Writing · On Substack

Welcome to the messy middle.

From the anchor desk to the founder's desk. Honest essays about starting over, building something of my own, and the lessons I'm learning along the way.

Jillian smiling on a white couch, holding a journal

Latest essays

Lessons from the pivot

See all essays
Cover image for There Are No Failures, Only Reroutes

Newest · Oct 21, 2026

There Are No Failures, Only Reroutes

What nearly 20 years of breaking news and a relentless work ethic taught me about the hard days of business.

Read on Substack →

Cover image for Starting Over Shows You Who Your People Are

Oct 18, 2026

Starting Over Shows You Who Your People Are

Not all attention is support. But all of it tells you something.

Read on Substack →

Cover image for A Letter to Anyone Who Knows a Business Owner

Oct 8, 2026

A Letter to Anyone Who Knows a Business Owner

Because the little things aren't little. 10 ways to support someone building something from the ground up.

Read on Substack →

Cover image for Three Summers Without the Beach

Oct 3, 2026

Three Summers Without the Beach

The parts of starting over no one sees, and an honest answer to the question I get asked most.

Read on Substack →

Cover image for The Trap of Being Your Own Boss

Jun 16, 2026

The Trap of Being Your Own Boss

The qualities that make you good at running a business are the same qualities that make it almost impossible to stop.

Read on Substack →

Cover image for I Love What I Do. That Doesn't Mean It Isn't Work.

Jun 9, 2026

I Love What I Do. That Doesn't Mean It Isn't Work.

Why fulfillment doesn't come from avoiding work, but from believing in it

Read on Substack →

Never miss an essay

Get every new essay in your inbox.

Real stories from someone figuring it out in real time. Subscribe on Substack and come along for the ride.

Get the newsletter