Jessica Stillman, Writer and Non-Pod Person, on Work

Jessica Stillman is a columnist at Inc.com who writes about work, unconventional careers, productivity, leadership, and entrepreneurship. She also writes for Brazen Careerist and Women 2.0, among other fine publications. 

Her Twitter bio urges, “Have a career. Don’t turn into a pod person.” We talked with Jessica about how she managed to do just that, the benefits of quitting, productivity personalities, and the future of work.


You’ve been on this “work” beat for some years now. How did you get into business journalism and writing about work?

When I got out of grad school, I moved out to San Francisco literally because my old college roommate was there. I had no idea what I was doing, and I saw an ad for a blogging position with BNET, which eventually became CBS MoneyWatch. My friends all laughed at me because I had a background in creative writing and literature. So I had a really strong writing background, but I was completely lacking in any knowledge about business.

I really took to it. I liked the pace, the research and learning, I liked the people I was working with. When I moved to London, they offered me a freelance gig. I said, I really like the blogging that I’ve been doing, so let me see if I can turn that into a full-time gig. By then I had a network of editors I’d worked with and went from there. I stumbled around until I ended up somewhere I liked. Here I am! I like it here!

There seem to be two kinds of people — those who have this laser-beam knowledge of what they want to do and others who stumble into something they like.

Some people have a plan for life. My husband, for example, super knew what he wanted to do, and fought tooth and nail to do what he wanted. People worry about that, but for me, it’s trial and error too. You steer warm or cold until you zero in on what you want.

Speaking of career paths, younger people are having a tough time getting good jobs these days. Maybe it’s forcing people to be more entrepreneurial. Do you have any thoughts about the millennial workforce?

I was lucky to dodge the worst of the economic explosion, so I don’t want to speak too authoritatively. But just through reporting and observations — what you’re saying about entrepreneurship, I think there’s just no choice. It has become very clear that there are very few, if any, safe bets. I don’t think it’s laid out in the way it used to be. There isn’t this benevolent system that’s going to shepherd you along.

I don’t want to underplay how nasty an environment it must be to graduate into right now, but also, in some sense, it’s good that people are thinking about it. It’s a silver lining kind of good. At least people are having to make active choices to shape their own path. It leads, in the long run, for some people to a more fulfilling career than if you just stumble into a nine-to-five job that’s alright.

Your experience finding a more fulfilling career involved figuring out hot and cold and trial and error. How hard was it to switch paths?

I was a big fan of quitting. I can’t speak for everyone. People have student loan debt, people have complicated lives — there are all sorts of things that make that hard. I was lucky in that I didn’t have a lot holding me in place. If I had some ramen noodles and a couch somewhere, I was happy. That being said, I usually quit after I’d found something else or another trajectory.

It was really useful to abandon ship, not in a rude or unfair way but in a conscious way, to make choices. That’s how I got from warm or cold. You tack back and forth. Change when things are not working.

I do know people with great results of sticking it out, but they really liked the organizations and that’s the difference. If you really like the organization and the culture, then maybe it’s worth it. But if you feel like, “My god, these people are from Mars. What is going on here?”, then no.

What were the kinds of situations that just didn’t work for you?

I had some copywriting gigs where I would be on a project and someone would have to give approval or something. I knew damn well that I’d be sitting in the office googling what’s going on in “America’s Next Top Model” for four hours, twiddling my thumbs.

You email around, you ask if you can help out with anything, of course you do all of that. I was willing to put in long hours, but I just hated to sit there when I knew I didn’t have to. I had very little patience for that, and I knew I’d be miserable, so whenever I would find myself in those situations I would try to find a way to move out of it.

What about your working style? Writers have to be so disciplined about being productive. Is that a challenge for you?

I don’t struggle too much. [Whether] you like what you do — that’s sort of the x ingredient that people never admit when they talk about productivity. I like what I do, so I don’t find it super challenging. I’m pretty protective of my mornings. I write much better when I wake up than in the afternoon. What would take me an hour in the morning will take me four in the afternoon, so I try not to book things like billing, interviews, and things that could break that time up.

So, one — the fact that I’m doing what I like makes it pretty easy, and two — I have the flexibility to control my schedule, and three —  I’m a bit of a control freak about getting stuff done. Some people are procrastinators by nature. It’s not my personality. I find it so stressful, I’d rather just get it done.

That must be nice. I’m a procrastinator, so sometimes there’s this big disconnect to read and even write about productivity and time management.

It sort of ends up the same place though. When I was in undergrad, I had this roommate who was pre-med, this super-smart, cool girl who just thought I was hilarious because she always waited to the last minute to do everything. She’d have these all-nighters, drinking Red Bulls and going crazy, and I was always the nerd who got the term paper and was like, “Okay! I’m going to start on November 5” and dutifully sit down.

But to be honest, I’m happy with my career, and she ended up being a surgeon, so she’s clearly made it work too. Go with your flow. I don’t know, maybe some people have a real stoner flow — but for most people, working with what you have is better than battling it. I can’t imagine battling yourself all the time.

Are there any interesting trends you’re seeing in terms of how we work?

One of the things I like to follow is this Results Only Work Environment, that trend away from inputs and facetime and more towards just caring about people’s output. Tech makes that a lot easier. You can monitor and communicate, and coordinate and collaborate, and it doesn’t have to be so regimented because the tools are just better than they used to be.

I don’t know if I’d be willing to say that people are actually going there. But I certainly hope slowly but surely people will go in that direction, towards focusing on getting things done and less towards bureaucratic structures and having this mechanistic approach to productivity. I think people are recognizing that for a lot of jobs, especially knowledge work, it’s just not like punch in at nine, punch out at five. It matters less where you are and what hours you’re doing things, and a lot more what your output is.

I hope that’s where we’re going and I do see it cropping up a lot. So fingers crossed, there will be less drab cubicles in the future!