How I Kind of Tried Frank Sinatra’s Vagabond Shoes on for Size [Ice Cream Sundae]

Willem van der Horst
Ice Cream Sundae
Published in
8 min readFeb 20, 2016
Image credit: Tobias Wutzow

I hope you had a great week and that you’re enjoying the weekend. I’m still in London, I’ve been working on some client projects, looking for new clients, meeting interesting people, attending inspiring events at the Google offices and recording several fascinating interviews for the Ice Cream for Everyone podcast (watch out for new episodes coming soon!).

I’m looking forward to a change of scenery now; I’m flying to Prague to speak at the European Planning Conference next week. I’ve never been and hear it’s a beautiful city. I’m preparing a crossover of two of my favourite topics: table top games and strategy.

Talking about wanting a change of scenery, let’s get to our main story. As you may know by now, I was born in Long Island, New York. I lived in a town called Port Washington until the age of 6 years old. I generally say I’m only technically American. After moving to France, those early days have become hazy memories and images, like that of eating Flintstones vitamins.

When I was 19 years old going on 20, I decided the cinema studies I was pursuing weren’t all that interesting. What I really wanted to do was go to the United States, to go make it big in New York. I thought I’d explore where I was born. I had vague ideas I’d study. Ideally someone would suddenly discover my incredible though as yet undefined potential and immediately offer me bucket loads of cash, or maybe I’d end up cleaning dirty dishes in a restaurant. The possibilities were endless and paved with glory.

If you think it sounds like an ill-advised plan, you’re probably right.

It had the merit of being a very simple plan: Step 1 — fly to New York.

That was it.

I’m not sure what my parents really thought about it but they supported my trying to fly out of the bird’s nest directly across the pond for my first test flight. As I remember it, my mom thought it would be a good idea to add a second step to the plan. She contacted an old friend of hers and asked if I could stay at her place after landing, while I figured out what I was doing. I only realised much later that staying in her apartment in the heart of Greenwich Village was pretty exceptional, as was her house in the Hamptons.

As I mentioned, I had a vague idea about studying, though I wasn’t sure what and of course had little money to do it. I was probably told how expensive studying in the U.S. and probably hadn’t listened. I had saved some cash from scooping Häagen-Dazs ice cream and bartending at the TGI Friday’s in Paris, so of course I felt entirely qualified for whatever The Big Apple would throw at me.

I can work in the U.S. because I have citizenship, though I hadn’t realised the amount of fun it would be to take care of paperwork for my social security number. I spent quite a few hours waiting in government administrative buildings. I also had to go back to North Hempstead, to get a proper copy of my Act of Birth. It took weeks.

I walked around Manhattan a lot. All the way down to Battery Park to take a look at Lady Liberty, and way North of Central Park, around Harlem, and from Alphabet city in the East to the Upper West Side.

I went to see the new Star Wars: The Phantom Menace several times. The movie was released just a few days before my twentieth birthday.

I tried all the foods I’d been looking forward to like crispy slices of New York pizza at the famous original (now defunct) Ray’s Pizza at 6th Avenue and 11thStreet, hot dogs at Grey’s Papaya at the now closed mid-town branch on the corner of 8th Avenue and 37th Street. I also strengthened my stomach and immune system buying hot dogs from street card vendors. Embarrassingly I just didn’t know about excellent delicacies like Reuben sandwiches and somehow didn’t find out until much later. I’ve never been to Katz’s Deli or any of the other famed NY delicatessen establishments. Now I think about it, it’s a good reason to go back.

I kind of knew that I was underage for drinking alcohol beforehand but hadn’t thought it would affect me. That’s until I wanted to have a cold beer somewhere after walking around the New York summer heat for a while. When I was asked for ID I found it extremely annoying, particularly given I’d spent the past six months bartending until 3 to 4am before going out for a late dinners and drinks with colleagues in Paris. I felt relegated to being a second-class citizen.

I remember showing my passport to a bouncer somewhere — I think it was a jazz club, possibly the Blue Note; I wanted to go see some live music. He looked at me with bewildered eyes when I said I didn’t have a drivers’ license and he wouldn’t accept my passport as valid proof of age, despite my trying to explain that surely an internationally valid legal document should be good enough for the establishment he was guarding the door of. I remember that ironically put a damper on my spirits. I tried watching TV instead of going out but found the ridiculous amount of advertising made it impossible to watch a show, and that was in 1999, I imagine there is even more now.

