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Nobody Ever Feels Ready. That's Not How This Works.

By
Real Estate Agent with Keller Williams/ The Monday Team

I want to tell you about a couple I worked with in Oakland ... longtime homeowners, two kids, a dog, a home office situation that had gotten genuinely out of hand. They had been in their house for nine years and it had been the right house for about six of them.


The last three years they had been saying some version of the same thing every time we talked.


"We'll know when it's time."


I love this couple. I also want to be honest about what "we'll know when it's time" actually means in practice ... because after twenty-five years in and around real estate I have heard this sentence approximately ten thousand times and here is what I have learned:


Nobody knows when it's time. Time doesn't announce itself. It doesn't send a calendar invite or show up with a sign. What actually happens is that one day you're standing in your kitchen at 7am trying to simultaneously make lunches and answer emails and locate a missing cleat and you realize with absolute clarity that this house stopped working for your life somewhere around eighteen months ago and you've just been too busy to stop and acknowledge it.


That moment is not a revelation. It's an accumulation.


In the Bay Area right now ... with rates coming down slightly and properties still moving in Oakland, Alameda, the East Bay broadly ... the buyers who are acting are not the ones who felt ready. They're the ones who got honest about what waiting was actually costing them.


Not in a fear-based way. In a clear-eyed, let's-actually-look-at-this way.


Because here is the thing about move-up timing in this market: the gap between your current home and your next one does not stay the same while you wait. Sometimes it closes. Sometimes it widens. The only way to know which direction it's moving is to actually look at the data instead of waiting for a feeling that real estate was never going to deliver anyway.


At The Monday Team we have a conversation we call the "what is waiting actually costing you" conversation. Not to create pressure ... but to replace the vague anxiety of "we'll know when it's time" with actual numbers and actual options.
Because clarity is always better than waiting for a feeling.


And in twenty-five years ... nobody has ever told me the feeling came first.


Agent Takeaway: "We'll know when it's time" is almost always a placeholder for a conversation the client hasn't had yet. Your job is to have it with them ... gently, honestly, and with real data.

Comments(1)

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Will Hamm
Hamm Homes - Aurora, CO
"Where There's a Will, There's a Way!"

Hello Kerri I am so proud of you sharing your blogs with us here in the Rain.  Keep it up.  I will try to help you get points that you can get it free.

Jul 21, 2026 10:00 AM