Private Coaching with Caryn Gillen
Get clear. Get honest. Get what you want.
For founders and high-capacity humans who want traction without burnout.
If you’re carrying a lot—responsibility, people, decisions, ambition, family, uncertainty—you don’t need more ideas.
You need clarity you can trust. A place to tell the truth. And a coach who can hold both the big picture and the details without letting you hide.
This is 1:1 coaching for founders and thoughtful leaders who want momentum without turning their life into a performance.
View available times
Book a consultation call — 45 minutes, no pressure.
What you’ll leave the consultation call with
• A clear articulation of what actually matters right now
• The simplest 2–3 next moves
• Clarity on whether coaching together is a fit
• The simplest 2–3 next moves
• Clarity on whether coaching together is a fit
“To be successful in any business you must always be working on at least two platforms simultaneously— the big picture and the small picture. Caryn has an uncanny ability to always focus on both. She brings a new set of eyes and perspective on issues that lead to more success.”
— Rob Cohen, Restauranteur
This is for you if you want the simplest next moves, every time, with integrity.
Some coaching is inspiration. Some coaching is strategy. What we do is integration.
We’ll look at what’s happening in your real life: your patterns, your decisions, your nervous system, your leadership style, your relationships, your work, your standards—and we’ll make it workable.
You’ll leave sessions with:
• A clearer internal compass (so decisions stop taking a week)
• Clean priorities (so your calendar matches what matters)
• Language for the conversations you’ve been avoiding
• Structure that supports you (not another thing to maintain)
• Momentum that comes from truth, not adrenaline
• Clean priorities (so your calendar matches what matters)
• Language for the conversations you’ve been avoiding
• Structure that supports you (not another thing to maintain)
• Momentum that comes from truth, not adrenaline
Common reasons founders come to this work
• You’re leading people and you’re tired of carrying everything alone
• You’re successful on paper… and privately, you feel fried, numb, or behind
• You’re at a decision point and you can’t afford a messy choice
• You want to communicate with more authority and less explaining
• You’re successful on paper… and privately, you feel fried, numb, or behind
• You’re at a decision point and you can’t afford a messy choice
• You want to communicate with more authority and less explaining
• You’re navigating conflict, change, or a leadership evolution
• Your work is fine, but your life feels like it’s shrinking
• You know what you should do, but you don’t do it (and you’re done with that loop)
• Your work is fine, but your life feels like it’s shrinking
• You know what you should do, but you don’t do it (and you’re done with that loop)
“Having your coaching while building my business, increasing revenues and overseeing 150+ employees was tremendously helpful for my business’s growth — let alone my personal growth! Your care for others is remarkable, and you express it beautifully.”
— Jonah Boersma, Former Dutch Bro's Franchise Owner
My style: kind, direct, and practical
I’m warm, and I’m not here to coddle you. I’ll tell you the truth. I’ll help you see what you’re protecting, what you’re avoiding, and what you actually want.
We’ll work on two levels at once:
• Outer game: decisions, strategy, structure, communication, execution
• Inner game: the fear, the patterning, the identity shifts, the emotional capacity required to hold what you say you want
• Inner game: the fear, the patterning, the identity shifts, the emotional capacity required to hold what you say you want
If you’re ready to change—really change—this work is powerful.
“Caryn cut to the chase and didn't allow my bullshit/fear/excuses to run the show. I often wanted to run and hide during this work, but she always held space for me, told me the kind truth, and got me back on track (i.e. asked questions that called me out).”
— Katie Wood, Marketing Creative
What coaching together looks like
• We meet twice a month on phone or video
• Sessions are 50 minutes
• Support between calls via Voxer for the moments that matter, landing ah-ha’s, and reporting back on your work
• We track what you’re building, what’s working, what’s not, and what the simplest next moves are
• This is private, high-trust, and built for people who value depth and results
• Sessions are 50 minutes
• Support between calls via Voxer for the moments that matter, landing ah-ha’s, and reporting back on your work
• We track what you’re building, what’s working, what’s not, and what the simplest next moves are
• This is private, high-trust, and built for people who value depth and results
Investment starts at $1500 per month with a 6-month minimum engagement.
Pay in full saves you $500: $8500 total
View available times
You can book a consultation call to see if this is the right next step.
What tends to change
• You stop negotiating with yourself
• You get cleaner boundaries without being harsh
• You handle hard conversations faster (and with less emotional hangover)
• You lead with more steadiness and less over-functioning
• You get cleaner boundaries without being harsh
• You handle hard conversations faster (and with less emotional hangover)
• You lead with more steadiness and less over-functioning
• You make decisions from values instead of urgency
• You get your energy back because your life stops leaking everywhere
• Peace in and after big transitions
• More alignment between life and work
• You get your energy back because your life stops leaking everywhere
• Peace in and after big transitions
• More alignment between life and work
“You were the perfect coach for me at a hard time in my life and really helped me through in some seriously impactful ways. I feel like you helped me personally but also with my work as a coach, and opened me up to what coaching could be. It really changed my coaching for the better which is impacting so many people as time goes on.”
— Danny Poelman, Coach
Good fit if…
• You’re a founder or high-capacity leader who wants both depth and traction
• You’re willing to tell the truth (even when it’s inconvenient)
• You want support that’s grounded, strategic, and human
• You’re ready to be challenged—and you’ll stay in the room when it gets uncomfortable
• You want a calm business / calm life… not a new hustle identity
• You’re willing to tell the truth (even when it’s inconvenient)
• You want support that’s grounded, strategic, and human
• You’re ready to be challenged—and you’ll stay in the room when it gets uncomfortable
• You want a calm business / calm life… not a new hustle identity
Not a fit if…
• You want someone to “rah-rah” you without changing anything
• You’re looking for a quick fix or an easy button
• You want me to tell you what to do, but you don’t want to take responsibility for the choices
• You’re not willing to feel uncomfortable sometimes in service of the life you say you want
• You’re looking for a quick fix or an easy button
• You want me to tell you what to do, but you don’t want to take responsibility for the choices
• You’re not willing to feel uncomfortable sometimes in service of the life you say you want
“This is NOT an easy button. You've got to be ready to make a change and willing to get a little bit uncomfortable in the process. It's the dang inner work that'll kick your ass! Caryn will challenge you in big ways, but with gobs of kindness, too. You'll come out a new (person).”
— Katie Wood, Marketing Creative
FAQ
What happens on the consultation call?
We’ll get clear on what you’re building, what’s working, what’s not, and what the simplest next moves are. If coaching together is a fit, I’ll explain the structure and what it would look like to start.
What if I’m not a “leader” at work but I’m leading a lot in life?
That counts. Leadership shows up in transitions, health, identity shifts, relationships, and the decisions that shape your future. If you’re carrying responsibility—and you’re ready for a more grounded way to move—this is relevant.
Do you do business coaching or life coaching?
Yes. Most people don’t actually need those separated. We’ll work with the real ecosystem of your life so your growth doesn’t collapse the minute your calendar gets busy.
How soon will I feel different?
Often quickly—because clarity is relieving. But the deeper benefit is you becoming someone who can hold the next level without self-abandoning.
Do you offer a shorter commitment than 6 months?
I work best with people who are serious about change. Six months creates enough time for real traction and real integration.
If you want calm clarity and honest momentum—let’s talk.
Bring the real thing. The messy thing. The important thing. We’ll find the thread, name the truth, and identify the next clean steps.
Investment starts at $1500 per month (6-month minimum).
View available times
If it’s a fit, I’ll explain the structure and what it would look like to start.