Remotely Helpful, Part 2: Locations & Logistics

Here’s part 2 of my 3-part series on working from home! I’ve got some more tips for you today…

#4: Mix up your location from time to time.

I know in my last post I proselytized the joys of having a functional at-home workspace, and that’s still important, but I nonetheless can’t imagine always writing at my desk at home. Eventually I always get bored and/or lose motivation. That’s when I know I need to shake up my location.

Coffee shops and libraries are great for this, and are staples for many writers – for actual scientifically-backed reasons, in some cases! If you know of a bar that’s chill about people bringing their laptops, that’s nice too (Northwood early on a weeknight is my Platonic ideal of a relaxed writing spot). I’ve known writers who loved to write in mall food courts, public parks, or subway trains. Just make sure that if you go somewhere with no WiFi (or with dicey WiFi), you prepare in advance any research materials you’ll need, so your work won’t be stymied by the lack of connectivity.

Of course, co-working spaces are also an option, but most freelancers I know don’t make enough money to be able to justify the expense. (For example, the Toronto Writers’ Centre charges $135/month, and Lemonade – Toronto’s answer to The Wing – charges $300-500/month. There are cheaper spots but all of them cost more than I’d ideally like to pay.) To approximate the co-working experience in a lower-budget way, you could head over to a friend’s house and work alongside them – just make sure to extend them the same courtesy another time, and bring snacks or coffee or something to express your appreciation for their generosity with their space!

#5: Give yourself structure.

This is probably the hardest part of working from home, and also the most important. Without a boss breathing down your neck, it’s easy to lose track of time and accidentally spend an hour scrolling through tweets on your phone or falling down a Wikipedia rabbit hole instead of doing your actual work.

The most beneficial thing for me in this regard is also very basic: a to-do list. The psychological pleasure I get when I tick an item off the list – or, better yet, when I tick all the items off the list – is a powerful motivator. This is doubly true because my partner has access to my digital to-do list and can check on my progress throughout the day. Having an “accountability buddy” can be a big help!

Some writers have strict daily schedules that they stick to. My work is too sporadic to be able to commit to something that stable, but if it works for you, do it! I also know lots of writers who use task management tools like Trello, Asana, and Teamwork – the latter of which I use at my dayjob and enjoy, because it allows me to track the amount of time I spend on each task so I’m more aware of my own time-wasting/procrastination tactics as they’re happening.

#6: Pay attention to your natural rhythms and arrange your work accordingly.

For example, here are some things I’ve learned about my own rhythms:

  • With very few exceptions, I am not very creative before 11 a.m., so mornings are best spent on more rote or administrative work (e.g. answering emails, scheduling tweets).
  • I am pretty useless for at least a day after arriving home from traveling, so I do my best to ensure I have no deadlines during that window, or that if I do have one, I complete the work in advance.
  • Nights aren’t usually very creative for me, unless I give myself a second wind with caffeine (which peps me up) or alcohol (which opens my mind to making more freeform connections).
  • If I’m really, really into a piece of writing – I’m talkin’ flow-state, “don’t talk to me, I’m working” levels of absorption – I should keep working until that feeling dissipates, if possible, because that’s often when my best writing happens.

Work in our society is largely structured around the idea that you should work at appointed hours all the time even if you don’t feel like it, which – setting aside the hellish capitalistic labor-fervor involved in that idea – just isn’t really in line with how the human mind functions. Freelancers (sometimes) have the luxury of being able to follow our own natural creative rhythms and take advantage of their gifts; this is one of my favorite things about my job(s)!

 

More tips to come later this week! Have you found any of these principles helpful in the past?

Remotely Helpful, Part 1: Flexible & Delightful

This is Remotely Helpful, a new mini series of blog posts where I’m writing up my best tips for working from home, ascertained from years and years of it! Here are my first 3 major suggestions…

#1: Take advantage of your flexible schedule.

Granted, depending on your exact work logistics, your schedule may not actually be as flexible as people tend to assume it is. (I have to get up at 9 every weekday for my dayjob, for example.) But if you do get to set your own hours, at least some of the time, I would strongly recommend making the most of that good fortune!

