We tried again a couple of years later. I had rolled through another couple of roles at this point, including a global position at a new firm which I had thought would cure my longstanding wanderlust. I left that business after a couple of years, having been made to ‘restructure’ my sales team deeply as part of a merger with our parent company (code for firing lots of people) and I was feeling pretty burned out. I restructured myself out last, like the Captain leaving a sinking ship right? Or the last drunk out of the dive bar. I thought I’d like a bit of a break from business.

At this point it felt like the right moment to dust of the old escape manual again. This time we had Australia in our sights. It would be an easy move. We had a gang of friends there, it was an English speaking country, their medical system was compatible with ours so Menna could find work. They had epic surf, great food, awesome wildlife and a healthy outdoors kind of vibe that felt like the antithesis of our urban life at this point.

The plan was contingent on Menna this time. She would be the breadwinner, inserting herself into some high powered paediatric role maybe in Melbourne Children’s Hospital. Visas would be thrown at us and I would ride along as the plus-one.

Maybe I would find work out there, but then again maybe I would not. I had long been nurturing a secret fantasy where I became a ostensibly a stay at home Dad, but used the hours of free time while the kids were at school to 1) secretly do a PhD and then make everyone call me Doc. 2) Set up a series of extremely low-effort but highly lucrative business which would pretty much run themselves. 3) Become fluent in Mandarin and various South East Asian dialects which I would learn via flirtatious chat with our attractive polyglot Filipina nanny. 4) Become an online chess hustler.

While I could see no obvious flaws to the plan, it unravelled nonetheless. We were undone this time by the twin forces of bureaucracy and boredom. The Australians wanted to stem the tide of disaffected doctors who were streaming off that rusting old aircraft carrier that is the NHS, and seeking a life of sunshine, reasonable hours and decent pay in the Southern Hemisphere. They had put in place several administrative hurdles that were guaranteed to delay any job application for at least a year. So we gritted our teeth and filed the paperwork needed to get Menna’s certificates and qualifications translated into the Australian vernacular.

In the meantime however I had got bored. A couple of months of ‘finding myself’ involved doing morning yoga with lots of old ladies at the David Lloyd, drinking kale smoothies and listening to podcasts on poetry. It was winter and no-one else wanted to play. Even the kids were absent most of the day at school before coming home to participate reluctantly in various elaborate projects I’d dreamed up in their absence.

After a few months of this I’d had enough of kicking around so I set up a company (Outlaw Strategy since you ask) and prepared to kick off the first of my low-effort high-reward side bets. A consulting business requires no upfront capital, no equipment and no assets other than an ability to look smart, weave a sharp story and use arcane business jargon proficiently. I have this in spades.

My first gig was a three month strategy project, advising a fast growing research firm on how to structure their commercial team. It was a fantastic company, well run and full of smart people who basically already had all the answers and were dying to tell you so. I travelled around all their offices, interviewing the troops and synthesising their wisdom. Stir it all up, sprinkle a few insights, some infographics, a gant chart or two and a pinch of business homilies, then prepare to ping over your invoice and ride off into the sunset. Consulting is the FUTURE I thought to myself.

Somehow they pulled a fast one on me though and before fully thinking it through, or even really getting Menna’s sign-off, I’d somehow accidentally signed a contract to become their Head of Sales. I was now on the hook to implement the convoluted strategy that I had cooked up, which, I now realised, was highly ambitious and overly elaborate. I had also committed myself and family to relocate to New York the next year.

Australia was off.