We’re All Winging It

A few weeks ago, during a lunch with my parents, my dad mentioned that he was twenty-eight years old when he and my mom moved from Portugal to South Africa with barely any luggage, carrying a wide-eyed three-year old. I froze, my fork poised in front of my open mouth.

I’d heard this story many times, but it was the first time I truly considered their age, and the people they must have been in that moment. I thought back to the people I had imagined them to be when I was very young: certain, steady, all-knowing. The kind of adults who had mastered life and knew exactly what they were doing, had an answer to every question.

I couldn’t help contrasting their experience with who I had been at twenty-eight. I had a well-paid, senior role, influencing the people strategy for a multinational organisation. On the outside, I looked like I had it all together. I didn't. I hadn't the faintest clue what I was doing. I was just winging it, letting life pull me along.

I lowered my fork, my meal suddenly forgotten. That contrast stirred something deeper in me. The image of my parents as having “had it all figured out“ in their twenties dissolved. They weren’t flawless adults standing on solid ground their whole life. They had experienced hardship and poverty. They were young parents in a foreign country with no plan and no prospects, just a future filled with hopes and dreams. Neither they nor I, despite our very different circumstances, knew what we were doing.

For most of my life, even into my early thirties, I felt shame around not knowing things, and I often felt like a failure for not being "smart enough", despite my academic achievements. So, I pretended I knew everything. I thought confidence came from pretending I had no blind spots, that I had it all figured out, that I knew everything I needed to know. Spoiler alert: I didn’t.

Looking back, I realise part of the pressure I felt to “know everything” came from childhood. My parents didn’t grow up with education or opportunity, so confidence became their armour. They carried themselves with a kind of certainty that held our lives together, and as a child I mistook that survival instinct for absolute truth. I learned early on that adults are supposed to have answers, not questions. And for a long time, I carried that belief too.

In that moment, I understood: none of us truly know what we are doing. We are all winging it. Sure, some of us have more clarity in the direction we want our lives to take than others, but at the end of the day, we're all just figuring life out as we go along, within the circumstances we find ourselves.

There is a kind of comfort that comes from realising just how much will forever remain a mystery to us. The older I get, the more humbling and liberating it becomes to acknowledge the vastness of everything I don’t know. Not having it all figured out no longer makes me feel small. It makes the world infinitely larger. And, as I learned, questioned, and unlearned, curiosity stopped being a threat to my identity and became the engine of my growth. Every book, every conversation, every moment of stillness added another small piece to the vast puzzle of living.

Everyone I speak to, no matter at what age or phase of life, is in some way winging it. And this is OK. Very few of us are born knowing exactly what we will do with our life, and no one is able to see exactly how our lives will unfold. We figure it out as we go along, and we will keep doing so until the end of our days. Adulthood is more about navigation than mastery, wisdom is more about noticing than knowing. There is no finish line where certainty greets us with applause.

If this is true, then maybe the goal was never to “figure it out” at all. Maybe the point is to stay curious, whether we're in our twenties or eighties. To keep asking, listening, learning. To let the mystery of life fascinate us rather than scare us.

So, dear reader, if you ever feel behind, lost, or unsure, no matter your age, remember: you’re not supposed to have it all figured out.

After all, none of us do.

Until next week,

Ric