Hey friends, Hannah here 👋

I wanted to write you a newsletter about how I killed it on stage, about all the business and life hacks we learned, about the networking that was done so smoothly, and how it all translated into better, faster, cooler, newer things for me and how you, too, can apply these learnings.

That’s what you write about off the heels of a week-long conference, right? 🤔

The thing is, I did kill it on stage, I did meet great people, I even learned a thing or two. But that’s not what I took away from this event, nor is it what I care to talk to you about, because those things are inconsequential in the grand scheme.

Let me set the scene: I’m in Sant’Antioco, a village on an island off an island, the island of Sardinia, to be exact. If you haven’t read my previous emails, this is the exact place, give or take 10km, where this very newsletter and business began over a decade ago. This is my first time back, so it feels like a full-circle moment for me.

This morning, after a week of “conferencing”, I took a short stroll by myself along the coast, watching the sun rise high over perfectly calm waters. Two fishermen rocked gently on their tiny, disheveled boat, smoke billowing out of their tired and aged lungs. A lot of people smoke here, an observation.

All this smoking, and yet Sardinia is known as one of the world’s “blue zones”. There’s evidence to say this designation is not always entirely accurate or true for some of these zones, but it doesn’t take long to note the sheer number of able-bodied, older residents here. Smoking, walking, talking, singing, working well into their 90s.

My walk was insignificant - after a week of parties, talks, museum visits, and hugs, endless hugs. On my way back, I passed an old woman’s house. Each time I'd passed her all week while she sat or leaned, smoking outside her home, she'd returned my “buongiorno” with less and less skepticism. She wasn’t there today, and in the absence of her deeply weathered, enigmatic grin, I noticed something I hadn’t prior, something peculiar.

A trophy. A tall, golden trophy cup stood right against her doorstep. An odd place for a trophy, I thought. Perhaps she’s a proud grandmother of a child who won a sporting event in the city whom she wants to celebrate publicly? I don’t know; I made up a few reasons before getting closer, peering over the top of the cup, only to find inside: cigarette butts.

The trophy cup is an ashtray.

I chuckled to myself, immediately curious to know more. Who won it? What for? Was it hers? Had it once been proudly displayed on a mantelpiece, a symbol of someone's hard work, dedication, and success, only to eventually find itself on a doorstep filled with cigarette butts? Was it moved from a position of pride to one of little value after a family feud?

Maybe she picked it up at a market for a euro and simply thought it would make a fine ashtray, but I couldn't help thinking about the irony of it all, having just spent a week surrounded by ambitious people, myself included, talking about our achievements, our businesses, our plans for growth, and what success looks like.

We attach so much meaning to the things we accomplish, don't we? The titles, the milestones, the recognition, the numbers. We work tirelessly towards them, sometimes sacrificing the very things that make life worth living, and then, once we've achieved them, we're already looking towards the next.

And yet, here was this golden trophy, quite happily serving an entirely different purpose.

There's something quite wonderful about that.

In actuality, this is all related to how I killed it on stage, talking about the sunk-cost fallacy, aka the urge to keep pouring time, money, or effort into a failing choice just because you already invested heavily. About how we cling tightly to versions of our businesses because of this, without once looking ahead at our current needs or market changes.​​

Returning to the place where my business began over a decade ago, I notice little has changed. The same roads have the same potholes; the same workers work the same tiny convenience stores; the same gnarled hands knead the same pasta, day in, day out.

But something has changed: this little old lady needed an ashtray.

This island is good at repurposing.

While it has only a few thousand inhabitants, the ground beneath Sant’Antioco is littered with ancient Punic tombs, some of which our group was fortunate enough to visit and enter. One particular site stood out. We explored the history of a community who lived there until very recent times. They had exhumed some Punic tombs of their ancient occupants, clearing out the burial goods, and decided to move in and take up residence themselves. Only in 1985 was the last remaining “gruttaiusu” evicted.

I wonder what the ancient Punic people would have thought of their final resting places becoming someone's living room, or the proud recipient of that golden trophy discovering it filled with cigarette butts.

Maybe they'd be horrified, or maybe they'd somehow find it comical.

But there's something about this little island, where thousands of years of history sit quite comfortably alongside the everyday lives of its inhabitants, that has reminded me how temporary our ideas of importance can be.

Earlier this week, I also visited the exact house where I lived when this business was born, and there, sitting on the balcony, was Assunta, the mother of my former partner and co-founder of Digital Nomad Kit, with whom I shared a home for the better part of two years, all those years ago.

I hesitated for a moment. Should I say hello? Well, of course I should.

"Ciao Assunta! Sono Hannah!" I called, taking off my hat.

She came over to the balcony and beamed down at me, that same enormous smile taking over the bottom half of her face, just as I remembered it. We didn't understand much of what the other was saying beyond that, but she placed her hand over her heart, and I did the same.

And in that moment, I felt so much love.

I suppose some people might find it strange to stop and say hello to the mother of a former partner, but why wouldn't I? We shared so much joy, so many meals, so much pasta, and those memories don't become any less meaningful simply because that chapter of my life has ended.

There are no ill feelings, nothing I wish to reclaim or revisit, just an old affection for a woman who was once an important part of my everyday life, and who, all these years later, greeted me with the same warmth.

I think about the thousands of people who lived and died on this little island before me, who had their own ambitions, worries, achievements, and ideas of what a successful life looked like. People whose names we'll never know, whose greatest accomplishments have long been forgotten, but who undoubtedly lived lives as complex and meaningful to them as ours are to us.

And I think about how, in a hundred years, perhaps even twenty, very few people will remember my name either. So what does it really matter whether I made six figures or seven, whether I spoke on another stage, grew my audience, or collected another metaphorical trophy, if I was too busy chasing those things to enjoy the life I had?

There's something strangely freeing about our insignificance in the grand scheme of things, and something to be said for slowing down enough to appreciate the people, places, and ordinary moments that make being alive worthwhile.

I know that if I stayed here another week or two, my relationship with the ashtray woman would almost certainly progress from a tentative "buongiorno" to a "come stai?", and from there, I mean, the sky's the limit. Maybe I'd eventually be helping her navigate the steps down to her trophy for her morning smoke, just as I found myself helping a woman who must have been nearing 100 put on her jacket at the marina this morning.

And I wonder if, when all is said and done, these are the moments that will have mattered most. The small kindnesses, the unlikely friendships, the people we made time for along the way, none of which will ever appear on a list of achievements, but all of which make for a life worth living.

I think that's what I'll take away from this week, and what I want to share with you. Things change, we change, our businesses evolve, relationships end, and the things we once held so dear find new purposes, sometimes ones we could never have imagined.

We can let go of what was while still honoring everything it meant to us. We can look back with pride, gratitude, affection, and reverence, without needing to recreate it or cling to it forever.

And there's something rather beautiful about knowing that what once was will never be again, but that it existed at all, that we were here to experience it, and that some part of it will always live on in us.

Not another business strategy or a shiny new opportunity, but a reminder that success is ours to define, redefine, and even repurpose as we go.

And that sometimes, even a trophy makes a perfectly good ashtray.

Hannah

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