Deeper Connections Advanced Coaching
for Pause & Presence Retreat and Coaching Alumni
“I got so much out of it even though I have been coaching with Jessie for a long time.” - Dr. April Wazeka
Deeper Connections is a very small-group coaching program for women who have worked with me before.
It is thoughtful, practical, personal, and fun.
We go deep quickly because everyone in the group has a similar exposure to my framework and teachings.
Because the group is tiny, and I know everyone in it well, the coaching conversations are tailored to the women in the group.
We cover changing leadership roles, career transitions, kids growing up, aging parents, relationships, big decisions, and so much more.
We do book clubs and discuss podcasts in depth. And you learn many more coaching tools than you ever thought possible.
Each retreat and coaching group offers exposure to the top of the iceberg; we get you started. There is so much more to learn.
If you miss the retreat and group-coaching environment I offer and/or crave time spent with women who get it, Deeper Connections is an amazing space to be. It offers shared wisdom, support, and connection with a powerful, kind, loving, and real group of women.
Many women add one-on-one coaching sessions to the group place for the tender, complicated, or very specific thing you want to delve into.
If you have worked with me before and have been thinking, “I need a tune-up,” “I want more of that,” “ I wish I could go back,” or I wish I could feel like I did then,” this group is your chance.
This group is extremely valuable. You will get insight, inspiration, and more tools to change. The group helps you remember you are not alone. I got so many new real-life, real-time strategies for navigating challenges and thinking better thoughts. “
Program Details
Sundays 5-6:45 pm Pacific
Fall 2026 Schedule: 8/30, 9/27 , 10/18 , 10/25, 11/22 , 12/6 , 12/13
* Registration closes 9/26
*Make-up date, if a session needs to be rescheduled, is 11/29.
Group size strictly limited to 10
Option to add on discounted 1:1 sessions
You can earn up to 12 units of Accredited CME
Questions: Send me an email: jessie@jessiemahoneymd.com
“I've never taken time to actually think about how I make decisions. Even though I was a psych major, it surprises me how many cognitive biases I thought I was pretty aware of are probably influencing my decisions needlessly. The whole concept of "resulting" was pretty eye-opening.” - Dr. Emily Prazek
Choose the support that fits you best
Every option below is available only to women who have already worked with me through a Pause & Presence retreat, group coaching program, or one-on-one coaching.
You can join Deeper Connections on its own, pair the group with private coaching sessions for more personalized support, OR do PRN 1:1 coaching.
If a group, even a tiny one, doesn't feel like the right fit, as a former client, you have the opportunity to purchase three one-on-one sessions. I offer this option only to existing clients and retreat alumni because we already know one another and can get right to the work. It does not offer CME.
“Listening to colleagues who are grappling with similar issues and hearing what they have learned in prior coaching has opened up my vision for what I can release and what is possible”
- Dr. Anna Benvenuto
“When you're doing virtual advanced coaching, you're working on the strategies in the midst of your regular day-to-day. This makes it more likely that you'll be successful in maintaining healthy habits/thought patterns.” - Family Practice
What is Advanced Coaching with Jessie like?
If you loved your retreat or group coaching experience, it is more of that.
More connection. More practical tools. More laughter.
More space to think about your life with other women like you who understand both medicine and full, beautiful, complicated lives.
Because we meet over time, you get the added benefit of integrating the work into your daily life as it happens.
Will this feel like a Nicasio Creek Farm or Sagrada retreat?
It has the warmth, the fun, the sense of belonging, and the opportunity to deeply connect with women like you.
It is a place to exhale, be yourself, tell the truth, and remember what matters.
The difference is that we get to bring the work directly into real life.
The hard conversation is next week. The leadership role is changing now. Your teenager is having a teenager moment tonight.
We can pause, look at what has happened and is happening, and practice using the tools in real time.
What if I do not have one specific thing I need to work on right now?
Totally fine.
You do not need to arrive with a problem or an agenda. If you simply want to feel like you did on the last day of the retreat, or be as open to possibilities as you were after your group, or are ready to evolve, expand, and grow again, it’s a fit.
Even if you have no idea why you want to do it, your intuition is just telling you to; you will learn a ton.
What we talk about
Anything and everything. Relationships. Parenting. Aging parents. Leadership. Transitions. Career decisions. Boundaries. Self-worth. Staying in medicine. Leaving medicine.
What if I miss a session?
Life happens. People miss a session or two. Recordings are available, and you still get incredible value from being part of the group. Sometimes even more.
Can I add one-on-one coaching?
Yes. Many women do.
The group offers the wisdom, recognition, support, and belonging of community. One-on-one sessions are a place to go deeper into the tender, complicated, or very specific thing that is yours.
“Investing in reflection with guidance has created more peace and contentment in my life. “
- Dr. Anna Benvenuto