At This Stage… The Plan Was Good. But Life Moved

I’ve decided to start sharing these reflections publicly because I have a feeling many of us are thinking about the same things — just not always saying them out loud.

This note may resonate more depending on where you are in your life right now. For some, these are conversations happening today. For others, they’re a few years away.

And for many… they’re already starting.

This fall, my son Julian and his partner Lauren are moving into their first home.

And honestly? I couldn’t be more excited for them.

It’s one of those proud mama moments you don’t fully prepare for. Watching your kid step into homeownership — into that next chapter — is something else. It’s exciting and emotional and wonderful all at once.

But here’s the thing.

Time changes things.

And knowing Julian and Lauren are about to step into their own next chapter has made me start asking different questions about mine. Questions I didn’t know to ask at 48. But at 56, it’s different.

Because eight years ago I had a plan. A real one. Redesign the main floor. Separate the upper and lower levels. Create income. Build flexibility right into the property itself.

It was a good plan. I still believe in it.

And the question I keep coming back to is this:

Is now still the right time to invest $200,000 or more into this house?

Or has something shifted?

Because when I’m really honest with myself — I think about property taxes. Maintenance. The ongoing cost of a home that’s going to keep asking for money. I wonder if there’s a window here. A moment where the smarter move isn’t to invest more into staying…

But to finally ask what’s next.

Out of curiosity.

Out of intention.

At this stage, I have equity. And honestly — if you bought your home 20 or more years ago, chances are you do too. More than you might realize. More than you’re probably doing anything with right now.

That’s not nothing.

That’s options.

But I think a lot of us were raised by parents who stayed in their home until they couldn’t anymore. It’s what that generation did. And without even realizing it, we absorbed that. Staying put feels responsible. Familiar. Safe.

Even when everything around us is quietly telling us it might be time to think differently.

I don’t have the answer yet.

But I’m asking the question out loud now.

And I have a feeling I’m not the only one.