Battling self doubt in high-growth startups

Every Sunday, Canva’s CEO Melanie sends out a “Sunday Musings” email to the whole team about the key ideas we’re exploring at Canva. Occasionally, people contribute guest musings. The below is from Mike Hebron, one of Canva’s earliest engineers.

I’ve been at Canva for almost four years now. I was part of the team that built version one of the web app and have seen the company grow from eight to more than 100 people. I wanted to share some reflections on my time at Canva in the hopes that a semi-useful nugget of wisdom might be teased out for anyone else working at a startup.

Some background info

I spent my first eight years out of university at a very small educational company in the Bay Area writing desktop apps in C#.

For the majority of my time there I was the only engineer and relied on blogs or question/answer sites like StackOverflow to mentor me. I didn’t write any JavaScript until my last two years there, and even then, I wasn’t writing JavaScript full time. In other words, I would not have hired myself for a frontend position at Canva.

Battling self-doubt

I’m glad I wasn’t involved with hiring decisions back then. I’m also glad our cofounders Cliff and Mel were willing to take a risk and offer me, some guy they met at a hostel, a chance to work with them. Getting a job as a frontender at Canva was both awesome (an exciting startup! In a big city! In another country!) and scary (we have to build an alpha version of a world-dominating product! In three months! With four engineers!).

It was also very surprising. I didn’t think I deserved a spot on the team given my lack of experience, especially when compared to Dave, Cam, and Oli.

The team shortly after the launch of Canva. From left to right: Dave Hearnden, Mike Hebron (writer of this post), Olivier Bierlaire, Jim Tyrrell, Cam Adams, Melanie Perkins, Cliff Obrecht, Lynneal Santos, Zach Kitschke and Hannah de Milta.

These feelings of inadequacy and guilt influenced much of my work, especially the period leading up to the beta launch in 2013. Shortly after the alpha launch in 2012 I remember thinking that if our fledgling company failed, it would be because of the shoddy work I was putting out. I laugh now at how melodramatic that sounds and how silly I was for thinking it, but back then those thoughts made me physically sick from anxiety.

These feelings also made me act to prove my worth to myself and to the team… with mixed results. I worked on weekends, thinking that I could make up with time what I lacked in skill, but ended up burning myself out. I avoided asking questions that I thought were dumb and would expose me as a fraud, but ended up wasting a lot of time and learning lessons the hard way.

These feelings still continue to influence me now, but (thankfully) to a much, much lesser extent. Even with my usual amount of defensive pessimism, I can now honestly say, “I am not a crappy programmer.”

It’s been an interesting journey to get to this point and I think my three biggest takeaways from the trip have been:

  1. Get out of your comfort zone
  2. Let yourself be proud
  3. Have fun

#1. Get out of your comfort zone

I was more than a little scared when Cam asked me to do a pair-programming interview with a candidate named Patrick Lee. I’d conducted interviews before, but never by working side-by-side on code together. It didn’t help when he said that Pat was “widely regarded as the best JavaScripter in Sydney”. What business did someone like me have interviewing someone like him?

Not wanting to disappoint, I spent the next few nights preparing a challenge and reading multiple blogs on how to conduct a pair-programming interview. I sat down with Pat a few days later.

There were some awkward moments that can be chalked up to mutual nervousness. And a few more due to Pat’s trademark stoicness and me trying to mirror it (I read that mirroring helps build rapport), but overall the session passed smoothly. I successfully survived a trip outside my comfort zone, experienced a tiny boost in confidence, and helped with recruiting a new teammate in the process.

There were many more times where I was asked to venture out of my comfort zone. And I’m sure there’ll be many more. Not every trip ends in success, but each of them teaches me something that helps me grow a little more. Even the unsuccessful trips aren’t so bad because the rest of the team is often doing the same thing or has done similar things. They’ve proven themselves to give me support if I fall (by helping with a second attempt or brainstorming ideas on what can be improved for next time) and even before I fall (by answering questions that I should be asking instead of faking competence).

