Video version
You can’t connect the dots looking forward
“You can’t connect the dots looking forward. You can only connect them looking backward.”
That’s a quote from Steve Jobs that I’ve known for the longest time, but I’ve only recently internalized what it means in the context of my life.
Because I have failed a lot. Despite people seeing the achievements that I have, I see a lot of failures. Recently I’ve been getting a lot of questions about how I managed to reach this point of my life where I’m working for Expo. People assume it was a straight path, maybe even a referral. In reality, it’s something I never thought I’d reach, first of all because it was never in my plans.
This is for you if you’re a university student or a recent grad who has no idea what they want to pursue. Or you have an idea, but you’re afraid to go all in. One struggle I had was pursuing so many things to a point where I just didn’t know which one was the right thing to pursue full-time. If you feel lost, this story might help you find some clarity.
Starting behind
For the longest time, I felt behind in my life, especially when I came to university. My social skills were behind because I spent the first 17 years of my life not socializing due to social anxiety. But more importantly, I was pursuing computer science and my parents never allowed me to have a computer up until COVID, around the end of 11th grade.
So going into computer science, I felt so behind. My first year, I spent almost all my free time coding and building projects while everyone was having fun partying and socializing. I struggled to find friends, and I didn’t try to go out because I prioritized coding.
Then that feeling of behindness started to lose its power, and the motivation turned into something else: I enjoy building things. I remember spending my entire first-year summer building my own tools for myself. I didn’t think much of it, but it led me to an internship at IBM.
Orbit: 300 hours of delusion
Fast forward to 2025, my third year. I was entrepreneur coded. I loved building things, and now I thought: what if I can take these things I build for myself and sell them to people? I don’t want a job. IBM was cool, but you know what’s cooler? Being an entrepreneur.
So I started working on Orbit, a super connector you could chat with or call, and it would suggest who you should meet based on your interests, your classes, your availability. The reason I built it was rooted in the fact that I struggled to make friends and find the right people in my first two years. I felt alone in my ambition. Orbit was the manifestation of that struggle, but this time I didn’t want to solve it for myself. I wanted to solve it for my whole university.
Yeah, I was very delusional.
After eight months, I had spent over 300 hours inside the app and much more outside it. The university found out about it and interviewed me and posted about it on their socials. As big as that sounds from the outside, I was too narrow-sighted to the point that I didn’t really capitalize on it whatsoever.
My delusion even reached the point where a video producer from Toronto who had worked with Drake reached out for help with his project, and I said no. I felt like I’d be betraying myself. Fall semester was my last chance to bring the app to life. So I turned him down and went all in on my own thing.
One month into the semester, after getting around 100 people to try the app, I realized the people using it were people who don’t go out. Lonely people. And to make an app like this work, I needed social people to balance things out. I couldn’t do that alone while being a student. So I dumped the idea.
Rock bottom
I figured all those skills and knowledge could at least get me a job I cared about. Because that’s the thing about me: I can’t work on something I don’t care about. I have to care about the outcome.
There was a company building a very similar product to Orbit, called Boardy, except more trustworthy and with a huge network. I applied for a summer internship there and reached the final round of interviews. I thought I had it in the bag. Our mindsets were aligned, the vision was aligned, I had amazing conversations with the CEO and CTO. But in that final interview they realized my skills didn’t align with what they needed at that point in time. They were looking for DevOps people, and I had no business in DevOps.
In parallel, I was applying to accelerators and incubators to keep pursuing the super connector. Rejections there too.
So it was summer, I had no internship, nothing lined up going into my final semester, and I was back home with my family. It felt like I wasn’t making progress on any part of my life. My mom loves me and I love my mom, but I wasn’t mentally there. All she saw was a very stressed kid trying to figure out what to do next.
Brainwashing myself into a “life’s work”
After I gave up on Orbit, I pursued another idea: an AI communication coach. Why? Because I struggled with communicating effectively. I can talk, I can connect with people, but I struggled with speaking articulately.
There’s a recurring pattern you’ll notice about me: I love building software for myself. But when it comes to building software for other people, I’m not the best at it. The more I pursued this product, the more I brainwashed myself into believing it was my life’s work. All these failures led to this moment. I want to help the world speak better, because speaking properly is a prerequisite for connecting with people.
