Back in mid-March, as announcements rolled out across North America asking people to stay home, I returned to my parents’ home in New Jersey to start my new job. (Why did I need to be physically in the States to start a remote role, you may wonder… and that is a long, boring story about immigration and work status, that I won’t tell right now.) When I arrived back at my childhood home, with only my parents, grandparents, and family dogs for company — which, admittedly, is a lot better than quarantining alone — I realized that I had a ton of free time in the evenings and weekends.

So, despite my therapist’s repeated encouragement about “not scheduling all my free time” and “deliberately taking time to do nothing and unwind”, I thought I’d use that free time to run free, online, open-to-all drawing lessons. After all, people had been asking me for years to teach them how I do the things, and I thought, why not launch a sizable personal project in the middle of a pandemic, right when I start a new job..? (Spoiler alert, as well as a content warning: I learned some things about mental health, that I discuss towards the end of this post.)

A brief history of content development

At the end of 2018, my friend (and occasional co-conspirator) Marlena Compton invited me to speak at a conference that she was organizing in San Francisco, called “Let’s Sketch Tech!” Marlena had quit her job at a Big Tech Firm to start her own company, AppearWorks, which was putting on the conference. The conference took place over two days at The Women’s Building, and brought together a group of technologists who loved to make art, sometimes incorporating art into their professional lives, in the form of sketchnoting, design, and more.

While preparing to present a sketchnoting workshop at this conference, I met Jennifer Tu, a fellow conference presenter who was also going to be teaching drawing basics, who I consider one of a few people to have given me some of the best career advice I’ve ever received. (Side note: you can hire Jennifer to give you great advice too!) Jennifer and I met up on Zoom to compare notes about how our content would fit together, and it was decided that Jennifer would cover some basics and break down psychological barriers against creativity, whereas I would hone in on confidence-building, storytelling, and intermediate drawing skills.

Anyway, this is a long-winded way of saying that I never thought to turn the inside-my-head knowledge into a presentation or a workshop, without some nudging from some awesome people. I also didn’t initially think it was possible to teach things that I had picked up over decades of doodling anime in the margins of my notebooks. So, after I had locked myself into the obligation of developing a 1.5-hour workshop for Marlena’s conference (conference-driven development, anyone?) I sat down and tried to identify a few major themes in my own work, that I could hang an interactive lesson around. I settled on: banners, depth, anthropomorphism, lo-fi metaphors, and composition basics. The first iteration of the workshop, which became titled “Telling Stories with Doodles”, can be found here.

Having spent double-digit hours on building and perfecting the deck, I wanted to get some more mileage out of my work, so I re-submitted the workshop to Write/Speak/Code 2019. By the way, W/S/C is my favorite conference series. It’s one of the only conferences that, no matter how many hours I spend on my feet and how many cups of coffee I desperately ingest, leaves me feeling refreshed at the end of the weekend. If you are part of a minoritized gender group in tech, I hope you’ll consider coming one day. It’s literally life-changing. My talk was accepted, and I was given a bit of a longer presentation slot this time, so I decided to add a bit more content to the front of the deck, about people and expressions. That was the part that Jennifer covered at Let’s Sketch Tech, and I’d also learned a few nifty tools from Kate Rutter in the meantime, and I wanted to share those learnings with my W/S/C family. The W/S/C version of the deck is here.

I was asked to run this workshop again for Women Who Code Toronto later in 2019, because the organizers happened to come to my W/S/C workshop. Each time I ran the workshop, I noticed a consistent pattern: someone would post a picture of a slide, or their own hand-drawn art, to Twitter, and someone else would ask, “Was this recorded? Will you be doing this again?” To me, this was not only fantastically ego-boosting, but also, it told me that there is perhaps wider demand for this sort of skill-sharing. There were very good reasons to try to get the content recorded, in an evergreen format:

  • Unlike writing technology-specific tutorials that are only as accurate as APIs are stable, learning the joy of drawing will never undergo a breaking API change
  • Doodling is an excellent form of self-care, and I really liked the idea of creating content that could be impactful for the mental health of others.

So, in mid-March, I started shifting my sights online.

