Making the Most of My Time (Most of the Time)

During a recent conversation with a connection on Twitter about time management, I received an interesting reply: “I wish more freelancers would talk about this!”

After exchange messages with this person, I realized that others might find a shred of value in hearing my approach. Here are my thoughts on how to manage my time as a full-time freelancer (which I have been doing for about six months now), coupled with how I also made things work as a part-time freelancer (which I did from mid-2015 until roughly the end of 2018).

*** CAVEATS: I’m married, in a household with no children and two wage earners, and I’m covered by my wife’s health insurance. This grants me substantial privilege in developing my schedule and taking on work, which I recognize many of you may not have. I have done my best to present this advice while being sensitive to challenges that you may face but I do not. ***

Break the day into chunks. When I have several projects on my plate at a time, I try to organize my day into 90- to 120-minute blocks. That way I’m able to focus on 3-6 different tasks in a given day. If all goes well, it means I don’t have to scramble and spend several hours on a piece the day that it’s due. (Yes, I was in fact That Kid in school.)

Depending on the time of day or the status of a project, the work done in this block could be outreach to potential sources, secondary research, writing, or a final edit. Sometimes I set aside a block of time for general administrative what-have-you, which can include outreach as well as invoicing, doing my taxes, trying to fix my printer, and so on.

Write when the brain is ready. I’m a much more productive writer in the afternoon and early evening, especially for anything that’s rather technical or research-driven. Other freelancers prefer to do their writing in the morning, to get it out of the way, or as they sit down to have lunch. If you’re able, I suggest trying to write when your mind and body are most up to the task.

Do the easy stuff first. Since I don’t tend to do my best writing first thing in the morning, I focus on other tasks if at all possible. Sometimes it’s reading and research. Sometimes it’s interviews and meetings. Sometimes it actually is writing, but it’s not stuff that requires a lot of deep analytical thought.

For example, one recent project involved writing profiles. The vast majority of the work involved straightforward secondary research and plugging sentences into a pre-formatted template. This was a great task to do for 90 minutes while I sipped my morning coffee and got my brain working.

Take a break when focus fades. Between 2 and 3 p.m. every day, I start to lose focus, no matter what I’m working on. In a 9-to-5 desk job, there’s a temptation to try to power through – but in making my own schedule, I use this time to step away from my desk from a bit.

If you find yourself losing focus around the same time every day, and you have flexibility in your schedule, try to do something else. In my case, I usually go running in the middle of the afternoon, or if it’s an off day I may get a head start on dinner. The key, I find, is to do something you like to do, as opposed to something you have to do, like laundry or dishes. Yes, it’s nice to get those chores done, but if your intention is to take a break, and you just replace one work-like task for another, then it’s not really a break.

Set concrete boundaries. For me, this is less about when the work day begins, pauses, and ends. It’s more about when or whether to extend the work day or week. In past lives, I’ve gone to grad school and written a thesis at night, and I’ve worked a second job with morning, night, or weekend shifts. From my late teens into my mid-30s, the beginning and the end of the work day / week was always a bit blurry.

Now that I’m able to work only one “job,” I value my nights and weekends. If I have to do work outside the bounds of the typical work day, these are my preferences (in order):

  1. Get up early and start before breakfast. Might as well get it over with, right?
  2. Work past 5, but stop for dinner. That way, there’s a clear end to the day.
  3. Work until 5, stop for dinner, and then resume after dinner. This is if I know that the project I need to finish will take a couple hours.
  4. Work on the weekend. I only do this for a couple hours at a time, for a single project, and as a way to get ahead. If I need to catch up, I save it for Monday.

Note: I have done this maybe 5 times in the last 6 months. This is by no means a habit, nor am I suggesting that you make it one. Instead, I’m suggesting that it’s worth thinking about how you’d prefer to tweak your schedule when you have more work to do. That way, when it does happen, you can anticipate the impact to your schedule, plan accordingly, and avoid preventable stress.

Build time for prospecting. It can be hard to do what amounts to unpaid work, but it’s important to build time into your routine for actively looking for new work. Even if things are going well, you should at the very least be making a list of the publications, institutions, or clients for whom you’d like to work. I keep a running list, and when I have free time that isn’t on a Friday afternoon I’ll send some inquiries or follow-ups.

For some people, this is a process that happens organically; the list grows as they read the news or social media and find something of interest and plunk it in a working document. Other people may prefer to devote a couple hours at a time to doing the research and finding contacts, so it’s a more formal part of the work schedule. Whatever you prefer, just make sure you keep it up.

Naturally, these are general rules of thumb and aren’t written in stone. Right now, for example, it’s closing in on 3 p.m. and I’m writing instead of running. Lately I’ve also been more likely to work past 5 p.m. than before 9 a.m. — in large part to mirror my wife’s schedule, which is much less flexible. And at the end of this week the “chunks” of the day were more like 3-4 hours instead of 90 minutes.

That said, I’ve found that having some general guidelines for when and how I work has made it easier to maintain my focus when I have a lot to do. This ensures that I’m organized instead of overwhelmed, and it leaves me time to do the things outside of work that need to be done – whether it’s running, folding laundry, or spending quality time with my wife. If you haven’t yet created some guidelines for how to manage your time as a freelancer, I encourage you to do so.

Reflecting on the Power of Language – Or, “Am I Making Myself Clear?”

I’ve been thinking a lot recently about words and, more broadly, language. (More so than usual, that is.) Part of this stems from the way current events and historical context have been discussed. Part of it comes from wrapping up a contract gig as a writer and editor for a healthcare IT consulting firm, where I learned that the combination of healthcare IT jargon and consultant-speak can be quite the word salad. All of it, I think, is related.

One key goal of writing, regardless of genre, is to establish credibility and authority with your audience. There are typically two ways to do this.

One is simplicity – breaking a topic down into words, phrases, and sentences that a general audience can understand. It’s the “Can you explain this to your parents?” principle. It’s a cornerstone of good journalism, approachable nonfiction, and relatable marketing.

The other method, conversely, is obscurity – discussing a topic in a convoluted way to elevate the author’s expertise above that of the reader. This isn’t necessarily about using big words and lots of semicolons, though that doesn’t necessarily help. It’s about writing in a way that makes a general audience feel excluded.

I’ve seen this happen in three key ways. They seem similar but have nuanced differences.

The first is sticking to language that’s meant for a niche audience when your goal is to inform a larger audience. This happens frequently in the trade press, where the assumption is that the audience “just knows” what the alphabet soup of acronyms and abbreviations means. (I have been guilty of this.) Character limits on social media posts and in headlines certainly don’t help. This can reflect that a seasoned writer knows their stuff, which is certainly helpful for covering complex topics. However, it also conveys a level of insider status that separates the writer and the audience.

The second is declining to modify language that was written with a specific intention in mind. Think about the times you’ve seen language lifted from a press release, police report, earnings statement, or research paper and plunked, unedited, into a news report. The ethical ramifications of this practice notwithstanding, this suggests that an author and their editors have left it up to the reader to define a non-compliant patient, a digital therapeutic, a payvider, and so on. Those words are made-up at best and loaded at worst, and it’s the job of the writer and editor to explain what they mean (or just avoid them altogether). Just because a source said it doesn’t mean it needs to be restated verbatim.

The third is neglecting to explain, or outright excluding, meaningful information. As a local news reporter, I had to provide context in every story, even if I was covering the proposed housing development for the 45th time and was sick of writing the same details over and over again. When those details are omitted – the location, the number of units, the name of the developer, etc. – you imply, “You don’t know? Well, you should have been paying attention all this time.”

As we write, we need to avoid obscurity. (Or, as Dennis Miller said in his short-lived stint as a football announcer, eschew obfuscation.) The last several months have taught us that accurate, meaningful, and relevant information – about what happened in the past, how that is affecting what is currently happening, and how that will drive what needs to happen – is both deeply valuable and difficult to find. I’m committing to making my writing clearer, and I hope that you do the same.