I love being able to do my laundry at 10 a.m. on a Tuesday when no one else is using the machines, or trotting down to my local movie theatre to take in a weekday matinee when my brain needs a break. I love finishing tomorrow morning’s work early so I can go see a comedy show tonight. I love making time to see a friend for coffee on a Thursday afternoon. I love that if I have an unmissable doctor’s appointment or international flight in the middle of the workday, I usually don’t have to ask anyone’s permission or move anything around, so long as I get the work done at some point.

In the capitalist hellscape that is our society, too often we’re trained to always be thinking about work, and to arrange our entire lives around our work. That’s bullshit, and not even compatible with keeping your brain in top-notch working order. If you have the freedom to do otherwise, you may as well!

#2: Putting effort into your aesthetic makes it easier to put effort into your work.

This isn’t true for everyone, but it is certainly true for me: if I take a shower, get dressed, and put makeup on, I will be plenty more productive than I would if I just lazed around in sweatpants all day. True, working in pajamas is one of the great joys of working from home, but if you find it makes your work ethic worse, it might not be worth it! (I am admittedly naked and wrapped in a bath towel right now as I write this, though, so… do as I say, not as I do.)

Some life hacks I’ve found for this: super stretchy jeans look like “real clothes” but can feel like pajama pants, lipstick makes me feel way more pulled together than I actually am, and nice loungewear is a step up from ratty pajama pants for days when I really can’t manage an outdoors-appropriate outfit.

#3: Your space should be as functional and pretty as you can make it.

For years, I found myself going to cafés to work almost all the time, and I eventually realized part of my reason for doing this: my workspace at home just wasn’t very inviting! It was dark and messy and boring. In the years since, I’ve become more stringent about keeping my workspace clean, and have spruced it up with additions like scented candles, inspiring photographs, and visually interesting knickknacks. One side of my desk is more podcast-focused (mic, pop filter, headphones, pencil and notepad for jotting things down during recordings) while the other side is more writing-focused (pens and pencils, research materials) so I can keep my head in the game. Inside my desk drawers are notebooks, more pens and pencils, and snacks to keep me going.

Other things that might work well in a freelancer’s workspace: good speakers, indoor plants, cable organizers, an ergonomic chair, an external monitor, and a timer (for using the Pomodoro technique or similar). A collection of reference books is also a must – I have journalism style guides within close reach, a whole bunch of sex books, and a stack of my old journals for when I plumb my sexual history to research a piece.

 

More tips to come! What’s your best working-from-home advice?

11 Ideas for D/s Writing Assignments

I’m a writer, an overachiever, and a submissive, so of course I love when my dominant gives me writing assignments. They feel like a task at which I can tangibly succeed – plus, unlike with many other types of scenes, I’ll have the evidence forever if I want to look back at it. Writing tasks have become a major (and majorly satisfying) part of my dynamic with my partner.

That said, we weren’t always as amazing as we are now at coming up with these assignments – so I’ve put together this list you can refer to if you’re similarly strapped for ideas. How many of these have you tried?

Describe a fantasy

This can be one of the most deeply embarrassing things to have to write as a submissive (depending on what type of person you are), so of course, it’s a favorite with dominants! It’s one of the sexiest and most tangible ways for a dominant to gather information about what a submissive wants, making it a highly useful tool in a D/s dynamic. The sub can make lists of their fantasies, write one out as a short erotica story, or use any other framing the dominant desires. This is a great way to unearth some unexplored desires or just expound on some desires you already know you have.

Recap a past encounter

IMO, it’s always fun to hear about sex you’ve had from the other person’s perspective. You get to find out which parts they particularly liked, what turned them on, what they want more of. The sub could write out the events of a past scene, erotica-style, or they could list some favorite past scenes and explain why they enjoyed them so much. You could even do this assignment as a collaborative task, with each of you filling in details of the session as you remember them.

Keep a journal

Some dominants require that their subs keep some kind of diary for them. This could be all-sexy-all-the-time, like a daily log of masturbation or fantasies, but it could also be geared toward making positive changes in the sub’s day-to-day life: they could be required to log their food or exercise if that’s an issue for them (tread carefully!!), keep tabs on the ups and downs of their moods and the factors that influenced them, or make a note every time they do something nice for themselves. Becoming more aware of your patterns is the first step in changing them, and a D/s writing assignment can be a lovely way to achieve that.

