Day One Goes Subscription

So Day One has become the next software application to adopt a subscription pricing model. This app developer has monkeyed around with its price/product offering for some time, and Day One has always been towards the expensive end of the curve for what could harshly be described as a glorified text editor. I guess it was inevitable they would ultimately end up converting to a subscription model in an effort to smooth revenue flow. Currently the developer is stating it will continue to support the current app and won’t force a move to the subscription version, but there is no doubt the first foot has fallen. At some point, I’m sure the other shoe will drop and it will be subscription or bust!

I’m not against subscription-based business models for software. I pay subscription fees for YNAB, Setapp, 1Password, Fastmail, Headspace, and maybe some others. I am willing to pay for software that I use and enjoy, and that satisfies my own price/value decision matrix.

Day One’s announced subscription seems expensive, especially when converted to Australian dollars. Expensive enough that rather than happily paying to carry on with an app I have used for more than 4 years, I am instead casting around for alternatives. The best and most immediate alternative I can see is to move my journaling to Ulysses. I’ve found a Workflow, ah, workflow that auto-populates date, time and location into a neat header box so the journal entry has a basic level of context. What I would lose from Day One is the pretty and additional metadata and the journaling-specific user interface. Photo import can be replicated, albeit perhaps not quite as seamlessly. The major problem with Ulysses is that it just doesn’t feel like a journaling app – at least not yet. Maybe I would get used to it in that context with time?

As mentioned, I’ve used Day One consistently for four years, and it has gained enough of a mental grip on me that I might miss it were I to migrate. Still, there is a limit to the number of subscriptions my budget can handle. When I have other, fully paid apps just waiting to be used, it becomes difficult to justify paying yet more money on an on-going basis.

I’m probably still on the fence right now, but Ulysses may be taking the lead…

The Weekly Plan

I consider the two fundamental resources in work planning to be:

  1. The calendar
  2. The to-do list

The calendar represents the hard landscape: events that are non-negotiable, time-based and require you to be doing a certain thing, at a certain time, at a certain place, possibly with another certain person. If it’s in the calendar, it’s a certainty. Calendar entries are commitments to yourself and possibly others.

The to-do list is used to track tasks needed to be done to move the ball forward. The list is potentially filled with a lot of items that may not necessarily be linked with one another. They are commitments to yourself, but they are not tied to being done at a particular time and don’t generally require the involvement of others. I use OmniFocus for managing my task list, but it really doesn’t matter what is used, as long as there is a trusted location to track everything to be done.

As a general rule, I’m not a fan of putting tasks onto calendars. I think they are two distinctly different things that should exist in their own dedicated spaces. However, like any good rule, there are times when this rule should be broken.

Leveraging multiple calendars

The beauty of using modern electronic calendar systems is they support multiple calendars. The classic and most obvious application of this is creating seperate work and home calendars. In addition to these staples, however, it can be helpful to create a weekly plan calendar.

Each calendar’s visibility can be toggled on and off, depending on the needs of the moment.

Using the weekly plan calendar can facilitate the addition of tasks onto a calendar view without gunking up your regular calendars that represent real physical events and commitments. This leads to the next step: time blocking and setting commitments for your future self.

Time blocking

The purpose of time blocking is to help establish a plan for a forthcoming period of time and build accountability for your time. The idea is to create work sessions that are linked directly to items on your task list. Transferring tasks to a calendar and applying estimated timeframes in the form of a timed calendar entry can help build a visual map of work to be done. Visualisation is a great tool to help identify whether your to-do list is realistically achievable in the time available. It can also help enforce urgency by indicating how potentially little time is available for meaningful work. Finally, it can be a reward system. If you get ahead of your schedule, you’ve earned yourself some relaxation time, safe in the knowledge that you aren’t falling behind!

My approach

I generally reserve the time blocking approach for when I have a lot going on, and I’m starting to feel overwhelmed by it all. Ideally, at the start of the work week I will set aside half an hour, and look at my calendar of commitments. These are the scheduled events with other people that are locked in (usually weeks in advance) and that I need to fit all my other work around.

The next step is identifying the tasks that represent the ‘big rocks’ that I need to progress. What projects need to move forward this week? What are the tasks that need large sessions of time to get into a flow?1

Once I understand what time slots I have available for task-based work, I start creating related events on my weekly plan calendar, filling my days more completely. I need to take some care here though. I’m not an automaton, so it is important not to schedule every last minute of time. Doing that is just setting myself up to fail. In any week, unexpected things are bound to arise and time will be needed for this stuff, in addition to the general administrative tasks of email, communications, management issues, and so on.

