92 days ago I was horrendously lazy.

It was a “bad spell”, but one that has been reoccurring several times a year ever since I started caring about my productivity.

As a remote freelancer, motivation needs to come from within. You don’t have a boss breathing down your neck. You have deadlines, but you don’t have to be anywhere. There are appointments, Skype calls, sure, but there’s no clocking in, no accountability.

For some people, myself included, the endless torrent of willpower that seems necessary to keep going through failures and setbacks for years at a time can quickly dry up.

I’ve spent years – YEARS – trying in vain to improve myself and become the man that I want to be, the sort of man I would admire. The sort I would want to have as a dad if I were my son, or as a husband if I were my ideal woman, or as a business partner if I were Elon Musk.

Every time I made a little improvement, I’d soon slip right back.

I became jaded.

Perhaps the self-development gurus are taking us for ride. Type-A personalities, with brains that are wired from birth for success, selling books to chumps like us, promising we can become the same thing (if we reeeaaaally try).

Maybe it’s true what St Loyola said: “Give me a child until he is seven and I will show you the man.”

Maybe you can’t teach an old human new tricks, any more than you can teach an old dog.


Except you can teach a dog of any age a new behaviours, and I already knew from experience that my own brain was malleable.

My journal was proof

Journaling used to be just a difficult for me as anyone. When I was 14 I decided a diary might help me get through some of my adolescent angst.

Months would go by without any entries sometimes, but I never gave up. I kept at it.

One day, something changed in my head.

I woke up and I wanted to journal, more than I wanted to avoid it!

I can’t tell you exactly when it happened, but if you graphed my journaling frequency you’d see a sudden spike, and then a plateau, a new norm, that hasn’t dropped ever since. I even started journaling too much at times, and had to exert willpower to journal less.

I rewired my brain.

Lasting change is possible. Our behaviours, our preferences, our characters, are not set in stone.

Without that reference point, I might have given up. I might have started believing self-fulfilling lies such as, “I’m just not a morning person,” or “I can’t focus on one thing for very long,” or “I’m just a disorganised person… it’s who I am.”

With it, however, I knew it was possible to change my behaviours, my preferences, maybe even my character. Even in the deep levels, the emotional centres, I could reach in and re-train myself into a more effective person.

In time, I could become that awesome future boss-man self that I dream of.

At least, that’s what I hoped.

In reality nothing else I tried ever stuck.

Why nothing else was working

I knew it was possible to become a morning person who got things done well in advance of deadlines, who was bold and brave and tough, well-muscled, well-rested, well-connected… a highly disciplined force of nature… It must be.

So why did nothing ever stick?

Apart from journaling.

My entries remained thick with ramblings and opinions, thoughts which seemed to evolve over time.

To my horror, one day I discovered they hadn’t evolved at all.

The good thing about a personal journal is you can’t trick yourself into thinking you’ve made progress when you haven’t. When I migrated my files from one journaling app to another, I skimmed over some entries from a couple years ago, when I was still in university, and guess what – I was complaining about the exact same things! I was shocked. I felt sure some things had improved, but my internal problems were still essentially identical.

Broke because I didn’t work hard enough. Alone because I wasn’t brave enough. Tired and unfit because I wasn’t consistent enough.

The same damn problems, more than two years later.

Fast forward a few months, it’s mid-summer 2014, and that discovery was still plaguing me.

You’d have thought it would have motivated me to finally make lasting change, but the opposite happened.

I got worse.

I had some money saved up, and went back to home for surgery on an old injury and spent a few recovery months with my parents for free.

I really didn’t have to get up for anything then.

I could feel what remained of my drive to succeed wobble and collapse. The last whisper of faith in myself started to fade.

I had to do something.

Something small.

Something long-term.

Something that would guarantee success in some measure, no matter what.

I asked myself a question: “What daily habit would mean I still got stuff done, even if I let everything else go – wind up obese and sleep deprived, waking up in a damp ghetto flat next to a old hooker speckled with cocaine – what daily habit would mean even then, I would still drag my sorry arse up and get things done?”

The solution unfolded itself on a Greek plinth within a golden beam of sunshine in my mind…

The Assignment Challenge.

Every day, write down what you really want to get done. These are your Assignments. Before your head rests on your pillow that night, complete and cross off every one of them.

That’s it.

That’s all I really needed.

Over those years of wasted effort, I noticed, I had been shifting focus constantly. One month I’d be trying to eat a Paleo-type diet, then I’d be tracking my sleep and taking supplements, then a week later I’d be tracking the hours I worked, and after that I’d “realise” that really what I needed was to get up early and drink “bulletproof coffee”.

Thanks to journaling, I had recorded that pattern.

And finally learned from it.

All the things I tried were good things, sure. They might have helped me improve my performance by 5% if I were already kicking arse as a corporate executive, aiming to get that little extra edge over the competition for that corner office, or whatever. But none of them guaranteed any level of success in life. I could get enough sleep and track my food intake and still be a total failure.

So what if I could only spend the next month – no, the next 90 days – focussing on this habit, and this habit alone?

As I sat in the back of a car on the way to a shopping mall, my shoulder recently stitched back together, I picked out my notebook and started to stitch my life back together.

Day 01 ▢

Day 02 ▢

Day 03 ▢

I wrote down every day, from 01 to 90, and as I did so the scale of it began to set in.

90 days is a LONG time!

It’s 3 damn months.

Triple the typically-touted length of time it takes to make a new habit. You hear about the 30 day challenge from all over the internet from personal development bloggers, lifestyle designers, and biohacking badasses, but it had never worked for me before. I hadn’t heard much about making a 90 day commitment to a single new habit, though. Most focus on how to make it easy for people to get started. But I was done with easy. I’d had it with quick, step-by-step, tips, tricks, and hacks.

I was ready to see what a real commitment would do.

And two days ago, I fulfilled it.

Yesterday, after three months of making and completing a focussed to do list every single day, I intentionally broke the habit, just to test how deep it’s gone.

The result?

…It’s pretty deep…

I found it impossible to do none of my to-dos, (something that would have been quite easy at the start of this), but I did manage to leave a few big tasks, and today I’m looking at my backed-up list and I hate the fact that I’ve still got some of yesterday’s tasks to deal with.

What used to be bizarre to me is now normal. I’m no longer a person who likes to put things off.

It’s not over. I could still slip back. But to keep this thing going will not be difficult.

And to improve on it with a new challenge – well, that makes me geekishly excited.

I’ve already got a few more Challenges on the go, but none are so task-focussed as my first.

The Assignment Challenge stopped me from procrastinating on things over the course of multiple days, and my next is going to eliminate procrastination within the day.

I’ve spent too much of my life boasting about things I haven’t done yet, and somehow, that doesn’t help them get done.


So I’m going to wait until I’ve completed this next Challenge before I expound on it in writing.

I’ll be a different man by the time I do.