How to choose a task or project management tool

Born out of discussion in The Productivists community and my own (ongoing!) search for an ideal task/project management tool, I thought it could be helpful to try to define in broad strokes how to start your own journey of selecting the best tool for you. This can apply whether you’ve never used a task manager before, or are simply switching tools.

From this point on I may refer to task/project management by “T/PM” to save time/space.


My goal is to make this an easy and fairly comprehensive reference of the things you might want to keep in mind when evaluating and deciding on a T/PM tool. In reality there are a ton of things to consider, and I hope to touch on most of the important ones. So this guide will be a little longer than I might prefer. And while the following may feel like a somewhat exhausting (if not exhaustive!) list, fortunately you don’t need to pay close attention to all of it. It’s simply intended to make you aware of options or criteria you might not have considered otherwise, or which it might have taken you a while to become aware of through trial and error (as I did).

So this is my humble attempt to share the insights of my own long search for the ideal T/PM tool. Feel free to skim and take from it what is most useful to you!


Get the Overview

If at all possible, I recommend reviewing the below before you dive in to big lists of tools or review roundups, etc. Hopefully it will prime your mindset to help you focus on the options most likely to be relevant to you when you do get into sorting through the many that are available.

Evaluate the Market

Once you have an overall familiarity with these criteria and differentiators, and have hopefully put them into a rough order of personal importance, then you can evaluate any options you come across against your personal criteria and make a shorter, more relevant list of choices for yourself. Ideally this will become a semi-intuitive process based on the internalized categories and criteria here, and any other criteria you have come up with.

Seek Real-World Examples

One thing I strongly recommend is to seek out videos of the actual interface and workflow of any given tool you’re considering. Often the UI may look nice in screenshots, but the actual workflow is clunky, or they even used mockups on their website, and the interface itself looks different (this is a particularly shady practice in my view). The best sources for real-world looks at app UI and workflow are their official documentation, and YouTube (or other) videos, either from the company itself, or better yet from reviewers or users doing instructional videos.


In the end nothing can substitute for personal experience! Fortunately a majority of tools out there offer some form of free version, demo mode, or at least short-term free trial. Even for those that don’t you can often get one simply by requesting it from the author.

But I encourage you to not spend too much time on testing specific apps when you’re still early in your search process. Narrow your options first, if you can. Try to focus your actual testing time on the most promising candidates.

What is Best is Personal (Context is King)

When choosing a T/PM tool it’s important to keep in mind that there is no “best” overall tool. There are only tools that are better for one person or another. So the critical thing to do is to really figure out what you want, and that starts by asking yourself why you want a T/PM tool in the first place, and getting a clear understanding of the context you’re coming from in your search. Are you new to T/PM tools, or trying to find a better one than what you already use? Do you want to structure your life or your business or both? Do you have a lot of tasks and/or projects, or just a few? Are you more or less tech savvy or inclined to use in-depth, sophisticated tools? Etc.

This will help you connect with and prioritize much of the following criteria. For an obvious example, if you want something solely for personal use, it will largely eliminate collaborative features as a significant consideration for you. Likewise if you are picking something for a business, you may be able to expense it, which might affect how much you’re willing to pay. Etc. Just do your best to think about your goals in adopting a T/PM tool.

Tool Proliferation

We are living in a golden age of productivity tools. Nowhere is this more prevalent, in my experience, than in task and project management. There are literally 1000s of such tools. Maybe the number of note taking apps would beat it, but only because many are extremely simple and even unmaintained.

So we have 1000s of options, but realistically should only use 1 or at most a couple of tools at a time. That presents a huge challenge to actually picking a tool for ourselves. The key then is to actually put as much focus as you can on eliminating options as fast and as simply as possible, so that you hopefully end up with a much smaller pool of possible candidates, which you can then evaluate more in-depth.

How To Narrow Your Options


It’s difficult to consider criteria without a way to rank or compare them. When you’re evaluating a given app and you end up with two competing criteria (e.g. an app that meets all your needs but is more expensive than you want to pay), you want to have a way of deciding which is more important to you.

So in reviewing the following list of criteria, consider their relative importance to you and try to create your own personal ranking. If possible decide whether each one is a “deal breaker”, too, i.e. if the app does not meet that criteria it is automatically disqualified, or if it just heavily reduces your likelihood of choosing it. You can make reviewing the below list faster by simply skipping over any category of criteria you already know isn’t important to you.

Evaluate Criteria

There are many broad categories you can use to narrow your list of options. Let’s start with the easy stuff, which I view as the largest and most simple factors to consider, i.e. there is generally a clear yes or no, vs. evaluating more qualitatively. For example, “do I need offline collaboration functions and does this tool have them” should be pretty simple to determine, even if the details may have some complexity.

For most people I think these are generally the biggest considerations:

  • Price
  • Platform(s)
  • Collaboration
  • Design
  • Organization and Structure
  • Integration


This is a fairly straightforward one: how much can you afford to or are you willing to pay? If you imagine your ideal tool, what would that be worth to you?

Pricing Model

Another related factor might be the pricing model itself.

  • Monthly fee (SaaS)
  • One-time fee
  • Free
  • Open source I realize open source is not strictly a “pricing model”, but that is one component that can be considered here

A majority of new tools these days are SaaS, in other words you generally have to pay an ongoing monthly fee. If this is an absolute deal-breaker for you, then you eliminate quite a lot of tools from the beginning. The same is true if you really prefer open source. But you do want to be sure that you absolutely would not consider a monthly subscription or other pricing model that you don’t prefer.


Obviously if the tool you want doesn’t run on the device(s) or OS(s) you have, then it’s not much good to you. As a Windows user I’ve had to ignore a vast array of awesome-looking tools that are Mac-only, like Things 3, Omnifocus, Tinderbox, and more. For most people a change of platform is simply not an option when considering adoption of a new software tool.


This is clearly the most broadly available way to make an app and its functionality available, and this is probably why many – if not most – modern task managers at least start out web-based. But there are some limitations to this approach, including challenges implementing offline features, poor interaction on mobile devices, lack of notification functions on some platforms, etc.


For those of you who live on your mobile device this can be a huge deal breaker, and is one of the reasons why platform considerations are high on the list of criteria to consider first. With mobile in particular it’s often important to evaluate not just whether they have a mobile app for your platform, but how mature and polished it is.