With the weekly plan calendar populated and tessellated with my other calendars, I end up with a clear picture of my work week. At any point of time I know what I can and should be working on. I know that if I stick to the plan I set for myself, I will be closer to my goals at the end of the week than I was at the beginning. It’s a practical approach to personal accountability.

The overhead of doing this planning is not always worth the effort, but when lots is happening and it feels like control is being lost, this is a great way to reassert your plans and ensure that the important is not being overwhelmed by the urgent.

  1. Writing is a great example of this – you can’t really do it for 30 minutes here and there; you need a solid chunk of several hours.

Hardware Decisions are Hard

In the aftermath of Apple’s WWDC conference and an almost unprecedented number of new pieces of hardware have been released at what is theoretically a software development conference, I get to do some imaginary shopping.

For the past 18 months, Apple’s hardware lineup has been so out of date (except for iPhone, of course) that I’ve not even wanted to buy anything with imaginary money. They’ve righted the ship now, but in doing so are almost listing to the other side. Now it’s so difficult to identify the perfect device, I’m paralysed by choice.1


With regard to the Mac lineup, the 5K iMacs with P3 panels and Kaby Lake processors represent the first time I’ve been tempted by a desktop computer in about a decade. Combining this with extended iPad use as a mobile platform could actually work, come iOS 11.

But laptops are still the most flexible option. The MacBook (Adorable) is becoming competitive and is so diminutive, but it is still hamstrung by having a single port and when stacking price against performance, perhaps a MacBook Pro is the better option. The MacBook (Escape) is probably the pick here. Touchbar seems like a dead end that the market nor developers are excited by. Yet only the Touchbar models have TouchID which is a useful feature.

So, in terms of macOS, the most sensible use for my imaginary money is to keep it in my pocket and instead wander over to the iOS table, and see if this is an easier decision. My existing 2013 MacBook Pro has a few more years left in it, anyway.


This is the Apple cash cow platform, so what have they got to sell me? In terms of iPhones, I’m not even looking. Work provides me with an iPhone SE which is a form factor I quite like for basic tasks, and I’m not about to absorb another phone contract. Anyway, this is not an iPhone release event, so let’s move to iPad.


I’ve been a believer in iPad since it was released and I put in my pre-order as soon as the online store switched to pre-sale. I’ve been wanting to upgrade my iPad Air, and the first compelling reason to do that was the iPad Pro 12.9″ (1st gen). But then the iPad Pro 9.7″ was released and everything got out of sync with what model had what features. I knew the sensible thing to do was wait for the next revision.

My waiting has paid off, because these are the devices I’ve dreamed of. Beautiful 120Hz ProMotion displays, accelerated Pencil sampling and come iOS 11, proper support for multitasking. Yes, I want one! But which one? The 10.5″ looks to be everything I could want, until I realise it doesn’t support two full screen iPad apps side-by-side. One of them has to use the iPhone view controller. That does not fit with my productivity needs.

So it looks like it falls to the iPad Pro 12.9 (2nd gen). This has all the power I want, but I will be trading off couch comfort. Where is my Goldilocks iPad?!

Missing the four quadrant product matrix

When Steve Jobs returned to Apple and started its turnaround, one of the first things he did was rationalise the product line down to a four quadrant matrix. It was simple: on one axis, professionalconsumer, on the other axis, laptopdesktop. Here was enough breathing room between each of the specs and the prices of these machines that it became quite easy to choose which was for you.

Now, as Apple’s product line expands, they have a much larger matrix. This has resulted in overlaps across price, capability and function. Is the iPad a suitable laptop replacement; or is a laptop a necessary complement to an iPhone?

With my imaginary money, I think my decision is to keep my MacBook Pro and replace my ageing iPad Air with an iPad Pro 12.9″. That should be enough to keep me going for the next year or two, at which point solving the computer problem will be a more pressing problem which I hope, by that time, has a more apparent solution.

  1. They have become a perfect example of the theory of paradox of choice.

More Productive on a Mac

A good tradesman values his tools, and generally has a preference for one piece of equipment over another.

In my trade, the computer I use is my primary tool. My tool of choice is a Mac. I am able to be so much more productive on a Mac because it’s the tool I know inside out. Over years I have customised how the operating system works, added on various tools, and generally made it work even better for me than it does out of the box.

Unfortunately, in my organisation Windows remains king. My employer doesn’t have a formalised Bring Your Own Device policy, but at least in recent years they have made WiFi available for staff, although it is firewalled from the main networks.

