I recently had an employee ask me for a $2,000 loan to help cover unexpected funeral expenses for his mother. My feelings were mixed, and I had to sit with them for a while to catch my bearings. I wanted to experience all the emotions I felt, because it wasn’t a clear-cut yes for me, and I think it’s important to be honest about that.
On one hand, I felt bad. I like to believe I am a kind person. Anytime someone experiences the loss of a loved one, you know they are in pain. You know they can feel lost, like their entire world has become unmoored. It scares me to think about, as my own parents are still here, but I know that day is inevitable. My immediate instinct was to say yes.
Then the adult version of me, the one who has lived in the real world, chimed in. I’ve been burned in the past by loaning money to employees. Since then, I swore to myself I had learned my lesson and that I would not do it again.
I tell my kids the world teaches you if you’re willing to remain open.
I also knew that word of this loan would travel within my team, and I didn’t want to open the door to it becoming an unspoken expectation. Not to be callous, but as a business owner, there is a unique feeling that only you truly understand. The responsibility of the business sits squarely on your shoulders.
If things go wrong—and they will—it’s up to you to fix them or to take responsibility. No employee can fully understand what it feels like to have to come up with payroll when business operations fall short, or to sit in mediation with a disgruntled former employee who is suing you for wrongful termination.
These are real things that happen to people who have big hearts but also understand that a business has to be a business.
When you blur the line between personal and professional, which is easy to do in a small company where the team begins to feel like family, you can make things messy. And I don’t like messy. As I say, I have plenty of problems. I don’t need to create systems that generate more. I value my peace and tranquility in life.
The same goes with friends and family. You can say no, and you should, if it puts you in a situation you are not comfortable being in.
Boundaries are what make adult relationships work and stay healthy. Knowing where yours are and being able to articulate them is a skill we all need in today’s world, where expectations can be high, time is scarce, and fewer and fewer people seem to have real peace in their lives.
Because here’s the truth I keep coming back to:
I can want to support you, and I can feel empathy for what you’re going through, and I can still say no. I don’t have to be involved. And I don’t have to feel bad about that.
Frank Losi was loud, opinionated, and larger than life—and he believed in me before I knew how to believe in myself. This is a tribute to the man who helped me make the leap from employee to business owner, and what it means when someone sees your potential before you can.
This is the story of how I once pissed myself on a stalled New York City subway train—and why I wouldn’t trade that night for anything. It’s about shame, letting go, and realizing the world doesn’t revolve around you. Thank God.
I used to think leadership meant having the answer. But over time—through parenting, running a business, and watching one brilliant baseball coach reframe a moment—I’ve come to believe something else: asking the right question might be the most powerful move we can make. This post is about the shift from control to curiosity, and what happens when we lead with belief instead of certainty.
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