A good example of why this is important can be seen with ClickUp, which by many user’s accounts has had a buggy and slow mobile app for much of it slife. They recently (December 2020) released a total rewrite, however some early reports are saying that many features are missing (which is often the case with ground-up app rewrites). So the quality of the app can be as important as its mere existence on your platform of choice. You can get some idea of this of course by reading reviews on the respective app stores, or ultimately testing yourself, but the latter should be a last resort since it can take a lot of time to find the rough edges.


Windows, Mac, Linux, that’s basically it. You could argue ChromeOS maybe, but nah, let’s not. 😉 So it’s as simple as determining whether there is there an actual, dedicated, stand-alone app for your desktop operating system of choice. This can provide better performance, more integration with other desktop tools or functionality, and other advantages. In short, a more “native” experience. But this is not critical for everyone by any means and only a subset of the available tools have desktop apps. So if this is a key differentiator for you, congratulations, you’ve just narrowed the field considerably!

Design: UI, UX, Navigation, and Aesthetics

I’m going to lump all of these together here because the borders can be fuzzy between these concepts, and even when they aren’t, for the end user it often boils down to how it “feels” to use the tool.


Basically, how do you get around in the application. This obviously relates to many other things both in this category, and others (e.g. Organization and Structure), and it can be surprisingly personal as far as what people prefer. Usually I find this to be fairly easy to determine just by looking at some documentation or demo or review videos of the app in question. If it “clicks” and makes sense to me intuitively, then it’s likely to be a tool I’ll enjoy using. That said, sometimes for a tool that is good in most other respects, it can be worth getting used to a more idiosyncratic navigation scheme, but I think it’s generally the exception rather than the rule.


This is extremely personal and also hard to quantify or necessarily even compare. But for most people “you know it when you see it”. You can generally look at a screenshot of a tool, or at least a video, and say whether you like how it looks or not.


This is essentially the interactive version of aesthetics above, and often requires that you actually test the tool in question. It can come down to microsecond differences in responsiveness, the size of clickable areas for buttons and other interactive elements, or good vs. bad placement or existence of things like “toast” notifications, pop-ups, tool-tips, etc. Often times you’ll know within just a few minutes of starting to use an app whether you like how it feels or not.

Natural Language Processing, “Command Palettes”, etc.

Although both of these are relatively new concepts in UI/UX, they can both be tremendous workflow enablers, either one of which can make many of your interactions with the tool faster, easier, and more seamless.

Natural Language Processing (NLP)

When it is used in task managers this usually refers to the ability to create tasks, set dates and reminders, etc. simply by typing in more “natural” language, e.g. “Take out the trash at 9AM next Tuesday @Chores” would be automatically converted into a task in the “Chores” category, set for 9AM next Tuesday. This can make it much faster to enter in your tasks, especially on mobile.

Command Palettes

These are interesting and useful interaction and navigation tools that take a variety of forms and are becoming quite popular lately. Generally they are triggered by a hotkey or easily available button, which pops up a simple text dialog into which you can type what you want to do, and you’ll get a list of matching commands. These may be contextual based on where in the interface you are when you trigger it, and they can have other sophisticated functions as well. But in general they all aim to give you a single point of interaction to quickly perform a variety of common (or not so common) functions. They often implement NLP as above as well.

Dark Mode

While “dark mode” is a design aspect, it has a highly functional role for many people, so it’s important to consider separately if you are one of those who prefer to have the option.

Integration and Interoperability

For some people, connecting their task manager to other apps they already use or want to use is critical. For others it’s not something they care about at all. But this can be a huge differentiator and ought to help you narrow things down if you can determine one way or the other. Do you want your task manager to connect to your calendar, your Apple ecosystem, your smart speaker?

Integrations With What?

For those with a strong existing app or device ecosystem, this can be one of the most significant factors: does it work with what I already use and own? This is highly personal, and sometimes it can even be difficult to realize whether such an integration would even exist or be possible before you’ve seen it on a feature list somewhere. But yes, your smart speaker can (sometimes) connect to your task manager (e.g. “Hey Google, set a reminder for 9AM tomorrow”), your note-taking app as well, along with your email, and much more.

Perhaps start with a list of the tools and devices you already own, then imagine whether it would be nice to have some aspect of your task manager connected to them, either for sharing data (e.g. calendar integration) or functionality (e.g. create task from your smart speaker).

Integrated How?

This is a consideration with two different meanings, and they can often overlap or be otherwise related.

First, what forms does the integration take, what features does it have? In other words what aspects of each integrated system are actually related and connected? What can you do using the integration?

Second, you can consider how integrations are supported from a technical or functional standpoint, e.g. are they “native” (developed by the creator of the tool), or from 3rd parties, are they built-in to the tool, or do they use Zapier or some other external integration platform. This may seem largely irrelevant to many people, or hard to understand the importance of, but it can definitely affect what you can do with the integration. So this consideration can actually inform the above “what form does it take, what can it do?” question.


One of the most important considerations in integration is whether the data connection is bi-directional, e.g. your tasks can show up on a 3rd party calendar app (like Google Calendar), but you can also make changes on the calendar that show up in your task manager. In most cases bi-directional integration or sync is ideal, though in some cases it’s not critical.


This is simple in concept, and hopefully simple to evaluate, but can be complex in implementation. Essentially, does the tool have formal options for involving multiple people in task/project management. Almost any tool could be used this way by e.g. sharing a login, but generally you want multiple users, to show who did what, who is responsible for a given task or project, who wrote a comment, etc.

Most of the time it’s pretty clear which tools accommodate this and which don’t.

Offline Capability

This is not important to everyone, but for those who do value it, it can be a huge consideration. Anyone with spotty local internet, or who travels frequently, among other reasons, may really value good offline support. This is most commonly possible with desktop and mobile apps, but some web apps also feature it.

Now we get into criteria that may be a little more difficult to evaluate and compare, but are nonetheless useful to consider.

Organization and Structure

This can take many forms, but one of the most common is how many “layers” of organization does the tool offer. In other words, do you just have “task”, and all tasks are represented as equal, at the same “level”? Or are there folders, Projects, Lists, or some other type of organizational scheme? Here’s a basic outline of some of the common organizational concepts in T/PM tools:

  • Workspace
    • Department/Project/Space
      • Folder
        • List Mainly ClickUp
          • Task
          • Sub-task
            • Check-list

Note: Some systems consider check-lists to be entirely separate at another level of hierarchy

Generally speaking, when well implemented, at least some of these levels will be clearly exposed and “expandable” in some kind of hierarchy view, often the classic “tree view” as exemplified in common file managers like Windows Explorer or Mac’s Finder tool.

