Long overdue life updates

A collection of learnings from my freestyle / funemployed / founder arc :)

Hello again,

It’s been a while.

Last time I published anything it was somewhere around early October, and I was just embarking on the term ahead. I declared boldly that I was going to go figure out how to be the coolest version of myself (on my own terms), and also declared that I’d bring you all along for the ride.

Somewhat predictably, somewhere along the way I stopped sharing life updates. I anticipated this would be due to my own lack of commitment, but the updates actually ended up stopping due to my relationships with writing and having an audience in the first place.

Writing has always been a way to sort through my most confusing thoughts. 90% of the things I write are written within 20 minutes of sitting down — usually because they’ve been writing themselves in my head whether I want them to or not. Walking down the street, on the metro, in the grocery store, my brain fixates on the topic of the week and holds me hostage until I give in and try to detangle the swarm into one coherent string of thoughts. Finally getting it all out on paper often comes with a deep sigh of relief.

✨ An essay writing itself ✨

My relationship with having an audience is also interesting — it is singlehandedly my greatest source of both motivation and distraction. I rarely create anything without an audience in mind — I get a lot of joy and satisfaction from being able to channel my thoughts into some form of consumable media (writing, videos, long-winded-speeches), seeing how others interpret whatever I create, and using it as a vehicle to better understand the world and the people around me. That being said, the feedback loop — the likes, comments, metrics, dashboards, connection requests, coffee-chat suggestions — has an incredibly powerful ability to knock me entirely off course. Creating something I’m really proud of is great, but the attention it brings means I work through the backlog of all the other things I want to put into the world much more slowly (currently at 15 substack posts, 2 videos, 1 company, and counting 🤡).

In October I started to feel like I was receiving too much artificial positive feedback — with more and more people hearing about my company and getting excited about it, I was up to about 12 coffee chats a week, which meant I was getting a lot of virtual high fives for finding a great problem to work on, without getting a ton of actual work done on product development, user research, or structural work that would set the company up to build… anything. To turn the ship around, I had a very dramatic (what’s new) couple of days that culminated in boldly (and internally) declaring to myself that enough was enough, and that I was going off the grid until further notice. Publicly I pretty much did nothing and hoped everyone would kind of get distracted with the hundreds of other things competing for their attention, and this actually seemed to work — I got enough calendar time back to work through the goals I had for the company. Woo. 🥳 🎉

On the flip side, when I go underground for too long, I start to feel out of touch — constantly releasing things into the world (and making it a habit!) helps me stay motivated and stay on track. It makes “sharing things that I’ve made” less scary. It also keeps my brain from getting stale — enough hours spent thinking about the same problem in isolation makes you lose your sense of what progress actually looks like. It becomes clear that it’s time to poke your head up again when that happens. 😎

This balancing game has been infinitely more difficult now that I have no external structure imposed on my time. With no school or work demanding my attention, it’s been entirely up to me to prioritize what I get done, and as someone who has used procrastinating-what-I’m-actually-supposed-to-be-doing as the entire driver of my creative output for as long as I can remember, creative little side quests have been taking the back seat. Now that my #1 side quest has been promoted, I miss the small wins of little exploratory projects. So today I edited and shared a video, and now I’m saying hi.

The rest of this post will be a bunch of the things I’ve learned this term. I won’t go too in-depth into what the company I’m working on is actually building (I actually promise this is coming soon), but I think the learnings are fairly transferable regardless. I also skipped drawing the little stick dudes (I’m sorry, I know these are the fun part), but these have been a thing blocking me on some other essays and I think I just want to get something out into the world. They’ll be back next time.

Now for the learning! 🧠💯🤓📚💡

Corporate Learning:

1. You can self-incorporate for a Non-Profit or a Company on the internet (or with the help of some cheap-ish companies), but you’ll probably only get the details around 80% correct. I got a lawyer because I am a 👑 risk-averse queen 👑 and I didn’t want to be kicking myself later for easily avoidable mistakes.

2. When you start a company, you’re essentially creating a new person under the law. If the company gets sued to bankruptcy, you are a separate entity. Incorporating is a way to protect yourself from liability.

