50th Year: A Broad — Diary of a Middle-Aged Digital Nomad

Loren Pomerantz
4 min readJul 15, 2017

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What Am I Doing?

Saturday, July 15, 2017–11:10am

“You are so excited, but do you have any concerns?” my friend, Beth, asked as we were being seated for dinner the other night.

“Of course!” I answered, and began listing all the things that still need to be done and the myriad ways they can go wrong. By the time we paid our check, I was only halfway through my list.

On August 27, 2017, three and a half months after my 50th birthday — the day I sent in my non-refundable $5,000 deposit to Remote Year, a program I applied to on a lark after seeing a fun Facebook ad while sitting in my local coffee shop (and I received my AARP card — how the hell do they do that?), I will be embarking on a yearlong trip abroad as the oldest member in a group of 65 millennial strangers with whom I will travel, live and work in 12 cities in 10 foreign countries.

We will be living in each city for one month, where we will work our own remote, digitally-based jobs (mine as President of Combined Forces Public Relations) in a shared office space provided by the company, travel where we like, and live our lives as we each please in apartments arranged for us. At the end of every month we travel together to the next location and do it all over again until August 27, 2018.

So, do I have concerns? Oh My God, do I have concerns!!!!

Most are easy to identify, as they are the practical to-do’s of long-term travel. But as I spoke and was forced to actually think about and articulate each of my worries — things I hadn’t stopped to consider during the whirlwind of applying as one of 600,000 people for 2,000 spots and being accepted 2 short weeks later — I recognized that my concerns about relationships, family, happiness, comfort, health, money, job security and my place in the world were still looming just below the surface, purposely unexplored, where I just may keep them for a while longer: I hate sappy, emotional, navel-gazing, self-help, “feelings” stuff. Ugh.

In the frenzy and exhilaration of anticipation and preparation, I’ve allowed myself to shove all my fears to the back of my overwhelmed brain. But as I methodically check things off my to-do list, making it shorter and shorter and have fewer tasks to occupy my mind, there is an increasing amount of space for those concerns to creep in and take up residence.

Now. I. Am. Freaking. Out!!

It helps calm me to list all that I have accomplished. So far I have: subleased my NYC apartment; told all my clients that nothing will change to their service while I am gallivanting the globe (“but of course I’ll be working East Coast hours!”); gotten a zillion shots to protect me from everything from Typhoid to toe fungus; updated my passport and applied for Global Entry/TSA pre-check; lobbied ExpressScripts for a year’s-worth of prescriptions or else I will end up a wide-awake asthmatic in Bulgaria in December; cancelled the membership to the gym I never go to; cancelled the membership to the yoga studio I sometimes go to; bought all sorts packing cubes to try and organize all the things I haven’t identified that I’m bringing; bought two suitcases on Amazon Prime Day, one of which I’ll return, or maybe both if one of mine seems better; bought a Chromecast and a VPN connection (whatever that is) so I can watch “The Real Housewives of Beverly Hills” and “Law & Order: SVU” anywhere in the world; got a keratin treatment to see if I like it so I can mitigate a bleached blonde Jew-fro in South America; purchased numerous what-if items like a travel safe, collapsible hangers, laundry line, luggage scale, noise-cancelling headphones (did I mention that I’m traveling with 5 dozen millennials?) and countless other things that I’ve forgotten I’ve ordered, but are on their way to me. Phew!

And I’m still not done! I need to pack up my apartment for the new tenant (a lovely woman named Mary who I serendipitously met at The Cornelia Street Cafe, a regular haunt of mine in the West Village, who was in the city hunting for a sublet — I don’t believe in Karma, but I may have to start); cancel my ACA insurance and pray I can get back on when I return in a year; select a travel health insurance plan, which is just as complicated as you think it is; have my mail held; do all sorts of funky, techie things I don’t understand to make sure my phone, computer, bank accounts, etc. work all over the globe; get my Botox and roots done on my last day in NYC for maximum longevity; create the blog on which this post will go; say goodbye to everything and everyone with whom I am comfortable and love.

As these practical tasks continue to move from my ‘to-do’ list to my ‘done’ list, I’m getting closer and closer to that final, only really important, item — and it’s almost time to address it.

Gulp.

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