The kids who were shooting for Waterloo had been on a grindset their entire lives — math competitions, building robots, winning hackathons in their spare time — things the leadership kids could not even fathom wanting to spend time on.

The leadership kids were playing a different game — orchestrating events, participating in business competitions, founding youth organizations, playing sports, running for student council — activities at which the computer science kids turned up their noses.

Both groups were wickedly smart and both pursued “their game” with equal intensity — but I can count on one hand the number of kids who tried to participate in both worlds.

I believe what looked like a mutual lack of respect was actually the manifestation of both groups being intimidated by the other and retreating more and more into pockets of people that validated them — even if that meant artificially limiting their own growth. The hostility stemmed from insecurity and from a perceived lack of belonging.

I’d like to acknowledge that high school is a weird artificial tribalistic environment (see: Mean Girls, Glee, etc), and that mine was significantly influenced by its proximity to the University of Waterloo (most schools don’t have a Friday Night Computer Science club with over 90 members).

But despite those two acknowledgements, since coming to the University of Waterloo and working at several tech companies I’ve seen these same patterns repeat themselves. High school is not all that different from real life — and there is still far too much division between those who self-identify as “leaders” and those who identify as “engineers”.

I am here to declare — enough. Let’s fix this. Let’s build great people.

Life after high school 🌎

This problem persists in many ways:

1. Letting yourself be “typecast” in real life.
   Engineering and people-oriented jobs both have problems attracting talent that’s diverse. I think a big piece of this is the lack of diversity in our role models, and how that dictates the set of options young people think they can aspire to.
   
   Imagine a software developer. Now the head of marketing. A Mechanic. A teacher. Someone from HR. My gut-reaction mental images for “Surgeon” and “Lawyer” are less defined (and I think we have Shonda Rhimes to thank for that), meaning there is evidence that progress can be made at a societal level.

   

   The cast of Grey’s Anatomy vs. the cast of Silicon Valley. While I personally really enjoyed watching both, Grey’s Anatomy likely inspired the next generation of surgeons while Silicon Valley leaned into the software developer stereotypes as a main feature of it’s comedy. Not only was the cast of Grey’s Anatomy racially diverse, but each character had vastly different personalities, levels of extroversion, and upbringings.

   
   If you only see people like you pursuing a few paths, it’s easy to question yourself. If all your peers and role models are going pre-med are you really going to be an artist? If everyone is going into business are you really going to do computer science? With many of my close friends and people I admire choosing other paths, somehow I feel like I’m “going against the grain” by pursuing engineering — despite growing up 5 minutes from the University of Waterloo.
   
   I’m lucky that the stereotypes applied to me are not super harmful, but I think in all industries and for all people, I want a world where people’s aspirations aren’t constrained by what is expected of “people like them”. I want to be a person who can host events and not have that discredit me as someone who can build cool stuff too. Someone needs to make a show about tech that allows a wider range of people to see themselves in the main characters, and in the real world we need to uplift and idolize a more diverse set of people — in all industries.
   
   

2. Making yourself small.
   Even if I try to not get typecast, I’m totally guilty of playing a part and pretending to be someone I’m not. Humans loooove to fit in, and in the name of “I am a software developer now”, for about 2 years I muffled the parts of me that made me stand out. I forgot I could write, I stopped making art, and I for some reason lost the notion that I was a human being who could have many skills and interests. Without even realizing it, I started dressing exclusively in baggy t-shirts and talking about video games that I had never even played during my lunch breaks. Leadership experience was so rare among my peers that I actually thought it was irrelevant and possibly detrimental to being successful in a software role.
   
   Forcing myself into a little box made me feel so SMALL! Being good at math doesn’t mean you can’t also wear sparkly dresses and play competitive sports (or any other combination of things that don’t typically go together)!!! A good friend of mine was a varsity cheerleader, mechatronics engineering major, professional dancer, and now is really into startups and crypto. I told her how I felt a pressure to conform, and she said “oh I’ve never thought of it that way — I love being confusing. I try to be as confusing as possible!”. She is one of my biggest inspirations.
   
   I’ve since realized that most people have weird niche hobbies too but we are all playing this dumb game of pretending we are boring. And for what?!?! Showing up fully as yourself gives everyone permission to do the same, so my advice here is to stop trying to be like everyone else and just be you, in all of your awesomeness.

   

   
   

3. Glorifying technical skills and solutions above all else
   The best solution is often not, in fact, an app. Coding is one of many tools that can be used to solve problems, and other skills are also immensely valuable. Leadership skills are grossly undervalued by people in tech, leading many people to be promoted into management roles because they’re great at coding only to realize they’ve never intentionally learned how to manage people.
   
