Work on the founder, not just the business.
Private advising for founders whose business has become personal. I'm Jennifer Chaiken, a licensed psychotherapist who has spent more than a decade building and scaling a multi-location company. I help you see the pattern behind the decisions that keep repeating, so you lead the business instead of it leading you.
Is this for you?You can see your pattern now. The hard part is catching it in real time: in the middle of a hire, a pricing decision, or a client you can't say no to.
This is for founders who:
Recognize their pattern but keep slipping back into it under pressure
Look back on big decisions and realize something other than strategy was driving them
Are tired of advice that doesn't stick, because the real problem isn't strategic
Want a thinking partner who understands both the inner work and how a growing business actually runs
Are building something that matters and want to lead it with more clarity
Why this is differentMost coaches work on the business. Most clinicians work on the person. I've been both the clinician and the owner, so I work on the space between them: how who you are shows up in what you're building.
The pattern side. We pinpoint where your pattern came from, what sets it off, and how it's quietly shaping your decisions about money, hiring, delegation, conflict, and growth.
The business side. We build the systems, structure, and decision-making habits that let your business run without your pattern in the driver's seat.
When you can name the pattern behind a decision, you get to choose again. That's where conscious leadership starts.
Your relationship with your businessEvery founder is in a relationship with their business. Most have never looked at it that way.
I’ve spent my career helping people understand the relationships that shape them. The one between you and your business follows the same rules. It can be steady and secure, or it can quietly take over your life.
It can feel like a marriage. The honeymoon that made you start. The resentment you don’t say out loud. The boundaries that slipped somewhere along the way. Staying out of obligation instead of choice.
It can feel like your child. You protect it, sacrifice for it, and lose sleep over it. You struggle to let anyone else care for it, and you feel every setback as your own failure.
It can become your identity. When the business has a good month, you feel worthy. When it struggles, so do you. Somewhere along the way, it got hard to tell where you end and it begins.
None of this means something is wrong with you. It means you care. But the relationship you have with your business shapes every decision you make inside it. When we look at it clearly, you can build one that lasts: where you lead the business, instead of the business running you.
Ways to work together
Recommended starting point. Over one month, we meet weekly for four 2-hour sessions focused on your relationship with your business. We trace the pattern behind the decisions that keep repeating: where it comes from, what it's costing you, and what it's protecting. At the end of the month, you receive your written Founder Pattern Map and clear next steps.
The Pattern Deep Dive
Ongoing, one-on-one partnership. A 90-minute private session each month, written takeaways after every call, and support between sessions when something can't wait. Pattern work and business strategy, together. Three-month minimum.
Monthly Advising
Your pattern doesn't stay inside you. It shows up in how you work with your partner, your leaders, and your team. Through an in-depth intake and optional confidential conversations with key people in your business, I map the dynamics shaping how your company runs. You receive a written Relational Map and a debrief with clear recommendations. Nothing your team shares is attributed to them without their consent.
The Relational Audit
How it worksA simple, personal process. No pressure, and no commitment until we both know it's the right fit.
Apply. A short application so I can understand where you are and what you need.
Talk. A complimentary consultation call to see if we're the right fit.
Plan. If it's a fit, you'll receive a tailored proposal.
Begin. We start with your questionnaire and a full intake.
I work with a limited number of founders at a time.
Meet your advisor
Licensed Psychotherapist
Relationship Expert
Founder Advisor
Hi, I'm Jen.
I'm a licensed psychotherapist, a relationship expert, a founder advisor, and a business owner. I've spent more than a decade building and scaling a multi-location company with a large team: hiring and leading dozens of people, expanding into new locations, navigating growth that sometimes outpaced our systems, and making the kind of decisions that keep founders up at night.
Somewhere in the middle of that growth, I noticed something I'd seen in my clinical work countless times. Only this time, it was mine. The same patterns that shaped how I showed up in my life were quietly making business decisions for me. Who I hired, and who I hesitated to let go. When I said yes when I meant no. What I held on to that I should have handed off.
Once I could pinpoint those patterns, I started making decisions on purpose instead of on autopilot. I led with more clarity, delegated with more confidence, and built from somewhere steadier. The business grew as I did.
That's what FounderSelf is built on, and it's what I bring to every founder I work with: a clinician's eye for patterns and an owner's understanding of what it really takes to build something. I've sat in your chair. I know how much of the business lives inside the founder.
QuestionsIs this therapy?
No. This is business advising, informed by my clinical training. We focus on how your patterns show up in your business and leadership, not on clinical treatment. If therapy would serve you better, I'll tell you and help you find the right support.
Do I need to take the quiz first?
It's not required, but it helps. If you haven't yet, it's a great place to start: take the quiz.
Where are sessions held?
All sessions are virtual, so I can work with founders anywhere.
What does it cost?
Investment depends on the type of work. We'll talk through options on your consultation call.
I've done the 6-Week Path. Is this the next step?
Often, yes. The Path helps you see and start shifting your pattern. Advising is where we work on it in real time, inside your actual business.
Ready to look at the founder behind the business?
Tell me a little about you and your business. I read every application personally and will reply within a few business days to set up a complimentary consultation call.
I work with a limited number of founders at a time.