An interview with Sheena O'Connell

7 Sep 2025

We’re delighted to share an interview with one of our keynote speakers for PyCon UK 2025, Sheena O’Connell. Sheena kindly took the time to let us pick her brains about her first steps into programming, her career, the projects that inspire her today, and what she’s most looking forward to when she joins us in Manchester this September. Let’s dive in!

1. What first got you interested in programming, and how did your journey with Python begin?

I’ve always been keen on programming, even when I was a little kid, I wanted to do it. I first got exposed to programming in high school. I had a computer studies class for one year, and we started learning Turbo Pascal and then our teacher left, but I figured I would just keep on learning because I was enjoying it so much.

After high school, I went on to study electrical engineering. Software development was a part of the course. I was exposed to several languages there. While I was studying, I was coding on the side to make ends meet. At one point, someone asked me if I could write a Django application, and I said yes. That was my first introduction to Python, and I loved it.

I’ve had adventures with other languages since then, but Python has been my home language for a long time.

2. What have been some of the most rewarding or surprising moments in your career so far?

Something that strikes me is how much luck comes into play. I’ve been very lucky, but I’ve also made my own luck a lot of the time. I make luck by interacting with the community - showing up and adding value.

One big surprise happened about 6 years ago - I had just left a pretty toxic job, and I wanted to start my own thing. I was trying to get exposure while I figured out what to do next. I ran a workshop at PyCon South Africa, and since I was mainly looking for the experience and exposure, I made my workshop as cost-effective as possible. So it was full of students.

A lot of the students came from a non-profit coding bootcamp. They asked if I would be willing to go and run a few workshops at their school, and I said yes. And that led to a job I loved, and many lives changed. I learned a lot, and I helped many people launch their careers.

A few years later, I applied to speak at DjangoCon US (my first international conference) and they said yes! It was a fantastic experience. Things snowballed from there.

I’m often surprised by the community - a lot of opportunities and support have come my way because of my community involvement. It’s shifted my career significantly. I’ve been able to work on projects that I’m legitimately passionate about and have an impact that I can be proud of because of the often surprising actions of community members.

3. Could you tell us about a current project or idea you’re excited about — professionally or personally?

There are so many things to be excited about. So right now I’m working on two things. One is PyCon Africa, so I’m chairing that. And the other thing is some teamwork training that I’m running through my own company, Prelude.

After PyCon Africa is over, I’ll be leaning in on a few other projects. One is the Guild of Educators - I’m working to set up a mentorship program for people who teach code: A lot of people who teach code are not practitioners and could benefit a lot from having a friendly nerd to talk to. The mentorship program is designed to be pretty light-weight and low risk for the mentor: I think a lot of potential mentors get frightened off by the prospect of too much work or long-term commitments, and so it’s designed with that in mind. I think it can make a real difference. If you pick up one teacher, you pick up a lot of people.

I’m also planning to build an OSS LMS (Learner Management System). I know that there are a few around but I think I’m uniquely placed to make something really good. A lot of the open source offerings are not great to work with. I have some plans around how to make it quite modular and flexible.

I’m also doing some work with the PSF: I’m co-chairing the Education and Outreach workgroup (this is very much a work in progress), and I’m running for the PSF board.

4. How has the Python language and community shaped or supported your work over the years?

I spoke about this a lot in a previous question, but I can add a few details:

It’s been like a flywheel - the more I interact with the community, the more it gives back. Sometimes it’s a lot of work (chairing PyCon Africa is completely bananas), but the community always gives me something back somehow eventually.

5. What are some of the challenges you see the Python ecosystem facing today — and what gives you hope for the future?

There are a lot of money challenges at the moment. I’m sure you heard about the PSF grant freeze. It’s affecting a lot of communities really badly. But the problem is about more than a lack of funds; it’s also pretty hard to figure out how to distribute those funds effectively. The grants program aims to be impactful, but what is impactful in Pittsburgh is very different from what is impactful in South Africa or Namibia, or even Japan.

The current system is not sustainable, and it has some holes in it. But I know that there are a lot of solid people who are working to get it right. I’m sure it’ll get better (and I hope I get a chance to help figure it out).

Another BIG challenge is the upcoming talent vacuum - it’s been hard for junior devs to get work for quite a long time and it’s getting harder. LLMs contribute to that difficulty. I don’t want to knock LLMs, they do a lot of good as well - I use them every day. But they do affect the job market.

I’m pretty convinced that we’ll need software developers in 5 years. But where will they come from? A lot of people who would make great coders get frightened off by the job prospects and choose another career.

A lot of people are aware of this problem, but not a lot of people are talking about solutions. I think there is a lot of bystander effect going on.

The future of Python is dictated by the future of the people in Python.

6. This year, you’re joining PyCon UK as a keynote speaker! What are you most looking forward to about the event?

The humans. For me, the most valuable part of a conference is the interactions. The hallway track. I enjoy the talks, and some talks have had a big impact on me. But the magic is in the community.

7. Without giving too much away, what’s something you hope the audience will come away thinking about after hearing your talk?

I hope that I can cut through some of the noise and help people make good decisions about how to adapt to what is happening. That said, there is a lot that I’m not sure of; my crystal ball is a bit cloudy. So I want to make it clear that I’ll be presenting my best thinking, and that thinking might have some flaws.

I hope that my thinking is challenged and informed, and that I can help push others’ thinking forward. There is a lot we need to think about and talk about as a community.

8. Have you spent much time in Manchester before? Are there any places you’re hoping to explore while you’re here?

My only UK experience so far has been Heathrow Airport. I’m sure Manchester is much more pleasant. I haven’t had much time to think about what I’ll do there, but the people are more important to me than the place. I’ll take things as they come.

I have some family that lives near Cambridge that I haven’t seen in way too long. I’m going to visit them for a few days before the conference. I’m seriously looking forward to that <3

9. What’s a hobby or interest you have that might surprise people in the Python world?

Building temples then burning them down…

There is a festival in South Africa called Afrika Burn. It’s like Burning Man but much smaller. I’ve been involved in a few massive artworks there. When I say massive, I’m being quite literal, the last one was around 22 tonnes. What it entails is a lot of woodwork and power tools, and creative structural problem-solving in the middle of the Karoo desert.

Other than that, I’m a climber and hiker. I occasionally go for 5+ day walks in the mountains. It feeds my soul.

10. What’s one thing you wish more people in tech would talk about?

A lot of people see the upcoming talent vacuum and the plight of juniors, and people talk about it. But I haven’t heard a lot of people talk about what they can do to try to fix things. So many of us have been supported by the community in really significant ways, I think it would be good if more people spoke about how they could give back, or pay it forward.

And that’s a wrap!

Thank you very much Sheena, for taking the time to participate. We look forward to seeing you on stage in September 🚀

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