Task Manager Burn & Build Notes

Image of a burning forestI started what I call my Task Management Burn and Build about a month ago. I’m still not completely comfortable with where things stand now, but it’s time to stop fiddling and try to settle into my new task management workflow and see exactly where it falls short. I’ve come across a few things worth noting. While they won’tt apply to everyone, I’m sure they aren’t completely unique to me.

Please, I Want To Pay

If I’m going to use a software or service to run my business, and life, I want to be sure it’s supported and around for a long time. So not only am I willing to pay for the software or service, I consider it a positive feature that enhances the product.

Of course, there has to be a value proposition that’s in my favor or at least equal. For example, Asana and Trello were very similar in the way I was using them. To get the features I wanted from Trello would cost me $40 a year, while the free level of Asana has all the features I would need. The least expensive paid level of Asana is more than I would be willing to pay, especially since it doesn’t add any features I would use. While Trello did seem to be a slightly better fit for me than Asana, I also thought a little less less of Asana because I wouldn’t be paying for it. Free wasn’t something that added to Asana’s ability to pull me in. If I find, after a year, that I’m not using Trello enough to justify the cost I might switch to Asana. If I can’t justify $40 a year then the service wouldn’t be integral to my workflow and free isn’t a detriment since I wouldn’t suffer it it went away.

Software & Services Can Go Away

Similar to wanting to pay for a service I use, I also want to make sure that the software or service has a business plan. I’ve never committed to If This Then That (IFTTT) because they didn’t have any visible business model. They implemented one recently but it doesn’t seem all that robust (or profitable). My fear would be that they either just fold up, or get bought up and radically changed.

Zapier is a smilier, but more robust, service like IFTTT. They also have a limited free level but have subscription plans. While Zapier could certainly go away I would lean towards using it because I view them as more stable. But as I said above, there has to be a value proposition in my favor and at this time I can’t justify the cost of a Zapier subscription.

Of course, any software or service can go away. So I try to keep data in a format that’s transportable between different software and services. Unfortunately this doesn’t seem to to be a viable option in the task managers that I looked at. Some do have import/export options but getting compatibility between different applications could be a major effort and not something I would count on.

One Size Doesn’t Fit All

I’ve always tried to keep all my task and project management in one application, which was OmniFocus for the last two years. As I experimented with my new task workflow I came to realize there wasn’t one application that would do it all. Picking one app would mean that I would lose certain features and abilities. As I looked through other apps it became apparent that if I wanted to use just one app then that would mean staying with OmniFocus. And I already knew that OmniFocus was falling short.

OmniFocus is Apple only, iOS and Mac OS, and it can’t be shared with others. While there is more automation around new versions, getting tasks into OmniFocus typically requires more steps.

Todoist makes it easy to get tasks into it. There’s a lot of integration with other web services including IFTTT and Zapier. OmniFocus provides no real integration although tasks can be added using email if the OmniSync service is used.

While templates can be created for Todoist projects, I can’t leverage them because I don’t have very many standard projects. So I found it tedious and time consuming to add medium to large projects. Making this worse was that the way Todoist handles subtasks just doesn’t work for me. I tried several alternative methods but none really clicked with me. (In short, subtasks can’t be set to repeat with the parent task. They appear as done when the parent repeats. If they are set to repeat on their own they immediately re-appear with the new date when marked as complete. This makes it hard to quickly see what still needs to be done.)

On the other hand I like the ability to plan visually with Trello, especially for larger projects. But I have a lot of shorter projects (usually recurring) or a single task that needs to be repeated on a weekly basis. I found Trello cumbersome for these short and single task projects. They could be done, but it was always uncomfortable and I never lost the feeling that I was forgetting something.

While Todoist could share projects I found Trello easier for others to use. Even if they weren’t familiar with Trello it was easy for them to go into Trello and see where the project stood. They could do this with the free plan and it’s a good way to keep others updated.

Current Status

Eventually fiddling with task apps becomes counter-productive. I’ve settled into a system which seems to be working for me. It was kind of an accident, although it was a bit intentional. As I set up new projects in Todoist and Trello I saw what worked and what didn’t. The same happened when I moved projects from OmniFocus to Todoist and I did encounter some workflows that failed fast. Since I hadn’t deleted the projects from OmniFocus it was easy to move back as I tried to find a solution.

I’m currently using three task managers. Just writing that makes me cringe since I think thats’s two too many. But things settled into a natural order and I think it’s made me more productive.

