Spending Some Time with DEVONthink for Mac

As I’ve mentioned previously, there are emerging classes of note-taking applications, one of which are reference libraries. I’ve always had some sort of a reference library in my workflow, but I never quite figured out how to use it well. Part of the reason is I didn’t have a clear enough use case for it.

Since becoming self-employed and a content creator, the reason for having a solid reference library became ever clearer. I’m finding it important to store and find research for items I’m working on quickly and easily.

The major player in this reference app market is Evernote. As a former Evernote user who didn’t like the feature bloat and direction of the company, I jumped ship a few years back. Still a little skiddish, though, I started searching for alternatives.

There’s one other major reference library app I found: DEVONthink.

What is DEVONthink?

DEVONthink feels like a local Evernote on steroids. Not only does DEVONthink offer web clipping, note taking, and OCR of documents and images, but it also allows you to store and sync your data locally and securely.

DEVONthink offers an extremely generous 150 hour trial, which runs a little differently than other applications. 150 hours comes out to be about six full days, but DEVONthink counts the trial timer while you have the app open. This is especially convenient if you’re going to try it with some light use cases like myself.

A quick note before we dive in any further. I only tried out the Mac version of DEVONthink, as my mobile use cases for reference software are currently limited.

Impressions of DEVONthink


Upon installing and opening DEVONthink, I found myself thinking this is an interesting app. Interesting in multiple senses of the word.

The bootup process reminds me of applications in the early 2000’s with loading screens and the like. The interface definitely feels dated compared to other applications like OmniFocus and even stock apps like It’s clear this application isn’t meant to give you warm fuzzies by its design. Rather, DEVONthink is meant to do some serious heavy lifting for research.

Portability & OCR

Design aspects aside, I loaded my digital file cabinet up in DEVONthink first thing. A great benefit of DEVONthink is the ability to add local folders into a database without actually copying all the information. Doing so means files stay where they are in the file system. This makes porting data in and out of DEVONthink easy, especially if you need to keep files accessible by other apps.

Portability is a huge win for DEVONthink. The software keeps applications in their native file formats whether they are in a database or not. To extract a file, all you need to do is drag and drop it out of the app.

When I dropped my digital file cabinet in, DEVONthink immediately solved a problem for me. I had previously gotten behind on my scanning, filing, and shredding, so there were a numbner of documents I wasn’t sure if I had scanned yet. Instead of trying to manually sort this out by comparing PDFs and papers, I let DEVONthink’s duplication detection figure it out for me.

This is a pretty incredible part of the software. I clicked on the Duplicates folder in the database, and not only did DEVONthink find duplicate file names, but it also found duplicate content using the OCR software bundled with it.

PDF management is ridiculously easy, too. I accidentally scanned two documents into one using Scanbot on my phone. In DEVONthink, all I had to do to separate them is click and drag. This is how these things should work in 2018!

However, that doesn’t mean DEVONthink is without faults.


No doubt there’s a lot of power hidden in this software. For most people I wonder if it’s a little too powerful. For someone like me who needs a moderately useful reference library that’s only going to store web clippings, bookmarks, and miscellaneous items which don’t otherwise have a home, the massive structure of DEVONthink seemed too bulky to have to learn.

The DEVONthink manual was well written and informative regarding the features and capabilities of the software, but beyond the manual, it was difficult to find other options to learn more. DEVONtechnologies has forums on their site, but reading through a few topics, I didn’t get the sense the forums were all that friendly.

Additionally, while using DEVONthink, I felt I had to really think about the process of capturing information to the three small databases I had set up. Web clipping didn’t feel intuitive to understand what it was doing, and the inbox system, while a great idea, didn’t click with the way I normally process information. This is a little nit-picky, but I also didn’t like how newly clipped items were marked as unread until I manually marked them read.

Ultimately, I ended up ending my experiment with DEVONthink intending not to continue. While it’s extremely clear even by some of the discussions on the Community that DEVONthink is the right software for some people, it didn’t turn out to be the right software for me.

You may be wondering what I’m using instead of DEVONthink. Well, I never thought I would say this again, but I’ve started using Evernote.


