Enneagram 2 | Jackie Contessa

In this episode of Inside Story, host Kristin Messegee (@enneagram_6_coach) sits down with Enneagram coach Jackie Contessa (@tablefor9co).

Jackie talks about Twoness and pulling back the curtain on pride, need, the fear of lovelessness, the desire to be chosen, and the quiet grief Twos carry when they disconnect from themselves.

Together, they explore what it means to hunger for love, how pride cuts Twos off from their own needs, and why real connection requires letting ourselves be seen without manipulation, performance, or earning.

This conversation goes everywhere:

• learning to meet your own needs

• the Two’s relationship with shame

• repairing conflict

• how image types lose themselves

• why boundaries can be the deepest act of love

• what opens up when a Two stops curating who they are

If you’re a Two—or love a two—this episode is a masterclass in understanding what’s happening under the hood. It’s tender, hilarious, raw, and full of the kind of truth that reshapes how we show up for each other.

Follow the work:

🌿 Kristin: instagram.com/kristinmessegee

🌿 Jackie: instagram.com/tablefor9co