Last weekend, my partner Kelly and I took a weekend road trip through Italy and were plotting a course to Turin from Lucca, a charming old walled city near Florence.
Consulting the map, we opted for what appeared to be the coastal route, which snaked along the coast to Genoa before heading North to Turin.
We imagined the route passing through numerous quaint seaside Italian towns, one of which we might stop in for coffee, another for lunch, another still for an afternoon stroll and croissant.
The idyllic road trip itinerary in other words.
Filled with excitement, we locked the route into Google Maps and hit the road.
It didn’t take long to realize, however, that our excitement had been misplaced. Because barely 30 minutes into the drive, our route directed us onto a massive 8-lane tollway.
The highway was impressive in its own right and promised a smooth and efficient trip back to Turin.
But that efficiency was not without its cost.
In our case, that cost was the seaside towns and coastline we had imagined ourselves spending the day winding through.
My heart sinking, I asked Kelly to see if there was any other route we could take.
It turns out, there was just one, perhaps the polar opposite of the route we were currently on.
The Trade-Offs of Efficiency
The alternative route consisted of a tiny, one-lane road filled with seemingly infinite switchbacks that would add three hours to our trip.
And yet, one look at the squiggly line the road cut into the map told me this was the road we were looking for.
If there’s one thing I’ve learned in years of traveling by foot, by bike, and by car it’s that the winding road is always the one you want.
No, it’s never as efficient as the alternatives, and yes, it takes you much more time, effort, and even stress to get to your destination.
You need to leave earlier, stay on the road longer, and there are always more than a few hair-raising moments passing opposing vehicles while winding up narrow roads with no guard rail between the pavement and a precipitous drop.
Despite the obvious downsides, I’ve yet to take a winding road that wasn’t worth it.
Because what these roads lack in efficiency, they make up for (and more) in discovery, awe, and invigoration.
This is as true when charting a weekend road trip as it is in charting our creative lives and careers.
The Winding Road to Original Work
In our work, we tend to perpetually strive for the most efficient route to our end destination.
And we don’t have to look far to find them.
We can merge onto the highway and join the stream of traffic following the latest trends, committing fully to whatever content, formats, and platforms are hot in the moment.
Done skillfully, we can make a good career of this.
But the toll is steep.
It requires us to give up much of our originality, creating generic, often commoditized work for which there is proven demand, forgoing our creative instincts, curiosity, and fulfillment in exchange for efficiency and predictability.
Not that there’s much creative inspiration to be found on the highway in the first place.
What’s more, in seeking out the most efficient route through our lives we forget that the only true end destination to which we are hurtling is death.
Surely we’d rather take a more scenic—if at times challenging—route there?
The Destination Is Not the Point
That winding road will be full of switchbacks, wrong turns, and dead ends.
We’ll deal with more than a few hair-raising near-misses, landslides blocking a previously navigable road, and time when we’re so far off the map our GPS loses signal and we’re left to find our way forward through instinct, hunch, and experimentation.
And yet it’s undeniable that this route is infinitely enthralling, invigorating, and life-affirming.
It’s also the type of road with the best chance of leading us somewhere interesting.
When traveling this road we don’t always know what the end destination will be.
But then again, on winding roads, the destination is rarely the point.
And in fact, ending up somewhere entirely other than where you imagine when you left might just be the greatest gift the road could give you.
Explore how to navigate a creative life that matters
This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.
A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.
Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”
It’s something I’m proud to create and I’d be honoured to share it with you.
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