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.


Creating a Daily Review Checklist in Keyboard Maestro

The daily review is one of those tasks that I’ve never liked to do. The day is almost over and I’m tired. The last thing I want to do is to go through my shutdown process and run through my checklists so that I’m ready for tomorrow. I decided to use the automation tool, Keyboard Maestro, to speed up my end-of-the day review. I often skip steps to speed up the review process but I usually regret it the next day when I miss a critical time-sensitive issue.

The seed of this article started here:

Updating My OmniFocus Planning & Reviewing Workflow

As a recap, I end the day with a short review of the day. I check the following:

  1. Clear the OmniFocus Inbox and put new tasks into the proper project or checklist.
  2. Visit the Review perspective to review any projects that pop up here.
  3. Check my Menu, or list of available tasks, and flag tasks as a higher priority item.
  4. Check my Agenda perspective to create follow-up tasks based on any agenda items or talking points with other people.

I grouped a list of my end-of-day perspectives in OmniFocus. It is also sometimes called the shutdown ritual or the daily review. It worked because I arranged these perspectives together inside OmniFocus.

I explored using a spreadsheet or an OmniOutliner document to create a checklist using URL schemes to open an app:

Creating a Weekly Review Checklist with URL Schemes

With URL schemes, I couldn’t find a way to do multi-step processes such as opening Day One and automatically create a new journal entry with a series of questions about how my day went. That’s when I tried my hand using Keyboard Maestro to automate the process.

I wanted to create a virtual assistant that would guide me through my end-of-day review. URL schemes were a good start but I was limited to one action for each link. I could learn AppleScript and figure out how to get an app to perform multiple steps to work some Automator magic. Or I could figure out how to do it with my trusty app, Keyboard Maestro. I started experimenting with Keyboard Maestro and OmniFocus by grouping perspectives into checklist palettes:

Creating OmniFocus 3 for Mac Perspective Groups with Keyboard Maestro

I explored switching between different perspectives in OmniFocus. This time, I wanted to go beyond OmniFocus perspectives and start stringing together a series of actions into action groups.

This is what my new End-Of-Day review checklist looks like now:


I start with the top-left step (clear gMail Inbox) and work my way down the first column and then go down the second column. I’ll start by identifying my action groups.

Defining My Action Groups

The first thing I needed to do was to define the various action groups I wanted. I broke my action groups into three areas:

  1. Clearing the Inbox items into File Reference, Task Manager, or Trash
  2. Identify my task manager lists, views, or smart searches for the end-of-day review
  3. Preparing for Tomorrow

Clearing the Inbox items into File Reference, Task Manager, or Trash

I have a daily stream of tasks, projects, and responsibilities coming at me from all directions. I started to identify some Areas of Responsibilities where I get requests or inquiries:

  1. LinkedIn
  2. Facebook
  3. Facebook Pages Manager
  4. Email
  5. Discourse forums
  6. Slack channels
  7. WhatsApp groups
  8. Drafts
  9. Ulysses
  10. Evernote
  11. Bear
  12. Download folder
  13. Dropbox folder
  14. Physical in-tray
  15. My messenger bag
  16. My wallet

For brevity, I shortened my inbox list for this post. We have an endless list of inboxes that come into our daily lives.

Identify my task manager lists, views, or smart searches for the end-of-day review

I want to look at a list of views in my task manager and update the projects and tasks to reflect my current state of reality at the end of the day. To do that, I created a series of custom perspectives or smart search lists in your task manager to help with an end-of-day review. Here’s a sample of what I go through during my end-of-day review.

  1. Forecast calendar – Do I have an appointment in the near future that will require a new task?
  2. Agenda – Are there any waiting-for items or agenda items that will require a new task?
  3. Completed tasks – Do I need to create a followup task for a completed item?
  4. Big Rock projects – How are my Big Rock projects doing? Do I need to change a next action or flag an item to focus on?
  5. Menu – Review my list of currently available next actions. Do I need to delete, defer, or delegate? Do I need to flag a task to the Dashboard?
  6. Today view (Dashboard) – Review my due and flagged tasks. These are the tasks I want to work on tomorrow.