Your basic task is to decide how many levels of – or options for – organizing you need. Do you want to have every task categorized in numerous hierarchical ways? This might be influenced by the sheer number of tasks you have to manage, or the amount of differentiation in the areas these tasks occur. If you have few tasks or you are mostly interested in managing tasks for yourself in your daily life, you might be OK with a more flat organizational system that divides tasks in just a few simple categories, or not at all.


A “workspace” is generally the highest-level container for a set of work (or task) information. It often includes many tasks, folders, views, etc. In other words it encapsulates all work related to a particular area.

Depending on the application, these may be handled differently, for example some tools let you view multiple workspaces at once in a single view. Others only have 1 workspace per account or email, or no concept of a workspace at all.

Often times workspaces are the easiest way to define permissions, i.e. whether a given user belongs to a particular workspace or not.

Department, Project, Space

Another common – though certainly not universal – type of organizing concept is that of a “department” or “project”, sometimes called a “space”. You can have multiple of these within a given “workspace”, and whether they’re called “project” or “department” is often simply determined by whether the tool is oriented toward work or more general purposes. Some tools even have both.

Folder and Folder Equivalents

Folders are perhaps the most common and familiar way of organizing things for most people. Many T/PM tools implement them, though they are often called different things, or they serve multiple functions. For example ClickUp has Folders, but it also has “Lists” which can exist inside of folders and are in some basic sense a form of folder-like organization. But Lists also have other properties that a folder may not.

Many tools also allow folders within folders, sometimes to a near unlimited degree. Other systems simply forget about trying to classify each level of organization and just call everything a “folder”.

Tags, Labels, etc.

Some tools allow you to use the now-familiar idea of tags to organize your tasks, projects, etc. In certain cases this is the only way of organizing, which can be highly flexible, but for some people is also limiting or otherwise too lacking in clear structure. Labels can work differently, but are often similar or identical to tags.

Other Organizational Functions

There are also tools like ToDoist that implement other functions for helping to organize, for example “dividers” which are basically visual, labeled dividers within a list of tasks (inside a Project). They do not “contain” tasks, they simply divide them visually within an overall list, so they are not visible outside of your view of that list of tasks.

Notes on Categorization

In many cases these names are simply for convenience, to differentiate different parts of the hierarchy. In some systems they have functional differences, but in others they are just different “levels” of what are essentially folders.

It’s also important to note that different tools often use varying terms to refer to similar types of features and functionality. Perhaps nowhere is this more evident than in organizational tools. Additionally, not all of these organizational options exist in each tool.

Finally, keep in mind that you don’t necessarily have to use each organizational function in the way it is named. You may want to use “Workspaces” to differentiate between different companies you work with as a private consultant, or you might simply have 1 workspace for your entire consulting business, and use “Departments” or “Spaces” or even “Projects” to differentiate them.

Scheduling and Planning Features

Although it is not absolutely critical to every task management tool, the availability and usability of features to set dates, times, and reminders for these can be a very important differentiator. Different tools approach these functions in various ways. I’ll touch on just a few major aspects here.

Repeating Tasks

This one is a deal-breaker for some people, and only supported by a sub-set of tools (though an increasing number). The specific implementation of repeating tasks can also have important differences, some of which can frankly be a little difficult to understand or use. If it’s important to you, it’s worth getting really clear about how the feature works in practice in any app candidate.

Calendar View and Interaction

This is one that I didn’t realize at first was that important to me, but became a critical differentiator for my personal task manager needs. What I wanted to be able to do was drag-and-drop tasks around on a calendar, and have those changes reflected also in list views, etc. For some people this is totally unnecessary or just occasionally useful, in which case perhaps a simple calendar integration will work. But for others the calendar may be the primary way they interact with or reference their task list for the day, week, etc. I found this particularly diverged between people who are trying to either plan ahead more than a week, or plan out any given day in a more structured way (see “time blocking” below).

Gantt or “Timeline”

These views are familiar especially to seasoned project managers, but as they are implemented into more and more tools, they are becoming potentially useful to a broader range of people. While they are arguably of most critical relevance to someone trying to balance workloads and overlapping projects, they can also help people understand how and why their lives may be busier than they want, and perhaps facilitate some adjustment in an intuitive way.

Time Blocking and Other Features

Time blocking is a way of organizing your time within a day that essentially sets aside “blocks” of time for particular activities or (most often) types of activities. If you’re consultant and blogger, you might focus on writing in the morning if you feel most creative then, followed by client work in the afternoon and billing after that. Perhaps you end by doing scheduling. These are not necessarily specific tasks you’re doing, each block might involve multiple tasks that you accomplish and get archived, but you plan to do the same type of work at the same time very day, for example.

This is just one way of approaching or structuring your time, and there are many others, e.g. Pomodoro method, Eating the Frog, etc. Some apps give you specific tools or modes to facilitate one or more of these ways of working. A good example is Amazing Marvin, which has a wide variety of “Strategies” that can be enabled (or disabled) to add specific functionality or modes of working.

Reminders and Notifications

Some would argue that a huge part of the purpose of a task manager is to “remind” us of things, but this can take many forms. For someone who keeps their task manager window open all the time, all day, and is at their computer all day as well, or someone who carries their phone everywhere and has a habit of checking it regularly, then “active” reminders (e.g. pop-ups, alarm tones, etc.) may not be strictly necessary. So some task managers only implement minimal “active” reminders, either because it seems unimportant to their users, or it simply hasn’t been implemented yet (the latter is true in the case of e.g. Fibery, as of the time of this writing).

Most of the time, though, you want at least some options for active reminders. And then it’s just a question of your preferences as to how that works. Maybe you want pop-ups on your phone, but not your computer. Or maybe you want pop-up notifications, but no sounds. Figure out what will best help you get things done and then look for apps with those options and features. Sometimes this can be an iterative process though, for example when I first started looking for a new task manager I thought I really wanted active mobile reminders for everything, but once I actually experienced using them, I found it to be not that helpful and now I just keep my task manager open all the time for reference, which the occasional active reminder only for specific things.

Task and Project Features

This is obviously a very broad category and can be at the heart of a T/PM tool’s functionality, but it is also one of the hardest to directly compare as implementations can vary so much between apps.

