Career Winners Circle

06/03/2025

I think we’ve been reinforcing the wrong things.

In the spirit of reflection this week, I came across an interesting article about WWII that really got me thinking.

Back then, the military studied bullet holes on returning fighter planes to decide where they should add more armor.

The wings, tail, and fuselage were riddled with damage, so they assumed those were the weak spots that needed reinforcement.

But statistician Abraham Wald pointed out a critical flaw in that thinking:

💡 Those were the planes that survived.
The real vulnerabilities were in the areas with little to no damage, like the engine and cockpit, because planes that were hit there didn’t make it back.

This concept is known as survivorship bias, and it’s still quietly shaping the way we lead today.

We focus on what’s visible:

The high performers. The loud contributors. The “planes that returned.”

But what about the talent we don’t see? The quiet overachievers. The unspoken struggles. The teams stuck in outdated systems with no clear path to grow.

If we only reinforce what’s already survived, we miss the blind spots that are quietly costing us innovation, retention, and momentum.

If we want to build resilient, future-ready organizations, we have to start looking beyond what’s right in front of us.

Let’s stop managing for yesterday’s performance—and start building for tomorrow’s potential.

What are you reinforcing?

05/26/2025

Thinking of those who gave everything in service to our country. Their sacrifice reminds us of the values we hold dear: courage, commitment, and unity.

Wishing you a meaningful Memorial Day as we reflect, remember, and honor.

04/24/2025

Some connections just click.

I had a blast collaborating with the brilliant —Revenue & Performance Consultant, TEDx speaker, podcast host, bestselling author, and founder of Business Builder Throw Down (yes, all the things!).

What started as great conversation turned into a meaningful connection… so much so that Holly packed her bags and came to visit me here in Mexico City!

We talked business, impact, and what happens when purpose meets performance, and of course, snuck in some tacos and laughs too.

Grateful for powerhouse women who walk the talk and make collaboration feel like magic.

Here’s to more good conversations.

04/22/2025

Who knew helping leaders get out of the soul-crushing grind would put me on one of the most iconic billboards in New York City?

Seeing Escaping the Career Trap glowing like a disco ball in Times Square is wild—in the best possible way. But more than a personal milestone, it’s a powerful reminder that the message matters.

What started as a rallying cry for ambitious professionals stuck in “meh” mode has become a full-blown movement.

This book was born from years of coaching high-performers who checked every box except the one that said “fulfilled.” It’s for the driven folks who know they’re meant for more, but can’t quite see the next step, or how to build a career that feels worth waking up for.

Even if you never read the book, here are three ways to avoid the mid-career funk:

1. Treat your career like a business - you are the CEO of You Inc.

2. Play to your strengths - mitigate against your weaknesses and continue to develop your areas of excellence.

3. Avoid letting fear slow you down by embracing an experimental mindset. Take small steps, leverage the wins, and rework the things that didn't go as planned.

We’re done tolerating apathy. It’s time to turn the corner.

Come join me at the corner of Ambition Ave and Get-It-Done Blvd.

03/28/2025

Why do people resist change? It’s not fear—it’s comfort. The status quo feels safe, while the unknown feels risky.

But in today’s fast-moving world, staying comfortable is the most significant risk of all. Leaders, and Organizations that thrive are the ones that help their teams embrace change, not by forcing it—but by making it feel less like a threat and more like an opportunity.

Simon Sinek breaks this down brilliantly in his video The Truth About Change. It's worth a watch!

https://youtu.be/vR1af-Q7Z7U?feature=shared

How do you help your team or organization navigate change?

To affect change inside an organization we must remember why people resist change. People don't fear change, people like comfort. The status quo is more comf...

03/25/2025

There was a time when I viewed my career as something happening to me. I was on autopilot, checking off tasks, waiting for the next big break to land in my lap.

I figured success would show up if I kept doing what I was doing.

Spoiler alert: it didn’t.

But then, something clicked. I realized I needed to take charge of my career.