Summarize a book

I don’t know about you, but the books I was required to write about when I was in school are the ones that have stuck with me the most. It’s a good way to make information stick in your head. A dominant could assign their submissive a book about kink, sex, relationships, or anything else they want to learn more about, and the submissive could write up a classic essay-style book report, a bullet-point list of things they learned, or any other type of book review the two agree on. (Shout-out to Sinclair and rife for initially introducing me to this idea!)

Keep a to-do list

My partner and I have done this for nearly a year now (wow!) and it’s served us very well. My daily to-do list is kept in a note which I’ve shared with them via the Apple Notes app, which syncs across all our various devices. Particularly in a long-distance relationship, it’s a lovely way to maintain a feeling of connection to each other and involvement in each other’s everyday lives. My dominant can keep tabs on me, see how I’m doing with my tasks, and reward or motivate me accordingly.

Craft an instruction manual

Remember the time my partner made me write directions for giving me multiple orgasms as though I were a literal toy? That was one of the first tasks they assigned me, and it’s still one of my favorites. Especially early in a relationship, the sub might know their body and mind better than their dom does, and requiring them to write an instruction manual is one way to ascertain that information from them without breaking role. They could provide directions for physical skills, like how to give them a nipple orgasm or how to spank them properly, or for more mental/emotional skills, like how to comfort them when they’re depressed or how to best help them relax when life gets stressful.

Research a skill

There may be times in a D/s dynamic when either the submissive or the dominant wants to learn or improve upon a skill, in order to better serve/please their partner. These could be kinky skills, like flogging or bootblacking, or they could be “vanilla” skills, like cooking or cleaning. Either way, it’s fun to have the submissive research the skill and write up their key findings, perhaps including a list of links to more detailed information. (KinkAcademy remains the best place to learn a new BDSM skill, BTW!)

Write lines

While traditionally understood as a punishment, making a submissive write out the same sentence over and over can also be a process of edification and improvement if you approach it that way. For example, if your submissive is chronically self-critical, you could make her write “I am a good, kind, talented, and useful girl” 50 times. That said, it can also be a punishment, as I learned the time I forgot to wear my collar when specifically instructed to and had to write lines and mail the page to my partner as proof. Ooh, how mean!

Help the dominant

My dominant has sometimes required me to put together a report specifically designed to assist them with something – like the time I made some recommendations for androgynous clothing items when they were midway through coming out as non-binary, or the time they asked me to recommend some fragrances I thought they’d like. This is a fun way for a dominant to feel served and catered to, while making their submissive feel useful and needed.

Write a love letter

Love letters are romantic and bonding, and they also help create a tangible record of your romance. I think more people (including vanilla people!) should write love letters, because it’s good for your relationship – and in D/s, you can make this mandatory!

Collaborate creatively

Some of my most satisfying moments with my partner have happened while we’ve been collaborating on something: a song, a podcast, a book. You could do this in-person on paper, or online via the multitude of cloud-based writing tools available, like Google Docs or Evernote. Try retelling the story of your first date together or writing a collaborative poem about your relationship, for example.

 

What are your favorite writing-based tasks you’ve assigned or been assigned in a D/s dynamic?

Freelance Friday: Ruination & Regret

Q. Has there ever been a time/incident where your work “ruined” masturbation or other specific sex things for you (temporarily)?

A. This is, unfortunately, a frequent occurrence for sex toy reviewers. There’s increasing discourse about how monetizing hobbies can make them feel less fun, and I’ve found this to be true about both masturbation and writing at different times in my life.

There were, for example, two years in a row where I issued myself a daily masturbation challenge in May (#DidYouJerkOffToday) and found that by the end of the month, I could barely dredge up any enthusiasm for getting myself off. Yes, even orgasms had lost their lustre. How sad!

I’ve dealt with this by drastically cutting down the number of toys I accept for review, and by generally only accepting toys I think will be good or at least amusingly weird. My most frustrating experiences of sex toy reviewing usually centered around toys that were not good, not bad, but mediocre: decent enough to get me off, but not fun or flashy or earth-shattering or world-shifting. When using a toy is just as boring as trying to string together sentences about that toy, you know your vocation has truly drained the fun from your sex life. So I try to say no to that type of toy these days.

