Cadiz Pirates: All of the July Elevenths

God bless Facebook. This platform has given me so much — the ability to get back in touch with long-lost friends, the ability to stay in touch with faraway and travel friends, and a collection of photos that I treasure.

But I especially love Facebook Memories — looking back and seeing what you were doing one, two, five, or ten years ago.

Recently Facebook Memories gave me such a cross-section of statuses and photos shared on July 11th of every year since 2007, and it made me stop and think. My life has changed so much from year to year, especially when it comes to my career and finances.

I’d love to share these days with you and show you how my life has changed over time.

On July 11th in 2016, I was in Johannesburg. Beth and I were exploring the city in style. We went to the top of the tallest building in South Africa, noting the bullet hole and taking a selfie with a strangely placed nutcracker. We rode the new, modern Gautrain across the city and nearly got in trouble with security for bringing our green juices on board. We got a cheeky Nando’s and drank $9 glasses of Veuve Cliquot in our hotel bar. And just after that, we jumped on a plane to Kruger National Park for a few days of wildlife-spotting.

The good: When you’re able to take your best friend to Africa on business class flights, as well as a stay in one of your favorite boutique hotels in the world, that is pretty much the definitive sign that you have MADE IT. Also, once you’ve gone business class, you’re forever changed.

This trip was also a reminder of how important it is to pick the right travel companions. I happen to love Johannesburg, but I know that most of my non-travel-blogger friends would be scared of it or hate it. Beth is exactly the kind of person who would enjoy it — open-minded, optimistic, and eager to mine a lesser-loved city for gold.

The bad: I’d be in crisis a few days later when a large check I had received for a campaign a week ago had suddenly been recalled. This left a grand total of $40 in my bank account. My bank had already processed and finalized the check, which is what made this crazy; this only happened because the sending bank had been hit by fraud and had recalled all outgoing payments of the last two weeks for security reasons.

Let me tell you, it’s less than pleasant calling your client over Skype on a tenuous internet connection from the middle of the bush in Limpopo Province. “You need to pay me by bank transfer, and you need to do it today,” I said firmly. They complied.

On July 11th in 2015, I was in Berat, Albania. For the fourth summer in a row, I was exploring the Balkans and hitting up some places I hadn’t seen before. I was staying in a nice hotel room for $18 per night and marveling at how the town was dead during the day but hundreds if not thousands of people were out during sunset. I had just spent a week chilling out in the resort town of Saranda; next up was Tirana, a city I would fall in love with immediately.

The good: I was traveling on my own terms. I look back at 2015 as when I was at peak travel — I was earning enough money to go wherever I wanted and didn’t have an apartment to pay for at home, so I was free to spend, spend, spend. I met up with tons of different blogger friends throughout Europe, hit up my first music festival, and even spent a few days with a ghost in Montenegro.

The bad: It felt a little too carefree — and that wasn’t right. I realize that’s a good problem to have. By mid-2015, I felt like I had been eating nothing but candy for the past year. I didn’t want to be the kind of person who backpacks and parties for years on end, chasing the sun and forever hitting on 25-year-olds. It was time to put down some roots. I would move to New York the following February.

In July 2014, I was in London. I actually have no clue what specifically happened on July 11th, as I had no Facebook posts from that day, but I have posts from the surrounding days and can figure out what happened then. I had just gotten home from Slovenia a few days before and was gearing up for Finland next. I was so exhausted from my travels that my London time had been spent catching up on rest.

The good: Major money was finally coming in, and consistently. I had finally cracked affiliate marketing and passive income on a large scale. I was getting paid for several blog campaigns as well. I was still in feast-or-famine mode, though, so I took on as much work as I could. In the past two months I had done paid campaigns in Malta, Ireland, Croatia, and Slovenia; in the next month and a half I would do paid campaigns in Finland, Italy, and Germany, plus unpaid trips to France and Norway.

I could pay for half of an apartment in a nice neighborhood in London and also have money to go out to dinner with friends, to take trips to cool places, to have a life. It had been so long since I had had that.

The bad: This was the darkest and most terrifying time of my life. I’ve been very careful about what I’ve revealed over the years. Part of that is because I deserve privacy. Part of that is because I’m still embarrassed. I’m still not sure exactly how much I’ll ever reveal.

Perhaps it’s best to illustrate with an anecdote from around that time.

I was cooking dinner and accidentally touched my wrist to the broiler in the oven. It burned. Immediately on autopilot, I went to the sink and ran it under cool water. And my only thought was, Please, God, please don’t let him notice that the water’s been running a long time.

It took a lot of time and more courage that I thought I had — but I got out. The only permanent scar is the brown line on my wrist.

