Anchor yourself through change with rituals.
Your business needs ritual just as much as strategy
I can’t help it—once the Fall season hits the Northeast, it’s all pumpkins and fresh pencils for me.
This year, the sheer amount of nostalgia this season evokes has me thinking about rituals—the ones that anchor a business, a season, a self. September, with its familiar back-to-school energy, often invites that kind of reflection. Even if no one's packing a lunchbox in your household, there’s something about the shift in the light and pace that calls for new structure.
Rituals don’t have to be ornate or even daily. But they do need to be consistent. They create containers for clarity in a world that often feels overstimulated and uncertain. For creative business owners, in particular, rituals provide a rhythm that supports both momentum and rest.
Here’s the thing: business is more than goals and metrics. It’s about how you show up. And how you show up is deeply shaped by your internal environment. Rituals help you tend to that space. They protect your energy and help you come back to center when things feel chaotic or unclear.
So this month, I’m coming back to the rituals that remind me who I am and why I do this work. Weekly walks past the horse pasture. A standing Friday check-in with myself and the business. Early mornings to think before the emails roll in.
What structure supports your energy this season? What are you bringing back or retiring?
What are you unlearning?
Most businesses carry a layer of old decisions that made sense once: a workflow that used to save time, a client model that worked two years ago, or a marketing strategy that felt cutting edge (until it wasn’t).
If something in your business has started to feel heavy or needlessly complicated, that might be a sign it's time to unlearn. If you don’t, you could be building up layers of resistance and heaviness that make it hard to keep up with what it takes to build your dream. Will you still be able to do what you love later in life, like Bob?
One of the simplest prompts I return to is: "Would I choose this again today?" If the answer is no, it doesn't mean the original choice was wrong—just that you’ve evolved.
Sometimes growth means letting go of what used to work.
It takes courage to unlearn, especially when the old way still sort of works. But sticking with what’s familiar can quietly hold your business back. The tricky part is that unlearning often feels like going backward before it feels like progress. You might experience a dip in confidence or momentum. That’s normal.
Try setting aside time this month to audit what you’re clinging to out of habit. That offer, that tool, that schedule. What are you afraid to let go of? What might open up if you did?
Does the scale of progress feel microscopic?
Somewhere along the way, we were told that real success means more: more clients, more revenue, more headcount, more everything. And while that definition can work for a time, it’s not the only one worth aspiring to.
(I recently unsubscribed from it, myself—hbu?)
What many founders find out after they’ve taken a big swing in their businesses might surprise you if you’re early on… At some point, they realize that constant growth doesn’t feel energizing anymore. That scale is complicated, expensive, and * gulp * not nearly as fulfilling as they’d imagined. The shine wears off, and the trade-offs get real.
I want to point this out, because right now, your growth might feel too small for where you want to be. But let me direct your attention away from the big numbers for now to see if there are any other ways you want to define success.
Maybe your version of success right now looks less like scaling endlessly and more like…. Running a business you genuinely love—one that pays you well, supports your team, and leaves space to enjoy the non-work parts of your life?
Maybe your growth target is 10% or 15% instead of 25%?
That’s still meaningful, sustainable progress, and it absolutely counts.
One way to make peace with slower or “microscopic” progress is to find a framework that helps you pin your choices against your goals clearly. When you know what to measure new opportunities against, it becomes easier to choose what to adopt and what to leave behind. For some, that framework might look like:
- Values-first: Does this align with the kind of leader, teammate, or partner I want to be?
- Energy audit: Will this add energy to my life—or drain it?
- Seasons of business: Does this fit with what this season calls for, which might mean stability, expansion, rebuilding, or rest?
- The two-year test: If I commit to this, will I still be glad I did in two years? Is this something I can give myself a year to try, or do I need to be all-in?
The truth is, you don’t have to keep chasing bigger just because that’s the story you started with. There’s power in finding your “enough,” planting your flag there, and choosing to stay.
When it all starts clicking
A shift doesn’t always come with a bang. Sometimes, it’s just a call that goes even better than expected. A lead that converts easily. A feeling of "this is working" that sneaks in quietly.
Momentum often builds invisibly before it becomes obvious. What looked like a long plateau was really a buildup. Those breakthroughs didn’t come from major overhauls—they came from trusting the process long enough to let things settle.
If you’re in the stretch of building where things still feel loose or uncertain, that’s not a sign you’re doing it wrong. It might be the season before the click.
Think back to a recent moment where something finally started to flow. What helped? What shifted?
Adding it all up…
That messy in-between space? It’s where all the good stuff happens.
There’s a particular kind of tension that comes from having a big idea and not yet seeing it fully realized. You can feel the edges of what it could be, but the execution is still clunky or incomplete.
That space is wildly uncomfortable. And also, entirely necessary in the creative process.
Too often, entrepreneurs abandon a direction before it has time to evolve. But in my experience, the messiest middle is also the most generative. It’s where the best questions get asked. It’s where the brand sharpens, the offer refines, the voice deepens.
This is also the part of the journey where your values really get tested. Will you still show up when it’s not working perfectly? Can you stay committed without external validation? This is where your resilience and resourcefulness really grow.
If you’re sitting in the blur between concept and clarity, take heart. You’re not behind. You’re right where the magic starts.
