A career in transition: 5 questions for Gina Trapani

I've been thinking a lot about time management and productivity lately, so I decided to check in with Gina Trapani, who is best known as the founder of Lifehacker (one of the most highly trafficked blogs in the world), and the author of the book "Upgrade Your Life," an indispensable guide to how to work smarter in the digital age. When I last interviewed Trapani, she was still editing Lifehacker, which is owned by Gawker Media. She left that position in January. These days she divides her time between computer programming, writing for her personal blog, Smarterware, and freelance writing for a variety of publications.

We chatted via phone and email about going through transitions and forging a new path away from a brand you've been closely identified with. The following is a condensed version of our conversations.

So how does it feel to be just Gina Trapani after four years of being Gina Trapani, editor of Lifehacker, where you had one of the most powerful voices in the blogosphere?


Lifehacker is this great brand, packaged really nicely and my name was tied very closely with it. Now that I'm not there, I'm not a brand anymore. I'm human, and I don't know if I want to create another thing that sums me up in a sentence. I'm kind of enjoying not having that one thing right now. Eventually I'll find another new singular focus I want to stay with long term.

There is this expectation that you'll be doing this this huge great thing which will be as good as the last thing you did. And right now I don't have that next big thing yet. I'm taking a break. Noodling around. Exploring. It's like that saying that turned into a book title, "Once You're Lucky. Twice You're Good." There's a bit of a "now I've got to top this," feeling. That all said, because I wrote the book and because my name was front and center on Lifehacker for so long, people still want to talk to me even though I'm not the front door to coverage there anymore.

You recently wrote about why it's a bad time to be an employee and a great time to strike out on your own. I know you got a little bit of push back on that. Tell me about that.


There were some people who said I was giving irresponsible advice. And the whole thing does change when self-employment is not your choice. My argument is that we're all sort of free agents in some way. You and I are constantly pitching our work somewhere. But even as an employee, you have to market yourself and embrace the idea that you have to build your reputation, sell what you have to offer. My sister is an executive at a big nonprofit and everything she does is always within the firewall of her organization, where she has been for 15 years. I ask her: "What happens if you are suddenly not there there? How are you going to advertise what it is that you do and what you did there?" My parents held jobs at the same companies for 30-40 years and that's just very rare today. So I do believe that even employees have to have the free agent mindset to some degree. Like Robert Scoble, who worked at Microsoft and created an incredible reputation for himself by blogging about Microsoft. I think the people who are best situated are those who can establish themselves as experts even while they are employees.

We spoke a bit about this transition process feeling like you're being marinated. What role do you think these kinds of marinations play in a career?


My friend Michael Barrish wrote this great post about cycles in life. You have a good thing. Then it turns into a rut. Then you go through a transition. Then you find another good thing. Lifehacker was a great thing. Then it turned into a bit of a rut. I did all that I needed to do there. And now I'm in the transition before that next good thing. What does it mean to be there? As a free agent, I'm constantly making decisions on whether to take on a job or assignment, whether to go to a certain conference, whether something is worth the money. Before it was clear when I should do something because it would be good for Lifehacker. I find this kind of decision-making tiring. But it's like a woodworker whittling away the stuff you don't need to reveal what's underneath. And making these little decisions, the chipping away, is going to lead me to whatever my next thing is.

As you make these decisions, how much of your decision-making process comes down to money?
I planned my transition 6 to 9 months ahead of time, so I built a financial cushion before I took the leap. I also lined up a couple of gigs that bring in a bit of money every month -- not as much as I was making, but enough to float for a year or two with the cushion. Given that, I can decide whatever else I want to do with the rest of my time. Money definitely comes into play in those decisions, but thanks to my cushion and regular gigs, it's not the end-all and be-all deciding factor. That's a beautiful bit of freedom. I don't recommend quitting your regular paycheck without a safety net like this. The last thing you want is to sweat the mortgage payment every month and take any job just because it pays.

There are three main factors I consider when deciding on whether to take a contract: how much I love the work, how much I'd learn from the assignment, and how much they're paying.

Someone asked me if I was available to do some software development and told me name my rate. I half-joked that the more interesting the job was, the cheaper I'd be. If it's really crappy work, then I'm either going to charge a lot more or not take it at all.

Now that you're living in free-agent-land, what are you missing about employment?

I miss working with a single team toward a single goal every day, like my editorial staff at Lifehacker. But now that I've got a few contract gigs, I get to drop in and make a cameo appearance on a couple different teams during the week instead of being in a recurring role on one every day. That's nice, too, because when you do show up, everyone's happy to see you.