Welcome to The New Dorothy!

This is a little corner of the internet where I share the real stuff:

The strategies, systems, and stories behind building a career (and life) that doesn’t require waiting until retirement to actually live.

By way of introduction - I’m Brooke Roberts—currently VP of Marketing at Via, an investor-backed edtech startup powering global engagement in higher ed.

Before that, I built and sold multiple online businesses, ran the world’s largest meaningful travel search engine, and spent 20+ years working in international education.

I’ve lived and worked across six continents and over 60 countries, built a six-figure digital product business from a backpack, and found time to do a TEDx talk.

This newsletter is part memoir, part playbook.

Sometimes it’s a personal story. Sometimes it’s startup insights. Sometimes it’s how I manage a side hustle and a 9to5 while working from a rooftop in Budapest, Bangalore, or Buenos Aires.

Why The New Dorothy?

There’s a literal reason—and a more whimsical one.

Literally:

  • Dorothy from the Wizard of Oz—the one with the ruby slippers—was from Kansas. So am I.

  • I grew up on a farm in rural Kansas, left at 18 to study and work all over the world, and eventually made my way back to Kansas City in my late 30s.

  • The New Dorothy was the name of my first blog and has been my social handle since 2005. It’s stuck.

Whimsically:

  • Like the original Dorothy, I always dreamed of a life beyond the pastures that surrounded me.

  • But for me, the yellow brick road wasn’t about getting back home—it was about seeing what’s possible when you follow your own path.

  • The New Dorothy is about building a life that’s fully yours—on the road, at work, in your business, and wherever you choose to land next.

  • It’s not about escaping. It’s about expanding.

What I write about:

  • Startup & solopreneur strategy

  • Travel as a way of life, not a vacation

  • Side hustles (the scalable, realistic kind)

  • Smart, flexible ways to earn digital income

  • Personal branding that actually opens doors

  • Remote work and building a location-optional career

  • Oh—and what it actually looks like behind the scenes

If that sounds like your kind of vibe, you’re in the right place.

I send out the newsletter every Tuesday morning.

No fluff. No recycled tweets. Just useful, honest content from someone doing the thing.

While you’re here: Check your inbox and move my email to your Primary tab so I don’t get ghosted by Gmail.

Glad you’re here.
See you Tuesday…

—Brooke
The New Dorothy

Brooke Roberts - The New Dorothy