Justin’s Favorite Podcasts in 2018

A few weeks ago, Guild member philalethes posted a list of his favorite podcasts. I thought it was a great idea, and since it’s the end of the year (and I apparently am loving yearly list summaries this year), I decided to write up my own list of favorite podcasts from 2018.

A quick note: podcast listening time is limited for me, so my subscriptions list in Overcast is highly curated to the shows I get the most value from. Everything you see on this list is a podcast that’s personally impacted me in some way within the last year.


Ah yes, Cortex. The dynamic duo of CGP Grey and Myke Hurley. What makes this podcast so interesting is just how different these two people are, and how those differences affect their discussions about productivity, business, and being creators.

I also find the way Grey processes through his work to be fascinating. I mean, watch his vlog about trying to stay on London time while in Vegas for a business trip. The man is not afraid to try some pretty drastic stuff to improve his life, which I highly regard him for.


Another venture, this time with Casey Liss alongside Myke Hurley. Analog(ue) caught my attention this year because Casey left his job almost exactly a month before I did for very similar reasons. In many ways has my journey into free agency paralleled Casey’s since then, and, frankly, it’s nice to know you’re not the only one going through it!

Manager Tools

Manager Tools is hands-down the best podcast to listen to if you’re in the work world and wanting to grow. Sure, the podcast is marketed toward managers and leaders inside organizations, but the insights Mike Auzenne and Mark Horstman provide into leadership, coaching, and even office politics are applicable to everyone who has a job anywhere.

My whole stint as a manager in the corporate world was based off the materials provided in this podcast. It made me a better leader, and I can almost guarantee it will do the same for you.


Most of the Guild is familiar with Joe Buhlig and Mike Schmitz’s foray into hosting the internet’s largest book club, so I won’t belabor the description here.

My favorite part about this podcast? Hearing Joe and Mike talk about how the books impact their lives in meaningful ways. Hearing each of them process through their thoughts and action items helps me do the same with my own reading and listening. I also learn a lot along the way, too.

Internet Friends

Drew Coffman and Jon Mitchell host this regular discussion on how technology and relationships integrate (or don’t). Jon has one of the most fascinating, forward-thinking perspectives on multiple areas of technology I’ve heard in a very long time.

I always find the conversation refreshing even though it’s not always light-hearted. It’s refreshing because the hosts take time to authentically reflect on how technology impacts people.


Startup and Shutdown Your Workday in OmniFocus

Have you ever noticed when you sit down to work that it’s hard to actually start work right away? Or have you found when you are done at the end of the day part of your brain is still thinking about work?

Our minds need space to transition, but often we neglect to give ourselves the needed time to do so. Or, if we do make space for transition, we do it by consuming media or something else less valuable.

If any of this resonates with you, a specific process bookending your workday called a startup and shutdown routine may be helpful to you.

Having run a startup and shutdown routine for the last few years, I’ve found a few major benefits for me:

  1. My day begins with more intention. — There’s nothing like starting your day with an email inbox overflowing with a never-ending stream of “stuff” to do from other people. Having a plan for my day before I even touch email gives me a sense of control over how my day is going to go.
  2. I feel more focused. — Managing attention is one of the most valuable skills in today’s easily distractible world. Starting every workday the same way sets me in a direction that’s much easier to maintain throughout the day.
  3. I am more present. — On days I work, I only have a few precious hours of time with my family before my kids go to bed. I do not want to waste that time focused on unfinished, unaccounted for, and unneeded thoughts about my workday. Shutting down my day increases my ability to be mentally and emotionally present when it counts most.

In this article, I’m going to show you how I have startup/shutdown routines implemented in OmniFocus, but these are easily implemented in any task management solution. But before we do that, let’s dive into the specifics of what startup and shutdown routines are.

What is a Startup/Shutdown Routine?

Startup and shutdown routines are an idea I took from Getting Results the Agile Way, a productivity framework devised by J.D. Meier.

The premise is to start and end your day in the same way every day to help your brain ramp up into and down out of the work you’re doing.

It’s the same principle as listening to the same song when you’re about to write or going to the same place to a specific kind of work. When you set a routine for a particular task, your brain encounters less friction starting the task because you’ve trained it to expect what comes next after the routine.

