Last week I told you about Jamie’s cash piling up in her HYSA.

The balance that kept growing. The machine that was fully functioning, as designed. And the two little words I kept saying every time we sat down to review her numbers.

“Cash drag.”

She’d smile. She’d nod. She’d give me a sweet little side-eye. And she would change the subject.

And I’d tell myself that next time, she’d finally hear it.

She didn’t. Because I was trying to solve the wrong problem.

I kept showing up to have a conversation about money. But the conversation Jamie actually needed to have? It had nothing to do with money at all.

Before we could talk about what to do with Jamie’s cash, we had to make sure she felt like her bases were covered.

Not in theory. Not in a spreadsheet. In her gut.

She craved financial security WAY more than optimization.

So we built what I call “sinking funds.” A dedicated little bucket of money for every “what if” that was living rent-free in the back of her head.

An emergency fund. A travel fund. A car maintenance fund. Even a fund for Mili. Because if you’ve ever owned a dog, you know emergency vet bills give zero fncks about your investment timeline. 🐶

Once her short-term needs had a cash bucket, something shifted for Jamie.

The remaining cash, the big pile that had been sitting there growing quietly for years, suddenly had nowhere to hide.

It didn’t have a real job anymore.

And that’s when we finally had a real conversation. One that had nothing to do with money.

Once her sinking funds were set, I started asking Jamie a different kind of question.

Not “what should we do with your cash?”

Not “do you want to see how much the cash drag is costing you?”

Simply:

Jamie had a smart, thoughtful answer for everything else we discussed.

But not this.

She just couldn’t make it make sense.

The more we talked, the more we saw the pattern. Her dad had always said real estate was a smart way to diversify. Her friends were all buying. It was just the next thing you did once you had enough money saved up.

But when I asked questions from a different angle:

Something in Jamie shifted.

It’s like she was Freaky Friday switched into the body of one of our many homeowner friends in Missoula. The ones who spent whole weekends on house stuff. The ones who were still slogging through years-long home renovations. The ones that had repairs, upgrades, yard work, and a never-ending list of projects.

We would watch all of it and Jamie would quietly say the same thing every time.

“I don’t want that.”

Not the house. Not the maintenance. Not the projects. She’d even seen what my rental property demanded of me. She wanted none of it.

She just hadn’t given herself permission to say it out loud.

I want you to think about this...

Jamie’s story isn’t really about buying a house.

It’s about what happens when you spend years doing the “right” things (saving aggressively, building towards something big, checking all the boxes) without ever stopping to ask if they’re the right things for you.

The house was just the most expensive version of a question Jamie had never been asked.

And I’d be willing to bet you have a pretty expensive version of it, too.

Maybe it’s not a house.

Maybe it’s the city you moved to because that’s where the real opportunities were.

Maybe it’s the promotion you chased because the job title looked impressive on paper.

Maybe it’s the arbitrary savings target you’re grinding towards, without knowing what it’s actually for.

The “supposed to” path doesn’t always look like a mistake from the outside.

To some, it looks like success.

A growing account balance. A responsible plan. A life that checks all the right boxes.

But somewhere deep down underneath all of it is a question nobody thought to ask you.

What do you actually want?

Not what your parents wanted for you. Not what your friends are doing. Not what the next logical step is supposed to be.

What do YOU want?

Once Jamie got honest about what she actually wanted her life to look like, something changed.

The “cash drag” conversation stopped feeling like a lecture from an annoying partner.

And the numbers I’d been trying to show her for years? She finally wanted to see them.

Next week: what those numbers actually looked like, and why they were impossible to ignore.

For now, here’s my question for you:

What your version of “the house” you think you "should" be pursuing?

Hit reply. I read and reply to every single response.

– Joe

P.S.

If you’ve been sitting on cash and quietly wondering what it’s actually for, that’s exactly the conversation my free Clarity Call is built for. No pressure and no pitch. Just a friendly chat. You can book one here.

​https://www.levelupfinancialcoaching.co/clarity-call​
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Joe Maddux

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