Note or Description

A note or description is generally in addition to the “Title” or name of the task. This seems like a pretty basic feature, and yet not every task manager allows you to make any additional note or provide a description for your task. Many people don’t need that, or may be content using a workaround, but it’s important to consider whether this is important to you.


Can you attach one or more files to a task, project, etc., and if so what are the limits on file size, type, quantity, etc? This is one I essentially never use myself, but can be important to some.


A useful, if not critical way of augmenting your task info, comments can be especially important in the context of multi-user, collaborative environments. But they can also be used in other, more personal ways. For example I use them to keep track of notes for each time I complete ongoing, repeating tasks, and they are better for this vs. the Description or Notes above because they generally include the date written, and each entry is separate.

Support for Specific Methodologies, Strategies, etc.

Some people have a specific project or task management system like Getting Things Done (GTD), Eisenhower Matrix, or OKR that they want their tool to support in some way. This may take the form of certain specific features or configuration options, or – more often – it may simply be a particular way of using and interacting with the tool that enables the desired workflow or process. It is a minority of tools that actually have formal implementations of specific systems and methods like GTD, but if you search for any given app along with the name of a method, you have a decent chance of finding any resources on implementing that system in the tool in question. This information can sometimes be found in official documentation, but is perhaps more often discussed in user communities and 3rd party guides, tutorials, etc.

Having said that, even if there are few or no existing resources on how to use a particular method in a particular tool, it doesn’t mean that they are inherently incompatible. Often times, due to the huge variety of different tools and methodologies, it’s simply that no one has published anything about that specific combination. So in some cases you have to determine yourself, but searching for existing resources can at least be a quick shortcut to finding out whether a given tool is well known or especially suited for particular methods. ToDoist and GTD are commonly associated, for example, and they have even published an official guide to implementation.

If you’re new to formalized productivity methods, they can often be as important as the tool you use, if not more so. But they are certainly outside the scope of this article. ToDoist has a decent overview of some common options to consider, but I encourage you to look at some newer methods as well like PARA, PPV, etc. This is just to get you started.

Other Features

There are many other things that various T/PM tools include in task or project “entities”, or in the application as a whole, to augment their functionality and utility. These additional functions are especially hard to compare cross-app because they tend not to be standardized. Examples might include “workflow”, e.g. what “state” is task in beyond done and not done (in ClickUp this could include “in progress”, “researching”, and even custom states), or the concept of an “Activity stream” which may show all the changes across all entities (or items) in the entire app or a given Workspace.

Development, Road Map, and Support

A tool’s ultimate utility in the long-term is only as good as its support and development, in my view. Whether it is something as simple as supporting a new version of your operating system, fixing bugs, or implementing new features, not to mention helping users with their problems and questions, clearly the actions of the product team play an important role in the benefit we get out of our tools.


Primarily this concerns both the pace and quality of development output, as expressed in bug resolution, feature releases, and other improvements. In the case of fairly mature tools you might see fewer major releases, but you still want to see ongoing improvements, ideally speaking. But issue resolution (i.e. bug fixing) may arguably be one of the most important things, and is not always easy to evaluate. Look for change logs, either posted on the company’s website, or perhaps in their user forums, in change notes on an app store entry, or even within the app’s “About” section or some other in-app change log equivalent. You can also look for user discussions that mention changes, improvements, and fixes. An app without changes for 6 months or more is a definite warning sign.

A more positive sign, generally speaking, is clear identification of who is on the development team, and better yet, strong interaction from one or more members. To some degree the holy grail of dev team interaction arises where one or more of the developers or other founders often interact directly with the public, either on Twitter, or other social media, in their official user forums or discussion groups, etc. Connor White Sullivan of Roam Research is a prime example of this. And this can be really great! Just don’t mistake it for true transparency (see Road Map below).


You obviously want to get good support when you need it. This can be hard to evaluate if, early on, you don’t have a lot of unanswered questions (and for simpler task managers this is often the case, in my experience). But where possible you can look through any public support outlets they do have, or see if any reviews have mentioned testing their support. This can also connect with Community below, as many apps’ best support actually comes from other users like you.

Road Map

It can be very helpful, especially to some people, to know where a tool is “going”, what plans the developers have to improve it, what they’ll be working on next, and perhaps in rough order. This is where a “road map” or similar outline of planned features and development work comes in. Even better can be if you can directly interact with, “vote” on, or otherwise help influence that road map. Only a subset of development teams are public about their plans, and it should not be considered absolutely critical, but it can definitely help establish confidence in the team’s vision and the potential longevity and continued relevance of the tool.

Team Size

This is one of the harder things to determine in many cases, and isn’t necessarily a strong indicator of anything. However in general a larger team will be able to provide better support to a given number of people. For this reason knowing the general popularity of the tool can also be helpful in considering this factor. But I don’t personally feel it should be a strong determining point. Ideally you can determine from their actual pace of development output and responsiveness of support whether their team is effective within the size of user base that they have. Then they just need to maintain that over time as they (hopefully) grow!

Features and Other Updates

In general I actually don’t think this should be a major factor, mainly because I advocate people looking for tools that already do what they want and need, rather than putting much stock in future plans. Hopefully there is at least one product already on the market that does what you want. You simply can’t put too much faith in future plans, no matter how good the developers. But it’s still something that is of interest and can be worth evaluating, especially in cases where an important feature is coming soon, being shown or tested in beta, etc.

The general pace of feature development and release can also be a helpful indicator of team, product, and overall company health. Just make sure there is a healthy balance of new features and bug fixes. Too much of a focus on new features can often result in a very feature-rich but buggy application that’s not actually pleasant to use.

The “Ecosystem”: Extensibility, Community, Documentation, and More

I lump all these things together under the heading of “ecosystem” to refer to all of the additional support structures that exist around an app/tool that help it succeed, provide value, have longevity, etc.


This is pretty straightforward, and the need for it varies quite a lot from person to person (and tool to tool). Some apps are just really simple, and some people just don’t care for documentation and would rather experiment to figure things out, or refer to the community for help and guidance.

Extensibility: Plugins, Templates, and More

Another interesting aspect to consider are the options for extending the tool or getting it setup more quickly for complex workflows. Both can be facilitated by the community, either through plugins and things like CSS and Javascript hacks, or with templates, or both. Notion is a good example of the latter, with a huge number of mostly community-generated templates, while Roam is a good example of the former, with a “hackable” architecture that has given rise to a wide range of user-created themes, Javascript extensions, etc. (some of which are remarkably sophisticated).

