There’s a question we rarely ask out loud, though it quietly follows us through every chapter of our lives: If given the chance, would I live this life again – or would I want something entirely different?
It’s not the kind of question that arises on a Monday morning while checking emails or during small talk over coffee. It comes uninvited – often when the world slows down or someone else’s story brings us face-to-face with our own. For me, it re-surfaced while watching a documentary on the Oklahoma City bombing. A survivor, recounting a day that altered the course of so many lives, shared that in that moment she asked that question of herself. And in that quiet moment, I realized: That’s the very question I’ve repeatdely asked myself – and answered – in order to stand where I stand today.
Most people don’t ask it consciously. And many who do, ask it only in retrospect, with regret as the backdrop. But for those who dare to ask it while still in motion, it becomes a compass – less about the life we’ve already lived and more about the life we’re still building.
That question doesn’t look for a dramatic yes or no. It asks for alignment. It asks whether the life we’re living reflects the person we’ve fought to become. It asks if the choices we’ve made, and continue to make, come from truth or from habit, from desire or from fear. And more often than not, it asks if we’ve been living for ourselves, or simply borrowing from the scripts handed to us by others.
When I look at my own life – professionally, personally, emotionally, spiritually – I don’t see perfection. I see decisions that cost me, but gave me clarity. I see pivots that made little sense at the time but were crucial in hindsight. I see leadership not just in roles or responsibilities, but in the quiet act of choosing differently when comfort begged me not to. The life I live today wasn’t shaped by default. It was shaped by discomfort. By asking hard questions early, when the answers still had time to matter.
And while my answers shaped my path, I’ve also come to realize something deeper: asking the question is itself an act of leadership. Not just self-leadership, but a form of silent mentorship. When people sense that you are living a life chosen – not inherited or imposed – they feel something shift. You don’t need to tell them to reflect. Your presence does it for you.
We live in a time where the lines between curated success and authentic fulfillment are increasingly blurred. Social media sells lifestyles; institutions reward conformity; hustle culture teaches people to optimize everything except their own happiness. In that context, pausing to ask yourself “Would I live this life again?” is not just reflective. It’s radical.
The philosopher Søren Kierkegaard once wrote, “Life can only be understood backwards, but it must be lived forwards.” Most people stop at the first half – waiting until the end of something to make sense of it. But the real work lies in choosing while you’re still inside the story. Because what matters isn’t whether you have all the answers – it’s whether you have the courage to keep asking the right questions.
I often think about students I teach, peers I mentor, leaders I coach – so many of them caught in lives that look good from the outside but feel hollow on the inside. They don’t lack intelligence or ambition. What they often lack is permission. Permission to pause. To reflect. To revise. We were taught how to plan, not how to realign. How to achieve, not how to ask if what we’re achieving still matters.
So, what do you do with this question once it arrives?
You don’t need to throw your life into chaos. You don’t need to start over. You simply need to begin – again. With one choice. One conversation. One boundary. One “yes” that used to be a “no,” or a “no” that should’ve been said a long time ago. The goal isn’t to live a perfect life. It’s to live one that, if asked again tomorrow – Would you live this life again? – you could say, “Yes. Not because it was easy, but because it was mine.”
This question is a gift. A mirror. A moment of truth.
And if it’s come to you now, don’t turn away. Stay with it. Let it do its work. Because whether your answer is a gentle affirmation or a painful awakening, it will offer something rare in this world – clarity.
And with clarity, we stop drifting. We start choosing.
We begin again – this time, deliberately.