3. Paying people is a cool way to be really intentional when you ask them for their time. I’ve never run more efficient meetings in my life. Since I intend for this company to be a for-profit business, I don’t want to take advantage of the people I most respect / admire / want to invite to my birthday party. Almost all of them pushed back and did not want to get paid, but I think it’s the right thing to do so I was stubborn. It also somewhat helps me get an initial gut feeling for the cost of labour, and therefore be able to model how much money the company needs to make over time to ensure this can be a “full-time thing” for the people I want to work with. This is a company, not a student-run volunteer org, and I’m trying my best to act like it even in the early stages where everything is kind of scrappy.

4. I’ve had to learn how to be really defensive with my own time — when you’re starting a company, since you don’t answer to anyone it’s easy to be treated (by yourself and others) like you’re unemployed. In reality, you intentionally freed up your time to go after something you deeply care about (which means you arguably value your time more than when you were working on other things). Because of this, I’ve tried to value my own time as if I’m paying myself hourly. I’ve also gotten better at telling people that I don’t have capacity for new work, even if technically my calendar is staring back at me empty. I still take breaks and do things for fun, but I’m really proud of how I’ve learned to set boundaries around activities that are draining and don’t add that much value to my life or my goals.

5. Finding potential cofounders is really hard. Maybe I’m just picky, but finding someone who cares as much about a problem as you, who has the right circumstances and commitment to potentially be in it for the long haul, who you also deeply deeply trust to handle themselves respectfully through tough times, who also has a complimentary skillset to you is kind of a crazy set of asks. Most advice on cofounder equity split is to go 50/50 (regardless of who “started” things, equity is more of a motivational tool for cofounders than a credit system of who-had-what-idea-first), and when I bring someone on as a cofounder, I want to be over the moon excited to work with them for a long long time. I’m not currently looking for new cofounders, but for those who want to get involved, I’ll be doing user interviews in the upcoming months. Feel free to reach out :)

6. The best bank account to get if you’re a small Canadian business that pays people via e-transfer is the RBC Digital Choice Business Account Package. They give you 10 free e-transfers per month, but most business accounts make you pay about $1.50 per e-transfer and I was also stubborn so switched banks. This is my most tactical piece of advice. 🤭

Personal Learning:

1. Loneliness is a sometimes brutal problem to work on. Sometimes I get really into the strategic side of things, scheming up plans and frameworks and revenue models and software design that I can throw at the problem and get really excited. I then have to balance this thinking with learning everything I can about the problem (both through academic papers and going through things like Twitter, Reddit, and YouTube video comment sections, etc). Feeling connected to the root of what makes people lonely is essential to developing solutions that are effective, but it’s really emotionally heavy. I would be lying if I said I don’t limit the amount of time I spend per week reading about the problem — with this many people struggling with loneliness (they’re calling it an epidemic!), doing research often means I end up crying about it. That being said, I think caring enough to cry about it is a signal that I’ve found something worth working on, but I also need to stop crying long enough to channel all of these feelings if I want to do anything about it. Not just for society at large, but selfishly because it gives me a sense of purpose to feel like I’m spending my time on this planet making the world better for people I care about. If I’m going to work on any problem, I want it to be this one (at least for now).

2. I am really susceptible to internet spiralling, and it’s important to remember that whenever the world feels too overwhelming and I want to lock myself in a dark room and turn off all the noise, the solution is going against my gut instinct and getting outside, where there is sun, and interacting with real-world human beings.

   

   From Sam Kriss, who writes the Substack publication “Numb at the Lodge”

3. Even as a solo founder, big important problems cannot be solved by one person. It is important to ask for help. Being a person who is visibly working on “loneliness” has made me somewhat of a beacon for very lonely people. When I’ve gotten in over my head, it’s been important for me to connect these people with appropriate resources to meet their needs. I’m grateful to advisors, staff members, social workers, my parents, and my friends for supporting me and supporting my work — throughout this process, I have never personally felt like I didn’t have someone to talk to about my feelings, and that is huge. It’s also very core to why I’m doing this — loneliness shouldn’t be the reason great people don’t do great things, and I would be nowhere without my community. Big huge shout out.

