Asking the Key Questions: Q&A with the PyCon US 2026 keynote speakers: Rachell Calhoun and Tim Schilling

Welcome to our annual blog series where we're asking each of our PyConUS 2026 keynote speakers about their journey into tech, how excited they are for Pycon US and any tips they can provide for an awesome conference experience!

Thank you to Rachell and Tim for this interview! You can learn more about their keynote on the PyConUS Keynote Speakers page and you can also attend their meet and greet at the PSF Booth in the Expo Hall on Friday May 15 from 1 to 2pm PT.

Without giving any too many spoilers, tell us what your keynote is about? 

Tim: Did Rachell answer this question already? Can I cheat off her response? No?

Hmm... Well, it's about Djangonaut Space, a contributor mentorship program for members of the Django community. It'll talk about why the founders created it, what it does, how it works, and why it works.

If you're a part of an open-source community or want to be a part of an open-source community, you may find the talk interesting. We've tackled some really hard freaking problems. Improving diversity, finding regular contributors, and helping them grow into community leaders.

When we sat down to discuss what we wanted to speak about (thanks again, Jon, for advocating for us!), we decided we wanted to focus on the human element. We lean pretty hard on that in our community, and our keynote reflects that.

So, what did Rachell say? 

Rachell: Tim and I want to talk about what happens when you invest in the people behind the commits. We're going to take you inside our open source mentorship program, Djangonaut Space. The success stories, the ripple effects, and how one person's growth becomes someone else's opportunity. Oh yeah, and there's some open source in there too!

How did you get started in tech/Python? Did you have a friend or a mentor that helped you?

Rachell: I had been teaching English for a while in South Korea and I wanted to do something else because I had kind of hit a plateau with where I was. So I tried to get a job at an e-publishing company that wanted someone with English teaching experience, some tech, and some business. I had one out of three.

I remember one of the questions they asked was if I knew what HTML was. I said it had something to do with the web. I had no idea beyond that. Kind of thankfully, I did not get that job, but it was the moment I realized tech touches everything, so I started learning. 

Did I have mentors and friends? Yes, lots, and I would not be here without them. The most impactful learning experience from one was when I asked a friend a question and he said “I don’t know, let’s google it”. And I was shocked that he didn’t know everything. This normalized not knowing everything and made me feel a lot more comfortable while I was learning and even today!  Tim: As a child, like a 5-year-old child, my mom was supportive of me messing around on the home computer. I still have this fuzzy memory of me at school "fixing" the computer in kindergarten. In reality, I was just unplugging and plugging things back in, but hey, it worked!

I got into programming in college when I was accidentally put into the computer engineering program. I noticed it about two weeks before courses started but figured it couldn't be too much different than the business school's management information systems degree. After my freshman year, I got an internship at a local company where I learned so much about web development, the software development lifecycle, and working in a corporate environment. That was incredibly helpful to my development.

A year after college, I decided to build my own SaaS (and move across the country). That's when I finally picked up Python and Django. I got started with "Learn Python the Hard Way" and was lucky enough to work with Greg Newman on a project early on.

Though to specifically answer your question, outside the few years I worked in a corporate environment with a manager, I haven't had a stereotypical mentor. I've absorbed knowledge and wisdom from friends, colleagues, and the old standby, the trial and error approach.

What do you think the most important work you’ve ever done is? Or if you think it might still be in the future, can you tell us something about your plans?

Rachell: Hands down it's helping people find their opportunity for upward mobility. It's so easy to get in the weeds with a language, a framework, or even industry specific stuff, especially at conferences. But the point I always come back to with any community work that I do or have done is that this work is giving people their opportunity for upward mobility in a world where that is extremely difficult.

More important than Python, or this package, or a conference talk is helping people be financially stable. Housing, food on the table, health insurance, not constantly stressed about making ends meet. People can't thrive and volunteer their time if they are just surviving.

For me personally, I was a late career transitioner, and the upward mobility I experienced didn’t just help me but also my extended family. It's so impactful. I even need reminders sometimes of how impactful community work can be because I get so deep into the details about, ya know, “what is the exact hex of the logo on this t-shirt for an event”. 

I know folks who have directly benefited from the community organizing I've been a part of in Django Girls, Djangonaut Space, and even just personally. Some have transitioned careers, others found a job after a long time struggling. A good friend attributes the ability to have a kid (a very cute one!) to me because without the career transition into tech, she wouldn't have been able to afford to raise one.

