An interview with Tracy Osborn
  • November 30th, 2017

Tracy Osborn, Author of Hello Web Design: Design Fundamentals and Shortcuts for Non-Designers

1 H 18 MIN
In this Episode

Tracy Osborn is the author of the Leanpub book Hello Web Design: Design Fundamentals and Shortcuts for Non-Designers. In this interview, Leanpub co-founder Len Epp talks with Tracy about her background, how she taught herself programming to build her startup WeddingLovely, some in-the-weeds discussion of app design trends preferences, her successful Kickstarter campaigns for her books, her writing, and at the end, they talk a little bit about her experience as a self-published author.

This interview was recorded on November 16, 2017.

The full audio for the interview is here. You can subscribe to the Frontmatter podcast in iTunes or add the podcast URL directly.

This interview has been edited for conciseness and clarity.

A Note About the Leanpub Frontmatter Podcast

This summer we split the old Leanpub podcast into two distinct podcasts:

Frontmatter, which is a general interest podcast where you can listen to Leanpub authors talk with Leanpub co-founder Len Epp about their books and their areas of expertise, from data science to molecular biology, to the history of labor and management. And for those interested in the nitty-gritty of what it takes to be a successful self-published author, at the end of each episode Len asks the author about how they made their book and how they are spreading the word, and other publishing shop talk.

Backmatter, a new podcast focused specifically on the publishing industry and its latest trends. In each episode Len interviews a professional from the publishing world about their background and their insider's perspective on what's happening in the huge and evolving world of book publishing.


Len: Hi, I'm Len Epp from Leanpub, and in this Leanpub Frontmatter Podcast, I'll be interviewing Tracy Osborn.

Based in Toronto, Tracy is the founder of the popular wedding planning and services siteWeddingLovely, a popular speaker, as well as the author of a number of books that help people learn how to code and also how to design.

Hello Web Design: Design Fundamentals and Shortcuts for Non-Designers by Tracy Osborn

Tracy's books, which are inspired by her own experience teaching herself how to code, include Hello Web App, its sequel, Hello Web App: Intermediate Concepts, and her latest, Hello Web Design: Design Fundamentals and Shortcuts for Non-Designers.

The book is based on Tracy's Design for Non-Designers conference presentation, qhich she has delivered at conferences all over the world, including GitHub's Code Conf LA 2016, the Mozilla ViewsSource Conference 2016, and a keynote talk at O'Reilly's Fluent Conference 2016.

You can follow Tracy on Twitter @limedaring and learn more about her work on the web at, and her personal website,

In this interview, we're going to talk about Tracy's career path, learning how to code, founding a startup, her successful Kickstarter campaigns for her books, and at the very end, we'll talk a little bit about her experience as a self-published author.

So, thank you Tracy for being on the Frontmatter Podcast.

Tracy: Thank you, that was quite a comprehensive introduction.

Len: I like to do a fair amount of research, maybe more than I ought to, for these podcasts - I like to get to know the person a little bit in advance.

Tracy: It sounds like a lot of stuff to cover.

Len: Well, you've done a lot. I always like to start these interviews by asking people for their origin story, and I was wondering if you could talk a little bit about your early life and your education, and how you originally became a web designer.

Tracy: I was really lucky that I had several family members who worked in computers early on. I was born in 1984, and all of my life I remember having a computer. Like the old Mac, with the really tiny four-inch screen, or the ones that have those giant floppies.

One of my earliest memories is having one of those little catalogues, where you can just paw through all the floppies. And family members who worked in tech would just give us all these random things. It was like, "Oh, what is this one?" and you put it in the computer, and oh, it's a colouring game.

I was really lucky to grow up surrounded by computers, especially because I lived in a rural area. So the choices were, "Fo play outside and climb mountains, or stay inside on the computer." Of course I chose to fuss around with these giant floppies, and figure out how computers worked - I spent all my time indoors playing on them, computers from 1986 on, or around that time.

In high school, that's when the internet really started becoming a thing, and I discovered that it was a quick, easy A if I made a website, rather than writing a book report. So it'd be like, "Go research Jonas Salk," and instead of writing whatever pages of the book report I had to do, I'd make a website, and put a paragraph of information on each page of the website.

Websites were so new that the teachers were like, "Wow, you put this on the internet," and they would all pull it up on their computers in the classroom, on whatever slow internet connection we were on, and just blow their mind. It became my way of getting an easy A when I was in high school. That's kind of where the web stuff started with me - because I used it to skate through assignments.

And when I went to university, I thought because I loved computers and loved building websites - I was like, "Oh, naturally, I'll go and do Computer Science." That's a whole story on it's own. I went to Cal Poly-San Luis Obispo in California for Computer Science, and quickly found out I hated university-level programming. So I switched my degree over to arts - I decided to do a complete 180, and go to the opposite direction, because I thought I hated programming.

