Stuck? Time to Get Uncomfortable


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NEWSLETTER #54

Hey there!

Let’s talk about something that might make you squirm a little: deliberate discomfort.

You know that cosy feeling of knowing exactly what you’re doing, where everything feels predictable and safe?

That’s your comfort zone.

And while it feels great, it might just be the thing holding you back from your next big career leap.

I always say, “Don’t let your comfort be your cage". It’s a trap many of us fall into without even realising it.

Think about it.

When was the last time you did something at work that made your palms sweat a little? That made you think, “Am I really qualified for this?”

If it’s been a while, we need to talk.

Here’s the thing: growth happens when we stretch ourselves, when we step into spaces that feel a bit too big for us.

It’s like trying to build muscle by lifting the same light weights every day. Sure, it’s comfortable, but you’re not getting any stronger.

Let’s look at some typical situations where you might need to step out of your comfort zone:

Discomfort Zones in Leadership

Public Speaking: You’ve mastered small team meetings, but now you’re asked to present at a company-wide event. Terrifying, right?

Giving Tough Feedback: It’s easy to praise, but calling out poor performance? That’s a whole different ball game.

Making High-Stakes Decisions: When the buck stops with you, and you’re faced with a decision that could make or break a project.

Leading Through a Crisis: When everything’s going sideways, and all eyes are on you for direction.

Advocating for Yourself: Whether it’s asking for a raise or pitching yourself for a promotion.

These situations can make even seasoned leaders feel like they’re back in high school, palms sweaty, heart racing.

But here’s where the magic happens.

Strategies for Embracing Strategic Discomfort

1. Start Small
Don’t dive into the deep end right away. If public speaking terrifies you, start by speaking up more in meetings, then gradually work your way up to larger audiences.

2. Reframe Your Thinking
Instead of “I’m not ready for this", try This is my opportunity to grow”. It’s not about being perfectly prepared. It’s about being willing to learn.

3. Seek Feedback
After stepping out of your comfort zone, ask for feedback. It’s not about validation, but about learning and improving for next time.

4. Celebrate the Attempt
Don’t just focus on the outcome. Celebrate the fact that you took the leap. Each time you do, it gets a little easier.

5. Find Your Support System
Share your goals with trusted colleagues or a mentor. They can provide encouragement and accountability.

6. Reflect and Learn
After each ‘uncomfortable’ experience, take time to reflect. What went well? What would you do differently next time?

Common Mistakes to Avoid

Waiting to Feel “Ready” Newsflash 📸: You’ll never feel 100% ready. Don’t let perfect be the enemy of growth.

🚩 Overcompensating When we’re uncomfortable, we might try too hard to prove ourselves. This can come off as inauthentic or overly aggressive.

🚩 Avoiding Feedback It’s tempting to avoid asking how we did when we’re feeling vulnerable. Don’t. Feedback is gold for growth.

🚩 One and Done Stepping out of your comfort zone once isn’t enough. It needs to be a consistent practice.

📚 Here’s a personal story:
While I thrived in the performing arts for much of my life, networking was my kryptonite.

As an introvert (yes, really!), networking events felt like a special kind of torture - superficial interactions, transactional exchanges, and energy-draining small talk.

My go-to responses to invitations were “We’ll see” or “Maybe” - code for “Not a chance!”

Then came my “year of yes” and a career coach who challenged me to face this fear head-on. Her assignment? Say yes to every networking invitation and put it in my calendar immediately. No excuses.

Those first few events were rough. I was the quintessential wallflower, awkward and observing from the sidelines.

But slowly, something shifted.

The stress began to ebb, conversations became easier, and - shockingly - I started to enjoy connecting with people.

The real surprise?

Some of those random connections have led to some of my best personal and business relationships, propelling my career forward faster than I’d ever imagined.

Stepping out of my comfort zone didn’t just change how I approached networking - it transformed my entire career trajectory.

It wasn’t easy, but it was worth every uncomfortable moment.

🎯 Your Comfort Zone Challenge

This week, I want you to do one thing that makes you professionally uncomfortable.

Maybe it’s speaking up in that big meeting, or having that tough conversation you’ve been putting off.

Whatever it is, do it.

Then, I want you to reflect on three things:

  1. How did it feel before, during, and after?
  2. What did you learn about yourself?
  3. How can you build on this experience?

Closing Thoughts

Remember, discomfort is not the enemy. It’s the price of admission for growth.

Every time you step out of your comfort zone, you’re expanding it. You’re becoming a more capable, more confident leader.

So, are you ready to get a little uncomfortable?

Let's leap,

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Leadership Leap

I help leaders navigate the messy, real parts of leadership that most advice skips over. Through personal stories, contrarian insights, and frameworks that actually work, I share what I've learned from 20+ years of leading teams and coaching executives. Every Wednesday, expect honest insights in 5 minutes or less - no fluff, just the stuff that moves the needle.

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