   

4. Lack of cohesion (borderline animosity) between departments at companies

   It’s hard to find companies with a tight-knit culture between the sales/marketing team and the engineers (and if you know of one, let me know! I want to work there). Engineers often roll their eyes at the slightly-cultish activities on the business side, and business people are usually confused when the engineers put on their headphones and huddle silently in the back corners of the office. The only people who seem to be reliably able to talk to both groups are Product Managers — but they are vastly outnumbered and carrying wayyy too much company culture on their backs.
   
   

Building great people 💪

To the leadership kids:

1. Coding isn’t as hard as everyone tries to make it seem.
   There is a huge difference between understanding how a website gets made and being a Computer Science or Math major. I’ve worked with software developers who were chefs, music producers, lawyers, and fitness trainers before making a career switch, and they’ve usually only been in their new careers for a few years. You can truly start from anywhere. Believing you can do it is step one.
   
   

2. Start small.

   With every other thing you’ve learned how to do, you’ve been exposed to progressively more challenging building blocks since birth. To learn to write well, you started with spelling quizzes, reading circles, and hamburger paragraphs. To learn how to do higher level math, you started with addition, then multiplication, you reflected colourful shapes across an axis, and then you drew straight lines and then curvy lines and then lines that were curvy in multiple dimensions! Learning to code is daunting — not because it requires some inherent intelligence that a select few people were blessed with and you don’t have, but because our education system is lagging behind.

   

   
   Coding, like everything, is a learnable skill — but you need building blocks.

   I recommend starting with enrolling in something like an “Intro to Python” or “Intro to web development” course (there’s probably an elective at your school, but there are also many online boot camps. Even though the internet is free, there is value in curation and support — the guided learning and structured deadlines can help you sort through all the noise. It doesn’t really matter what language you start with, because intro courses are about getting the building blocks. Just start somewhere.
   
   FINALLY — Don’t compare yourself to an expert who started 10 years ago.

   

   Instead, learn with people who are ideally just one step ahead of you. Not only will this be less intimidating, but many senior developers forget what it’s like to be a beginner and struggle to anticipate where you will get confused. The most intelligent people I know are excellent teachers — if someone can’t explain a concept to you in a way that makes sense, that is not a reflection of your intelligence. Being surrounded by the right people is really important.

   

3. It’s ok to put on your “beginner hat” and ask questions.

   It’s probably been a while since you’ve truly been a beginner at something.
   And that is HUMBLING.
   
   Until you know what questions to ask (for me that took me around 6 months), I recommend learning from a real-life human being — the internet can be overwhelming. When someone says “does that make sense?” fight the urge to pretend it does — admit you still don’t get it, and ask them to explain it again, and again, and again.
   
   THAT BEING SAID — ChatGPT is an amazing resource.
   Ask it questions like: “make me a plan to learn how to do web development in 3 months”, “explain this concept to me like I’m 5” or “please help me debug this piece of code!”. On the other hand, if you have a specific project in mind I recommend following youtube tutorials.
   
   Leaning into being a beginner means you will have to wrestle with your ego, but by fighting the urge to only do things you’re good at — you will GROW.
   
   I believe in you.

   

4. Put on your “teacher hat” and think about how you can grow the people around you.
   I’ve learned that as a software developer, just because someone is your manager doesn’t mean that they’re more experienced than you at leading people. Be respectful and read the room (aka don’t try to change everything about your company in your first month there) but if you have suggestions on how to boost team morale, run more efficient meetings, or improve communication — have that conversation! People develop skills asynchronously, and even managers are learning how to do their jobs better every single day. Feedback is valuable.
   
   For your peers — Waterloo is notorious for people not knowing how to socialize or have a fun time. HELP THEM. If you’re interested in learning more about what they’re working on, initiate that conversation. Talking about projects and big ideas is absolute nerd bait (I say lovingly, as someone who self-identifies as a nerd), but many people don’t actually have the audacity to initiate conversations with strangers and struggle to make new friends. If having “camp-counsellor-energy” is a strength of yours, use it. Introverts everywhere will thank you for getting the conversation going.
   
   
   

To the engineering kids:

1. Developing your social and leadership skills is a worthwhile pursuit — and I know you know it.
   I present to you: Maslow’s hierarchy of needs.

   

   The bottom two pieces of the pyramid (physiological and safety) are called deficiency needs — if we hadn’t broadly figured these out as a species, we wouldn’t be here anymore. Because meeting these needs is biologically mandatory, the path (even though there are barriers) is pretty well-defined.
   
