067: When Planning Feels Like Prison
What happens when we mistake structure for straitjackets, and how to find freedom in sacred rhythms
Note: This issue is intentionally shorter than usual, as technically I’m on vacation until January 7th :) Happy New Years!
I'm sitting here at what was supposed to be a three-day planning retreat, feeling like a defiant escapee.
The calendar says it's time to plan.
The perfectly curated space practically begs for strategic thinking.
Yet here I am, experimenting with AI models and following random sparks of inspiration, feeling oddly guilty about my resistance to the structured planning I "should" be doing.
It reminds me of a planning retreat in Costa Rica back in 2020. I remember feeling an unexpected surge of anger and defiance as the coach pushed us to get clear on our vision for 2021 and map out our ideal days. Nothing was wrong with that - especially since I'd paid to be there for exactly this purpose - but something in me was rebelling against the very idea of concrete commitments. I wanted to remain in an open, expansive state rather than lock myself into specific plans.
Looking back, I understand that resistance better now. That state of open "doing nothing" wasn't resistance to progress - it was actually fueling creativity in ways I couldn't see at the time. When you allow yourself to remain expansive, to honor being in the void, something interesting happens.
Later, when you do sit down to articulate your vision, it often flows naturally, effortlessly, and with surprising power.
Of course, this is a dance. You can't remain in these expansive states forever, or nothing would ever get done. But we've been taught to fear these open spaces, to see them as procrastination or resistance, rather than recognizing them as essential parts of the creative process.
Every new planning system has felt like another set of bars, each productivity hack becoming another way to feel trapped by someone else's idea of how I should work, think, and create.
That Annie Dillard quote keeps echoing in my mind:
"How we spend our days is, of course, how we spend our lives."
For years, it felt like an indictment. Another reminder of how I was failing to contain my days within the proper cells of time blocks and task lists.
I had built what looked like success on paper - consulting business, great clients, solid revenue. But something felt fundamentally off. Like I was constantly trying to escape my own systems, only to build new prisons with better productivity apps.
The harder I pushed for control, the more I felt the walls closing in. The more systems I implemented, the tighter the constraints became. The more I tried to lock down my time, the more it slipped through the bars.
At first, my current resistance to planning this week felt like failure. Like I was somehow broken because I couldn't just sit down and map out the coming year like a "proper" entrepreneur. Just like that day in Costa Rica, part of me knows the planning needs to happen - but another part knows that forcing it would mean sacrificing something vital.
We've been conditioned to treat planning like a necessary prison. A way to contain our wild creative spirits. A system of constraints to keep our entrepreneurial nature in check.
But what if we've got it all backwards?
What if true planning isn't about confinement, but about creating space for what matters most?
What if the right rhythms don't imprison our creative fire, but actually create the conditions for it to burn brightest?
That's when I started exploring what I now call sacred planning rituals. The word "sacred" isn't about religion or spirituality even - it's about honoring what's true for you, about creating practices that set you free rather than lock you down.
Instead of building better prisons, I began creating open spaces that could flex with my energy.
Instead of forcing rigid schedules, I started flowing with my natural rhythms of focus and rest.
Instead of fighting resistance, I learned to use it as a compass pointing toward freedom.
The transformation wasn't instant. But gradually, the walls began to dissolve:
Projects that used to feel confining began to flow with an ease I'd never experienced.
Decisions that used to trap me became clear when viewed through the lens of sacred rhythm.
Progress that used to require constant control started feeling natural, like moving in open spaces.
Here's what I now know to be true after working with hundreds of entrepreneurs:
Your business won't thrive through tighter constraints. It will thrive through better rhythms that honor your natural way of working.
Your planning systems won't stick through stronger walls. They'll stick through deeper alignment with how you naturally create and contribute.
Your vision won't manifest through stricter control. It will manifest through practices that support your unique genius while respecting your natural limitations.
This is why I'm not forcing myself to plan this week.
Yes, the planning will happen.
Yes, 2025 will have direction and purpose.
But it will emerge from freedom, not confinement.
Just like in Costa Rica, what feels like resistance might actually be wisdom - the part of me that knows when to remain open and when to crystallize vision into form.
I've watched this liberation happen again and again:
The visionary entrepreneur who broke free from rigid systems to find her natural rhythm
The systematic thinker who unlocked his creativity by loosening the constraints
The intuitive leader who found freedom within flexible structures
Each discovered that planning rituals create sustainable success not by imprisoning us in someone else's system, but by setting us free to work with our nature. They learned to dance between structure and essence, between concrete plans and expansive possibility.
That Dillard quote doesn't feel like a sentence anymore. Because now I understand - how we spend our days isn't about perfect confinement or maximum control.
It's about creating rituals that free us to serve our highest vision while honoring our deepest nature.
It's about finding freedom in rhythm rather than resistance. It's about turning planning from prison into liberation. It's about knowing when to remain open and when to give form to vision.
The path forward isn't through tighter constraints or better containment. It's through deeper alignment with who you are and how you naturally work best.
With Love, Phil
P.S. If this resonates with your own journey to break free from rigid planning systems, you might be interested in joining our 30-day Sacred Business Planning Rituals Challenge.
Beautiful !