Todoist has settled into the role of the task manager for my personal tasks. Since I work for myself there’s a group of tasks that can be either personal or business. For example, is reading tech articles personal or business? I used to think that if I had two task managers, one personal and one business, I needed to properly classify each and every tasks. Instead, since it’s easy to get tasks into Todoist I use it for tasks that come to me during the day. These are mostly personal tasks and a few that fall into that middle ground.

Even though I now have two task managers they naturally split my tasks in a way that allows me to mode shift in a productive way. During the time I consider my workday I use OmniFocus and only OmniFocus (OK, occasionally Trello for planning or to update others, but mostly OmniFocus and never Todoist). The work I do at my desk (or what passes as my desk if I’m on the road) and work related to a customer’s project are in OmniFocus. This keeps me focused on my business projects. I don’t even see my personal tasks since Todoist isn’t even open, so there’s nothing to catch my eye and send my down a rabbit hole. The vague personal or business tasks aren’t anything that needs to get done during my workday so being in Todoist isn’t a problem. They are typically articles to read, emails to answer and similar things which I typically do after my workday, or for a limited time during lunch.

So multiple task managers has helped me focus and remain productive during the day. Another benefit is that I’m no longer checking off completed items in OmniFocus during the day, or if I am it’s because of progress towards a business goal. When everything was in OmniFocus I would ofter check off a number of small personal tasks that didn’t make progress towards a major goal. Despite not having any substantive progress I would feel like I did a lot and could relax, after all I finished 10 tasks from my list. That made it hard to stay focused and motivated.


The big lesson for me from this burn and build is that not only don’t I need one task manager for everything, I’ll be more productive and focused using two. It helps me keep my focus in the right mode, business or personal.

I’m still looking for a way to replace OmniFocus since it’s not cross-platform. This is less critical now that I have other apps in my system so I won’t dedicate a lot of time to the search, but I will remain on the lookout.

Todoist is working well, but I’m not optimistic that it will be changed to eliminate where it falls short for me. I don’t like the way sub-tasks work but it is a valid method and I’m sure there would be many complaints if it was to change.

I’m sure I’ll make some tweaks over time, but for now my task management system has been rebuilt and is ready to use.

Synology News: DiskStation DS1517+ and DS1817+ introduced

Synology DS1817+
Synology DS1817+ (image from Synology)

The DS15xx+ and DS18xx+ have always been my go to solutions when I needed a workhorse NAS. I currently run a DS1815+ as my primary NAS and an older DS1511+ has been a reliable backup destination since it was replaced by the DS1815+. Synology updated both those models for 2017, releasing a DS1817+ and a DS1517+.

The press release calls them “5-bay and 8-bay tower servers” which, while not completely incorrect, could be misleading. They are oriented horizontally and appropriate for a shelf. They don’t take a lot of space vertically.

They support the new M2D17 M.2 SATA SSD adapter or a 10GbE network interface card, both of which are optional. The M2D17 allows setting up SSD caches without using an internal bay.

Each NAS also support up to two of the new DX517 expansion units. Each DX517 adds 5 drive bays. The new models can be expanded to 16GB of memory which is now faster dual channel memory.

The two new models, along with the new expansion unit, all come with a 3 year warranty. This can be expanded to 5 years in some countries.

While they aren’t available for delivery at this time, only pre-order, Amazon (US) lists the DS1817+ w/8GB RAM for $950 and the DS1517+ w/2GB RAM for $700. These are about the same as the prices for the previous models when they were originally released, although the price has dropped now that they are the old models. This is especially true for the DS1815+ which is down to $835 (w/2GB RAM) on Amazon and B&H Photo.

Synology Press Release: Synology® Introduces DiskStation DS1517+, DS1817+, and Expansion Unit DX517 – News | Synology Inc.

Google vs. Symantec Certificates

If you run a website that uses SSL there’s a 30% chance you use a SSL certificate issued by Symantec (they bought Verisign’s certificate business, among others) and this affects you. If you use Google Chrome to browse the web, and well over half of us do, then this will affect about 30% of the websites that you visit.

The cornerstone of SSL encryption is trust. When I browse to a site that has SSL encryption I have to trust that the certificate correctly identifies the site. If I’m browsing a site like this one, which uses HTTPS (SSL encryption) but doesn’t contain any personal data, doesn’t require a password, and doesn’t have a store, then all I care about is that the traffic is encrypted. I can use Let’s Encrypt which is free, but doesn’t make any attempt to identify the site owner. All it does is verify that the certificate requestor has access to the domain/website. But if I visit a web shop or financial institution then I want to be sure the site is who it says it is. This puts a greater burden on the certificate issuer to verify the legitimate identity of the certificate requestor.

