The Other Work: What it Means to Work ON a Freelance Business

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.

There's no shortage of advice telling freelancers to work on their business, not just in it. What's missing is any agreement on what that actually means, or any real conversation about why it's so hard to make happen. I asked everyone who registered for this forum what working on their business meant to them, and got a different answer from every single person. So that's what we dug into: what this work actually looks like, why freelancers aren't giving themselves credit for the version they're already doing, how it changes depending on where you are in your business, and what makes it possible to protect consistently.

Working on shows up in different ways 

A few distinct categories kept showing up when we unpacked what working on your business meant. 

• Strategy and direction: where is this actually going, do I still like it, what's the plan?
• Marketing and visibility: doing the work of getting known, building an audience, staying in front of the right people.
• Systems and operations: building the processes that make the day-to-day go faster and smoother. 
• Reflection and evaluation: stepping back to examine what's working and what isn't. 
• And an emotional layer underneath all of it: how does this business reflect who I am, and is it still doing that?

None of these is more legitimate than the others. 

Reuben Swartz offered a useful way to gut-check where your attention should go: "If I came and took over this business tomorrow or right now, what would I tell the person running the business to do, versus what am I actually doing?" That gap is the work. 

Caitlyn Tivy's version is more about energy: she keeps the administrative tasks separate from the bigger-picture thinking time, not because one counts more, but because mixing them changes how the time feels. "When I reframed it away from specific tasks and more from how are the vibes in my business right now," she said, "it made it a lot more pleasant to think about." 

The category that resonates most tends to depend on where you are and what your business actually needs right now.

What this work looks like at different stages of your business

Working on your business means something different depending on where you are. In the early years, it's mostly about the basics: building the client list, following up consistently, and not letting the feast-or-famine cycle eat you alive. As Maari Casey put it, "one of the first things that happens when you start a business is you get really busy, and then you don't get any new business." Staying out of that hole is itself a form of strategic work.

Further along, the focus shifts. You've got the basics running, but you're executing the same playbook on repeat and potentially missing what's changing around you: market shifts, new opportunities, threats you haven't squared up to yet. "Sometimes we have a tendency to do our same stuff over and over again," Maari said, "and we're missing opportunities." The "on" work at that stage is less about survival and more about intentional direction.

You're probably already doing more of it than you're giving yourself credit for

A lot of freelancers genuinely don't feel like they do this, and part of the reason is that the mental model for what counts is too narrow. It's not just the two-day retreat. It's the walk, the shower thought, the conversation with a peer where you suddenly realize what you actually need to do.

Lizzie Davey put it well: she spends a lot of time each week with freelance friends in cafés, co-working spaces, and the pub, talking through their businesses. She hadn't been counting that. "I think that's a lot of what I do every week," she said, "and it probably very much feeds into the more scheduled strategic work I do quarterly." 

There's also a structural reason this feels harder than it should be, especially if you bill hourly. Every non-billable hour has a visible cost. Part of making room for this work is building the overhead into your pricing in the first place, so stepping back doesn't feel like bleeding money every time you do it.

Structure matters more than frequency

The question of how much time to carve out for this (10%? 20%? One day a month?) doesn't have a clean answer, and I don't think it should. What came through clearly is that the specific structure matters less than the commitment mechanism behind it.

Caitlyn has built a cadence that works well for her: quarterly retreats (usually two and a half days, often at an Airbnb even close to home, because the physical separation does something) for the big-picture thinking, and monthly "mini-retreats" to execute on what she planned. "My quarterlies are very strategic and broad," she said. "My monthlies are to actually get a big project done, or write that email sequence I've been meaning to write." The reason it works is that she pays for it in advance and puts it on the calendar. The commitment is the thing.

My own version is more seasonal; I tend to build those concentrated pockets of time at natural inflection points in the year, when the rhythm of my work and life already creates a little space. There's no single right answer on cadence. But without any structure at all, it will always lose to client work.

Knowing what you won't do is its own kind of strategic work

One of the moments I'll be thinking about for a while came from Ivy, who shared the idea of a "don't-do list" as something she keeps alongside a to-do list. The work you won't take on. The clients you won't chase. The tactics that don't actually help you. "What you say no to," she said, "makes room for what you say yes to."

Building that list isn't a passive exercise. It requires you to have actually examined your business, which means the process of making it is itself working on your business. And once it exists, it becomes one of those litmus tests you can use to make decisions faster, with less second-guessing, because you've already done the thinking.

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