Hesitation is Holding You Back. Here’s How to Break Free.

The Hesitation Trap

Your finger hovers over the “Send” button, your pulse just a little too loud in your ears.

You’ve already rewritten the email three times, double-checked for typos, and even imagined every possible way your boss might misinterpret your words.

What if it sounds too aggressive? Too weak? Too… wrong?

So you do what hesitation loves most… you pause. You take a deep breath. And then… you move your mouse away. Maybe later.

Sound familiar? Whether it’s an email, a request for a raise, or stepping up for a leadership role, hesitation has a way of creeping in… convincing us that waiting just a little longer is the safer move. LIES!

Here’s the hard truth we’re desperate to avoid: Hesitation isn’t protecting you. It’s holding you back.

Emotion Highlight: What HESTIATION is Trying to Tell You

Hesitation isn’t the enemy—it’s a messenger. It’s there to make you pause and assess, but not to keep you stuck. The key isn’t to silence hesitation; it’s to decode it.

• Is it a real risk or just a fear of stepping up?
• Is this pause necessary for reflection or an excuse to stay in your comfort zone?

Listen to what hesitation is telling you, but don’t let it decide for you.

Trust yourself. You are enough.

When you take action, you’re more than capable of evaluating, adjusting, and navigating whatever comes next.

Confidence doesn’t come from waiting until you feel ready. It comes from taking the leap, knowing you can course-correct if needed.

So the next time hesitation whispers maybe later, try this instead: What is it really telling me? And what’s one step I can take right now?

Leadership Insight: Stop Creating a Culture of Hesitation

As a leader, hesitation doesn’t just affect you—it trickles down. When leaders hesitate, teams pick up on it. The result? Indecision, stalled projects, and second-guessing.

3 Ways Leaders Accidentally Fuel Hesitation (and How to Fix It):

#1: Micromanaging Decisions: When you second-guess every decision your team makes, they learn to hesitate instead of act.

Do this instead: Empower your team to own their choices. Give them the framework, then trust them to execute.

#2: Unclear Expectations: Vague instructions = hesitant execution.

Do this instead: Be clear on goals, priorities, and desired outcomes. Ambiguity is a hesitation breeding ground.

#3: Punishing (or Avoiding) Mistakes: If your team fears making a wrong move, they’ll default to not moving at all.

Do this instead: Normalize learning moments by sharing your own past mistakes—and what you learned from them. When leaders admit missteps and demonstrate growth, it sets the tone for a team that takes smart risks instead of avoiding action out of fear.

🎯 Leadership Action Step: This week, when you see hesitation slowing your team down, resist the urge to jump in with the answer. Instead, ask: “What do you need to feel confident making this decision?” Then, provide that—whether it’s clarity, reassurance, or permission to move forward.

For example:

• If a team member keeps stalling on a project, ask: “What’s the biggest unknown here? Let’s tackle that first.”
• If someone keeps seeking approval, say: “I trust your judgment. What decision would you make if I weren’t here?”

By shifting from solving for your team to coaching them through hesitation, you build a team that takes action with confidence.

Career Empowerment: Confidence Isn’t Built in the Thinking—It’s Built in the Doing

Hesitation loves to disguise itself as “being responsible.” We tell ourselves:

• I need to think about this more.
• I just need more information.
• Now isn’t the right time.

After putting on our honesty and transparency hat… most of the time we will see that we’re just stalling.

How to Break Free from Hesitation:

➡️ Shrink the Decision Window. If a decision doesn’t involve life-or-death stakes, set a timer.

🟢 Five minutes, five hours, or five days, you choose. What’s important? You give yourself a deadline.

➡️ Act First, Adjust Later. Confidence doesn’t come before action; it comes after action.

🟢 Want to be more confident speaking up? Do it before you feel ready.

🟢 Want to apply for that leadership role? Submit the application, then figure it out.

🟢 Want to build a strong network? Start by reaching out to one person today.

➡️ Take the Smallest Step Forward. If hesitation is keeping you stuck, don’t aim for the big move—just take the next move.

🟢 Instead of applying for the promotion, start with a conversation about growth.

🟢 Instead of a total career pivot, start with exploring new roles in your industry.

🟢 Instead of waiting until you “feel ready”, start by registering for From Uncertain to Unstoppable and take control of your career.

✨ Success Story: One of my WILD Coaching clients spent months talking herself out of going after a role she knew she was qualified for. Every time she thought about applying, the doubts crept in—What if I’m not ready? What if they say no?

Before reaching out to me, she kept waiting for a perfect moment that never came. We worked through her hesitation, and she applied with a new approach: confidence through action. Instead of overthinking, she took the leap… and it paid off! She applied, nailed the interview, and not only landed the job, but secured a higher salary than expected.

🎯 Your Career Action Step: Identify one area where hesitation is holding you back. Make one move forward today. Small action > perfect plan.

Shared Wisdom

"You don’t have to be confident to start. You just have to start to become confident."

Whether you’re leading a team or leading your career, momentum is your best friend. The next time hesitation creeps in, remind yourself: Confidence is a muscle that grows with use.

TL;DR (Too Long; Didn’t Read)

• Hesitation isn’t protecting you—it’s keeping you stuck. Learn to decode it instead of letting it control you.
• Leaders: Stop unintentionally fueling hesitation on your team through micromanaging, unclear expectations, or mistake-avoidance. Instead of jumping in with answers, ask: “What do you need to feel confident making this decision?”
• Career Professionals: Confidence doesn’t come before action. Confidence comes from action. Shrink the decision window, take the smallest step forward, and adjust as needed.
• Golden Nugget: Confidence is built in the doing, not the waiting.