Gwendolyn Weston


This weekend I went to AffectConf and it was such a space of care, thoughtfulness, and vulnerability that I am left both energized by the amplification of the stories shared and feeling heavy with their weight. That's not a bad thing.

All the talks were amazing and you should definitely at least peruse the transcripts, the hashtag and the keynote videos once they're available, but I just also want to highlight some of my favourite quotes.

First quote is from Talila Lewis' talk where they shared Ki'tay D. Davidson's quote:

“We are all interdependent... the difference is that non-disabled people have had their needs normalized.”

I love this quote because it shifts the premise of self-sufficiency and security from an idea that some people have more needs than others and need to be benevolently taken care of them to the perspective that we all equally have needs and are no more and no less burdensome than anyone else. And perhaps we can use this premise to also help reflect back the privileges we've been afforded; when we notice ourselves having an easier time than other folks, especially folks who from a different context and identity, perhaps we can think — which of our needs have we been privileged enough to have normalized and taken care of?

This theme of centering the needs of people at the margins also came up in Morgen Brommell's talk when they talked about building Thurst, a dating app for queer folks of all genders.

“I think the industry has simply [asked], 'Who is the easiest to create for? And then create that thing. It's easiest to make dating platforms for straight white men.... But for me, I wanted to go the opposite direction and say, 'What is the most difficult issue'?”

The start-up mentality is so often about building the MVP and shipping as soon as possible, but what Morgen points out is that what might be considered an MVP for one population isn't going to be the MVP for another. In fact, such a product might even be harmful, which they demonstrate when they talk about the lack of gender options on Tinder.

Finally, the last quote that I want to highlight is from Sydette Harry's keynote where in talking about why it's justified to punch Nazis, she asks:

“How am I as a black woman going to survive this? When someone is driving a car into a crowd, what words should I have said that would have prevented that?”

Again, it's this repeated theme that solutions for people at the margins require different implementations; as a black woman, she doesn't have the affordance of civility in talking with Nazis because that civility isn't going to protect her when her life is in danger.

And there is so much more wisdom to be had from the other talks that I wish I had the time to cover. Instead, I leave you with some inquiries to explore:

  • The next time you're implementing a solution to a problem or designing a system, how might you center and think of the people at the margins?
  • Do you even know who those people are? And if not, how might you start a conversation with them and learn their stories?

It confuses people when they find out that I am both a software developer and a productivity coach. It seems like such an odd intersection of a career and honestly, when I think about it myself, I get a little confused myself.

Why am I doing this?

Honestly, it started out as a dare to myself.

The emotional labour required for programming is something that I love to think about. How do you work through the challenges of starting with nothing but an idea and molding that into a self-contained experience and system that other people can interact with? How do you untangle the knots of uncertainty, fear, and resistance that show up while programming? Over the years of thinking about these things, I’ve have built up a repertoire of mind tricks, perspective shifts and self-inquiry habits that are the foundation of my productivity. So which made me curious: could I do this work for other people as well?

Only now I'm finding that was the wrong question to ask. When I was starting out, I assumed that becoming a coach would take me a slow-burning amount of time, at the very least a couple of months if not longer. I imagined writing weekly blog posts, building up a reputation of trust, maybe starting a newsletter, eventually teasing out the idea of having 1:1 sessions, and finally, finally, get that first client after all those months and months of work.

In actuality, it took me only a few weeks before I had a full client roster on top of my consulting work.

So now what?

In the end, the question wasn’t if I could do it. The real question is, why is this something I want? What keeps me continuing to do this?

I feel like that’s a question that I haven’t asked myself enough. So often, I get filled with the brim with desire for accomplishment -- I want to get good enough at yoga to teach it, I want to write a YA novel with a strong female protagonist, I want to star in a musical, I want to speak a second language fluently, I just want to know that I am someone who can accomplish these things. Because then, when I get those things, I’m going to be so proud of myself and confident and have such solid a foundation of being the most interesting person in the world that life will be such a relief afterwards. My head echoes so loudly with the, “Can I do this, how would I make time for this, what’s a concrete goal to me for me to measure my progress against, how can I keep myself accountable” planning questions, that I forget -- the question isn’t can I.