The logistics of online events

For years I was involved with organizing tech communities, so I already understood some of the basics of event planning. Here’s a brief list of things I knew to be true about organizing people into a shared time and (virtual) space:

  • Expect at least 50% attrition of “Yes” RSVPs if you use Meetup.com as the ticketing platform
  • Advertise the event anytime, but only open up ticket bookings strategically. Open no earlier than 1 week prior to the event. For short events (under 3 hours), people will forget that they said they’d come, and your attrition rate will be a lot higher if you open too soon. Open too late, and people won’t have enough time to find the event through their social channels. 1 week has been the sweet spot, in my experience.
  • Using a separate ticketing platform like ti.to or Eventbrite.com can push the attrition rate down slightly, for some reason. But still, expect at least 1/3 to no-show for a free event.
  • For the attrition reasons, if you have people on a waitlist in the 3 days leading up the event, I typically just bump up the event capacity to let them in, assuming of course that, the event can safely accommodate the case where 60% of people actually showed up. If you admit people too close to the event time (under 24 hours), they probably won’t turn up.

Online events though, are obviously very different from in-person events. During all of the in-person iterations of my workshop (and you may notice this in both decks) I ask people to hold up their work and share with the people sitting near them. When I run this workshop, I ask for round tables seating 8-10 people for a reason: sharing your creative work is a vulnerable and sometimes uncomfortable act, but getting positive feedback is also so valuable of a propeller to keep on creating. I found that sharing within a small group, with my explicit encouragement over the microphone to “tell someone else what you love about their work” was a good way to balance the two competing dynamics. On Zoom, you can’t easily replicate this experience. (Don’t talk to me about Zoom breakout rooms. The feature is barely functional for community events.)

My first-ever attempt to run “Telling Stories with Doodles” online was a three-hour marathon session. I broke down “People & Expressions”, “Letters & Banners”, and “Depth” into a 30-minute block each, added a section on horses just for fun, and added exercises at the end to practice visual library-building skills. During the final section, I picked 30 words, technical and non-technical, and flashed up each word for 30 seconds, challenging participants to draw the simplest possible representation of that word. That deck is here.

Tools I used

Because sometimes people ask me about this, I’ll briefly discuss the technology I used to run these workshops.

  • The whole workshop takes place on Zoom
  • I dial into Zoom from my laptop and also from my iPad Pro. I turn on my video and use AirPods for audio through my laptop, and I mute my iPad on Zoom, and turn the device’s audio completely down
  • I make the deck in Keynote, and open it from my iPad
  • I use Procreate, with an Apple Pencil, to make the slides, and for live-drawing sometimes during the workshop
  • I use the iPad’s Broadcast to Zoom feature to share my entire iPad screen. (This requires the Zoom client to be installed on the iPad.)
  • I queue up a blank page in Procreate for when I need to demo stuff
  • I present the deck from my iPad’s screenshare, and full-screen toggle between Procreate and Keynote as needed.

I found that by chunking up the workshop into predictably 30-minute modules, people could drop in and out more easily, which was important to me — I wanted people to feel like they could take a break and rejoin. It felt important to make the workshop feel sustainable from a mental health perspective, for attendees.

I vowed publicly to keep running workshops, at a rapid cadence of twice-weekly, until we were free of quarantine. Ha. Haha. Hahahahaha. Yea, that didn’t last. At all. I managed to run three more 2-hour events, and set up a mailing list, before crashing and burning out myself.. yet again.

Marketing, branding, and other things that shift tickets

The first time that I had to get the word out, I basically just shouted on Twitter with an Eventbrite link, and my followers would amplify and circulate the link among their networks. It was social marketing at its purest. The next few times, I wasn’t seeing tickets shift themselves as quickly — I chalked it up to the fact that I released tickets at an odd time (most of my network is in the UK, east coast, and west coast). But also, there are a million factors as to why the Twitter newsfeed algorithm may or may not show my tweet. The only way to overcome this randomness was basically to tweet a lot more, at regular intervals, during times that I knew that people would be awake and scrolling their newsfeeds in London, New York, and Seattle.

I also posted the link to the booking page in a few Slack orgs that I’m in. I hit up my bootcamp alumni slack, the Pivotal Alumni slack, some women-in-tech groups, some of the more active conference-centric Slacks, and pinged the link to a few close friends, asking them if they would share it with others who might be interested. For subsequent events, I kind of felt like my announcements were taking over the #events channels though, so I.. stopped. I let my anxiety about talking too much take over, which most certainly created some missed opportunities.