I remember going to check out the Jekyll & Hyde Club, probably the first place I’d wanted to work at. I loved the weird and wonderful atmosphere, the hidden bookcase doors, the theme park vibe. Of course given I didn’t have my social security number sorted, they didn’t want to hire me, gave me the same kind of look the bouncer had given me when showing them my passport. I handed CVs around to various restaurants in Manhattan, thinking my TGI Fridays’ bar experience would be worthwhile.

I wasn’t having much luck walking around the Upper East Side one day, giving out CVs at French style restaurants. Until one manager of a casual bistro offered me to try out for a dinner service. Most of the staff was French. I thought the kitchen was a bit too dirty and cramped. I just didn’t like the vibe of the place and said thanks but no thanks. After trying it out I also reconsidered the idea of working in a French restaurant, while it seemed like a good idea at first, on second thought being with French speaking people I wouldn’t be improving my English as much.

By then I had also enquired into university courses and realised just how expensive they were. I had put the idea of studying to the side, and needed to find a way to make a living first. This whole moving away to New York was appearing a little more complicated than I initially thought it would be.

My host was spending most of her time in the Hamptons; she explained that she had guests coming from the city and visiting the house every weekend, they had rented rooms for the weekends and hung out there like a summer-long weekend away programme. Apparently it’s a normal thing to do in New York, for people who have the means I guess. Probably seeing me a little lost, she invited me and said I could help with doing cooking and chores around the house while guests were there.

So I took the rickety Long Island Railway train from Penn Station to go and hang out in a big house in Southhampton with a bunch of forty-ish year old mostly divorced people. They were great, it’s just that it was both nice and weird to be 19 and hanging out with people about twice my age. I marinated and barbecued meats, made dinner, and they loved it. I did my best to be useful around the house and entertain them.

I particularly remember the weekend when John F. Kennedy Jr’s plane crashed in Martha’s Vineyard. Everyone was upset and watching the news, while I genuinely had no idea what was going on or who this person was. I remember making a snarky remark that was meant as a joke. The teary people on the couch in front of the TV shot me death looks. Not the right time for my smartass comments apparently.

Another time, the guys tried to explain baseball to me. I still don’t understand much of it, nor have I ever had much interest in understanding, I have to admit. I went back a couple of weekends. I explained I was looking for work and one of them owned a big discount supermarket in Jamaica, Queens, he got me a job stocking shelves and helping around the shop. The kind of old places where you can anything from toys to DIY tools and discounted packs of m&m’s. The offer was welcome, I said yes.

That summer was a study in contrasts, from Greenwich Village, to the Hamptons, to commuting to Jamaica, Queens for work. The manager was a pretty old, thin, white haired, wrinkled, and tough as nails type of guy, one of the only other white people around. I was working with Haitians who spoke creole French. It was a bit of a derelict I remember this one guy with a thick accent I barely understood his stories. I can’t remember his name, but I remember the golden incisive he had with a cannabis leaf embossed on it. We’d slip out and go smoke pot behind the store in the delivery parking area.

At one point a friend and ex-colleague from TGI Friday’s Paris came to visit, we went to check out some more TGI Friday’s in NYC and I showed him some of my walking circuits. The same person who hired me to work in Jamaica let us stay in their bachelor pad in Tudor City for a few days.

After about 7 or 8 weeks and several calls and visits to the government building my social security card was finally ready. I realised how much I was holding on to the goal of getting that done when I received it. I’d tried a few different jobs and the idea of going back to finish my studies in France where I could afford to sounded more attractive. I felt far away from home, I missed my family and friends in Paris. I wasn’t enjoying struggling in New York for the sake of it all that much any more.

I talked about it with my parents on the phone. After much consideration, I thanked my host and her friends for all their support and organised flying back home to Paris. I was both disappointed and happy to come back. I wasn’t happy about failing in New York (at least I considered it a failure, even though success measures were vague at best). On the other hand it was an amazing experience; I had no regrets as I flew back home to Paris.

I just came across the last episode of This American Life podcast and it’s about different people taking a leap into the unknown, it was fascinating, check it out.

If you enjoyed reading this, please forward it to a friend! If you know other people who would enjoy it, they can sign up to the newsletter here.

Thanks!

Willem

This newsletter was originally published via email on the 22nd November 2015. You can also sign up to receive Ice Cream Sundae on the Ice Cream for Everyone website.

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Willem van der Horst
Ice Cream Sundae

French/American playful brand strategist, tabletop gamer, skier, and traveler. Check out the Ice Cream for Everyone Podcast & Sundae newsletter on my website!