Because when you think in terms of can, that’s a fixed mindset. That’s presenting the question like you’re either the person who will accomplish the goal or you’re not, as if you’re sitting there in the audience of an awards show, waiting for the universe to read out the card that says whether or not you were chosen to be the person you want to be.

So if can isn't the question, if I come at this from a place of knowing I am capable, the question is why do I want to choose this? Why is this important to me? What happens when I accomplish my goal, what do I get out of it? What’s waiting for me on the other side that I don’t have right now?

Because when it comes up showing up everyday and putting in the work, that can I do this desire for validation is just not as powerful as the motivation of knowing why do I choose this.

So that’s where I’m at right now with coaching. Yes, I can help people find clarity and untangle their thought knots! What delight!

But why do I choose to do this?

I choose to do this because I like having a break from doing technical work. I’m too curious about various things to fit into a traditional career trajectory, so it’s exciting to explore a non-traditional career path with diverse sources of income and learning how to build my own business.

I choose to do this because I’ve realized that helping other people find clarity also helps me find it in myself. Often, I’ll find that days after I help a client figure out their next action steps for a issue, I’ll find myself running into the same problem and be able to resolve it easier because I had the chance to approach it objectively with someone else.

I choose to do this because I feel like there’s such a lack of awareness and kindness towards the emotional labour of programming. I want to be the person that I needed when I was experiencing my own burnout from tech, the person that says, “It’s okay if you’re uncertain while coding. It’s okay if you’re not productive every waking moment.” (That person for me was actually the coach that I worked with during that time.)

So what about you?

What do you choose for yourself?

(Shout-out to my friend Diana who goaded me well before I was anywhere close to committing to pursuing coaching by saying: “Honestly, I don’t see what’s stopping you from just starting right now. You’re ready.” She helped me move beyond can.)

I have some limited availability for 1:1 coaching, learn more here or sign up for a session.

I often notice an anxiety in myself that I might be plateauing. As I’ve described in a previous blog post, sometimes I worry that I am, “a stagnant shell of a person who unwittingly has let time pass by wasted without growing in any meaningful way”.

Unhelpfully, it’s easy to supply choice details that seem to support this hypothesis. How many years have I held onto certain goals, like publishing an app to the App Store, releasing a music album, or finally completing NaNoWriMo, without accomplishing them? Does the fact that I haven’t accomplished these desires after so long reflect an innate capability to do so?

Well, no, that's just a sneaky fixed mindset. And how boring would life be if that were true? I get such fulfillment and excitement iterating on my identity and skill set that I would hate to just be relegated only to the things that I can reliably achieve.

So to counteract that fixed mindset from settling in too deeply, one effective solution I've found to break through my plateaus is to do more things with uncertain outcomes. The scarier the task is, the better it is for breaking through.

In the past, this has included:

  • proposing conference talks on topics I knew nothing about
  • writing vulnerable blog posts
  • experimenting with whimsical and silly marketing strategies for my business
  • reaching out to cool strangers to try to make new friends

This strategy works for me because when tasks are that terrifying to fathom doing, I end up caring less about the outcome and just giving myself so much credit for even showing up at all. Not to mention that by resolving the uncertainty I'll end up learning something one way or another. So either I accomplish something cool or fail and have some learning to iterate on for the future. It's a win-win regardless of what happens!

After having done this for a while, I've honestly gotten a little addicted to the adrenaline and anticipation that comes from doing scary things. I even sometimes like to make a little game of it by trying to guess success rates (turns out I'm pessimistic and my success rates usually skew higher than I expect).

And if anything, at least it makes life a little less boring.

I have some limited availability for 1:1 coaching, learn more here or sign up for a session.

Eight weeks ago, a couple of friends and I set out to do a weekly blogging challenge where we all had to publish a post every Monday by 5:00pm. When I first committed to it, I imagined that it'd be as simple as taking a spare moment here and there during the week to write up some cool technical thing I learned recently, no big deal. Instead, what happened was each Monday at around 11:00am, I would stare aghast at my computer screen, my head as blank as the freshly opened document in front of me. “I've learned nothing!” I would think to myself in horror. “I am a stagnant shell of a person who unwittingly has let time pass by wasted without growing in any meaningful way!”

