The Day I Almost Quit

By Mike DelRose Jr.

Belmont, MA .Thursday, November 20, 2025

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It still sits with me, more than ten years later.

I’ve finally found the clarity and courage to share an experience that nearly drove me out of real estate for good. This post isn’t a masterclass or a marketing piece. It’s a catharsis. But if you’re in this business or have worked with someone who is, there are important lessons here worth sharing.

A Detour That Became a Calling

In 2009, I graduated with a degree in marketing and minors in sports management and business administration. At the time, joining the family real estate business was the furthest thing from my mind.

I was all-in on a career in professional sports. I even paid for one last academic credit after graduation just to intern with the Kraft Sports Group. That summer was meant to be my launchpad. But the economy had other plans.

It was the aftermath of the financial crisis. Companies were slashing marketing budgets left and right, and landing a job in sports, or anywhere near it, wasn’t looking good. Sales roles were available, but they weren’t in the direction I was aiming.

Around the same time, real estate was evolving. The internet was shifting from a helpful tool to a mission-critical platform. I pitched an idea to Mike Sr. Let me modernize the business; systems, branding, marketing, and then I’d move on to “Mike Jr.” things.

Only I didn’t.

What started as a stopgap turned into a passion. I discovered I loved guiding people through life-changing decisions. It gave me purpose. It was emotional, intense, and deeply rewarding. 

But a few years in, one situation made me question whether it was worth continuing.

The Knock on the Door

It was a normal day at the office. I wore a suit every day back then and took calls on a desk phone—both rarities now. A local homeowner called and asked me to provide a broker price opinion. They knew our family and wanted to hear what we thought.

When I arrived, the owner shared something that immediately raised red flags: they had recently gone through a major medical issue and weren’t thinking clearly. My instincts kicked in. This person didn’t need just representation. They needed advocacy.

We walked the property and talked options. Then someone knocked on the door.

A person was standing there with a purchase contract in hand. No prior appointment. Just… there.

My first thought: was I too late?

Too late to earn the business? Maybe. But more importantly, was I too late to help protect this person?

What most of my clients know about me is this: I’m not attached to being the one who gets the listing. I’m attached to doing the right thing. And in this case, that meant ensuring someone vulnerable had professional eyes on a major decision.

Doing the Right Thing and Getting Burned

Before I left, I asked for the name of the owner’s attorney and gave them a call. I explained the situation, not to interfere, but to flag that someone who explicitly told me they were mentally compromised was about to make a significant financial decision.

I told the attorney, paraphrased:

“Your client just told me they’re not thinking clearly due to medical reasons. They’ve received an offer on their home. I’m not inserting myself into the deal, but they need someone looking out for them, and they named you.”

I hung up that call thinking I did the right thing.

I was wrong.

The Fallout

Later that day, or maybe it was the next, I got a call from the seller. What followed was one of the most brutal phone calls of my career. I was berated, insulted, and mocked, with personal details from my background thrown back at me.

Apparently, the buyer had told them I was clueless, didn’t know what I was doing, and dug into my public bio online for ammunition. I was blindsided.

I explained that I hadn’t interfered with the transaction. I didn’t ask for business. I simply alerted their legal representative with their permission because I thought they needed help. That’s it.

And still, I got torched.

The hardest part? Realizing that trying to do the right thing could end up hurting you.

In that moment, I questioned everything. Not just my actions, but my entire career. Was it even worth it?

The Aftermath

A few days later, the seller called back and genuinely apologized.

The buyer, likely a local contractor, did end up purchasing the home months if not a couple of years later. He probably still thinks I’m an idiot. That’s fine.

Because even now, more than a decade later, I’m okay knowing that I did everything I could to protect someone who might have been taken advantage of.

The Takeaway

So what’s the lesson?

No good deed goes unpunished? You can’t win them all? Maybe. Or maybe there’s no lesson at all, just the reality that doing the right thing doesn’t always feel good or end well.

But here’s what I do know:

I’m not going to change.

I’m not entitled to anyone’s business. But when someone asks for my help, they’ll get the full extent of my care, my expertise, and my advocacy. No shortcuts. No apologies.

Over the years, there have been other moments that tested my resolve. That comes with the territory in this business. But the difference now? I expect those moments. And they won’t derail me.

Because I didn’t get into this for easy wins. I’m here to do right by people. Even when it’s hard.