Opinions expressed by Entrepreneur contributors are their own.
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.
I had heard too many stories of family businesses falling apart. Relationships strained. Communication breaking down. Personal and professional lines getting blurred beyond repair. I didn’t want that to be our story.
So when we decided to build Mid-Day Squares together, we made one decision on 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?
But nearly eight years later, I can say with confidence that it 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. Different instincts in how we approach decisions. That diversity is what gave the business its foundation.
But it also introduced friction. Because when you have strong personalities with different perspectives, tension is not a possibility. It is a guarantee.
The question is not whether tension will exist. The question is how you manage it.
Therapy became a structure for alignment
Our sessions typically last between one and two hours. We discuss everything.
Strategic decisions.
Disagreements.
Personal challenges.
How each of us is showing up inside the business.
It is not always easy. In fact, many sessions involve conversations that would be difficult to have without a structured environment. But that is exactly the point. Instead of letting issues build over time, we address them early. Instead of avoiding uncomfortable conversations, we create space for them.
In our experience, most breakdowns in partnerships do not come from a single moment. They come from unresolved tension that compounds over time. This process helps us reduce that accumulation.
Alignment requires intentional investment
Many businesses invest heavily in growth. Strategy, hiring, marketing, operations. But fewer invest in the alignment of the people responsible for that growth.
We treat therapy as a core operating expense. It is a line item on our P&L, and one we are proud of. Not because it is unconventional, but because it reflects how seriously we take the partnership.
Alignment does not happen automatically. Trust does not maintain itself. And strong relationships do not operate on autopilot.
They require consistent attention.
The impact over time
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. Because when communication improves in one area, it tends to carry into others.
This does not mean we do not disagree. We do. Often. But the difference is how we handle those moments.
This approach may not be right for every team. Every partnership is different.
Every dynamic has its own context.
But what we have learned is that creating a consistent space for open, structured communication can be extremely valuable, especially in high-pressure environments like entrepreneurship.
It is 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 is not something we turned to because things were broken. It is something we committed to so they would not break.
And over time, that decision has become a foundational part of how we operate.
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.
I had heard too many stories of family businesses falling apart. Relationships strained. Communication breaking down. Personal and professional lines getting blurred beyond repair. I didn’t want that to be our story.
