Therapy for Founders & Entrepreneurs

Founders, leaders, and entrepreneurs often look like they’re thriving. You take risks and push ideas into the world, while appearing confident, innovative, and capable of handling the pressure. But behind the scenes, the emotional experience of building or leading anything is intense.

You’re holding vision, fear, responsibility, uncertainty, ambition, exhaustion, and the feeling that everything rests on your shoulders. There’s no off switch. There’s no clean boundary. There’s no “leave it at work.” You think about it at night, in the shower, on weekends, or during moments that should be restful. You feel responsible to your team, cofounders, investors, family, your idea, and to yourself. And that responsibility can be both thrilling and crushing.

Founders and creative entrepreneurs tend to struggle with:

  • Chronic stress

  • Self-doubt (even while appearing confident)

  • Exhaustion masked as productivity

  • Difficulty slowing down

  • Feeling disconnected from relationships

  • Imposter syndrome

  • Fear of failure or letting people down

  • Decision fatigue

  • Creative stagnation or loss of passion

  • Anxiety that feels tied to the success of the thing you’re building

As someone who’s spent years in entrepreneurial and creative leadership roles, I understand this world intimately. The intensity. The risk. The pressure to keep going. The way success can feel like both a win and a new set of problems. The emotional cost of always being “on.”

In therapy, you get a space where you don’t have to be the one holding everything. You get a place where you can be honest, not performative, about what’s actually happening inside.

We’ll explore:

  • Your relationship to ambition

  • The fear behind your drive

  • Burnout and recovery

  • Leadership identity

  • How your childhood or family patterns show up in your work

  • Emotional regulation under pressure

  • Loneliness and isolation at the top

  • Creativity and passion — and what happens when they fade

  • How to build a life that’s not swallowed by your work

I’m not here to optimize your productivity or turn you into some “executive functioning machine.” My goal is to help you reconnect with yourself: the part of you that exists outside the metrics, investors, or expectations. You can be successful in your work without sacrificing your well-being. You can lead without burning out. You can build without losing yourself.

My name is Toby Singer. I’m a Brooklyn-based therapist licensed in NY and MD.

If you’re a founder, leader, or entrepreneur who feels like the pressure is getting heavy, or if you’re simply tired of carrying all of this alone, therapy can give you the grounding and clarity you’ve been missing. Email me today to set up a free 15 minute consultation to see if we’re a good fit to work together.