Hey there!

Becca Gregory, owner of A Skillful Life, coach to big-feeling high achievers leaning back
A headshot of Becca Gregory, owner of A Skillful Life, coach to sensitive high achievers smiling into the camera, wearing a white blouse

I’m Becca

(not Rebecca and certainly not Becky).

  • I’m an eldest daughter (IYKYK) on a mission to age backward.

  • I’m in the middle of a full-time slow traveling experiment—one country, one existential crisis, one favorite cafe at a time.

  • My camera roll is 80% strangers’ dogs, and I regret nothing.

  • I firmly believe the potato is the perfect food. As the incomparable Dolly Parton said, “I never met a spud I didn’t like.”

And I guide (sometimes secretly) big-feeling, high-achievers quiet the inner critic, build self-trust, and break free from the “shoulds” that keep them stuck—so they can make confident decisions, show up authentically in relationships, and move through life with ease.

I love people who think & feel deeply

My clients don’t take things at face value. They think, analyze, and process deeply. Sometimes to avoid how deeply they actually feel. They are loyal friends, sharp observers, and total bullshit detectors. They are some of the most eager, hilarious, and growth-driven people I know. As you can see, my work is 100% self-serving. No martyrdom required.

Because my people are just the best, I simply must see them achieve their most fulfilling lives, careers, and relationships. Seeing you feel capable, confident, and fundamentally good enough is a compulsion.

My genius is in solving problems. My superpower is getting unstuck.

Whether you have a clear destination but don’t know how to get there, or you just know that this isn’t it—I got you.

You tell me where we’re starting, and together, we’ll figure out where you’re going. My expertise lies in crafting a custom roadmap to bring that new reality to life.


Unlike other self-development practitioners, I am a clinically trained social worker.

I integrate evidence-based practices, science-backed strategies, and a little woo to help you create lasting change, self-trust, and contentment. I am passionate about what works, pulling from both research & lived experience.


The personal growth world loves neat, one-size-fits-all advice, but you’ve followed the rules, done the work, and still feel stuck. ‘Just trust yourself’ sounds great in theory, but no one tells you how. That’s where I come in.

Becca Gregory, owner of A Skillful Life, coach to sensitive high achievers using a laptop

What if you could stop…

second-guessing yourself and trust your instincts.

overanalyzing every possible outcome and make bold decisions.

chasing what ‘makes sense’ and start choosing what feels right.

clinging on to “shoulds” and be honest with yourself.

shaming yourself into change & start leading yourself with trust.

You’ve mastered being ‘good.’ Now it’s time to master being you.

If something is both exciting and terrifying, then you should definitely pursue it.