Interview With Tracy Osborn – The Designer Who Learned To Code And Is Helping Others Do The Same

Meet Tracy Osborn – a designer, entrepreneur and self-taught developer who’s gone on to write two books and speak at over 32 conferences in 2 years! Tracy delves into how she did it, not forgetting to give those of you learning to code a trick or two.

Tell us about yourself.

Hi, I’m Tracy! I’m a designer-developer-author-entreprenerd (phew) living in Toronto, Canada. I’m originally from California and moved up here about 1.5 years ago as my husband is originally from Toronto and we wanted to be near his family. It’s been a huge change.

I pretty much work on the computer so I can earn enough money to spend as much time as I can outdoors. I love to run, hike, backpack, raft, surf, camp — anything outside. In 2014 I completed the John Muir Trail solo, and I’ll be doing it again this summer.

Growing up, I was lucky to have several family members who worked in computer-related fields when I was growing up, so we had a computer even in the mid-eighties. When the internet became a thing in the nineties, I taught myself how to build HTML frame-based websites and, when a teacher would assign a book report, I would build a website instead. Instant A grade, since the internet was so new and magical then!

I really enjoyed building websites so I went to Cal Poly San Luis Obispo for Computer Science, then discovered that I hated the logic and theory part about programming. I switched to Art (with a concentration in graphic design), and ended up getting my first job as a web designer at a startup.

You are a self taught developer. What prompted you to learn to code?

Continuing my story from above! I left my job as a web designer after moving to the California Bay Area and was surrounded by friends starting their own startups, so I caught the bug as well. At first I refused to learn how to code, remembering how much I hated my Computer Science classes in university, so I went on a long search for the perfect technical cofounder.

After months of meetups, interviewing people, choosing someone, and then falling out with them, I was forced to realize that the only way that I was going to get a startup off the ground would be by learning how to code and building it myself.

How did you develop your technical skills? What resources (books, blogs, courses, etc.) did you find most helpful?

My husband is a Python developer, so he pointed me to Learn Python the Hard Way and the official Django tutorial and I started playing around with building a website that showcases local wedding invitation designers. After about six weeks, I had a really basic MVP up and running.

What advice would you give to someone who is considering a career in tech?

Building something real definitely helped me learn way better than if I was just going through a tutorial verbatim. Because I was new to coding and Django, I used a tutorial that walked through building a blog and I altered it so I could build a directory instead. I didn’t know what was going on behind the scenes, but it was working, which was good enough for me.

Both of those lessons learned are ones I try to teach to new developers: Work on something real (because that’ll help the information stick better) and don’t worry too much about knowing everything right at the start. Learn a little more every day and over time, you’ll be surprised how much you’ve picked up. And of course, how much you still don’t know, but hey, that’s programming.

You spoke at 32 conferences and gave 5 keynotes over the last two years. Tell us about how you got started. What prompted you to give your first talk? What was your first talk and how did it go?

Oh lordy, I still can’t believe I did that many!

First, I knew I wanted to speak about design for non-designers and created a talk outline that I was excited to give. It really helped that my talk was geared towards programmers but didn’t rely on a specific programming language, so I took that talk idea and submitted it to every programming conference call for proposals that I could find, regardless of whether I was skilled in that language or not (for example, I spoke at NodeConf Budapest and NodeConf Argentina while still feeling like a complete Javascript newbie.)

I was rejected way more than I was accepted (I actually wrote an article about this!), but I did get some acceptances, which started paving the way for me to become more well-known. At first I was speaking at a lot of smaller conferences, but submitting to bigger conferences became easier once I had videos of me speaking and a resume built up.

The whole programming-language-agnostic-talk worked so well, I created two other talks (one on technical writing and one on marketing) and I was accepted into even more conferences. Once I had quite a few conferences under my belt, that’s when the keynote invitations started to come in (which I love to do because I love to tell stories!)

What is your advice to women who would like to give their first talk?

I started out as a very nervous speaker — voice quivers, mind blanks, sweats, the whole thing. I’ve told myself that the only way to get over it was to just keep speaking, and that every talk will be a little bit better. I don’t expect my talks to be perfect — something goes wrong every time, but I’ve learned to roll with it and have fun. My first few talks are embarrassing to look back on, but I am so happy I did them because they were a key step to where I am now.

You have written two books so far, Hello Web Design and Hello Web App. What gave you the idea to start writing books? Why these books in particular?

As I got better and better with Django, I started thinking of ways that Django could be taught better, especially to folks like me who might be more visual thinkers and learners. I was running my startup WeddingLovely and getting a bit burnt out after a few years, and needed another project to work on, and a book seemed like a fun thing to do.

At first I reached out to publishers and got an acceptance from one, but after looking at the royalties and advance, it seemed like it would be more lucrative and more fun (though a lot more work) to just self-publish. Due to my background in design, I knew how to layout a book, and a Kickstarter campaign seemed like the perfect replacement for an advance as well as a great way for me to test whether a book on Django was viable.

Long story short, the Kickstarter did well, I wrote and released Hello Web App, did another Kickstarter for a companion book (Hello Web App: Intermediate Concepts), and just last month I released a big update for HWA and now both books are bundled together in one big package. I’ve given Django workshops all over the world and sold thousands of copies. It’s been such a fun and fulfilling project to work on.

Hello Web Design came about after I did my Design for Non-Designers talk at conferences and an intro-to-design-book-for-programmers seemed like a great complement to my intro-to-programming-book-for-designers. The style I used for Hello Web App (friendly, a little silly, down-to-earth, more about getting things done than best practices) also seemed like it would work well for teaching design. Long story short, it’s doing great as well and I love hearing from folks who are doing their own design after picking up my book/course.

Both of my businesses were started as side projects in topics that I was passionate about and wanted to learn more about. I had to pick up so many new skills in order to launch the books — how to market the books, sales, printing, running Kickstarter campaigns — but learning those new things made it fun.

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