But October and November were some of the most unproductive months of my life. I felt so much resistance to doing the things I didn’t enjoy, and no matter how hard I pushed, I couldn’t do it sustainably.
Looking back, that’s one lesson I learned about being a solo founder: it forces you to see what you genuinely enjoy and what you can’t sustain. As a solo founder you deal with development, product, talking to customers, marketing, growth, operations. It’s exhausting, but it also reveals what you gravitate towards, what you’re naturally good at, and what you want to get better at.
Livestreaming my own rejection
Despite all that resistance, I still wanted to pursue it full-time after graduation. So I applied to Next Canada, basically the YC of Canada, for their Next 36 program. I passed the first round and became a finalist. Four interviews with well-known entrepreneurs, including the co-founder of Next Canada.
I was so confident that I went in with no preparation. That bit me in the ass. In the first interview, the co-founder told me blatantly that my target audience would not work. He shared points I had been aware of for months but never researched or validated, because of that same friction I told you about. I gave him a surface-level answer. The interview didn’t go well. The second, third, and fourth interviews were all relatively good, I think. But I took that first one too lightly, and if I had been more serious about it, I’m pretty sure I would have made it through to the program.
The coolest part: I livestreamed my reaction to the results. December 8th, they said they’d announce in the afternoon, so I started streaming at noon and just waited, yapping to the camera, hoping to capture a win in real time.
I captured a rejection in real time instead.
I was so sure I was the most dedicated person among those finalists. But dedication has to be pointed at the right things. And sometimes it takes a long time to figure out what the right thing is.
The feedback that became a job
So I graduated. Jobless, having spent all of university not applying to jobs. Should I keep pursuing the communication coach? Move on? Quit entrepreneurship? My heart didn’t feel like going all in anymore.
Then around December, I found an app called Purpose, built by Mark Manson’s team. The idea seemed genuinely useful, so I tried it, wrote down all my thoughts, sent the feedback over, and connected with a few employees on LinkedIn. A week later they reached back: they appreciated the feedback. Deep down I was hoping maybe, just maybe, they’d want to hire me.
They were. A 30-minute call turned into two hours. I shared my journey and my failures, and they shared how my feedback aligned with their vision for the product. And I thought: maybe getting rejected from Next Canada led me to this moment, to work with Mark freaking Manson, the person whose book, The Subtle Art of Not Giving a F*ck, transformed my life back in 12th grade.
Notice the recurring pattern: at every new opportunity, the first thing I think is “this is the moment where all these past failures turn out to be for a good reason”. When I got the job at Purpose, I thought “thank God I didn’t get into Next Canada.” Even though while pursuing Next Canada, I thought that was what I was meant to do all along.
In other words: you just don’t know what you’re meant to be doing. All you can do is side quest and experiment. Try as many things as possible. Especially when you’re young, the level of control you have over outcomes is very low, and it’s volatile. But you can handle that volatility precisely because you’re young. You have nothing to lose. I lost hundreds of hours on these things, but every failure gave me clarity.
Rejection is redirection.
We went through the whole interview process and made it work: a three-month trial, with the expectation that I’d continue for longer after that. Everything was going well. I even traveled to LA to meet the team, had dinner with Mark Manson, and beat him at Codenames.
The first hour of day one
Riding that high, I decided to travel back to the UAE to see my family. Finally give my mom the experience of me having a job, working remotely, spending weekends together. So around March, I traveled. And then flights got canceled around that time, so there was a good chance I was going to get stuck in the UAE.
In the first hour of my first day working remotely, my manager told me they didn’t want to continue working with me.
It genuinely broke me. I had traveled all the way to the UAE and was now stuck there for at least a month, jobless again, having never applied to jobs. The TLDR on why: an incompatibility issue, even though I was close with the rest of the team. Instead of showing my family a glimpse of my working life, all they saw, for the second summer in a row, was a very stressed kid trying to figure out what to do next.
The momentum for my communication coach app dropped to zero. And you might think: bro, it’s time to get any job. But I didn’t. After a lot of thought, I realized this experience taught me that I thrive in team settings, ideally a small team where I know everyone. And I still refused to apply to just any job. I still had that delusion of believing you can find a role that aligns, at least 80 percent, with your ambitions, what you’re good at, what you want to get better at, with a team you can grow with.
