no end of joy. I can’t be the only one.

The implications of the government’s demands are chilling. If the government can use the All Writs Act to make it easier to unlock your iPhone, it would have the power to reach into anyone’s device to capture their data. The government could extend this breach of privacy and demand that Apple build surveillance software to intercept your messages, access your health records or financial data, track your location, or even access your phone’s microphone or camera without your knowledge.

— Tim Cook’s letter to Apple Customers

Read this. If you value you freedom, your security, and your privacy, read this.

A backdoor for the government can be used by malicious actors, both within the government and without. It can be used to spy on anyone, whether they are a suspect in a crime, a political agitator who has done nothing against the law, or even an ordinary, law-abiding citizen. A backdoor can be used to spy on ex-lovers or new flames, and existing ones already are.

That is the crux of the issue. There is no way to ensure that a backdoor will only be used by the “good guys.” It is impossible to do so. The only way to avoid this is not to have a backdoor in the first place—for anyone.

Introduction

I’m a sucker for the new hotness in task management apps. I can’t lie. I’ve bounced around between Things and OmniFocus, but dallied with Todoist, Wunderlist, and a whole host of various other apps to try to keep my life—or at least my to-do list—in sync. Right now, the new hotness is 2Do. It’s not a new app, but Federico Vitcci of MacStories gave it new exposure with his glowing, detailed review.

As I’ve spent way more money on task management software than I would like to admit, I resisted giving 2Do a try. However, the recent Email to 2Do add-on got my attention. It seemed a great way to bridge an annoying gap between the way I manage tasks for my day job, and the way I manage tasks for the rest of my life. So, I jumped in with both feet, switching from OmniFocus… and then becoming remarkably confused.

Try as I might, I couldn’t find any guides specifically for going from OmniFocus to 2Do. The two apps are similar in terms of features, but almost polar opposites in organization. OmniFocus is strict in its GTD [1] approach, while 2Do is more flexible. Which of these you prefer comes down to personal preference. There have been times when I found OmniFocus too restrictive, and times I’ve found 2Do not restrictive enough in my short time with it. Still, for anyone else in the same boat, I offer you my brief guide to moving from OmniFocus to 2Do.

Making the Jump

If you use OmniFocus and 2Do on the Mac, moving your data starts out easy. You can just copy and paste all your actions out of OmniFocus and paste them into 2Do. The hard part is organizing them. 2Do’s loose structure means you’ll have to build a GTD-style system out of its component parts. What I settled on is as follows:

Lists are Projects

In 2Do, the list reigns supreme for organizing your tasks. Whatever, generally, was a project in OmniFocus, became a list for me. That’s not to say that 2Do doesn’t have Projects as an option, but I typically use Projects to organize “Sub-Projects” under a list. And, truth be told, I rarely used Projects in OmniFocus as true GTD-style projects, more just ways to organize related tasks.

I also subdivide my lists/projects into groups, based on different areas of responsibility. There’s a group of Personal lists/projects, a group of Creative projects, and a group of Office projects for my day job. Plus, I have a Waiting group that also covers my Someday/Maybe list. It’s not perfect, but it reflects a similar organizational strategy I used with OmniFocus

Tags are Contexts

2Do has no dedicated “Contexts”, but it does have tags, which serve as a good surrogate. The main difference is that you can assign multiple tags to a task, (sub-)project, or checklist. I don’t do this, for the most part, save for my “Waiting” context. This, I use to lock off tasks and projects I can’t do yet, and that lack a hard landscape before I can do them.

This works great when combined with the ability to pause certain tags in the app, hiding them from your usual list views. There’s one caveat, though—paused tags are not available on the Mac yet. A recent tweet from the 2Do Twitter account suggests one shouldn’t hold their breath for it, either.

Smart Lists are Perspectives

Perspectives are the Power User feature of OmniFocus. Smart Lists are the Power User feature of 2Do. You can use Smart Lists, along with 2Do’s powerful search feature, to slice and dice task lists in a number of ways. I typically use them as a replacement for Perspectives, grouping related contexts into task lists. You can also use Smart Lists to identify tasks with start or due dates in the future, with different actions associated with them, and much more.