There are various levels of certificate validation. Certificates such as Let’s Encrypt are at the bottom of the list. They encrypt the data to and from the site, but do nothing to verify the identify of the site’s owner. It just provides domain validation – the certificate matches the domain it is installed on and the person requesting the cert had management access to the domain. The bad news here is that the site shows a valid certificate and most people don’t know about the various certificate levels. This can lead to abuse. For example, certificates with PayPal in the domain name can be used for phishing. For example, paypal.com.dsfwrfece.ru could be issued and used for a phishing email. While this is an abuse, it is not a violation of the rules certificate authorities are expected to follow. The goal of encrypting everything is bumping against how people interpret that green lock in their browser address bar.

Then there are higher levels of certificates and unlike Let’s Encrypt these certificates are not available for free. At the highest level are Extended Validation Certificates (EV Certs). EV Certs validate the legal entity that owns the website. Between the domain validation and EV certs are organization validation certs. While there are differences among issuers, these certs generally validate an organization and it’s authority to administer the website.

The hub of trust among all these certificates are Root Certificates that are included in the operating system. (In some cases they may be in the specific software or browser.) These root certificates are then used to determine if the website’s certificate can be trusted. Google documents their Root Certificate Policy here.

Google has determined that Symantec violated these policies and is reducing their level of trust in all Symantec certificates. While no action has yet been taken (except possibly in the latest developer release), beginning with Chrome 59 (currently Chrome is on version 57 in production) Google Chrome will begin to decrease the length of time they consider Symantec certificates valid. By the time Chrome 64 is released the certificates can only be valid for 9 months. This will require Symantec to issue certificates more frequently and gradually age out certificates Google feels can no longer be trusted.

Google’s announcement was of their intent and Symantec disputes the severity and extent of the problem so this may all get worked out before any action is actually taken. This sort of thing can have a big impact on Symantec’s certificate business since their product, at its core, is trust. When DigiNotar had a security breach that resulted in fraudulent certificates being issued they were dropped by all major browsers and went bankrupt within a month. So Google’s actions are less severe than some past cases, and have yet to be followed by other major browsers.


If you have a Symantec certificate that needs renewal in the near future I’d recommend switching to another issuer if this hasn’t been sorted out yet. I’ve used DigiCert in the past and find their customer service to be excellent so I can recommend them. If all you need is domain validation, to encrypt all traffic (and get a ranking boost from Google), then Let’s Encrypt is free and suites the purpose.

Personal VPN

There’s been a lot of privacy talk in the news recently, triggered by the U.S. House and Senate voting to stop new ISP privacy rules from taking effect. This won’t be a discussion on the politics, but since the President is expected to approve the measure it’s worth considering options if you’re concerned. Plus, it’s never a bad time to review security. One thing worth mentioning is that the affected rules were slated to take effect at the end of this year, so the change simply maintains the status quo. On the other hand, I don’t know of anyone outside of the big telecom companies that considered the new rules to be a bad thing for consumers.

Generally, VPNs (Virtual Private Networks) have been used to provide security when you’re on the road, using unknown networks. They provide an encrypted tunnel between you and where ever your VPN provider enters the internet. A VPN can also be used to keep your ISP from seeing what sites you visit although they are rarely used for this today.

Most ISPs provide an option to opt-out of tracking, although it may be hard to find out how to do this. If you want to limit ISP tracking then your first step would be to hunt down this option and opt-out.

Some things to keep in mind when using a VPN from your home:

  • VPNs will negatively affect your performance. This may not be noticeable and the impact will vary over time, but all VPN services will impact performance at least some of the time.
  • While data is hidden from your ISP (although they will know you are using a VPN), your VPN provider will be able to see all your traffic. Like your ISP, they could track you.
  • A VPN service isn’t a ironclad security or privacy guarantee. Websites can still track you through your browser usage. Plus, you need to trust the provider to properly implement the service.

There are hundreds of VPN services out there and choosing one can be daunting. There are a few that I have extensive experience with and can recommend.

