How Freelancers Can Stop Fighting Their Natural Rhythms and Start Planning Around Them

This blog summarizes learnings from The Future is Freelance Forums. These forums are where stakeholders from all levels of the freelance ecosystem come together to surface and solve the biggest problems facing independent work. These summaries serve as a place to house our collective wisdom on these topics. As such, I want to credit everyone who attended this forum for these insights.

Before we get into what we learned from each other in the forum, let’s ground ourselves in what “cyclical planning” even means.

Cyclical business planning is the practice of designing your business around your natural rhythms instead of a borrowed template. Rather than treating every week, month, or quarter as interchangeable units of productivity, it starts with the recognition that your energy, your market, and the world around you all move in patterns, and that your business will work better when you plan with those patterns instead of against them. 

That means mapping your personal cycles (when you have creative energy, when you need to recover, when you tend to spiral), your industry cycles (when clients go quiet, when demand spikes, when it's time to sell), and the broader seasonal rhythms that affect all of us, and then building your planning structure around what you actually find. Not the business you think you should have, but the one you actually run.

When I asked registrants to describe their approach to business planning, I got a pretty honest look at where most freelancers actually are.

A handful had real systems: quarterly planning retreats, a seasonal and cyclical framework, a structured yearly-to-weekly cascade. But they were the outliers. Everyone else was somewhere on a spectrum from "short-term reactive" to "I hope for the best lol" to "Planning? Ha!" 

That's not a failure; it's what happens when you build a business without a blueprint and then try to run it using planning systems designed for people with predictable calendars and consistent capacity. Which most of us don't have.

That's what we dug into at this forum. Jenni Gritters, sustainable business coach and author of The Sustainable Solopreneur, and Ivy Bromius, magical project manager and founder of Circle Thrice, joined me to talk about what cyclical business planning actually looks like in practice, not the theory, but the real mechanics of building a business that works with your rhythms instead of around them.

Your business already has seasons. You're just not planning for them.

We started with a key question: what does your business year look like, and how much of that did you plan for versus just survive?

The word "survive" landed... hard. Because that's the experience for most people, not designing for the year, but getting through it. And the conversation that followed named something that tends to go unspoken: the slow seasons aren't surprises. They're patterns. The spring slump, the summer quietude, the Q4 sprint; these things happen roughly the same way every year. We just haven't built our planning around that reality.

Jenni described going back through her own data and noticing that spring is her lowest revenue period every single year. "Every year, I freak out. Every year in July, things start moving again. And so, next year, I will not be forcing myself to sell things when I'm having an identity rebirth in the middle of the spring. That's happened three years in a row, at this point, I think it's plannable." She also noted something counterintuitive: she makes more money when she works fewer hours. Her theory is that joy and spaciousness create magnetism in sales. That's only visible when you stop looking quarter by quarter and start looking at the full year.

Caitlyn pointed to something related: the calendar year itself might be the wrong container. Jenni had suggested in their breakout thinking about early winter and late winter rather than Q4 melding hard into Q1. "It was less of a hard line at the end of the year," Caitlyn said, "and I like that a lot more."

Your personal season and your business season are not the same thing

Ivy and Marie came out of their breakout with a key observation: there are natural cycles to the business calendar, and then there are your personal cycles, and they don't automatically align.

Ivy described how this time of year, as the sun moves into Cancer at the summer solstice, tends to pull her toward introversion and retreat. "Allowing ourselves to naturally have a quiet cycle when we need it helps us be more nourished and creative the rest of the time." She noted that when she gives herself a genuinely quiet summer, she returns more invigorated and energized for fall. "It's not about one's way of being in a cycle. It's about understanding how your personal cycle and your business cycle align or conflict. Just doing it consciously."

The mismatch between the two is where most of the friction lives. I mentioned in a previous workshop that some people told me summer is the busiest time in their business, and they hate it, and my response was: that might mean it's time to rethink your business model or your clientele. That's a harder conversation, but it's the real one, because when you work for yourself, the blessing and curse is that you have full control over your work; if things aren’t working, you have no one to blame but yourself. 

