Examining expected problems

A product lesson from a very cold window

A little while ago I (finally) got myself a decent desk and set up my workspace. It’s set up next to a window, which is nice (even if the view is of a brick wall). I’ve even got a window box - look Ma, I’m a proper adult.

However, since snow arrived in London, it’s been incredibly unpleasant - the window is freezing! That’s not a huge surprise given it’s a 110 year old building and these are traditional sash windows.

At first I tried using the blinds to try and trap the room’s heat. I whacked up the radiator… no success. After a few days of shivering I started looking up how much replacing the old window with new double glazed sash windows would cost - as much as I do want my home to eco-friendly, £800+ per window is not ideal.

So I started actually investigating where the cold was coming from. On closer inspection, there were just a few areas where a breeze was getting in. Armed with a £1 roll of draft excluder, I set about plugging the gaps.

Is the window still cold? Yes, but it’s a significant improvement.

Sometimes we assume that the deficiencies of something are inherent. I expect that old sash windows lose heat, so I assumed there was nothing I could do about that.

But assumptions mean we don’t bother to investigate problems. To what degree are the problems we’re experiencing are immutable? With inquiry we may find that much of the problem is easily addressed, or at least mitigated.

The same is true for technology products. Before you throw away the website/app/tool that you take for granted is not fit for purpose, look for the low hanging fruit that would make it, if not loveable, much more bearable to use. 

The right tool for the job

A round up of the tools I use for organization


  • To-do list - Things, Dropbox Paper

  • Habit Tracking - Habitify

  • Goals - Dropbox paper

  • Notes and writing - Dropbox paper

  • Progress - Google Sheets

  • File syncing and backup - Dropbox

  • Calendar - Apple Calendar, Google Calendar, Calendly

  • Email - Apple Mail

Effortlessly written whilst enduring train delays at Finsbury Park, London 🚈❌

To-do list - Things 3, Dropbox Paper

Task: Track what I’m doing (today, tomorrow, months from now)

I always recommend starting with a physical notebook. It is inherently the most flexible to-do list tool out there - great for when you’re just getting used to working with a to-do list. Plus, it comes with all the other benefits of a notebook. If this works for you, try out the Bullet Journal system (and then simplify it because it’s crazy overboard).

Having said that, I kept finding myself without my notebook at crucial moments, and the most important thing with a to-do list is that you always have it: you need to write everything down, and can’t afford to miss anything due.

Things is a great tool:

  • Clear UI

  • Spaces allow you to organize tasks sensibly

  • On all devices (synced)

  • Fast

However, whilst I do recommend Things:

  • it did take me quite a while to get used to it, and it still doesn’t feel amazing.

  • its price range may be prohibitive - try a free to-do tool and make sure a digital to-do solution works for you (Try Todoist)

  • it’s missing collaborative to-do lists

As I mentioned previously, I’ve recently started restricting myself to 10 things a day. Once I’ve chosen my ten things for today and tomorrow, I move them out of Things and into a Dropbox Paper document.

Things 3 →

Todoist →

Dropbox Paper →

Bullet Journal →

Habit Tracking - Habitify

Task: Track what I do every day

A to-do list should only be a place of “I-must-do things”, and if a habit is there, it means it MUST be done every day. That stressed me out. If I missed a single day, the to-do list would become cluttered, but I didn’t want to delete the habit and I didn’t want to leave them undone, either.

From Habitify’s interview with me

Habitify is pretty flexible and is very simple to use. Crucially, it lets you distinguish between failures and purposeful decisions to skip a day, and its progress tracker offers reasonably visualization of your productivity.

As with to-do lists, there are free alternatives out there - let me know if you find success with any! However, I’ve tried at least 4 others and Habitify was the first that stuck.

Habitify →

Goals - Dropbox Paper

Task: Track what I want to achieve in the future

I have a Dropbox Paper document where I track my goals at a yearly and monthly level. I’m already setting goals for 2021. These goals inform the tasks I set in my habit tracker and to-do list.

