A Lesson in Letting Go of the Shoulds

We’ve all been there.

You do what you're "supposed" to do.
Climb the ladder. Hit the targets. Say yes. Push through.
Only to wake up one day wondering… How did I get here?

That’s precisely where James found himself when he joined the Failure to Quit coaching program. On paper, he was thriving—VP title, six-figure salary, high-profile projects. But inside? He was exhausted, unfulfilled, and drowning in the weight of expectations that weren’t even his own.

“I did everything I was supposed to do. Why do I feel like I lost myself?”

The Breakdown That Brought Breakthrough

Our first session wasn’t about strategy. It was about surrender.

James didn’t need a productivity hack—he needed permission.
Permission to stop chasing the “shoulds” and listen to what mattered.
Permission to question the path he was on.
Permission to admit that even success can suffocate when it’s not aligned.

So we began with a pause—a deep one.

We mapped his core values, identified energy drains, and asked one game-changing question:

What if success didn’t look like more, but looked like you?

That question unlocked everything.

From Resignation to Redirection

James didn’t quit his job the next day. That’s not the point of Failure to Quit.

But he quit something else—the false narrative that success must be earned through burnout.

He restructured his team. Delegated more. Rebuilt his boundaries.
He initiated courageous conversations with leadership.
He started writing again—something he hadn’t done since grad school.
And six months later, he stepped into a role better aligned with his strengths, leading with purpose, not pressure.

Let This Be Your Wisdom Moment

Your setback is not the end. It might just be the setup.

And like James, your transformation begins when you stop trying to “fix” the symptoms and start asking more profound questions:

• What is this moment trying to teach me?

• What parts of myself have I silenced to survive?

• What if I permitted myself to rewrite the script?

The truth is: the strongest leaders are often born from the most broken moments.
Not because they never fail, but because they finally stop faking it.

💬 Ready to Turn Your Setback Into a Setup for Success?
Apply now to join the Failure to Quit Group Coaching Experience and rediscover what leadership feels like when it’s rooted in purpose, not pressure.

🔗Schedule Strategy Session