   The confusing part comes when you’ve made it out of survival mode and can start thinking about your growth needs — the path through love and belonging, esteem, and self-actualization is long, twisty, and untrodden — with no map to guide the way. It’s also unique to you, and in the absence of strong support systems, loneliness can get in the way of great people doing great things.
   
   It’s hard to admit that you want to learn how to make more friends, have more fun, and talk to people outside of your bubble. Media and culture lean heavily into the anti-social software developer trope, but I think the reality is that the society we’ve been brought up in has replaced genuine, meaningful human connection with shallow validation (likes, comments, followers). You don’t need to be extroverted to want genuine friendships in your life, and most people feel quite lonely.

   

   
   In my opinion, prescribing therapy1 and self-help books as an individually-targeted solution to mass loneliness is comically dystopian — it's a spot treatment for something that we desperately need to be addressing at the source. Because it's an everyone problem, we should all be stating boldly that we are embarking on a collective mission to learn how to connect meaningfully with the people we’re already around, every single day. We are all. Right. Here.
   

   

   
   The good news is that once we stop feeling ashamed and can admit this is an everyone problem, we can do something about it! Appreciating social and leadership skills as legitimate and something worth intentionally practicing will make you a better collaborator, colleague, and friend.
   

   
   

2. Start small.
   Learning social skills is an awkward and non-standard process that places waayyyy too much responsibility on parents (and trial-and-error) to raise well-adjusted humans. If you spend any time around people who care for young children, you’ll be reminded how “using our words” and other social skills are not human nature — they’re explicitly taught.
   
   If you think the learning stops when you’re a toddler, or after middle school, or when you reach adulthood, you are wrong. Why do we not have the tools to talk about our feelings, why is it so hard to develop new relationships after college, why is it intimidating to ask our neighbours to hang out, and why do we have a population of awkward and self-conscious adults who will go out to bars only to stand against the wall watching the 3 people who actually know how to have fun on the dance floor?
   
   No one ever taught us how to dance, and no one really ever taught us how to do any of the other things either — this is why most people struggle. We have placed “hard-skills” on a pedestal and are now confused as we fumble around without the tools to build strong, healthy, connected, and resilient communities.
   
   The biggest barrier to gaining additional blocks is admitting to ourselves we have more to learn, and beginning to practice. So sit next to someone new in class tomorrow. Send a message in a group chat asking if anyone wants to go on a walk. Invite some friends (old and new!) to go out for dinner. Look for coworking communities and events in your city (shameless Socratica and UW Startups plug). If these don’t exist, reach out to me2 and we can talk about getting you up and running organizing some of these spaces. Start small, build bigger, iterate. Momentum is magic.
   
   

3. It’s ok to put on your “beginner hat” and ask questions.

   Not just questions like “How do I make new friends?”, “How do I get people to come to my event”, or “How do I convince people to want to work at my company?” , but broader questions — “How might we?” questions.

   How might we improve the culture of the tech industry as a whole?
   How might we make spaces feel safe and inclusive?
   How might I share the things I learn with the people around me?

   It’s probably been a while since you’ve been a beginner at something.
   And that is HUMBLING.
   
   Don’t compare yourself to the kid who has grown up doing leadership camps and was the obvious choice for student class president — learn with people who are ideally just one step ahead of you. Not only will this be less intimidating, but many experienced leaders forget what it’s like to be a beginner and will struggle to anticipate where you need help. The best leaders I know are interested in “levelling up” everyone around them — if someone isn’t interested in coaching you, that is not a reflection of your potential. Surrounding yourself with the right people is really important.

   

4. Put on your “teacher hat” and think about how you can grow the people around you.

   Recognize that the things you know are really interesting to other people and they’d love to ask you questions — but they might be too intimidated to ask you to explain it to them.
   
   Getting good at explaining concepts at various levels of difficulty is a superpower.
   DO NOT MANSPLAIN (or underestimate the other person) — but be very open about wanting to talk to anyone and everyone about the things that get you excited. While you’re explaining, pause to ask questions like “What context do you already have in this area?” and “Is there anything that’s confusing that you want clarification on?” so that you can tailor the your conversation to your audience.
   
   You’ll find that by breaking out of your bubble and talking to people with different contexts and skill sets, you’ll consider problems from angles you would never have dreamed of. Being a teacher is an act of service, but teachers are the ones who learn the most.
   
