About Jenny

Hi! I’m Jenny. For 20 years I was the ‘good employee’ … overworked, underpaid, and fearful of losing the “security” of my jobs as teacher, counselor, and executive.

The day I was unceremoniously fired from a company I’d poured my heart into (and made a lot of money for!) for 10 years, I realized that I was the only one who could create “job security” for myself.

I vowed I’d never again work for someone else, and turned my copywriting side-hustle of many years into my full-time work ... truly believing that entrepreneurship was the path to financial security — and the time freedom I craved.

But the “overworked and underpaid” scene just repeated itself, because the online coaching world (it turned out) was a tangle of “shoulds” & “musts” that kept me on a hamster wheel for a looooooong time.

When I finally decided to stop doing “all the things” and to forge my own path … everything changed.

I created simpler systems that allowed me to sell more, doing less … and Relaxed Marketing™ was born.

Fast forward nearly a decade — and I’m still 100% unemployable … and still working 24/7.
(24 hours a week, 7 months a year — bet you didn’t see that coming! ;)

These days …

I teach coaches, doctors, therapists, healers and other transformational experts to create a relaxed, lean, sustainable business flow. that aligns with their energy & preferences ...

And how to communicate their unique value without hype-y copywriting or bro-marketer tactics that don’t align with their values & integrity.

Check out my Everything Page for ways I can help you sell more, doing less.

Jenny Oby, Business Coach

I’m most passionate about …

  • Living my life and running my business by The Golden Rule.

  • Making life & business simpler — and sharing my methods along the way. 

  • Finding ways to make complex ideas easily understood in the teaching materials I create for my clients.

  • Teaching seasoned experts how to write about ‘what they do’ in a way that feels good, and calls in exquisite-fit clientele.

Some fun facts about me …

  • Old magazine ads! I used to spend hours poring over 1940s Life magazines … and my beloved 8th grade history teacher thought I was studying WWII. 

    In reality, I was mesmerized by the long-form ads — sorry, Mr. Penley! — which obviously shaped my future destiny as a conversion copywriter & messaging strategist / content coach.

  • Stand-up comedy!

    No kidding — this introvert / ambivert did stand-up … while waiting tables … and telling jokes in a Maine accent (it’s a real thing).

  • Exploring the rocky coasts, enchanting woods, and pristine lakes of my native state of Maine … or perhaps hiking the cactus-lined trails and sun-drenched desert of my adopted (and beloved) Arizona.

  • Lakewood Theatre, America’s oldest continuously running summer theater. I’m a hobby deltiologist (old postcard collector!), and I used more than 100 of my own early 1900s postcards of Lakewood in the book.

  • The “Velvet Hammer”! My ability to firmly (yet oh-so-kindly) guide my clients earned me this nickname, and I embrace it proudly.

Wondering Where To Start?

Visit my Everything Page, which is a handy list of all my current offers, free and paid.