Startup Routine

Startup routines can vary from lengthy pre-flight checklists to make sure all items are in order for the day down to a simple practice of picking your three most important tasks or outcomes.

My startup routine is a bit more complex, focusing on clearing the decks, planning the day, and focusing my attention on the work to come next. Let’s take a look.

The startup routine project in OmniFocus is a parallel project set to repeat every 1 day (defer until next date).

I start by reviewing Streaks for any habits I need to complete before my workday.

Next, I run a Siri Shortcut on my phone which asks a few questions about how I’m feeling for the day. The shortcut then creates OmniFocus tasks to remind me to act on what I need. This is an important step as my schedule is fairly variable. I can’t set a solid weekly routine so this shortcut helps me remember to check in with myself.

Next I plan my day. I run through a list of perspectives in OmniFocus and review the sprint board in Jira for the web development work I do. With those items in mind, I create a daily schedule in my notebook using two hour blocks. I’ve found block scheduling is more effective for me than trying to hyperschedule every moment of the day.

After setting the plan, I review some forums I participate in for any tasks or posts to reply to.

The team I work with currently uses an agile development workflow, so the next couple of tasks are to write daily checkins for that team and for myself.

Lastly, I process all my inboxes and clear them to zero. I’m not always as diligent to complete this fully, but the process of getting to clear means I don’t have any nagging thoughts in my mind about emails or tasks that aren’t entered into the system yet.

Once I check off the last action, the project autocompletes and the next day’s routine project is automatically created.

From there, I start the work.

Shutdown Routine

Shutdown routines are very similar to startup routines, but the aim is to help wrap up your day in a consistent way every time. The habit of a shutdown routine should involve ways to ease your mind out of work so you can be present elsewhere the rest of your day.

My shutdown routine isn’t as complex as my startup routine. It primarily involves brain dumping everything I have and cleaning up.

I perform a mindsweep in a couple of different ways depending on how I’m feeling that day. Primarily, I’ll take my notebook and just start writing everything on my mind in a stream-of-consciousness format. I’ll then process this into tasks later in the routine.

Next, I run the checkin shortcut I mentioned previously to help me understand if anything about my needs has changed during the workday. Working from home and as a developer can be extremely draining, so keeping tabs on my state regularly is important.

The next two steps involve making sure my time tracking is completed fully. I track all of my work time in Toggl using a combination of projects and tags, so I make sure none of that metadata is missing. From there, I enter any time toward development work into Jira I haven’t already entered.

Next, I process all of my inboxes just like in the morning.

Ideally, I like to write out a high level idea of what I want my day tomorrow to look like (if I’m working that day). These plans almost always change, but having an idea in my head gives me an aim to attain vs. trying to figure it out on the fly.

Finally, I work best when my work area is semi-clean, so I spend a few moments to close out any applications and clear my desk of any clutter that’s accumulated throughout the day.

Implement It For Yourself

If you choose to implement this process, start off small. Define 3-5 key tasks to both begin and end your workday. These can differ or be the same. Focus on the highest value tasks to start like planning or maintaining your system. Experiment for a week or two with those processes, then evaluate and add/remove as needed.

Startup and shutdown routines are an easy way to add some structure in your day even if the rest of your day looks like chaos. It has been the best way for me to help my mind ramp up into and down out of work.

If you choose to implement this, let me know how it works in the replies, and feel free to share your routines in the Community.


OmniFocus 3 Tags are Lists

Inspired by Scotty Jackson’s blog

There are some users who haven’t gotten their hand wrapped around the idea of tags in OmniFocus.

Scotty Jackson introduces the idea of using tags as a way to create lists for yourself.

If you can’t create a list from a tag that you created, maybe you don’t really need that tag.

Tags in a task manager becomes powerful when you’re able to create smart lists that you will be frequently using. A smart list could be called a saved search or custom perspective. Look for a task manager that has the ability to create a saved view that you can access easily.

What are your favorite tags and saved searches in your task manager?


Emerging Classes of Note-Taking Apps

If you’ve paid any attention to productivity news in the last 6-8 months, there has been a lot of talk around note-taking apps. Note-taking apps are part of the productivity trifecta (task managers, calendars, and notes), so this attention is no surprise.