   Talking about projects and big ideas is significantly more socially rewarding than small talk, but many people avoid talking about things outside of their comfort zone. If you have interesting things you’re eager to share, start that conversation! Confident-appearing people are insecure too and will love you for holding spaces where they feel comfortable being subject-matter beginners.
   
   

IN CONCLUSION ‼️👩🏻‍⚖️

We can be anything and everything we want to be, but only if we do it together.

Personal growth is maximized when you do things that you’re a beginner at, intentionally, and when you have a community to support you along the way. Growing the people around you will never leave you at a long-term personal disadvantage, because opportunity is not finite. Squad wealth.

We all have things to share with each other, and there is more than enough to go around (in fact sharing is extremely generative — the more that goes around the more there is to go around) — so share and contribute whatever you can. Teach someone about the framework you’re using, go on a long winded explanation of the book you’re reading, tap someone on the shoulder to help you lead your event.

Whether you love to lead or love to build (or both!), I envision a world where the next generation of employees and companies see the enormous value of people who bring both social and technical skills to the table. I envision a world where people who love to lead won’t think that detracts from their ability to be competent software developers, and where software developers have vibrant social lives that make them feel happy and connected to people other than their immediate colleagues. I like the idea of companies that don’t just have strong culture on one team, but where marketing, engineering, and finance can all hang out after work and teach each other about what they do. It feels more human. It feels more awesome.

This was going to be a triumphant reference to the “Get in Loser, we’re going shopping” scene in Mean Girls, but then the walkable, car-free city agenda within me was too strong. This is the electric scooter version of that, and I hope it serves as an uplifting image that encapsulates an optimistic vision of speeding forward into the future in unity, being all that we can be. I will not be taking criticism at this time. 😁 Thank you and goodnight.

A harsh reality that I was lucky to learn young — you don’t get people’s attention or earn their trust by “having potential”. It’s no one’s job to dream up how you could bring value to a team or to identify you as someone special. Potential, even if you believe you have it, is by definition un-actioned: there is no visible evidence of what you can do for whoever is making decisions. The best way to prove you can do the thing is to just do it.

It’s very easy to fall into the trap of chasing permission — asking “How can I join the organizing team?” at an event you’re attending, thinking you need to apply and get accepted into a club before doing whatever it is that they gather to do, sending a resume to a company without selling them on how you specifically could add to the team by using prior evidence of your work.

It’s also really easy to fall into the trap of chasing validation — tailoring your hackathon project, business plan or film festival submission to score well on a rubric instead of what you’d believe in in a world free of artificial reward mechanisms.

These things look like initiative and can take you really far in life — but they precariously allow your success to be defined by a third-party decision-maker who is likely not all that invested in your personal trajectory. And who says the evaluators are even measuring the right things — what if their rubric is wrong?

Theoretically, in an alternate universe (and in reality, in this universe)1 — you could stop spending hours trying to convince others how passionate you are and instead just start doing the thing that got you so excited in the first place.

You, sizing up the hoops you think you need to jump through.

You, getting hypnotized by the percieved effort of all the steps that come before actually doing the thing you want to do.

You, realizing the internet and Youtube are free, there are people you can ask for help, and you can get started NOW and learn the thing you wanted to learn without waiting for permission.

It starts with “No”.

What I’ve learned is that creativity stems from constraints and hearing “no” is a catalyst for innovation — but only if you’re stubborn enough to figure out how to work around the system to still get what you want.

If you know you’ve got it — prove it. Even if you don’t know you’ve got it — GO FOR IT. Want to see a thing exist in the world? Go make it happen.

Flip the game — do the thing, show that you can provide so much value that they want you. And if they still don’t? That’s absolutely fine. You’re left with something awesome. People can’t prevent your dreams from coming true if your dreams were never contingent on their approval in the first place.

So what does that look like in practice? How do you chase goals where the act of pursuing them makes you better?

OK, What do I want?

I like to use the “OK, What do I want, How I’m going to get there” model (Shoutout to my mom and wherever she heard this).

Steps:

1. OK.
   Write down where you are now. All your feelings and frustrations, the current state of you. This is your starting point.

2. What do I want?
   Pause to think about what you want. No, what you actually want. Keep asking until you get to the root.

3. How I’m going to get there:
   Put on your thinking cap and get creative. Is there a way to do the thing that doesn’t require someone to give you permission to do it?

Now let’s apply this to some test scenarios!

1. The Aspiring Student Leader
   Say you’re frustrated with the student council at your school. You’re annoyed that adults call the shots, that it’s a popularity contest to see who wins the presidential position, and that no previous president has really done all that much to make the school a better place. The seemingly obvious route is to apply to be president, run a campaign, win the election, and then do everything a student council president might do but better (with the oversight of the adult administrators at your school of course).

