How a Cheerleading Coach Talked Me Into 36 Years of Real Estate

People ask me sometimes how I got into this business, expecting some carefully planned career move. The truth is a lot less strategic than that, and honestly, a lot better.

The Run-In

I wasn't looking for a new career. I ran into my old cheerleading coach, someone I hadn't seen in years, and she'd gone into real estate. She asked what I was up to. I gave some ordinary answer. And she smiled and said I should get my license.

I brushed it off. She didn't.

The Part Nobody Believes

She didn't ask once and move on. She asked again. And again. Every time our paths crossed, there it was, the same question, the same smile, like she already knew something I hadn't figured out yet. I've told this story so many times that people assume I'm exaggerating the persistence. I'm not. That's exactly how it happened.

Eventually I stopped saying no. Not because I had some grand vision for a 36-year career. Just because she wore me down in the kindest possible way, and some small part of me was curious enough to find out what she saw that I didn't.

What I Didn't Know Yet

I got my license without any real plan beyond that. On the other side, I found a job that fit me in ways I hadn't expected. I liked people. I liked houses. I liked being the person who helped a family figure out one of the biggest decisions they'd ever make. Thirty-six years later, I'm still doing it, and I still think about that coach every so often, because none of this happens without her refusing to take no for an answer.

Why I Tell This Story

I tell it because it's true, and because it's a good reminder that the people who end up loving what they do rarely plan it out perfectly in advance. Somebody sees something in you before you see it in yourself, and sometimes the whole rest of your life comes down to whether you finally listen.

It's also just who I am with my clients. I don't let go of a family's goals easily either, the same way that coach didn't let go of me. If I believe something's the right move for you, I'm going to say so, clearly and honestly, even if you need to hear it more than once.

The Bottom Line

Thirty-six years, over a thousand families helped, and it all started because someone refused to let me brush her off. I never looked back.

If you're working with me now, or thinking about it, that same persistence is exactly what you're getting, someone who tells you the truth, stays with you through the whole process, and doesn't quit on your goals just because the first answer was "not yet."

Bonnie Fleishman has specialized in waterfront and move-up real estate across Anne Arundel County for 36 years, serving Pasadena, Glen Burnie, Severna Park, Arnold, Crofton, Gambrills, and Annapolis.