And of course, with this attention usually comes a flurry of “What are the alternatives to X note-taking software” articles.

These articles usually lump software like Evernote, OneNote, Notion, DEVONthink, Apple Notes, Bear, and others all into the same list. While these apps all handle text well as note-takers, most have widely different feature sets.

There is a substantial break forming between different classes of apps in the note-taking space which I’d like to draw attention toward. If you’re in need of a note-taking app, this separation into multiple categories may help you make a decision based upon what you need.

Class #1: Note Takers

These are the apps we’re all used to seeing. At the very base, these apps take text, images, attachments, and put them into notes. The apps usually have straightforward organization systems (usually folders, tags, or some combination of both), and offer a similar experiences across platforms.

Apps that fall into this category include:

Class #2: Reference Libraries

This is the first sharp distinction I noticed in the note-taking space. Many tend to lump these apps in with the note takers, but the feature set of reference libraries often far exceeds what note takers can do.

Most often, reference libraries offer easy ways to clip data from external sources, search inside documents and images (usually via OCR), and organize documents in a highly detailed way. Reference apps also normally heavily rely on search and need to have a rock-solid sync system to handle the materials contained within.

Apps that fall into this category include:

You might be saying, “Wait, you added Evernote on this list too?” Well, yes.

While the free version of Evernote is as standard of a note taker as they come (really one of the first), the Premium subscription, which adds OCR and the ability to email in items for storage among other features, fits nicely into the reference app category.

Class #3: Wiki/Documentation

One of the newest categories of note-taking app are wiki or documentation apps. These apps are database-like and can be used for personal information storage or collaboration among team members.

These aren’t solely note takers because the experience tends to be more like creating a web page with information. T

hey aren’t reference libraries either because the apps often don’t feature the ability to easily get documents or web clippings in the software (though they may tie into software like Google Drive or Dropbox).

Apps that fall into this category include:

Class #4: Paper Replicators

With the rise of the iPad Pro, this category is one many look to if they want to move to a completely paperless lifestyle. The number one differentiator in this group: a heavy reliance on Apple Pencil for input and a free-form layout.

Apps that fall into this category include:

Notes are Notes

I think as these categories begin to mature, we’ll see fewer applications trying to be all-in-one. Evernote has done decently at trying to be al things to all people (with OneNote being the most successful), but most people don’t need an everything notes app . They want an appropriate place to store the stuff they need to keep track of.

I recently made the distinction in my life that I need a note taker AND a reference library. The two serve definitively distinct purposes in my system, yet I was trying to cram both functions in either Bear or Apple Notes. While they can serve as reference libraries, that’s not the role they best serve.

If you can get one software to work for you, that’s great. However, I say do not be afraid to use multiple apps for different purposes .

When you’re looking to choose a note-taking application, here are some questions you can ask yourself to get to those honest answers?

  • Do I want everything in one place, or am I okay with keeping different types of information in different apps?
  • Am I needing a place to store documents and search inside the contents?
  • Do I gravitate toward handwriting and like the idea of a paperless notebook?
  • Is something highly visual with building blocks work with my brain better than a sheets or cards metaphor? (If yes, something like Notion may be a good fit).

While these questions don’t get into the depths of individual features you may need from a note-taking application, these will at least help you figure out what classes of apps to focus your research on.

One last thing — be brave and commit to something when you find something that works! Remember: the most important thing is to get the work done.


Article – Reimagining an App from the Ground Up: Behind the Scenes of Todoist’s Redesign

I’ve never used Todoist but have always been curious about it. I just saw this article about Todoist getting a reimagining

What are some of the things that irks you about Todoist? I think I’ve heard the lack of a start/defer date was something that a lot of OmniFocus users wished that Todoist had.

The karma feature sounds like an interesting way to game-ify your productivity.

I found this statement interesting: "These were already the first steps on this bigger redesign project — internally, we call it Todoist Foundations (TDF) — allowing Todoist to better adapt to the user needs and workflows.

The next TDF project we’re working on is a revamped scheduler interface."

I love using OmniFocus plus Fantastical as a scheduler. This would be interesting for me to see in Todoist.

