(This article was originally posted on The Voice Nook on Substack.)

I have a confession.

I, like many people (women?), have this intense, visceral belief that somewhere out there in the world of office supplies, exists the Perfect Planner.

This past Sunday, I spent over 60 minutes between Staples and Target opening and closing and reopening Every Single Planner looking for some magical system that would promise to organize me into a better version of myself.

If, and only if, I could find the right paper type, font style, and page size, with a smooth spiral binding, and the perfect layout combination with the precise amount of spaces for weeks, months, days and notes, then I, Samantha Mathilda Whitehouse, 48 years old, originally from Saugus, Massachusetts, could finally be free.

Inshallah, bitchez. ✨🙌🧿🙌✨

This is not new terrain.

I have been here before. Many times.

In fact, I already have a planner for 2026.

With shipping, I paid $62.94.

Sixty. Two. Dollars. And. Ninety. Four. Cents.

For a notebook with a calendar in it.

It’s called the Curation planner. It’s supposed to help you curate your life. The paper is fine. The layout is fine. The size is fine. The spaces and columns for days, weeks, months and notes….fine, fine, fine, and fine.

I have written in it three times.

Three. Times.

A moment of clarity hit me around the 57 minute mark as I recalled this dusty book.

“Sam,” I said to myself out loud in the calendar aisle of Staples from my blurry-eyed fugue state, unable to notice or care if anyone was around me to hear: “Pray tell, what exactly makes you think any sort of crisp and delicious planner is going to solve anything for you this time?”

The mercifully, some adult version of myself grabbed my younger self by the collar and marched us both out of the store before any of us could circle through the same old (well-intentioned but ultimately unhelpful) doom spiral of looking for solutions and support in the wrong places, not having them work, then feeling like there is something fundamentally broken about myself because, once again, I did not change.

I sat in my car for a moment, having a snack and sipping some hot tea that used to be iced, and feeling a little defeated.

No new planner = no new me.

Sigh.

While eating some sour cream and onion chips and waiting for the caffeine to kick in, I kept wondering why, after all these years and abandoned attempts, do I still believe that somewhere in the pages of a planner is a version of me who has all their shit together?

And furthermore, why do I believe that just because I’m not able to commit to someone else’s printed system of organization that somehow I don’t already have my shit together?

For years, every abandoned planner, spreadsheet, and platform (I do not want to talk about Todoist or Pipedrive today, thankyouverymuch), has seemed to reinforce, again and again, that I’m the kind of person who can’t get organized.

And that because of this, I’ll never be productive enough, disciplined enough, successful enough, or good enough.

To be fair, that’s a lot of pressure to put on a notebook with a calendar in it.

And also, it’s a lot of pressure to put on myself.

A planner is a neat little system for writing things down and checking them off.

It’s not aware of the conditions of life.

It doesn’t understand that tasks like ‘text mom about the potluck’ have years of emotions stored within them.

It’s never experienced being overwhelmed vs feeling well-rested.

It can’t solve for financial strain or offer helping hands.

I finally realized that I’ve been asking this teeny tiny microscopic system to hold up an entire ecosystem filled with complexity.

No project management tool – no matter good it feels to roll your favorite pen along its pages – can do all that.

Perhaps I haven’t been failing at organization and perhaps I don’t need to find some other better version of myself.

Perhaps the problem is that I’ve been trying to apply an overly simplified support tool to an terrifically complex situation.

Look, I love systems. I looooove them. I’m not suggesting that we all stop using systems. And I’m not even suggesting that I’ll stop shopping for planners.

What I’m trying to do (as usual) is offer myself grace.

Particularly for the moments when I’ve chosen a system of support that isn’t actually aligned with the conditions I’m living in and ultimately cannot support me – and then blamed myself for the failure.

And from here, I can get curious…about what’s really going on, and what support I really need, and where I can find that instead.

I don’t need a new planner to find the better me.

I need current me to stop believing that I’m failing…when I’m not.

I’m curious…what’s the ‘planner’ in your life?

Is there a support tool that’s not working for you in the way you expected it to, but somehow has you feeling like you’re the broken one?

I’d love to hear from you.

Feel free to leave a comment, send me a private message, or book a friendly chat. ❤️