I struggle with planning my freelance business: with collecting and analyzing my time-tracking data and my website analytics, with reflecting on the clients and projects I enjoyed and those I didn’t, with knowing when my calendar is fully booked and when I need to push on my marketing.
I can imagine what the process of planning might look like. I’d set a goal — say, to attract X number of new clients in the coming year — and then set out the marketing strategies, map them onto my calendar, implement them, measure their efficacy and iteratively develop them.
Yet despite understanding the process, and despite being an excellent planner in my personal life — I’ve been known to buy train tickets seven months in advance — I simply don’t do long-term business planning. I scarcely do weekly planning, because every system I’ve ever tried, digital or analog, has failed me (or I’ve failed it, or we’ve failed each other). I mostly run my calendar on the most Millennial Generation of strategies: vibes.
To learn more about how my fellow freelance editors conduct their annual planning, and to see if any of my colleagues have non-vibe-based strategies I might attempt adopting, I asked some edibuddies about their approaches.
The answers I received from my colleagues fell into three categories.
Annual planning schedule
Lesson learned: The folks who can plan, do — and they integrate reflection and allow for imperfection and change.
Kellie M. Hultgren: I take off the last week of the year to tie up administrative loose ends (mostly tidying up my financial records); compile information on clients, rates, and such; and get a head start on tax prep.
I typically pull as much data as possible out of my accounting system (Wave) and my time tracker (Toggl) and throw it into a spreadsheet to generate metrics about per-hour and per-project rates. It’s not the cleanest data, due to things like inconsistent tagging of time between billable and nonbillable work, but it’s enough to show which clients are underperformers.
I also use reflection tools, such as YearCompass (general) or Liminal Pages’ Yearly Reflections (editor-specific), to gather information about how the work felt over the year. This is how I get myself to admit that Client X pays well but stresses me out, while Client Y pays less but brings me joy.
Then I get tired and walk away from it for a couple of weeks. By that point I usually need some yearly goals for my very patient mastermind group, so I use my notes to make some. I do pretty well with goals like “Say no to this particular red flag” and “Adjust website to prioritize this kind of work,” but “Get five new clients by June” doesn’t work for me because it’s not in my control.
Eliot West: I do often set, articulate and commit to a big-picture work-life intention for a period of time; this has ranged from a week to five years, though. For example, heading into 2023, I decided to prioritize efforts toward visibility and credibility, giving myself permission to try things without scolding myself for wasting time on unpaid work, putting myself through unnecessary work and so on. Then I had an enormous personal loss and experienced a lot of that in such deep grief that I don’t remember all of it?
For 2024, I oriented myself toward healing, which needed to look like giving myself a break without becoming invisible. I needed to lean into being gentler with myself and my nervous system without losing existing career progress, because I continued to want to work.
Quarterly planning schedule
Lesson learned: for many, quarterly or even monthly planning makes more sense than annual planning — and it can take many forms.
Sheila Loesch: In the past, I always felt devastated if what I’d intended for a year didn’t pan out. So what I do instead is quarterly planning. I started this in 2023, and it’s been a lot more achievable and meaningful for me. The shorter quarterly approach has allowed me to view things differently: if something didn’t work last quarter, I can either try something new for the next one, or I can keep doing what did work.
Also, I find my energy levels, excitement about work and emotions can vary drastically across the four different seasons I experience where I live. It’s been subtle, but shifting to quarterly planning has helped me think about what I’m feeling in the present and account for how that might affect me and my work in the coming three months.
I don’t have a template yet, as it’s been very casual. For right now, I keep a digital note, accessible on my phone and computer, where I write the current quarter’s goals, and then possibly draft some for the next one.
Barbie Halaby: I try to do mini solo business retreats quarterly. During these, I look at my hours worked, clients, income, etc. and decide if I’m happy with them. I usually set aside time for some continuing professional development as well. The metrics I use to rate my clients are:
- Pay rate
- Reliability
- Enjoyability
- Ease of work
- Meaningfulness
I rate them 1 to 5 on each metric, come up with a total and a brief reason, then rank them highest to lowest. I then determine what comes next: pursue more, maintain, negotiate, or “drop ’em like they’re hot.” This helped me figure out that I wanted more indie fiction and memoir and no more indie non-fiction, as well as which university presses I should accept more from and which I should save for when I am desperate.
No set planning schedule
Lesson learned: some folks, like me, don’t plan or don’t yet plan — and that’s cool too.
Ayesha Chari: Like many freelancers, I’m a brilliant planner but do no annual business planning. It’s hard, in my work, to feel a sense of agency for measurable things. The last few years I’ve been trying to be more deliberate in my business, hoping that that will make it sustainable in the long term, as I don’t want to stop working if I can help it.
I’ve done that by committing to loose intentions such as growing confident about all things business and caring for myself (the latter is spectacularly hard for me, made more complicated by sociocultural baggage). I’d like to continue setting intentions, as it feels more natural than creating clearly defined goals. Having said that, in the new year, I’d like more money (!), a few new clients and powerful research projects. And less FOMO and guilt generally.
Lindsay Hobbs: I don’t do annual planning. My client list has grown this past year, and I’m hoping to grow it further in 2025, but I don’t have any sort of predictability to when work comes my way. It has been more or less working out — sometimes I start to freak out when nothing is lined up, and then something lands in my inbox. I have no idea how to plan in this situation, but organically filling my calendar also leaves room for flexibility.
Tina Emmerich: I used to make plans in my head. Like “Have website up by September,” “do a self-paced lesson a week” (lol) or “write a blog post a month” (double lol). And then I’d forget — and then I’d remember — and then I’d feel stressed because I hadn’t done anything yet. I used to write things down in a notebook — only to forget to look into my notebook! What I’m trying now is a small whiteboard in plain sight where I write down a small list of goals. (And a reminder to look into my notebook.)
Reflection
As for me, I still haven’t figured out what my annual planning will look like in 2025. Ultimately, what I think I want is something measurable that maps client work to the calendar, ensures a steady income stream, allows time for writing and teaching and accounts for my long-term vision for my business … but is also inspirational, creative and engaging to the senses. Ideally it would also somehow be embodied.
What I think I’m saying is that I want an annual plan in a spreadsheet that is linked to a calendar but is also an interpretive dance. I’ll keep working on that process. Until I figure that out, I’ll continue with the vibes.
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