Small Business Owners Group

A space for the human side of business ownership

Owning a small business is often described in terms of hustle, strategy, and growth. But behind those headlines are quieter truths, like loneliness, self-doubt, decision fatigue, and the strain of having your identity tied so closely to your work.

This group offers a confidential space to talk about those realities with others who understand.

Group Details

  • When: Friday 12pm PST/3pm EST

  • Length: 60 minutes

  • Where: Online via Zoom

  • Cost: $80 per session, with a few sliding scale spots

  • Format: Ongoing weekly group

What to Expect in a Session

Sessions focus on conversation and connection, not on setting quotas or tracking metrics.

Together we will:

  • Share current challenges in an atmosphere of respect and privacy

  • Explore feelings around leadership, financial uncertainty, hiring and firing, relationships with staff and clients

  • Discuss the emotional toll of risk-taking, responsibility, and blurred boundaries between self and work

  • Learn to notice stress signals (e.g., burnout, isolation, decision fatigue) and respond with compassion

  • Offer each other validation, perspective, and solidarity

You won’t be asked to present goals or progress reports. This is a space to speak openly and feel supported.

Who This Group Is For

This group is designed for business owners who:

  • Have established business that have been running for at least two years

  • May have employees or contractors, or simply carry the full weight of running the company themselves

  • Feel the emotional pressures of ownership, such as worry about staff livelihoods, uncertainty about the future, strain on relationships, or the sense that their business and self are too intertwined

  • Want a place to be understood and to hear how others navigate similar challenges

  • Are located in New York or California

Financial Info

  • Sessions are $80 each

  • A few reduced-fee spots are available for accessibility

  • You are responsible for all group session fees, including those for missed sessions.

Getting started

If you’re curious, you’re welcome to schedule a brief 15-minute consultation call to ask questions and get a feel for the group before joining.

Book a Consultation Call