Why You’ll Never Feel Ready—and That’s Okay

How many times have you whispered to yourself, “Not yet… I’m not ready”? For love. For change. For calling. And how many opportunities have slipped past while you were still preparing?

There’s a strange comfort in postponement. You wait telling yourself that with a little more work, more knowledge, more healing you’ll finally be ready.

But what if all that waiting isn’t caution but fear disguised as responsibility?  At a certain point honest preparation turns into serious avoidance.

Jewish wisdom speaks directly to this. At Sinai, when the Jewish people were offered the Torah, they responded in one voice, “We will do, and then we will understand.” They knew that the first thing they needed to change was action. Only then do you get a shot at success.

Growth doesn’t come from waiting until you’re confident. It’s the result of moving before you’re one hundred percent sure.

Psychology calls this delay tactic cognitive avoidance. You have a perfectly reasonable goal but you only stay in your head—preparing. Why? Because you’re afraid of discomfort.  Moving forward demands change, and this brings a whole bucket of stress landing you in Catch-22.  Act and feel uneasy, stand still and feel ashamed. Not great choices, so you strike a bargain to get out of feeling either by at least feeling productive with all that getting ready.

The only way out of this mirage of a solution is through a process called behavioral activation. This is strategically doing what you’ve been avoiding, not when it feels easy. Paradoxically, confidence doesn’t come before you act; it comes after.

The Sage Hillel expressed it this way: “If not now, when?” (Ethics of the Fathers, 1:14). If you’re waiting for the perfect version of yourself to show up, you’ll be waiting forever.

Failure Isn’t the Obstacle – It’s the Path

What’s the source of this avoidance?

The same voice that says you’re not ready would answer its laziness, but that’s not true. Most people aren’t lazy—they’re scared. So in the guise of being responsible, you reset, again. Another book. Another podcast. Another plan. But still, no action. This buys you time but the fear of not measuring up always comes back.

Jewish tradition treats this is human flaw with compassion, “No one truly understands until they’ve stumbled.” (Talmud, Gittin 43a). God doesn’t ask for perfection. He asks for presence. For showing up. For trying again. That’s the Torah’s method of growth: stumble, rise, refine.

Getting practical, how do you get out of this trap?

1. Make a move.

Not a 10-year plan, just three small but actionable steps.  They can’t be the same flavor, though.  Reading three books still only counts as one and even that’s overkill. Having a rough plan keeps the forward momentum going while not being too overwhelming.

2. Change the way you look at failure.

Any worthwhile goal is going to be in the distance and everyone who sets out on a journey is going to stumble.  If you’re thinking about going back to school, submit several applications because a fair amount of them are going to turn you down.  If you want to build a relationship, stop waiting to feel “ready.” Go on real dates. Let it be awkward.  But get a move on because you’re going to pick up a few dud rocks before you find your gem.

If you’re stuck in your job, send out 100 résumés.  Statistically, without exaggeration, 98% of employers are going to turn you down flat.  That’s just the way it is.

The reframe here is failure isn’t something that gets in the way. It’s the path itself. You’ll get better because you begin and fail, not before.

Every honest step builds the person you hope to become. Jewish history wasn’t built by perfect people. Moses stuttered. David sinned. Jonah ran. But they showed up, took action, failed, and only then saw the right move. Your path is no different.

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