An aside on ticketing struggles: I initially chose ti.to as my ticketing platform, because I enjoyed the streamlined experience for people booking tickets, and used it extensively when I ran events in London. However, I discovered something very important for distributed events: At least, back in March 2020, ti.to had no support for timezone conversion when automatically generating Google Calendar events. That led to many people DMing me on Twitter and Slack to tell me that their invite was wrong, that ti.to was wrong, and perhaps I might like to send out a mass notification telling people that the workshop was not, in fact, at 12:00 PM BST, but rather, 12:00 PM EDT. I just… decided to never use ti.to again for online workshops that need to account for people’s timezones 😇and switched over to Eventbrite for subsequent workshops.

What I learned about my mental health

But here’s the biggest thing I learned, after spending dozens of hours figuring out all the marketing, branding, event admin, etc. I am not, by nature, a promoter. I am not inclined towards sales. In fact, I made the whole thing free, not because I think my work has no value, but in very large part because I just didn’t want to talk about money, or ask for money, from anyone.

It really took a lot of energy out of me to do the event promotion work, to get the word out, to make sure that the right people knew about what I was doing, and knew how to get involved. I set up a mailing list, and sent a few emails through it, but even that wasn’t free. It cost me time to write those mailers with just the right voice: perky, but dry-humored; professional, but welcoming. It cost me energy to give away my own work for free, so much so that I briefly flirted with the idea of just paying someone $100 a week to be my personal assistant, for no more than 3 hours a week, to do all of this social media, copywriting, setting up Eventbrite events, managing my mailing list, and administering my events for me.

But then, my therapist said: “What if you just… stopped doing all that?”

And I realized that, as much as I wanted to make some impact in the middle of this pandemic, and give people something that could help us all cope with our day-to-day mental health struggles, I had forgotten to take care of myself.

I’ve learned the lesson many times (but I’m not sure I’ve done a good job of internalizing it) that I have to stop trying to do everything, all the time. While I was manually setting up auto-confirm mailers and copy-pasting my code of conduct into all participant-facing text, I had left no time for my brain to recover from… the full day of work that I had just completed, at a brand new job no less.

I’m still hoping to run my workshop and others like it in the future, but I just can’t do the work around managing and admin-ing online events on my own. A few weeks ago, my friend Nitya reached out to me, asking me if I would do the workshop as a Microsoft Reactor event. I said yes, because I knew Aaiman from the Reactor team in Toronto from having previously worked together on events, and knew that they literally are professional event-runners. And honestly.. being able to just turn up and deliver the content was a mind-blowing difference from when I was bootstrapping everything myself. We had over 100 people online during the Reactor stream! This gave me the ability to focus on content development and delivery (the parts I liked!) without having to do the stuff that burns me out.

The future

I’m going to be chatting with Nitya and her team soon about collaborating on more events. I’m not going to organize events as a lone wolf anymore. If you made it this far, and are wondering about how to get involved next time, there are a few things you can do:

  • Join my mailing list! I promise I will only use it to tell you about the next Reactor collaborations, and other free- or low-cost doodling events that I am taking part in
  • Join the Microsoft Reactor meetup in your city, or — honestly, pretty much all events are online for the time being so geography doesn’t matter. Sign up for the Toronto one if you don’t have one in your city. All of my events will be advertised at least through Toronto, but also probably London, New York and San Francisco.
  • I recorded one version of “Telling Stories with Doodles” recently as a “Let’s Sketch Tech.. Online!” pre-conference workshop. Subscribe to the YouTube channel to be notified when it’s posted!

I’m also going to be exploring how to shift towards a streaming delivery model, and away from a synchronous, “all in the same room” experience. In practice, this means looking more at YouTube and Twitch streams, limiting participant interaction to text-based Q&A or chat boxes, and recording everything by default — so I have to be on my best behavior 😉

I’ve learned that the “hold up and share!” experience is meaningful in-person, but it loses a lot of its impact online — so much, that I’m not going to bother trying to replicate it at all anymore. Instead, I’ll continue to encourage people to share their work on social media and Discord, but the focus will very much be on the process of creating, rather than the artifact.