The Order of Things

I’ve been living with most of the stories here on Winging It for so long that they tend to sort themselves more by theme than by chronological order. But a friend last night reminded me that most people now coming to these stories may not be aware of the chronology and might prefer to start with that so they can build a kind of context within which the stories lie. It makes sense.

There are lots of ways to see this growing selection of stories in terms of beginning, middle and end. But chronology is perhaps the most common starting point, so here we go. I will warn you that there is nothing artful about this piece — it is simply a broad chronology. The rest of this blog is about diving into that chronology, one moment at a time.
I have to think really hard to find a relevant starting point for this body of work. The broadest themes are loss, resilience, and adventure. And though it is not a chronology in the sense that first came loss, then came resilience and finally adventure (far from it) – think of it less as a continuum and more of a ball of twine. But there is a beginning of sorts.
I may change my mind but for me the event horizon that started the long march to Winging It, was 2008 when EMAP and I parted company as employer/employee. I had been working in the business to business division but was asked to return to the consumer part after the acquisition. I really had no interest in doing that so it was a clear-cut decision point. I got a nice pay off, all my EMAP shares vested at the sale and I walked fat and happy. I was happy to be free to explore my own business interests but I was also missing the colleagues and the routine of more conventional employment. The ground beneath my feet felt a lot less solid and it has never returned to that state.
But I was also still up in Stanford, 80 miles from London, where the really interesting work was happening. I made some attempts to find a way to move forward professionally from the living room of the small home Lari and I shared, but I found it hard to get passionate about it. I learned lots of things and made a bit of money, but it was not the most personally enriching moments of my working life.
But on a personal level it was the best period ever. Larissa and I enjoyed a wonderful time living and working together in our modest home. It wasn’t so much that we did anything particularly earth shattering, but for us what did happen was earth shattering. We feel deeply in love despite our differences – we found in each other exactly what we needed and wanted, without consciously knowing what that was. We developed what would become for both of us, the defining relationship of our lives. And we added two other lives into our own in the form of Cosmo and Luna, the whippets. We had no idea what a profound decision that would turn out to be.
In 2010 Lari’s mum was diagnosed with Alzheimers and she went into a home in San Francisco in the following year. In 2012 my own mother died. In 2013 Lari’s mum became quite vocal about wanting us to be closer. What she meant by that was wanting us to mive into her old house and look after her for the rest of her life. Unfortunately, Lari and her mum didn’t get along well at all – there was a lot of bad history there and so it was clear that was not going to happen. But the discussions uncovered the reality that had been previously unspoken — we were ready for a change of life and location.
Long story short, we sold up in the UK and San Francisco and moved to Hawaii with the intention of creating a small eco resort where we could make a sustainable living, sustainably, and look after Lari’s mum until she needed fulltime care.
A little over three months after arriving in Hawaii, Larissa was diagnosed with cancer. For the following six months I became a fulltime caregiver for Lari and her mum whose Alzheimers progressed in a predictable way. At the end of those six months, Larissa died and her mum went into a care home. Only then could I begin to fathom what had just happened. During those six months work on Kipuka progressed and I became more involved after Lari passed and Elena went into care. It was during this time that Luna, our crazy little black Whippet died suddenly of an accident. This brought back all the horrors of losing Larissa and then some. The shock is still with me today.
Development work on Kipuka was completed around late summer 2015 and working out the final wrinkles took me up to Thanksgiving. I put the guest houses up on AirBnB etc in October and by the end of that month, the rest of the year was fully booked. I thought my ship had come in. But then, just as quickly as it had started, it then died off just as quickly and firmly – I was learning about the seasonality of Hawaiian tourism.
I learned about the latest and greatest online and offline marketing techniques and found what worked best for my little business. I also began to make local friends. Amazing friends. But I was also deeply and profoundly lonely. It was nice to meet these new friends, from whom I have learned so much. There was love between us but we were different tribes in different spheres of life. I relied heavily on Cosmo, and my mostly distant friendships to get me through this period.
I met and became romantically involved with a lovely woman in California with whom I share some close friends. We became as close as we could given the limits of geography. As time progressed it became clear that I needed to leave Hawaii as it seemed the only way to escape the losses of Larissa and Luna. I put the property up for sale.
In April 2018 I hosted a hula halau from Oahu lead by kumu Snowbird Bento. This was the highlight of my entire time in Hawaii. It was as if I finally found my purpose there.
A month later the eruption began. It was one of the most stressful things I have ever experienced. Lots of earthquakes, people panicking and driving out with truck loads of whatever they could carry, military vehicles and soldiers watching every road. One by one the local roads were closed.
My romantic partner in California said, ‘get out of there and come here.” I did and it felt like such a relief. Like all my neighbors, I was hoping to be able to go home within a couple of weeks. On June 2 lava inundated the entire village of Kapoho and destroyed Kipuka entirely. No volcano insurance so it was a total loss. The vast majority of my life’s savings is gone. I have gone from being a man with a future, with options, to one who must now focus on whatever I can do to keep from becoming homeless before I die.
Shortly afterwards, things came to a head in California between me and my partner. It was all my fault. I never managed to lose my profound loneliness during our long distance period. I maintained close contact with my old friends and some of those old friendships had been inappropriate considering our relationship and I allowed that to happen. I had compartmentalized my life and perpetuated what had been a way of coping with my extreme loneliness that was inappropriate. This came to a head just before Kipuka was destroyed. I spent five months housesitting and trying to patch things up, but it was clear the cuts were too deep and living in Los Angeles was as isolating for me as had been Kapoho.
So Cosmo and I have now moved ourselves to Italy to reoccupy a home I bought 20 years ago but had left empty for the past five years. We are bringing it back to life and making it into a home. Logic was saying stay in LA and get a job and sell the place in Italy and start again. But I am 58 and the only home I have is this place in Italy. So once again I am doing the illogical and am instead setting up home here for now and trying to figure out what to do next to get my fiscal footing a bit more secure.
So there is the physical labour of breathing life back into this home. But I am eager to shift the focus of my life back to my mind and writing has always been a key part of that for me. So this is where Winging It comes from. This winter is about getting back into shape both mentally and physically and figuring out the near and far goals of rebuilding my life. I both welcome you and thank you for joining Cosmo and I on this journey together.