On July 11th in 2013, I was in Istanbul. It was my second trip to the city but first trip during the summer (not to mention Ramadan), and it was like visiting a completely different city. I took a ferry to the Asian side for the first time, eating my way through Kadikoy and going to a real hammam with no tourists in sight. I wandered the colorful streets of Armenian Kumkapi. I gorged myself on iftar dinner specials, eating just before sunset to avoid the crowds.

The good: Things felt right. I had been nervous about spending so much time in Europe, but now that I was in Istanbul, it would be time for a lot of cheaper travel. And no more worries about spending too much time in the UK.

The bad: I worried a lot about money. My work was tenuous, and at one point I was owed $9,000 by various companies that didn’t pay on schedule. In the following weeks, I went through one of the toughest work periods of my life — trying to copy-edit a doctoral thesis into British English (!!) in 100-degree Veliko Tarnovo, Bulgaria, a town where I could have internet access or air conditioning, but not both. I chose internet, frantically Googling British spellings while mopping down my face with a towel.

Why had I taken on work like this? Self-employment was feast or famine. I had to take every job I could, when I could, because if I didn’t, I could end up broke. Especially with such a long and complicated trip ahead.

Looking back, I have no clue how I survived before having regular income streams.

On July 11th in 2012, I was in the middle of one of the longest, craziest journeys of my life, from Munich to New York. I had recently done the math and realized that I was about to exceed my permitted six months in the UK over the course of the year. A stern immigration experience after coming back from the Faroe Islands only exacerbated that. So I had to get out after my trip to Munich — but the only place where I could really afford to be was at home in the US.

At the time, the travel concierge site FlightFox had launched and I had a coupon to try them out for free. I had to fly home to my parents in Boston or my sister in New York, so I gave them those options and someone came up with a hellish but very cheap journey: I would have to stay up all night in Munich then get a very early flight to Lisbon, a layover for a few hours, a flight to Toronto, another layover of several hours, then an overnight bus to New York.

My sister had just moved to Hamilton Heights, and I brought her some packaged pasteis de nata from Lisbon Airport. Three and a half years later, I would be living just four blocks away.

The good: I learned one of my favorite travel hacks ever — act crazy and nobody will want to be around you. I spent my spare hour in Toronto wandering around Kensington Market and grabbed a banh mi on my way back. After getting onto the bus, not having slept for 48 hours and praying nobody would sit next to me, it hit me — why was I trying to eat my sandwich neatly? I should have done the opposite!

I hiked up my shirt and stuck my belly out, curving my back like a hunchback. I loudly munched my banh mi and scattered crumbs all over the place. I made my eyes extra big and laughed randomly.

The result? The bus was almost full, but nobody sat next to me. I lay down across my two seats like a cockroach, knees and elbows in the air, and I actually got several hours of sleep.

The bad: I was tough, but that was an awful journey. Staying up all night long followed by traveling all day followed by an overnight bus. An extra-long day due to the time change, plus the extremely long public transportation journey from the airport to downtown Toronto. And to think that I could have done a simple eight-hour direct flight from Munich to New York. Or even a reasonable flight via Dublin or Reykjavik.

And I hated having British immigration constantly hanging over my head. I needed to find a solution, and short of getting married, I wasn’t sure a solution existed.

On July 11th in 2011, I was at home in Massachusetts and plotting my next steps. After my six-month trip to Southeast Asia, I had always envisioned going to Korea and teaching English for a year. Korea is probably the easiest country in which to save a lot of money while teaching.

Things had changed, though. I was making money through my blog. I had an English boyfriend. And on that day in July, anglophilia reigned supreme. I posted about the royal wedding celebrations I attended in England (everyone there had the day off) and the Beckhams had just revealed that they named their baby girl Harper.

I was flabbergasted. The Beckhams gave their older kids names after where they were conceived (Brooklyn in New York, Romeo in Milan, Cruz in Madrid), and I had sworn up and down that their L.A. baby was going to be little Beverly Beckham.

In the coming days, I would decide to head back to Europe, crash with my boyfriend in England for a bit, and head to Austria for the TBU conference. I had no idea what would happen after that — but that decision changed everything.

The good: A few months at home was exactly the rest I needed. Those months in Southeast Asia were among the craziest of my life. I needed time to regroup and feel normal again, especially since I was dealing with recurring stress related to the shipwreck. I also got to indulge in perks from blogging, like a free movie tour in Boston, where I got to bring my friend Lisa along (pictured above at the Good Will Hunting bar).

The bad: I didn’t know if I could sustain it financially. I was winging it. In fact, I would continue to wing it for the next few years. I made a lot of bad decisions around that time, including paying for an expensive flight in order to go to a comped retreat, but at least that taught me what not to do in the future.

In July 2010, I was in hardcore work-and-save-so-you-can-get-out mode. I had already decided I was going to quit the job I hated and backpack Southeast Asia for several months. My tickets had already been purchased — I would fly to Bangkok in late October and come back in May. Nobody at work had a clue. And I had to save up as much money as humanly possible and thus cut myself off from virtually everything.

