As a kid, I spent many winter afternoons playing Monopoly. I loved the tactile pleasure of handling the color-banded deeds, the understated Chance and Community Chest cards, the pretty fake money, the dice, and the iron – my favorite token. But the game itself made me anxious.

Counting out $200 for Reading Railroad was fine; it seemed like an honest deal. Yet no adult had ever bothered to explain what a mortgage was and I was terrified of going bankrupt (another scary word I didn’t understand). I didn’t want to risk all my assets on a big red Connecticut Avenue resort just to watch that pale-blue deed be plucked away by my evil-landlord brother.

Who knew I’d be a successful Realtor one day, “playing” with actual homes instead of miniature green-plastic houses!?!

After three decades spent selling San Francisco real estate, I can name a few parts of the game I still don’t like. Yet, I’ve learned it’s a noble and fun profession. I help others navigate a route to home ownership, a destination with no clear map or legible key – no matter how many new apps are developed to simplify the process.

The layperson thinks the game is about dollars and interest rates and market trends and bedroom counts and school districts. It is. And it isn’t.

Buying or selling a home is really about love. It’s about people just wanting to know that they’re going to be okay. It’s about them wanting to know, “Will I be loved?”

Could you be loved? Yes, you could. Yes, my clients are. (Speaking of, click here to hear a fun acoustic cover of that classic tune.)

My personal real estate playlist is heavy on Bob Marley. Because I get high on helping my clients feel AND BE safe and empowered while playing with big big big bucks. Real bucks, not funny money.

“Don’t worry about a thing,” I say, when the game gets scary, “cause every little thing is gonna be alright.”

Photo Credit: Clint Bustrillos 

Cynthia Cummins is the founder of Kindred SF Homes and has been serving homeowners and homebuyers for 3 decades. For information on San Francisco Bay Area real estate visit For my writing and mindfulness blog, visit