TunnelBear is a Canadian company that offers VPN service on Mac OS, Windows, Android and iOS. They also offer a Chrome plugin to encrypt browser traffic. They don’t keep any logs but they also don’t allow torrenting. Pricing is $50 for a year of unlimited use, paid in advance. If you want to subscribe on a monthly basis it’s $10/mth. They offer a free plan that provides 500MB of data per month. The free plan can also serve as a trial.

The iOS client uses IPSec/IKEv2 which requires UDP ports 500 and 4500 which may be blocked on some networks. I didn’t have any issues when using TunnelBear around town. I did have to enable IPSec Pass-through (which opens those two ports) on my home router in order to use TunnelBear when at home.

Cloak VPN is based in the United States. Their VPN clients are limited to Mac OS and iOS. Cloak is pricey for a yearly subscription at $100, which provides unlimited data. But they offer smaller plans which can economical if you only need sporadic use of a VPN. A 5GB/mth plan costs $3 while an unlimited weekly pass runs $4.

Cloak is one of the easiest VPN clients to use. It can automatically connect to networks and enable the VPN, blocking traffic until the VPN connection is active. You can also identify trusted networks so that the VPN is not enabled on these networks.

Synology VPN (or VPN+): If your goal is to prevent your ISP from tracking your internet travels then Synology VPN is a non-starter. The VPN server is on your Synology NAS (or router) and all traffic will leave the VPN tunnel before it heads off on the internet via your ISP. While it provides security when your out on untrusted networks it will route all your mobile traffic through your ISP, giving it even more information.

Another option is a whole house router, where your router connects to a VPN service as a client. You’ll need a router that supports this setup and a reliable VPN service. These days many routers do list a VPN feature, but this usually means the router runs a VPN server that you can connect to when you’re out and about. This has the same drawback as the Synology VPN in that it doesn’t hide anything from your ISP. I’ve never been able to justify the cost and complication of a router based whole-house VPN client so I don’t have any actual experience with this type of setup.

If you want more information here are some places to start:

VPNs Are for Most People—Including You | The Wirecutter – This was updated March 24, 2017 and provides a VPN overview along with more details about what to look for in a VPN provider.

Best VPN Reviews | Best10VPN – Mega-list of VPN providers. As usual, never make a decision based on one internet site, but this can provide a good starting point.

How ISPs can sell your Web history—and how to stop them | Ars Technica – An overview of the recent legislative changes (or non-changes) and options for dealing with them.

iOS 10.3 Released

Yesterday Apple released iOS 10.3 for iPhone and iPads. This is a big one, especially under the hood. Apple is switching to the Apple File System (APFS) on iOS (eventually Mac OS will follow). While I haven’t had any issues, or heard of any, a file system change is a big deal. It’s possible that the file system conversion could break an app or corrupt data in a way not even the developer can fix. So be sure to backup your iOS device before installing the update. You may also want to put the update off a week or two and let other people uncover any issues.

This update did feel like it took longer than usual, about 25 minutes each on my iPhone 6s and my iPad Pro. My iPhone 6s also saw the battery drop from 100% to 87% after the upgrade. The iPad Pro only lost about 2% from the battery meter.

Other updates include:

  • Find My AirPods is now available in the Find My iPhone app.
  • There’s a new Today screen widget for the Podcast app.
  • Weather information is now available in Maps for iPhone 6s and newer phones.
  • Apple ID information has been consolidated and put front and center in the settings screen. The Apple ID Profile now also includes a view into your iCloud Storage usage.
  • iCloud calling is now available on Verizon so you can make and take calls when the iPhone isn’t around but other devices are.
  • Settings -> General -> About -> Applications should warn you about apps that may slow your phone (32-bit apps). I don’t have any so I couldn’t see this in action (or I do and it’s not working – I think it’s the former).

As usual there’s also a plethora of security updates to iOS 10.3.

Last warning – be sure to backup before upgrading, especially this time.

Mac Backup Programs – An Overview

Backup words on a chalkboardBackup applications are varied in both their abilities and price. Plus, people have different needs. The important thing is to have reliable backups. There are a couple things I consider essential in all situations, at least for individuals and small businesses.

  1. The backup must happen automatically and not require human intervention. Unless you have dedicated IT staff this will always be secondary to everything else and eventually get skipped.
  2. At least one set of files must be off-site, away from the computer where the data is used every day. The farther away the better, in order to avoid a situation such as a natural disaster that affects you and the offsite location.

I find the following backup programs well suited to meeting these needs. While some may have versions for Windows and Linux I’ve mainly, used Mac versions, and any Windows specific options are ignored (with one exception).