#2. Let yourself be proud

I never thought too much of the little wins that came from succeeding at something new. I never thought too much of little wins in general, actually: I would almost always brush them off as the result of luck. It took me a while to get over that and actually feel proud of my work. I can still vividly remember one of my proudest moments:

Europe’s Final Countdown blared while I changed in our office’s laundry room. I picked out a special outfit for this presentation: a black turtleneck, blue jeans, and white sneakers. I heard our cofounder Cliff’s voice on the mic but couldn’t make out what he was saying. I could, though, make out the chants of my name that followed right after. It was a little embarrassing, and I worried that they were over-hyping what would end up being a so-so presentation. I’m sure they were just being supportive, though, and reminded myself to appreciate the sentiment. I took a deep breath and walked out in the most Steve Jobs-ian way I could manage.

I spent the next 13 minutes introducing and demoing Canva for Play™, a collection of three games that ran inside the web editor (these were for internal use only and not something we shared with users). It was something that I talked about doing all the way back in July 2014 but didn’t actually finish until August 2015.

Mike looking happy, humble and a little bit awkward after his presentation, surrounded by Canva cofounders Cameron Adams, Cliff Obrecht and Melanie Perkins.

The presentation went well and it seemed like the team really liked it. When talking about the project with others I half-joked that the 21-page slide deck I made to introduce Canva for Play™ was one of the few things I was proud of creating during my time at Canva.

One year later and I can see that joke was a little unfair. Looking back at all the work that I’ve done, I can see more than a few accomplishments worthy of pride. I tend to lose myself in the fast pace of work and the constant shifting from one task to another… it’s easy for me to forget about everything I’ve built over the years. I’ve learned it’s helpful to take a step back every now and then and remind myself of what I’ve accomplished.

#3. Have fun

Losing myself in work can get tiring, and stepping back just to survey what I’ve done isn’t always what my mind needs to recover. Sometimes I just need to stop thinking about work altogether.

One of my favorite things about CampJS (a twice yearly, weekend retreat held at some remote campground in Australia) is that there’s no internet access. It forces you to disconnect from the rest of the world and focus on the more important things in life, like playing board games.

On the last night of the conference I found myself involved in an intense game of Avalon with a handful of Canva team members and some other attendees. Briefly, Avalon is a game where everyone is trying to figure out who’s a good guy and who’s a bad guy. Here, I was a good guy. It was the final round of the game and it was up to Paul, a security engineer from Mozilla, to identify all the good guys.

I was certain he would pick the right people, myself included, because throughout the entire game I had laid down so much logic and built up such a strong case for who the good guys were that it would be shocking if he didn’t. To further strengthen my arguments, I reminded him of our friendship borne from the time we spent together during last year’s CampJS. I compared my proposed roster of good guys to the 1992 US Olympic Basketball “Dream Team”. I told him that I was known as “Trustworthy Mike” back at the office. It would be a massive understatement to say that I was invested in the outcome of this game.

To make a long story short, Danny, a bad guy, made a brilliant game move and convinced Paul to pick him over me. Despite the loss, I really do enjoy thinking back to that game (I’m smiling as I type this parenthetical).

I’ve collected many other fond memories along the way: seeing many of my team members in the audience during my first improv performance, trying out different burger-focused restaurants with other burger enthusiasts, celebrating the iPhone app launch… the list goes on.

Cutting loose, participating, and having fun haven’t always come easy to me, but I think I’ve gotten better at them over time. They’ve also proven to bring some balance to my life, and have helped to clear my head so I could re-examine problems that I’m facing with a fresh mind.

Hashtag Thanks

Thanks for reading my ramblings. The lessons seem a little obvious now that I’ve typed them out, but they weren’t always so obvious to me. Even if they were made obvious I’m pretty sure I would still need the occasional reminders (whether they come from myself or from someone else). I hope others find them helpful. At the very least, I know I’ll find them helpful because I now have them written down somewhere.