This does also connect back up with Integration and Interoperability in that some of these tools implement or consist of that functionality. But here I am more noting extensions of functionality that are less about integrating with other tools.


This again can be important or unimportant based on personal preference (as well as tool complexity). Being an active or passive part of a community can be enjoyable and instructive for many. And for those of you for which this is the case, obviously start by looking at what community aspects exist for the tool itself. Facebook groups, Discord or Slack chats, dedicated forums, etc. But also consider 3rd party sites, dedicated blogs, YouTube channels, etc. How much content can you find that is not from the app developer/publisher itself when you search for its name?

Even if you don’t care much about being part of the community, the existence of a strong one can also be valuable, both as an indicator of and support for the longevity and success of the tool. And that’s one of those otherwise unpredictable things that would ideally be a factor, but is hard to consider objectively (whether the tool will exist in, say, 1 year, 2 years, 5 years). The health and and activity of the community can often be a useful “proxy” to help determine potential longevity, i.e. revenue or motivation for the developers to continue.


Getting data in, getting data out.


If you are moving over from an existing tool this can be extremely important. If not, it mostly isn’t. In the former case, quite simply, does the new tool support direct import from or at least import of formats that the old tool exports to?


This is also generally less important to many people, but is worth considering for two reasons. First, in the age of everything-SaaS, although cloud infrastructure is generally reliable, many people understandably want to have a local backup of their data. Export options can allow for that, at least to some degree.

Second, if the sheer number of possible tools and their rapid advancement leaves you unsure of your choice of tool to switch to, it can be a comfort if it allows some kind of export to hopefully migrate to other options if needed. In general, however, unless the export is something very common like Markdown (and in that case it often will not preserve everything, e.g. task dates), then the likelihood it will be supported by any given other tool you might move to is relatively low. In which case you have to hope (or search specifically) for specific import support in whatever tool you move to next. Still it can be nice to have export as an option…

Wrapping Up

I only used this heading because I’m writing this on Christmas morning for some reason, and I like puns. You’re welcome. ????

Hopefully by now you’ve been able to determine which of these criteria are important to you, and perhaps how important they are in relation to each other. Obviously it’s a lot to consider! But focus on that high level to start and it should help point you in the right direction.

Additionally, although I did mention a few specific tools along the way, this is largely devoid of pointers to particular tools or even lists of tools. I’d love to add at least some good reference lists at some point, but lots of those do exist and can hopefully be found quickly with a quick web search. My intention here was to help you make sense of and navigate those lists, to avoid getting lost and frustrated by trying to navigate the vast and choppy sea of all the many app options out there. I hope I’ve done that to at least some degree.

I’d love to know what you think, if I missed something, or if further clarification/info is needed. So if you’d like to comment on this article, head on over to my new digital garden!

More photos and general update

Woah, hey, it’s been a while. Surprise! OK, not really. As is so often the case, a lot has changed. And as is also often the case, I come with promises to finish all the previous multi-part blog posts on here, soon I swear. At least the backup one, because I’m finally getting my whole data scene together. More on that soon.

On the subject of life in general, many things have changed in the past 3, 4, 5 months. Katy and I broke up (a mutual thing, but still sad and difficult), consequently I moved to a new place in the Mission (loving it!), and I finally (re)left my Bauman College job (eek, I have to set my own schedule now). Life is a bit unclear for me right now, but also full of possibility, so that’s a good thing. I’m working on setting a comfortable schedule for myself, balancing work and play, getting things done for Planetside while also enjoying my new neighborhood, doing more hiking than ever (took a great one to Mt. Tam recently), and trying to meet new people. Things are good, but not quite settled yet…

Before I go, I want to mention that I’m still slowly going through the road trip photos. It’s funny to me now to think that I expected to be able to edit and post these as we were on the road. Even if I’d had a working computer and Internet connection, I doubt I would have had the time or patience. Granted I’m learning a new tool (Lightroom), but I’ve also realized I can be super indecisive when picking between several similar photos. So culling down several hundred (or a thousand) to less 50-70 (a comfortable amount for a single gallery) can be tough. At any rate I’m doing it now, and it’s enjoyable to look back at these places and remember the experiences, already starting to fade only 6 months past.

I’ve posted a gallery for the next stop we made after Bryce Canyon which is the Grand Tetons in Wyoming. We had some rather poor weather while we were there (it rained most days), so I really want to go back and get more hiking and exploring in. But we still saw and did some great stuff. Here’s the gallery link, and the description I wrote for it:

We spent several cloudy, often rainy days at the Grand Tetons in Wyoming. Lots of challenges in exposing sky vs. ground, water, etc. Some HDR experimentation, and liberal use of Lightroom’s sweet-ass graduated filter. Speaking of which, this is the first full album I developed and culled entirely using Lightroom. So far I’m liking it, but I’m really just getting used to its workflow. Once I’m “in the groove” with it I think it’ll be a much better experience overall than Picasa. But I will miss the face recognition!

Writing that made me realize I ought to blog more about these experiences. My explorations may be of interest and/or use to others, especially those looking to transition from an amateur to pro tool (Picasa to Lightroom). I used to write about my techniques a bit on my photoblog (and I hope to one day again), but now that I’m not really using it, I realize I’ve stopped giving as much info. I’m not sure anyone was ever really super interested in the details, but hopefully they’re worthwhile.
Thanks for looking and reading! More to come…

Seriously people, back up your data!

I write today not – as I would want – with a long-overdue update on our road trip (now long over), but rather with a cautionary tale about data loss. Read and learn from my example! A road trip retrospective will follow later and I hope that will be much more entertaining. This post is going to be a bit long, but please read it all, my experiences are an important lesson.

So why am I talking about data loss today? Well, surprisingly it has nothing to do with my laptop’s unexpected death in the middle of our road trip. In fact, this road trip seems to have ended up something of a lighting rod for technology issues (fortunately none involving the car!). After my laptop died, I of course continued taking photos, loading them on the external hard drive I had brought, using Katy’s still very much working laptop (thankfully we both brought one). So even though I was mostly out of communication, things continued along just fine. It was when I got back that real trouble began.

