I want to tell you a story about starting before you feel ready. Actually, let me back up: I’ve never once in my life truly felt “ready” for the big things. Not when I went to law school, not when I started my career, and definitely not when I launched my own law firm.

At the time, I’d been a licensed attorney for about seven months. Seven. I was still green, still figuring out what I was doing, and I had four kids at home. The idea of asking people to trust me with something as important as their family’s estate planning? It made me feel like an imposter. Like I had no business charging “real” money for “real” services when I was still figuring it out myself.

And yet—that’s exactly what I did.

The Story of My First Clients

Before law school, I had asked everyone I could find: “What kind of law should I practice if I want to have a family life—the kind where I can go to a dance recital at 3 PM on a Wednesday?”
The answer I kept getting was the same: estate planning or tax law.

That set me on the path. I fell in love with estate planning in theory, but law school itself was a miserable experience for me. So when I heard about being a trust officer—a job that let me do estate-planning-type work without being a lawyer—I jumped in. I liked the work, I liked the people, but deep down, I knew something was missing.

I wanted to do estate planning my way. In a way that felt authentic, where I could bring my whole self to the table.

So, I started looking around. Because I was Googling “how to start an estate planning practice,” I began getting targeted ads for companies selling training programs. One particular company kept showing up. Honestly, at first, it felt like a scam. But I kept digging, and eventually I thought: maybe this is the door I’ve been waiting for.

The course cost $7,000. I negotiated it down to $5,400—because remember, baby lawyer, four kids, very little extra cash. Still, it felt insane to spend that much money. But the course came with a promise: get two estate planning clients, and if you didn’t earn the money back, you could request a refund.

That was my entry point.

I dove in. Watched the videos. Did the work. But even as I did, I still didn’t feel ready. I still didn’t feel like I could bring the authority I needed to ask for high fees. I knew the material better than most people, I knew I could deliver value, but I didn’t feel worthy of charging for it.

Finally, I started talking to people in my network. Tentatively, awkwardly, nervously. And then—I landed a client. Then another.

Here’s the surprising part: the clients didn’t blink at my fees. They immediately saw the value. They even felt like they were getting a deal compared to what they would have paid elsewhere.

That moment was like the floodgates opening. I realized the problem wasn’t that I wasn’t ready—it was that I was waiting for a feeling of readiness that was never going to come.

Within a year, I left my job. By January, I was fully self-employed. And for the first time in a long time, I felt fulfilled.

The Myth of “Being Ready”

So why do we think we need to be ready before we start?

Honestly, I think it’s school. From kindergarten on, we’re taught that if we study hard enough, we’ll be prepared for the test. And if we’re prepared for the test, we’ll succeed. That’s the formula.

But real life doesn’t work that way. Real life is messy and unpredictable. No matter how much you prepare, things won’t always go according to plan. Sometimes they turn out worse than you hoped, but often they turn out better than you feared.

Here’s the truth: no amount of preparation will ever make you feel ready. That feeling you’re waiting for—the sense of total confidence, control, and certainty? It doesn’t exist. And waiting for it just keeps you stuck at the starting line.

Three Small Entry Points to Shrink the Starting Line

So if you’re staring at something you want to do but don’t feel ready for, how do you actually get started?

Here are three small entry points that helped me—and that might help you.

1. Shift the story you’re telling yourself.

We’re already telling ourselves stories about what might happen. Usually the worst-case scenario: “If I mess this up, I’ll look stupid. If I charge too much, no one will hire me. If I’m not perfect, I’ll fail.”

But if you’re going to imagine a story, why not also imagine the best-case scenario? “What if this works? What if I land the client? What if this opens a door I didn’t even know existed?”

2. Release perfection.

A mentor once told me: “Beta now, better later.”
That stuck with me. It means: get something down, even if it’s only 80% right. Once you’ve started, you can refine. You can fix. You can grow. But you can’t refine something that doesn’t exist.

3. Find authenticity in your why.

Sometimes the only reason you’re doing something is because your boss told you to. That’s fine. But dig deeper: Why does it matter?

Maybe it matters because your boss’s approval affects your bonus, and your bonus is how your family buys a house next summer. Suddenly it’s not about pleasing your boss—it’s about building the life you want.

Getting to the truth of why you care helps you push through the resistance.

Readiness vs. Preparedness vs. Clear Enough

Here’s where I’ve landed:

• Readiness (the myth) means knowing everything in advance, anticipating every problem, and having zero uncertainty. No one ever gets there.
• Preparedness means having confidence that, no matter what happens, you’ll figure it out. You may not know what’s coming, but you’ve trained, practiced, or at least built resilience to handle it.
• Clear Enough means you know the direction you want to go. You’re aligned with your values. You can let go of the fake problems that don’t matter and focus on the challenges that do.

Think about it like preparing for an earthquake. You can’t predict which wall will fall. You can’t be “ready” in that sense. But you can be prepared: you can build confidence that, whatever happens, you can handle it.

And when you’re clear enough—when you know what matters and where you want to go—you stop wasting energy on things that don’t align with your values. You stop obsessing about the walls you can’t control and start building toward the life you actually want.

Clear Enough to Begin

The truth is, I never felt ready to start my law firm. I never felt ready to ask clients to trust me. But starting anyway is what opened the doors.

And that’s the lesson: you don’t need to be ready. You just need to be clear enough. Clear enough about what matters, clear enough about where you want to go, and clear enough to take the first step.

Because once you start, the floodgates open. The stories change. And you begin to see that maybe—not being ready was the point all along.