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Managing the chaos of freelancing by taking control of your schedule

by Geoff Hart

Previously published as: Hart, G. 2008. Managing the chaos of freelancing by taking control of your schedule. <>

As freelancers, we all face the problem of feast or famine: sometimes we're overwhelmed with work, and can hardly find time to think, let alone keep up with our other responsibilities, but other times dust gathers on our computers while we wait for new work to arrive. Clearly, marketing our services and finding new clients is important to avoid the "famine" part of the freelance lifestyle, but what do you do when too much work is arriving?

As a freelance editor, my work primarily involves a large number of small jobs rather than a small number of large projects over the course of the year. In this article, I'll use this situation, which many other freelancers are familiar with, to provide some suggestions on how to manage your work schedule more effectively and attain a slightly more sane work life. The advice I'll provide is equally suitable for freelancers who work on a few large projects, since even the largest projects can be broken down into smaller and more manageable chunks. (Indeed, the really big projects can't be managed any other way.) The same strategies apply, but with an obvious modification: you'll need to budget time at the end for cleaning up and finalizing the whole project.

There's no foolproof solution to the chaos of freelancing, since life sometimes happens all at once and there's nothing whatsoever we can do about it. But there are several tricks that let us juggle life and work considerably better than if we give up and simply accept whatever life throws at us. One of the first and most powerful solutions involves gaining more control over our schedules. Doing so requires only four simple steps:

Learn how much work you can complete per day

Tracking your productivity is important, because it's the only way you'll ever be able to know how long a job will take and thus, how many days you'll need to reserve for a given job. This knowledge is what lets you schedule your work. Each job is at least slightly different from the work you've done previously, but over time, you'll gradually get a feel for your range of productivities, including both your long-term average and the worst-case scenario. A conservative approach to scheduling your work relies on using the worst-case productivity, since that way you can be reasonably confident you'll finish ahead of schedule. Basing your schedule on your average productivity may be more realistic in the long run, but it also means that you'll end up working under significant deadline pressure for half of your jobs and severe deadline pressure for a significant number of jobs.

If you track productivity separately for each client or each type of product, you can further refine your estimates. Best of all, if you get a chance to examine the whole job (e.g., the full text of a manuscript to be edited or a carefully defined functional specification for software) before you are asked to provide a quotation, you can base your estimate on the actual work you'll be doing and come up with a much better estimate for that specific job. However, there's a common gotcha to be aware of: early chapters in a book that you'll be editing or the initial product features you'll be documenting in a help system tend to have been developed early in the project, while the author or developer was still well-rested, excited by the project, and not facing insane deadlines. Later parts of the job often take longer than early parts because of creative fatigue, loss of interest, or simple lack of time to do the job right. So try to examine the whole project, not just one or two initial components, before you create an estimate.

The first step to gaining control of your work life is to learn the trick of estimating how long a job is going to take each time a client contacts you with more work. For suggestions on simple ways to track your productivity, I've provided two resources on my Web site:

Use some form of calendar to reserve dates

Once you know how long a job will take, the next step is to schedule the work. Doing so requires some form of calendar, whether you implement it on paper or in software. (Different strokes for different folks!) Basically, your goal is to recognize that there are only so many working hours in a week, and that all your work must be fitted into those available time slots. Once a slot is full, it's no longer available for other work, and finding a way to account for this in your schedule is the key to regulating your workflow better.

In the previous step, I asked you to determine how much time a job will take. Now your goal is to look at your calendar and find the first day when you can begin that work. Mark the day (or days) on your calendar as "Reserved for [name of job]" so you won't double-book those days for other work. One of the biggest mistakes freelancers make is failing to reserve dates for future work on those rare and happy occasions when a client gives us advance warning about when a job will arrive. If you have clients that predictably send you work such as annual reports, quarterly newsletters, or annual funding proposals at specific times of year, reserve those days each time you start marking up your calendar for a new year, and add a note in your reminders program a month before these periods so you can contact your client and confirm whether the work will arrive on schedule.

