‘We can do this can’t we, Jackson?’

‘Yes, Daddy. We can do this together.’

I asked my son this fairly rhetorical question when he was two and half years old and I was totally lost, trying to hold everything together just five months after his mum’s premature death.

His response, I’ve since discovered, was characteristically him. He’s challenging, often bad-tempered and hot-headed, but he is nothing if not loving, loyal and, ultimately, a team player in this unusual sole parent, sole child dynamic.

Beautifully touching quotes aside, I realise now that we couldn’t manage the sudden upheaval of our acutely different lives without other people’s help. I needed to work, escape, breathe and grieve; he needed to experience childhood, laugh, play and feel joy. It would take a community to raise this child. And it would take time to build ourselves to a position where we felt capable enough to truly take on the world together.

That time came in summer 2018. After dipping our toes gently into the seas of foreign travel without other family or friends – we began with a few days in Majorca in summer 2016, followed by a week in Miami over Christmas that same year – I decided to quit my job so that we could spend the six weeks of the school holidays in Italy together.

Far from being a frivolous decision – one that would see me throw away the most senior and promising position of my career – I knew it was time to make some lifestyle changes. Maybe one day I would have a big job again, perhaps some time in the future I’d be able to afford an Algarve holiday home, but I wasn’t going to make either option my priority at an age when my son only really needed one thing: my time.

On 19th July 2018, we left home and took a flight to Milan for no other reason than the seats were cheap and the plane departed at a child-friendly time. Having been known for taking an Excel spreadsheet on previous holidays – to ensure everything was organised before I set off – it was time to let go of control and freestyle. What happened after Milan would be loose, fluid and, essentially, made up as the days went on.

This flexibility proved key to the success of our trip. I always thought I would be able to anticipate which places Jackson would like best and what he would like doing when we were there. Invariably, I was wrong.

Florence would be too cultural, he would be bored; I was wrong, we stayed another two days.

Rome would be too hot in August, everyone told me not to go; we went out at night and slept in, we got an apartment with a roof terrace and forgot we were in a city during the day, and when the time came, he didn’t want to leave.

It would be a nightmare when we hired a car for the last leg of the trip, he tended to get carsick and impatient at home; the only time he spoke during the three-hour trip from the west to east coast was when he decided to tell me he loved me.

All of the reasons I could find not to do things turned out to be problems that didn’t exist. I realised how much I had avoided living life over the last few years through nothing but undue fear. A lesson I promised to carry with me as a parent who no longer wished to limit his child through unchallenged anxieties or assumptions.

On our first night in Milan, I opted for us to stay in a hostel. Jackson could move amongst an interesting crowd of travelling souls, while helping himself to whatever food and drink he wanted from the open kitchen – an adventure that he took on with aplomb.

That same day, I also gave Jackson his first camera to encourage him to put his beloved iPad away, and observe and document the world around him on his own terms.

Determined for us not to sit still for too long, I asked the hostel manager what was going on in the city that night and he mentioned that a ska jazz band from New York was playing in the castle nearby. It sounded about as alien a night out with a seven-year-old as I could imagine, so we went, took photographs, danced, laughed and ate crepes.

After just one night, it became clear that Jackson was right: we could indeed do anything together.


  1. Hi guys very happy to know your are special times together.
    Benjamin and Jackson having special me time together it priceless.! Im very happy to know that your both bonding and having the time of your lives.
    I pray for continue GRACE AND MERCY COVERING OVER YOUR live journeys and achievement toward GREATNESS …Please remember to write a another book about this new adventure and encourage Jackson to do the same ok … please continues to be the dad you’re to young Jackson and your self.
    Gwendolyn /family..


  2. Your story is inspirational. Having lost a parent at the age of 3, I can relate to a lot of your writing. Giving up your job to give your son more time is an amazing gift. I look forward to reading more. Thank you for using such a talent for writing to share your story.

    Liked by 2 people

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