When Success Looks Good, But Feels Off | Navigating the Quiet Pull Toward More with Whitney Faires
There’s a specific kind of tension that shows up when your life looks successful on paper, but something inside you feels unsettled. You’ve done everything “right.” You’ve climbed, delivered, led, and carried the weight. And yet… it still feels off.
That’s exactly where today’s conversation begins.
In this episode, I sit down with Whitney Faires, an internationally recognized leadership advisor, executive coach, and former corporate leader who built and led a $2.5B business function. But this conversation isn’t about résumés or titles. It’s about the quiet pull toward more, the internal reckoning that so many high-achieving women experience, and how to navigate success without burning out or abandoning yourself in the process.
If you’ve ever thought, “Is this it?”—not from a place of ingratitude, but awareness—this episode is for you.
Why Success Can Feel Misaligned (Even When You’ve “Made It”)
Many senior leaders and high performers reach a point where the external rewards no longer match their internal experience.
When Achievement Stops Feeling Fulfulling
Whitney and I talk about how success can become disorienting when the goalposts keep moving. Promotions, awards, and recognition can feel validating in the moment—but fleeting soon after. That “this is it?” feeling is often a signal, not a failure.
The Difference Between Gratitude and Suppression
One of the most powerful themes in this episode is learning to hold gratitude and desire at the same time. Wanting more doesn’t mean you’re ungrateful—it often means you’re awake and paying attention to what your life is asking of you next.
Rethinking Career Growth: Why Lateral Moves Matter
The dominant career narrative tells us that progress must be linear. Whitney’s journey challenges that belief.
Letting Go of the Straight-Line Career Myth
Whitney shares how some of her most impactful career moves were lateral, unexpected, and even misunderstood by others. These pivots weren’t part of a grand plan—they were guided by curiosity, seasonality, and alignment with her life as a mother and leader.
Trusting Your Gut Over the Ladder
We explore how high performers are often rewarded for staying in their lane, which makes listening to your intuition even harder. Whitney explains how learning to trust that inner voice can open doors you didn’t even know existed.
Leading as Yourself: Defining Your Leadership Identity
One of my favorite parts of this conversation is Whitney’s framework around leadership identity.
Authenticity vs. Leadership Identity
Authenticity matters—but Whitney takes it a step further. Defining your leadership identity means clarifying your operating principles at work: how you show up, lead, make decisions, and handle pressure.
Why Masking Yourself Is Exhausting
Whitney opens up about the cost of dimming parts of herself early in her career—especially as a young woman in male-dominated rooms. Over time, she learned that her personality, energy, and perspective weren’t liabilities. They were her edge.
Magnetic Leadership: What Draws People In
We talk about what actually makes a leader magnetic—and it’s not charisma or perfection.
Confidence Rooted in Clarity
Magnetic leaders are anchored in who they are. They lead with intentionality instead of defaulting to what’s safe or expected. That grounded confidence—balanced with humility—is what people feel and respond to.
Why It Changes How Work Feels
Whitney explains that magnetic leadership doesn’t just drive results. It transforms how you experience your work. When you stop trying to be someone else, the work feels lighter, clearer, and more sustainable.
The Silent Dream: When Staying Costs More Than Leaving
This part of the conversation is deeply resonant for so many women.
Listening to the Whisper That Won’t Go Away
Whitney shares how her “silent dream” began during maternity leave—a persistent curiosity about what else might be possible. It didn’t lead to an immediate leap, but it did spark years of intentional preparation.
Betting on Yourself (Without Burning the Bridge)
We talk about why chasing a dream doesn’t mean pulling the ripcord overnight. Strategy, validation, and support matter. Whitney’s path was built quietly over years before she ever left corporate.
Motherhood, Guilt, and Owning Your Balance
This episode also goes deep into the realities of working motherhood.
Letting Go of Everyone Else’s Rules
Whitney speaks candidly about the guilt that comes from constant commentary—at work and at home—and how it slowly erodes confidence if left unchecked. The shift came when she decided to define success, balance, and motherhood on her own terms.
Why Balance Is Something You Own
We unpack the idea that work-life balance isn’t something a company gives you. It’s something you actively shape through boundaries, clarity, and hard conversations—again, and again, and again.
Practical Support That Actually Helps (Including a House Manager)
One of the most actionable parts of this episode is Whitney’s breakdown of how she and her husband manage the logistics of two intense careers and family life.
Investing in Support Without Shame
From weekly planning check-ins to hiring a house manager, Whitney explains how outsourcing certain tasks wasn’t indulgent—it was strategic. Support systems don’t replace your role; they protect your energy.
If this episode resonated with you, I hope it gives you permission to explore what your own quiet pull might be asking of you. Success doesn’t have to be abandoned—it can be redefined.
You can learn more about Whitney and her work at whitneyfaires.com, and connect with her on LinkedIn and Instagram.
And if you’re in a season of questioning, remember this: awareness is not a problem—it’s the beginning of alignment.
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