Sometimes people (mostly Tinder matches) express concern that because I write about sex and dating, my actual experiences of sex and dating aren’t authentic because I must be constantly filtering them through the question of “Can I write about this?” I’ve actually taken great care not to do this. I deemphasize actual dates and sex sessions in my writing, usually choosing to write about sexual and romantic concepts more generally, so that I only write about specific incidents when they’re interesting enough that I feel moved to do so. This keeps me from ruining my own romantic life by being too goal-oriented about my writing.

My partners have sometimes gotten frustrated when we needed to test a terrible toy multiple times – Lelo Ida, anyone? – and, as Epiphora has documented, this can put a surprising strain on relationships. It’s for this reason – as well as the whole “I’m in a long-distance relationship” thing – that I almost never accept couples’ toys for review. My job is ridiculous and nonsensical in many ways, and while my current partner is as GGG as I could ever hope for, I’m not prepared to risk my relationships’ stability just for a review!

Q. Have you ever published something you later regretted (e.g. because it was too personal)?

A. The week after an OkCupid boy cruelly ghosted me, I lamented to my therapist that I was already embarrassed by the post I’d written and published about it. The piece had spilled out of me in a tearstained whirlwind, and it had seemed so important that I get it out into the world. But in retrospect, it’s messy, and melodramatic, and god help me if that boy ever stumbled across it. I wish I had waited even a week before pulling the trigger.

This has become a less frequent problem since I’ve gotten serious about my blog as a full-time job over the past few years, because these days I always pre-schedule content, sometimes weeks in advance. I can’t count the number of times I’ve written something vulnerable, queued it up, and then thought, “Actually, no,” and filed it back into my drafts. There’s a piece in there right now called “10 Thoughts Upon Learning My First Daddy Dom Is Someone Else’s Daddy Now” that will probably never see the light of day, because I wrote it in 2017 after a grotesque breakup and that level of grief is akin to a state of intoxication: not a good space for decision-making.

When I showed that piece to Bex, he asked me, “Does it say useful, important things, or is it navel-gazing? Will it teach people something, or was writing it just a good way to process your feelings?” This is still my metric for the usefulness of personal essays. The great Glennon Doyle, a memoirist and blogger, says, “I never put my writing out there until I’ve figured out how this thing that happened to me is really about all of us,” and she’s so right: the specifics of your personal experience, while they might be cathartic for you to get out on the page, probably aren’t artful or interesting until you shape them into something more universal and broad. That’s not to say there’s no place in the world for telling our own unique stories – heaven knows I do it all the time – but I have noticed that the pieces I most regret publishing are the ones filled with unprocessed emotions, word-vomited up without care or consideration.

My friend Kate Sinclaire often says that if you want to do porn, you should first imagine the worst possible person to discover your porn doing exactly that, and if you can live with the reality that they probably will, then you can go ahead and do it. I think the same is true for sex writing. It might seem like a terribly good idea to publish an emotional screed about that Tinder hookup from last week, but what if the person you fucked finds it and reads it? What if your boss does? What if your grandmother does? Self-censorship can poison your creativity, but you need a certain amount of it, or you’ll drown in regret pretty quickly. Imagine the most embarrassing possible person reading your piece, and if that feels alright, then you can hit “Publish.” But please don’t do it before then, you impulsive little imp.

 

Got questions for this series? Drop ’em in the comments or in my contact form.

How I Became a Full-Time Sex Writer

Friends, this blog is SEVEN YEARS OLD today, and that feels absolutely wild to me. I was not always the delightfully busy, proverbial-phone-ringing-off-the-hook sex writer you see before you. Even people who seem like they sorta “have their lives together” had to start somewhere. I’ve read my hero Alexandra Franzen’s post “A chronology of my life as a professional writer” many times seeking answers and comfort, at times when it seemed like the writer thing just wasn’t going to work out… and so it feels like good scribe karma for me to explain, in a similar fashion, how I got to where I am now. As the youths are saying on Twitter nowadays: Buckle up.

2000 or thereabouts. I am a voracious bookworm, a semi-closeted nerd, a precocious weirdo at age 8. I spend hours chronicling my days in my Little Mermaid journal – and, secretly, penning erotica in my ornate Anne of Green Gables journal. Later, I will rip all the filthiest pages out in a bout of shame – but for now, the anatomically ill-informed trysts on those pages fill me with joy.