This group of views will change over time because our needs will change. Determine what you need to review and how you review them. Create the views that make sense to you.

Move all inbox items into the task manager, file reference, or trash bin

Now that I’ve identified all my inboxes, I need to start clearing them out. The final destination for all inbox items are:

  1. File reference – Put any useful notes, articles, or items of interest into a storage system for future use.
  2. Task manager – Many inbox items will require a followup action. I create tasks in my task manager for any actions required for incoming email, Slack conversations, or other incoming matters into the task manager.
  3. Trash bin – The perfect outbox for items that I won’t need to save. Junk emails, FYIs, advertisements, and outdated materials go here.

My end-of-the-day review tries to clear up the various inboxes. I don’t have to clear everything. If I have a huge backlog, I chip away at it and clear a handful of inbox items each day. I repeat the end-of-day review daily and eventually clear out my inboxes. Eventually, I’ll be able to catch up to my inbox and not worry about outdated inbox items that have expired. There’s nothing worse than inboxes full of stuff waiting for me to sort out.

Creating the Keyboard Maestro Macro Group Palette


The first series of macros in this group includes my various inbox items. In my screenshot, I have gMail, DevonThink, and Ulysses. Each macro opens up the app or a web site for me to review. Clear the inbox from each one. Move an inbox item into file reference, my task manager, or the trash bin. The last inbox should be my task manager’s inbox. Clear out the task manager inbox by moving an inbox item to a project or checklist.

  1. gMail
  2. DevonThink
  3. Ulysses
  4. OmniFocus

The next group of macros goes into my task manager checklists. After clearing out my inboxes, I go through my task manager. A task manager’s greatest strength is the ability to filter your projects and tasks into logical groups that makes it easier to manage. In my example, I go through the following:

  1. OmniFocus Review perspective
  2. OmniFocus Forecast perspective
  3. Agenda
  4. Completed
  5. Big Rocks
  6. Review Menu
  7. Review Dashboard

Add any further checklists that needs to be checked at the end of each day. Each perspective looks at certain parts of my projects lists. I could also have a perspective that looks at all Home project or all Work projects. The final list of smart lists is up to you.

The last action group closes out the day. After completing the task manager action group, I’ll finish the day and prepare for tomorrow.

  1. Plan Tomorrow – This is my personal preference of scheduling tomorrow. I’ll have a blog post about this very soon. TL;DR: I arrange OmniFocus to take up half of the screen and Fantastical occupying the other half. I drag and drop OmniFocus tasks to tomorrow’s schedule. If I don’t schedule a task, it usually won’t get done.
  2. Journaling – Compile my thoughts about the day. What did I do? How did I feel? Where there any victories today? Are there any activities that I could delete, delegate, defer, or automate?
  3. Organize my desk – Remind myself to clear off my desktop. Hide all windows except OmniFocus. This prepares my computer for tomorrow. When I return back to the office, my OmniFocus Today perspective (Dashboard) is the first thing I see. Now that I’ve described my end-of-day workflow, I’ll look at the different types of macros I use in Keyboard Maestro.

Three types of Keyboard Maestro Actions

Simple Notification


This notification can remind me of what I need to do when I click on a Keyboard Maestro action. This macro displays a notification for a physical action that I need to take. A list of physical actions includes:

  1. Clear my wallet
  2. Empty all notes from my briefcase into the in-tray
  3. Collect all items in my office and put it by my desk side for further processing.


Open a URL (Callback URL or web site)


I can open a web site and mimic some actions to get to a particular screen. This is helpful when there is no MacOS app available. Examples include:

  1. Open and perform a series of gMail actions
  2. Visit Asana and go to my Asana Inbox.

Callback URLs are a popular way of scripting. This is an alternative to AppleScripting. Many apps offer a way to copy a URL link that will take you to different sections of an app. In the next screenshot, I have a link to my DevonThink Global Inbox.