Dropbox Paper includes to-do list functionality, including setting due dates, reminders, and assigning tasks to people.

Dropbox Paper →

Notes and writing - Dropbox Paper

Task: Write things down

More generally, I also use Dropbox Paper for all my note-taking and document writing. I really love its user interface, which strips out all the unnecessary power features of Google Docs. It has great collaborative functionality. You can even reference other documents, creating a wiki-like interconnected set of documents.

Also, Evernote sucks. Do not use Evernote.

Dropbox Paper →

Progress - Google Sheets

Task: Track and visualize data

Google Sheets is the ultimate data dump and dashboard. I use it to track all my health and exercise metrics.

If, for instance, you want to track your weight, you could reach for Apple Health or some Android equivalent. One year in you’ll probably realize that tracking this data doesn’t actually help you do anything with the data. Then you might try exporting data from the app, and realize it’s in a bloated XML format that’s incompatible with other software, and you can’t do anything with the data.

I suggest you make a spreadsheet in Google Sheets and put the data in there. You can actually leverage your data and gain insight from it - create various charts to visualize it more effectively and create moving averages to pick out trends in the data.

Google Sheets →

File Syncing and backup - Dropbox

Task: Access your files everywhere

Dropbox is a really effective way of making sure you always have access to your files. If you’re going to pay for any of these tools, I recommend it be this.

A warning: I’ve had really bad experiences with iCloud - notably, pictures and files going missing and huge issues leaving the platform.

Dropbox →

Calendar - Apple Calendar, Google Calendar, Calendly

Task: Track my schedule

I mostly use the default Apple Calendar - it does the job and it reliably syncs across my Apple devices. In addition, I use the calendar of my Gmail account as some services (such as Dropbox Paper) have calendar features that only work with Google Calendar.

In addition to Calendar, I find Calendly extremely useful. It provides a way for people to see your availability and even book time with you. It’s been extremely useful whilst looking for a job,

Calendly →

Email - Apple Mail

Task: Emails

I’ve tried so many different email services and yet keep coming back to Apple’s default Mail application. The others have either:

  • Gone out of business

  • Failed critically

  • Had issues with account synchronization across devices

  • Poor search functionality

In the end, I gave up trying new email clients and stuck to Apple’s which is at least reliable. However, if you can recommend me one send it my way!

So that wraps up this list of my go-to tools. Let me know if you think there’s something I should try out!


Note: I have an iPhone and use Apple computers. Some of these services may not work (as well) on Android/Windows devices.

Habit Tracking

Distinguishing between a habit and a task


  • If a task MUST be done, it belongs in a to-do list

  • If a task is ASPIRATIONAL and REGULAR, it belongs in a habit tracker

Effortlessly pondered over a veggie fry-up at the Green Garden Cafe in Hornsey, London 🌱🍄

I’ve spent the past 6 weeks looking for a new job.

It has been as all-consuming a process as ever. Interviews and technical tests consumed a significant chunk of my free time and left me tired for the remainder. I let my goals and routines slip.

My running training stopped completely (and unfortunately I’ve had to downgrade my upcoming Valencia marathon to a 10k). My Duolingo progress tailed off. My One-Punch Man-inspired exercise regime ceased.

I view these goals and routines - aspirational and maintenance tasks like exercise, hobbies, and self-care - as the engine that keeps you productive. They make you feel good, happy, and keep your mind active, better enabling you to take on other tasks. They’re building towards an ideal future you.

But it’s hard to work towards the future when it’s shifting around you.

Two weeks ago I stabilized. After a few days in Stockholm, Sweden, I returned to London with a clear head and renewed motivation. I picked up where I left off and was back on target immediately.

When I’ve gone through similar disruptions before, I’ve struggled to bounce back quickly, and I believe the key this time around was my habit tracker.

What is a habit tracker?

I’ve used to-do lists for a long time, but habit trackers are meaningfully distinct from to-do lists.

A to-do list should only be a place of “I-must-do things”, and if a habit is there, it means it MUST be done every day. That stressed me out. If I missed a single day, the to-do list would become cluttered, but I didn’t want to delete the habit and I didn’t want to leave them undone, either.