"During the first two months of Todoist Foundations, we also contacted some of our most active users, both premium and free, scheduling user interviews and sending out surveys. That feedback has given us a better idea of how people actually use Todoist, and what common problems they face. Lastly, we use analytic tools and (completely anonymous) usage data to understand which features are used most, and which are barely used at all"

It’s great to see a company actively interacting with their customer base. Of course, software development doesn’t happen instantly. Changes in user workflow must be studied for user ramifications and choices that may impact that user experience.

"We decided the PR bump we may get from a big release isn’t worth the bad experience for our team and our users. Now we work on steady updates that deliver new features and/or improvements every couple of months. This approach fits our six-week work cycles well, and makes it easier to get early feedback on changes and iterate — or even reconsider their value altogether. It also means our users never have to wait a long time to get new updates."

I’m all for a reiterative approach. Instead of the big upgrade that requires a new version number, just iterate, get feedback, and revise as needed. I like seeing a slow and steady approach to new features. Otherwise, the develops might want to hold back a feature that was finished months ago and wait for the big new version update.

I do like Todoist being available on all platforms and collaboration features. I am curious to see their approach to project/task management. I’m not familiar enough with Todoist. What are your thoughts about the Todoist platform? What did you like and what would you like to see in the Todoist ecosystem?


Task Notifications, Or Make Good Habits?

In this way, there are at least two important considerations when starting a journey of productivity.

Consider minimizing your reminders to the bare minimum.

Realize that the smoothest path into work is a deliberately chosen one.

In terms of the first point, consider going through your phone’s system preferences, and one by one turning off reminders, then turning them back on as desired or needed.

In terms of the second, to make a chosen path, the work must be approached by way of habit. The habit to start though is not to “just do everything”. It is instead to create a single list to which you can turn daily: a today list. A well-honed list creates a simple silo of play and work, a collapsed and streamlined set of ideas from the entirety of our environments.

If you have a list that stores your work and other desired habits of the day, then your single habit of “look at daily list” covers you.

Kourosh has great insight here. I liken this to a common life scenario: chores.

Imagine you’re a teenager. Your mom gives you a list of chores to do around the house. The dishes need washed, laundry folded, and dinner needs to be on the stove by 4pm so it is finished when your dad gets home.

Are you going to:

  1. Make your mom nag you until each of these tasks gets done, or
  2. Just get the work done?

While it may be easier to just let mom tell you what to do, of course she’ll be happiest if you just get the work done.

Looking to your task manager, do you need your task manager to be your mom nagging at you to get work done?

Probably not.

There are definite benefits to having due dates and alarms set on your tasks especially if a task must be done by a certain time (i.e. take the trash out on Thursday nights). However, over-dependence on them may signify a larger issue.

I’d contend if you have a bunch of alerts set up to remind you of all the work to get done throughout the day, you may expect too much out of yourself in a given day or you might not have taken responsibility for those tasks yourself.

It is much better to build a habit of trying to realistically assess what you can accomplish in a given day, week, or even month, make those tasks into a list, and then work off it. This is why people love paper for writing down their daily tasks, and why picking the three most important tasks for the day is so effective.

If you relate to the feeling of being alerted and dinged to death, I highly encourage you to take some time, evaluate what you can realistically do, and start smaller without all the bells and whistles.


Justin’s Favorite Productivity Apps — November 2018 Edition

In the last few months, my workflows and application choices have changed quite a bit as my needs as a business owner became more clear.

Without any further adieu, here are my favorite apps in my workflow as of November 2018.

Task Manager: OmniFocus

Oh the softwares you waffle on but ultimately need to come to grips with that this is the right one for you…

OmniFocus is exactly that in my workflow. Now that I’m 100% on a Mac for work, it’s much easier to justify going all in.

The killer feature for me? Recurring projects that complete and defer to another day based upon its completion. I utilize this feature so much with checklists and recurring projects that OmniFocus has ruined me for other task managers.

Note Taking: Apple Notes

If you read my topic on the Community about my note-taking app setup a while back, I had some convoluted ideas. Took no time at all actually using that system for me to realize it was a bad idea.

