I spend a lot of time on planes these days. Most flights are fairly predictable. I answer emails, review documents, work through presentations, catch up on sleep or simply try to adjust to whichever time zone I’m heading towards. After a while, the routine becomes familiar. Airports start to blend together and entire journeys become surprisingly forgettable. Every now and then, though, there is a moment somewhere in the middle of a flight when the laptop is closed, the cabin is quiet and there is nothing particularly demanding my attention. Those are usually the moments when my mind starts wandering.
It happened recently on a long-haul flight. I found myself thinking about how different my life looks from the one I imagined when I was younger. Not better or worse. Just different.
When we’re young, we tend to create fairly detailed stories about our future. We imagine where we’ll live, what our careers will look like, who we’ll become and how life will unfold. Even when we know plans can change, there is usually an underlying assumption that the broad outline will remain intact. We believe that if we work hard, make good decisions and stay focused, life will generally follow the path we’ve mapped out for it.
Looking back now, I smile at how much confidence I had in a future I knew so little about.
The life I imagined for myself and the life I eventually built have far less in common than I would have expected.
There are obvious differences. I never imagined building multiple businesses. I never imagined splitting my life across different countries. I never imagined that entrepreneurship would become such a significant part of my identity. I certainly never imagined many of the challenges, opportunities and unexpected turns that would shape the years that followed.
What surprises me most, however, is not how much changed. It’s how many of the things I once considered detours ended up becoming defining parts of the journey.
When we’re younger, we tend to think of life as a sequence of carefully connected decisions. One choice leads logically to the next. Looking back, my experience feels far less structured than that. Some of the most important moments arrived unexpectedly. Some of the people who had the biggest impact on my life entered it without warning. Some of the opportunities that changed everything began as conversations that seemed completely ordinary at the time.
If someone had shown me my life today twenty years ago, I suspect I would have focused on all the differences. I would have pointed out everything that hadn’t gone according to plan. What I think now is that I would have been looking at it the wrong way.
Age has changed my relationship with planning. I still believe in goals. I still believe in ambition. I still believe in working deliberately towards the future you want. What I no longer believe is that life rewards those who cling too tightly to a particular script.
Some of the happiest moments of my life arrived through circumstances I never would have chosen in advance. Some of the hardest periods taught me things success never could. Some of the opportunities I value most today only existed because earlier plans didn’t work out the way I expected.
I think that’s one of the reasons hindsight can be so deceptive. Looking backwards, everything appears connected. The difficult periods make sense. The unexpected opportunities seem obvious. The lessons reveal themselves neatly. Living through those moments felt nothing like that. At the time, there was uncertainty, frustration, doubt and often no clear indication of where things were leading.
There were years when I felt behind. Years when I questioned decisions. Years when life seemed to be moving in a direction I hadn’t planned for. Looking back now, many of those periods were quietly preparing me for chapters that hadn’t arrived yet. The experience I gained, the resilience I developed and even some of the disappointments I carried all became useful later in ways I couldn’t have understood at the time.
Perhaps that’s what I’ve come to appreciate most as I’ve gotten older. Life is not nearly as linear as we imagine when we’re young. It rarely follows the neat timeline we create for ourselves. It expands, contracts, surprises, disappoints and occasionally exceeds our expectations in ways we couldn’t have predicted.
As the plane continued across the ocean that day, I found myself thinking less about the life I expected and more about the life that actually unfolded. The businesses, the children, the countries, the relationships, the experiences and the lessons all emerged from a path I never could have planned with any degree of accuracy.
And strangely enough, that thought felt comforting.
For years I believed the goal was to build the life I had imagined. Now I think the real goal was simply to remain open enough to build the life that was waiting for me instead.
Because when I look back at the things that matter most, very few of them came from a plan.
They came from what happened after the plan changed.