Corporate IT versus innovation

Employees are assigned Windows-based equipment to staff, and only company-issued hardware is supported by IT. Only their Windows devices are able to connect and authenticate directly with the official network. These devices are also completely locked down so the user cannot install or customise these platforms to suit their own needs or abilities. This is based on the assumption that a worker will only ever want Microsoft Office, and the overriding preference for corporate IT to make their job easier.

I think this approach stifles of innovation. The use of applications that go beyond Office can allow for employees to discover more creative solutions to problems. If the only tool you have is Word/Excel/Powerpoint, then every problem has to be resolved in the same limited way. Yet I love mind-mapping with iThoughts, then using OPML to move the concepts between a map and an outline in OmniOutliner. I am faster using Launchbar than the Mac’s Finder (and infinitely quicker than using Windows Explorer!). I have Keyboard Maestro1 and Hazel managing the system and moving files and folders around automatically on my behalf. I write long-form business reports in Scrivener. Then, I can use all the hooks across the Apple ecosystem to establish synchronicity with an iPad 2. All of this customisations represents innovation that makes me more efficient, but all of it is in circumvention of corporate IT. If I limited myself to a Windows PC I would be worse at my job. I wouldn’t be happy if my carpenter was forced to use a junky Ozito saw for all his work, and I don’t see why knowledge workers are so often limited in the same way.

Firms need to move with the times

With the move to more cloud services, firms have the opportunity to release the reins on device management. Establishing and supporting a Bring Your Own Device policy becomes much easier when the device simply becomes a node connecting to cloud storage, email, and so on. If a company doesn’t support an employee’s efforts to expand their creativity and efficiency, they are likely to lose their most productive and creative people.

Also, consider the next generation of workers that have been brought up on phones running mobile operating systems. If a business doesn’t effectively support a multi-device, syncing approach, they may find that younger workers truly struggle to manage.

  1. Written by a Perth developer who lives just a few minutes away from me.
  2. Unfortunately, corporate IT strike again with the iPhone. They installed an MDM profile that prevents all use of iCloud – even for syncing of preferences and settings.

Personal Kanban

What is Kanban?

Traditional Kanban boards are used in manufacturing and other production environments to help visualise the flow of work and bring to attention any potential backlogs or other issues that might impact upon efficiency or productivity. When I travelled to Japan a few years ago as part of a study tour on lean manufacturing, I witnessed all sorts of kanban boards in operation to help provide factories with necessary production information.

The essential premise of a kanban board is to demonstrate the flow of work along the value chain of production. At the fundamental level, the kanban board starts with a column for ‘work to be done’, then one for ‘work in progress’, before the work task exits the value chain as ‘completed’ work. Visually, a simple kanban board will have these elements drawn as columns on a whiteboard with a series of sticky notes representative of each element of work. As the work progresses, the sticky note is physically moved along the kanban board.

Kanban boards can be used more broadly than in just manufacturing environments. More recently, software development has adopted many of the processes and tools of lean manufacturing, including kanban boards, in the design and implementation of agile, scrum and other team-based development methodologies.

Personal Kanban

I have an interest in kanban at a more atomic level – that is, how can the use of kanban boards help an individual to understand and visualise their own personal workflow. For knowledge work, understanding where somebody is at with work projects and having a grasp as to whether the situation is under control, or at risk, can be hard.

I’ve recently been reviewing my own productivity management system to see if I can better implement personal kanban myself, to help me understand just how much work I have at any one time, and how my own ‘backlog’ is looking.

My Technical Implementation

I previously wrote about OmniFocus and how that brilliant application keeps me on track. Into that I have now created some kanban contexts, and tied these to a kanban perspective.

My OmniFocus kanban contexts
My OmniFocus kanban contexts

This helps me work on my task list by seeing my backlog of items, seeing what is currently active, and being able to work on them to completion.

While OmniFocus is excellent, one of its key weaknesses is reporting and data presentation. It helps manage work brilliantly, but it doesn’t do so well at providing context. Not a management report is to be seen, other than being able to create any combination of list.

To help with visualisation, I’ve had to turn elsewhere. I have recently revised a few Trello boards that I use to help visualise my workflow, simplifying the board design and ensuring there was a very clear ‘left to right’ flow. In the process of updating Trello, I investigated a few other online kanban boards (namely Kanban Tool and LeanKit) to ensure there wasn’t a better option for me, but the best experience remains Trello.

My final step was to really nerd out by leveraging the hard work of Jan-Yves Ruzicka who has built a Ruby library called Omniboard. If you have the capability to install Ruby, and the MacOS developer tools, Omniboard can create a fantastic graphical presentation of your OmniFocus data. This is output as a single, stand-alone HTML file which can be saved to Dropbox and thereby made accessible from any device at any location.

