Hey! Read this August 3, 2026

Does it still fit, or are you making it fit?

I’ve been thinking a lot more metaphysically in my advancing (ahem) years.

And that’s led me to a question most people don’t ask often enough:

  • Is the way we live actually working?
  • Not just, “Can we afford it?”
  • Not just, “Do we like the house?”
  • Not just, “Is the payment okay?”

I mean the deeper stuff.

  • Is this house still helping our family?
  • Is it helping our marriage?
  • Is it helping our kids?
  • Is it helping our sanity?
  • Is it helping our schedule?
  • Is it helping our future?

Because I take people out all the time to look at property and it’s becoming clear to me that they’re agonizing over the house, and the systems and the bedrooms and the kitchen.

But sometimes they haven’t challenged themselves with what actually works for them NOW. And not what worked for them x years ago.

Because over time, a house can quietly stop being a fit without anyone really naming why.

Maybe you need more room. Yes, let’s split the kid’s bedrooms up.

Maybe you need less land. Yea, I don’t want a tractor anymore.

Maybe you need less maintenance. The raised tomato beds were awesome, but I now hate them.

Maybe you need a quieter place.

Maybe you need to be closer to school, work, friends, yoga, or the life you actually want.

Maybe Boulder still makes sense.

Maybe South Boulder makes sense because of the schools and the easy access to US 36. But wait, do we even use US 36 all that much?

Maybe Erie gives you more house and more family utility. But there’s no food there.

Maybe Lafayette is the sweet spot. But is it really ‘coming on’ or is that a publicist saying that?

Maybe Louisville is still the best balanced bet. But goddam, there’s never any inventory so it’s rich.

Maybe the mountains are the answer. What’s with this septic stuff; where do I learn about that?

Maybe it’s time to get out of the churn and into something simpler.

And maybe the real question isn’t where the market is headed.

Maybe the real question is whether your current setup is still helping you win.

That means looking at more than price.

It means looking at:

  • time spent commuting.
  • time spent maintaining the place.
  • how much stress the house itself creates.
  • whether the location fits your day to day life.
  • whether the space fits your family now, not your family seven years ago.
  • whether the neighborhood still feels right.
  • whether staying put is actually the cheapest choice, or just the most familiar one.

A lot of people think moving is the expensive part.

Sometimes it is.

But sometimes staying is expensive too.

Not always in dollars.

Sometimes in friction.

Sometimes in time.

Sometimes in missed opportunities.

Sometimes in the cost of forcing a life to fit a house that no longer fits the life.

So, the question becomes simpler:

Are we living in the right place, in the right space, in the right way?

Or are we just used to it?

That’s worth auditing.

And if the answer is unclear, that’s probably the sign to stop and look harder.

I don’t push you sell or buy or anything.

I just wish some people had come along at points in my life and asked me to consider these questions at turning points.

Peace.