I'll start with the pharmacy story because it captures everything. We were a few weeks into our three-month stay in Tuscany through the Boundless Life program. I had a sinus infection, went to the local farmacia, and attempted to explain my symptoms in broken Italian assisted by Google Translate. The pharmacists looked me up and down, exchanged a glance, and handed me medication for lactation issues. I should have taken Duolingo more seriously.
This is life working as a fractional executive while raising a family abroad. You adapt fast or you suffer the consequences, professionally and pharmacologically.
The Work Side of It
My day in Italy looked nothing like my day in San Diego, but the output was the same. Mornings were for focused work: email, strategic planning, projects. Evenings were for client calls across time zones, because 6 PM in Tuscany is 9 AM in California, and that's when things actually move.
Running client engagements across time zones while also managing two boys and a new country sounds chaotic. It is. But the fractional model actually makes it workable. You're not tethered to one office, one leadership team, or one set of office hours. You're accountable to outcomes, not attendance.
What Parenting and Fractional Leadership Have in Common
I've been thinking about this more than I expected. My kids are 8 and 5. They need clear expectations, consistent presence, and a lot of active listening. So do the leadership teams I work with.
The parallel that struck me most is fostering independence. With my older son Beau, the goal isn't to do things for him, it's to give him enough support and enough space to figure things out himself. The best fractional leadership works the same way. You're not there to be permanent. You're there to build capability, then step back.
Empathy also runs through both. Whether it's helping a kid process a hard day or working with a founder who's exhausted and overwhelmed, the skill is the same: listen before you advise, understand the context before you prescribe.
The Unexpected Upside
Living abroad with clients in multiple time zones forced me to get more disciplined about how I work. I had to be more deliberate about when I was fully present for work and when I was fully present for family. I couldn't coast on availability. I had to deliver in the time I had. That constraint made me better, not worse.
We saw Rome, Florence, Lucca, and Forte dei Marmi. We attended Serie A matches. We ate a lot of gelato, sometimes two flavors in the same cup. We learned that flip flops are not standard Italian pharmacy attire.
It was one of the most demanding and rewarding stretches of my career. Turns out, being curious and adaptable applies just as well to navigating Tuscan bureaucracy as it does to navigating a company's growth challenges. More soon. Ciao.
Matt Greene is a fractional CRO and revenue strategist at Camden Jackson. He works with growth-stage companies on GTM, RevOps, and AI-powered revenue strategy. Get in touch.