The Success Paradox: Why Success Sometimes Feels So Empty

You’ve ticked all the boxes. Climbed the ladder with a steady flow of promotions. Secured the kind of salary and title others might envy.

On paper, it’s a complete success story.
​
Yet instead of fulfillment, you wake up with a dull ache in your chest, a quiet dread before every week begins. That blahhhh sense you’re just going through the motions.

“Why am I not happy at this level of success?”

You’ve done everything “right”: the late nights, the relentless projects, the sacrifices. From the outside, people assume you’ve got it all figured out.
​
But here’s the paradox: the very achievements you worked so hard for no longer bring joy. They’ve somehow become an anchor, weighing you down.

When Success Comes at a Price

For many women I work with, the first signs of the Success Paradox sneak in quietly over time. It often starts with:
​

• Sunday dread: that heavy pit in your stomach as the weekend ends
• Chronic overthinking: replaying every meeting, wondering if your ideas sounded “good enough”
• The endless chase: even when you hit a milestone, the satisfaction is fleeting and there’s always a “next” to prove yourself against
• Detachment from joy: hobbies, friendships, and self-care slowly disappear under the weight of work demands

​On paper, everything looks perfect. In reality? You’ve been running on empty for so long, it’s become the new normal.

Why High-Achieving Women Are Most at Risk

Perfectionism plays a big role here. Many ambitious women were conditioned early on to equate worth = achievement. Somewhere along the way, work became more than just work.

It became proof that we’re valuable, competent, and strong.

But perfectionism has a hidden edge: it whispers that no matter how much you do, it’s never enough. That whisper grows louder with every promotion, every project, every pat on the back because now there’s even more pressure not to fail.

Instead of celebrating wins, you move the goalpost and keep running.
​
It’s no wonder so many women in their late 30s and early 40s begin to ask:

Am I actually happy? Or just performing happiness for others?

What I’ve Seen in 8 Years Coaching Women Globally

Across Australia, Singapore, the U.S., London, and Dubai, I’ve coached over 500 women through burnout, perfectionism, and identity crises.

Two common themes always show up:

1. Women in burnout – ready to stop the cycle, step into higher leadership, or pivot careers, but blocked by a lack of confidence and courage
2. Women who’ve lost themselves – so laser-focused on career that their identity, relationships, and connection to joy have been pushed aside

For many, the turning point comes when a lifequake happens—a catalyst moment that sparks the question:

​Am I truly fulfilled here?

​That question is often the beginning of transformation.

Three Truths About the Success Paradox

1. Success without alignment feels empty

If your values (freedom, creativity, connection, growth) don’t align with how you spend your time, success will always feel like sand slipping through your fingers.

2. Confidence is built, not bestowed

External validation (promotions, titles, praise) can be fleeting and create dependency. Real confidence comes from silencing the inner critic and trusting your own voice.

3. Burnout is not a badge of honor

You don’t have to destroy yourself to prove your worth. The most successful leaders I’ve coached are those who protect their energy, set boundaries, and create space for their whole identity to thrive.

Breaking Free

The Success Paradox is not a life sentence. In fact, it can be the wake-up call that shifts everything.

When a client says, “I should be grateful for what I have, but deep down I’m not happy,” that’s the exact moment change becomes possible.

Here’s where I recommend starting:

• Audit your life – Compare where your time and energy go versus what you say you value most. The gaps will reveal your misalignment
• Challenge the “shoulds” – Every time you think, “I should just push through,” ask: “Whose expectation am I living under?”
• Reconnect with yourself – Your identity is more than your title. Make space for the parts of you that got left behind (creativity, health, relationships, joy!)

The good news here? You don’t need to wait for a breaking point. You don’t have to white-knuckle your way through another burnout cycle, perfectionist loop, or imposter spiral.

There is another way!

I know, because I coach women into it every day. Women who now lead with clarity, confidence, and a sense of balance they never thought possible.

Your Turning Point

👉 If the Success Paradox feels uncomfortably familiar, maybe this is your turning point.

Coaching isn’t about adding more pressure - it’s about releasing it. It’s about having a trusted guide who can help you reconnect with yourself, your values, and the confident leader you’re meant to be.

💡 Book a coaching session with me here

Janel Briggs

---

Book a 1-1 Call