Why your calendar is a house of cards (and what to do about it)
I'll just say it: I am the worst boss I've ever had.
I tell myself the worst things I would never say to anyone, ever. In my mind, it’s just me, three businesses, two kids, and a Google Calendar that looks like a toddler threw a handful of confetti at it.
If that sounds familiar, keep reading. Because I've been thinking a lot about time lately — not as a productivity problem to solve, but as a relationship to actually understand.
The freedom of entrepreneurship has a shadow side nobody warns you about
When you work for yourself, you are in charge of everything. Your hours, your clients, your boundaries. It sounds dreamy — and it is — until you realize that nobody is holding the structure for you anymore. Most of us swap one cage for another. Instead of a boss telling us what to do, we have an invisible pressure to do everything, all the time, with zero guardrails. The freedom is real, and so is the overwhelm.
Time blocking fails working parents — here's why
The reason your carefully crafted time-blocked day falls apart by 9:15am isn't because you lack discipline. It's because your life is not a spreadsheet. One sick kid, one late drop-off, one unexpected email — and suddenly your whole day is a house of cards on the floor. Rigid time blocking creates the illusion of control, but it actually makes things worse when life (inevitably) happens. The chaos means the system was never built for your reality.
Create the calendar you actually want — then let people work around it
Here's the reframe that changed everything for me: instead of asking "when are you free?", decide when you are available and offer that. Pick the days you want to do certain kinds of work. Give people two or three options from those windows. You will be shocked how quickly people make it work. The best part? You stop feeling like your schedule is something that happens to you and start feeling like it's something you actually designed.
Zoom out to the month, not the day
Most of us are managing time one chaotic day at a time. But if you zoom out and look at the full month — how many big events, how many work-heavy weeks, how many pockets of rest — you can start to see patterns and plan ahead instead of react. I started doing this with my husband on Sunday nights and it genuinely changed how we function as a family. Even just knowing what's coming four to six weeks out takes the edge off.
Your cycle is a scheduling tool you're not using
This one doesn't get talked about enough. There are real, predictable windows in your month when you are built for big energy, deep connection, and high output — and there are windows when your body is asking for less. If you've been cramming your most demanding weeks into your luteal phase and wondering why you're running on empty, this is your sign to pay attention. When you start planning your calendar around your cycle instead of against it, you stop fighting yourself. And that alone is a total game changer.
Want more of this?
I recorded a voice note type episode, where I’m sharing what my relationship with time looks like right now, my honest backstory of how I went from advertising to corporate to entrepreneurship and back again, and what I’m planning to do when I come back from a well deserved family vacation.