Waiting around for opportunities was no longer an option. I began to create my path, set my goals, and challenge myself to grow.

I embraced change instead of running from it. I stopped the negative slide of complaining about shifts in the market or workplace and instead began to see them as chances to adapt and level up.

I learned that taking risks wasn’t about being reckless; but about making well-informed decisions that could lead to more opportunities.

Most importantly, I came to understand that learning never stops. The more I invested in enhancing my existing skills and acquiring new ones, the more I grew as a person and a leader.

Don’t wait for success to find you. Take ownership of your journey, keep evolving, and always be ready to seize the next opportunity that comes your way.

03/21/2025

Success Isn’t About Doing More—It’s About Doing It Differently.

If working harder was the key to success, burnout wouldn’t be at an all-time high. Yet, many leaders and organizations still believe that pushing for more—more meetings, more hours, more output—is the answer. Spoiler alert: It’s not.

The best leaders don’t demand more effort; they unlock more potential. They remove friction, ignite ambition, and create an environment where employees thrive.

Swipe through this carousel to see what drives success—and how you can lead smarter, not harder.

Drop a line in the comments if you’re ready to rethink how work really works.

03/18/2025

The Biggest Hurdles Women Face in Leadership—And How We Fix Them

Women stepping into leadership roles still face challenges that have nothing to do with skill—and everything to do with outdated workplace structures. Yes, we’ve made progress, but let’s not pretend the playing field is level.

Here’s where the biggest barriers still show up:

🔘 The Proving Ground Never Ends
Women are expected to demonstrate their value at every stage, while men are often promoted based on potential. The result? A never-ending cycle of proving (and re-proving) competence before advancing. Companies that measure talent by impact—not optics—will be the ones that keep top performers.

🔘 The Leadership Tightrope
Assertive men? Strong leaders. Assertive women? “Too much.” Collaborative men? Team players. Collaborative women? “Lacking authority.” The double standard forces women to adapt their leadership style to be palatable instead of powerful.

🔘 Speaking Up (and Actually Being Heard)
Having a seat at the table isn’t enough—it’s about making sure voices aren’t ignored. Too often, women’s contributions get overlooked, repeated by others, or dismissed. Companies that prioritize intentional inclusion in decision-making, not just meetings, will build stronger leadership teams.

🔘 The Unspoken Gatekeeping
Leadership opportunities aren’t just about performance—they’re about relationships. If the real power circles exclude women (informal meetups, golf outings, backchannel conversations), access to leadership stays limited. Mentorship is helpful, but true sponsorship is what opens doors.

🔘 The Pay & Power Gap
Women still hold fewer executive positions and earn less—not because they’re less capable, but because the system wasn’t built for them. Companies that fail to prioritize equity in pay, promotions, and leadership pipelines will struggle to retain top talent.

🔘 The Bottom Line
Women don’t need to change—workplaces do. Leadership isn’t one-size-fits-all, and the companies that embrace diverse leadership styles will be the ones that thrive.

👇 What shifts have you seen lately that are making a real difference for women in leadership? Drop them in the comments!

03/17/2025

What a great conversation with Ken Eslick on The Leaders Lab podcast, we talked about navigating the scary stuff in your career, understanding yourself on a deeper level, and embracing an experimental mindset to "fail successfully." We dive into key mindset shifts and strategies that fuel career growth, helping you turn challenges into stepping stones for success. If you're ready to rethink setbacks and take bold steps forward, this episode is for you!

03/11/2025

Trust and Instinct Are the Missing Variables in the Leadership Equation

Have you ever been so sure of something, only to realize—too late—that all the signs were telling you otherwise?

While visiting Budapest, my partner and I grabbed groceries, returned to our Airbnb, punched in the building’s keypad code, and nothing happened.
We tried again. And again. Still no luck.

A resident walked up, entered their code, and the door opened like magic. We slipped in behind them.

Up one flight of stairs, then another. None of the doors looked familiar. That’s when it hit—we were in the wrong building.