Arq is myMy favorite backup program for the Mac. It doesn’t provide any of its own storage (it’s not a service) but it does integrate with a large number of this party services. Naturally it can also backup to a folder on a external drive or NAS.

Arq can maintain a file history and works similarly to time machine. You give it a quota for space (or money budget for paid services like Amazon S3) and Arq will keep copies of old files until that quota is filled, then start deleting old files.

It can backup to Amazon S3, and Amazon Drive which are the cloud services I use regularly. It can also backup to Amazon Glacier, Dropbox, Google Drive, Microsoft OneDrive, Google Cloud Storage, and DreamObjects. SFTP destinations can also be used along with the already mentioned local storage or NAS.

A must have feature of Arq is that it will (optionally) encrypt the backups before the data leaves your computer. So even if the your cloud service is hacked your data is still encrypted, and only you know the encryption key.

There is now a Windows version although I don’t have any experience with it.


CrashPlan has been my long-time choice for Windows backup. I don’t have a lot clients with Windows machines, but this is my recommendation for friends & family. There are Mac, Windows and Linux versions.

The software is free for backups to local drives, to a friend’s computer, or to a second computer you may have. There are also a few other limitations with the free version, such as no unlimited saving of old file versions. They offer an online backup service with prices starting at $60/year or $6 per month for one computer. The rest of this summary relates to features in the paid subscription.

CrashPlan will keep an unlimited number of old file versions as well as copies of deleted files. You can encrypt the backup using your own encryption key (or theirs) and files are encrypted before leaving the computer. You may need to enter your encryption key in the mobile app or in a webpage for restore, so it is potentially less secure as there are more things that can go wrong.

One feature I like is an weekly email to summarize the backup status. This lets me know if a family member’s computer has a problem completing the backup, or if there’s been a significant change in the amount of data being backed up.


Like Arq, ChronoSync only provides the software, it is not a backup destination or service. In all the years I’ve owned ChronoSync I’ve never been charged for an upgrade, and there have been many, many updates. New features have been updated in addition to simply maintaining compatibility with macOS upgrades.

As the name implies. ChronoSync revolves around syncing, rather than a traditional backup. But these days it can be used as a traditional backup. ChronoSync can also connect to Amazon S3, Google Cloud Storage, or an SFTP server for backup or sync.

ChronoSync can also keep a archive of any replaced or deleted files. Whether or not an archive is kept, and for how long, is fully configurable. If you do a lot of transfer between Macs on a regular basis there’s a ChronoAgent to help manage these remote transfers.

Time Machine

Time Machine holds a strange place in my backup strategy and recommendations. I recommend everyone use it, although it can sometimes have issues and I don’t trust it as my only local backup. It comes with every Mac and it’s been extremely useful when I need to recover an old file.

I’ve actually never had a problem getting a file back when I’ve needed it. But I have had times where Time Machine tells me it can no longer use the backup and must start fresh. This doesn’t build confidence. Using a locally attached drive is more reliable than using a NAS (or Time Capsule) as the backup destination.

I find Time Machine useful and reliable enough to keep backing up to my NAS with it. It’s an inexpensive way to backup a Mac, but I recommend having a second backup. That second backup could be offsite and harder to get to or restore. I wouldn’t recommend two Time Machine backups (which can be done) as your only two backups.

SuperDuper! and Carbon Copy Cloner

I grouped SuperDuper! and Carbon Copy Cloner together since they are similar. Both, at their core, are applications that clone a Mac hard drive. I was a long time user of SuperDuper! and it worked great. Then Carbon Copy Cloner came out with version 4 which brought the software to a new level. I switched to it because of it’s ability to script the clone a bit more than SuperDuper! and it was possible to chain the clones together.

Carbon Copy Cloner also as a safety net feature which saves files that were deleted since the previous clone.

SuperDuper! is free to do a basic drive clone. The paid version adds scheduling, smart updates and scripting among other things.

Carbon Copy Cloner has a free trial. The paid version, needed once the trial runs out, is slightly more expensive than SuperDuper! but does have more features.

Either program will work and if SuperDuper! meets your needs then you can save some money by using it.

Additional Backup Software

I have limited experience with the following Mac backup software. What experience I have has been good and they all get good reviews in the tech community.


Backblaze is similar to the previously mentioned CrashPlan. It provides offsite (online) backup with Personal and Business subscriptions. Unlike CrashPlan the only backup destination is their cloud.


