God Told Me to Let Go—And I Was Scared
There’s a moment that can be harder than failure.
It’s the moment when God says, “Let go.”
And everything in you wants to scream back, “But I worked so hard for this.”
Today, I want to talk about two moments in my life when I knew God was asking me to let go—once when I was a lawyer, and once as a founder.
And how in both moments… I was terrified.
The Lawyer I Promised I’d Be
My dad always taught me, “You are your word.”
So from age 8 to 21, all I talked about was becoming a family lawyer and working with children.
And because “lawyer” fits neatly into one of the three West Indies–approved professions—doctor, lawyer, or engineer—no one questioned my dream. No one asked whether it aligned with my actual gifts or whether I truly loved the work.
I went to Harvard Law School unwavering in my commitment to be the exact kind of lawyer I said I wanted to be at age 8.
Life threw its curveballs—my family was struggling, I developed chronic pain, our finances were stretched thinner than ever.
But I was resilient. And to me, that meant consistent.
I would not be moved off my original trajectory.
I would be a woman of my word.
I was going to be a lawyer.
But God Was Whispering Something New
Even in law school, God was planting seeds for something else.
I started hanging around the J.D. Admissions Office. Someone gave me a copy of The Privileged Poor. I began interviewing and befriending admissions deans—not because I wanted to become one, but because I was curious.
After law school, I clerked for a judge and joined a family law firm. My health issues got worse, the pandemic hit, and I finished my graduate certificate in educational consulting—again, “just for fun.”
Eventually, I looked around at my life and realized:
I had become exactly what I said I wanted to be.
And I had never been more unhappy.
The Breaking Point
Two months before I hit that wall, I joined a church fast and prayed,
“God, maybe one day—far in the future—I can do admissions work full-time.”
I was hoping for a slow fade.
But God said: Let go now.
At the time, I was working part-time with students while still full-time at the law firm.
I was in constant physical pain. I cried in the bathroom between meetings. I sat on the office floor with nerve pain running down my legs, a heating pad on my hip.
I loved my students. I loved that work. But I was holding on to a life that was breaking me.
And still… I couldn’t imagine quitting.
I thought leaving the law meant I wasn’t strong enough.
That I didn’t have the grit.
That I’d be letting my family, mentors, and community down.
I didn’t leap into entrepreneurship.
I was pushed—by grace.
By a God who loved me enough to disrupt the plan I idolized.
Letting Go… Again
Fast forward a few years, and I found myself in another “letting go” moment—this time, with something I had built.
My edtech startup, Outline It, was at a crossroads.
We had raised money. Joined top accelerators. Served thousands of students.
It was working… until it wasn’t.
The rapid rise of AI made our model financially unsustainable. I had to ask myself:
Do I go deeper into debt to keep this going… or do I shut it down?
And shutting it down? That meant telling my friends and family—people who had invested thousands of dollars—that they were going to lose all of it.
I was terrified.
Not just of failing, but of what people would think of me.
The Hardest Part Wasn’t the Loss
But here’s what happened:
No one was mad at me.
In fact, many of the people who supported me then still support me now.
That moment taught me something I’ll never forget:
People’s love and belief in you isn’t always transactional.
I learned how to be transparent.
How to have hard, grown-woman conversations.
How to separate my worth from my wins.
I learned that success isn’t just about momentum—it’s about alignment.
And that obedience often looks like closing the door before the applause.
Letting go didn’t feel like a win.
But looking back?
It wasn’t a loss either.
If God Is Asking You to Let Go…
Maybe you’re in that season right now.
Maybe God is asking you to let go of something that once defined you.
A dream. A relationship. A role. A version of yourself.
Please hear me:
Letting go doesn’t mean you gave up.
It doesn’t mean you failed.
It means you were faithful.
Sometimes obedience looks like:
Leaving the job
Closing the doors on something you built
Walking away before the world claps for you
But there is peace on the other side of letting go.
Peace I didn’t earn—but peace I received the moment I stopped grasping and started trusting.
If you're scared right now—I get it.
But I promise you, God can do more with your surrender than you ever could with your striving.
You don’t have to hold it all together to be strong.
You just have to be willing to let Him lead.
If This Spoke to You…
Drop a comment.
Share this with someone who’s struggling to release what’s no longer serving them.
💛 And if you’re ready for more reflection, download my free Resilience Reflection Journal to help you process what letting go might look like in your life.
You’re not weak for letting go.
You’re already winning.
