9 to 5

Two years ago, when I first announced my plans to work remotely while traveling, I was met with a healthy amount of skepticism. Among my favorite reactions was one from a woman who worked for the PR agency my employer had retained.

“How are you going to do that?!” she scoffed.

It was a pretty ballsy reaction considering that I was her client. The company I worked for paid the agency she worked for tens of thousands of dollars each month to help us shape our media relations strategy and advise us on matters related to PR. Questioning my life choices wasn’t really part of the remit.

I shrugged. “I’m going to continue to keep east coast hours, so you probably won’t even notice a difference,” I explained. “I’ll still be online and taking calls – I just won’t be available for in-person meetings.”

I would have thought this would be good news. No one wants to have more meetings – not even if they’re with me and I do my best to keep them interesting. In fact, the last time I met with this woman, I had forgotten to bring my dress shoes along and was thus forced to wear my walking shoes, which were a pair of Crocs.

“That sounds difficult,” she replied.

“Well I’m going to try,” I replied. “No harm in trying, right?”

She looked unconvinced – as so many other people did when I shared my plan. Not like any of that mattered. Last time I checked, I wasn’t paying anyone to give me career advice.

Cape Town needs no filter. #capetown #tablemountain #nofilter

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As it turned out, working remotely wasn’t very difficult. In fact, it was far easier than I expected.

Every day, I spent the first eight hours doing whatever I pleased: hiking Table Mountain, riding a Segway, feeding a seal by hand… whatever. Then, in the early afternoon, I signed online and did my job, just as I had back in New York. The only thing that was different was the location of the kitchen table from which I was typing emails.

My life was every bit as fun as it sounded and, within just a few weeks, I noticed something interesting: Once I started enjoying my off-time, my work-life was a lot more bearable.

That, in case you’re wondering, is how you do it.

Simply had to. #durban #southafrica

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I’d love to tell you that after two years on the road the naysaying has subsided, but it hasn’t. There is no shortage of people who still point out how difficult or lonely or dangerous my life seems to be. I don’t pay them much mind. They’re not right and even if they were, it’s not their problem to solve.

Lately, the thing drawing the most skepticism is my ability to get an EU visa. This is “complicated,” people tell me. And, actually, they’re right. I know, because I’ve looked into it. But many people seem to think that complicated means “impossible,” and on that point, they’re wrong.

It’s not impossible, and even if it was, what’s the harm in trying? I’m the only one wasting time and effort on a pile of paperwork.


This, by the way, is the stuff self-help books are made of. Make fun of them all you want, but they’re helpful. I consider it an asset that I have, for the most part, trained myself to be practical, proactive and resilient when it comes to setting and achieving goals.

And so it was with a great deal of irony earlier this week, that I decided submitting an application to The New York Times was pointless. As I re-read the job listing, I came to the conclusion that the editors already had a person in mind for the role. The posting was but a formality. It didn’t matter how good my application may be, I wasn’t going to get the job. I wasn’t even going to be in the running.

This is a convenient way to think when you don’t exactly like what you’re turning in. Even after so many of you gave me really incredible feedback and advice, I don’t think my second attempt at my application essay was any better than the first. To be honest, I wouldn’t hire me based on what I turned in.

I would have loved to work on it a little while longer or pick a new topic altogether, but there was no time for that. Deadlines are deadlines and I submitted it just the same, imperfect as it was.

Not like it matters, I told myself. You never had a chance anyway.

Once again, I didn’t see the harm in trying. Besides, I guess there was a tiny part of me that wondered if this really was an open position – and if so, would the NYT consider filling it with someone whose cover letter was way better than her actual writing sample?

But the better, more practical side of me knows that submitting the application was symbolic. Sometimes it’s important just to admit what you want. I haven’t applied for a job in more than four years. To finally find something that sounds exciting is not nothing. In fact, this whole process has given me a big clue about what I should be working towards.

The real question now is: How am I going to do that?


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My sincerest thanks to everyone who commented or emailed their feedback on my original Helsinki piece. Your edits were so thoughtful and insightful – and the vast majority of them are things I can apply to everything I write. If you want to see how the piece turned out, you can find it pasted below the original, here. While it’s already been submitted, you’re welcome to share any additional edits… because there will be a next time!

Finally – this post was inspired, in part, by Farm Girl Miriam, who recently wrote about how to respond to people who question her life choices about everything, up to and including the number of birds she owns. I am not bird person, but she is and that’s cool with me.


  1. I love the rewrite! Especially the bit about the rickety ladder held up by a clothesline, and the point you make at the end “while every place is interesting, it’s up to the visitor to find out how”. I can think of worse words to live by.

    • Well thank you! As I mentioned, I do not like it, but it is what it is at this point. I’m glad I tried… I’m glad I realized there’s something that I want. (Unrelated: I would also like to go back to NZ!) Anyway, thanks again for reading and the feedback. I appreciate it!

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