2006. I’m knee-deep in a musical theatre obsession, and believe, genuinely believe, I will be a Broadway performer someday. I devour all the books I can find on the subject – Audition, Making It on Broadway – and go to voice lessons and memorize monologues and make lists of my dream roles. One night, at a family party, during a discussion of all the kids’ various ambitions, my wise older cousin turns to me and says, “I think Kate will grow up to be a writer.” I laugh, because she’s wrong: clearly I’m going to be singing and dancing on Manhattan stages instead. Right?

2009. My (hot, British) English teacher pulls me out of science class to tell me my recent essay for him was exemplary and that he wants to use it in future lessons. My glee cannot be quantified. That same year, I win first prize in a student poetry contest, and I get to read my extremely gay poem onstage in front of a bunch of literary types. They give me a $100 bookstore gift card which I promptly spend on a lot of Bukowski.

2010. I take a Writer’s Craft class where I get to explore various different forms, ranging from Shakespearian verse to sitcom scripts. Later, one of my favorite teachers lets me take a one-on-one literature/creative writing class with her, tailored to my tastes and goals as a reader and a writer. She assigns me twisted fairytales, feminist essays, Angels in America. I write a play about romance, non-monogamy, and gender confusion, and they do a staged reading of it at my school’s Fringe Festival. I cry a lot in the aftermath, having heard my words in other people’s voices and been utterly lit up by it.

2011. That same teacher recommends me to Shameless magazine as someone they should profile, and they do. It’s my first appearance in a magazine, albeit not a byline. The article captures my frazzled artistic life at the time: improv, painting, poetry. I’m still not settled on the “writer” identity, though I’m getting there.

Early 2012. I take a year off between high school and university, trying to figure out what the hell I want to study. One night, at my commencement, I’m mesmerized by the ASL interpreter onstage, and ponder whether I should go to school for ASL translation, something I’ve often idly thought I might enjoy. But then I realize it would probably be best if I studied something I already know I enjoy and am good at… like… writing. Something clicks. I race home that night and write in my notebook: “MAYBE I SHOULD GO TO JOURNALISM SCHOOL??”

March 2012. I apply to a shitty retail job at a sex shop. I do some Googling about sex toys to make sure I know my shit incase they call me in for an interview – but they don’t. However, in the process, I discover sex toy reviewers like Epiphora and Lilly, and I think, “Hey, I could do that.” I start a Tumblr-hosted blog. I name it Girly Juice. “Could be a fun summer project,” I note in my journal.

April 2012. The owner of a website called Sex Toys Canada reaches out to inquire about a partnership. I’m still new to the sex toy reviewing game, so I eagerly negotiate a deal whereby I will get $140 in store credit each month in exchange for writing 2 articles for the company blog. I acquire my first “free” toys, including an Eroscillator, and feel like a business genius. (Over a year later, I will renegotiate and get them to start paying me in actual money. Only $50 an article, but still.)

September 2012. I start classes at Ryerson University’s School of Journalism. It’s hard – especially “streeters,” where you have to interview random people on the street for a story, the bane of my socially anxious existence – but I feel invigorated and inspired by the smart writers who surround me and the wonderful work I get to read every day.

2013. I get an unpaid internship writing and editing articles for a dating newsletter aimed at middle-aged women. A recommendation letter from my supervisor at the end of the summer says that I have “excellent written and verbal communication skills, [am] extremely organized, can work independently, and [am] able to effectively multi-task to ensure that all projects are completed in a timely manner.” I try to parlay the internship into a paying position, but they don’t go for it – probably, in retrospect, because their economic model hinged on not needing to pay people like me.

2014. I’m invited to write some pieces for on-campus publications, the Eyeopener and the Ryerson Folio; far from limiting me, my sex “beat” just makes people think of me first when they need a sex story written. A J-school colleague of mine interviews me for a story she’s writing for Herizons magazine about labiaplasty. In seeking out the mag so I can read the story, I realize they’d be a great fit for lots of the stuff I like to write about. I pitch the editor a feature story about toxic sex toys, and she loves it. My friends and family rejoice supportively about my magazine debut, a heavily-reported story called “The Greening of Sex Toys.”