Carbonite is another online backup service. Like many of these online services it will only backup user generated files for the lower-cost personal plans. If you don’t use the standard windows or Mac user directories then some data files may be missed by the backup.


I used to recommend Mozy several years ago. Then I had problems with their software around the time their ownership was also changing. Overall it was a terrible experience and my solution was to pick another service. I haven’t recommended Mozy since. They’ve changed hands again (possibly more than once) and are now owned by Dell. I still wouldn’t recommend their personal plans, but I would consider their business plans as they seem much more focused on business services.


When I first used SpiderOak they were a new offering that was much like Dropbox, it really wasn’t a backup solution. I liked them back then because they were focused on security. I moved away from them because Dropbox and iCloud provided enough security for the types of things I was storing in the cloud and they provided integrations with more apps.

The other online backups I mentioned tend to provide unlimited storage space (although with other possible restrictions) for a set price per device. SpiderOak, because it provides both Sync and Backup, has tiers for the space you want (100GB/250GB/1TB). The charges are reasonable although you may want to consider alternatives if you don’t need sync and have only one device, with a lot of data, to back up.

Summing It Up

All of these backup solutions provide a free trial and you should take advantage of this to see which works best for you. For online backup solutions you should be aware that the first backup may take a long time. If you’re using a free trial I’d suggest picking a subset of files so the backup will finish and you can test out a restore. Generally, home and business cable ISP plans have a slower upload than download speed and it’s the upload speed that matters. If your ISP has bandwidth caps this could also be an issue. Your first backup will use a lot of bandwidth but future backups will be less since only new and changed files will be backed up.

I use Arq as my primary backup software and have for a long time. Currently I use it to backup to Amazon Cloud Files and Amazon S3. I also use Time Machine regularly although I keep very little data on my computers, most is on my NAS. I like the ability to quickly grab an old file without having to pull out any disks or wait for an online download. Finally, I use ChronoSync to move files around locally and to create local backups.

In putting together this overview I’ve come to realize that the software I’ve used for years has added new features that I could be using but haven’t explored. I’ll be exploring ChronoSync as a more complete backup solution including cloud backups. I also noticed SpiderOak has become a real backup solution in the time since I used it. It may be worth revisiting.

While your needs may vary, any of these backup solutions should reliably protect your software. The trick is picking the one that meets your specific needs. There’s no excuse not to have backups.

Notes About Trello

I’ve been re-evaluating my task & project management system and Trello is the first tool I decided to take a look at. Trello is a task management and collaboration tool based upon the kanban system. It’s very visual and designed for team collaboration but I would not consider it a true full-featured project management tool, as it lacks the heavy project management features such as gantt charts and scheduling. It’s web based and has numerous integrations with other apps, including Zapier and Harvest. There are both iOS and Android mobile apps.

While Trello does emphasis tracking and planning among teams, I have no need for these features and looked at it as a single user. The collaboration features don’t get in the way or make Trello difficult to use. This overview is from my perspective as a solo user and I won’t discuss any of the collaboration features.

Trello does have a free level. While this let me kick the tires for most of the Trello features I would need, it was a little short of features and capacity if I was to use it as my primary planner. Business Class, at $120/yr., is the least expensive subscription on their main pricing page. But a little digging will reveal a Trello Gold subscription at $45/yr. (or $5/mth). Trello Gold provides the added features and capacity I need. These are mainly repeating tasks and up to three power-ups per board. It also adds saved searches, which may prove useful in the future, along with larger attachments and visual customizations.

At this point I did sign up for one month of Trello Gold in order to continue my evaluation. While it has the benefit of being the first solution I actually used (as opposed to just reading about) it is a strong contender to form the hub of my task and productivity process.


Power-Ups are the way Trello provides enhancements and integrations to its basic offering. Power-Ups can be enabled on a per-board basis. Trello Gold allows three power-ups to be enabled per board, the free version allows one per board, while the business subscriptions don’t have a limit.

Power-ups can’t be managed through the mobile apps. For the most part they can’t be used at all on the mobile app, although the ones I used did degrade gracefully. For example, the Google Drive power-up can’t be used to attach a Google Drive file, although existing attachments can be opened.

Since Trello is a popular service along with being web based and having a public api there are a lot of integrations with other apps beyond just the Power-Ups. For example, if Harvest isn’t your time tracker but Toggl is, there’s a Chrome extension that will place the Toggl timer button on each card.