Naturally one of the first things I did upon my return was to load all my photos from the trip (about 10,000) onto my home data storage system. I had been using a Lacie 4big Quadra for primary mass data storage (10’s of 1000’s of photos, documents, projects, work files, and much more) for the past year or so, which has a total of 2.7TB of formatted space when using RAID5. I had about 1.5TB of data on it after loading my photos.

Now, I felt pretty secure with the data on the 4big given it was RAID5. For those not familiar with the technology, it basically uses multiple disks with a sophisticated data distribution system that allows for redundancy. This means that theoretically an entire disk can fail and your data is still ok because it can be rebuilt from the other disks. If 2 disks fail simultaneously (or the controller fails), then you have a problem. Theoretically however the chance of a double disk failure is lower than that of a single failure, so one would imagine the data is safer than with a single drive.

Unfortunately double disk failure or single disk failure combined with other corruption can and does happen, as I found out much to my dismay. I loaded all my photos onto the unit shortly after my return and began sorting through them and posting new sets every day or two. After a week or so of working on photos off and on, I started to see some issues reading certain images. I checked my Windows event log and found a whole bunch of disk-related errors essentially saying my 4big drive was corrupted and it needed to be scanned for errors. I rebooted shortly after and a disk scan ran automatically. Though I’ve never had much faith in Windows’ chkdsk utility, I soon found out that it’s even worse to run it on a RAID.

Chkdsk ran, finding a lot of errors, and “correcting” most of them. When I got back in to Windows, I found some missing images (by examining the disk scanning log I was able to see what files it had found “orphaned” or otherwise identified as corrupted and attempted to fix). Fortunately the files lost were fairly minimal, and things seemed to be working ok. That didn’t last long though. Within hours my 4big unit became unreadable. Windows still recognized it but it no longer showed the drive as being formatted and no data was accessible. I shut down the computer and the 4big unit and rebooted. The 4big began showing a series of varying configurations of warning and error lights. Eventually it just showed a total failure, meaning at least 2 disks has failed. I was shocked, but not yet panicked. I’ve seen odd – but correctable – issues like this before (not with this particular unit).

I contacted Lacie technical support, beginning an odyssey of 2 weeks of back and forth during which I received very little useful advice beyond resorting to extremely expensive data recovery options. The first tech I got essentially told me that the indicator lights on the unit didn’t necessarily indicate anything useful and that the only way to determine if it was an actual drive failure vs. say a controller failure would be to reinitialize the unit. This meant losing all the data for certain, so it really was not an option. One option I would have liked them to offer would be to ship an identical unit without the drives so I could switch my unit’s drives into it and test there. If it still failed, it would indicate it was a drive issue rather than controller or other hardware problem. But they weren’t willing to do that or provide any other remedy besides shipping the drive to them in Oregon for data recovery at a cost of thousands of dollars.

At this point I was fairly resigned to having to do data recovery, but still hoped for some cheaper alternatives. I didn’t relish the idea of shipping the unit hundreds of miles up to Oregon so I started looking into local data recovery options. I looked around on Yelp and did other general searches online. The world of professional data recovery is rather mysterious and almost universally very expensive. Your average computer shop can sometimes handle very basic recovery, but I can do the same things they can at home, so that wasn’t an option.

After a bit of research I came up with a list of local options and started calling to get an idea of rates, turnaround time, etc. The first company I called, Hard Drive 911 Data Recovery, was actually extremely helpful and although I didn’t end up going with them, I would still recommend them if only on the basis of their extremely informative and frank reps. The fellow I spoke to told me in plain terms the cost of recovery (minimum $1000 for a RAID 5 with 4 drives, up to $9000!) and the up-front inspection fee (others offer free inspection, 911 credits the inspection fee toward a recovery if you decide to go ahead). Their costs did not end up being particularly more expensive than many other options (this is a shockingly expensive service overall, no matter where you go), but their rep was far more helpful. We had a very candid discussion about the costs and value of professional data recovery and he made clear that they want their customers to feel like the service is worth the cost. He gave me a lot of information and links to resources online to attempt my own recovery, and advised me to get back to them should I want to pursue professional recovery options.

I spent the next 2 weeks attempting recovery myself. My very first task was to image all 4 1TB disks. This takes a very long time to do in pure RAW mode, 1:1 copying (all 1TB of data), so that took up several days in itself. Once I had the RAW images I could attempt recovery on them, rather than further risking the originals, which I wanted to preserve for others to work on should that become necessary. Note that the simple process of attempting to create images on my basic home setup through regular SATA could have caused further damage to the disks, so there was some risk inherent in what I was doing. However I didn’t hear any unusual noises from the drives and didn’t suspect physical damage, so I felt it was safe to do.

Over the next weeks I tried a number of software tools to recover the data. The biggest challenge turned out to be figuring out the RAID parameters so that the data could be actually be accessed properly. Because RAID distributes data across all the disks, including “parity” (redundancy) information, it can’t be read like a normal disk; you need to use special RAID emulation approaches in software, and you need the correct RAID parameters. I didn’t have these, and Lacie was extremely reluctant to provide this information to me, which was another frustration I feel was unnecessary. I eventually escalated my support request to a senior staff member who did provide this information, but it ultimately did not help.

In the end I was unable to recover any meaningful data myself. I feel like I was pretty close, I got to the point of being able to list a lot of files and actually see meaningful file names, etc. But the actual data contents wasn’t correct, and I suspect I either didn’t have enough information on the RAID parameters, or (perhaps more likely) there was corruption in the RAID data model itself. It was time to think seriously about professional data recovery again.

By this time it was almost a month since the failure had occurred. The vast majority of my important data, including 5+ years of photos, 10+ years of documents and project files, and much more was unavailable during this time. I didn’t realize it until several weeks in, but it was really affecting my happiness and overall mood, but at a fairly subconscious level. This is not surprising, but as I said I didn’t even realize it until after several weeks. I knew I had to get the data back, and that professional data recovery was likely the only option.

Lacie operates their own in-house recovery service called D2; in fact Lacie support initially indicated I was required to use them in order to maintain my warranty (I later found out there were several other authorized providers). I actually had a great back-and-forth with Patrick, the manager there, in which we discussed the recovery options and costs. Since it’s an in-house service, they can also perform warranty service, and their costs were lower than most local options. They also offer free 2-way shipping and free evaluation. The service sounded pretty good. But something in me balked at the idea of giving the same company potentially thousands more of my dollars just to fix a piece of hardware that I felt shouldn’t have failed in the way it did anyway (not to mention my relatively negative experience with their tech support earlier). I initially asked to proceed but, after not receiving a response for a few days (they did eventually send me a shipping label), I decided to try an evaluation with a local company first.