While 2Do’s search is powerful, it is also kind of fiddly and hard to use. You’ll want to keep that advanced search page open while you set up your Smart Lists.

Other Differences

2Do has several features that OmniFocus doesn’t that I do not want to give up. These include:

Built In Tasks Reminders beyond “Overdue”

It’s one thing to put a task in your task list. It’s another to actually do it. I have a nasty habit of letting task managers turn into roach motels: tasks enter, but they never leave. With 2Do, you can add alerts to tasks to go off at arbitrary times. If something has a hard due date for Friday, but you want to be reminded about it on Wednesday, just set an alert. It’s almost like someone wedded Due to OmniFocus!

Focus Filter

Not to be confused with a similarly named OmniFocus feature, 2Do’s Focus Filter lets you slice and dice a long task list based on a number of useful criteria, and do it on the fly. Combined with Smart Lists, it lets you get a very specific view of your tasks in a way that’s a lot harder to do with OmniFocus.

Very powerful repeating tasks

This is a biggie. 2Do’s repeating tasks are very powerful, second only to Things in terms of flexibility. Tasks can start, or be due, on specific days each month, like the 3rd Friday, or Last Wednesday. I wish OmniFocus had that.

That’s not to say that OmniFocus doesn’t have some features that I would kill for in 2Do:

“First Available” Tasks and Sequential Projects

In OmniFocus, it’s possible to hide every action on a list, save for the specific, first “Next Action”. Similarly, if a project in OmniFocus is set to “Sequential”, subsequent actions are locked down, and can be hidden, until the next available action is checked off. For projects with huge numbers of actions, this is a godsend for not being overwhelmed. Too often in 2Do, I go to look at a project and get overwhelmed by the number of tasks. 2Do’s creator suggest using starred items for this.

Review

OmniFocus’s built-in Review feature is something I miss a lot. It’s a great way to build a habit of checking on each individual project and see its status. There’s nothing keeping you from doing it in 2Do, but it’s not something that’s baked in as a feature.

Location-based Contexts

While 2Do has location-based alerts, they’re not as robust as OmniFocus’s location-based contexts. 2Do’s locations are tied to a specific geographic point, while OmniFocus lets you base context locations on a search. Both approaches have their strengths, but I prefer the flexibility of being able to have multiple options for a post office or a grocery store, depending on where I am.

Then again, living in a dense urban area, location-based anything tends to be a dicey proposition, with alerts firing off when I’m nowhere near the specific location.

Finally, there’s places where OmniFocus and 2Do are functionally similar enough that it comes down to preference.

Hide/Show Scheduled

While 2Do lacks OmniFocus’s ability to hide all but the next action in a project, being able to hide future tasks in OmniFocus and 2Do is quite easy. I swear by it, especially for my day job.

Email Capture

Email to 2Do is a great feature, basically building an email client into 2Do that processes any email that matches certain rules into tasks. OmniFocus Mail Drop is a more hands-on feature—you need to send or forward emails to a secret email address before they get turned into tasks. The end result is essentially the same: a new task in your Inbox (or default collection list for 2Do). 2Do has the ability to add tags to captured emails, but you’ll still have to do some manual organizing no matter which app you use.

Sync

Another reason I was wary of switching to 2Do is that it has neither a native sync, or an iCloud based sync. I’m currently synchronizing my various installs with Dropbox, which isn’t ideal—but only because I’m trying to use Dropbox less. (It’s a political thing.) The sync itself is fast and flawless. So is OmniSync, OmniGroup’s proprietary syncing engine for OmniFocus. I’ve never lost a task or change in either app.

Conclusion

I hope this helps the inveterate task management app switchers out there figure out how to go from OmniFocus to 2Do. Or, if you want to go the other way, I think this guide should be just as helpful. The important thing is finding the tool, or set of tools, that work best for you. I don’t know if 2Do is that tool, but it certainly has some charms, and the more I learn how to use it, the more I can see its advantages and work around its disadvantages.