OmniFocus data presented in Omniboard
OmniFocus data presented in Omniboard

To fully automate the process, my final task was to have Keyboard Maestro executes a shell command to update the Omniboard file on a regular basis. This ensures I have a regularly updated personal kanban board based on the activity and progress I have recorded in OmniFocus.

The Point Being?

The ultimate outcome of all this tinkering is that I now have:

  1. a tactical view of my to-do list in OmniFocus;
  2. a visual representation of my workflow in Omniboard; and
  3. independent high-level strategic kanban boards operating separately in Trello.

If clarity of information is important to managing workloads, then I am now in a much better place than before implementing these changes. You may not wish to go this deeply down the rabbit hole, but I have found it any interesting exercise in designing a workflow system that not only helps me get stuff done, but let’s me see how much capacity I have to get more stuff done.

Budgeting and YNAB

I’ve always been a money tracker. I still have ledger books from when I was 14 years old, with my handwriting tracking my money in and out. I would reconcile it to my bank savings account with little ticks.

I think I learned this habit watching my Mom as she would carefully manage the family finances at the kitchen table.1 There was never enough money to go around (not that I was aware of that at the time), so much of my Mom’s job was timing cheque payments, deferring bills, and calculating how much, if any, might be left over for the week. Such was life for a divorced mother of four living on not much more than a pension and without any support from her former husband and father of the aforementioned children.2

As I grew and got my first part-time job, my money-tracking ways continued. Each week I would record my income, and understand how much money I had available to get me through to the next week.

I got a bit older, graduated university and got a real job. By this point I had graduated to electronic money tracking. For a short while I used Microsoft Money, before settling on Quicken and using it for years. Each year, they would release a mediocre upgrade and I would pay the license fee to keep using it. Year after year that software got worse.

I got married and we took a traditional approach to finance by merging our money. What was mine was hers, and what was hers was mine. Fortunately, my money tracking addiction could continue since while my wife is financially aware, she didn’t have a compelling urge to record and reconcile the way I did!

Eventually Quicken became so terrible that I couldn’t bring myself to pay for it anymore. This was a dark time. There was no compelling software to adopt so I rolled my own Excel spreadsheet and used that. This was probably the first time since my ledger books that I wasn’t recording transactions. Instead, I tried to take a high-level approach by using a budgeting/forecasting model. It felt like it was working at the time but in hindsight we fell into a bit of a financial hole without realising it. We were relying on future income to cover past expenditure – what is referred to as ‘riding the credit card float’.

About 3 years ago, I realised that my carefully managed spreadsheet was busy work that was actually not helping us meet our goals. I did another software review and this time I found the application that changed everything: YNAB (short for You Need a Budget). YNAB took me back to my roots. It required transaction monitoring and was backed by a ledger that needed to be reconciled. But the magic trick of YNAB is that first and foremost, it is a budgeting system. As much as I had tracked money for all those years, and generated my income and expenditure reports, it was always backwards looking. I was auditing what had already happened, but not making commitments about what my money should do in the future. YNAB completely changed my perspective on personal finance management.

YNAB is all about giving jobs to the money you have on hand right now. You budget that available cash down to zero, then stop. You don’t live on the credit card float. You don’t plan to spend more than you have. You allocate the money to a series of planned expenditures, and then track progress against that. If you overspend you get immediate feedback and can adjust your budget through reallocation – as YNAB says, you ‘roll with the punches’.

While this seems like short-term budgeting, it actually facilitates long-term goal realisation. You suddenly realise how finite your cash supply is, especially after accounting for those recurring bills and putting money aside for the big annual bills3. With the little amounts that are left over after setting money aside for the necessities, you can make some hard decisions about what you want to do with that discretionary cash.

Since using YNAB we have never been in a more solid financial position. We can pay all our bills as and when they fall due (even the big ones). We can save and invest for our family’s future. We can set aside money for fun.

The best thing of all, though, is that we do not fight about money. We have no nagging money stress between us. We share our income, we share our expenses, and we share our savings goals and spending intentions.

After having managed my money very carefully for almost 30 years, this is the best it’s ever been. I endorse YNAB wholeheartedly. Get it, use it, love it!

  1. This was the pre-computer era, when every task people did was so much more visible.
  2. I will never cease to appreciate how my Mom was able to keep it together under such difficult circumstances.
  3. Think insurance, school fees, council rates. All the ‘oh, crap’ moments!