The email
One day I saw that Expo was hiring a DevRel engineer. Developer relations. The kind of role I’d always thought I’d be good at, but I had no previous professional experience doing it. Just years of doing it for myself.
I wrote a very, very thoughtful email. I shared my purpose, my ikigai, and how it aligned with everything they’d want from a DevRel person: the content creation, the community growth, the support, the teaching. I didn’t know if it would connect with them, but I believed you can find an opportunity that aligns with what you’re looking for. To find those things, you have to reveal the part of you that you want to become.
I was intentional with the companies I applied to and the person I showed them. In total, I applied to four jobs. That authenticity also gave me an opportunity at Ramp.
Expo didn’t respond for two weeks. I followed up. Nothing. I followed up again, and a week later they wanted a call. The first call went well. The second and third didn’t, because I was nervous, and the nerves came from feeling out of control and in a rush. Then silence. I didn’t even follow up, because I didn’t feel like I’d given them a reason to say hell yes.
The day before my final interview with Ramp, I got a surprising email from Expo. They’d be happy to give me an offer.
I remember that day so well. Sitting at my laptop, reading that email, then filming myself for over ten minutes just in shock. I did not believe I’d get that role. I got it.
Now that I’m part of the team, I know exactly why they hired me. That email gave them the context to trust that despite me not being a perfect DevRel engineer right now, my slope, my projection, will reach a point where I become an amazing one. It’s a true blessing to find people who see what I see in myself. They saw how much joy I emit when I’m around people, helping people. That was exactly what they were looking for and couldn’t find anywhere else.
I’m not saying this to brag. I’m saying it because I’m extremely confident we all have these unique traits. But reaching the point of knowing what they are, putting words to them, and showing them even when you aren’t perfect, that takes time. I would have never been able to write that email if it weren’t for all these failures.
Ramp’s role was front-end engineering. I love front-end, but it doesn’t represent what I’m uniquely good at and what I want to get better at. So I took the leap of faith and joined Expo, even though during the interviews it was hard to get a clear idea of what my day-to-day would look like. It’s kind of like choose your own adventure. That’s what a DevRel person does at Expo.
Direction, not destination
All these failed ventures led me to realize what my ikigai is, what I’m good at, what I want to be good at. And that’s where I’m at right now. It’s such a blessing.
So what’s the point of sharing all this?
I strongly believe everyone can find a role that aligns with their purpose. If you can’t find it now, be patient. Remember how the role at Purpose felt like the perfect role? Looking back, it wasn’t. Right now, the perfect role is the one I have. Maybe there’s more for me later. It doesn’t matter, because it’s a journey and you’ve got to walk it.
One thing I didn’t highlight enough: through this whole journey, I was pursuing something. I knew what I genuinely cared about. A lot of people don’t. They’re living other people’s dreams, their parents’ or society’s. Do you really care about getting a big tech job, or is it for the clout and the money? Will you genuinely enjoy your time there? Be honest with yourself.
When you’re young, the consequences of pursuing something you don’t care about are so high. The consequences of pursuing something you deeply care about are so low. Because if you pursue what you care about, you learn more about what you care about, and there’s a very good chance you land on the jackpot. That jackpot can be a job, entrepreneurship, whatever. I didn’t know my current role was the jackpot. On the other hand, if you pursue something that doesn’t feel true to you, the more you pursue it, the harder it becomes to leave and return to the things that align with what you care about.
So please, pursue the thing you care about. If you don’t know what it is, take time to reflect. The things I care about all came from my struggles in high school and university. We all have unique struggles, and these struggles define us. These traumas are gifts. They define your life’s work. That takes reflection, isolation, and most importantly, experimentation. The fuel for all of it is persistence and a sense of purpose.
We all have a gift within us. We can quiet it down and follow the horde, or quiet down the world around us and listen to it. That’s the key to your North Star. The more things you try, the sharper that North Star gets.
I hope my story gave you perspective on the importance of failure, and of trusting the path even when it doesn’t look right, as long as your heart believes it is. At some point, these become the dots you look back at. For some people it takes months, for others years. For me, it took university plus six months.
My only hope for you is that you find a direction in life. That’s all that matters. Not a destination, just a direction. In time, that direction will take you to your destination.
But you’ve got to be patient. Very patient.