When Your Why Isn't Where You Started

Let me start with a confession: I once (a few months ago) walked away from a comfortable, fulfilling, and entirely respectable job. Great colleagues. Good money. Flexible schedule. Satisfying work. My mother was proud. My dry cleaner was pleased. Even my dog had no complaints.

So why would anyone walk away from that?

My wife also had questions.

The answer has to do with something that sounds noble when printed on a motivational poster, but is much messier in real life: my why.

You’ve likely heard the advice to "start with why." It’s not bad advice. But sometimes your “why” doesn’t wait politely at the beginning of your journey like a punctual Uber driver. Sometimes, it shows up later, wearing hiking boots and whispering, “You’re going the wrong direction.”

And sometimes—this is where it gets complicated—your why changes.

The Myth of the Fixed Why

Simon Sinek famously teaches that your “why” is formed early in life and remains constant. In his model, your purpose is a kind of emotional fossil—unearthed through reflection and storytelling, your childhood self leaving breadcrumbs for your adult career path.

And for many people, that story resonates. But here’s a twist: what if your past doesn’t get the final say?

What if your future does?

That’s the central insight from Benjamin Hardy’s book Be Your Future Self Now. Instead of inviting you to ask “Who have I always been?”, he suggests you ask “Who do I want to become?” and “What kind of world am I building toward?”.

This changes everything.

Instead of mining your past for meaning, you build your purpose like a cathedral. Block by block. Vision by vision. Sometimes with very little scaffolding and quite a lot of imposter syndrome.

When Your Inner Skeptic Fights Back

Here’s something to be aware of if you try this at home: The moment you start thinking about who you could become, a little voice inside your head (maybe channeling your 8th-grade gym teacher) says:

• “Who do you think you are?”
• “You’ve never done anything like that.”
• “You’re too old/young/average/fill-in-the-blank.”

This is the part where most people stop. They wait for proof. For permission. For a mythical state of readiness.

But here’s what leaders do: they choose.

Not because they’re certain. But because the future they see is worth fighting for.

Practice Makes Possible

So how do you actually start becoming your future self? You practice. Just like piano. Or parallel parking.

Psychologists have a tool called the Best Possible Self exercise. You imagine yourself three months, a year from now, living a life that has gone surprisingly well. Then you write about it in the present tense—as if it’s already true. Describe where you work and who you’re with. What do you see around you that’s evidence of your success. What do you smell, hear, or sense? Most of all, how does it feel? Pay particular attention to how it feels to be in that future scene.

This isn’t magical thinking. It’s neuroscience. Studies show that when you mentally and emotionally rehearse a compelling future, your brain starts rewiring itself to make that future feel real—and reachable.

That version of you—the one who is living that envisioned reality—starts influencing the choices you make today. You invest your time and awkward first steps in things that your current self might otherwise avoid. You see opportunities and connections that you would otherwise miss. Your future is not the product of your past, it’s a tool for shaping your present.

Your Why Is a Vision, Not a Vow

So let’s go back to your why.

What if it’s not a statement you memorize but a vision you create?

What if it’s not something that was handed to you at age 17, laminated, and sealed in fate-proof plastic?

What if your why is a living, breathing, evolving thing?

And what if you gave yourself permission to let it change?

When you have a clear sense of personal purpose, something magical happens. You lead differently. People feel your conviction. They’re drawn to your clarity—not because you have all the answers, but because you’re clearly moving toward something that matters.

And that, it turns out, is a practical leadership edge.