637: Digging Deep on Tracking Time


Thanks for this episode. I, like Stephen, really only track time for work-related stuff. I use Timely because it tracks my activity on the Mac + PC, and location on iPhone. When I want to go back and figure out how to bill for stuff (which I acknowledge was not the focus of this episode), it’s super helpful.

I haven’t run into too many other people that use it, but I highly recommend it!


I used Wakatime to track all my Web usage and coding for my final year project at uni

This was a productive episode. So after setting up the basics with Timery / Toggl.

I have a Mac - iPhone and iPad.

If I start a timer on one device the other devices seem slow to sync the settings or not at all. (yes all on same account and wifi etc…)

Also I try starting stopping with Shortcuts as suggested and Siri will say “done” but other devices keep going…

Q: Sync: these Timery settings would be for all devices at once - Not per device right?

Is there a way to get all Timery devices to sync more consistently?

This show has me trying Timing again, which I tried for a couple months a few years back, but found I was being too precious with it and it was more of a time suck than anything.

When I set it up, I was asked whether I wanted to be prompted after finishing an online meeting, and I said yes. Now I want to turn that off (it prompts me every time I finish a call with my VOIP app) but I can’t find it anywhere in the settings. Any ideas?

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This episode just reminded me of the dreadful time accounting I had to do pre-retirement. Frankly, as an engineer employed by a company to design and develop products, this never made sense. As long as I “produced” how I divided up my day didn’t matter. And basically my most productive part of the day was the initial two hours because that’s how extra early I arrived so I could work un-molested! By the afternoon, I was basically finished for the day and could produce nothing. But because the bean counters just can’t see it that way, I (and actually every engineer) just produced a time report that would keep them happy. It just had to add up to 80 hours per two weeks. And it had to be turned in the day before the two weeks was up!

Now days I just occasionally glance at Screen Time


Very interesting episode.
I really like to time track my days, but I very often lack in starting or stopping the timers, so the data I receive is irelevant for me.
With the mentioned automation, it might start working for me.
But what I didn’t understand, if I use Timery (iOS/iPadOS) AND Timing(macOS), is there a way I can bring together the data from both apps into one summery, so I can get a whole picture, or will that not be possible, what would reduce the value of using both apps for me.


Sadly, I experienced all that you described in your post. In addition, despite professing happiness with my work, my boss and my boss’s boss repeatedly urged me to “log more hours” on my time sheet. I’m sure it was to make someone upstairs happier. :slightly_smiling_face:

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I listened to this episode yesterday but got a bit confused about how David was using Timing and Timery. Could someone provide a quick summary, please?

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One thing I heard during More MPU was David talking about Universal Control. He mentioned that you can’t have your iPad set as below your main screen; however, you can drag the iPad in the Display menu wherever you want after it has connected with your Mac. I have mine set as below my big screen. It is great!!

I don’t think this is possible, as there is no common language/format between them.

But you can use Timery on the Mac, which will solve the issue by putting everything into one system.

ps - welcome to the forum!

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I’d love to try time tracking, but my work is primarily on Windows and my personal life spread across Mac Mini, iPad and iphone.

I always forget to start and stop timers, so would need something automated.

Does anyone have anything they use cross platform that they would recommend?

THX for the welcome.
I would like to use Timing mostly because of the automatic tracking.
I’m also using LifeCycle on the iPhone which automatically tracks where I am.
Unfortunately I tend to forget to start the timer, and without that, it makes no sense at all, if I use only Timery.
Or do I miss something?

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That does make sense. Unfortunately for the automatic timing on Mac there is no equivalent compatible system on iOS – at least I think not.

I think David mentioned on the current episode of MPU, that they (or at least he) are thinking about an other episode to discuss the possibilities to automate Timery with Shortcuts or KM.
I very hope, they will do that, so maybe I can get something from there, to get over my lack of starting the timer, if I need one?

If I may throw my tuppence worth into the conversation, time tracking becomes really useful if you can compare how long you took for a task against how long you expected it to take. This is critical information for estimating how long you should allow the next time, which in a professional services context is vital if you’re to manage your time and business effectively. Clients, quite rightly, want to know how much a piece of work will cost before they contract with you to do it; if you can’t estimate correctly the risk of time overruns falls on your shoulders.

With regards to estimating, many years ago Joel Spolsky published an blog post on what he called evidence based scheduling, it wasn’t his original idea (I’ve traced the concept of Monte Carlo modelling back to a RAND report from for the DoD dating to the early 1960s), but it was a good implementation of a method that seems never to have been popularised in project/ task management system. It’s not that PM software (OmniPlan etc.) don’t implement Monte Carlo, but they mostly use triangular distributions (min/ most likely/ max estimates) rather than looking at the raw “accuracy of estimation” data that FogBugz (Spolsky’s software) used.

The statistics are easy and readily coded (I’ve used an R script in the past for it, about 15 lines only), but pulling the necessary “what I expected” vs “what it took” data together is a pain. I’d be really interested to hear if anyone with better automation skills than me has ever tried it for some combination of popular task manager (OmniPlan/ Things/ Todoist) and time tracker (Timings/ Timery).


I currently use Toggl. I have been unhappy with Toggl for years, but time tracking is the worst, so there is no system that makes you happy.

I’ve got a couple Alfred tools that make my life much easier. Primarily:

  • Alfred Toggl, which is used for interacting with the timers I’ve added throughout the day.
  • Alfred Time, which I find is the fastest way to start and stop Toggl timers while I’m on my Mac.

I’m a freelancer, and even though I don’t really bill hourly, I find the data from time tracking can be very useful for historical analysis and future project planning. I often consider switching to Harvest for their simple reporting feature that breaks down time spent on a project, and time remaining. I also really like Harpoon, but it does much more than time tracking. (It does a bunch of tax stuff too, but it’s not that Canada-aware and it manages your income in some ways I find confusing.)


I’ve used the Free version of Harvest (getharvest.com) for a while because I like their invoicing capabilities. Do any of these solutions have similar invoicing for freelance projects?

Harvest, Harpoon, Cushion, Freshbooks, and many others that I can no longer remember all offer invoicing. It’s table stakes, really.

Was more thinking about the services that were discussed in the most recent podcast - Timery, Timing, Toggl. Didn’t see any invoicing details from their sites - or integrations with 3rd party invocing apps - but I could well have missed it!

Square also has invoicing capabilities but I do not think they have the time tracking.