My calendar is my boss.
Each week it spits out a time blocked, colour coded and ruthlessly prioritised rainbow of tasks to be done. Blue is for sport, green is for deep work and orange is for meetings. Each has a time and place in my diary.
But, recently the two of us haven’t been seeing eye-to-eye.
I’ve become disillusioned with my old taskmaster, ignoring its beautifully optimised schedules. Instead, I’ve been leaning into this absolutely crazy thing I’ve discovered called doing what I feel like.
The athlete in me hates myself for it. He loves consistency, routine and steady progress. I can even hear him screaming from the back of my skull “You’re not being productive enough!”. But, you see my friend, what does “productive” even mean? And how much of it will ever be “enough” for you?
These are the questions that have been turning in my mind ever since I passed the very tangible milestone of my book launch in March and stepped into the sea of endless possibilities that has followed.
What We Measure Matters
How do you define a “good day’s work?”.
For some, it’s defined for you. You’re given strict KPIs and an always-on culture that worships presenteeism. You’re told (perhaps implicitly) to play by the rules already set.
It takes a while to adjust to the corporate world. But as you settle in, the numbers become second nature. You learn to hit them perfectly, exceeding them only by a small margin, lest your manager decide to move the target even further away next quarter.
A couple of weeks ago I was walking the floor at the CIPD Festival of Work and this systemic madness was on full, glittering display. Row after row of enterprise software vendors selling tools designed to track everything. Keystroke monitoring, AI-driven productivity scoring and digital surveillance disguised as workforce optimisation. The modern corporate infrastructure is deeply addicted to treating human beings like machines that just need their algorithms tuned. One more tweak and you’ll be more productive than ever.
But, what happens when this inevitably leads to burnout? Don’t worry, they’ve got a solution for that too. Instead of fixing the broken culture or measuring what actually matters, organisations throw shallow wellbeing perks at the problem. A free subscription to a meditation app to soothe the anxiety of a back-to-back calendar. A bowl of free fruit in the breakroom. And a weekend offsite on resilience to teach you how to cope with being squeezed even harder the following week. It’s trying to cure a structural problem with a colourful plaster.
Eventually, many of us reach a point where we want to take greater ownership of our time. We look for the freedom to design our own pathways, manage our own schedules and decide what success looks like for ourselves.
But the great irony of claiming that autonomy is that we almost always bring an invisible boss with us. Even without external KPIs or a manager looking over our shoulder, we volunteer to micromanage ourselves. We convert our Google Calendar into our own digital warden. We measure our self-worth by how many tasks we crossed off, how many coffee meetings we booked and how utterly exhausted we feel by Friday night.
We haven’t actually created a healthier relationship with our work. We’ve just internalised the tracking culture, becoming our own underpaid security guard policing how we spend every moment.
Before we realise it, we’re mistaking motion for progress.
The Trap of Perpetual Motion
Up and to the right is the only version of progress we’ve had drilled into us. If that line isn’t moving in the right direction, we are failing.
If you aren’t scaling your side project, you’re stagnating.
If you aren’t optimising your downtime, you’re wasting your life.
If you aren’t actively climbing, you must be slipping.
We tell ourselves, “Once I hit this milestone—once the project is over, once the contract lands, once the savings hit that number—then I will finally rest. Then I will allow myself everything I was unworthy of before.”
But when you finally reach the summit of a mountain you’ve been ascending for two years, you begin to realise this isn’t actually the end. The horizon now stretches for miles and is full of an infinite number of mountains. If you’re too obsessed with climbing, you will never allow yourself to enjoy the view. You’ll just start mindlessly marching towards the next ascent.
Intentionally resting, having days without checking your inbox and sitting yourself down to figure out what will actually move the needle are strategic tools that enable you to show up your best self.
Redefining a Good Day
Choosing your own metrics is hard. It is infinitely easier to let a KPI or a hustle bro dictate your worth than it is to look in the mirror and decide what a successful day actually looks like on your own terms.
If we want to design a truly Undefinable Life, our self-imposed metrics have to pass three criteria:
They must motivate us toward the right actions, not just any actions.
They must be entirely within our control.
They must prioritise inputs over outputs.
When you obsess over the outputs of revenue closed, books sold or deals landed, you leave your emotional state at the mercy of external market forces. But when you anchor yourself to inputs, you create a shield against fake productivity. You stop hiding behind the low-stakes bullshit tasks and admin busywork we all use to procrastinate on the big scary new initiatives that actually move the needle.
For me, the primary metric that drives everything is Momentum.
Which looks like a highly focused, non-negotiable 5 hours of deep work on the goals I set each quarter. If I give this focus to my core projects, the day is an absolute unqualified win. I did what matters. The rest is irrelevant. The colour-coded tasks left undone can wait. The input was met, the momentum was sustained and I showed up the best I could.
But, I’m not perfect (In fact, I’m far from it). I often find that work seeps into every corner of my life. I think about it on runs, I debate it with my partner and I’m guilty of constantly refreshing my emails for the next dopamine hit.
To reclaim some life back, I’ve implemented two practices. The first is that we ban work chat in the house before 9am and after 9pm. Which has meant no more late nights debating the next move. The second is what I call “white space weekends”. After back-to-backing weekend social events for months on end, it starts to feel like the walls are closing in. I have no ‘Me Time’. So now I book days where there is literally nothing to do in my diary. Where I can show up, do what I like and just be a human being.
The colour-coded rainbow in my diary isn’t going anywhere. My internal taskmaster will still scream at me on a quiet Tuesday morning and my thumb will still twitch toward the email app out of compulsive habit.
But, slowly I’m starting to learn that my worth isn’t tied to my output. I don’t have to optimise all 168 hours of my week. And if I protect my focus and do what actually matters, I’ll be able to confidently say that today has been a good day’s work.
Then, I can rest a little easier.
And live a little more.
I’m Turning Back on Paid Subscriptions
At the end of 2023 I paused all paid subscriptions. I wanted to release myself from the pressure of weekly publishing so I could focus entirely on consolidating, editing and launching the book.
Now that Undefinable Life Design is out in the world, I have the energy to show up here more intentionally. Moving forward, I am transitioning this newsletter to a rolling archive model to protect the value of the intellectual property I’ve spent the last 4+ years building.
How it works:
New Essays: Completely free for everyone for a rolling 2 months.
The Vault (£5/month): After 2 months, older essays will move into a premium archive. Upgrading to a paid subscription gives you unlimited, lifetime access to this entire 150+ post library.
If you want to lock in unlimited access to the entire archive and directly back the independent, reader-supported mission of my publication, you can upgrade your account below.
Charlie, I’m a “third actor,” following your journey from a different perspective. I appreciate where you are - from and heading to - and recognize others struggle with redefining productivity and reorienting around purpose. Best wishes!