It wasn’t a completely ascetic summer, though. I spent time hanging out with friends, including a memorable day trip to Maine to eat my favorite seafood chowder and butter-soaked hot lobster roll at the Maine Diner.

The good: I was putting away insane amounts of money each month — and I was the skinniest I have ever been as an adult. The only problem was that I got there by virtually starving myself. I think the lowest I got was around 115 pounds, which for me was both scary-skinny and unsustainable, but I ended up maintaining at around 120-122 or so.

The bad: I was losing my mind. I would wake up at 6 in my downtown Boston apartment, take the subway and two buses to work in the suburbs, spend nine hours at a job I hated, come home, eat a 200-calorie Trader Joe’s eggplant parm, watch an episode of Family Guy, and then work hard on my blog and freelance work until 2:00 AM. I was a wreck and spent my weekends catching up on sleep. I could manage that for a few months at 25 but I know I couldn’t at 32.

The Lessons

It’s so easy to look back and think about the “good old days,” that things always used to be better in the past — but we know that isn’t true. Looking back at these past years, it’s clear that I was always dealing with difficulties even when times were otherwise good.

If I were happy in my life, I’d be struggling financially. Once the money started coming in, my personal life would take a nosedive. And if something in my life started going far better than usual, it was a guarantee that something would go far worse!

If I could talk to my past selves, this is what I would say:

To 2016 Kate: I hate to say it, but in 2017 you’ll still be getting surprised by checks from companies who swore they would pay you by direct deposit. It will be much better once you get a PO Box, though.

To 2015 Kate: Your inertia will soon end. You were wise to recognize it for what it was. I’m glad you enjoyed that trip and even more glad it was your last hurrah of nomadic life.

To 2014 Kate: It’s almost over. You’re about to find out how many people love you, respect you, and will fight for you. You’ll cry when friends you haven’t spoken to for years will tell you that they were praying for you.

To 2013 Kate: Trust me, you’re not going to have to take on projects like that in the future. Just one year until you crack passive income and say sayonara to crappy freelance work.

To 2012 Kate: Don’t worry, you’re never going to have to do a journey like that again because you can’t afford a normal flight.

To 2011 Kate: A lot of people thought you had balls to quit your job to travel the world, but I think this was far more ballsy — barely making enough money to live but deciding to go for it anyway. You made a good choice, and it will get easier, I promise.

To 2010 Kate: Your hard work is going to be worth it. But you already know that. Oh, and it will take you a long time to lose the weight again, but you will, and next time you will do it in a much healthier way.

So where am I now?

My July 11, 2017, was both ordinary and representative of where I am now.

It was a day for Harlem. I dove into a package filled with delicious goods made by Harlem entrepreneurs. I dropped by The Monkey Cup, one of my favorite local coffeeshops, and celebrated their second birthday. I chatted with my neighbors, some of whom have lived on my street for 30 years. I laughed at the sight of a newly thrown out Christmas tree (IN JULY!), so brown and dry it was almost red.

It was a day for work. I planned out my upcoming trip to the Florida Keys, answered a million emails, researched travel plans for the fall, shared a picture of Père Lachaise on Instagram to my just-hit-100k following, and dropped by the New York office of an agency I worked with recently.

It was a day for fashion. I got a peach-and-white-striped romper from my stylist at Trunk Club, literally the first romper I have ever worn since I was a kid, and decided to keep it and wear it that day. And hilariously, a lady on the street in Brooklyn called out, “Hey, you don’t have to strip down in the bathroom!” to me and handed me a card advertising a romper on it that lets you pee without having to take the whole thing off!

It was a day for nostalgia. I got lunch at Panera. Which will always remind me of high school. And if I’m not getting a Greek salad, I’m getting the watermelon feta salad, which they only have during the summer.

It was a day for friends and fun. I met up with a friend I hadn’t seen since college graduation, who himself became a backpacker and traveled the world for a few years. We got oysters and drinks in Brooklyn Heights, then played bocce — my first time ever.

And no, it wasn’t all good. Summer 2017 may have been one of the best work periods of my life, but I was also dealing with a nasty issue behind the scenes on the 11th — the single most malicious attack my site has ever received. An attack that baffled several different tech professionals for weeks and hurt my income. Thankfully, it has since been cleared up.

But that just goes to show that it’s never all good — ever. The important thing is that I’m staying content even when parts of my life aren’t going well. Looking at the past seven July Elevenths, I can see that I’ve grown, I’ve learned, and I’m applying the lessons I’ve learned over the years.

And I realize just how much I have yet to learn. Who knows where I’ll be on July 11, 2018? 2019? 2030? I have no clue, but I know I’ll be okay.