And this motivates me and keeps me organizing. It's not everyone that shows up to a Djangonaut Space session that is going to have some life-changing experience, but maybe one will. And that's enough. Tim: I'm a middle child, so I have literally grown up with a complex to please people, mediate situations, and help things move forward. It's also probably why I crave praise but absolutely hate getting it. I'm pretty sure that's why my answer to this is helping people contribute to open-source software.  

It's something I've been doing in one way or another for a while. In 2020, my efforts picked up quite a bit with Underdog Devs and then getting way more involved in the Django community.

I think the reason why I find it important was solidified when I read my friend Eric Matthes' post "Coding is Political". Programming, software development, and software engineering are something anyone can learn; you don't need a degree for them, and you can get paid a lot to do them. Contributing to open source isn't the only way to learn these skills, but it's freely accessible and provides a benefit to others.

If I can help cultivate organizational cultures and systems that support more people contributing to open source so they learn skills that help them get paid, well, that'd be pretty cool.

Have you been to PyCon US before? What are you looking forward to?

Rachell: I’ve been to PyCon US a few times, but it’s been a while! It’ll be nice to be back. I sometimes feel a bit out of my depth because there are just so many people, but I counter that with finding pockets of smaller spaces to really connect with people. Which is why I like the open spaces, they’re so fun and I always meet new people. 

Tim: No, this will be my first PyCon US. Back in December, I was so excited to come to my first PyCon, blend into the background, and enjoy a new conference purely as an attendee. In fact, I had bought my plane tickets, lodging, and my conference tickets. Then Elaine and Jon invited us to keynote, which threw all those plans right out the window.

What I'm looking forward to is meeting a bunch of new people and experiencing the PyCon US culture. I'm excited to see the similarities and differences between DjangoCon US and PyCon US.

Do you have any advice for first-time conference goers or any general conference tips?

Rachell: Think carefully about what kind of experience you want, and what you want to get out of the conference. If you want to meet people, for example, a great way to do that is to volunteer, or find some interesting open spaces to attend. I love volunteering at registration because you get to see and meet so many people and they have to come to you! It makes saying hi super easy.

If you are interested in certain topics, find those talks and go there! Other people attending the talk are likely just as interested. 

Lastly, drink a lot of water, take breaks when you need them. For example, go outside for a short walk to get some fresh air, it can really recharge you in a mid-day energy slump. 

Tim: In general, eat some protein in the morning. I've been contemplating bringing protein powder to supplement my breakfast. Though this may be a me thing since I tend to not eat when I get nervous.

The better advice is to reflect on your goals for the conference before the conference. Kojo Idrissa shared this wisdom at a DjangoCon US and it made so much sense. By knowing what you want to come away from the conference with, you can put yourself in a position to make that happen. For example, at that event, I wanted to get to know people. So I hung out in the common areas just before dinner. I ate dinner with different groups each night with zero planning. One of those nights, I was in the back of a van with the hosts of my favorite podcast.

Can you tell us about an open source or open culture project that you think not enough people know about?

Rachell: Have you heard of Outreachy? It's an open source mentorship program that pays!

 "Outreachy provides internships in open source. Outreachy provides internships to anyone from any background who faces underrepresentation, systemic bias, or discrimination in the technical industry where they are living."     

Djangonaut Space was not built in a vacuum, and this was definitely one of the organizations we pulled inspiration from in creating it. Although we aren’t there yet, I think paying people for their time is amazing and really important in lowering the barriers to participating in open source. Working for free is a huge barrier. Tim: Yes, I can! I'd love to shout out the Django Commons organization. It's a home for community-maintained Django packages. It seeks to improve the maintenance experience for package maintainers.

What excites me about this organization is that it's working to provide a framework for making the Django ecosystem (and by extension the Python ecosystem) more robust. Maintaining an open-source package can feel like a lonely endeavor at times, but this is a community that wants to support you.

It does so by:

• Providing a home for community-maintained packages and supporting easy transitions of maintainers
• Managing teams and permissions for contributors, maintainers, and administrators of each package
• Having multiple organization administrators (we just brought new people on in April!)
• Automate actions as much as possible
• Provide best practices for packages
• Providing a mechanism for being paid for open-source work

If you have to maintain a Python or Django package and are looking for a more community-based maintenance approach, consider transitioning your project to Django Commons. Or if you're looking to get started contributing to open source and find the larger projects a bit intimidating, consider contributing to one of our packages!