I help people reconnect with their
authentic potential.Hi! I’m Jackie Contessa.
& I have a one-size-fits-all allergy.
Personality-Based Life Coach. Enneagram Coach.
Big believer in you.
I help people who feel disconnected from their true potential — but know there is more for them — break free from recurring life patterns so they can go from SELF-LIMITING to SELF-LEADERSHIP.
Not knowing my own personality type — my core why’s and recurring hows’ — kept me stuck in a cycle of recurring mistakes and unproductive patterns - in my relationships, in my work, and in my personal growth.
It wasn't until I deeply explored and studied the Enneagram that I finally found a sustainable path and language to understand who I truly am.
This journey not only helped me break free from those limiting patterns, but it also ignited a deep passion to help others do the same.
About Jackie
Jackie Contessa, referred to affectionately as, “An Iron Fist in a Velvet Glove,”*
is passionate beyond belief about making sure people have all the information available to them to help them get unstuck, for good. She is a Personality-Based Life Coach and Enneagram expert. She is a dynamic, out-of-the-box thinker and champion for personalities who believe they are limitless. Her passion is simple:
helping people break up with recurring life patterns for good so they can reconnect with their authentic potential
(because, let’s be honest, the world just sucks more when limitless people don’t live up to their potential.) Jackie helps women who lead personally and professionally tap into their BIG FAT WHY so they can live intentionally and lead authentically.
She has a working background in non-profits, human advocacy and push for legal reform, anti-human and anti-sex trafficking organizations, and working with powerhouse female survivors of domestic sex-trafficking in the United States.
She learned an important thing in these lines of work: support is never one-size-fits-all. Ever.
She is an obsessive learner and avid question-asker with a firm, but down-to-earth, approach that provides a safe space for the reformer, the giver, the achiever, the individualist, the observer, the guardian, the enthusiast, the challenger, and the peacemaker to take their unique places at the head of the table of their lives, whatever that means for them.
Jackie is from Jersey baby (eat a bagel and deal) and hates that bios have to be written in third person. That’s kind of weird (she also hates being perceived? Go figure). When she’s not cracking personality codes, transforming lives, or helping randos in public discover their personality type, you can find her reading a book (sideways), binge-watching The Office, and celebrating Diet Coke O’Clock as often as possible. She lives in NJ with her best friend (husband) and the sweetest cats, Jetta and Juni. If she’s not there, she’s in Montauk (probably crying).
*yup, she’s a 2
She leads as an instinctually intimate giver with a large propensity toward achievement. (SX 2w3)
Her favorite quote is by President Abraham Lincoln:
“If I had 8 hours to cut down a tree, I would spend the first 6 sharpening my ax.”
Love ya, mean it!
learn more about…
Gifting back to single moms
For every Deep Dive Typing session booked with me, a typing session is gifted to a single mom.
Ways to work with Jackie
Explore the different ways we can work together.
Freebies and resources
Hungry for more? Freebies and resources
Table Manners:
Table for 9’s Values
Someone “like you” is — without a doubt — capable of something “like that”.
There is no doubt about it. What you’re dreaming about is also dreaming of you. The missing link is using your personality as an asset, not a liability.
We’re not afraid of hard things because we aren’t small.
You are the main character of your life. Everything is small compared to you.
We believe in boundaries big, but we don’t believe in walls.
Both with others, and with ourselves for others. My definition of a boundary is, “A boundary is a life rule that helps the people you love — and the people you don’t — maintain access to the best side of you if you want them to have it.” Boundaries are always an attempt to keep the relationship, so we believe in them and we believe in them big.
People can only be empowered uniquely.
There is no one-size-fits anything around here. I am allergic.
The table has room for everyone, and your table should always have room for the real you.
I knew from the start, I was never going to make it if I didn’t have all 9 types around my table. I need you to be the real you because your place at the table matters. Your place at their table matters, and your authentic place at your own table matters.
Since we’re being authentic here…
I’m passionate about a human-first, non-spiritual approach to the enneagram
I am one-size-fits-all intolerant.
My top five favorite books are:
A Thousand Splendid Suns, Invisible Monsters, Anxious People, Seven Husbands of Evelyn Hugo, & The Giver. (no particular order)
I ask a lot of questions, and I love that for you.
“I’m not an entrepreneur. I’m a helper,” is basically how I run my business.
I am an enneagram online test hater — even the best ones.
I will find a way to bring up The Office daily.
I carry lime packets in my purse (you never know when you’re going to run into a Diet Coke)
I accidentally said the word, “b*tchslap” during a consultation once.
I say, “Eat the fish and spit out the bones,” ad nauseam.
There is a reason my coaching style is referred to as, “iron fist, velvet glove.”
Official-unofficial CEO of “love ya, mean it!”
I’m not for everybody, I’m for somebody.
"If what you want is authentic, insightful and helpful feedback coated with wisdom instead of sugar, then Jackie is 1000% your girl. Let her lead you...to recognize that the greenest grass is right where you're standing as long as you take the time to care for it."
-Caroline
"Jackie was kind and patient. Very knowledgeable and explained things in a graceful and comprehensive way. The session was informative but also felt collaborative. Like we were finding me together."
-Meghan
"She's the picture of the personable person; welcoming, congenial, unassuming, and eager to share her wealth of knowledge in a way that I would be receptive and intrigued. As a 5, having the time to connect on a level of shared interest--the Enneagram--was invigorating and enjoyable."
-Shannon