I used a megaprompt to set my personal OKRs. The side effects surprised me.
Try this at the start of Q2.
Goals.
For whatever reason, they never really stuck with me as a motivational tool.
Not for lack of aspiration or ambition.
It’s just that I don’t find goals interesting in my personal life.
Instead of setting goals, I’ve always picked directions to move into. It would leave more to the imagination.
I saw it like this:
Goal-orientation: narrow-focus, must tick off the boxes and avoid distractions.
Direction-orientation: broader focus, so if opportunities emerge and they move me in the same direction, I can make use of them.
Maybe it’s semantics, or just mental models for the same thing. I’m not an expert.
But at the start of the year, I decided to do something different.
I set goals. Extremely specific goals.
Personal OKRs
I’ve been working with OKR goal-setting frameworks for close to a decade in startups, usually with cross-functional teams.1
You first define an Objective (O): a broad directional goal you want to achieve.
Then you set Key Results (KRs): results you can break down into numbers to track whether you’re reaching your objective.
For example, if you’re a calm & fluffy cloud, your objective might be that you want to float up in the sky. To achieve that, you want to reduce your liquid water content by 30%. That’s a key result.
At regular intervals, you check in on your key results to gauge how you’re moving towards your objective. If the needle isn’t moving, this confronts you with the need to change your approach. What can I be doing better? What needs reprioritisation?
It means you have regular moments when you make deliberate choices about what you will do and won’t do, rather than trying to do it all.
If you want to dive in deeper, Google re:Work offers an excellent resource.
While I was used to running these with teams and even on an individual level as a professional inside an organisation, I had never set truly personal OKRs.
At the start of January this year, that changed.
The Megaprompt
Earlier this year, I reconnected with James McAulay over our shared passions for music, creativity, transformation, and new technology. He's been running his own personal OKR framework for years, using it to lead his company and to train for Ironmans and marathons. Recently, he turned it into a megaprompt.
I set up a new project in my preferred AI assistant and tried out the prompt.
It immediately ran me through a goal-setting exercise, but, more importantly, it forced me to figure out SYSTEMS to work towards those goals.
Specifically, I wanted to see if I could improve my execution consistency. I’ve always worked in bursts of output, often preceded and followed by periods of lower output and more reflection, introspection, and often procrastination. Could I balance this better?
The year had started with a mission.
I wanted to take bigger career risks. To invest in new directions and fields where I don’t yet have a reputation or network. That meant reducing costs, excess & distractions and building as much stability & growth into my daily life as possible. I set four objectives for the quarter. I’ll share two.
My first objective was to have a clear understanding, by the end of the quarter, of what that was going to look like. For now, that means bigger freelance projects that challenge me, mixed with a part-time job that allows me to share my passion for Berlin’s history with visitors, because after 20 years, I’m bored of being on my laptop or in offices all day.
My second objective was the system that needed to be developed to get me there:
Objective 2 — Build a focus system that survives bad days (keystone)
KR1: Implement a daily checkout → check-in loop
Checkout: clear browser, decide tomorrow’s top 1–3 (≥4 days/week)
Check-in: open laptop, journal, review priorities and start first Pomodoro before checking news, socials, email, etc.
KR2: Use a fixed focus method (Pomodoro) for ≥2 cycles/day, tracked.
KR3: No system switching for 90 days (one journal + one task board).
Pomodoro is a method in which you set a 25-minute timer for focused work, then take a 5-minute break. This forces you to break down your to-do list into manageable chunks of work.
I don’t always prefer that approach, but it is a good way to get me started in the day. It also prevents getting overwhelmed by things that are new to me.
One of the interviews I published recently ran quite long and touched on many things I felt were better left out of scope. One day, a to-do list item said: “transcribe and finish first draft”. Overwhelming. I put it off until the next day.
The next day, I changed the goal to: run 3 Pomodoros on this interview. For something that is relatively new to me (transcribing & editing interviews for this newsletter), that made the day much more predictable and manageable. I would also learn how far I can actually get with 75 minutes of focused work.
I ultimately spent about 10 Pomodoro cycles on it that day.
At the end of the quarter, I scored about 80% across my four objectives.
Good for a first run.
I finally launched Calm & Fluffy’s interview series (more on the way)
Built two apps and launched one
Lined up new freelance clients
But the more interesting wins were the side effects. It took some work, but I’ve properly transitioned away from music streaming and now rely on an owned collection. Something I'd been trying to establish for years finally stuck: daily meditation. And when I noticed poor sleep quality, really unusual for me, I addressed it with surprising ease by breaking a habit: no more coffee after noon.
If you want to try it yourself, James’ personal OKR megaprompt is worth running at the start of your next quarter. But you don’t need to use AI, the framework works on its own (read the AI-free explainer here).
ᕱᕱ For your ears ᕱᕱ
It’s been over a month since I last shared music with you. Here are some of the albums I’ve been listening to.
As soon as I heard the ambient jazz album Seeing Is Forgetting by Elori Saxl & Henry Solomon, I knew exactly when and how I wanted to listen to it again: on a warm, late evening, while cycling through the city. A week later, after a group meditation, I had the chance. It was wonderful. (discovered via the warmly recommended zensounds newsletter)
Another album I’ve enjoyed is this compilation of four decades recordings by the Kenyan artist Joseph Kamuru, spanning from high-life to afro funk and much more.
I’ve also been entranced by Max Eilbacher’s structural composition 7 Runs, an experimental work that asks the questions: Is descending a ladder to nowhere the same as sitting? Are 7 pulses equally partitioned through time, no longer a discrete measure of time?
Lastly, and most recently, I’ve been listening to this work composed by Gregorio Allegri in the 1630s, intended to be sung in the Sistine Chapel during Holy Week liturgy. The story goes that the piece was so secretive that no written copies of it existed outside of the Vatican and a few trusted places. One day, a fourteen-year old Mozart heard the piece and ended up transcribing it from memory.
Rather than being appalled and punishing Mozart for it, Pope Clement XIV summoned Mozart back to Rome and awarded him a distinction: a knighthood. Awarded for musical piracy, to a teenager, by the institution he’d technically wronged.
Miserere Mei, Deus, a beautiful piece of choral music, in this recording performed by the Choir of New College, Oxford, under Edward Higginbottom.
If your org needs help with OKRs, let’s chat.