Now, all my notes are in Apple Notes. I don’t take all that many notes, to be honest, so Notes is a straightforward solution at this point. The benefit is my wife and I share some notes, so it makes things easy when we need to make changes to those as well.

Long-Form Writing: Ulysses

The two major contenders for long-form writing are Ulysses and Scrivener. I don’t do novel or long research writing, so Scrivener doesn’t make sense to me.

I love how Ulysses offers such flexibility in organizational capabilities. Groups, filters, and keywords make it dead simple to form whatever organization complexity I need.

Email: Apple Mail

I was trying out Mailmate earlier this year, and while I really enjoyed the software, I was finding I don’t really use many of the power features. I’ve used Airmail and Spark as well, but some of the quirks and bugs make it challenging for me to fully implement.

Thus, Apple Mail wins.

Planning: Paper

When I actually need to flesh out what I’m doing for the day or week, nothing beats paper. I remember things better when I write them on paper, so a benefit is I stay mentally focused better throughout the day.

My current favorite notebook? A Leuchtturm1917.

Idea Development: iThoughts

I recently jumped into the world of mind mapping. While it’s a bit overkill for smaller projects, using a mindmap to lay out the key areas of a project really helps me get my mind 😉 around it. I’ve found paper is good for dumping ideas out, but mind mapping helps me make sense of all of it.

Mindnode is an excellent contender in this space, even featuring OmniFocus integration. However, iThoughts is included in the SetApp subscription (which I’m a happy subscriber of), and while there are definite design differences between the two, iThoughts fits the bill nicely.

Web Development: Visual Studio Code

A nerdy entry on here, but an obligatory one considering my main form of work — web development. Code editors are plentiful these days, from Sublime Text to TextMate to Atom.

Surprisingly, my choice is Microsoft’s Visual Studio Code. The software is fast, clean, and offers quite a few tricks up its sleeve to make development work faster and easier.

Automation (Mac): Keyboard Maestro

If there’s an app that’s ever fallen into the “Where have you been all my life?” category, it’s Keyboard Maestro. In just a few short months of use, I’ve already developed a significant number of keyboard shortcuts to do even the tiniest of tasks I find frustrating, including showing/hiding specific windows (which is a pain when doing web development and you have 20 of them open…) or closing notifications without touching the mouse.

If you want to get as deep as you can into macOS automation, Keyboard Maestro is for you.

Automation (iOS): Siri Shortcuts

Let’s be honest, Siri Shortcuts is the star of the year for Apple. Forget new iPad Pros, an updated Mac mini, and all the other new gear. Siri Shortcuts is probably the biggest game-changing piece of software Apple has released in recent memory.

The system integration alone makes toying around with Siri Shortcuts infinitely more valuable, let alone the developer APIs.

While I’m not as heavy of an iOS user like others out there, Siri Shortcuts found its place on my iPhone XS as a quick way to trigger actions from my home screen.

Up In the Air

No system is perfect, and at this time, I have a few areas I’m trying to work out.


I’m currently using iCloud for most of my file storage and organization needs. It works, but Finder tags are not the most usable things in the world at any sense of scale (sorry Brett Terpstra).

This leaves me with two major viable options for reference and research: Evernote and DevonTHINK.

I’ve used Evernote in the past for this purpose, and it’s worked quite well; however, the lack of features the community asks for (for years) makes me hesitant to pay them a recurring subscription.

DevonTHINK is the option I haven’t tried all that well. I’m currently giving it a go as a productivity experiment and will report on the results of it in our monthly Pro newsletter. It may just be the option I’m looking for.


Oh email. I survey the landscape and it appears to be the land of 10,000 tradeoffs. My favorite iOS app, Dispatch, hasn’t had a meaningful update in years, and iOS Mail doesn’t cut the mustard with getting email into other systems easily.

Spark and Airmail are promising alternatives, but I haven’t connected with Spark’s design philosophy, and Airmail’s buggy nature makes me nervous. These are both great apps, but I haven’t been able to land on either long term.

Thus, I will probably stick with iOS Mail until an alternative comes out (can you say mashup of Dispatch and Airmail?).


