Partnering with Family: The Unexpected Challenge in Entrepreneurship
The part of starting a business that scared me most wasn’t the risk. It wasn’t the uncertainty. It wasn’t even the possibility of failure.
It was partnering with my sister and brother-in-law.
Family businesses have a mixed reputation. According to the Family Firm Institute, approximately 70% of family businesses fail or are sold before the second generation takes over, and only about 30% survive into the third generation. Stories of strained relationships, broken communication, and blurred personal and professional boundaries abound. I didn’t want that to be our story.
Choosing Therapy as a Business Strategy
When we decided to build Mid-Day Squares together, we made one decision from day one that shaped how we would operate: we committed to going to therapy together every 7 to 10 days. Not when things got bad. Consistently. Perpetual. No matter what.
At the time, I wasn’t fully convinced. It felt unnecessary, slightly uncomfortable, maybe even excessive. Why would we invest that kind of time and money when nothing was wrong?
Nearly eight years later, I can say with confidence that this has been one of the most valuable investments we’ve made as a business.
We Didn’t Partner Because We’re Family
We partnered because we were different.
Each of us brought something unique to the table — different strengths, different ways of thinking, and different instincts in how we approach decisions. This diversity laid the foundation for our business.
But diversity also introduced friction. When strong personalities with varied perspectives come together, tension is inevitable. The question isn’t if tension will exist; it’s how you manage it.
Therapy as a Structure for Alignment
Our therapy sessions typically last between one and two hours. We discuss everything: strategic decisions, disagreements, personal challenges, and how each of us is showing up inside the business.
It’s not always easy. Many sessions involve conversations that would be difficult to have without a structured environment. But that is the point — instead of letting issues build over time, we address them early. Instead of avoiding uncomfortable conversations, we create space for them.
Research from the Harvard Business Review supports this approach, showing that regular, structured communication prevents conflict escalation and improves team cohesion over time.
Most partnership breakdowns don’t stem from a single moment but from unresolved tension that compounds. Our therapy sessions help reduce that accumulation.
Alignment Requires Intentional Investment
Many businesses invest heavily in growth areas like strategy, hiring, marketing, and operations. Fewer invest in the alignment of the people responsible for that growth.
We treat therapy as a core operating expense — a line item on our profit and loss statement — and one we are proud of. Not because it’s unconventional, but because it reflects how seriously we take the partnership.
Alignment does not happen automatically. Trust does not maintain itself. Strong relationships do not operate on autopilot. They require consistent attention.
The Impact Over Time
This practice has influenced how we operate in ways that go beyond communication. It has helped us:
- Move through disagreements more efficiently
- Make decisions with greater clarity
- Navigate high-pressure moments without damaging the relationship
- Maintain trust even during periods of stress
It has also strengthened our relationship outside of the business. Improved communication in one area often carries into others.
This does not mean we don’t disagree — we do, often. But the difference is how we handle those moments.
While this approach may not be right for every team or partnership, creating a consistent space for open, structured communication can be extremely valuable, especially in high-pressure environments like entrepreneurship.
It’s less about therapy specifically and more about the principle behind it: making time to stay aligned before misalignment becomes a problem.
Final Thought
Businesses can be rebuilt. Relationships are much harder to repair.
For us, investing in therapy has been a way to protect both. It’s not something we turned to because things were broken — it’s something we committed to so they would not break.
Over time, that decision has become a foundational part of how we operate.