We had tailgated a stranger into a nearly identical building with one key similarity: a keypad entry. Once I took a step back, I noticed everything was off. All the small details were telling me we were in the wrong place. I just hadn't paid attention.

The leadership lesson I unlocked.

How often do we charge ahead simply because things feel familiar?

Routines become ingrained, we stop questioning them. We default to the same processes and assume we’re on the right track—until we hit a locked door.

The challenge is knowing when to trust your instincts and when to pause and reevaluate. Here are three warning signs that you may be in the wrong building and what to do about them:

🚫 Your spidey senses are tingling.
You can’t quantify it, but something feels off. Instead of ignoring it, slow down, observe, and challenge your assumptions.

🚫 Things feel harder than they should.
If you’re constantly pushing a boulder uphill, stop. While some friction is normal, it’s time to reassess, if the right moves still aren’t opening doors.

🚫 You assume you're right.
I didn’t question our location until I’d already gone to the wrong floor. Surround yourself with people who will challenge your thinking and point out when you’re off course.

Are you where you think you are? Or have you been heading up the wrong staircase all along?

The sooner you notice, the easier it is to adjust—before you need a major course correction.

✅ Stay self-aware. ✅ Check your instincts. ✅ Take action early.

03/07/2025

Your Employees Checked Out a Long Time Ago—Did You Notice?

The biggest threat to your business isn’t a market crash or budget cuts. It’s employees who stopped caring.

And here’s the harsh reality: Most leaders don’t notice until it’s too late.

Disengagement isn’t just about low morale—it’s a silent productivity killer that’s bleeding your business dry:

❌ Goals missed. Deadlines pushed. Results stalled.
❌ Innovation opportunities are wasted because no one speaks up.
❌ Your best talent walking out the door (or worse—staying, but doing the bare minimum).

So, ask yourself: Are your employees showing up, or just clocking in?

Because here’s the truth: You can’t demand engagement. You have to create it.

✔️ Give them a reason to care beyond a paycheck.
✔️ Stop micromanaging—let them own outcomes.
✔️ Make growth and impact a non-negotiable part of your culture.

If your team is coasting, the problem isn’t them—it’s the system they’re stuck in.

What’s ONE thing that ever made you feel truly engaged at work? Drop it in the comments—let’s break the cycle.

03/04/2025

When Life Hands You Lemons… You Make a Desk Out of a High Chair 🍋

One of the biggest reasons I launched my business in 2018 was to have the flexibility to work anywhere in the world. Since then, I’ve taken client calls from San Pedro, Belize, built AI-powered growth strategies in Mexico City, and led high-impact leadership sessions from Cardiff, Wales. No matter where I am, the mission stays the same: helping leaders break through growth ceilings and scale their businesses with confidence.

So when I landed in Prague after an amazing weekend in Rome—ready to dive into work—the last thing I expected was an Airbnb curveball.

At 10 PM, I got the dreaded message: our place was no longer available due to an emergency. Luckily, they had another unit in the same building. Crisis averted… or so I thought.

The next morning, I realized: No desk. No table. Just me, my laptop, and a child’s high chair.

So what did I do? I made it work.

That tiny plastic throne became my command center for the day—back-to-back client calls, business development discussions, and even securing new partnerships. Not exactly ergonomic, but definitely effective.

If I’ve learned anything from working remotely, it’s that success isn’t about perfect conditions—it’s about prepared conditions.

💡 My top three remote work tips for staying productive no matter what:

✔️ Tech setup and connectivity: Always check your Wi-Fi and have a backup plan. Portable hotspots and VPNs are lifesavers.

✔️ Time blocks for time zones: Be proactive about scheduling so you’re operating at peak productivity (without 2 AM meetings).

✔️ Set up a focused workspace: Whether you’re at home or on the go, carve out a quiet, distraction-free area where you can truly focus. Your environment shapes your effectiveness.

Because in business (and in life), waiting for the perfect setup is just another way to stay stuck.

🚀 Now it’s your turn—What’s your best remote work tip? Drop it in the comments! 👇