From Habitify’s interview with me

However, if you miss your exercise target for a day, you can’t make up for it the next day. You need to be able to move past that small failure and tackle the next day’s exercise goal. This is not what to-do lists were built for.


  • If a task MUST be done, it belongs in a to-do list

  • If a task is ASPIRATIONAL and REGULAR, it belongs in a habit tracker

I use a tool called Habitify, which I thoroughly recommend despite the price (but there are many free alternatives, don’t worry!). I use it so much they even got in touch with me to interview me about how I use the app and why it’s so important to me.

The kinds of things I use it to track include:

  • My daily exercise routine

  • Language learning

  • Meditation

  • Reviewing my goals and progress

  • “Once a week” hobbies - crosswords, playing instruments, drawing

What did bouncing back look like before?

It began with looking at a to-do list with 300 tasks - parsing those, depressingly having to delete tens of unachieved aspirational missed habits that I don’t have time to fit into my week, and maybe keeping some that I realistically also won’t achieve (only creating future disappointment). All that, before I could even tackle the overdue mission-critical to-dos.

I love to kick-off my day with my habits, helping me build up momentum before tackling my actual to-do list and my workday. It sets you up for success. This time, I could just look at today’s habits, and work through them as if I hadn’t even missed a day. With a less cluttered to-do list than previously and dopamine on my side, it was then easy to work through more mission-critical tasks.

Not only will a habit tracker help you recover from un-productive periods, but it is just a better way to manage your reoccurring tasks. You can see your progress over time, maintain a productive mindset, and eventually many of these tasks actually become second nature - true habits!

Download a habit tracker and use it for those re-occurring, aspirational tasks like exercising and hobbies.


Note: I do not count my habits as part of my 10 things a day. I block out a little time at the beginning and end of the day to tackle these much smaller tasks, and if tackling the 10 things does occasionally overrun, I can de-prioritize my habits where necessary. It’s ok to miss a day, so long as you don’t miss a second (see the 2 day rule).

10 things a day

Preventing task paralysis and over-commitment

On Monday 4th November I opened my to-do list and was greeted with 149 due tasks.

The usual feelings of being overwhelmed and not knowing where even to start kicked in. I began sorting through my tasks, moving uncategorized tasks into the appropriate categories, before systematically parsing categories in priority order and postponing non-essential tasks. Even after this process, I still had just over 30 tasks which seemed equally important.

At the end of the day I had 20 due tasks. 12/30 is not good.

I felt like a failure.

I’d barely made a dent on the tasks I had due, and I had this dread in the back of my mind that I’d have to do the same thing all over again tomorrow.

On Tuesday, I stopped myself mid-process. 32 tasks yesterday was unachievable - why did I set myself up for failure? The futility of the exercise got to me, and I decided to go down my list of tasks and simply choose the first ten that:

  1. Were a priority

  2. I could probably achieve

I added this 10 tasks to a working list called TODAY. I gave the remaining tasks a quick scan for anything that was of particularly high priority and moved it into TOMORROW.

I reviewed my TODAY list, decided that realistically there weren’t enough hours in the day, and swapped two tasks out for smaller tasks, moving the harder ones to TOMORROW.

I completed all ten tasks. Success!

Although I completed a similar number of tasks, I made sure I was prioritizing the most important ones and not wasting time with a myriad of small tasks, I wasn’t over-extending and setting myself up for failure, and I planned ahead for tomorrow. I also reduced the mental load around actually choosing what task to pick up, reducing task paralysis.

When you go to sleep feeling the day was a success, you wake up the next day ready to succeed all over again.

Limiting myself to just ten tasks a day transformed my week, and I look forward to seeing whether this behavior works well and is sustainable in the long term.


Trying out Substack

I’ve gone off Medium. Instead, I’m going to try writing (basically to myself) here.

I’m going to try writing about my journey of self-improvement, productivity processes, and coding. And maybe a little politics too.

Sign up if you’re interested.

In the meantime, tell your friends!

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