   

   What do you really want? To work with great people, to not be limited in what you can accomplish. To run events and fundraisers, to build inclusive spaces built on effort rather than popularity, where people can feel that their contributions matter and that they’re making a difference.
   
   So how are you going to get there? You could jump through the hoops but that leaves a lot of factors up to chance. This may seem bold, but what if you just… made your own student council? Led a youth leadership organization outside of school that checked all the boxes with none of the downsides? It’s not necessarily a lower effort path but it may be… less painful? More effective?
   
   This was my villain origin story with SVP Teens. What I didn’t know when I pursued this backdoor was that instead of just one school, I’d be able to work with 90 dedicated student leaders from 16 schools in the region. I didn’t predict that we would raise tens of thousands of dollars to grant to local charities, that new organizations would be founded from the connections made, that it would be a significant source of emotional support during a global pandemic, and that 3 years after my graduation the program would still have over 100 active members from schools across the district. I was fortunate to work with adults who enabled us instead of trying to shut us down, and didn’t have to wait for permission, waste time, or spend my emotional capacity running an election campaign to win votes. Starting with an Instagram account and an idea, I just went for it.

2. The Determined Athlete

   OK — I was trying out for a coach who had cut me from his team before, and feeling nervous that he would cut me again. Whether or not I deserved to be on the team, I didn’t want to leave it in his hands to decide if I got to play high level hockey in the upcoming year.
   
   What did I want? To play on a high-level team, to play often, and to get better. None of these goals were contingent on playing for him specifically.

   

   So how did I get there? The first coach did, in fact, end up cutting me. But since I had been proactive in my pursuit of a backdoor, I had reached out to the coach of a competing local team. This coach went above and beyond, coming to watch me try out in Waterloo before inviting me to his own tryouts.
   
   The second coach ended up being the best coach I’ve ever had. When I pursued this backdoor, I didn’t know we’d still be in contact over 5 years later. I didn’t know that the team I’d join would be the first team I’d been on that felt like a family, or that I’d come to love hockey so much that despite living in another country I’d be taking a red-eye flight mid-coop term to play in Provincials one last time with this team. It started with an email and a “no”, but is without a doubt one of the best things that has happened to me.
   

3. The Eager Photographer

   As a student, joining a club seems like the obvious way to do the things you love surrounded by great people. Many people that attend our events will ask “how can I get involved?!” and list the ways they’d love to help.
   
   Many clubs and teams have formal application processes — at their most ridiculous, students will write essays upon essays, other students will spend hours parsing through applications, everyone spends significant amounts of time conducting and participating in interviews, there is secrecy and anxiety, and at the end of the day 92% of the candidates will get rejected. Unless the club is an “HR Club”, none of this excessive process is even remotely related to why people joined the club — yet recruitment and admissions seem to be where hours disproportionately go. It’s been too long since we questioned — who is actually benefiting from this system?

• OK, I want to take photos for a club. What do I want? To take photos for a club. What’s the backdoor? Show up to an event, start taking photos. Send the photos.

  Congratulations! You’ve just become an event photographer.
  
  The absolute quickest way to get involved is to just do it — show up to events, put your skills to use, and make the organizers notice you. Don’t ask how you can help (people aren’t going to be creative for you) — just show them what you can do, and follow through with the execution. You want to run a dinner? Find funding, run it. So much can be accomplished when you stop waiting for the “go-ahead”. Just do it.

Consider yourself permissioned.

Everything that exists today began at ground zero with everyday people being stubborn in their belief that there was a better way to do things. Why not you?

The realization that there are no rules, there’s no script to follow and that you can kind of just do whatever you want with enough confidence and improvisation is a superpower that few people unlock. Once you do, the whole world opens up. If it helps you get what you originally wanted: it’s a backdoor; if it doesn’t, you’ve done things that are truly awesome and have personally levelled up along the way. Win-win.

By just going for it — building the thing, doing the job you always wanted to do — without waiting for permission, you’ll likely end up somewhere significantly better than you could have imagined. Embrace hearing “no” and keep thinking.

It takes a pause for reflection to figure out what you actually want, some creativity to figure out how to get there, and courage to stand alone with conviction, but you can do it.2 Whatever it is that you want, go chase it!3

Hoping that reading this makes something click for someone.4

Consider yourself permissioned5.

Joss 😎

5

Shoutout to for the line “Consider yourself permissioned”. I think about it often.

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[Edit]: Behind-the-scenes critique from my haters & fans: