Letting Go Isn’t Giving Up — Here’s What I Learned

LETTING GO ISN’t GIVING UP

Shannon’s March update

If you know me, you know I love a big, bold, audacious goal. I’ve chased more than a few in my life — and I’ve been lucky enough to achieve some really incredible ones. But I’ve also learned something just as important as dreaming big: knowing when to let go.

I’ve always had a pretty good gut feeling for when something just isn’t working anymore. That doesn’t mean letting go is easy. In the moment, it can feel like failure. Like I’m giving up. Like I’m letting people down — especially myself. But with a little space and a lot of reflection, I’ve always known, deep in my soul, that stepping away was the right move.

Retiring from competitive skiing while still ranked third in the world?

Selling our coffee roasting business and three coffee shops when we were rapidly expanding?

Walking away from the virtual women’s leadership program I built from scratch?

All incredibly tough decisions. All moments that brought up so many emotions — sadness, doubt, fear, even shame. Because when you’re someone who prides herself on being resilient, on pushing through, on never quitting… letting go can feel like betrayal.

The truth I’ve come to is that letting go isn’t weakness. It’s wisdom. It’s strength. It’s choosing alignment over achievement.

When you sit still long enough to hear your why — when you give yourself the space to actually feel it — those hard emotions start to soften. They’re replaced with peace. With pride. With an honest, unshakable clarity that says, This is right. This is true.

So how do you know when it’s time to pivot?

These are the three critical questions I come back to every single time I find myself at a crossroads.

1. How are you spending your time?

We get one life. That’s it. And if you’re spending most of your days doing something that drains you — not just here and there, but on a regular basis — that’s a flashing red light. Sure, we all have parts of our day that are boring or frustrating or just not fun (hi, email). But overall, you should love your life more than you don’t.

2. Are you chasing your dream?

This one’s huge. Because sometimes, without realizing it, we start chasing someone else’s version of success. Maybe it’s what your parents wanted. Or what looks shiny on Instagram. Or what you used to want, but no longer do. If you pause and realize that the goal you’re chasing no longer lights you up — or never did — that’s your sign. It’s okay to walk away. In fact, it’s necessary.

3. Is something else calling you?

Sometimes we’re so focused on this thing that we miss the quiet pull of that thing. And the only way to give that new dream space to grow? Is to let go of the one that’s no longer serving you. There’s no shame in that. There’s magic in it.

Listen — I know it’s not always simple. Life gets messy. You’ve got responsibilities, people counting on you, a calendar packed to the brim. It’s easy to feel stuck. But let me tell you something I’ve learned again and again:

It starts with one decision.

One decision to be honest with yourself.

One decision to trust what your heart already knows.

One decision to believe that changing direction isn’t giving up — it’s growing up.

So if you’re sitting in that in-between space, wondering if it’s time to let go, I hope this gives you permission to stop gripping so tightly. You are not a failure. You are evolving. And that is so much braver than staying stuck.