I had done price comparison and reputation research on a number of local companies. One of the more well-known companies is DriveSavers in Novato. I had initially steered clear of them, partly on the basis of some negative Yelp reviews. Eventually I did call them and ended up having a very nice conversation with one of their reps. We even discussed the Yelp reviews, and having been on the other end of some negative Yelp reviews for businesses I work with, I sympathized with where she was coming from. They were local, in Novato, I could drop off the drive on my way to or from work in Penngrove, and they could do a free analysis within a couple days. So it seemed like a worthwhile option. Their pricing was also comparable with other local options, and their high-end ($4410) was lower than several other local options, so in the worst case scenario I’d pay less than with the same problem at another vendor. The high end of the range usually corresponds with significant *physical* damage and at this point I didn’t think that was the case; after all I felt pretty close to recovery with my own simple tools. With the slow response from D2, I decided to go ahead with it.

I dropped the drive off and waited… A few days later I got a call back and they said they estimated they could recover 90% of the data and the cost would be between $3900 and $4400, the maximum they said it could cost before they even looked at the unit. At this point I was tempted just to get the drive back as I was fairly sure the level of corruption didn’t justify the cost. I called DriveSavers to talk to the tech working on my recovery, asked him a few questions, and felt his answers were rather condescending and uninformative.

He said there was physical damage on one of the drives, which I had also encountered when I imaged the drives originally. 9 sectors to be precise, which is not much on a 1TB drive. I told him I had some images that were made prior and offered to bring them by if it would help, but he brushed that off as if it was ridiculous that my images taken earlier might be of use. Maybe he’s right, but his reaction was not particularly nice. Then I asked him why, if it was just 1 drive with physical corruption, it was going to cost so much (and theoretically be so difficult) to recover the data; after all, isn’t RAID5 *meant* to recover from a single drive failure? He barely answered the question, saying only that there was other unspecified corruption, possibly due to chkdsk, and that it was necessary to do advanced recovery.

Thinking back to the Yelp reviews, I recalled some indications there of dubious information from DriveSavers tech support as well. Tales of “motor failure” and “intermittent hardware failure” sounded similar to the lines I was getting. In several of the Yelp reviews people even got their drives back and found other, cheaper ways to recover, discovering that the problem indeed was not as dire or complex as they indicate (for example a simple power supply replacement). That being said I felt by this time that I’d exhausted most of my own simpler diagnoses and recovery options, so even though I didn’t trust what I had been told, I wasn’t really clear there were many other options.

Then I called Patrick at D2 to see if he felt he could do better on the recovery if I sent it up to him; after all at this point I was still within the free eval at DriveSavers. He felt – and I tended to agree, though reluctantly – that if DriveSavers already have the drives and had them dismantled in their labs, that having them reassemble and box up so I could ship to D2 would incur further risk and I might not get the data back (or not recover as much).

This is where the mystery of the data recovery industry plays into their hands, theoretically justifying the high costs. After all, they’re the experts, they can tell you whatever they want, and who are you to argue? The uncertainty customers feel, and the fear of losing data, can justify almost anything in that moment. The lack of information and transparency, the difficulty in trusting these companies, is the biggest problem I have with the whole industry, to this day. I still felt like they weren’t telling me the whole truth, but I didn’t have any real facts to back that up, just my own experiences with drive failure in my time in IT. So ultimately I said yes, and the final bill was indeed $4410. I paid $4400 to get my data back. And you know what? It was worth it. Fully worth it.

But I don’t trust DriveSavers, I don’t trust D2 (who never gave me an actual maximum figure, they just said “I’ve never seen a recovery cost more than $2500”, which is no kind of commitment), and I don’t trust anyone else in this industry either, except maybe that guy I talked to at Hard Drive 911, who told me quite clearly that it was reasonable for me to try my own recovery first (once he confirmed I was aware of the risks).

The fact is I just don’t know. It’s possible that my drives were so damaged that it justified the cost. It sure didn’t seem like it from any actual evidence I ever saw. And the reaction of the DriveSavers tech was not particularly confidence inspiring. It seemed like he was more interested in stifling questions than clearly informing me about the complexity – and thus justifiably high cost of – the recovery.

So I don’t trust any of them, but I used their services because the alternative wasn’t worth it to me. Even if they’re full of crap and the recovery difficulty did not justify the cost (which I’m fairly certain of), it was still worth the price to me, and that’s what matters. What matters more, though, is that I am going to do my best to never have to pay for something like this again.

As to whether I’d recommend DriveSavers or anyone else? Sure, if you have a really serious data loss scenario and the data is worth $1000s of dollars to you, by all means, do it. Not because it may be strictly necessary, but because the risks outweigh the potential cost savings. Just resign yourself to paying the maximum possible quoted amount. If you’re ok with that, then it’s the right way to go, no questions. DriveSavers is essentially going to treat each recovery like it’s the worst possible case, from the get-go, and in some sense they may not be wrong to do that. Sometimes you don’t get a 2nd chance, and if they power up a drive and it fries itself before they even get a chance to do anything, they’d have been better off disassembling it from the beginning and running it in a clean room environment. Just be aware that this is going to be their approach and don’t be fooled by the low-end of their cost scale; you will almost never pay that.

So on the other hand if your data is only worth a few hundred dollars, or nothing at all, then try to do it yourself, or take it to a local computer shop or trusted IT consultant and see what they can do. It’s all about how much the data is really worth to you. If you have a medical problem that could be life threatening and it will only be determined in surgery whether that is in fact the case, you don’t go to the bargain clinic to get opened up, you go straight to the best, because the risks outweigh the potential savings, plain and simple. I don’t like this reality, but it’s a simple truth, and it’s what props up an industry of chronically bloated fees. I’m now a registered DriveSavers reseller so theoretically I have some investment in getting them more clients, but I will not be recommending them lightly. I may ultimately refer some people their way if I feel it’s justified. But to tell you the truth I’d much rather spend my time and energy teaching people how to back up their data properly!

As this post is now very long, I’m going to continue in Part II: Backing Up Your Data – Software Recommendations and Strategy.

Oh noes!

