Why I quit my job during the pandemic.

Why I joined, why I quit, and what happened next

8 min readFeb 5, 2021

I made peace with the fact that I would resign without something new lined up. I knew it was a risky move. I knew my chances of finding something else were slim (I’d been looking for long enough). And I knew the likelihood of being hired by a company that I believed in the way I believe in Canonical, with my level of experience, was poor. But I made my decision. I arranged a meeting with my boss and … Well, let me tell you the whole story first.

Why I joined Canonical

I came to be a Product Manager at Canonical, the company that publishes Ubuntu, for two reasons. First, because I loved the idea of it. After graduating I knew I wanted to work for a good company. Not a big company, or a rich company, but a company with a mission to drive social good. A company where I knew any contribution I made would be doing something I could be proud of. I also wanted to work for a tech company. And this narrowed my options considerably.

I sniffed around and made some ground with a number of companies close to my skillset, even got very close to one in the valley. But it fell through. And then I found Canonical. I’d used Ubuntu before, at University, but I didn’t realise what Ubuntu really was, what it meant, or what it could be. When I dug in I found the world of Open Source, a community over a decade old, and a technology ecosystem that went beyond just Linux to play with the big boys. All in the name of ‘humanity to others’ which is what Ubuntu means. Perfect.

The second reason is that then VP of Product, Stephan Fabel and still CEO, Mark Shuttleworth, were willing to take a chance on me. Thankfully, they saw potential, my passion for the work I do, and my ambition to take on the challenge. All despite my considerable lack of experience. I couldn’t have been more pleased. But fast-forward a year and six months, I wanted out.

Reasons for staying

Positives first. Read this section and the next section and tell me what you would have done. I stayed for three main reasons.

1. The mission

Canonical is an open-source company. Its mission is to make technology more accessible to everyone. That means to use, to develop, to contribute to, all of it.

“In an era where the frontiers of innovation are public, and not private, the platforms for consuming that innovation should enable everyone to participate.” — Extract from Ubuntu mission statement.

I love this. This is exactly what I want to drive my career toward. Making technology more accessible to the people who need it. My opening line to probably too many companies was ‘I don’t want to make nice things for rich people.’

2. The technology

I immediately became impressed, enamoured, and entirely convinced by open-source technology. It just feels like the best way to do things. Passionate people come together to build something for the love of it. Technology that, in theory, is freely available, allowed to be modified and publicly shared. And since it’s untied to any corporate entity, it can be for everyone.

As an open-source company, Canonical supports open-source projects, it pays developers to contribute to open-source projects and it makes its money, mostly, from support. The kinds of technologies go from apps and operating systems for SBCs like the Raspberry Pi, all the way up to full-scale cloud data centre operations and orchestration. And most anything in between. But all that has separate stories of their own.

3. The people

The majority of the people working at Canonical are some of the best I’ve ever met. Across the board, and I worked with (almost) every team in the company. While there are of course some bad eggs, it’s really quite impressive. My theory is that a mission like Canonicals attracts good, empathic, passionate people and they’re easy to spot in the hiring process. Most meetings I had that weren’t straight to business were enjoyable. Plain and simple.

Reasons for leaving

There are always caveats, no workplace is perfect and so there are always negatives. To some extent, it’s just a question of how much you’re willing to put up with. These are my opinions and based solely on my experiences. I in no way claim to speak for anyone else who works for Canonical.

1. Spread too thin

When I joined the Product team there were six of us. A month later there were five. A month later, seven. And two months after that, nine. Including me. The product org was being restructured and its function re-imagined, but once there was some semblance of structure it was clear there were not enough of us. Each one of us became responsible for at least six different initiatives.

Perhaps for an experienced Product Manager (PM), this could have been manageable? And for a long time, I made it work by prioritising two or three initiatives that needed the most attention But for someone who takes pride in their work and wants to do a good job, this ate away at me. I was unable to do what I wanted to do to be successful. I slowly lost my motivation. And while the team grew, the number of things to juggle stayed the same and scrutiny increased.

2. No time to learn

With all of the initiatives and the meetings I quickly ran out of time in my day. But one of the things I most pride myself on is being a serial learner. So the learning I did was by osmosis or trial and error. For a long time, this was great and good enough. I learnt troves of things from interactions with executives and their teams, from interactions with customers and salespeople, and from actually doing the job. Trialling and erroring as I went.

But this only gets you so far. Learning by osmosis (listening in on meetings, trying to make sense of things as they happen/on the fly) is just not my way. I learn by doing, by getting involved and doing. I wanted to learn inside and outside of my work but felt unable to because of the inevitable burn out that came with it. Perhaps this was a time management issue, but without encouragement, or time, on top everything else, it just ate away at me.

3. Difficulty with management

When I joined Canonical, I had a manager. When I left last week, I did not. Our manager, the VP of Product left the company and was not replaced. Instead, the CEO stepped in as an interim manager but without the time or intention to continue a lot of managerial responsibilities. A replacement is still trying to be hired. This left a lot to be desired from the perspective of well-being, administrative help, expenses, and general team management.

Then of course there is the glassdoor famous way that Mark (CEO) deals with people. It can be strict, firm, combative and other adjectives people use to describe that kind of leader. Review meetings increased along with the feeling of tight scrutiny. Group meetings, even those I didn’t lead, induced an amount of dread at what would happen. Whether or not he would come down on someone. Hard. It was demotivating and difficult to stomach when it happens to you, and worse when it’s directed at your colleagues. And over time with all the meetings I had, it ate away at me.

Despite it all, it's important to note how grateful I am. People have lots of opinions and lots of emotions about this kind of thing. But at the end of the day it has led to success and I will always be grateful for the exposure, and the master class I got most every meeting.

What happened when I quit

… so I arranged a meeting with my boss. I accepted my decision. I was resigning. Yet I still spent the whole day agonising over it, full of anxiety and nerves. It took me all morning to work up the nerve to put the invitation in the calendar and in the lead up I had to read a book or zone out on YouTube to distract myself. But as one of my very best friends told me, there would never be a good time. One last meeting. I decided I would be entirely honest, give him all of my reasoning, tell him what I thought and how I felt. What could he do? Fire me?

So I did. And we had easily the most pleasant, healthy meeting we could have had. I told him I was leaving, he asked why, I told him, we discussed back and forth for a while until we reached an impasse. He knows what he does. How could he not? A guy with a company worth hundreds of millions of dollars has a large degree of self-awareness and his handle isn’t SABDFL for nothing (Self-appointed benevolent dictator for life).

His argument was that it is the best way to drive success. He admits he isn’t perfect and is improving, but ultimately, it’s effective. If someone fucks up, how should they feel? Not good about it surely? People need to be pushed. And to an extent, I agree. But my argument was I understand what he does and why he does it, but I don’t like how he does it. So we reached the impasse. His experience vs my optimism?

I thanked him for the opportunity and for the discussion, he thanked me for my honesty. And I left the Canonical Product Team.

He then suggested I join a different team, the advocacy/dev rel team, instead of leaving. *blink blink*. I hadn’t considered that. I said I would consider it. The next day I spoke to the engineering manager, the VP of engineering and the day after that, I took it. I would have been an advocate anyway, I’m a huge admirer of the company, of the mission, andof the people. All of my issues came from my manager's style and were the result of months of build-up.

So I will watch, and I will observe. I will see if he is right. If the way he does things drives success. Or, optimum success, as he sees it. And I will see if in 6 months, or a year, I can go back with suggestions, or if I realise that he’s right. We shall see.