Power-Ups I used

Calendar: Displays a calendar with the tasks listed according to their due date. Completed tasks have a line through them indicating completion. Only tasks on the current board are shown. The calendar is not available on mobile apps.

Card Aging: The card will visibly age over time if there’s no activity. Thresholds are 1, 2 and 4 weeks. By default the cards become more transparent over time. There’s also a Pirate Mode where cards visibly age and tear. This (especially Pirate Mode) provides a quick, visible way to identify tasks which have been dormant if you are viewing the board on the web. The mobile apps do not show the card aging.

Card Repeater: Does what it says on the tin. Allows cards to be repeated on a set schedule. More on this later as it’s key to my use of Trello and deserves it’s own discussion. For now I’ll just say that it’s not tied to task completion and due dates are not adjusted. The mobile apps cannot be used to set up the repeat.

Google Drive: Provides links to your Google Drive account to show information about attached files. New documents can also be created from within Trello without having to exit to Google Drive. File can be attached from Google Drive without the power-up but the card will not show updated information as the file changes.

In addition to the Google Drive power-up there are power-ups for Boxand Dropbox that will display current file information for attached files. But unlike the Google Drive power-up, new documents cannot be created from within Trello. Files can be attached without these power-ups enabled, but their info will not be updated. Files can also be attached from OneDrive but there aren’t any enhanced power-up features.

Harvest time tracking has a Power-Up. I enabled this early on but found I could turn off the power-up and still have integrated time tracking on all boards as long as the Harvest chrome extension was enabled, although advanced features weren’t available. Trello help implies that the power-up must be enabled for even basic tracking. Enabling the Power-up does provide additional features such as showing the total time tracked to a board and attaching a time report to a card. Harvest integration is not available on the mobile apps.

Package Tracker: This integrates with Packagetrackr and shows the progress of you shipment. The ETA or status is shown on the front of the card and the tracking detail is shown on the back of the card. The ETA/Status and tracking detail are not shown on the mobile apps, although there is a link to the tracking information on the Packagetrackr website.

There are numerous other power-ups available, but these are the ones that caught my attention as I looked to replace my current system.


Boards are what contain all the lists and cards. Each board is it’s own self-contained world. Cards can be copied and moved between boards but that’s about it. For example, calendars (if enabled) are limited to the current board. There’s no way to get a view across all boards, at least within Trello.

Board with 3 lists and 1 card
Board with 3 lists and 1 card

If the Calendar Power-Up is enabled then there’s a iCalendar formatted read-only feed. (Some calendar programs will refer to this as CalDav which also uses the iCal format.) Any card with a due date will show in the calendar. Completed cards will have a line through their name. The list name is shown (“Active” in the screenshot below).

Shown in BusyCal
Shown in BusyCal

Generally, each board will be dedicated to a project, and only one project. Boards can be closed when a project is finished, although it can be re-opened again if you need to view it. If you assign cards to yourself then you can see all cards assigned to you in your profile. This profile view can be sorted by project or due date, so it does provide a bit of an overview for your tasks across boards.

Boards can be filtered on labels, due dates and who a card is assigned to. This makes large boards more manageable.

Labels exist only within the board they were created on. Creating a new label, or renaming a default label, on one board will not carry over to other boards.


Lists are what contain the actual cards and boards can have many lists. Lists must appear side-by-side on a board, no stacking allowed. This can make for a lot horizontal scrolling. To keep scrolling to a minimum I try to keep the most used lists to the left side of the board since the left side always appears when first switching to a board.

All cards in a list can be archived at once. I keep a “Completed” list for most projects and as cards are done I move them to this list. This way I can quickly recap accomplishments at the end of the week. Once I’ve reviewed them at week’s end for my report-out I can archive all the cards at once.


As mentioned, lists contain the actual cards which are the tasks which need to be done along with any notes related to the task. Boards and Lists are simply ways to organize the cards which are the nuts & bolts of Trello.


I love checklists! Much of my work is done using checklists. In OmniFocus I often use sub-tasks as a checklist. In Trello, multiple checklists can be added to a card. The items are displayed on the back of the card where they can be checked off. The front of the card shows the status of the checklist – how many items are checked off out of how many total items.

A checklist with 7 items
A checklist with 7 items
Showing 1 of 7 items checked (bottom row)
Showing 1 of 7 items checked (bottom row)

Multiple checklists can be used on one card and they can be copied between cards with having to copy the whole card. If a card is copied the checklist is (optionally) copied and all items are unchecked. If the Repeat Card Power-Up is used then checklists are copied with all items unchecked.

