PlainMoneyPress

55, still working, still learning. Writing down what I wish I'd known at 25 so my kids and yours land somewhere better than I did. Free checklist below.

[PlainMoneyPress @ventures_4]

I am 55 and I am not where I hoped to be.

I have a day job. I have built a few small businesses on the side to make up ground. Seven kids, one paid off truck with almost 200,000 miles, and a long list of money things I figured out about twenty years later than I should have.

That is not a complaint. It is the reason I started writing.

Nobody sat me down and explained any of this. Not in school, not at home. So I have been writing down the things I wish I had known, in plain English, no jargon and no lectures. Three volumes now, for the three stages where it matters most: getting a child started, the launch years in your twenties, and the protection years when wills and beneficiaries stop being abstract.

I am not a financial advisor and I will never tell you what to buy. I can only tell you what I got wrong.

The whole goal is simple. I want my kids, and yours, to be in a better spot at 55 than I am.

Everything is in my bio, including a free checklist.

[PlainMoneyPress @ventures_4]

@Wisconsin_fam Speaking if seasons…I think the Reds are ready to start their OFF-season🤷🏻‍♂️

[PlainMoneyPress @ventures_4]

Any "rituals" in your family household?

[PlainMoneyPress @ventures_4]

We had a rule in our house. Dinner got made & if you didn't want it, that was fine. We called it fend for yourself. Several of my kids are in their twenties now & they STILL call it that.

[PlainMoneyPress @ventures_4]

Random thought: Is it crazy to start celebrating birthdays backwards once you’re over 50? 😂

Instead of 51, 52, 53… maybe start counting down.

Sure, it’s probably a ridiculous little mind trick. But maybe there’s something philosophical about it. We spend the first half of life counting how many years we’ve accumulated, then suddenly realize the number that matters isn’t necessarily how many are behind us but how intentionally we spend the ones ahead.
Getting older isn’t about counting down. It’s about making every year count. ❤️

Or maybe I’m just trying to negotiate with Father Time. 😂

[PlainMoneyPress @ventures_4]

@GrulkeLamonte For an existing home should a qualified HVAC contractor be able to handle this and would this be more affordable than replacing a standard AC system?

[PlainMoneyPress @ventures_4]

I’ve leaned on this verse many times over the years, both in business and in family. It’s easy to reach for “I can do all things through Christ” when things are difficult and we need strength to get through them. But your point about contentment when things are going well really hits. Learning to be grateful for what God has already provided—and not constantly chasing the next thing—may be the harder lesson. There’s a lot of wisdom in that.

[PlainMoneyPress @ventures_4]

@RickardExplorer @FromTeachrsDesk Agreed. That's part of the culture shift I can't wrap my mind around. Everything is "unfair" to many.

[PlainMoneyPress @ventures_4]

I think we’re seeing some of this play out from the “No Child Left Behind” philosophy. In trying to make sure no student gets left behind, we may have sometimes made it too easy to simply move students forward without truly mastering the material. Some lessons have to be learned through struggle—and yes, even failure. Protecting kids from every difficult experience can ultimately be a disservice when they reach adulthood and discover the world doesn’t work that way.

[PlainMoneyPress @ventures_4]

This hits home. My parents rescued me from credit card debt when I was a young adult, and it took me a long time to unlearn the habits that created it. I got my first credit card at college orientation with basically zero financial education—a pretty bad combination. 😂 I’m grateful they helped me, but I also learned from it. I refuse to let that cycle repeat with my own kids. I want to give them the tools, knowledge and resilience to handle life themselves—not just rescue them when things go wrong.

[PlainMoneyPress @ventures_4]

Automatic beats disciplined every time...willpower asks how you're feeling that week. A payroll deduction doesn't ask you anything at all. Set it & forget it. What was the first thing y'all automated?

[PlainMoneyPress @ventures_4]

This really resonates. I used to be pretty quick with sarcasm and thought, “They know I’m joking.” But a quick laugh in the moment isn’t always worth the possibility of crushing a kid’s spirit or becoming part of their inner voice. I’ve learned to be much more intentional with my words. Still learning, but that awareness makes a difference.

[PlainMoneyPress @ventures_4]

@ThrillaRilla369 TG&Y

[PlainMoneyPress @ventures_4]

@marcar @StickWithNate WOW! Now that's a memorable one. What a "wizard".

[PlainMoneyPress @ventures_4]

@StickWithNate It was called a Sony Walkman. 🎶📼🎧

[PlainMoneyPress @ventures_4]

@Budgetdog_ Shania was onto something… “It don’t impress me much.” 😂 Money gets noticed. Character gets remembered.

[PlainMoneyPress @ventures_4]

@Mr_Husky1 "Everyone in the story is having a much worse night than you are."

Laughed out loud at that. Best closing line I've read all week.

Have a good Friday.

[PlainMoneyPress @ventures_4]

Honest question.

If they're working before 18, why wait to start the Roth? My understanding is there's no minimum age...as long as they've got earned income you can open a custodial Roth & contribute up to whatever they made.

Seems like waiting until 18 gives up years of tax free growth for nothing. Am I missing something?

[PlainMoneyPress @ventures_4]

Two days ago. Exact same thing. 😂

I tried explaining that the extra penny means a clean dollar back instead of a handful of change, & I watched her genuinely consider whether I was running some kind of scam on her.

The register still balances. Promise. I've never been a math whiz but these are the little things not being taught anymore.

[PlainMoneyPress @ventures_4]

Getting out of the comfort zone occasionally wakes up something you forgot you had.

I'm a creature of habit to a fault. Same order, same seat, same everything. Feels efficient right up until you realize you haven't been surprised by anything in a while.

Good on that barista. And good on you for saying yes.