I’m fairly satisfied with Apple Notes at this time with my low-volume note-taking. I do know, however, I’m going to hate the folder-only structure if I need to scale at all. This is why I’m holding onto Bear in my back pocket. It’s a solid app, supports Markdown (yay!), and is under constant development. I do lose the sharing support from Apple Notes, but in the long term, that may be a minor tradeoff. Changes may be coming, but not until they are necessary.


Why I Track Time

There is only one subject in the productivity space I’ve seen to be so highly contentious and subjective: time tracking.

If you’ve listened to Cortex (one of my favorite productivity/business podcasts), the topic has come up a number of times, with highly polarizing reactions from the audience.

I get it, too. Time tracking can be a pain. You have to remember to start and stop timers, look at the data, and then actually do something with it. All of that can be downright stressful.

Despite all the pain associated with it, I am a big proponent of time tracking.

When I worked in IT, I was required by my employer to track my time. It was an odd habit to get used to at first, but when you end up working multiple support tickets a day, each one requiring the time to be tracked, you get the motions ingrained in you. Starting a new task — start the timer — okay I’m moving on, remember to stop it.

Now that I’m self-employed, nobody is making me track my time, but I find a high value in having the data available.

Time Tracking Gives Perspective

Everyone gets to the point in life where they need to choose to stop doing something. Especially if projects or tasks are business related, these decisions can be difficult. Do I stop working on the side project I like, even though it’s not making me much money? Do I keep doing the thing that stresses me out, but brings in the most money?

There are many scenarios in life where having more data can help me make better decisions. Time tracking gives me yet another reference point.

Without having time tracking data, I’m limited to making decisions on my emotions or just how much money something makes me. Adding time into the equation gives more perspective.

For example, that project I really like doing but doesn’t make much money is only taking five hours a week. Having that data makes the justification to keep doing it easier. Or maybe I calculated an hourly wage of my main moneymaking project. Turns out it’s only making me $12.50/hr because I sink 60 hours into it a week.

While the data never makes the decision for you, having the extra data does help make the decision easier.

Time Tracking Shows Reality

Ever started working on something thinking you’d only spend 90 minutes on it, and once you completed the task three hours had passed?

People tend to be poor at guessing how much time a task will take them. Factor in distractions, and our sense of time can really get messed up throughout a block of working on a task.

Time tracking corrects that. The clock can’t lie. The numbers will tell you exactly how much time you edited that blog post or watched that documentary on YouTube.

I personally feel like I have a good sense of time, but when I get deep into a project, the hours slip away. I only have 24 hours in the day, and with having small kids at home, I need to be keenly aware of how much time I’m spending where. Time tracking enables me to do this more effectively.

Time Tracking Helps You Batch Tasks

Since I started time tracking for my business, the process of setting a timer and the awareness of it running has helped me be aware of how I’m batching tasks throughout the day. Instead of stopping a timer and having to start another frequently when switching tasks, I am more conscious of being able to group my tasks together.

Batching tasks has numerous advantages, number one of which is maintaining deeper focus for longer. On average it takes approximately 20 minutes to regain focus after switching contexts or getting interrupted. Do that multiple times per hour, and your effectiveness drops drastically.

While time tracking isn’t the magic bullet to begin batching tasks, the very process of thinking about what you’re going to do and starting a timer for it helps keep focus toward the front of your mind.

Time Tracking Allows Better Client Billing

Though this may not pertain to everyone who may be interested in tracking time, it is one major advantage and reason I track my time. If you ever bill a client for hourly work, TRACK THE TIME.

Not only does the tracked time give you the ability to bill more accurately, but you also have a record you can show the client if they ever challenge you.

I never work on a billable client project without having a timer running in the background — ever. I highly recommend you do the same, because it may just save your bacon down the road (and everyone likes bacon, right?).

Why Wouldn’t You Track Time?

While I highly value tracking time and recommend it as a general practice, especially for those involved in their own business, there may be reasons tracking time isn’t a good fit for you.

  1. You don’t have a good reason to. — This is the well, duh answer, but part of effectively tracking time is knowing what and why you need to track. You can’t sustain a time tracking habit without knowing your why.
  2. Time tracking stresses you out. — For some people, having a clock running in the background may cause undue stress. There are options that may help you track time without the stress of a timer, but you may want to evaluate if it’s right for you if the idea causes stress.
  3. You don’t consistently focus on one task. — If you jump between tasks frequently, tracking time may be extremely difficult for you. There are different types of jobs where this is likely the norm (i.e. most management roles), so evaluate if tracking time is worth the investment.