I’m still struggling with some parts of my Trello workflow, but checklists work really well for me and are one of the features that keep me evaluating it.

Repeating Cards

One of the things I like about OmniFocus is its ability to hide tasks which I can’t be working on. I dislike a long list of tasks, even if I know only the first few need to be done. Just seeing the long list can make me anxious and inhibit my ability to focus.

I like the way Trello handles repeating cards. Although it is limited and required some tweaking to work the way I want.

One of the biggest draw-backs to repeating cards is that they are not tied to completion. If I repeat a card with a due date then it will repeat without any due date. So repeating is a good name, rather than recurring.

Another feature of repeating cards is that any comments attached will also be repeated, as will attached documents. This can be both beneficial or detrimental, depending on your expectations. Generally, I want attached documents to remain, but comments I want to be specific to that instance of the card.

There a great deal of flexibility in scheduling the repeat frequency. They can be scheduled to appear every 1 to 30 weeks, on any or all days of the week. They can be scheduled to appear every 1 to 30 months, on a single date in the month. They can be scheduled to appear every 1 to 30 years, on a single date in the year.

Schedules such as the second Tuesday of every month are not possible.

You’ll notice I wrote scheduled to appear. This is because the card will not appear until the repeat happens. It’s worth saying again that the repeat is not at all related to a completion date.

Repeats are tied to the original card it was set up on. So while I said comments and attachments are copied when a card repeats, they are copied from that original card. Comments or attachments added to the newly created card will not be carried forward to future cards.

Archived cards will continue to repeat. The repeating will stop if a card is deleted or moved to a different board. The history of the card contains a link back to the card it was created from, so it’s relatively easy to go back and change any repeats that are set up.

How I’m Using Repeating Cards

While I’m still tweaking how I use Trello, my current process for repeating cards generally uses the following rules:

My general task board (which I call Tickler) is where most of my repeating happens. It gives me a view of the week, with a list for each day. I also have a list called Templates. Cards which repeat are set up in the Templates list. I typically schedule the repeat for 8PM on Sunday and have the cards appear in the column for the day I will do them the following week. This serves as a quick way to find repeating tasks (cards), especially while I build trust with Trello. I can see what cards are set to repeat and quickly make changes to the schedule or the card itself.

This allows me to achieve my goal of not seeing tasks before I can actually work on them. Although, the out of sight nature of their setup is taking some getting used to. I’m paranoid I’ll miss something so the Templates list at least lets me know what tasks are set to repeat.

So far this seems to be working for me. While cards can be copied and moved to other boards, repeating tasks must appear on the same board as the card that is creating them. If a card is moved to another board then the repeat is removed, it is not continued on the new board.

Summing It Up

I’m liking Trello a lot and it seems like the new task/project manager to beat for me. At $45 per year I find the gold subscription worth what I get. The free level is a little lacking, plus I like to support software I use so that it’s development continues. I would have a hard time justifying the cost of the business plans for my own use.


  • Simple and intuitive to use.
  • Repeating tasks are out of sight until I can actually work on them. Although I still need to work out my trust issues related to this.
  • A lot of integrations with other web apps. I haven’t mentioned Zapier integration, but Zapier does support a lot of Trello actions, Much more than IFTTT.
  • I like seeing a visual overview of the project. I often plan using sticky notes or index cards and this feels very much like that.
  • Can add tasks or update cards via email.
  • Free version is a good introduction to Trello capabilities without any expiration.
  • Very list (and checklist) oriented which fits with the way I like to work.


  • No view across all projects/boards. Each project is a silo. This can make it a little hard to view my workload when I’m running projects in parallel.
  • Due dates aren’t adjusted and kept for repeating cards. I get around this a bit by having a list for each day of the week and then create the card in the appropriate list. But I would like to have due dates adjusted and repeated so they appear on the calendar and in the calendar feed.
  • Cumbersome horizontal scrolling for large boards. Stacking lists might be nice although then I might complain about differing lists sizes making it hard to know where lists are.
  • Not well suited as a simple reminder tool.

I’ve installed a couple other task management apps but they haven’t seemed as suited to me as Trello. I could waste hours upon hours exploring task management apps and then even more hours tweaking them. My current Trello Gold monthly subscription expires in 10 days. Unless something else catches my attention before then I plan to renew Trello Gold for a year and stop searching.