Excavate your patterns before you try to change them

One of the most useful reframes of the session was the word "excavate." Not design, not optimize, excavate. You have to go looking for your own patterns before you can build around them.

I shared that I've noticed I write almost the exact same blog post every January: antsy, cabin fever, ready to sell everything and start a flower farm. I do the same thing every June, when motivation dips. Jenni said the same is true for her April, when "all is lost, I will never have a business again." The point isn't that these feelings are wrong. It's that once you name them as a seasonal pattern, you stop treating them as a crisis. "It busts the shame of 'I'm doing it wrong,'" Jenni said. "We're actually right on target."

This year, I saw my July scarcity spiral coming and just named it. That's different from being inside it with no frame.

Carrie asked the practical question: how do people actually observe this stuff? Is it journaling? Note-taking?

The answer from all three of us was essentially: it depends, but you have to create the space for it.

Jenni described three layers. Daily, she does a red/yellow/green light check-in every morning: red means no capacity, yellow is moderate, green is full, with a corresponding list of what she does depending on the result. "Otherwise, I just assume I have green every day." On Sundays she sits down and assesses the week. And then there's what she called "the larger esoteric existential doubt portal," the bigger seasonal reflection that she tries not to force onto a calendar. She shared her full post on the red/yellow/green system in the Zoom chat.

Ivy built an entire planning system from scratch, rooted in planetary cycles, because she needed external accountability to follow her own process. She runs it as a membership offering partly to ensure she actually does it herself. "I feel like I run my entire business as an accountability trigger for myself."

Caitlyn takes a different approach: she books physical retreat locations three to six months in advance specifically so she can't move them. "If I don't do that, I will move them indefinitely, and they will never happen."

I move my quarterly reviews around constantly, as long as I keep them within the last month of the quarter. And the agenda shifts depending on where I’m at in all of my overlapping cycles. The space matters more to me than the date.

None of these is the right answer. Patsy named the through-line: "If you're not being intentional about it, and not making the space to take that reflection, if you're always just on the hamster wheel, you're not gonna get anywhere." Whatever gets you off the hamster wheel long enough to look at your patterns, use that.

"Balance" isn't a steady state. It's a pendulum.

Carrie surfaced something in her breakout with Jenni that the whole room ended up nodding at: the dance metaphor. Jenni had been talking about balance, and noted it doesn't really feel like a fixed thing; it's more like you swing past it, have a moment in it, and then go back. 

This matters because most planning systems are designed to achieve and maintain equilibrium. That's not how energy works, and it's not how businesses work. The goal isn't to stop swinging, it's to understand your arc.

Jenni put it cleanly: "Our nervous systems need something to push up against. We do that with routines. We're trying to anchor ourselves in a world that can be really unanchoring, but it really only can be seasonal. It's gonna change again in 8 to 12 weeks."

The intuitive and the structural aren't opposites

The session went somewhere unexpected toward the end, when Caitlyn noted she'd only recently learned I'm into astrology, after two years of working together, and said that if she'd known earlier, she probably would have written me off. What she observed instead was that I use it alongside structure and systems, not instead of them.

Jenni named this directly: "Magic is intentional action." She described herself as a former science journalist who now braids intuition, seasonal awareness, and strategy together, and attributed her biggest launches to intuitive timing with strategy placed on top. 

Ivy's version: she has a Circle Thrice official astrologer, and her consulting clients get quarterly astrology sessions as part of their work together. Because "what are the natural cycles going on in my life, and how do I feel about them?" is a genuinely useful planning question.

Anyone who came in skeptical left with something Caitlyn put well: "Bring in a little woo-woo, and then also have the practical side and make your left brain happy."

The through-line from everything we talked about is simple, even if the practice isn't: you can't plan a business you haven't actually looked at. The seasonal patterns are already there. The cycles are already running. The question is whether you're building around them intentionally or just surviving them and wondering why you're exhausted. That excavation looks different for everyone, but none of it works if you don't create the space for it first.

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