Open an app and mimic user interactions


Build a Keyboard Maestro macro to mimic a commonly used routine. In this Ulysses screenshot, I mimic launching Ulysses and opening the Ulysses inbox. Keyboard Maestro has the ability to “record” your actions and save it as a macro. This is a great way to learn Keyboard Maestro and see how it constructs the recorded steps.

You can also use a combination of Keyboard Maestro actions and AppleScript to create complicated macros. You can have two different apps work with each other with minimal programming experience.


Build your end-of-day workflow slowly

Start with a small group of macros using Keyboard Maestro’s floating palettes. Build it up over time. If you start off with a lot of workflow steps, you’ll be tempted to just skip it. In my personal experiment, I started off with my task manager workflow that were simple. They just switched between my different custom perspectives. After a couple of weeks tweaking my task manager workflows, I added my inbox processing workflow. I finally added the closing actions to my workflow. Take time to discover what works for you. Consolidate where you can.

A simple notification reminder


I added an action at the end of each macro that displays a notification message. It describes the step I am set working on. Here are some sample notification messages I included with my macros:


Customize each Display Text message to describe the result desired when you click on a new macro. This becomes your virtual assistant prompting you to continue on to the next step. I’ve discovered that I would just blindly go through the end-of-day review without understanding what each step was for. Every time I click on a macro, I read the quick prompt and remember what I needed to do. This simple, final action in each Keyboard Maestro macro gives me a sense that what I’m doing has meaning and I won’t start skipping steps trying to shorten the review time. Otherwise, I’ll never go through the end-of-day review.

Action Summary

  1. Define your inboxes workflow
  2. Define your task manager workflow
  3. Slowly build up your Keyboard Maestro group based on your inbox workflow and task manager workflow
  4. Create Display Text messages that describes each action

Now that I’ve finished my end-of-day macro group, I’m already thinking of creating a macro group for my weekly review. It will include review workflows that I don’t use daily. I’ll be adding some more processing such as:

  1. Purging projects, folders, and groups in DevonThink and Ulysses. The end-of-day review cleared out my inboxes. This time, I want to delete any outdated documents in Ulysses, DevonThink, and Drafts. I also want to delete e-mails that are no longer relevant.
  2. Review my mind map. Get guidance from my mind map about higher level goals and dreams. Update the mind map when projects have been completed or dropped.
  3. Visit to look for my next book to read.
  4. Check my weekly routines to see if I am up-to-date. Delete, delegate, or defer weekly routine tasks as needed.

I can create different Keyboard Maestro macro groups for different checklists. Reviewing is an essential part of a productivity workflow. The end-of-day review and weekly review are two of the most commonly used workflows. Using Keyboard Maestro can speed up this cumbersome process.

I’ve included a sample Keyboard Maestro macro file for download. Customize it to your workflow. Add your own Display Text messages. Share with us what you’ve created. I’d love to see what you come up with.


Download link for sample Keyboard Maestro Macro Group Palette

Download and unzip. Modify to fit your workflow.


Trying Things 3 for Two Weeks

I’ve been an on-and-off user of OmniFocus for the last half a decade or so. I got pretty excited at the release of OmniFocus 3’s iOS beta earlier this year. Omnigroup always does a great job with their software. However this time around, even after release, there are areas of OmniFocus 3 I felt needed some work.

I’m learning to experiment with my systems, so one night, I decided to embark upon an adventure — try Things 3 for two weeks.

Every task manager is different. If you’ve ever tried out two or three different apps, it’s easy to see each one has a unique focus, strengths, and weaknesses.

My goal in testing Things 3 was to find if it could really work for me, or if OmniFocus would still reign supreme.

How I Tested

There’s really only one way to truly test a task manager — go all in.

It’s true. The only way you’re ever going to figure out if productivity software will work for you is to throw everything you can in it to see where it breaks.

To get going, I downloaded the Mac trial and the iPhone app, set up a sync account, and started moving tasks over.

Importing items into Things 3 isn’t actually all that difficult. I set up some Areas, and I started copy/pasting tasks in from OmniFocus, setting tags, due dates, and the like as I went.