I finished my university degree in arts, got a job doing front end development, just HTML and CSS, after university. After I left that job, that's when I looked back at programming, and I decided to launch a startup, because I was in the Bay Area, and that's what everyone does.

Len: If I could just interrupt you there, what was it about university programming classes, or the program that you hated so much?

Tracy: Jumping ahead a little bit. I wrote Hello Web App because I didn't like the way that programming is taught. I really realised that in university. I wrote my books in a way that teaches programming in a more visual, a more concrete way. We're actually building something. Whereas my university education - back in the day - was very theory-based for the first few classes.

I think my first quarter class, we were building things, but the key class for me was this theory class at the end of my first year. It just murdered me. We had to reverse engineer sorting methods, and create this report showing the timing of the sorting methods that we've reversed engineered and proving that bubble sort - these are all things I barely remember - but bubble sort, it was better than another sorting method.

It was just not fun to me. I learn better when I'm building something. And the teacher also involved in the class really didn't like me, and once accused me over email of - when I wasn't getting something, he accused me of just trying to skate my way through the class, and was really mean. It's a whole long story. I was like, "I hate this," and so that's why I switched my major. I sometimes want to take my books back to that professor, and be like, "Ha, ha, see I actually did learn programming. I learnt Python. It's much better than Java," which was what we were doing too.

Len: That's a really interesting story, not only because of the element of personal relationship that came into it - which is one of the pitfalls of university life that people often don't talk about, that their professors are people, and they can take a dislike to someone, and they can actually personally take it out on people. And it's such a perilous journey... but there's also a sort of unofficial theme of this podcast, which is that, because so many of our authors that we interview are programming folk, I find about half formally studied Computer Science, and about half didn't. I always like to ask people - I mean things change so fast - if you were starting out again now - would you go into Computer Science, or would you just strike out on your own if your goal was to have a job as a developer in tech.

Tracy: There are so many resources online now for teaching yourself, which is awesome. One of the reasons why I wrote my own book is I found it really "easy" - I say "easy" in air quotes, which you can't see - easy enough to write my own resource, rather than say going back and spending four years in university. That said, I don't want to hate on my university too much, because I just found out that they've revamped our Computer Science program at Cal Poly, and now they teach Python. Now these introductory classes are building real things, qhich brings me so much joy, to know that some of these university courses are taking the criticisms around teaching Computer Science, and they're starting to update it to be more applicable to the real world now. So yay, Cal Poly - I'm really happy to hear that.

Len: It's funny, you're giving me an opportunity to ask another type of question, which is for those of our listeners who might be technical types, who've never gone near an art class. What did you study as an art major?

Tracy: My specialization was graphic design. The degree name, officially, was Art And Design. I loved art in high school as well. I just did art classes and played around o the computers.

A funny thing about being an author, is I am terrible at grammar and spelling and all those writing things. That was definitely my worst classes in university and high school.

My two things were art and computers, and especially graphic design. I was in this, "I hate computers moment," because I had switched out of Computer Science, and I was planning on becoming a product designer doing labels on wines or packaging.

But I kind of fell back into doing web stuff while I was in university, because there was this startup - literally a bunch of guys in a garage down the street from the university. They were building this startup around online education lead generation, and they needed a designer, and I needed the job. So while I was in university for graphic design, I started working with them doing the front end development. I ended up working with them for four and a half years - three and a half years after my graduation. I fell back into computers that way, even though my plan while I was studying art, was to become a package designer.

Len: And you did spend five years working as a web designer. Can you describe a little bit to people what the day-to-day life of a web designer is like? What's the first thing you do in the morning?

Tracy: I will say that my experience is probably really different than other people's. Because it was a startup, it started out as just a bunch of friends working together, building a startup and trying to get rich together. Which didn't really work out. I'm not going to go too much into this, but it was one of those classic cases where I never got anything in writing, and then after the company was successful, I tried to get things in writing, and it didn't match with what my expectations were. Which is why I left that startup.

That said, for a long time, it was just a bunch of friends working together. I also was the only designer at this company, which is a good and bad thing, because when I started working with them, I didn't know CSS. This is when CSS just started becoming a thing, and I didn't know CSS, I didn't know a lot of modern web tools, because my graphic design degree, while it did have web design classes, the web design classes were already outdated. We were doing Flash and Dreamweaver stuff when HTML and CSS were, and still are, the way to build websites.

At this job, I didn't have any designers telling me what to do, anyone leading. I had to really educate myself. And this was a great place for me to learn web design, because this company had a slew of different websites - they had about 13 different properties. When I was hired, it was, "Okay Tracy, redesign this property." So I would do a redesign of one and then move onto the other, move onto the other. And by the tim

Podcast info & credits
  • Published on November 30th, 2017
  • Interview by Len Epp on October 16th, 2017
  • Transcribed by Alys McDonough