Why I Do CEO Days
I run multiple projects. Some are client work, some are my own apps, some are long-term bets on things like writing and distribution. On any given day I could be deep in code, doing a call, or chasing growth on a product I built 2 years ago.
Without a forcing function, I will spend every day in the work and never step back to ask whether the work is even pointed in the right direction.
CEO Days are that forcing function. I picked up the practice from a coach I worked with, Anna Romanovska, and it's become one of the most bang-for-buck habits in how I operate.
What It Actually Is
Twice a month, I block out a full day. But the actual structured exercise - the CEO Day itself - takes about 15 to 30 minutes.
That's it. A short, structured brain dump. The activation energy is low and it never feels daunting.
But the day matters too. The rest of it is intentionally kept free of deep work. No coding sprints, no long client sessions. The whole point is to keep my head in a different mode for the day - one where I have the mental capacity to think about vision and execution at the same time, rather than being buried in one task. I'll do light organizational work, update projections, handle admin, or just take it easy. The habit I'm protecting is the posture of the day: self-leadership over production.
I do two flavors:
Mid-month: the checkpoint. This is a check-in combined with a planning session. The core question is: Do I have roughly 50% more capacity than I think I'll need for the rest of this month? If the answer is no, I'm overcommitted and something needs to give, before it gives on its own.
End-of-month: the retro. This is more reflective. The core question shifts to: How do we set up to start the next month even stronger? I look at what worked, what drained me, and what I want to carry forward vs. drop.
The Process
I walk through the same prompts each time. It's not complicated, but it has to be structured or I'll just vibe my way through it.
Look at the numbers. How many hours am I committed to? How many workdays are left? What does that imply per day? This alone has saved me from end-of-month crunches more than once. It also saves me from going over on projects where I have a cap on hours that I bill, and keeps me honest with retainers that carry an hourly obligation.
Audit my projects. Everything I "own" goes on a list - client work, my apps, side projects, writing. For each one: am I going to feel pressured to do more on this when it's not convenient? If yes, I need to address it now, not when I'm stressed about it later.
Check in on myself. Am I managing my energy? Am I done working at a reasonable hour? Do I need to plan rest to free up capacity for next month? This sounds soft but it's genuinely the most strategic question. If I burn out, nothing ships.
Set the focus. Not a task list - a short set of priorities for the rest of the month. Things like: "plan my deep work sessions well," or "consistency over intensity," or simply "take a lot of rest time." (These are actual examples from the past - as is almost everything in this article.)
Why Twice a Month
Monthly wasn't enough - by the time I checked in, I'd already overcommitted and the month was gone. Twice a month hits the sweet spot: frequent enough to course-correct, infrequent enough that each session feels meaningful.
The mid-month one is especially useful. It's where I catch the pattern of drifting into reactive mode - saying yes to too many things, letting speculative and non-revenue-positive projects eat time that should go to revenue or rest.
What Changes After
The days after a CEO Day are noticeably more focused. There's a clarity that comes from having actually looked at the whole board. I tend to do less context-switching between priorities because I already decided what matters. I stop feeling vaguely anxious about "everything I need to do" because I wrote it down and did the math. This isn't the only planning tool I use but as I said before, it's the most bang-for-buck: a quick structured brain dump that has probably added years to my life.
If You Want to Try It
You don't need a template. You need two things:
- A recurring block on your calendar - mid-month and end-of-month. I set aside an entire day, but the exercise itself is 15-30 minutes. The rest of the day is just about staying out of deep work so your brain has room to think at the strategic level.
- A small set of honest questions - about your capacity, your commitments, your energy, and your focus.
The answers will be different every month. The questions stay the same. That's the point.