Hi there!

I'm Autumn Hillebrand


Welcome! I'm so glad you're here. I've been married to my husband for over 25 years, and together we've spent the last several years chasing a simpler, more adventurous life.

Before we became empty nesters, we had a dream: live on a sailboat and travel while we were still able. Not someday. Not after retirement. Before life got away from us.

So we did it. We each left our steady jobs (mine was an 18-year government career), sold almost everything we owned, and moved aboard our sailboat. We lived that dream for a while, and it changed how I see everything.

What I learned along the way

The hardest part wasn't the sailing. It was the letting go: the stuff, the identity tied to my career, the idea of what life was "supposed" to look like at our age. And the most freeing part was giving myself permission to do it anyway.

I also learned what I wish I'd known sooner. If you want freedom to last, you need a way to earn income from almost anywhere. That's become my passion.

Today we're back on land in Florida, in a home we keep simple on purpose. We take the van out whenever work allows, and I'm building a life and business I don't need a vacation from.

What you'll find here

Reinventing Monday is for women 40+ who are ready for what's next.

Simplify

Real-life help with downsizing, decluttering, and keeping the memories that matter

Thrive

Ideas and tools for building income on your own terms in your second act

Wander

Inspiration for traveling more and living more flexibly

Start with permission

You’ve been last on your own list long enough.

My free Reclaiming Slip helps you name what you’re ready to let go of and give yourself permission to go after what’s next.

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