Don't forget to include down-time and other non-work time commitments that will reduce the number of hours available for work. If you know you'll be away or unavailable for part of a day, mark that part of the calendar as unavailable. Include doctor appointments, family gatherings, meetings, or anything else that will prevent you from working. Don't neglect the obvious: for example, my first calendars were clearly marked "no work today, idiot!" on weekends and holidays because early in my freelance career, I was constantly working through the weekend and wondering why. As it happened, I'd simply neglected to block in those days as unavailable for work. (Sometimes I'm thick as a brick.)

Reserve all your known commitments (e.g., an hour a day for exercise or watching your favorite TV show) before you start allocating your time for the coming month. You won't always be able to honor every commitment, but you've got a much better chance of success if you're at least willing to try to give your real life equal priority to your work life. For longer allocations of time, such as vacations, add a note in your reminders program to notify all your main clients well in advance so they can plan around your schedule. (Many won't bother, but each one that does is one less client likely to cause problems around that time.) One useful, though mildly unethical, approach involves telling clients you're leaving a couple days earlier than you really are leaving. This way, if any emergencies arrive at the last minute, you still have time to handle them—or to find someone else who can do so. (More on the latter topic in the penultimate section of this article.)

Paper works adequately for calendars, but software solutions provide far more flexibility when it comes to rearranging your schedule. What software should you use? Options range from behemoths such as Microsoft Project to smaller and nimbler tools such as the task and calendar tools built into Microsoft's Outlook or Apple's iCal. Everyone eventually finds an approach that suits their unique needs, and the key is to invest some time experimenting until you find an approach that works well for you. For example, I've found an approach that, though kludgy and inelegant, works better for me than more complex and powerful solutions: I use iCal for reminders and small notes, but I use nested folders on my computer's desktop to organize my work life. You can see what this approach looks like in Figure 1. The key concept behind my approach is that I use a single "Work" folder to gather all my work together in one place, and use Macintosh aliases ("shortcuts" in Windows) that point to the actual folders that hold the work for each project. Adding the date at the start of each folder name lets me schedule the work.

Figure 1. Using nested folders to organize your work schedule.

Each month, I create a new series of named folders to reserve non-work days for weekends, holidays, and other times I won't be available for work. For a weekend, a typical folder might be named "September 12-14 no work". (Note that I've also marked most Fridays as unavailable for work. We'll come back to that point in the next section.) Similarly, the screenshot shows a planned absence in the form of a working vacation during which I'll be giving a workshop to a local STC chapter and then taking a few days of vacation: "October 12-20 no work (Phoenix trip)". Folders representing dates when I'm not available for work are highlighted in red to distinguish them from folders representing work.

In the screenshot, you'll see two different types of work folder: Folders such as "September 8--808078 Harada alias" represent a project I've already received and that is ready for editing when time permits, but no later than that date, whereas the folder "September 9--808061 Harashima (long review)" is a placeholder for a job that hasn't yet arrived but that is due to arrive on the specified date. I'll replace that one with an alias to the real folder once the files are on my hard disk. Folders that contain the word "alias" (the Macintosh version of Windows shortcuts) point to the actual working directory, thereby providing direct access to that directory without having to click my way several levels deep into my hard drive. This is important for me because I have clients in dozens of countries, and several large clients in two countries, requiring a strongly nested folder hierarchy on my hard drive.

Note that I've also used a yellow-highlighted folder that does nothing but separate ongoing tasks (such as the newsletter that I publish for STC's Scientific Communication SIG and a list of presentations I'm currently working on) from the actual paying work. Because most operating systems sort names beginning with a hyphen before names beginning with letters, adding a hyphen to the names moves these folders to the top of the list. Other useful tricks such as adding a number before each name lets you take advantage of the operating system's default ordering rules.

The resulting display provides an "at a glance" list of the work that needs to be done, and when it needs to be completed. Using a consistent naming scheme lets me use the built-in display options on my computer to place the work in correct order, but there's an obvious problem: although the order of the folders is correct within any given month, you can see that my absence in October displays above (before) the work that must be completed in September. I could solve this problem by working in icon view instead of text view, since that would let me manually drag the folders into the correct order rather than being constrained by the operating system's sorting preferences. I've found that I prefer the text view, and can live with the tradeoffs.

