It’s an honor for me to be able to present this interview I did with Lifehacker editor Gina Trapani, one of my personal blogging heroes. Gina was one of the bloggers who inspired me to start Zen Habits, and she continues to set a standard of excellence to which I aspire to meet with each post.
Gina recently published the second edition of her Lifehacker-in-print book, Upgrade Your Life: The Lifehacker Guide to Working Smarter, Faster, Better
In this interview, Gina reveals her top three productivity tips, what it was like at Lifehacker in the early days, how she wrote her book while writing and editing a massive blog, and her plans for the future. I hope you enjoy it as much as I have!
Leo: Your book is kind of a lo-fi version of Lifehacker, and I’m sure it’s helping a lot of people who never read your blog before. What are you most proud of about the book, and what have people seemed to like most about it?
Gina: The book is a good introduction to Lifehacker for people who don’t read blogs, and people who are less technically savvy that our daily online readers. It highlights our best material in a structured way. The reverse chronological format of a weblog is great for news, but not good for articulating a hierarchy of ideas, even with categories and tags. Each chapter of the book is dedicated to a digital productivity issue–email overload, document organization, attention management, portable work–and contains a specific solution to a problem (like keeping your inbox empty, or synchronizing files between work and home). The book encapsulates the spirit of the web site–which is this daily, ongoing conversation–in a handheld volume. Since web sites are this ephemeral thing that are hard to capture, I think readers really like having something they can throw in their backpack, flip through, reference, and show to their friends and family.
Leo: Writing a book while blogging and editing a top-ranked blog must have been a great challenge even for a productive person like yourself … tell us how you were able to firewall time for book writing.
Gina: It was a difficult challenge, probably the hardest I’ve ever worked in my professional career. During the heat of the process I wrote through nights and weekends, without much free time at all. I got the 
book-writing done by breaking it down into hour-long sprints. I used a kitchen timer and would set it for 60 minutes and write like mad, without getting up or stopping the whole time. My timer beeps once when there are 10 minutes left and twice when there are 5 minutes left, so I was able to wrap up whatever I was working on in that session. On good days I’d do 3-5 sessions like this throughout the day, on bad ones none. Over time I had a good read of how many hour-long sessions would produce a single hack, and a single chapter, so I was able to plot out my schedule in time for my editor’s deadlines. I actually enjoyed blogging more during the book writing process because I can get a few posts published AND get feedback in an hour!
Leo: What was the “ah-ha!” moment for you, when you started to become more productive, to use lifehacks, to use technology as a productivity tool?
Gina: It wasn’t a singular ah-ha moment for me–it happens whenever I fall off the wagon, regroup, and then see results. When I’m thinking about these things and applying them to my daily life and they work, I go, “Ah ha! See? If I always did the right thing…” Problem is, I don’t follow my own advice as much as I could. :) But, whenever I get an email reminder from myself to do something I would’ve forgotten about had I not set it up, whenever someone says “thanks for getting back to me so quickly,” whenever I see progress on my personal projects … these are the times when I realize (again) that better habits and overall mindfulness works.
Leo: By the time I started reading Lifehacker, it was already huge. Tell us about the early days, when you had only a few hundred readers and you built it into the powerhouse it is today. How did you accomplish that feat?
Gina: The first few months of Lifehacker were a lot of fun but a lot of work. Today I’ve got a staff of 4 writers, a copy editor, and an intern all working together. Back then it was just me writing a dozen posts a day and reading and responding to all the email we received. It was great because I got to form personal connections with a smaller reader community. Since Lifehacker was my almost full time job from the beginning, I had most of the day to read, think, and write. The concept of life hacks was still very new, still something people were exploring in interesting ways. (Today it’s become a way overused and hackneyed, and I take some blame for that!) Since Lifehacker is published under the Gawker umbrella, the power of the network really helped me grow the site’s audience. That backing freed me up from worries about design, ads, traffic, or technical problems. I just got to write, and I focused my energy on producing the best content I could. That’s the best thing any new blogger can do.
Leo: How do you not get into a rut? You write about the same topics every day, for at least a few years, and you manage to keep things fresh and interesting.
Gina: I try to always think about and experiment with new ideas, post spins, publishing formats, and coverage areas to stay out of a rut. Since we cover software and webapp releases and upgrades, we always have something new to write about as it relates to the “same old” productivity topics. Over the years we’ve expanded our coverage to DIY projects, various operating systems, and interesting platforms (like Firefox and the iPhone).
Leo: What do you see yourself doing in five years? What are your biggest dreams, now that you’ve achieved such success?
Gina: In five years I see myself doing the same things I am now–reading, writing, teaching in some form, and making things online. I’m not sure where or in what context exactly; I’ve got to leave some things to chance. My biggest dream? To be doing it smarter and better than I am now.
Leo: You’ve written about hundreds of productivity tips … but if you had to share the top 3 tips from your book, that you use every day and that do the most for your productivity, what would they be?
Gina: When I’m fully committed to using them, my three-folder system for managing email, my online calendar “tickler file” for reminders about stuff I need to do later, and my “doable to-do list” all save me from inevitable productivity meltdown on a daily basis.
To read more of Gina Trapani’s productivity tips, visit Lifehacker or buy her book, Upgrade Your Life: The Lifehacker Guide to Working Smarter, Faster, Better.