Overcome Perfectionism by Developing an Iterative Mindset

Have you ever felt like you can’t do something because you’re not good enough at it? Not finished a project because you weren’t sure if it was done?

If that’s you, you’re definitely not alone.

What we’re likely talking about here is the feeling of perfectionism. Perfectionism is, by definition:

the refusal to accept any standard short of perfection.

I know I want to think of myself as achieving perfection at times, but I always fall short of it. That’s the time when I get frustrated and often quit. It’s not healthy.

You might be thinking to yourself, “Well how in the world does anything good get made then if you don’t obsess over it and shoot for perfection?”

There’s nothing wrong with having an ideal in your head and aiming to achieve it. The world wouldn’t have most of the inventions and creations if we didn’t have individuals aiming for an ideal, a vision if you will.

However, there is a difference between perfectionism and excellence. While perfectionism says nothing but perfect is good enough, excellence says do the best you can with what you have.

Excellence, therefore, requires you to have a realistic viewpoint of yourself, the possible outcomes in front of you, and what you’re capable of in this moment in time.

That last one is the hard one. I know for myself that I like to skip the process and be amazing at something right away. But, as John Maxwell, one of the top authors on leadership said:

“Anything worth doing is worth doing poorly at first.”

Excellence rejects the notion poor means bad, and embraces the process of growth. In other words, the way to overcoming perfectionism is to embrace an iterative mindset.

What is an Iterative Mindset?

To iterate means to perform repeatedly. An iterative mindset is the viewpoint recognizing that repeating a task over and over slowly brings improvement over time.

Think of it this way: you can’t steer a parked car. Driving a vehicle requires movement, and movement is provided by the desire to go somewhere. What having an iterative mindset helps enable is for you to stop thinking about the end destination before you even leave the parking lot, and instead just drive, finding the way as you go.

Developing this mindset is a significant key to hitting your goals in life and developing your productivity systems. Here’s why:

  1. Goals require you to make progress at something you’re likely not great at. Let’s be honest. If you’re not pursuing something that’s not stretching your abilities, you’re probably not going anywhere all that meaningful. It’s safe to stay where you’re comfortable, but we all have areas in our lives where we need to grow. That’s the essential human experience. We never stop growing, but sometimes we need to push ourselves to grow more.
  2. Life is iterative. Just like the earth goes through different seasons at different times of the year, so does life. The systems, goals, and mindsets I have while working a corporate job won’t always apply when I’m self employed. Your systems will need to change to accommodate your life as it changes.
  3. Letting go of perfection and embracing an iterative mindset is less stressful, more fun, and more freeing. It’s easy to make progress when you’re embracing and enjoying the process. That doesn’t mean things won’t be tough, but it does mean you can take challenges in stride because you know how to make adjustments.

Building an Iterative Mindset

If you’re looking to break out of perfectionism and into an iterative mindset, here are three ways you can start today.

  1. Start right where you’re at . It doesn’t matter how good you’re at doing a thing. If you want to do it, embrace your lack of skill and just start doing it. You don’t hit the 10,000 hours needed to become an expert by watching Netflix.
  2. Recognize failures are learning opportunities. Any mistake that doesn’t kill you is an inflection point where you can choose to let it teach you or hurt you. It’s scary to look at your failures, but doing so will teach you more than any book, podcast, or blog post will.
  3. Try to improve one thing every day. Focus on finding an area you can improve by 1%, whether that’s by automating a repetitive task in your workflow, finding the lesson in a project, or doing one small helpful task like making your bed. The little things, including things that feel like they don’t matter, will add up to become massive improvements over the long term.

The truth is productivity systems are only tools you use to help get you to where you want to go. You can only adjust your systems so much to account for detrimental ways you think about your work.

Perfectionism is one of those detrimental thought patterns. As you learn to break out of the pursuit of perfection into the journey of excellence through iteration, I think you’ll find yourself hitting more goals, taking more opportunities, and finding joy in the processes of life.