When I finish a job, I simply delete the alias pointing towards it, which has no effect on the actual folder that contains the project, and move on to the next project on the list. When new work arrives, I can see at a glance when I'll be able to fit it into my schedule, and I can immediately propose that deadline to the client. If urgent work arrives, with a tight deadline, I can see (based on the dates in the work folder) which projects can be pushed back a day or two. For example, the folder "September 9 (due 18) 808062 Wada alias" tells me that I should try to get the job done by the 9th, but that I can let it slip by up to 9 days if more urgent work arrives unexpectedly. In the next two sections, I'll discuss how to handle such surprises.

Always build some slack time into the schedule

When a client contacts you to discuss new work, learn to always ask them two questions:

Most of the time, there's a significant gap between the two. When you record the job on your calendar, carefully record both dates. If unexpected or more urgent work arrives, knowing the true deadline provides an opportunity to juggle your schedule (i.e., push back the date on a less-urgent job) so you can fit in the new work.

This approach is a specific example of a more general principle: always build in a day or two per week of empty time that you can use when a job takes longer than expected or something urgent arrives. The more flexible the schedules of your clients and the more predictable your workflow, the less empty space you'll need to set aside. Over time, you'll gradually get a feel for how much work is likely to arrive in a typical week. For example, my major client typically sends me two to three jobs per week, and more than that during busy periods. Knowing this, I no longer accept more than two or three jobs from other clients in any given week because doing so might leave me unavailable to that primary client. If my major client is less busy than usual, it's easy for me to complete other work earlier than originally scheduled or accept work I'd otherwise have to decline, thus giving my other clients a pleasant surprise.

Of course, whether to do work earlier than scheduled is a bit of a judgment call. If you're as busy as I am, you'll find that it's a wise choice, because you never know for sure what will arrive on your desk next week, and freeing up time now by finishing next week's work early makes it less likely that you'll have to turn away work or pull an all-nighter. On the other hand, sometimes you simply need a day off to decompress, and the risk of longer work days next week isn't the worst alternative.

As I noted in the previous section, I've implemented my own advice by marking my Fridays as unavailable for work. This serves two purposes. First, I'm growing sufficiently old and prosperous that free time is becoming more valuable to me than a few extra dollars. During slow periods, this means that I can often take a 3-day weekend and use the extra time to work on my own writing. Second, this automatically gives me one day per week of flex time that I can allocate to rush jobs or unexpectedly long jobs that require more time than I budgeted. I still often end up working most Fridays, particularly when I know that I'll be leaving for a long trip and need to store away a bit of extra money to cover my lack of earnings during that period, but asking clients when they really need a job returned often lets me defer a job until the following week. Then, if I do need to work on a Friday, or if I know something big is coming the following week, I use the extra hours on Friday to avoid a serious work crunch the following week.

Develop a support system

All of this is great in theory, but in practice, sometimes everything hits the fan simultaneously and there's simply too much work for any one mortal to handle. Pulling an all-nighter or working a 60-hour week is sometimes possible, but it's not a good long-term survival strategy, even if you're young enough to survive what programmers glibly refer to as a "death march". (I no longer am.) Yet there's always the fear that if you turn away a client because you're too busy, they'll never come back to you. Fortunately, there's a reasonably effective solution.

That solution involves finding one or more colleagues you can trust to do work that's up to your personal standards and who also won't steal your clients. Yes, such people exist; I'm one of them. In those periods when you have some downtime, spend some time finding two or more colleagues who are willing to do this kind of work and who you can trust. Discuss the possibility of covering for each other during rush periods, with an explicit but informal verbal agreement that you won't steal each other's clients. (You can also make this a formal legal contract if you want more reassurance, but starting your relationship by making it clear that you don't trust your colleague without a signed contract is not an auspicious beginning.) You may still lose an occasional client this way, but if you choose wisely, an ethical colleague won't steal your clients and everyone will sleep a bit easier knowing they have someone to cover for them. Better still, an insanely busy period for one of your colleagues may coincide with a slow period for you. If you hit a dry spell, write to these colleagues and let them know. They may be happy to send you some of their work.