To be fair, I didn’t dive into automation, the iPad app, or much for keyboard shortcuts in my two weeks. These are strong features of the Things suite, but I’m not a heavy user of any of these anyway.

You might be asking, “Why only two weeks? It takes longer than two weeks to get used to something like a task manager.”

True, and fair point. I had two reasons:

  1. The Mac app trial and iOS App Store return period are two weeks
  2. Two weeks is a fair bit of time for the “new shiny” feeling of something to wear off and to get to the real meat of something.

With that being said, here’s what I found in my short venture into Things 3.

Things I Liked

Aesthetics. Things 3 has had its praises sung up and down for its world-class design. It’s true — this software is one of the best looking task managers out there. OmniFocus 3’s redesign is great, too, but it’s not quite as aesthetically pleasing as Things 3. What stands out about Things’ design is user experience did not take a back seat to visual design.

Whimsy. It’s rare to get a whimsical feeling from using an app these days. While Things takes notes from general design trends, it’s whimsical experience is what makes the app a truly enjoyable software to use. Its whimsy comes mostly from the little details — transitions, animations and how the app responds to user interactions. It’s hard to explain in words, but if you’ve used the app, you’ve likely noticed this.

Less-Pushy Due Dates. Nobody wants to wake up to 25 overdue tasks. Nobody. And let’s be honest — this is largely a process problem for most people by overusing due dates. However, if you do end up missing a task on its deadline date, wouldn’t it be nice if it just rolled to the next day instead of ending up in some different “overdue” screen? Things 3 does this, and it remove much of stress from missed tasks.

Rock Solid Sync. Sync is a core feature of any app these days. All I have to say about Things 3’s cloud sync is it just works. As a former Things 2 user, I am grateful to see this in action.

Floating Add Button. This is one of those whimsical design elements, but it deserves its own mention. The floating add button, which can be tapped to add a task in context or dragged to another part of the screen to add a task in place, is a genius addition. I never knew I wanted one until Things implemented it!

Rapid Development. It’s a bummer to see so many great apps (Editorial and Dispatch, for example) have ridiculously long release cycles, especially when OSes and other software are changing at a rapid pace. Cultured Code definitely keeps up with the changes, but also goes above and beyond with major feature releases every few months. I have to give total credit to the developer for this.

Things I Didn’t

No More Than One Level of Subtasks. I didn’t think this was going to be a big deal for me, but it turned out to be. In Things, you can have these items hierarchically:

  1. Area
  2. Project
  3. Task
  4. Checklist

Unless I was missing something, you can’t get any deeper than this.

As a person who sometimes has multi-step, nested processes templated out, this became a little overwhelming to deal with. In big projects, I rely heavily on the hierarchy folding features in OmniFocus. Not to have these was quite a challenge to overcome.

Not as Easy to Hide Tasks. In addition to having only a single level of subtasks, I found it harder to hide tasks. Start dates were helpful, but sometimes they also hid tasks too well for my liking. What I need out of a task manager is the ability to hide tasks until I need them, and then make it easy to see them when it’s time to start checking them off. For the way I think about tasks, Things 3 only got part of the way there.

No Perspectives or Saved Searches. This has been a frustration of many who are coming from other task managers who have a saved search type feature. I’m not the biggest perspectives user in OmniFocus, but even the ability to show tasks fitting multiple criteria without having to retype a search query would be a great addition to Things.

What Did I Choose?

I went back to OmniFocus 3.

Indeed, it’s never easy to change a big piece of your workflow, and OmniFocus has largely been the rock-solid center for a number of years.

Don’t get me wrong — Things 3 is a fantastic task manager. I’m partial to the design choices made by Cultured Code throughout the app. It’s just fun to use.

However, you have to stick with what works for you. Some of the things I didn’t like simply kept me from working as efficiently as I could in Things versus OmniFocus.

Despite not making a change from this experiment, I did learn a number of lessons from Things’ opinions toward task management I’m taking and now applying to my OmniFocus workflow.