Preparing for Success – Plan or Leap

The journey doesn’t start at the end. It doesn’t start in the middle. And it sure doesn’t start with complete clarity. But it does have to start.

When I finally broke from my old life, it didn’t happen in one clean moment. It took years of unease, a few tears, and a conversation that felt more like a breakup than a business decision. Fifteen years with a mentor, partner, and friend. And then, the slow unwinding.

I wanted it to be graceful. It wasn’t.

The next twelve months were full of false starts. I said yes to too many things. Tried to keep too many doors open. Told myself I was being smart, hedging my bets. Really, I was just scared to commit.

I kept waiting for clarity to show up before I acted. It never did.

Eventually, I reached a point of no return. Not a moment of certainty, but a moment of exhaustion. I couldn’t keep dabbling. I had to pick a path and start walking, even if I didn’t know exactly where it led. Looking back, that was the real beginning.

You don’t prepare for success by waiting until everything is lined up. You prepare by moving, by testing, by getting your hands dirty and your ego bruised. You prepare by seeing what breaks, what holds, what matters.

And if I’m honest, the cool version of me likes to say I leapt into the unknown with courage. The real version cut costs, increased passive income, called mentors and friends, and did every small thing I could to soften the fall. It wasn’t glamorous. It was survival mixed with faith.

If I could go back, I’d tell that version of me a few things.

First, preparation is not about building a perfect plan. It’s about anticipating the weak spots. The boredom. The doubt. The fatigue. You don’t need to know the whole route up the mountain, but you do need to expect that your legs will burn.

Second, a guide helps. I didn’t have one back then. I wish I did. A coach, a book, a community. Something like The Quiet Burden of Midlife Millionaires would’ve been nice. But maybe it had to be hard-fought. Maybe I had to bleed a little to understand what others would someday need.

Third, openness matters more than certainty. You don’t have to know your purpose. You just have to be willing to look for it.

People love to throw around the words vision, mission, purpose, values, principles, creed, framework. I’ve been in rooms where entire teams argued over which one came first. Which one mattered most. Whether we even needed all of them.

The truth is, we need language, but we don’t need it perfect. We just need to start using it together. To agree on what it means to us, not what a consultant says it should mean. Because if you can’t agree on what words mean, you’ll never agree on what work matters.

For me, the word that mattered most turned out to be values.

Not at the beginning. Back then, I couldn’t have told you what my core values were. I just knew something about the life I’d built wasn’t mine anymore. Three years later, after carving and shedding and rebuilding, I found them. They’d been there all along. I just hadn’t named them.

That’s the irony of preparation. You think it’s about getting everything ready before you begin. But it’s actually the process of discovering who you are while you’re already in motion.

You prepare for success by being in the game. By climbing. By paying attention.

So if you’re standing where I was—ready but uncertain, strong but restless—don’t wait for the perfect starting point. You’ll never find it.

Ask yourself a simpler question: where can I start?

Is it with values? With purpose? With a clearer mission? With redefining success?

It doesn’t matter which you choose. It only matters that you do.

The journey doesn’t reward those who plan the most. It rewards those who keep showing up, who start naïve, who learn as they go, and who are humble enough to change their map when the terrain shifts.

Start walking. Pack light. Pay attention.

You’ll prepare for success by climbing toward it.

And next week, we’ll start unpacking the compass that guides that climb—your values. The ones that have been quietly waiting for you to notice them all along.