Concierge Coaching
Private Strategic Life Advisory with Diane Cunningham
When life gets complicated, you have someone to call.
One year of private advisory with me, with direct access by phone, Zoom, text, and voice message—including evenings or weekends when life requires it.
This is for women and men navigating the things that don’t fit neatly into a coaching session:
- Major decisions: With $$, business, life transitions
- Family situations: Adult children situations, empty nest transitions
- Business transitions: Selling a business, expanding or an identity shift
- Aging parents: caregiving stress, financial decisions and complicated family dynamics.
- Recovery: from addictions, transitions, moving.
- Relationships: with family, spouse, clients, staff.
- Loss: Death, Divorce, Retirement
- Reinvention: After big change
- Faith: How it impacts your business and life
- Money: Change in monetary status, higher or lower.
The conversations you don’t know how to have. The decisions you don’t want to make alone. Patterns that keep repeating that you want to change.
You don’t need to wait for our next scheduled appointment.
You call me.
I listen.
I ask questions.
I help you see what you can’t see from inside the situation.
We figure out the next brave thing together. The next step that makes sense.
Your Private Retainer Includes:
One year of concierge access to me, including:
- Direct phone, text, and voice-message access
- Zoom conversations whenever deeper discussion is needed
- Priority access when something urgent comes up
- Evening and weekend conversations when necessary
- One monthly private strategy session (phone or zoom) 45-90 minutes
- Two in-person half-day INTENSIVES during the year, including lunch or dinner
- Access to my workshops and private events during your year
- Books and resources from my library as useful
- Support preparing for important conversations and decisions
- Referrals to appropriate professional resources when something falls outside my scope
We start our engagement with a thorough Deep Dive conversation so that I understand who you are NOW. Not who you pretend to be, who you are.
Although I am a former therapist, this is not therapy. This is also not medical care, legal counsel, or crisis intervention.
It is something much simpler:
A trusted advisor who knows you, knows your story, and is already in your corner when life changes.
Personal Note: I created this opportunity during August 2026 as I sat in a hospital parking garage in California wishing I could set up a phone session with my therapist in Texas but knowing that she was not allowed to do that because of the rules of therapy. In coaching, this is allowed. This is normal. To talk “in the midst” of it.. even in a parking lot or the ER waiting room and not have to wait 3 weeks for a session.
$20,000 / Year
I accept three Concierge clients per year.
By private application and conversation only. It is pay in full upfront due the nature of the work.
Diane Cunningham
Strategic Life Advisor + Courage Concierge
You don’t have to make the biggest decisions of your life alone.