4. Sometimes you blink and an entire week passes by and you’re not really sure what you got done or where the time went. As a student and employee, that’s easy to shrug off as long as you’ve finished your assigned tasks; as a founder, you beat yourself up a bit more because your completed tasks could have theoretically been anything. You set the pace and the agenda, and “living up to your potential” is a battle you will never win. I’ve learned that progress isn’t linear and that having a schedule that allows me to work 15 hours straight some days and take the entire day off the next day is something I vastly prefer to a 9-5 job. As long as I accept who I am, I’m able to lean into my energy and it feels very human.

5. I dislike little-detail stuff and love working on big-picture things, across literally every domain and medium I’ve ever worked in. I will reluctantly do things like set up bank accounts, work on legal things, debug code, and choose fonts, but I love working on user flow, company values, software architecture, database design, and team management. I kind of already knew this before from working on a variety of projects, but it has been reinforced as a founder. Going solo has been challenging, as I have to do tasks that are objectively not difficult but quite draining for me (otherwise they won’t get done), but I also am starting to see the light at the end of the tunnel now that I’m able to hire and collaborate with people.

6. Living in a city where the cost of living is reasonable means you have freedom over how you spend your time. If your rent is 4x cheaper in one city compared to another, you can work 4x fewer hours, have 4x the “runway” to be funemployed, or at a minimum have a lot more flexibility in the type of work you take on. This may seem obvious to people who aren’t entering a remote-first workforce where salaries are not super linked to geography, but I am a pandemic baby so I never truly appreciated the extent of this impact. People in Montreal visibly have leisure time and are just more relaxed, which feels different from places like Toronto or New York. I think this cultural but also directly related to the cost of living.

7. Buying flexible subscriptions upfront is the best way to get me to actually use a service. This applies to the $20/month unlimited BIXI bicycle rental system in Montreal (which I used as my main mode of transit), and also the “10-drop-in-dance-class-pass” that I purchased to bait myself into actually attending consistently. Good to know for later: buy-in + flexibility = participation.

8. I never want my digital life to be more interesting than my life in the real world. I’ve hopped on the trend of having a greyscale phone with barely any apps installed — for around a month, my phone has been so boring and unpleasant to use that it’s genuinely just not something I want to do anymore. Though I’ve tried this before and failed, this time it’s working — rather than coming from a place of restraint against temptation, it’s coming from acting in line with my values and the person I want to be. This has been cool.

9. My overall lifestyle (other than work) is pretty much unchanged. My sleeping, cooking, exercising, reading, watching TV, time spent at home, and really all other lifestyle habits have remained largely the same when compared to the more structured periods of my life. Despite this, the flexibility of my life feels hugely different — for the first time ever, I am unfazed by the sun setting at 4 pm every day because nothing stops me from experiencing it in the middle of the day. My “productive work day” has been replaced by approximately the same amount of meetings (most of which are inbound, most of which I’m an active participant in, most of which I’m excited about), doing fun stuff, and working on things I care about (music, videos, writing, company things).

10. I am more at peace than I’ve ever been in my entire life. I feel confident and decisive in the direction my life is heading, I’m thinking about what really matters to me and acting in line with those values, I’m spending time with the people I care about, and I am no longer comparing myself to lives-I-might-have-led or the people around me. Everything feels possible now that I’m off the treadmill, and I no longer feel anxious about the future. There is so much goodness to come.

11. I will be living my life in freestyle mode for the foreseeable future. When I decided to do this term last March, I wasn’t even sure what I wanted to do with it. With the freed-up mental space from April to August, my guiding question went from “what should I do?” to “what might I do?”, and since September I’ve been able to trek my way through muddy to-do lists and actually dedicate serious energy to the things that get me excited to wake up every day. If I’m going to work as hard as being successful warrants on most paths, I might as well pick my favourite and not just the one everyone else is choosing. At this point I know what I want, and the only true thing holding me back from a life that works to support who I am & all the creative things I want to put into the world is letting the fear of falling behind (in what? I’m not sure) chase me toward building in not-quite-the-right-direction. There is a lot of risk and mental strain that comes with both making the plan and doing the plan, and I absolutely do not have all the answers, but for me personally and for right now, the tradeoff is worth it.

You made it! Congrats on getting to the end.

For you. I had to do at least ONE little dude. :)

Against my nature, I did minimal proofreading and revision on this post — hopefully it’s mostly coherent. More than anything, it was important for me to say hello again.

I swear the other essays are coming, at some point. Probably.

Joss 😎