My First Boss Told the University I Was a Disappointment. He Never Told Me.

Part 2 of my job journey — what my first real work experience taught me about feedback, fear, and the slow burn toward doing my own thing.

Last week I shared Part 1 — how in 2017, as a University of Waterloo co-op student with two semesters under my belt,

I was struggling to find a placement while everyone else had already landed theirs. Through persistence and luck, a CEO in Toronto's Bloor West Village gave me a shot at his startup.

I was 18. I was excited. I had no other options.

My parents were telling me to come home. I insisted on staying — as long as I could find a job. The gamble paid off when the offer came around May 2nd, start date May 7th. I had five days to find a sublet, move everything, and get ready.

It was tight. But I made it work.

Then reality showed up.

The Entire Dev Team Was Me

When I started, I realized the "team" was just me on the front-end, plus one other developer on the back-end. The company operated out of the founder's basement. Literally.

That part didn't bother me. I joined a startup because I wanted to make an impact. Small was fine.

The problem was technical. I knew HTML, CSS, and a bit of JavaScript. I was confident I could handle whatever came my way.

Turns out the company used Laravel — a PHP framework I'd never touched. The language, the patterns, the conventions — all of it was foreign to me.

I fumbled. Badly.

Faking It

There's a specific moment I still remember. Second or third week in. My boss asked me to build a feature — something with database queries and route handling, standard Laravel stuff. I nodded like I understood. Went back to my desk. Opened the codebase. And just stared at it.

I didn't know where to start. Not in the "this is a hard problem" way. In the "I don't recognize this language" way. I spent the first hour Googling what a Blade template was. Then another hour trying to figure out how migrations worked. Then another hour realizing the thing I'd built didn't connect to anything.

By the end of the day I had something that sort of worked if you didn't look too closely. I pushed it and hoped nobody would look too closely.

That became the routine. I bought books on Laravel. I was learning Ruby on Rails on the side because it was similar enough that I thought the concepts would transfer. I'd get to the office early and stay late trying to close the gap between what I knew and what the job needed me to know.

But every morning I walked in nervous. Not sure if what I'd built the day before would hold up. Not sure if my boss could tell how much I was faking it.

He told me I was doing fine. So I believed him.

The Review I Never Saw Coming

During the mid-term evaluation, my university advisor reached out. "Your employer gave you a really bad review."

Really? I worked with him every day. He said I was doing fine. I was struggling on some things, yes, but I had no idea it was this bad.

My advisor invited me to a Second Cup cafe near my workplace and walked me through the feedback. It was detailed and brutal:

"George doesn't know what he's doing."

"I'm losing hope in the university's co-op program."

"I have to teach him everything — why do I need to do that when I could just do it myself?"

I sat there trying to process.

My boss never gave me this feedback directly. Not once. He never pulled me aside, never told me what I needed to improve, never gave me a signal that he was this frustrated.

I couldn't even blame him for being wrong. He wasn't wrong — I was struggling.

But I didn't know the gap between "struggling" and "my boss thinks I'm useless" because nobody told me.

The Fear Set In

That started the first crisis period of my working life.

I started becoming afraid of going to work. The nervousness I'd felt before turned into genuine dread.

I knew now that every time my boss said things were fine, he might be writing something completely different in his head. Every interaction had a second layer I couldn't see.

I started staying later — 5:30pm, then 6pm, sometimes 6:30pm — to prove I was still trying. I could work harder. I could figure it out. I just needed someone to tell me what to fix.

I dreaded Mondays. I counted weekends. I'd buy a Starbucks coffee and calculate in my head how many minutes of my paycheck that cost.

I was 18 years old, in a country that wasn't home, working at a job where my boss had lost confidence in me but wouldn't say it to my face.

What Stayed With Me

Two things from that chapter never left.

The first is about feedback. I'm grateful to my boss for hiring me — without him, I'd have gone home with nothing. But I needed that feedback in the first few days, not weeks later through a university intermediary. If he'd told me "George, you're behind on Laravel, here's what I need you to focus on this week" — I could have adjusted. I could have asked better questions. I could have directed all that panicked late-night Googling toward the specific things that mattered instead of flailing in every direction.

Instead, I had zero signal that I was failing until it was already a crisis. That experience is why I give direct feedback now. Fast. Uncomfortable if necessary. The alternative — letting someone think they're doing fine while you're writing them off behind their back — isn't kindness. It's cowardice dressed up as politeness. And it destroys people's ability to course-correct when course-correcting is still possible.

The second thing is harder to name. It wasn't a decision. It was a feeling.

I'd joined that startup because I thought small companies meant I could make a real difference. I gave genuine suggestions I believed were right — weekly client emails, UI improvements, style updates. None were adopted. Not because they were wrong, but because that's not how the dynamic worked when you're the 18-year-old intern and your boss has already decided you don't know what you're doing.

And something about that — not the bad review, not the fear, but the feeling of having ideas that nobody would listen to — planted a seed. I didn't act on it for years. I went back to school. Took another job. Stayed there eight months. Learned more. But underneath all of it, there was this low-grade restlessness that never fully went away.

I wanted to be in a room where what I thought actually mattered. And eventually I realized the only way to guarantee that was to build the room myself.

Nine Years Later

This was 2017. I was literally 18 — no money, still in school, getting bad performance reviews at a basement startup in Bloor West Village.

If you'd told me then where I'd be nine years later, I wouldn't have believed you. Not because the outcome would have seemed too good — but because in that moment, sitting in a Second Cup reading feedback my boss didn't have the guts to give me directly, the future felt completely opaque. I couldn't see past the next Monday.

I think a lot of people feel that way right now. Stuck in something that isn't working, unable to see what comes next, not sure if the restlessness they feel is a signal or just noise.

I don't know your situation. But I know that the version of me who was most afraid — the one calculating Starbucks costs against his paycheck and dreading Monday mornings — was also the version of me who was closest to figuring out what he actually wanted. I just didn't know it yet.

Part 3 — the finale — drops next week.