Freelance Friday: Structure & Secret Readers

Freelance Friday is my recurring feature where I answer your questions about the odd blend of blogging, journalism, and copywriting that is my career. You can read more writing-related content in my Blogging & Writing section!


Q. How do you structure your day so that you stay productive? I feel like if I worked from home, I would sleep until noon, procrastinate on my work constantly, and take terrible care of myself.

A. This is usually one of the first things people ask me about when they find out I work from home. Most people have some experience with aimless, unscheduled days – whether during a bout of unemployment, a gap year, or just a holiday – so they know it can be a mind-numbing and even despairing reality. So, they wonder, how do I, and others in my position, manage to do it every day?

It’s a fair question. When I first eased into the telecommuting lifestyle, I did exactly the type of shit you’re describing here. I slept too late, stayed up too late, skipped meals or overate, left work til the last minute or did too much all at once. I was like a teenager whose parents have gone away for a week in Bermuda. It was, shall we say, not ideal.

What I’ve found helpful isn’t glamorous or sexy: it’s just rituals and routines. I’m a Taurus through and through, so it takes me a while to warm up to changes in my daily habits, but once I do, they tend to stick. While I love the freedom and flexibility of the freelance life, I also recognize that I need to impose some rules on myself if I’m going to get anything done.

My dayjob, blessedly, requires me to get up around 9AM every weekday. I am a sleepy person and I have seasonal depression; if I didn’t have a reason to get up in the morning, I likely wouldn’t until late in the afternoon – so thanks, dayjob! I usually do an hour or two of that work before getting dressed and heading out to a nearby café to work on blog stuff, podcast stuff, journalism stuff, or more dayjob stuff – whatever needs doing that day.

Cafés are a crucial part of my workflow, and I’m certainly not the first freelancer to feel that way. Whether it’s the caffeine, the noise level, or just the impetus to put pants on and join the real world, there is something about cafés that helps me power through work that might’ve felt impossible if I was sitting at home in my pajamas.

Over the past year or so, I’ve become more methodical about taking a proper lunch break, rather than just working through it like a fiend. I’ll buy or make something filling, and settle in with a book/podcast/TV show/YouTube video while I eat. I found I was more prone to burnout back when I would half-work through my lunch, so now I force myself to get out of “work mode” for a while when mid-day hits.

My major not-so-secret secret weapon for productivity is a to-do list. I make one in my Notes app every day, and cross things off as they get done. My partner has access to the list, and his supervision makes this tool even more potent. It’s simple as hell, but keeping a to-do list religiously has boosted my productivity a lot.

Lastly, while it’s important to build structures that help me do my best work, it’s also important to build structures that let me relax at the end of the day. Freelancers and other self-employed types – especially those prone to hypomania! – are notorious for never really “clocking out,” and as necessary as that sometimes seems, it’s not healthy. When I’m done my work for the day, I close all my work-related tabs and apps, shut my laptop, and physically walk away from it. Often I’ll unwind by smoking some weed, reading a book, listening to a funny podcast, and/or writing in my journal. Then I’ll typically eat a late dinner and call my partner around 10–10:30PM. Our end-of-day phone conversations provide a grounding conclusion to my day, keeping me focused on something that isn’t my inbox or my Twitter timeline, which always feels so needed after a full day of work.


Q. Has anyone you weren’t “out” to as a sex writer ever found your blog and confronted you? How did you handle that?

A. While I wasn’t always “out” as a sex writer, I’ve never really been embarrassed when someone read my writing who “wasn’t supposed to.” I always figure that if they’re offended by it, that’s on them, not me.

Of course, that isn’t true in every case. If I was writing cruelly or nonconsensually about someone, it would be reasonable for them to get upset about that. I’ve definitely done this in the past, but I’ve learned from my mistakes. Nowadays, usually the only people I roast on my blog without their express knowledge are people who’ve deeply hurt me – people who genuinely fucked up in some way. Anne Lamott says, “You own everything that happened to you… If people wanted you to write warmly about them, they should have behaved better,” and I believe that, to some extent. Someone who dumps me in a coldhearted way, or ghosts me, or leaks nudes of people I love, knows they’re being a dick when they do that, so I have few qualms about lampooning these people on my site – which they probably don’t even read, anyway.

The caveat is that I’m never unnecessarily cruel and I never identify people who don’t want to be identified. I wouldn’t write mean shit about a Tinder hookup’s dick size for no reason; I wouldn’t publicize an ex’s name, or describe their appearance in overly specific detail; I wouldn’t spill other people’s secrets or their deepest shames. It’s just not nice. I’m not saying I was always perfect on this front, but these are the standards I hold myself to now.

That said – yes, there have been times when I’ve discovered someone was reading my blog who I wish wouldn’t. For example: a dude who had, months earlier, lied and told me he was poly when he was actually monogamous, thereby making me unknowingly complicit in him cheating on his girlfriend. Or an ex who’d broken up with me in an especially explosive and scary way. Or a guy I’d stopped talking to after he crossed numerous boundaries. While I don’t necessarily begrudge these people reading my site, it is weird when they tell me they read it, especially if they do so as part of a half-assed apology or an unwarranted desire to “reconnect.” It feels like a boundary violation. If you are reading this post knowing full well that I probably wouldn’t want you to be here… perhaps think a little about why you’re doing that, what you’re getting out of it, and how it might make me feel if I knew.

I’ve been much better about getting partners’ consent to write about them and running relevant details by them before publishing, ever since a boyfriend told me, during a breakup, that I’d made him feel used for material. Those consent practices are important, but it’s also important for me to be able to write about shitty behavior when people are shitty to me. It grinds my gears when a partner or a hookup does something reprehensible and then says, “Don’t write about that on your blog” – because the implication is that they want to appear good and sweet to my readers, without actually being good and sweet to me. Fuck that. If they wanted me to write warmly about them, they indeed should have behaved better.


If you have questions for this series, you can leave them in a comment below, or email them to me!