Hi, I’m Holly, a transition coach and mentor.
I helps individuals who feel lost, stuck, and unmotivated move through endless or messy transitions and toward greater clarity, joy, and life satisfaction.
Do you have a history of addictions? Are you a highly successful, middle-aged, potentially neurodivergent or burned-out woman who has lost the plot, can’t figure out a way forward, can’t imagine a life beyond this, and is also too tired to even read this sentence all the way through??!
You’re in the right place. Keep scrolling to learn more, or book time with me today.

There is (very bright) future you can’t see yet.
If you feel like you’ll never get to the other side of what you’re in, find peace, escape your self-sabotaging behavior/ingrained patterns, or “feel like yourself again”…this is good news. You’re in a better place than you think (as evidenced by the fact that you know these things about yourself).
You don’t have to fix yourself before you begin (or fix yourself at all!), and you don’t have to keep waiting to arrive.
You can arrive now. You can feel clarity now. I can help.
Who this is for:
My clients work on a range of issues, goals, and projects. Most are at some crossroads in multiple or converging areas (career/vocation, relationship structure, other significant loss such as identity, marriage, motivation, recovery, aging), burnt out, and at a loss for where to go next. Some have a history of addictions and have been in recovery for some time.
This could be for you if…
Doing any more work on yourself makes your insides curdle. You’ve done it. It’s still the same. You're tired of working on yourself. You should be done by now.
You “had it” and lost it (sobriety! clarity! purpose! dream career! dreams! will! desire!)
You’ve made a change (or a change has been made for you), and you need support moving through the in-between.
You’re doing everything the books say to do, but nothing is happening; you’re afraid you will always be stuck like this.
The things that used to excite and motivate you (big goals) don’t anymore, and you don’t know if you’ll ever feel the drive you once had again.
You want to feel like yourself again.
What we can cover in 60* minutes:
In our hour together, I draw on my wealth of experience (see below) to ask incisive questions to get right to the heart of the matter and help you reframe blocks, uncover patterns, and find a way forward toward a more joyous and authentic life. Most people walk away from one hour with deep insight, and actionable next steps. Some folks get all they need in one hour, and I work with others over longer periods.
I have a strong and proven track record of helping folks move out of what feels impossible, broken, and stuck into greater clarity and flow.
*Note, initial calls can run over by ten or fifteen minutes, plan accordingly.
How it works/what you get
Pre-call Intake. You answer five questions to get to the root of what’s going on for you at least 48 hours ahead of our call.
Analysis. I spend time before our call reviewing your answers and designing questions to get to the heart of the matter and the most out of our time together.
Our Session. We meet for sixty minutes via Zoom or phone and work together to uncover patterns, locate where you are right now, and identify immediate action items/next steps. (Lots of a-ha moments.)
Action plan. I will send a post-call summary and action plan via email after our call so that you can take what we discussed, start making (small) changes, and begin enjoying relief.
Praise and feedback:
“I feel like a whole other person after one hour with you.” — S.C., client
“Holly’s coaching radically changed my life in just about every conceivable area. She didn’t coach me on how to have a ‘better’ life, she taught me how to make my life easier and more rewarding by working with, instead of against, my particular brain, heart, and soul.” — T.L., client
"The best thing about working with Holly is how quickly she is able to cut through the bullshit. When you are in the middle of a major life transition, it is easy to fall back into old patterns. Holly challenges if the old pattern is true. I accomplished A LOT in a short period of time, and she was exactly what I needed.” — Kimberly Tableman, CEO Espero Health
"Holly has an unbelievable quality to see the truth in people. To see through layers and protections and guards, to cut through the crap and see what's really going on. This is such a powerful gift for someone working with people's emotional scars in the way she does." — (Anon, former client in recovery-based work)
Cost, other:
The investment for each 1-hour session is $350
Sessions are fully refundable up to 24 hours ahead of time and non-refundable within 24 hours of the call. I offer 1 late reschedule (less than 24 hours’ notice) per client (lifetime).
We can explore longer-term coaching arrangements if it’s a mutual fit during our first session. Some folks get everything they need in an hour, and some folks need longer-term support.
I no longer work with people whose primary goal for coaching is to quit drinking. For support with early alcohol sobriety, I recommend Whitney Combs recovery coaching (click here for more info). Whitney has worked with me for 7+ years, and wrote much of the coaching curriculum for previous sobriety programs—she’s epic.
If you have any questions about whether or not this is for you, email us at contact@hollywhitaker.com.
About me:
You can read a more formal “About Me” here on my homepage.
I’ve had a wide range of professional and general life experiences that give me a unique perspective and skill set that combine to provide a very specific offering that will speak clearly to some (and not at all to others!).
I’m a published author and currently make a living as a writer and coach. I’m a former health care executive, CEO/founder, fundraiser, entrepreneur, small business owner, podcaster, advisor to startups and entrepreneurs, and more. In a former life, I was a sobriety and recovery coach and worked in a 1-to-1 setting with dozens and a 1-to-many setting with thousands.
I have deep experience in coaching folks and am extremely good at what I do—coaching is one of my zones of excellence. My approach relies on evidence-based modalities and is trauma-informed, deeply empathic, and to the point.