2015. I attend a sex bloggers’ retreat called #DildoHoliday, and teach a workshop on generating content ideas and staying on task, since I am, according to one of the retreat organizers, “the queen of productivity.” Throughout the year, I’m interviewed for the University of Toronto campus newspaper, the Offleash podcast, Kinkly’s Sex Blogger of the Month feature, and Sex City Radio. Everyone seems suddenly interested in this weird sex writer girl.

Early 2016. I do my final-semester internship at the Plaid Zebra, where they let me write about sexual health, social psychology, and dick tuxedos. It gives me a taste of what it might be like to be a full-time staffer at a publication – and I discover that I think I’d rather freelance. I take a gig writing monthly articles for a sex toy shop’s blog, to supplement my growing income from blogging and journalism.

July 2016. I pitch an essay to the Establishment about dating faux-feminist men. They accept it, I write it, and… it goes viral. For several days, I basically cower in my bed, overwhelmed by the onslaught of tweets and trolls and threats. I wonder, many times, if the sex-writer life is really for me. I conclude that it is.

Early 2017. I work a sex toy retail job, briefly, before they fire me for no real reason. At first I panic about how I’m going to make ends meet, but then somehow the sponsored post requests and freelance story assignments pour in at exactly the right moment. The sex and relationships editor of Glamour reaches out via DM to say she loves my blog and would welcome any story pitches from me. I write for her – and Teen Vogue, and the Establishment, and Daily Xtra. I dutifully update my portfolio every time a new piece goes up. The Daily Mail writes about what a slut I am, and I’m terrified it’ll incite the trolls again, but it doesn’t, not really.

June 2017. I start my new dayjob as a social media writer for a firm that works with adult-industry clients. It’s 10-15 hours of solitary, largely self-directed work per week. The steady work allows me to relax and not worry so much about whether my more creative work will be able to support me. I stop shopping for button-downs and pencil skirts in a gesture of supplication to some future office-job self; I accept that maybe I am just A Person Who Works From Home Now, and that therefore it’s okay for me to buy star-print leggings and sparkly T-shirts instead.

Early 2018. A Spanish newspaper calls me “the Canadian Bridget Jones.” At my boyfriend’s urging, I pitch a story to a dream publication of mine, Cosmo, and they say yes. When it goes up, my perfect brother tweets, “My sister is now a Cosmopolitan-featured writer!” and I don’t quite believe it until I see his words.

Late 2018. I win an award from the Association of LGBT Journalists. I get nominated for Best Blogger in NOW magazine’s Readers’ Choice Awards. I write big meaty reported pieces for The Walrus and an op-ed for Herizons. I sell several sponsored posts a month, and do odd jobs copywriting and ghostwriting for various sex shops, dating sites, porn sites, and adult content creators. I do my best to follow Alex Franzen’s advice: underpromise and overdeliver. Then I’m invited to teach a sex writing class at the Naked Heart Festival and it validates me, affirms me. This is really my career. Wow.

2019. Herizons offers me a column; I accept. I do more copywriting and ghostwriting and social media writing. I pitch, and write, and network, and brainstorm. The sex writer life, to my delight, goes on.

 

Big takeaways, if I had to choose a few:

  1. Even if your heart is in a particular genre of writing, consider branching out into other areas. I wouldn’t be able to do my fun, creative blogging and essay-writing if it wasn’t supported at least some of the time by social media work, promotional copywriting, etc. – not to mention, going outside your comfort zone helps stretch your creative muscles.
  2. Pitch, pitch, pitch, and pitch some more. Pitch publications you would love to write for, not just ones you think would “let you” write for them. Aim high!
  3. Getting paid for your writing – particularly blogging – can be a slow, long haul. Don’t expect anything to happen overnight. It is more than okay to supplement your income with a dayjob along the way, and even once you become more established. We all gotta eat.
  4. Trolls, h8erz, and rejection letters from editors can all feel much bigger and more important than compliments, fan letters, accolades, and achievements – but they’re not. Do your best to let setbacks fade into your history; they don’t have to define you, as a writer or as a person.

Thanks for being here! It’s been a pleasure spending seven years with you – or however long you’ve been around. ❤️