It’s 3 months since I went freelance, and I’ve been recording a video diary almost every week to document how things are going, which I’ve been sending out to subscribers of the CMC newsletter.
However a few weeks ago the videos stopped (as any subscribers will have noticed). I had a lot of great feedback such as this from Margaret Pinard of Taste Life Twice on Facebook:
“Just got the latest installment of Ditch the Day Job Diaries, and particularly enjoyed the gardening clips (frog! goat!) and the community feel behind Freelance Fridays. And I love that quote about over and underestimating what you can do- will have to mull that one over… thanks for the great content, Milo!”
But I also got some feedback saying that there wasn’t enough info about how I was structuring my day, finding work etc. This gave me pause for thought, as if I’m bothering people once a week with a new video, I want it to be as useful as possible for them. And as fun as it was to film myself cycling to the local beach as I did in episode 8 below, perhaps it was a tad self-indulgent!
Structure? What Structure?
Now I can’t really talk about the work I’m doing for clients in detail, but I can talk about how I’m structuring my day, right?

The problem though was that I wasn’t structuring my day, at all. I’ve already written about how being productive in the morning isn’t my strong point, even when I was working full-time. Well let’s just say that leaving your job doesn’t miraculously make your bad habits disappear – in fact, for more it made them worse!
I’d quite been enjoying lying in and waking up in a a leisurely fashion, and staying up late watching daft films starring Nicholas Cage and Jason Statham on Netflix. Yes I was getting work done for clients whenever necessary, but I wasn’t taking my own creative goals forward. By the time my wife Mel got home from a full day’s work, I’d achieved very little.
Phase 1: Adjustment Bureau
After 3 months I’m the first to admit that although I’ve had enough to keep me going, the work isn’t exactly flooding in. Luckily I have a bit of a safety net for the first year but if 3 months can fly by that quickly, then it won’t be long before I’m looking back thinking ‘what happened to the last 12 months?’ and wishing I’d used the time more wisely (as I scour the bins in the alleyway behind the local Chinese takeaway for scraps of food and a slight glimmer of hope from a discarded fortune cookie).
I’m now seeing that first three months as a natural period of adjustment. After 10 years of working in the civil service I was somewhat institutionalised to the daily grind of sitting in an office all day, and I had also been diagnosed with chronic stress during the last year because of trying to juggle so many different things in my life and general unhappiness with my work. I needed some recovery time.
But I also came to realise that if I kept up my slovenly lifestyle, things weren’t going to get any better any time soon, which is why I’ve designated the next 3 months (including May) “Phase 2″.
Phase 2: This Time It’s Serious
In this phase I’m determined to finally establish some better habits, and this time failure is not an option. Now I’ve often read about how to do this, and people I respect like Leo Babauta and Michael Nobbs, amongst many others, advise starting small. Most people fail, they say, because they try to take on too many new habits and behaviours at once.
It’s true – I know this because I’ve done it time and time again – set out with good intentions to get up early, go to the gym, write every day etc etc but after a week or sometimes only a few days, it all comes crashing down again because it’s not realistic.
The sad truth is by the time you hit my age (34), or even a lot younger than that, your bad habits are deeply ingrained. It takes a lot to change them. This infographic shows just what’s involved in the process, and it looks so complicated that it puts you off even trying:
So in the interest of keeping things as simple as possible, I’ve decided to commit to two specific things for the month of May:
1. Get up at 7:30am at the latest (Mon-Fri)
2. Write 1000 words in 25 minutes (preferably first thing in the morning)
And that’s it! If I can stick to these two positive habits in May then I hope to add more over the next few months. I’m using a great website called Chains.cc to help myself stick to this plan. For this week only, you can watch a brand new episode of The Ditch the Day Job Diaries below which goes into more detail about this (episodes are usually only for subscribers).
Creative Accountability & The Clear-Minded Copywriter
I’m also having fortnightly accountability calls on Skype with Fabian of The Friendly Anarchist. Again, it took us a few weeks to get into our stride, but now we seem to have hit on an excellent system where we commit to specific weekly tasks and send each other the proof that they’ve been done. If we fail, we have to give money to the hateful right-wing organisation the BNP, which is one of the best motivations not to fail I’ve ever discovered. So that is definitely helping in terms of taking things forward with my own creative stuff.

And I’m making much more of an effort to find and apply for new work, including setting up a portfolio site called The Clear-Minded Copywriter, which I hope to add to and improve over the next few weeks. I’m hoping that if by the end of the 3 months this effort will have paid off – either way that will be the time for a review to see how things are going and what I need to do differently.
If you’d like to see how my morning routine challenge for May is going, I’ll provide updates in the next episode of the Ditch the Day Job Diaries. Sign up to receive new episodes each week plus access to all of the videos so far in the series!