Hey,
Welcome to a new issue of Experiments in Progress.
This week’s issue looks at:
How I plan a week that actually sticks (and why most plans don’t)
What made this our most profitable CES yet without chasing hype
Let’s dive in👇
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🧠 How I Plan a Week That Actually Sticks
I’ve tried planning weeks that look perfect on paper.
They never survive the week.
This is the version that does because it’s built around constraints, not motivation.
I plan in two layers:
first the week, then the day.
🗓️ Level 1: Weekly structure
At the highest level, I assign types of work to specific days.
Monday: scripting
Tuesday & Wednesday: shooting
Thursday: short-form content, admin, general catch-up
Friday: off
Weekend: family time
This does a few important things:
Keeps similar work grouped together
Reduces context switching
Makes it obvious what doesn’t belong on a given day
Protects non-work time by default, not as an afterthought
I’m not deciding what to do every morning as that decision is already made.
⏱️ Level 2: Time inside the day
Once the week has shape, I zoom in.
I’m a big fan of time blocking, but not the hyper-detailed, every-minute kind.
The core idea here is Parkinson’s Law:
work expands to fill the time you give it.
So I plan accordingly.
I don’t block every minute of the day
I compress work into defined windows
I use time limits as a constraint, not a suggestion
If I give myself a full day to script, it takes a full day.
If I give myself 4–6 hours, it somehow fits.
Same with shooting: I keep it tight instead of letting it sprawl across the day.
I also deliberately leave white space.
Not everything needs to be packed in to feel productive and overfilling the calendar is usually where plans start to break.
🔔 Non-negotiables that keep it human
Some things go into the calendar no matter what.
Gym every morning
Lunch blocks, purely as reminders to stop and eat
Family events, school stuff, holidays — all shared
That lunch reminder sounds small, but it’s huge.
If I’m deep in something, it’s the nudge that pulls me out before I burn through the day.
📱 Tools that make this usable
The tools aren’t the system. They just support it.
Apple Calendar for shared family planning
Motion to combine multiple calendars (work, personal, shared)
Fantastical on Mac for quick scheduling
Color coding so I can see balance at a glance
One look and I know:
work vs personal,
busy vs light,
balanced vs overloaded.
📱 Enjoying this newsletter? Share it with a friend who’s as obsessed with tech as you are:
🎙️ Podcast: Our Most Profitable CES Yet
CES is loud, chaotic, and easy to get wrong. This year, it quietly became our most profitable one yet without chasing hype or viral moments.
In this week’s episode of Aspiring Creator, I break down what actually worked, what didn’t, and how CES ended up driving real business results long after the show floor cleared.
Inside this episode:
How CES became our most profitable event yet (without forcing it)
Why some videos don’t land immediately and why that’s not a failure
What CES revealed about organic audience growth this year
How long-term positioning beat short-term performance
When events like CES are worth it and when they aren’t
If you’re building a creator business and trying to understand what actually compounds (beyond views and hype), this one’s for you.
💡 New episodes every Wednesday
🖥️ Next Issue: Everything I Hate About My Favorite Tech
I use this tech every day. I still recommend it.
That doesn’t mean it isn’t quietly frustrating.
In the next issue, I’m breaking down what actually bothers me — not hot takes, not outrage, just the friction we’ve learned to live with.
Here’s what you’ll get:
The “small” annoyances that slowly add up and drain focus
Features that sound helpful, but make things worse in practice
Design decisions you end up defending, even when they don’t make sense
Where convenience comes with a hidden cost
Why loving a product doesn’t mean it’s good design
If you’ve ever liked a product and still felt low-key irritated by it, this one’s for you.
🗓️ See you Thursday.