And yet, despite all that muddle and fear, every Monday around 3:00pm, I found myself hitting the 'publish' button on a completed blog post. And now, suddenly it's the final week of the challenge and that weekly last-minute rush has turned into an unbroken streak of blog posts.

Part of me feels like it was luck, like each week I bought a lottery ticket that I only just happened to win. But wins can't statistically happen every week so each week I won meant I was probably decreasing my chances for winning next week and ahhhhh the world is full of scarcity!!!

I think the reality is that there was no scarcity of thoughts gestating inside me. Instead, it was by showing up each week to provide a few hours of dedicated space to muddle through them that I was finally able to string them together into something coherent and tangible. Before where all I had were peripheral epiphanies, when I sat down to write and give them space, I was suddenly finding ways they all connected to each other into a constellation of a idea.

Sometimes, I don't have a good sense of who I am or how to share that with another person. I get into situations where I feel like I'm in such a reactive state of gerrymandering myself for each different crowd that it's hard for me to catch a glimpse of myself outside of that performance. But writing is such a necessarily slow process that suddenly, I had the space to figure things out. Where it's hard for me to be to draw up a narrative of myself, share my convictions, argue my ideas on the spot in a conversation, suddenly in the space of writing a blog post, it was only me and my thoughts, going at exactly the pace I wanted.

So each week, regardless of the how well the writing went, seeing the resulting essay felt a little like discovering hidden parts of myself. It's been a little magical, honestly, seeing ideas that I didn't even realize I was incubating suddenly reflected back at me in black and white. Even on the weeks where it felt like I was only writing dull and contrived platitudes, just the act of publishing something mediocre felt revolutionary. To be so unpolished in public, it felt like I was saying,
"Here I am with all these blemished words, and it's okay if they don't resonate with you."

I think there's a little part of me that sees my introversion as preparation for a perfect debut. That my nights staying in to write, read, compose, are all ways of studying and preparing so that one day, I'll suddenly appear in the crowd as a wondrous butterfly of talent and intrigue where before I was only an unassuming and undiscovered caterpillar.

But I'm trying to move past this idea of perfectionism where I only show up when I know I'm fully prepared. It creates a boredom of waiting to be 'good enough' and feeling frustrated by the prolonged days of not being there yet. Realistically, is there any possible sustainable way for me to be prepared all the time? Short of having lots of money/someone to delegate a bunch of my needs to and so on, I haven't thought of any yet.

There's that oft-quoted aphorism about shipping products from LinkedIn co-founder Reid Hoffman, “If you are not embarrassed by the first version of your product, you've launched too late.” I wonder if the same applies to putting yourself out there. Because I've realized that I hadn't really discovered the depths of my resilience until I put myself in uncertain and vulnerable situations. That only by giving a shaky talk at a meet-up, by hosting an event with low turnout, by releasing an app that no one used did I learn to actually believe I could move past the stumbles and failures of vulnerable situations. Counter-intuitively, it seems that failure builds confidence.

I keep wondering though about how to put myself out there more. This weekly blog post challenge has been great for that. Each week I show up half-expecting this to be is the week that I have nothing to say. I've resolved to post whatever incoherency comes out anyway (and have), and it's actually been delightful to see what thoughts and discoveries have emerged because of giving myself that space to write and explore.

So I'm trying to figure out how to do this is in other axes of my life, whether it's programming, or songwriting, or poetry. It's a question I began to think about in another post, of how to put myself out there while still feeling like a work in progress. Maybe it's performing at open mics, maybe it's posting more things to github and documenting my process more, maybe it's finding more ways to collaborate with other people on projects together. Maybe it's making a list of all ways I'm afraid to fail and running straight towards every single one.

Okay, let's start with sharing a poem I've written.

why shouldn't i want to be seen?
why shouldn't i connect my every anticipation
to the marvelous potential of showing up with
a narrative, so carefully prepared,
yet still only a guess, an educated approximation
of my shape and how it might fit
with another?