Ladies and gentlemen, the unthinkable has happened (well, not so unthinkable really): my laptop has died. Sadly this may mean no chance of further blog or photo posts until I return. Given my stellar record so far it may not be a huge loss but its rather a bummer as I was about to put up a bunch of Bryce and Zion pictures. But alas fate has intervened.

I will of course be tinkering with my laptop trying to fix it but so far it does not look good. I’m posting this from my new phone and while the typing experience is surprisingly good for a 4″ keyboard, there’s still no way this could work.

Fortunately our trip is otherwise going quite well, despite some annoyingly persistent rain (it really does seem to be following us around). We’re in Georgia now, heading down to New Orleans next.

So friends, wish me luck and email me if you want to keep in touch!

The 5 day week

It’s holiday time again, and this year both Christmas and New Years Day fall on a Friday, making for a nice 3 day weekend (or more, depending on where you work). But as we all know it’s not like this every year. Some years Christmas will be on a Tuesday, for example, and then you have to come back to work for 3 more days. It’s just not really in the Christmas spirit, right? Maybe that’s a bit of a stretch, but it’s a minor annoyance at the least that the day of Christmas changes every year.

This got me thinking about holidays in general though, and how they all fall on different days every year. Not to mention birthdays, anniversaries, trash days, and on and on. And then it came to me: What if our weeks evenly divided the days in our year? What if every day fell on the same date, year after year? What about… a 5 day week?

OK, big revelation, right? But’s the thing – we take a 7 day week for granted, but does it really make sense? And is this the only problem with our existing system? Maybe not…

I should note before continuing that this entire post is derived from an idle thought on the way home from work, and subsequent quick research. I am by no means an expert on any of this and I realize that quite a lot of debate and thinking has been done on this subject, well beyond my brief attentions. Still I found the lack of discussion of a 5 day week in particular to be rather surprising, so I thought I’d talk about it a bit.

First, the obvious question needs to be answered: Does it make sense to use weeks at all? Well, clearly it is useful to have a regular cycle of life, shorter than a year or a month, to help us organize the shorter time spans in our existence. So the idea of weeks makes sense, just as day, hour, minute, and second do. We need the ability to partition time into workable chunks.

The 24 hour day makes perfect sense too. It corresponds pretty much exactly to the day/night cycle on our planet. Likewise the 365 day yearly cycle, as it is very close to the time it takes us to complete one orbit of the Sun, and it completes a cycle of seasons, etc. that will repeat on that period. The use of hours, minutes, etc. has different origins, perhaps somewhat debatable in validity, but arguably much less obviously problematic and arbitrary than the 7 day week.

So what’s the problem with the 7 day week? There is of course the obvious issue that this post started with – 365 days is not evenly divisible by 7, and so the days of the week and what day holidays, etc. fall on changes from year to year. This is something we’re used to, so we are able to deal with it, but it’s pretty nonsensical and confusing if you think about it. Actually, holidays are not the only concern. I’ll admit to being a bit absent-minded, but there have been quite a few times I’ve been caught out by the changes to days and dates throughout the year, whether it be for remembering an anniversary, or going to a meeting on the right day. Translating days to date and back again could be simpler. And when you think about it, maybe 7 days is too long anyway, or at least when you think about the amount of working time in it. More on that in a future post.

So why 7 days specifically? Unsurprisingly there have been many different arrangements of “weeks” through the ages. According to Wikipedia, there have been weeks of between 4 and 20 days throughout history. The 7 day week, like many things, was probably popularized by religious effort, and as a source of irritation for me that fact starts to make a whole lot of sense. It’s based on many older week concepts, derived most likely from observable astronomy at the time these things were being worked out, specifically that there were 7 planets (perpetually moving objects) visible in the night sky. This 7 day focus of other ancient societies most likely informed the timeline for god’s creation of the world, and the eventual wide spread of Christianity drove the further adoption of this system. Why visible planets are a good basis for a calendar I’m not sure, but there it is.

The debate over calendars rages quite strongly, and there are many alternative proposals. What’s interesting is that few of them consider different week constructions; most focus on the lunar cycle, changing the number of days in a month, etc. In fact many are unnecessarily convoluted, seemingly in service of preserving the 7 day week and little else. That’s understandable as any major calendar reform is going to have a lot of resistance, and adding to that the idea of changing our fundamental work week is even more radical and likely to fail. Still, if you’re going to reform, I say go whole hog!

Despite lesser recognition, a 5 day week actually makes a lot of sense. Most obviously, it is evenly divisible into 365, meaning that all dates would fall on the same day every year. No more needing to buy calendars every year (unless you want to), and no more guessing what day a date more than a few days in the future will fall on – it would be supremely easy math to figure it out. In fact a 5 day week is the only way to divide the 365 day year into a whole number of weeks!

Certainly there can be other arrangements of partial weeks, just as we have now, and it’s not terribly problematic, but wouldn’t it make so much more sense if every year were the same? There is also the possibility of having out-of-week periods to even out some other arrangement of days-of-the-week, for example counting holidays outside of the regular week schedule (e.g. a 7 day week, with the Christmas holiday in-between, not having a “day of the week” designation besides the name “Christmas”). These are called intercalary days. But this too is complicated and needlessly confusing.

The 5 day week is blindingly obvious. Other arrangements like the Hermetic Lunar Week or the French Republican Calendar are ludicrous in their complexity by comparison. In fact virtually every current and popular alternative proposal has at least one extra calendrical or intercalary day. Yet the 5 day week, with none of these issues, gets no attention, it has no advocates. I ask you, what is wrong with the world?!

Just imagine if we had weeks that evenly divided the number of days in the year. Not just holidays, but all days of the year would fall on the same day of the week. You could use simple division to work out a date weeks or even months into the future, and have the answer in a second, rather than needing to be a prodigy to work it out in your head. Buy less (or no) calendars, save $1000’s over your lifetime. Ok, I’m getting ridiculous now, but when you think about it, 5 days just makes more sense.

Maybe the 5 day week isn’t the end all, be all solution. There is still the fact that a year is not precisely 365 days (but rather more like 365.25), and other issues to contend with, necessitating various methods to handle them. Still as an arrangement of days and a way to structure our lives in the short-medium term, it makes a lot more sense than the current system. Next time, we’ll talk about working hours in the 5 day week…

And on that note, if you’ve made it this far through this silly post, I thank you for reading and wish you Happy Holidays! Join me next year when I plan to post more regularly, while continuing my tradition of epic verbosity and unbridled loquaciousness.