The Courage to Be Uncomfortable: A Leadership Lesson Every Woman Needs

Because growth doesn’t happen in the safe zone.

When was the last time you held your tongue, dimmed your light, or avoided a tough conversation just to keep the peace?

Most of us have done it. And while the instinct to “not ruffle feathers” can feel like professionalism, politeness, or even survival—it can also be the very thing holding us back from our biggest growth.

Brandi Starr learned that lesson early in her career. And it changed everything.

Now the COO of Tegrita, co-author of the best-selling CMO to CRO, host of the Revenue Rehab podcast, and a Strategic Advisor for Wednesday Women, Brandi shows up boldly, speaks her mind, and brings her whole self to the table. But she wasn’t always that way.

The turning point? An office move.

One small office. One big mindset shift.

On her first day at a new job, Brandi was shown to a cubicle—just like everyone else with her title. But a few days later, her boss returned from vacation and immediately asked, “Why are you out here? I requested an office for you.”

She hadn’t known that was even an option. She hadn’t thought to question it. And when it became clear she was getting moved to an office—one nestled between two directors—Brandi felt the tension rise. There were whispers. Side-eyes. People wondering why she got something others didn’t.

She considered giving it up. Just going back to the cube and avoiding the drama.

But her boss pulled her aside, shut the door, and shared a perspective intended to help set Brandi up for success. To use a tricky office culture situation as a way to establish her approach as a leader.

One little phrase would reshape the way she worked—and led—for the rest of her career:

“Don’t be afraid to ruffle feathers.”

The advice that reshaped a career—and a leadership style.

That moment gave Brandi permission to stand tall in her skills, speak up with conviction, and push for what she knew was right—even if it made people uncomfortable.

It wasn’t about ego. It was about advocacy. For the work. For the mission. For herself.

And now, in her executive role, she carries that same lesson forward—not just in how she leads clients and strategies, but in how she supports her team.

“If my people deserve an office,” she says, “I’m going to be the one pushing for that office.”

Leadership isn’t about keeping everyone happy. It’s about leading with integrity—even when it’s not the popular move.

Ruffling feathers with empathy.

Of course, Brandi’s not suggesting we bulldoze our way through disagreements or throw out kindness in the name of confidence. She’s a communicator to her core—which means she balances courage with empathy.

Her strategies for speaking up are refreshingly practical:

• Ask powerful questions that guide people toward new ideas.

• Name the discomfort: “What I’m about to say might ruffle feathers… and hear me out.”

• Always check in with your why—if it’s coming from ego, step back. If it’s coming from clarity and self-advocacy… go forward.

This kind of grounded, values-led assertiveness is a superpower. And it’s something any woman can practice—whether you’re leading a team, managing clients, or simply trying to show up more fully in your own life.

So… what feathers are you afraid to ruffle?

Maybe you’ve been holding back on an idea you know would work. Maybe you’ve stayed quiet in a meeting—or in a relationship—when you really wanted to speak up. Maybe you’re tired of trying to make it all “fair” and palatable and easy for everyone else.

Brandi’s story is a reminder: you don’t have to be loud to be powerful, but you do have to be brave.

Let go of the need to please. Let go of the fear of friction. Growth—and leadership—live on the other side of discomfort.

🎧 Hear the full story on the Wednesday Women podcast: The Ripple

💡 Want more Brandi in your life? Follow her on LinkedIn for real talk on marketing, leadership, and making magic without the “random acts.” And check out her podcast, Revenue Rehab, for bold conversations about driving meaningful growth.

💜 Want to meet Brandi and other women like her?  Consider becoming a Member of Wednesday Women.