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Designer, Developer, Author, Entreprenerd: Tracy Osborn's Favorite Books

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Tracy Osborn is a designer, developer, author, speaker and entreprenerd (yes, I spelled that one right 😛 ) living in Toronto, Canada. And when she’s not glued to her computer, you’ll most likely find her outside, as she loves outdoor activities such as running, hiking or backpacking. Three years ago, she even hiked alone the John Muir Trail, a 210 mile backpacking trail in California. Impressive, I knooow!

Tracy’s originally from California, so that’s where she caught the startup bug. While in university, she started working as a designer at a company founded in a garage. She then transitioned to freelancing and, eventually, launched her own startup. In 2011, she created WeddingLovely – a wedding vendor marketplace and planning app.

For WeddingLovely, Tracy learned on her own how to code. A few years later, she created Hello Web App, a self-published series of books dedicated to helping designers learn how to code and build their own startup. Tracy will soon launch Hello Web Design, a book that will teach beginner design to programmers, developers, marketers or anyone else who’s not a designer.

Find out from our interview what books had the biggest impact on her and how they helped her:

What’s your favorite book and why? Business and non-business, if possible.

The 4 Hour Work Week is by Tim Ferriss is a book I return to over and over to remind myself why I chose the life that I have. It was key in helping me leave my job eight years ago and jump on the entrepreneurship path.

Non-Business, oh gosh, that’s a hard question. One of the few books I brought with me when I moved was The Scar by China Mieville. I love the steampunk world that was built, the storytelling, and prose.

Was there a moment, specifically, when something you read in a book helped you? Can you tell me about it?

When I was fundraising, I probably referred to Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist by Brad Feld and Jason Mendelson every single day. So straightforward and easy to read — needed when one is fundraising!

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What books had the biggest impact on you? (perhaps changed the way you see things, dramatically changed your career path)

I just read Trust Me, I’m Lying: Confessions of a Media Manipulator by Ryan Holiday and wow, did that change my perspective on the media. Seeing how easily the media can be influenced and how content quality has degraded was depressing but hopefully inoculated me against news designed to create emotional outrage.

Also, When Breath Becomes Air by Paul Kalanithi. Reminded me that life could end in an instant and that I need to focus on living, not working.

What books would you recommend to youngsters interested in your professional path? Why? (no number limit here)

How to Win Friends and Influence People by Dale Carnegie, definitely. Crucial for helping humans get along with other humans (and being a good human in general.)

In terms of web design, Don’t Make Me Think by Steve Krug — so important for anyone learning how to build websites.

Last — can I recommend my own book? 😀 I actually wrote Hello Web App specifically to help designers learn how to code and build a startup just like I did! I originally taught myself how to code by cobbling together a ton of Django tutorials for web apps, and eventually reached a point in my programming career when I realized they were all rubbish and I wished I was taught a different way — more visual, bigger focus on the front-end, less focus on explanations. And then I realized that the only way that this resource would exist would be if I created it myself. A year of work later, Hello Web App was born and it’s helped thousands of people learn how to build web apps. Now I’m working on Hello Web Design to help programmers learn design and it should be out in November!

I’m interested in finding out more about your reading habits. How often do you read? In what format?

I love paperback books, but last summer I moved from California to Toronto, Canada and I made the hard decision to get rid of most of my books since shipping was expensive. I mostly read on my Kindle Voyage — I find it super handy for traveling as well as reading in the dark while my husband snoozes. 😛

Also on vacation, I’ll often pop into a used book store to find some silly paperback thriller or crime book. It’s a read to read something physical when relaxing.

In terms of how much I read… with non-fiction, I can read a chapter or two a night before bed. As for fiction, I tend to avoid them unless I have time to devour them all at once. I get super addicted and can’t put them down. My husband and I call this alternate personality “reading monster” — when she comes out, she’ll forgo all other activities in order to read more. So I’ll go a long while without reading fiction until I know I have the time to really dive into them! Thankfully I read really fast so I can get through a normal fiction book in a few days.

How do you make time for reading?

It helps me sleep to read a bit before bed (as long as it’s non-fiction, see note above). I try to get into bed a good 45 minutes before I’m ready to sleep so I have enough time to get some reading in. I also travel a lot, and get a lot of reading in while on planes and trains.

Do you take notes or have any other technique for conquering the torrent of information?

I want to, but every attempt I’ve made has failed, haha. I once bought a set of notebooks so I could note key items and takeaways from non-fiction books. That lasted about a page. Whoops.

How do you choose what books to read next?

Recommendations online, generally. If I see a particular book recommended over and over by friends and folks I admire, it’s a sure buy.

Do you prioritize those recommended by certain people? Is there anyone that you consider a book-recommendations guru?

Nope, I don’t have any person in particular unfortunately!

Last question: what book are you currently reading and what are you expecting to gain from it?

Right now I’m reading Startup: A Novel by Doree Shafrir. It’s a goofy non-fiction book around the startup life, and it helps me look and laugh at my own experiences.

Links where you can follow Tracy Osborn or find out more about her projects:

  • Tracy’s personal website
  • WeddingLovely
  • Hello Web Books
  • Tracy’s Twitter account
  • Tracy @ Medium
  • Tracy’s interview @ Indie Hackers

  • Books mentioned by Tracy Osborn in this interview:

  • The 4-Hour Workweek – Tim Ferriss
  • The Scar – China Mieville
  • Venture Deals – Brad Feld, Jason Mendelson
  • Trust Me, I’m Lying: Confessions of a Media Manipulator – Ryan Holiday
  • How to Win Friends and Influence People – Dale Carnegie
  • When Breath Becomes Air – Paul Kalanithi
  • Startup: A Novel – Doree Shafrir
  • Don’t Make Me Think: A Common Sense Approach to Web Usability – Steve Krug

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