I work this way and refer potential clients to a few colleagues purely as a friendly gesture: I don't charge them any money for this service, and I don't count up their debts to me. I've been blessed with more than enough work, and have several colleagues who aren't so fortunate and who could use a few extra billable hours. The benefit of this approach to me is that I'm not responsible for the quality of their work, and I make this quite clear to the clients when I give them the referral: "Here's someone who can handle this work for you. I will not be supervising their work, but they've been doing this work long enough that you can feel confident in their expertise." If you're more entrepreneurial than I am, you can also subcontract such jobs, and then do quality control on the subcontractor's work to ensure that it's up to your standards. Personally, I find this way too much overhead, but it might be a very good solution for you, particularly if you're still building your client list and need a bit of extra income.

Parting thoughts

I started this article by noting that this approach can be modified to cover a range of other situations. For example, what can you do if you receive offers for two large projects that must be worked on simultaneously? Typical examples might be when two publishers ask you to edit large textbooks simultaneously, or when a software developer asks you to document two large modules of a larger program at the same time. Although it's clearly more efficient to focus on one project at a time, it's often appropriate to budget half your work week for each project, and switch horses every Wednesday at noon. Each job will take roughly twice as long as if you worked on only one project at a time, but if you designed your initial scheduling estimates to account for this situation when you accepted the work, you'll often still be able to complete both jobs on schedule. This is particularly true for software documentation early in the development process, when many parts of the software are being delayed or constantly revised, and you may not have enough work to devote a full week to the product. Things become dicier towards the end of the job, as the software begins to stabilize, more features are complete, and deadlines tighten, but it's unusual for this to happen at exactly the same time for projects from different clients. More often, different parts of each project progress at different rates, and a slow period for one project will overlap a work crunch for the other project; in that case, you can adjust your schedule to fit in more of the crunch project and less of the slower project. This can also happen with large books, particularly when multiple authors are contributing chapters over a period of several months.

For this approach to work, you need to discover factors that might impose the same deadline or a non-negotiable deadline on two large projects. In software documentation, this might happen when two programs must be released at the same trade fair, such as INTEROP or in time for the annual tax preparation season. For books, you might need to complete a project sufficiently far in advance that the book will be available at the start of the school year, in time for the Christmas book-buying season, or a big annual book fair. The only way to discover such pressures is to ask your clients whether any such factors might affect their delivery schedule for the product. (Note that I said their schedule, not your schedule. Clients can sometimes be amazingly clueless about how your schedule relates to their schedule, leading to unpleasant surprises.) For some additional tips on learning about organizational schedules, consult the "survival skills" part of my article on Improving your editing efficiency.

Learning to schedule your life more sanely also has strong ties to what may be your most crucial task as a freelancer: establishing a slush fund to cover your expenses those times when the work stops flowing or illness prevents you from working. (This also helps you to afford periodic vacations.) This isn't optional if you freelance: make it a priority to build up 3 to 6 months worth of savings that you can tap during slow periods or illnesses, even if it means giving up beer and movies for a couple of months to save that money. If you have a family to support, consider buying disability insurance to cover you against illnesses; other forms of income-replacement insurance may be available, so ask an insurance broker about your options. Knowing that your slush fund is full lets you sacrifice work on the occasional Friday, whereas knowing that it's underfunded or that you'll be drawing it down soon (e.g., to pay a quarterly tax installment) reminds you to work longer weeks. For some tips on this, see my article Tax tip: a personal savings plan that works.

The freelance life isn't always predictable, and is sometimes unpredictable in a very stressful way. But the first step in mitigating that stress is to take steps to gain some control over your schedule. This article covers a few basic strategies you can use to improve your control. Your own work situation will clearly differ from mine, requiring various modifications to the approach I've proposed, and there are other stresses I haven't covered that require different solutions. But as this article shows, the important thing is to decide that you're willing to devote a little time to developing strategies that will minimize those stresses—and these strategies don't need to be particularly complicated. Such simple steps can take you a long way towards a more enjoyable freelance career.

©2004–2018 Geoffrey Hart. All rights reserved